Nathan Barry Archive

In today’s episode, I sit down with investor, entrepreneur, and content creator, Sahil Bloom (in front of a live audience) to unpack the key strategies and lessons that will help you achieve longevity and sustainability in the creator economy.Sahil has had a fascinating journey, transitioning from the world of private equity to making a name for himself in the creator economy (his bi-weekly newsletter alone has more than 400K subscribers). Upon entering this new sector, Sahil found himself occupied with the question of how to ensure longevity and set about putting together the ideal business operating system for content creators. In today’s conversation, you’ll get a behind-the-scenes look at how Sahil built a thriving ecosystem as a content creator by acquiring businesses that would resonate with his audience and partnering with the right collaborators. You’ll also hear Sahil’s answers to live audience questions where he sheds light on finding the right partner, knowing when to pivot, and the future of the creator ecosystem.In this episode, you'll learn:How Sahil became one of the first people to popularize the use of long-form on TwitterWhy to focus on building an audience with whom your work resonates rather than chasing vanity metricsHow to figure out if you're creating inspiration-driven content operation-focused content (and where you lie on the spectrum)How to escape the need to create new content daily by putting strategies in placeHow to use flywheels as the operating system for your businessHow to find the right collaboratorsHow Sahil uses agencies to turn cost centers into profit centersWhen to pivot on a project or companyHabits for creating and managing your time as a creatorLinks & Resources:The Sweaty StartupWait But WhyJustin WelshTim FerrissSahil Bloom Links:Sahil’s websiteFollow Sahil on LinkedInFollow Sahil on TwitterFollow Sahil on InstagramFollow Sahil on YouTubeFollow Sahil on TikTokSubscribe to Sahil’s newsletter

Today, I talk to Darrell Vesterfelt, who is a longtime friend who helped grow ConvertKit in our craziest growth times (from $100,000/mo when he joined to $500,000/mo in just over a year).Darrell is one of the best marketers I know. He is the Founder and former CEO of Good People Digital, the Co-Founder of Homestead Living, and Co-Founder and COO of the School of Traditional Skills.In this episode, Darrell breaks down the goal and execution of an online summit that accumulated an astonishing 101,000 attendees as a brand-new brand! Tune in to find out why you can’t have a marketing strategy without value and vice versa.In this episode, you'll learn:Darrell’s transition from New York to homestead; how his marketing skills translate to homesteading.The importance of authenticity in the homesteading world.A rundown of Darrell’s various businesses.The publication and publishing house, Homestead Living: what inspired it and where it’s going. The structure, marketing strategy, execution, and conversion rate of the School of Traditional Skills Summit.The best marketing strategy according to Darrell.Links & Resources:Homestead LivingHomestead Living on InstagramSchool of Traditional SkillsHomesteading FamilyGood People DigitalEverything Worth PreservingDarrell Vesterfelt Links:Darrell’s websiteFollow Darrell on LinkedInFollow Darrell on TwitterFollow Darrell on Instagram

In today’s episode, I’m joined by PJ Taei, Founder and CEO of Uscreen, an all-in-one video monetization platform for content creators that helps them build their brands and grow their businesses. The creator economy has changed a lot since PJ first founded Uscreen in 2015. And in that time PJ has managed to grow Uscreen to $20 million a year in revenue, representing sought-after clients and their channels, like Yoga with Adrienne and Justin Rhodes’s streaming platform, Abundance Plus. Our conversation gets into some pretty fascinating topics, like what to do when major competitors enter your field, the trial and error involved in getting your pricing right, and why true fans are so valuable for content creators looking to monetize. PJ also sheds light on what motivated him to bootstrap his company and expands on why it’s so important to stay in touch with the needs of your customers as you grow!In this episode, you'll learn:How Uscreen supports creators by helping them sync their offerings on one platform.What helped PJ recognize the need for a service like Uscreen.When to fear a major competitor coming in and why you should never underestimate a small company.The importance of continued focus on the customer as you grow along with actionable advice on how to stay in touch with their needs.How to find the right balance between trial periods, free content, and attracting paying customers.Why PJ decided to bootstrap instead of pursuing funding and what he has learned from the experience.Links & Resources:UscreenUscreen on YouTubePJ Taei’s Links:PJ’s websitePJ’s emailFollow PJ on LinkedInFollow PJ on TwitterFollow PJ on YouTube Listen to PJ’s Podcast

In this episode, I talk to Susie Bulloch, who runs Hey Grill, Hey, which started as a wildly successful food blog (to the tune of a million dollars or more a year in revenue). Then she did something that I absolutely love: she used her online business to kickstart a physical products company. Her sauces and rubs company in the barbecue space is now about to overtake the blog in revenue.The online world of content creation is vastly different to the product manufacturing space, and as Susie explains, she is grateful that she didn’t know too much before she made the transition. Her top piece of advice for anyone interested in doing the same thing is to make products with the intention of fulfilling a need, not just because you have an audience online. Susie describes herself as “terrifyingly driven,” and during our conversation, she talks about how she went from “I could never” to doing it all, the importance of celebrating business milestones, the value of having someone ask you, “Why?” regularly on your entrepreneurial journey, and her goal of increasing the representation of  women-owned brands in the barbeque space!In this episode, you'll learn: The value in working for other people before starting your own company. Why it’s always worth taking the time to be grateful for the journey you are on and celebrating your achievements.What the life of a “terrifyingly driven” entrepreneur looks like. How to build trust within your community so they are happy to pay for your offerings.The only piece of advice Susie would give to someone interested in transitioning from online content creation to product manufacturing. Links & Resources:Hey Grill, HeyThe Grill Squad‘The Billion Dollar Creator’Susie Bulloch Links:Follow Susie on TwitterFollow Susie on FacebookFollow Susie on InstagramFollow Susie on YouTubeSubscribe to Susie's Grill Squad

Today, I sit down with the Head of Deliverability at ConvertKit, Alyssa Dulin, to shed some light on the often mysterious game of getting your email into the right inbox. Alyssa's expertise about what creators need to focus on and the most recent developments in the email marketing space can truly take your company's reach to the next level!Deliverability has always been a huge part of what we offer at ConvertKit, and Alyssa unpacks the most important pieces of this puzzle, covering sender reputation, effective cadences, and setting and delivering on expectations. As with so much of our philosophy, it is all about playing the long game over short-term wins and shiny statistics. You’ll get a look behind the scenes at how the world of email actually operates and evolves, the important conversations that happen between providers, as well as some helpful practical tips and common mistakes to avoid. Be sure to join Alyssa and me for this illuminating chat. In this episode, you'll learn:The biggest factors that contribute to reaching your audience's inbox.A simple and comprehensive definition of deliverability.How to think about the important aspect of reputation management. The real value of custom domains and dedicated IPs.  Links & Resources:ConvertKit's Creator NetworkEventbriteWarby ParkerEmmaCM GroupTim FerrissSusan CainJames ClearBitlySpamhausM3AAWGFigmaSubstackSparkLoopAlyssa Dulin Links:Follow Alyssa on TwitterListen to Alyssa's podcastSubscribe to Alyssa's newsletter

Today I’m talking with Thomas Frank. Thomas built a YouTube channel called College Info Geek to over a million subscribers. Since then, he’s rebranded and grown the channel to nearly 3 million subscribers. He’s also built a massive business around courses and Notion templates.In this episode we talk about making a pivot as a creator. Thomas has an interesting and understated approach that’s worked quite well. We also talk about the Notion templates he’s selling, the YouTube productivity channel he started strictly about Notion, and how it’s driving hundreds of thousands of dollars in sales per month.Thomas also explains why it’s easier getting started on YouTube today than it was 10 years ago, and I get Thomas’ candid thoughts on how Gumroad’s new pricing has affected his business and creators in general.In this episode, you’ll learn:Why now is a great time to get started on YouTubeHow to pull off a successful rebrand of your creator businessWhy your subscriber count isn’t as important as you thinkWas Gumroad’s price increase a mistake?Thomas’ Links (H5)Thomas’ websiteFollow Thomas on TwitterSubscribe to Thomas’ YouTube channelDownload Thomas’ Notion templatesCheck out Thomas’ Notion YouTube channelThomas’ Nebula.tv contentFollow College Info Geek on TwitterThomas’ Skillshare page

In this episode I talk to Brian Feroldi. Brian is an incredible creator in the investing space. He Tweets about money, investing, and self-improvement. He also has a free newsletter with over 40,000 subscribers.Today Brian talks about his recent experience migrating his newsletter to ConvertKit. He’s also a member of the ConvertKit Sponsor Network. I haven’t said much about the Sponsor Network, so Brian shares how he’s using it to book sponsors.The bulk of our conversation, however, is about Twitter and how he’s grown his account to over 400,000 followers. Brian has an interesting idea using your Twitter profile as a sales page, and he explains why conversion rates are important. We also pull up my Twitter profile and Brian gives it a tear down live on the show.In this episode, you’ll learn:How to get more followers on TwitterTwitter profile strategies that increase your conversion rateWhy your Tweets aren’t getting more impressionsHow to write Twitter threads that people will shareLinks & Resources (H5)ConvertKit Sponsor NetworkSahil BloomJames ClearTim UrbanBlake BurgeAustin LiebermanBrian’s Links (H5)Brian’s newsletterFollow Brian on TwitterConnect with Brian on FacebookBrian is on InstagramCheck out Brian on YouTubeBrian’s LinkedIn page

The podcast is back! Today I’m talking with Turner Novak. Turner is someone I’ve followed for a long time. He has an amazing Twitter account where he drops hilarious memes, talks about life as an investor, and makes fun of venture capitalists and founders.He also posts deep dives on companies like Snapchat about how their earnings work, what’s going on in TikTok ads, and a lot more. It’s an interesting balance, and he does all this while investing in early-stage companies as a venture capitalist.In today’s episode Turner and I talk about how he creates content. We get into how he uses his funnel to raise capital, and how to generate the highest return on investment (ROI) for your audience. We also talk about how he grew to 130,000 followers on Twitter, why he failed to get a job in venture capital and had to start his own firm, and how to create a successful newsletter.In this episode, you’ll learn:Easy ways to grow your newsletter audienceHow Turner varies his content to get more engagementWhy getting to know your audience is so importantHow Turner used writing to expand his venture capital networkTurner’s Links & Resources (H5)Subscribe to Turner’s newsletter, The SplitFollow Turner on TwitterBanana Capital’s websiteFollow Banana Capital on Twitter

In this episode I talk to Katelyn Bourgoin. Katelyn is a creator and entrepreneur. She’s built several successful companies and agencies, and built a consultant company that she later sold.We dive into why customers buy, and how to market and sell to them through the Jobs-to-be-Done framework. Katelyn has a wealth of marketing knowledge she shares with us today.We talk about different business models. We get into why you should focus on selling checklists, cheat sheets, and outcomes rather than the traditional video courses. We also talk about how she grew her newsletter to 10,000 subscribers, and got to over 50,000 followers on Twitter.In this episode, you’ll learn:Tips and strategies for acquiring more usersA subtle mindset shift to make your marketing more effectiveWhat content should be free, and what should be paid forWhy Katelyn transitioned away from launches and coursesLinks & ResourcesEpisode 061: Rachel Rodgers – Simple & Consistent: How To Build an 8-Figure BusinessApril DunfordNathan Barry: AuthorityKatelyn Bourgoin’s LinksCustomer CampFollow Customer Camp on TwitterThe Why We Buy newsletterJobs-to-be-DoneThe Trigger TechniqueTwitter thread about The Trigger TechniqueFollow Katelyn on Twitter

In this episode I talk to Laura Roeder. Laura and I have been friends for a long time. I’ve learned so much from her, and it’s great to have her on the podcast.Laura started an online community and a course called Creating Fame. She’s done a bunch of stuff in the internet space. She’s one of the people who’s been doing it since the early days.She got into software with a company called MeetEdgar, which is a social media scheduling service, and grew it into a successful company before selling it. She recently started another company called Paperbell. Paperbell is the all-in-one software that solves all the problems of running a coaching and consulting business.There’s so much to learn from Laura. I love her direct, blunt style. She’s given me great advice over the years, and you get to tune in as we jump on a call, hit record, and start catching up.In this episode, you’ll learn:Benefits of choosing a narrow niche for your businessCommon branding mistakes to avoid when starting outLaura’s advice for writing great copyTradeoffs between hiring freelancers and employeesLinks & ResourcesMama GenaMeetEdgarLaura Roeder’s LinksLaura’s websiteFollow Laura on TwitterLaura is on InstagramPaperbellFollow Paperbell on TwitterPaperbell is on InstagramFollow Paperbell on FacebookCheck out Paperbell on Pinterest

In this episode I talk to Justin Moore. Justin is a Sponsorship Coach & the founder of Creator Wizard, a school & community that teaches you how to find & negotiate your dream brand deals.In today’s episode Justin reveals how narrowing in on sponsorship coaching was a huge boost for his business. We talk about him growing multiple audiences between different YouTube channels (he and his wife, April, have well over a million combined followers on YouTube).My favorite part of the episode is when we dive into From Boise, my side project newsletter. Justin breaks down what we’re doing wrong with sponsorships, how we should be selling them, and how there’s quite a bit more to be earned. We also dive into the way he runs his newsletter and how he’s grown it.In this episode, you’ll learn:The differences and similarities between sponsorships and newslettersJustin’s tips for starting your newsletter and getting tractionHow a simple change in Justin’s Twitter headline led to amazing growth for his brandWhy you need to charge your sponsors different amountsLinks & ResourcesDeepak Malhotra: Negotiation Genius: How to Overcome Obstacles and Achieve Brilliant Results at the Bargaining Table and BeyondJustin Moore’s LinksJustin’s websiteJustin's newsletterFollow Justin on TwitterJoin Justin’s group on FacebookJustin’s TikTokJustin is on InstagramCheck out Creator Wizard on YouTubeTrending FamilyAprilJustinTV on YouTube

In this episode I’m joined by Kaya Yurieff. She is the Creator Economy Newsletter writer for The Information. It’s the publication I read when I want to know what’s going on in startups and funding, learn about Spotify’s latest launch, find out what’s going on with Instagram, and things like that.Kaya has a great approach. I love her writing. I love the way she profiles both individual creators and the moves happening from big businesses in the creator space.We talk about her writing process and her system for publishing four days a week. We talk about how they’ve grown the newsletter and what they pay attention to for monetization. We also talk about what it means to be a creator through crises like the pandemic, the social justice issues of the last few years, and now the war in Ukraine.In this episode, you’ll learn:Tips for finding your niche in a crowded fieldHow to get more paid subscribersBenefits of adding visual content to your newsletterHow to balance free content and paid contentLinks & ResourcesEmbeddedKate Lindsay’s post on Embedded: You don't need to post through a crisisKaya Yurieff’s LinksThe Information’s Creator Economy NewsletterFollow Kaya on Twitter

In this episode I talk to Wes Kao, co-founder of altMBA. Her latest startup is called Maven, and it's all about cohort-based courses.Wes is fantastic at course design. Before Maven, she did a bunch of amazing things working with a lot of different creators.We talk about the State Change Method, which is something I use to make my presentations much more interesting. We talk about building an audience on Twitter. We also talk about course design, cohort-based courses, and a lot of other fun things.In this episode, you’ll learn:Tips for writing short-form content that boosts engagementA big advantage Twitter gives you over other platformsHow to know if your content is ready to publishWhy cohort-based courses are so lucrativeLinks & Resources (H5)Seth GodinaltMBAGagan BiyaniWes Kao’s Links (H5)MavenWes’ websiteFollow Wes on TwitterWes’ blog post: Course Mechanics Canvas: 12 Levers to Achieve Course-Market FitWes’ blog post: The State Change Method: How to deliver engaging live lectures on Zoom

On today’s show I’m talking with Brennan Dunn. Brennan is a longtime friend. He's been around since the very early days of ConvertKit. He helped me review pull requests from our very first developers.These days Brennan is an expert in all things email marketing and automation. He’s fantastic at segmenting lists, personalizing content, using Liquid, and other advanced techniques to create a custom experience for subscribers.We talk about some of the ways you can gradually get into automation. We go over some examples of the advanced things Brennan does with Liquid and snippets to create custom experiences for subscribers. We also talk about how you can earn more money from email with these systems, and much more.In this episode, you’ll learn:Strategies for tailoring your website to boost engagement & salesHow to free up more time so you can focus on growing your audienceBrennan’s tips for creating and sharing the right content for your audienceHow to make your repurposed content feel fresh & relevantLinks & ResourcesConvertKitShopify’s LiquidRightMessageBrennan Dunn’s LinksCreate & SellCreator Email Template PackDouble Your FreelancingBrennan’s book: Double Your Freelancing RateMastering ConvertKitFollow Brennan on Twitter

In this episode I talk to Sahil Bloom. This is Sahil’s second time on the show. He’s doubled his audience from an already large number since then, and he’s now a full-time creator.Sahil is someone I’d love to have on the show every six months or every year. He’s putting out incredible content. I’ve probably learned more from Sahil in the last few months than I have from any other person.We talk about Twitter growth, monetization, growing a podcast, and newsletters. I also try to sell him on switching to ConvertKit. You can be the judge of how well I did to convince him.In this episode, you’ll learn:Two game-changing habits that can lead to big resultsHow Sahil categorizes his content for more engagementSahil’s strategies for growing a new podcastHow Sahil monetizes his newsletterLinks & Resources (H5)James ClearShane ParrishThe Generalist (Mario Gabriele)Greg IsenbergThe Tim Ferriss Show, episode 362: Talent Is the Best Asset Class — Graham DuncanSahil Bloom’s Links (H5)Follow Sahil on TwitterListen to Sahil’s podcast, Where It HappensVisit Sahil’s website

On today’s show I talk to Isa Adney, a resident storyteller at ConvertKit.Isa came to ConvertKit as our webinar producer. You get to hear the arc of what she was doing before, how she joined the team, and how it morphed into her current role.Isa is very good at systems. She shares how she uses systems to free up time for creative activities. We also talk about reusing content, and how to create systems and flywheels to make one piece of content work across many platforms.In this episode, you’ll learn:How to connect with popular creators you admireThe best medium for building a relationship with your audienceIsa’s advice for hosting workshops and webinarsHow Isa utilizes systems to create content across multiple mediumsLinks & Resources (H5)ConvertKitConvertKit podcastsDon Hahn: Brain Storm: Unleashing Your Creative SelfKimberly BrooksThe Nathan Barry Show 053: Kimberly Brooks – Taking Intentional Breaks To Reignite CreativityHarlem's Fashion Row (HFR)The Nathan Barry Show 026: Khe Hy – How You Can Do $10,000/Hr WorkConvertKit Creator StoriesIsa Adney’s Links (H5)Follow Isa on TwitterIsa is on InstagramFollow Isa on TikTok

In this episode, I talk to Ellen Hyslop, Co-Founder of The Gist.The Gist is a newsletter all about sports, written entirely by women. Ellen and her co-founders have scaled a massive team to 20 people. They’ve grown The Gist to almost 400,000 subscribers, and they’re earning fantastic revenue from it.Ellen talks about how they grew The Gist in the early days. She also talks about their process of testing, how they launched with a launch party, and a bunch of other things.In this episode, you’ll learn:How to get subscribers when you’re first starting outWhy you need to create a style guide for writing your newsletterTips for growing your newsletter to 400K subscribersWhen niching down can lead to more revenueLinks & ResourcesThe Gist Co-Founder Jacie deHoopThe Gist Co-Founder Roslyn McLartyEllen Hyslop’s LinksThe Gist websiteThe Gist newsletterThe Gist of It podcastFollow Ellen on Instagram

In this episode I talk to Rachel Rodgers. Rachel is an attorney turned business coach. She’s someone I’ve admired and respected for a long time. She helps small business owners understand contracts and the legal side of running a business, and helps them scale their business.Rachel is a lot of fun, and she’s brilliant at business. She’s my hero because of the way that she approaches scaling a massive and successful business, and how she thinks about brand and everything else.On today’s show we talk about why business partnerships are a bad idea. Rachel shares her keys to building a successful membership community, and the benefits of publishing a book. We also talk about why you should take expensive vacations, how to build a great team, and much more.In this episode, you’ll learn:Why offering more products can hurt you in the long runRachel’s clever method for scaling a businessThe relationship between current events and a successful creator businessHow Rachel builds an effective teamLinks & Resources (H5)Nathan Barry: AuthorityDenise Duffield-ThomasConvertKitRachel Rodgers’ Links (H5)Hello SevenThe Hello Seven podcastWe Should All Be Millionaires: The ClubWe Should All Be Millionaires: A Woman’s Guide To Earning More, Building Wealth, and Gaining Economic PowerSmall Business BodyguardFollow Rachel on TwitterRachel is on Instagram

In this episode I talk to Reid DeRamus. He comes from the video streaming world of Hulu, HBO Max, and Crunchy Roll. His background in data analysis helped these companies grow their streaming services.Now he’s taking what he learned into the creator space to help people with their paid newsletters and courses, bringing these growth habits and growth techniques into their solo or small team creator businesses.We spend this episode riffing on business models, and the analytics that you should pay attention to as an individual creator. We also discuss branding, positioning, and local meetups. It’s a fun episode that I think you'll enjoy.In this episode, you’ll learn:Tips for developing your brand and communityReid’s process for curating contentHow to get your work in front of an audienceThe path to over 500K subscribersLinks & ResourcesPatreonWait But WhyCrash Course on YouTubeminutephysics on YouTubeMinuteEarth on YouTubeReid DeRamus’s LinksFollow Reid on TwitterYem

In this episode, I talked to Samir Chaudry. Samir is the co-host of the popular YouTube channel, Colin and Samir. He and his business partner, Colin Rosenblum, have built a really interesting enterprise. It’s been fun getting to know them.We talk about how they built and structure their entire business, and what drives revenue. Then we get into storytelling, and at the end we even talk about designing the perfect day, what’s driving growth on YouTube, and much more.They’ve got a show, they’ve got a newsletter, a bunch of different stuff. It’s a fun story of two people who were shining in a specific niche, took what they learned from that experience, and are serving the broader community with their knowledge and wisdom.In this episode, you’ll learn:How to avoid being overwhelmed as a creatorHow Samir & Colin developed a culture around their contentTips for curating your contentThe journey to over 500K subscribers on YouTubeLinks & ResourcesConvertKitSamir Chaudry’s LinksFollow Samir on TwitterColin and Samir on YouTubeThe Colin and Samir Show on Apple PodcastsThe Colin and Samir Show on SpotifyThe Publish Press newsletterColin and Samir on Instagram

Andrew Gazdecki is the founder and CEO of MicroAcquire, the world’s most founder-friendly startup acquisition marketplace. MicroAcquire helps entrepreneurs buy and sell startups.After founding and later selling two successful startups, Andrew decided there needed to be a better way to connect buyers and sellers in the startup marketplace. He founded MicroAcquire to fill this void in the startup acquisition arena.In this episode, Andrew shares how he grew his Twitter audience from 30,000 to 70,000 followers in a few short months. He uses his connections with others, his partnerships, his brand, and savvy marketing techniques to boost engagement and attract followers. It’s a fun and entertaining episode, and I think you’re going to enjoy it.In this episode, you’ll learn:The one thing you should spend at least half of your startup’s budget onProven strategies and tactics to grow your Twitter accountHow to bootstrap your business and retain your autonomyLinks & ResourcesTechCrunchCameoEffieEmpire FlippersFlippaBizness AppsSam ParrStripeBaremetricsChartMogulBumbleBrandarrowBootstrappers.comY CombinatorSalesforceNick HuberDavid CancelJosh PigfordClearcoAngelListAvaloqNaval RavikantDharmesh ShahThe Ladders of Wealth Creation blog postAndrew Gazdecki’s LinksFollow Andrew on TwitterFollow MicroAcquire on TwitterEpisode Transcript00:00:00 Andrew:I’m a big fan of stair-stepping and entrepreneurship. One of my favorite tweets that I’ve ever written is, “Start with an agency, get to cashflow positive, and then bootstrap an asset—whether that’s a SaaS company or your e-commerce business—sell that asset, become financially secure, and then do whatever you want.”Along the way, you prepare yourself for the next stage of business. 00:00:35 Nathan:In this episode, I talked to Andrew Gazdecki, from MicroAcquire. Andrew started a couple other businesses and sold two of them. In that process, he decided there needed to be a better way to buy and sell businesses. So, that’s where MicroAcquire came from. Their marketplace originally focused specifically on SaaS businesses, but they broadened to all of software.The reason I want to talk to him—he doesn’t write a traditional newsletter or something like that—but he uses audience really well to grow MicroAcquire. He uses his personal brand connections with others, partnerships, a bunch of fun things.We get into how he grew his Twitter audience from 30,000 followers just a couple months ago, to over 70,000. His approach to Twitter, some of the arguments or beefs that he started with TechCrunch and others, and where he thinks those lines are.We also get into how he uses Cameo; he has these great ads announcing partnerships and others from Russ Hanneman on Silicon valley talking about this, and they’re really entertaining.So, there’s a lot of fun things in this episode, and I think you’re going to like it.I’ll get out of the way, and we’ll dive in.Andrew, welcome to the show.00:01:41 Andrew:Thanks for having me, Nathan. Always a pleasure to be chatting with you. 00:01:44 Nathan:There are a lot of companies in the brokerage/help-me-sell-my-business space. I think of Effie International, Empire Flippers, Flippa, all of these. So, one, you’re going into a really crowded market with MicroAcquire, and then, two, you’re coming at it like you’re a force of nature.Sam Parr and I we’re actually talking about this, of how some people start a project and it’s like, “Oh, I’m going to do this thing.” And then other people do effectively the same thing. I mean, it’s different in a lot of ways, right? But the same category, and come in and just completely dominate, and grow so fast, and it feels like a fundamentally different thing.What’s your take on that, of coming into a crowded space, and then the amount of momentum that you’ve come in with?00:02:34 Andrew:Yeah. I have a lot of respect for all those companies that you mentioned, and appreciate the compliment.The market that is specifically acquisitions hasn’t seen a lot of innovation in a decade. Two of the businesses you mentioned are service businesses, Flippa being a marketplace. I looked at that, and I just thought, there’s an angle here where sellers could benefit more than the buyers, and I felt buyers were benefiting. So, I took a left while everyone was going right.Then coming in from an entrepreneur’s view instead of a buyer’s view, or an investment bankers view, or an MNA advisor view, this was me saying, okay, I’m gone through two acquisitions, I think I have a few unique insights into what it would take to make me comfortable putting my business, generating millions of dollars, on a new marketplace. Then, what information and educational pieces would I need to feel comfortable to facilitate an acquisition.So, I just built what I felt acquisition should be. We still have a long way to go. We’ve done a really good job of connecting buyers and sellers, and all the acquisitions are facilitated off platform. We’ve been working on a lot of tooling to really add value to the acquisition, if that makes sense.So we’re looking to innovate on things like due diligence or even simple items like writing a letter of intent or streamlining escrow, because everyone complains about escrow.com. so yeah, I mean, sometimes it just happens in markets. Like a new entrant comes in with a different angle towards the problem And different viewpoint. and I think my unique, insight there was just, I had been on. The side of the table that maybe the other, companies had not. but it’s also, a giant market. So I, think, arising boat lifts all tides. So, you know, we’re here to my require. I just made my group or to help entrepreneurs get acquired and, and, succeed.And so, I think also as, you know, Mike require pick steam and helps everyone else in the market as well. So, but, yeah, I don’t have a good answer to that. I don’t know. I think if I, if I, this, this will sound cheesy, but you know, I, I I’d like to say I built my group hire would love, like I launch...

Sherrell Dorsey is the founder and CEO of The Plug, a publication and community for news, insights and analysis on trends in Black innovation. The Plug features stories that show the substantive ways Black people engage with the innovation economy, including analyses of modern technologies.On today’s show, Sherrell shares about building an audience and growing The Plug. We talk about sponsorships, The Plug’s revenue model, and her background in journalism and how she brings that into her current work. We also talk about choosing a niche, staying consistent, and much more.Sherrell has worked in marketing and consulting for companies such as Uber, Tresata, MarketSource, and Build The Good. Sherrell has also worked as a correspondent for Fast Company, Essence, Next City, and Black Enterprise. She earned her master’s degree in data journalism from Columbia University.In this episode, you’ll learn:How to grow your subscribers when first starting outDifferent strategies for monetizing your newsletterThe right way to include advertising in your newsletterTradeoffs between having a team and working as a solopreneurLinks & ResourcesClay HebertMonica MeltonFarnam StreetShane ParrishRyan HolidayDaily StoicJames clearUberGoogle FiberMicrosoftFast CompanyThe RootBlack EnterpriseGoDaddytheSkimmSignalBloomberg TerminalBusiness InsiderThe Moguldom NationSherrell Dorsey’s LinksFollow Sherrell on TwitterThe PlugThe Plug newsletterHBCU newsletterTPinsights.comEpisode Transcript00:00:00 Sherrell:I think that we’ve gotten into this very fast pace, and this idea of constant information and voices in your head. I don’t know that more information is making us a better society. I think that this idea of community and grappling with ideas, calling things out or bringing things to attention, but having something meaningful to say really outweighs just being visible all of the time. 00:00:31 Nathan:My guest today is Sherrell Dorsey. Sherrell is the founder of The Plug, which is a newsletter, and really a publication at this point, about the black tech ecosystems and all the interesting things that black and brown founders are doing in technology and business. She started in 2016, and she’s built it up to have a full-time team of five people now.I’m so impressed with what she’s built. We get into talking about sponsorships, the revenue model, how she built the audience, her background in journalism, and how she brings that into what she’s doing now. I actually grew up in tech and some of the ecosystems that she was a part of that inspired her.We talk about choosing a niche and staying focussed there. We talk about consistency. There’s really a lot of things in this episode. I love what she’s doing and how she’s built this niche business into something that now employs full-time journalists. At a time when a lot of other publications are dwindling, she’s growing.So, let’s dive into the episode.Sherrell, welcome to the show.00:01:35 Sherrell:Thank you so much for having me.00:01:37 Nathan:I actually want to start talking about experimentation. We’re going to jump around a little bit. You like to run a lot of experiments, and you’ve taken an approach on experimentation where you’re doing it at a stage in the business where you have a lot going on. A lot is working. This is a point where I see a lot of content creators freak out and stop experimenting because they’re like, “This is what my audience likes. I have to show up in exactly this way.”So, they don’t experiment. Even at this level of success, you’re like, “No, experimentation is a core part of what we’re doing.”Could you talk about that, and some of the experiments that you run, and then your mindset around it?00:02:12 Sherrell:We’re constantly challenging ourselves as a team, and trying not to get bored. Part of our experimentation may have more to do with the attention deficit issues that we have as a team, as a collective. Maybe not as much as our audience, but we also assume that they also have attention issues.Let’s be honest, there’s so much competing for our audience’s attention, right? I mean, outside of the inbox, theres social media, there’s the day-to-day of all the crazy, all the push notifications. So, for us, experimentation really is at the core of challenging ourselves to face something new and interesting, and really tapping into what.The sort of timeliness of news, and really finding a way to put it into our voice and share some of our opinions as well. Even with running The Plug’s weekly briefing experimentation is really even just how I got started. The Plug for me was an experiment. I was getting up at 5:00 AM, pulling together a newsletter, wanting to cover diverse voices in tech.Doing it just as this labor of love, and also nerdiness and curiosity, and it started to grow. Then I said, well, maybe I can do this every single day. Then I did it every day. Then at some point we realized, hmm, are people having inbox fatigue? What if we slow things down and really make people cherish every single sentence that we’re writing in our newsletters, and giving them a long and deep side of slow conversations on Monday mornings as they’re starting their day.We’ve seen those questions that we’re asking kind of manifest in this idea of experimenting with just our curiosity. We’ve seen that well, I mean, honestly, Nathan, we’re getting 45% to 48% open rates on every single newsletter, and it has been pretty consistent.When we were in the daily phase, we were starting to see those open rates go down. People just didn’t even have enough time to read. So, again, we start with the question, “Well, what if, or how do we personally sort of engage with our news and with our information, and how do we create a moment of almost intimacy with our audience and our subscribers?” Where instead of just having the breadth, we can actually have the depth.00:04:40 Nathan:Yeah. I want to talk about the consistency and the schedule later in the episode, but let’s go there right now because I think a lot of...

Matthew Kepnes runs the popular travel blog, Nomadic Matt, and also writes a successful newsletter. In fact, Matt’s newsletter is one of the biggest I’ve had on the show. His book, How to Travel the World on $50, is a New York Times Best Seller.After a 2005 trip to Thailand, Matt decided to leave his job, finish his MBA, and travel the world. Since then, he’s been to nearly 100 countries, and hasn’t looked back. Besides being a New York Times best-selling author, Matt’s writings have been featured in countless publications. He’s a regular speaker at travel trade shows, and is the founder of FLYTE, a non-profit organization that sends students overseas to bring their classroom experience to life.I talk with Matt about his unique approach to running his business. While others are building online courses, Matt has shifted to doing more in-person meetups and events. We talk about his newsletter, and we also talk about growing your Instagram follower count, scaling a business as a solopreneur, and much more.In this episode, you’ll learn:When & why you need to start outsourcing day-to-day tasksMatt’s email opt-in strategies and tips to get more subscribersThe most important metric about your email listHow to quickly get more followers on InstagramLinks & ResourcesBlue Ocean StrategyMatadorLonely PlanetBlue Ocean Strategy bookPat FlynnWomen In Travel SummitTraverseCheryl StrayedConvertKitTravelConFinConPodcast MovementWorld Domination SummitHootsuiteTim FerrissSeth GodinOptinMonsterSeth Godin: This is MarketingRick StevesNathan Barry Show on SpotifyNathan Barry Show on Apple PodcastsMatthew Kepnes’ LinksMatt’s websiteFollow Matt on TwitterMatt’s InstagramThe Nomadic NetworkNomadic Matt PlusEpisode Transcript[00:00:00] Matthew:When I started these courses back in 2013, there wasn’t a lot of folks. Now you have so many people with courses, so many Instagrammers and TikTokers selling their stuff. It’s sort of like, is this worth the time to really invest in it when my heart really isn’t in it? How can I maintain 400K in revenue a year? Is that the best use of our resources? The answer is, not really.[00:00:33] Nathan:In this episode, I talk to my long time friend, Matt Kepnes, from Nomadic Matt.Matt’s got a travel blog that’s wildly popular, and he gets into that—shares all the numbers. He’s probably one of the biggest newsletters that I’ve had on the show, so far.What I love about him, in particular, is how thoughtful he is about his business model.Most people are just adding more courses and figuring out how to grow revenue; honestly, what’s now fairly traditional ways, and it’s quite effective. Matt takes another approach. He gets into in-person events and meetups. We get to talk about why in a busy, crowded online world, he’s actually going offline.I think that Blue Ocean Strategy he references, the popular book by the same title, I think it’s interesting, and it’s something worth considering when some of the online strategies don’t work. We also get into a bunch of other things like growing his newsletter. Like I said, it’s quite large.Then, also growing an Instagram following. Instagram is not something that I’m going to actively pursue, but it’s interesting hearing his approach of what you do if you’re at 5,000 followers on Instagram, and want to grow to 50,000 or more.So, anyway, enjoy the episode.If you could do me a favor and go subscribe on Spotify or iTunes, or wherever you listen if you aren’t subscribed already, and then write a review.I check out all the reviews. Really appreciate it. It helps in the rankings, and I’m just looking to grow the show.So, anyway, thanks for tuning in today. Let’s go talk to Matt.Matt, welcome to the show.[00:02:06] Matthew:Thanks for having me, Nathan. I’ve been trying to get on this podcast for ages.[00:02:10] Nathan:Well, don’t say that, that’ll make people think they can get on just by asking. Really, you came to my house and stayed in my cottage on the farm, and then you’re like, “Yo, have me on the podcast!” And that’s when I was like, “Absolutely.” But if anyone just asked, that would not be a thing.[00:02:26] Matthew:No, I just mean I finally—I’m excited that I’m worthy enough in my blogging career to be on.[00:02:33] Nathan:Oh, yes.[00:02:35] Matthew:I’ve made it.[00:02:36] Nathan:Yeah. It’s only taken you, what, a decade and a half?[00:02:39] Matthew:13 and a half years. Slow and steady wins the race.[00:02:43] Nathan:That’s right.I actually want to start talking about that side of it, because I’ve been in the blogging world for 11 years now. But even I feel like things changed so much in the first couple of years, even before I entered into the world. So, I’m curious, going back to the early days, what were the prompts for you to come into the blogging world and say, “Hey, I’m going to start publishing online”?[00:03:10] Matthew:Yeah. You know, it was a very haphazard, there was no grand plan. Like I had Zanger when people had Zeno’s, which is, you know, a personal blog, way back, you know, 2003, whatever. And so what, I went on my trip around the world in 2006, I just kept updating this Zynga. You know, it was called, Matt goes the world and it was just like, here I am friends here I am.And then, you know, everyone was really excited in the beginning. And then after a while I got sick in my update because the know their back of their office job. So I kinda just forgot about it until I came home and January, 2008 and I need money. And so I started a temp job, and I had a lot of free time and I really just hate...

Andrew Warner has been part of the internet startup scene since 1997. Andrew and his brother built a $30 million per year online business, which they later sold. After taking an extended vacation and doing some traveling, Andrew started Mixergy. Mixergy helps ambitious upstarts learn from some of the most successful people in business.Andrew and I talk about his new book, Stop Asking Questions. It’s a great read on leading dynamic interviews, and learning anything from anyone. We also talk about longevity and burnout as an entrepreneur. Andrew gives me feedback about my interviewing style, the direction I should take the podcast, and much more.In this episode, you’ll learn:Why you need to understand and communicate your missionHow to get your guest excited about being interviewedWhat to do instead of asking questionsHow to hook your audience and keep them engagedLinks & ResourcesConvertKitGregg SpiridellisJibJabAli AbdaalThe Web App Challenge: From Zero to $5,000/month In 6 MonthsGrooveZendeskHelp ScoutJordan HarbingerNoah KaganBob HilerSeth GodinMorning BrewAlex LiebermanKeap (formerly Infusionsoft)NotionSahil BloomRyan HolidayBrent UnderwoodGhost Town LivingTrust Me, I'm Lying: Confessions of a Media ManipulatorDamn GravityPaul GrahamY CombinatorNathan Barry: AuthorityIra GlassNPRThis American LifeBarbara Walters Richard Nixon interviewOprah interview with Lance ArmstrongMatt MullenwegChris PearsonConspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of IntriguePeter ThielGawkerNick DentonThe Wall Street JournalRohit SharmaSanDiskJason CalacanisDickie BushSean McCabeDaily Content MachineJordan PetersonTribesWarren BuffetSam WaltonTed TurnerGothamChessLinkedIn Learning (formerly Lynda.com)Inc.com: Selling Your Company When You're Running on FumesChess.comMark CubanJames AltucherRod DruryAndrew Warner’s LinksAndrew WarnerStop Asking QuestionsMixergyEpisode Transcript[00:00:00] Andrew:The top 10 interviews of all time are news-based interviews. We, as podcasters, keep thinking, “How do I get enough in the can, so if I die tomorrow, there’s enough interviews to last for a month, so I can be consistent, and the audience loves me.”That’s great, but I think we should also be open to what’s going on in the world today. Let’s go talk to that person today. If there’s an artist who’s suddenly done something, we should go ask to do an interview with them.[00:00:32] Nathan:In this episode, I talk to my friend, Andrew Warner, who I’ve known for a long time. He actually played a really crucial role in the ConvertKit story in the early days, and provided some great encouragement along the way to help me continue the company, and get through some tough spots.We actually don’t get into that in this episode, but it takes an interesting turn because we just dive right in.Andrew’s got a book on interviewing. He runs Mixergy. He’s been, running Mixergy for a long time. We talk about longevity and burnout, and a bunch of other things. He dives in and challenges me, and gives me feedback on my interviewing style. Where I should take the Podcast, and a bunch of other stuff. It’s more of a casual conversation than the back-and-forth interview of how he grew his business. But I think you’ll like it. It’s a lot of what I’m going for on the show.So anyway, enjoy the episode.Andrew, welcome to the show.[00:01:25] Andrew:Thanks for having me on.[00:01:26] Nathan:There’s all kinds of things we can talk about today, but I want to start with the new book that you got coming out.This is actually slightly intimidating; I am interviewing someone who has a book coming out about how to be good at interviewing. Where do we even go from here? You were saying that you have thoughts?[00:01:47] Andrew:I have feedback for you. I have a thoughts on your program.[00:01:51] Nathan:I’m now even more nervous.[00:01:52] Andrew:I’ve been listening, and I’ve been following, and I’ve been looking for questioning styles. Is there feedback I could give him? I mean, I’ve wrote a whole book ...

Nick deWilde is a Product Marketing Principal at Guild Education. Guild is a fast-growing startup that partners with Fortune 500 employers. Guild unlocks opportunities for America’s workforce via education and upskilling.Nick also runs his newsletter, The Jungle Gym. The Jungle Gym helps readers build a more fulfilling career that integrates work and life. Before working at Guild, Nick earned his MBA from Stanford Business School, and was a Managing Partner at Tradecraft.Nick and I talk about his relationship with Twitter, and how social media can both serve you, and be a challenge. We talk about individual brands and growing a platform. Nick also shares his thoughts about marketing yourself as an individual, and we discuss how growing an audience plays into your career.In this episode, you’ll learn:Building an audience while working full-timeThree reasons people start newslettersWhat to do when your follower count hits a plateauLinks & ResourcesMorning BrewFastlyJoseph Henrich, The Secret of Our SuccessJulian ShapiroSahil BloomDickie BushMediumTiago ForteBuilding a Second BrainDavid PerellWrite of PassageTradecraftGuildHacker newsJohn Lee DumasPacky McCormickMario GabrieleSeth GodinRachel CarlsonOn DeckGongMatt RaglandCharli PrangleyThe Nathan Barry Show, featuring Kimberly BrooksHarry StebbingsThe Twenty Minute VCIsa AdneyLiz Fosslien, No Hard Feelings: The Secret Power of Embracing Emotions at WorkDiscordRedditPalletCraft + CommerceConvertKitEnoughRyan HolidayJames ClearMarie ForleoRamit SethiNick deWilde’s LinksFollow Nick on TwitterNick’s newsletter, The Jungle GymTo tweet, or not to tweetEpisode Transcript[00:00:00] Nick:I’ve tried to do things in my writing where my employer benefits from them. I talk about work a lot, and whenever I talk about hiring, I mention Gild is hiring. There are things I do to just try to make sure that it still feels worth the company’s while.[00:00:25] Nathan:In this episode, I talk to Nick deWilde, who writes a popular newsletter called The Jungle Gym. He’s got a background in product and growth, and all these things from the startup world. I just love the approach that he’s taken to writing these days.We talk about growing as newsletter. We talk about his interesting relationship with Twitter and social media. How it can really serve you and be this great thing, and then it can also be challenging. Maybe you’re spending too much time on it, or time on it in a way that’s not actually serving you or benefiting you.We talk about the rise of individual brands being used to grow a platform. It’s something I’ve been thinking a lot about, watching Morning Brew and Fastly, and some of these other companies do it. It’s just interesting whether you’re marketing as a company or an individual. It’s just a good conversation. We also talk about audience, and just how that plays into your career.He recently made the switch from a full-time role, to doing more audience-based business stuff. He was just in the middle of that journey. So, it’s a fun place and time to catch up in the conversation.Nick, welcome to the show.[00:01:33] Nick:Hey, thanks for having me, Nathan.[00:01:35] Nathan:I want to start on this article you have, that I like a lot, called, “To tweet, or not to tweet,” That got you ahead. I also happened to go to the Shakespeare festival recently, and watched them do “The Complete Works of Shakespeare, Abridged.”So, you know, I could probably pull off a good, to[00:01:50] Nick:Nice.[00:01:51] Nathan:Be or not to be speech right now. It’s in my head because I think about all the wonderful things that Twitter and an audience beyond that does for me. Then also the negative sides of it. So maybe we dive into that, but I’d also love to hear what sparked you diving in and building an audience.[00:02:11] Nick:Yeah, I’m so conflicted on Twitter, and audience building in general. Like anything, I imagine there’s a fair number of people who you talked to, who are in the writing community, who feel that way. On the one hand, Twitter does so many things for me. Especially over the past couple of years.As we’ve been in lockdown, lives have moved online. I have met and made friends with so many amazing people through Twitter that I wouldn’t have met otherwise. Same with the newsletter, but Twitter is a little bit easier to build those relationships.

Kimberly Brooks is a contemporary American artist and author. Kimberly integrates landscape, figuration and abstraction to address subjects of history, memory and identity. Her work has been exhibited and featured internationality.Kimberly received her bachelor’s degree in literature from U.C. Berkeley, and was Valedictorian. She has taught art as a lecturer and adjunct faculty instructor, and was a featured speaker at TEDx Fullerton.In this episode, I talk with Kimberly about her work as an artist, author, and editor. We talk about how she uses ConvertKit to reach and grow her audience. We talk about what people can learn from fine art, and apply it to their newsletters. We also cover the path to becoming a successful creator, and much more.In this episode, you’ll learn:The secret to achieving your breakthrough momentA job most creators should charge for, but rarely doWhat you should be doing instead of bloggingShould you be posting on Instagram?Links & ResourcesHuffington PostConvertKitCraft and CommerceSteve JobsJohn BaldessariAdobe PhotoshopAdobeLeonard ShlainMilton GlaserMacworldWalt Disney’s ImagineeringWarner Music GroupSeth GodinLeonardo da VinciArianna HuffingtonHuffington Post: Fine ArtLaterAnderson Ranch Arts CenterOtis College of Art and DesignKimberly Brooks’s LinksFind Kimberly on InstagramKimberly’s websiteKimberly’s Ted TalkHuffington Post article, “The Gap Logo, New Coke and the Legendary Walter Landor”Kimberly’s book, The New Oil PaintingEpisode Transcript[00:00:00] Kimberly:The fundamental way to learn is, you imitate, assimilate, and then you can improvise with anything. You’re going to be thwarted in the beginning many times, and you can’t give up. You have to say, “Okay, well, I don’t care if it sucks. I don’t care if I’m going to fail. If I’m gonna fail, I’m gonna fail big. Let’s just go on.”[00:00:29] Nathan:In this episode I talk to Kimberly Brooks. She is a fine artist. So, painting, she has all of her art in galleries, that whole world, which is super fascinating to me. She also plays in the creative world. Newsletters, podcasts, and interviews.She built the whole art editorial section of the Huffington Post. She built that to millions of readers. She’s done all kinds of things in the design community from the early days. So, we riff on that; Mad Men-style ad agencies in the ‘80s and ‘90s. Some great stuff.Then she brings it all the way through to talking about what she does with ConvertKit. How she sets up her sequences, and everything else, and things that people can learn from fine art, and apply to their email newsletters and sequences.So, it’s a fun episode. We have to do a part two, because we filled up all the time we had, and I think I only got through half my questions.So, anyway, I’m going to get out of the way and dive in. So, here we go.Kimberly, welcome to the show.[00:01:37] Kimberly:Thank you for having me, Nathan.[00:01:39] Nathan:There’s so many things I to talk about, because you come to the creator world from a different perspective than I do, though we both share a love for Photoshop.[00:01:50] Kimberly:Oh, yeah.[00:01:51] Nathan:We’ll start with where we met. It was at Craft and Commerce, some number of years ago.I can’t even think. Three years ago? Four?[00:02:01] Kimberly:I think it was three years ago, and it was such a random whim. I don’t even know how I ended up finding it. I fell in rabbit hole. And then I came upon ConvertKit.I was actively looking for a better way to send art show announcements. Because I’m a painter, I’m an artist.I just felt after my previous experiences, I knew how important having a subscriber-based service was. I don’t want to get too nerdy, but I didn’t really like the competitor who shall remain unnamed. But, I found you guys, and I started getting the advertisement for the conference, and it was in Boise, Idaho.And so I thought, I’ll just go. It was like a Ted conference for really creative nerdy people like me, but it was exactly what I was wanting. It was about marketing, which is really such a weird word because it’s really about sharing, and I loved the title.I loved everything about it. I met some of the people that I’m really, really close with now. Then the next year it was canceled because of the pandemic, but it was amazing, and I met you, actually.[00:03:28] Nathan:And, and we had a really fun conversation. one thing that I want to talk about, for you is the intersection between fine art, right. And painting and that world. And then now you’re also in this world of being a writer and a creator in the sense, right. You you’ve been a writer and creative for a long time, but, but it’s, it’s like a different world of the selling things to your audience.And. Earning money directly in that way. And so I want, like, I want to hear that as you like weave in and out of these two worlds and then just your experience there.[00:04:02] Kimberly:Yeah, it’s interesting. I, when I was in elementary school, we had a really competitive game of tetherball constantly going on on the playground. And it was just sort of that pole with a ball attached to a rope we would, people would line up and we would get it, and it was, see how many times, and it was just sort of like, it was very intense and I always felt like being an artist.Being an art to me was it was the pole, you know? So like my pole is art is making art and everything about what I do. I write about it. I interview people about it. I interview other artists about their work. I make paintings 90% of the time in my studio. Like, it’s all about art, you know? So that’s like the beginning.So I do see myself sashaying between different worlds. And I think everybody kind of does that. And then as the bicycle of technology was being built to use kind of lik...

My guest on this episode is music industry veteran, Jay Gilbert. Jay wears a lot of hats. He’s a musician, photographer, marketer, speaker, and music executive. Jay has worked as a creative consultant to many record companies and artists. He hosts The Music Biz Weekly Podcast, is a Co-founder of Label Logic, and runs the weekly music newsletter Your Morning Coffee.Label Logic helps artists, managers, and labels grow their audience and optimize their presence across all platforms. Jay’s newsletter is curated to give a weekly snapshot of the new music business. It’s everything you need to know, delivered to your inbox every Friday morning.I talk with Jay about his shift to being a content creator. We talk about life as a musician, working in the music industry, and being a photographer. We also talk about his management company, and his advice for creators wanting to build their audience. Jay also shares some behind the scenes stories, and much more.In this episode, you’ll learn:Simple hacks to grow your newsletterDefining and reaching your target audienceLow-budget tricks to instantly add new subscribersJay’s #1 metric for becoming a successful creatorLinks & ResourcesConvertKitBen BarnesPeopleJeff MoscowTravis TrittAli AbdaalConvertKit’s Creator SessionsMusic Connect (MRC)ChartmetricViberateSoundchartsPollstarCherie HuAmber HorsburghGlenn PeoplesBobby OwsinskiBruce HoughtonHypebotSound & VisionMusic Technology PolicyNancy WilsonRobloxJay Gilbert’s LinksFollow Jay on TwitterYour Morning Coffee newsletterBen Barnes 11:11 on People.comJayGilbert.netLabel LogicThe Music Biz Weekly PodcastEpisode Transcript[00:00:00] Jay:The harder I work, the luckier I get. You make your own luck. You see these people, and you’re like, “Wow, that guy just blew up on TikTok or, Twitch, or on Spotify, or Apple Music!” Sometimes that happens. Not very often, and it usually it’s a lot of hard work.[00:00:26] Nathan:In this episode, I talk to Jay Gilbert. Jay’s a music industry veteran. He’s been at it for a very long time. What I love is that he’s also made this shift into being a content creator, as well as being a musician and a photographer. So many incredible things. He’s got this newsletter about the music industry called Your Morning Coffee, and he’s grown into over 15,000 subscribers.It’s the thing that everyone in the music industry is reading every Friday morning. We talk about how he grew that, his passion for the music industry, how the industry has shifted, what’s working, what’s not. He also runs a management company called Label Logic where they’re partnering with, artists and managers, and doing these album releases, and so much else.He’s got all these behind the scenes stories, and a lot of advice that is not only for the music industry, but also for any creator looking to build an audience, and endure long enough to get noticed, and to build a brand and everything else. It’s really good towards the end.I also sneak in some selfish questions about what would he do to grow ConvertKit; what’s his advice for ConvertKit entering the music industry.Jay, welcome to the show.[00:01:39] Jay:Hey, thanks for having me, Nathan. Good morning.[00:01:41] Nathan:Good morning.We’ll dive into some of your background, what you’re working on now, but you actually had a pretty big project launch today.What did you launch today?[00:01:54] Jay:Well, when you launch a big project, sometimes it’s like a wedding. You have all this planning, planning, planning, and then boom, there it is. It was pretty exciting this morning. We’ve had to keep quiet about this project. It’s Ben Barnes, who is a pretty famous actor, but most people don’t know he’s a brilliant singer songwriter and pianist.We’ve recorded this really great record. We’ve got some amazing videos, given his relationships in that area. They’re quite special. We launched a window of exclusivity this morning with People Magazine.So, if you go to People.com, you’ll see. the video is debuting. It’s pretty special, and we’re really excited about it. It gets released tomorrow. The song’s called 11:11, by Ben Barnes. It’s pretty cool. I think you’ll dig it.[00:02:53] Nathan:Nice. Yeah. If anyone doesn’t recognize the name, Ben Barnes, he plays Prince Caspian. I’ve been a fan of the Narnia series and all that for a long time. I think my kids actually just rewatched Prince Caspian two weeks ago.[00:03:09] Jay:Have you seen shadow and bone yet?You got to check out shadow and bone. My, my wife and I binged watched it. And he’s, he’s brilliant in that, but it’s a really cool series.[00:03:21] Nathan:Nice. Okay. So maybe with that, of like a snapshot of, of what you just launched, Let’s talk about, a little bit about, logic[00:03:32] Jay:Sure.[00:03:33] Nathan:You know, what types of projects you do. And then we can go back to like the road to get.[00:03:38] Jay:Yeah, well, Label Logic was born out of my partner, Jeff Moscow, and I working in the major label ecosystem for years and years. And we finally got to a point where we were meeting one day for coffee and said, you know, we started our own.So we both worked at universal for a long time. He was there 20 years.I was there 18 years. I worked at Warner music, for five years managing Amazon’s business for we at ADA, globally, which was fantastic. but we decided to do our own things. It’s about seven years ago, give or take,[00:04:16] Nathan:Yeah.<...

Sean McCabe is the founder and CEO of seanwes media, and Daily Content Machine. Sean is a prolific and successful creator, author, and influencer. His course, Learn Lettering, made $80,000 in the first 24 hours. For nearly a decade his podcast, blog, and courses have helped creators grow their brands, content, and skill sets.Sean’s website is a treasure trove of courses and resources for anyone looking for business knowledge and creative support. Sean’s book, Overlap, shows creators how to turn their passion into a successful business while working a full-time job. His podcast includes almost 500 episodes on content creation and entrepreneurship. His latest venture, Daily Content Machine, turns creators’ best content into clippable moments they can share across their social media accounts.I talk with Sean about what it’s like being a successful creator. We talk about growing your audience and connecting with them. We cover how to learn new skills fast, and about developing a growth mindset. We also talk about managing stress as a founder, how to handle burnout, and much more.In this episode, you’ll learn:Why good writing is the foundation of great contentHow to connect better with your audienceLeveraging short-form content to grow your brandPricing at full value without feeling guiltyHow to avoid burnout, and what to do if you’re already thereLinks & ResourcesSean McCabe on The Nathan Barry Show episode 003Craft + Commerce conferenceConvertKitEnoughRyan HolidayJames ClearMarie ForleoRamit SethiSean McCabe’s LinksFollow Sean on TwitterCheck out Sean on InstagramSean’s websiteDaily Content MachineEpisode Transcript[00:00:00] Sean:If you are a founder, you should be in therapy. Full-stop. You need a therapist. I thought I didn’t. I had a great upbringing. I’m all good. Everything’s healthy. I don’t have any problems. The problem was I didn’t know the problems that I had. I didn’t realize what I was stuffing down. I didn’t realize what I was avoiding.There is so much to unpack that you don’t know you need to unpack.[00:00:30] Nathan:In this episode I talk to my friend, Sean McCabe. We’ve known each other for seven years now. It’s been a long time. We’ve been in a mastermind group together. He’s actually been on the show before. Sean is a wildly talented designer. He got his start hand-lettering.I think last time he was on the show, years ago, we were talking about that aspect of his business and how he built this substantial course business. Selling courses on hand-lettering, on marketing, on writing. He’s spoken at our conference Craft + Commerce, all kinds of things. Sean is one of the most prolific creators that I’ve ever known.It’s also super fun that he’s a friend and lives right here in town. We just have a great conversation. We talk about how you create content, which is one of those things that it’s not even how you create content, it’s why. Where that comes from. The internal drive in what you use. Where you choose to have as a source of fuel and energy to put into that creative output.How some sources are really good and productive, and others can be kind of like a house of cards, and it can be harmful. We also talk about scaling teams as a creator. How do you know when to build out a team around your business? He’s done that two different ways. So I get to ask him about some of the things he’s learned and applied differently.I’m going to stop there. There’s a lot of good stuff. So with that, let’s dive in.Sean. Welcome to the show.[00:01:59] Sean:Hey, Nathan, just saw you recently. We were playing volleyball, or something.[00:02:03] Nathan:Or something, like two days ago. You moved to my city. It’s kind of…[00:02:08] Sean:Yeah. It’s horrible. It’s a terrible place. Boise. Don’t move to Idaho.[00:02:15] Nathan:You mean Iowa? Boise, Iowa.[00:02:17] Sean:Iowa. Yeah. Don’t, yeah. Did I do okay?[00:02:21] Nathan:Yeah. That’s exactly what you’re supposed to say. If you Google something about Boise, Google has the accordion of extra questions, or things you might want to know. One of them is, “Does Boise smell?” and it’s just like auto complaints in there.And I was like, what is up with that? I clicked on it, and it’s this satirical article that has 12 reasons you shouldn’t move to Boise. One of them is the city dump is right in the middle of the city. Another one is like that the Ebola outbreak hasn’t been fully contained yet.So it’s not really safe. I think there was something about lava. Anyway, it’s just an article about all the reasons to not move to Boise. So I think you’re right in line.[00:03:08] Sean:Stay, away. That’s what they tell me to say.[00:03:11] Nathan:Yes, but if someone were to ignore that and move to Boise, they could come to our weekly volleyball game on Wednesday nights.[00:03:19] Sean:It’s casual. It’s open.[00:03:21] Nathan:Let’s try it. Yeah. It’s been so fun having you and Laci here. It’s also been fun because you started a new company. Your company is producing and editing and creating all the clips for this podcast. So, connections on so many levels.[00:03:37] Sean:Yeah. We produce this show, like the video show, the audio show, and then find clips and make those clips for social media. It’s been great. We love this show. Our team’s favorite content. So, I’m a little biased, but it’s fun to be on. Because my team’s going to work on this.[00:03:58] Nathan:Yeah, exactly. I made sure to spell your name correctly in the setup, and I know they’ll get it all.I wanted to ask what sparked—like maybe first give a summary of Daily Content Machine, since that’s what you’re spending nearly all of your time on. More than a normal amount of time on. So, what sparked it, and what is it?[00:04:19] Sean:Fun fact. This is not the first time I’ve been on the show. The last time was episode three, 2,624 days ago.[00:04:30] Nathan:Give or take[00:04:32] Sean:I was doing different stuff then. It’s been a crazy journey. Right now the newest iteration is an agency.We produce video clips. We turn long form video shows. If you have a video podcast or other kind of long form video content, we found that the hardest part is finding all the good moments in there, and turning those into short clips. ...

Dave Pell has been writing online for almost as long as the internet has existed. His popular newsletter, NextDraft, has over 140,000 subscribers. NextDraft covers the day’s ten most fascinating news stories, delivered with a fast and pithy wit.Dave has been a syndicated writer on NPR, Gizmodo, Forbes, and Huffington Post. He earned his bachelor’s degree in English from U.C. Berkeley, and his master’s in education from Harvard.Besides being a prolific writer, Dave is also the Managing Partner at Arba, LLC. For more than a decade, Arba has been angel investing in companies like Open Table, GrubHub, Marin Software, Hotel Tonight, Joyus, and Liftopia.In this episode, you’ll learn:How Dave merged his two writing passions into a successful productThe key to building a strong relationship with your audienceHow Dave dramatically increased signups to NextDraftLinks & ResourcesFlickerUnsplashFareed ZakariaJim RomeThe SkimmMorning BrewThe HustleSpark LoopSam SprattDave Pell’s LinksDave Pell on TwitterNextDraft newsletterDave’s new book: Please Scream Inside Your HeartNextDraft appPleaseScream.comEpisode Transcript[00:00:00] Dave:If you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it. So, that’s pretty powerful and still excites me. I still press publish with the same enthusiasm now than I did when the internet first launched.[00:00:23] Nathan:In this episode I talk to Dave Pell, who has been writing for basically as long as the internet has been around. He’s been an investor since the early days. He’s been writing since the.com bust, and even before then. He writes his popular newsletter with 140,000 subscribers called Next Draft.We have this really fun conversation about writing. His writing process. How he grew the newsletter. Bunch of other things that he cares about. Even a few things that I was interested in, like he doesn’t have his face in photos on the internet very much. He has his avatar instead. So, just getting into why that is.He also has a book coming out soon. It’s called Scream Inside Your Heart, which is a fun reference to some memes from 2020. So, enjoy the episode. There’s a lot in there.Dave. Welcome to the show.[00:01:12] Dave:Thanks a lot for having me on.[00:01:14] Nathan:Okay. So you’ve been doing this for a long time. You’ve been writing on the internet since the .com era. So, I’m curious maybe just to kick things off, what have you seen—I realize this is a giant question.What have you seen change? What are some of those trends that you’ve seen, that you either really miss from the early days, or some of those things that you’ve held onto from the early days of the internet, that you’re really still enjoying?[00:01:46] Dave:Yeah, that is a pretty huge question, but I’ll give it a shot. The thing I miss from the early days of the internet is that our democracy was not being destroyed by the internet in the early days of the internet. So, everything we thought we were building, basically it turned out to be the opposite of what actually happened.The part about the internet that I still feel is there, although a little bit less so because of the big companies have sort of taken over all the platforms and stuff, is just the idea that someone can have a passion or a creative output that they want to share with the world, and they can mold internet tools to fit their skills, and then use the internet to broadcast that out, and still become sort of pretty popular withour the “OK” of some gatekeeper at a publication, or at a television studio, or whatever.The indie spirit of the internet still lives on. It ebbs and flows, and has a lot of different iterations. But that was the thing that excited me the most when I first played with the internet. And that’s the thing that continues to excite me the most now.[00:02:57] Nathan:I always think of the newsletter, and your newsletter in particular, is that indie spirit. Is that what you see most commonly in newsletters? Or are you seeing it in other places as well?[00:03:10] Dave:I see it in podcasts. I see it in newsletters. I see it in people sharing their art, sharing their photography on Flicker, and up through the more modern tools. I go to a site called Unsplash all the time to look at images, and it’s just basically regular people sharing their images.Some of them are professional photographers, some aren’t, and they’re getting their work out there, and then some of them probably get jobs out of it and stuff like that. So, just the idea that you can have some kind of creative output and have a place to share it. And try to get an audience for that is really inspiring.It’s a lot harder than it used to be because there’s a few billion more people trying to get attention also, and because there are more gatekeepers now. So, you have to, hope that your app meets Apple’s guidelines, or that different products you might want to share on the internet have to meet certain classifications now, whereas they might not have in the very early days of the internet. But in general, if you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it.So, that’s pretty powerful, and, still excites me. I still press published with the same enthusiasm now that I did when the internet first launched.[00:04:32] Nathan:Yeah. So let’s talk about the main project that you have right now, which is Next Draft. Give listeners the 30-second pitch on Next Draft, of what it is.[00:04:46] Dave:Sure. Basically I call myself the managing editor of the internet. What I basically do is a personality-driven news newsletter where I cover the day’s most fascinating news. I cover 10 stories. A lot of times in each section there’s more than one link. I give my take on the day’s news, each individual story, and then I link off to the source for the full story.When I first launched it, I called it Dinner Party Prep. I provided enough information for you to sort of get the gist of the story. And if there’s topics you want to dig deeper, you just click and, you know, go get the story yourself. So that’s sort of the overview of it.[00:05:27] Nathan:Nice. And you said that you’re obsessed with the news maybe in a somewhat, even unhealthy way. why, where did that come from?[00:05:36] Dave:Y...

Jessica DeFino is a freelance beauty journalist living in Los Angeles, California. For the past seven years Jessica has been writing, researching, editing, and publishing about the beauty and wellness industry. Her work has appeared in Vogue, The Cut, Fashionista.com, Cosmopolitan, Marie Claire, Business Insider, SELF, HelloGiggles, Harper's Bazaar, and more.Before starting her career as a freelance journalist, Jessica worked as a beauty writer for The Zoe Report. She was Director of Communications at Fame and Partners, and worked as a ghostwriter for Khloé Kardashian and Kendall Jenner.Jessica earned her bachelor’s degree in Music/Business Songwriting from the Berklee College of Music. Jessica’s music degree brings a unique perspective to her writing. It infuses each piece with lyrical qualities of storytelling, flow, and connection to her audience.Jessica also publishes a bi-monthly beauty newsletter called The Unpublishable, where she shares “What the beauty industry won’t tell you — from a reporter on a mission to reform it.”In this episode, you’ll learn about:Making lasting connections with your audienceWhy understanding music and rhythm makes your writing betterCapturing and keeping your readers’ attention right from the outsetThe dangers of cross-posting your content across social mediaLinks & ResourcesVogue MagazineAllureHarper's BazaarUrsula K. Le GuinRhymeZoneAli AbdaalJessica DeFino’s LinksFollow Jessica on TwitterThe UnpublishableJessica’s InstagramEpisode Transcript[00:00:00] Jessica:I started writing as a songwriter. The musicality of something is very important to me. So I’ll read my own stuff out loud sometimes. I feel when people can read something and there’s a clear flow and rhythm to it, and the words melt into each other sound nice next to each other, it locks them into the content early on. You want to keep reading because if you stop reading it’s like you’re breaking this rhythm that you’ve started.[00:00:34] Nathan:In this episode I talk to Jessica DeFino. She’s a journalist covering the beauty industry, but she tends to take an approach that’s not as popular with sponsors and publishers, because she’s anti a lot of their products and a lot of the nonsense that is put into the products and the marketing behind it.She’s taking a critical angle and she’s well loved by her readers because of it, but maybe not so loved by the big brands. We talk about how that came about. We talk about her writing style, her approach of using her background in song writing and going to school for songwriting to have a better, more interesting writing style.She gives some tips along that angle, talking about how she launched a newsletter last year and growing that to 9,000 subscribers. How that is a backbone for the rest of her work she does in journalism.It’s a great conversation. So, let’s dive in.Jessica, welcome to the show.[00:01:28] Jessica:Thank you so much for having me.[00:01:29] Nathan:We’ll jump around a whole bunch, but I want to start on the launching of your newsletter. What was the moment when you started to think, okay, I want to actually run a newsletter and start to control my own audience?[00:01:44] Jessica:I had been toying with the idea for a while, and then I think it was, April, 2020, right after the pandemic, where I had gotten into a situation where—I’m a freelance reporter—I had four freelance stories out when March happened, and Coronavirus lockdowns happened and everything was up in the air.The company severed ties with all of their freelancers and basically gave these four unpublished stories back to me, and gave me a kill fee. So it was like I had reported out these whole stories. I had spent months on them, and now I had nowhere to put them, and I gave it about a month of pitching it out to other alums.There weren’t any takers because media was in such a precarious position at the time. Finally I was like, maybe this is the opportunity I’ve been waiting for to launch a newsletter. and I decided to call it The Unpublishable because I couldn’t get anyone to publish this. And yeah, it’s been going, almost like every other week.[00:02:50] Nathan:Nice. Yeah. It’s interesting how these unfortunate moments result in something that’s like, okay, this is actually either a good thing now, or hopefully going to be a good thing soon, but it starts with difficult times.[00:03:05] Jessica:Yeah, exactly. I wanted these pieces to be big. They were stories that I thought were important to tell, and I really wanted them to be in a major outlet. Sometimes with media, you can’t sit on things for very long. It was like, I maybe have two more weeks before they stopped becoming relevant.[00:03:23] Nathan:Yeah. So for context, for anyone listening, what were some of those stories as an example?[00:03:27] Jessica:The first story I published with a piece called “Where are All the Brown Hands?” It was a look into the overwhelming whiteness of the top nailcare companies in beauty. If you would look at their Instagrams or if you would look at their websites, everything was modeled on white hands.As a beauty reporter, when I have to source images for the stories, I don’t want to just be showing white hands. If I’m writing about nail trends or whatever, and it would take me hours every week to comb through places and try to find the trend I was speaking to on a person of color. At one point, I was like, why is this happening and how come it’s so hard?This should not be hard. So, I wanted to do an investigation into it, and just like that the whole process had already taken six months. I was like, you don’t know what’s going to happen in this story. It might be scooped. It might be written by somebody else. It might be irrelevant in another month or so.So, I really wanted to get that out there, and that started it.[00:04:31] Nathan:When you publish a story like that, and you’re used to publishing for a major beauty publication, but you’re publishing it for yourself. What did that look like? What was the process of saying, I have this story that I’ve worked on for a long time, and I have a brand new newsletter and all at once.How did you bring that to life and pull the audience together?[00:04:52] Jessica:Well, luckily at that point I had a mask, a little bit of a social media following just from my work on work, like major publications. Like I had been writing for Vogue and allure. Harper’s bizarre. And I had been pretty diligent about building up a social media audience. So I had a pretty sizable, amount of readers just from Instagram.And a couple of years prior, I had like tried starting ...

Ali Abdaal is a Doctor, writer, podcaster, entrepreneur, and YouTube sensation. Ali has grown his YouTube subscriber base to over 2 million, and writes a weekly newsletter titled Sunday Snippets. Sunday Snippets covers productivity tips, practical life advice, and the best insights from across the web.Ali studied medicine at Cambridge University. He worked as a Doctor in the United Kingdom before taking time off to explore his other interests. His YouTube channel covers medicine, tech, lifestyle, and productivity. Ali also co-hosts a weekly podcast with his brother, called Not Overthinking.After learning to code at age 12, Ali started doing freelance web design and development. He enjoys playing piano, guitar, and singing covers of mainstream pop songs. You can find occasional videos of Ali’s music prowess on his Instagram page.In this episode, you’ll learn:Ali’s savvy insights for growing your YouTube subscriber baseA proven formula for writing content titles that get clicksAli’s playbook for taking your podcast to a whole new levelLinks & ResourcesThe Nathan Barry Show on Apple PodcastsThe Nathan Barry Show on SpotifySean McCabePat FlynnConvertKitIbz MoCasey NeistatSara DietschyChris GuillebeauTim FerrissDerek SiversSchool of Greatness podcastLewis HowesDave RamseyMichael HyattCal NewportCrash CourseJohn GreenHank GreenDaily Content MachineAndrew D. HubermanRebootDan PuttTiago ForteDavid PerellJim CollinsThe Flywheel EffectImpact Theory podcastThe Tim Ferriss showSeth GodinScrivenerJames ClearAli Abdaal’s LinksFollow Ali on TwitterWatch Ali on YouTubeCheck out Ali on InstagramAli’s newsletterAli’s websiteEpisode Transcript[00:00:00] Ali:YouTube can change your life, but you have to put out a video every single week for the next two years. If you do that, I guarantee you it’ll change your life. I can’t put any numbers on it. I can’t tell you how many subscribers you’ll have, or how much revenue you have, like a hundred percent guarantee.You will change your life at the very least in terms of skills or connections or friends, or opportunities that will come your way as a result of posting consistently.[00:00:30] Nathan:In this episode, I talk to Ali Abdaal. Over the last four and a half years he’s built his YouTube channel from zero to 2 million subscribers.He’s who all of my friends who are into YouTube turn to for advice. He’s got a paid course. He’s got a substantial email newsletter. He started out as a doctor and then has made the switch into a full-time YouTuber. So anyway, I’ll get out of the way, but, before we dive into the show, if you could do me a favor after the show: if you could go and subscribe on Spotify, iTunes, wherever you listen.That helps with downloads. If you could also write a review, I really appreciate it.Now it’s on to the show, with Ali.Ali, welcome to the show.[00:01:17] Ali:Thanks for having me. This is really cool. I’ve been following you on the internet in a non-weird way since 2016. I remember once in, I think it was 2018, I discovered your 2015 podcast series all about launching an ebook, and pricing plans, and all this stuff.It was so good. Now we’re looking to do eBooks and things like that. Thank you for all the inspiration on that front.[00:01:46] Nathan:Yeah, for sure. Well, it’s fun to have you on, it’s been fun to watch you grow. I was actually on a hike with our mutual friend, Sean McCabe after he moved to Boise, my hometown. He was talking about you, and I hadn’t come across your stuff yet. And I was like, oh, I gotta check it out.And now I’m watching a whole bunch of videos. And then of course we’ve been internet friends for, for awhile now.[00:02:08] Ali:I’m now a customer of ConvertKit as well, for the last few months.[00:02:11] Nathan:Yeah. Let’s see. Okay. So I want to dive into your story and get some context because you have an interesting path of finishing school, like a substantial amount of schooling, and then diving into the world of being a doctor, and then transitioning out of it.What was the plan? Let’s start.[00:02:36] Ali:Yeah. for a bit of context, I spent six years in medical school, and then two years working full-time as a doctor in the UK national health service before deciding to take a break. In that break I intended to travel the world, but then the pandemic happened and I ended up becoming a full-time creator on the internet by virtue of the fact that I didn’t have a job when it was a pandemic.When I first decided to apply to med school, I’d been into the whole entrepreneurship thing since the age of 12. I learned to code. I started doing freelance web design and freelance web developer from age 13 onwards. So, in school, in high school, middle school, like we call it secondary school in the UK, I’d rush back home from school when I finished off my homework in record time, and then just be plugging away at like PHP or some HTML or some like jenky Java script. I used to make $5 here and there, and be like, yes, I’m, I’m making magical internet money. Every year when, when I was in, in high school, my friends and I would come up with a new business idea.So, we started this multi-level marketing thing and some other rando...

Matt Ragland is a productivity expert and full-time content creator. He has worked for companies such as AppSumo.com, ConvertKit, and Podia. Matt graduated from the University of Florida with a bachelor’s degree in recreation & tourism management.Matt was one of the earliest members of the team at ConvertKit, where he was employee number five. Since leaving ConvertKit to start his own company, he now hosts a podcast, publishes a newsletter, has created several courses, and hosts his own YouTube channel.Matt prides himself on being a skilled manager and enjoys helping his clients and audience grow and develop their agencies. He is also the proud father of two boys and is a fitness enthusiast. Matt and his family live in Nashville, Tennessee.In this episode, you’ll learn:Matt’s biggest revenue drivers as a content creatorHow to know when it’s time to take your side hustle full-timeHow to optimize your YouTube channel and contentLinks & ResourcesPodiaRyan DelkBryan HarrisJames ClearSean McCabeSean McCabeLevi AllenCasey NeistatTim FerrissJeff GoinsAli AbdaalMarques BrownleeRoberto Blakeheycreator.comMatt Ragland’s LinksFollow Matt on TwitterWatch Matt on YouTubeMatt’s websiteMatt's newsletterEpisode TranscriptMatt: [00:00:00]If you’re not sure if you want to do something, try it 10 times, and really give it a good try. Write 10 newsletters. Make 10 videos on YouTube. Record 10 podcasts. I have found that going from 10 to a hundred is definitely a slog, and there are lots of mini milestones, but once you do something a hundred times, you’re going to build momentum on it.And you’re also going to build your own country.Nathan: [00:00:30]In this episode I talk to my long-time friend, Matt Ragland. So Matt joined ConvertKit really in the early days. He was employee number five, and he was here for the crazy ride. Then he started a YouTube channel. He led the customer experience team at another startup called Podia. He’s now as a full-time independent creator earning a living on his own.We have a really fun conversation reminiscing about the early days talking about crazy rocket ship growth, and how we kept up. We get into earning a living as a creator. How he grew his YouTube channel to 60,000 subscribers. How to choose a niche, and when you should double down on that, and what’s getting traction on YouTube.The last thing that we talk about is when, as a creator, you should quit your full-time job, and some of the nuances of that, so you can go full-time on your creative endeavor. So it’s a longer episode today because Matt and I just can’t help but tell stories.With that, let me get out of the way and dive in.Matt, thanks for joining me.Matt: [00:01:31]Oh, it’s such a pleasure. I’m thrilled to be here.Nathan: [00:01:34]I want to go back to, what year would it even be?Matt: [00:01:40]2015.Nathan: [00:01:41]2015? Okay.Matt: [00:01:44]Right around this time. Maybe a couple months later, but it was like late summer.Nathan: [00:01:49]So, it’s July, like yeah. And then July right now. Yeah, it would have been when we started talking, I’m thinking, what were you doing online around that time? Cause I started to come across you on Twitter.I think Brian Delk was a mutual friend.Is that right?Matt: [00:02:06]Yeah. Ryan Delk was a mutual friend. Brian Harris was a mutual friend. The way that we got actually directly connected is that I was on Brian’s email list. And I saw that you were doing a webinar with him to promote ConvertKit. And I had just signed up for ConvertKit as a customer, always like a little notch in the cap that I, I feel like I have of having like the three-digit user ID.Nathan: [00:02:32]Do you remember what your user ID is?Matt: [00:02:33]I used to know.Nathan: [00:02:36]In the three digits is pretty impressive.Matt: [00:02:38]Yeah. A three digit. Yeah, definitely.Nathan: [00:02:41]Now they’re well into the six digits.Matt: [00:02:43]Yeah, it’s wild. And so, I was familiar with ConvertKit. Certainly at that time it was like, okay, let me watch Nathan talk about it. What are the things that he thinks are important with it? Like some email building strategies? Because what I was really doing a lot of my online work at that time is I was doing two things.I was doing some contract work with some other SaaS companies. In terms of an audience building creator standpoint, I was doing two things. One was that I was creating the sketch notes. And so like visual, visual art of like webinars, podcasts. And that’s what I would use to teach people how to take better notes so they could remember more of what they’re doing.And it was a way to connect with other influencers because it was an attention grabbing thing. And so that was the main thing in terms of audience building and some course creation.The other thing that I was doing that paid the bills a little bit better at that time was I was also helping people set up WordPress themes and websites.At the time I would be like, oh yeah, you know, I kind of do some web development and then like, not really knowing like what all that meant. And then as I started to work more and more with actual developers, I would set up a theme online for people. But you also look at it and see that there’s still a pretty interesting intersection between like, how can you just do something relatively simple for people that either: A, they don’t have time to do, or B, they just don’t want to figure out because they just want to focus on their creative work.And so that’s what I was doing summer 2015 at the time.Nathan: [00:04:27]Yeah. So then at the time we were, I think four people, five people on the, let me count,Matt: [00:04:37]I think it was four if I remember properly,Nathan: [00:04:39]Myself, mark, David, Dan.Four. Yeah. and we were at 15,000 a month in revenue. Let’s see now I’m trying to think....

Sahil Bloom is Vice President at Altamont Capital Partners, a generalist investment fund managing over $2.5 billion in capital. At Altamont, Sahil helps lead the consumer products and services sector. Sahil also participates in board activities at Altamont’s portfolio companies Fox Racing, and Brixton.Sahil is an angel investor in over 25 tech startups. He works with entrepreneurs and founders to build scalable and sustainable value for all stakeholders. Sahil also publishes a popular newsletter about business, mental models, economics, and more.Sahil graduated from Stanford University with a bachelor’s degree in economics & sociology, and holds a master’s degree in public policy. While at Stanford, Sahil was a four-year member of the Stanford baseball team. Sahil is also a two-time recipient of the Bruce R. Cameron Memorial Award. This award honors students exhibiting excellence in athletics, academics, and leadership.In this episode, you’ll learn:How Sahil went from 500 to 200,000 followers on Twitter in one yearThe emerging seven-figure opportunity Sahil sees for localized newslettersSahil’s system for writing exceptional contentThe key difference between income-producing activities and wealth-producing activitiesLinks & ResourcesPacky McCormickMario GabrieleAnthony PomplianoFred WilsonTomas Gomeza16zFutureSynthesis SchoolHoneSequoiaBenchmarkQED InvestorsRyan HolidayNotionClayton Christensen InstitutePalletPatrick O'ShaughnessyBen ThompsonSahil’s LinksFollow Sahil on Twitter: @SahilBloomThe Curiosity ChronicleEpisode TranscriptSahil: [00:00:00]I think of writing and storytelling as foundational skills to your entire life. I mean, if you write well, it makes you better in every other area of your life. I think more clearly it exposes the gaps in your thinking so quickly. And that happened to me all on the way. Like the amount that I learned about investing by writing about investing was insane.Nathan: [00:00:27]This episode is with Sahil Bloom. So, Sahil, full-time is an investor. He’s a vice president at Altamont Capital Partners. On the side he has built a massive Twitter following over just the last year before we started the interview.I had no idea that his 200,000 plus Twitter followers have been in the last 14 months, basically since COVID.So, in this episode, we talk about growing a Twitter audience. We talk about all kinds of things. Sahil was a baseball pitcher for Stanford. And so we get into the new name/image/likeness rules for the NCAA.What else? There’s all kinds of good stuf: his creative writing process, his mental models, how he thinks about income versus wealth. It’s the kind of episode that I absolutely love some.So I’m going to get out of the way and let you listen to it. But really quick, if you’d do me a favor and go ahead and subscribe on Spotify, iTunes, wherever you listen to the podcast, and then write a review, I’d appreciate it. It will help the podcast reach a few more people.So, all right. Let’s dive in.Sahil, thanks for joining me.Sahil: [00:01:34]Yeah. Thanks for having me.Nathan: [00:01:35]Okay. So, I want to start with what you put in your bio, which is just three words, investor, educator, and storyteller. I like how concise you’ve got this down to things that describe you, but how do you think about the way that those three interact with you?Sahil: [00:01:50]You know, it’s it’s interesting. I tend to think that there is like a natural flywheel that is being created in real time around the universe of like investing, in the universe of creating. And you’re seeing it in real time with some of these, you know, creative capitalists for lack of a better way to put it.Like Packy is one of my favorite writers, does an incredible job. Mario, over at the The Generalist. A lot of these folks, I mean, Pomp was one of the early ones to do it. A lot of these folks have built these scale platforms, these audiences, and then as a result of that, and as a result of the reach and the leverage that they’re able to get on, having that kind of owned audience in a certain extent, to a certain extent, they’re able to really support these companies.And so, as an investor, as an advisor, you can kind of just create this natural flywheel around it, where your content creation and the creative work is the leading into, these really interesting investment and capitalists opportunities. And then because of those, you’re actually getting more content to write about.It actually is creating this really unique, flywheel that I think we’re really in the early days of candidly, like, we’ve seen a lot of people starting to do it, but it’s very much the first inning in my opinion. And I think there’s a massive shakeout happening in the investment world because of it.All of the VC is, and all of these growth equity funds are just starting to realize that in order to win deals, in order to be a part of these cap tables and really provide value, you know, they’ve said, how can we be helpful as like the joke moniker for a long time, but in order to really be helpful, you need to be able to do tangible things for the companies that you’re supporting and investing in.And these creator capitalists, I do feel like have figured that out and I don’t put myself in the same ranks as those people that I mentioned at all. I’m kind of very green and new to this, but, it’s been fun to start see the early fruits of that.Nathan: [00:03:42]Yeah. It’s interesting to me. Cause you’ve seen for a long time, investors like, Fred Wilson, Tomas Gomez and others, like have these blogs or newsletters, you know, for a long time. And it’s gotten them incredible deal flow and reputation and everything else, but it does seem like there’s a new wave.I don’t know if it’s just the next generation of creators doing this, but it’s much more Twitter forward rather than starting with a blog and a Twitter, a newsletter. do you see other continuations or differences between like sort of the previous generation in the second generation.Sahil: [00:04:17]Yeah. I mean, I think that the VC world has known this for a long time. like the early stage VCs in particular have known that. Audience and reach was a wedge for deal flow. And...

Charli Prangley is the Creative Director at ConvertKit. Charli has a bachelor's degree in design, with an emphasis on visual communication, from Massey University. Before working at ConvertKit, Charli worked as a designer for companies such as Mitsubishi Electric, Xero, and her own Liner Note Kids.Born in New Zealand, Charli now lives in Valencia, Spain. She is passionate about helping creatives improve their craft and process, as well as working on her own side projects. When she’s not working at ConvertKit, Charli creates weekly content on her YouTube channel and podcast, Design Life, where she shares insights about working as a professional designer, and gives tutorials and advice on design tools and concepts.In this episode, you’ll learn:How to balance your side hustle with a full-time jobHow Charli turns curiosities into money-makersWhy newsletter creators need a YouTube presenceCharli’s tips for getting more YouTube subscribersLinks & ResourcesConvertKitBasecampWebflowJohnnie GomezPalletSahil BloomThe BloomboardJessica HischeCharli’s LinksFollow Charli on Twitter: @charliprangleyWatch Charli on YouTubeDesign Life Podcast on Twitter: @DesignLifeFMDesign Life Podcast websiteCharli’s websiteEpisode TranscriptCharli: [00:00:00]I want to show people the real life of a professional designer; the projects that I work on, how I work on them, how I make decisions, the challenges that I run into along the way. That’s the kind of thing that I’m looking to share. And then that sort of lens frames all my content. Not just on YouTube; it’s also the newsletter, the book, anything I tweet, as well.It sort of all comes from this.Nathan: [00:00:31]In this episode I talk to Charli Prangley. Charli is the Creative Director at ConvertKit. She and I have actually worked together for four-and-a-half years, and during that time, well, actually before she joined ConvertKit, she’d built a popular YouTube channel about design—specifically marketing design.She’s at over 200 or right about 200,000 subscribers on YouTube, which incredible.She’s got all kinds of projects.In this episode, we dive into things about design. She and I are both designers, so we love those topics.We talk about side hustles, and how you balance that with a full-time job. Her career, moving up the ladder, becoming Creative Director at ConvertKit, and all the other things she wants to create.What gives her energy; what doesn’t.We talk about sharing things about money online, and how that can be a tough topic.She shares her income, she does videos about salary and making income from side hustles, so we talk about those details, and then we talk about as a newsletter creator, is YouTube something that you want to pursue?And tips and tricks and ideas for that.Anyway, I’ll get out of the way, and we’ll dive into the episode.Charli, thanks for joining me:Charli: [00:01:42]Yeah. Thanks having me. I’m excited—honored to be on the Nathan Berry show.Nathan: [00:01:47]That’s right. I’m glad it gets that kind of enthusiasm.Is only because we’ve worked together for so long?Charli: [00:01:59]Maybe, I don’t know, honestly, actually I’d probably more excited to be on if we hadn’t worked together for so long.Nathan: [00:02:04]That’s right. You’re actually like, “Fine, fine. I’ll come on your podcast. But to be clear, I’m doing it during works hours, and you’re paying for this.”Charli: [00:02:12]Yeah. This is a favor to you.Nathan: [00:02:14]Yeah. Whereas separately, because maybe if we hadn’t spent the last four years working together, then, then you’d actually really want to do it.All right. Well, maybe let’s start there because we have spent the last four years working together, four-and-a-half.Charli: [00:02:33]Yeah.Nathan: [00:02:33]And yeah. So coming, approaching five this fall. The first thing that I want to ask you about is how you think about all the different things that you’re doing as a creator.As I mentioned in the intro you’ve got, you know, the YouTube channel, you have a podcast, you have a newsletter and everything else.And I, I just love to hear how you think about the intersection of those things. And then we can get into the intersection of a full-time role, and all the full-time creator things.So what’s the, like Charli’s creative landscape?Charli: [00:03:06]Ooh, I like that. I would say that I’m aiming to make the kind of content that would have helped out, you know, like the me from two years ago.And that’s kind of been my approach the whole time through. So when I started, maybe I was making stuff more for beginners, and every now and then I will still, but I’m trying to like level up my audience as well as I level up in my career.And I love the term creator. I feel like it’s definitely the best way to describe me because I’m not just a YouTuber. I’m not just a podcaster, or just a blogger, or a writer, or whatever.I do all the things like wherever I feel drawn to create in whichever method I feel like will best express the thing that I’m trying to teach or share is what I lean into.Nathan: [00:03:49]Yeah. that makes sense. Uh that’s how I feel, like, you can’t put me in a box.Charli: [00:03:54]Yeah, no. How dare you.Nathan: [00:03:55]The only box that I’m willing to accept is a giant all-encompassing freeform box of creator.Charli: [00:04:01]That molds, and like, changes shape as you do. Yeah.Nathan: [00:04:04]Yeah, exactly.Okay. So you have all of these things. Maybe your most recent thing that I want to talk about is Inside Marketing or Inside Marketing Design is that marketing would be an entirely thing.We’re talking Inside Marketing and Design. I’d love to hear first, why you wanted to start that, and maybe the seed, the direction a little bit.I’ve heard you talk about like design being so focused. People either talk like graphic design, or they talk product design, you know. So, we’re like into user experience, user interface.I’m curious how marketing design fits into that and your, your desires there?Charli:

Robert Glazer is the founder and CEO of Acceleration Partners, a global marketing agency. Robert is also the co-founder and Chairman of BrandCycle, an affiliate marketing and content monetization platform.Acceleration’s accolades under Robert’s direction include Glassdoor’s Employees’ Choice Awards, Entrepreneur’s Top Company Culture, Inc. Magazine’s Best Place to Work, and Fortune’s Best Small & Medium Workplaces. Robert is also the international bestselling author of four books: Elevate, Friday Forward, Performance Partnerships, and How To Thrive In The Virtual Workplace.With a passion for helping entrepreneurs and organizations achieve success, Robert shares his insights in Friday Forward, an inspirational weekly newsletter reaching over 200,000 individuals and business leaders across 60+ countries. He is also a regular columnist for Forbes, Inc. and Entrepreneur on the subjects of performance marketing and entrepreneurship, company culture, hiring, and leadership.Robert enjoys speaking on business growth, culture, mindful transitions, building capacity and performance, and spends his spare time skiing, cycling, reading, traveling, renovating his home, and spending time with his family.In this episode, you’ll learn:The most important component for maximizing your content’s reachThe necessity of giving your audience direct access to youWhy the culture of your organization or brand is so importantLinks & ResourcesEntrepreneurs' Organization“This Is the Only Newsletter I Always Read. Here's Why”Rad ReadsFriday FourJames Clear“How a CEO’s Inspirational Emails Got a Worldwide Following”Benjamin HardyTim FerrissMalcolm GladwellDanielle SteelRobert Glazer’s LinksRobert Glazer’s websiteFriday ForwardElevate PodcastAcceleration PartnersBooks by Robert GlazerRobert’s TwitterEpisode TranscriptRobert: [00:00:00]Here’s how you should think about what is a mistake that you have permission to make: one of the things that was really helpful is we shared with the team a picture of a boat with a waterline, and said, “Look, the below-the-waterline stuff is going to sink the boat, the stuff that’s above the waterline, that’s not going to stink the ship. Let’s make mistakes, learn from them, and not make them again. What we really need you to do is watch the waterline.”Nathan: [00:00:31]In this episode, I talk to Robert Glazer, who built a newsletter called Friday Forward to a couple hundred thousand subscribers, which is really impressive.But then he also did it while running a full-time business while running a team of over 200 people. They’re growing really quickly. The company is called the Acceleration Partners, and they are an agency that works with all the biggest affiliate programs out there. So it’s fascinating the way that he took the content, the way that he republished on LinkedIn and wrote for Forbes, and, Inc., and others.We also get into other things like company culture. He runs a virtual team. We get into why he writes books and produces courses even as he’s running a multi-million dollar company. A lot of interesting things. There are questions that I’m asking kind of really for myself, because he has this interesting split of content creator and CEO, that I try to find that balance and walk that line as well.It’s a phone conversation. We've been friends for a long time and, haven’t caught up in quite a while. So, it’s just fun to chat.I hope you enjoy the episode.Bob. Welcome to the show.Robert: [00:01:34]Good to be here.Nathan: [00:01:36]So I actually haven’t talked to you in a long time. I was just thinking back to,Robert: [00:01:41]Pre-COVID probably. And then we reallyNathan: [00:01:43]Yeah, exactly. But we’ve had so many good conversations, like a few interesting things that we have in common is both running good sized firms, like as CEOs, and then also loving content creation and loving this side of it. So, I want to talk about all kinds of stuff related to that. But first, your newsletter Friday Forward, like, will you just tell high-level where that came from?Because as I understand it, you didn’t set out to start a newsletter. You set out to create content for your team.Robert: [00:02:12]Yeah, and even set out to work on my morning routine. So, I actually had come from a leadership event, pretty intensive event that Entrepreneur’s Organization had put on. I think it’s until I started a long time. And then you realize you’ve got to change your dates like five, seven years ago now.The real focus is on the morning routine, not the real focus, a big focus was on a morning routine, starting off the days. Because, you know, time for thoughtful reflection, reading something positive writing, which is a great routine for a creator anyway. And, we were given some stuff to read.It was a little too like rainbow and unicorny like, “You can do it!” quotes. Like it wasn’t my cup of tea. And so I, when I got back and I continued through the routine, I was like, you know what, maybe, maybe I’ll combine these activities. I have some stories that I like and some quotes and some things in this folder.Like, so I thought like our team was like 40 at the time, I think maybe 45 and we’re all distributed. We’ve always been virtual. And so I was like, I’ll just start writing this note to the team on Fridays. And it won’t be about our business or anything. It’ll be about a story or something kind of inspirational and motivational getting better.Started sending these things, I changed the name a few times. For a couple of months I didn’t think anyone was reading them. Then I did get some notes back saying, you know what, I did this thing, you talked about three or four weeks ago, or, “Thanks, that was really helpful.” And the other curious thing was I got notes like, “Hey, I shared this with my wife’s company,” or, you know, “My brother shared this with his family. He loves it. I’ve been sending it to him.”So, I was actually at another EO conference a couple months later talking with some other CEOs about like, this is, this has been really good. It’s been good for me. It makes me think about something, right.It’s been a great way to connect to the team. You know, you, you should all try this. And they said, Oh yeah, well, se...

Ryan Sneddon is a self-described CEO and emperor of local news. Ryan is building a hyperlocal newsletter empire one city at a time, starting with Annapolis, MD.Ryan’s newsletter, Naptown Scoop, is an email to the residents of Annapolis containing all pertinent news and events. It's an awesome community of residents and business owners coming together to be good neighbors.Ryan has worked as an editor at The Daily Thread, as a business solutions consultant at Softdocs, and as an engineer for Grand Banks Yachts. Ryan has also worked as a project engineer at The Whiting-Turner Contracting Company.Ryan studied mechanical engineering at the University of South Carolina, and also worked as a cinematographer and photographer. Ryan has done volunteer work building relationships with high school students while leading a team of other volunteers at Young Life.In this episode, you’ll learn:How Ryan stays motivated when work gets overwhelmingRyan’s philosophy and tips for interacting with your audience A great way to assess your growth and progress as a writerRyan’s proven strategies for maximizing your social media engagementLinks & ResourcesFrom BoiseAppSumoViral Loops on AppSumoJason CalacanisAnnapolis Rotaract ClubRyan Sneddon’s LinksRyan’s Twitter: @sneddymobbinNaptown ScoopEpisode TranscriptRyan: [00:00:00]First advice would just be to “get started.” Second advice would be, “don’t quit,” every day. Third advice (this is not specific to a local newsletter. I would say this to any newsletter, any brand, anyone ever) just be responsive.The great thing about an email newsletter is that people can answer it: I can reply to an email cause it’s just a regular email. Answer every single one of those, because that’s how you build up a loyalty.Nathan: [00:00:30]In this episode I talk to Ryan Sneddon who runs Naptown Scoop, which is a local newsletter for the Annapolis region. I like it because I started a local newsletter called Boise, to just about a thousand subscribers. And, you know, Ryan and I were chatting back and forth on Twitter, just saying like, what ideas are we learning from each other?He was giving me some advice and I was like, you know, I why don’t you just come on the podcast and share the story, share what you’re doing.It’s pretty fun how it’s coming together. He’s working super, super hard on it, and we dive into all the details. So with that, I’ll get out of the way.Ryan, thanks for joining me.Ryan: [00:01:09]My pleasure.Nathan: [00:01:10]So give us the 30-second pitch. What’s the newsletter, and then from there, we’ll dive into, “Why start a local newsletter?”Ryan: [00:01:18]My newsletter is called an Naptown scoop and the 30-second pitch; I could really do it in 10 seconds. It’s just everything you need to know about the town delivered straight to your inbox three times a week. And I would do it more if it were a bigger city, do it less if it were a smaller city, but that’s just kind of the perfect number of times that gets you all the information, but it’s not too much.Nathan: [00:01:40]Yeah, that sounds good. So what was the inspiration to start it?Ryan: [00:01:43]There’s another company. I mean, there’s a couple of companies now that are out there doing this, but I lived in Columbia, South Carolina after college. I went to college there and stayed a little bit extra. And there was a company there that did it and I really liked it. And then I moved away back here to home, and I didn’t have that.And I was like, well, that was cool. I can’t be the only one that liked that. So I was like, I’ll just build it here. And, I wasn’t the only one that liked it. We were talking before we started recording. There’s not really a good original ideas in my head. So the fact that I wanted it was a good sign, because if I wanted it other people probably do, too.Nathan: [00:02:17]Yeah, that makes sense. I am fascinated by local newsletters. I started one on my own called From Boise.Ryan: [00:02:27]I get it; you got to see what everyone else is doing and your same space.Nathan: [00:02:31]Got to get some ideas. I saw Andrew Wilkinson do it in Victoria, British Columbia, which is one of my favorite cities to visit. And so I saw him do that and I was like, oh, well I love Boise as much as he loves Victoria, and wanted to do some local projects. So, so, it’s been fun, but maybe before we dive into the growth and all of that, what are some of the favorite moments from running it where you’re like, “Oh, this is actually pretty sweet?”Ryan: [00:02:59]There’s a lot. One just happened last week. I think it was, it’s been like a really long, last two weeks; has been a really super full and, I don’t use the “B” word. I don’t say “busy.” I’m not allowed to, but it’s been like a really full on hundred miles an hour, 20 hours a day, kind of lasts two weeks now.Like sometimes—no joke—sometimes more than that. But last Thursday night I was delivering cookies to people who bought shirts, because I made some shirts to sell for the brand. And I said I was going to deliver cookies to the first or 10 out of the first hundred orders, which was like super ambitious of me.I didn’t even think about the fact that like, I would have to sell a hundred shirts for that to happen. and I only sold 10 shirts. So I delivered the 10 cookies to the first 10 people instead of 10 out of the first hundred. But I’m delivering cookies to this one, and I just emailed everybody and said, if you’re not home, can I leave it in the mailbox?And they were like, yeah, our mailbox is a giant stone pillar at the front of the driveway. And I was like, giant stone pillar? Like, this is probably a pretty nice house. And so I put in the GPS and I’m like, oh yeah, this is a waterfront looking pretty good. I roll up to the house and it’s gorgeous.It’s probably like this three to $4 million house. I can look at it and kind of think I know who the architect is, because she’s pretty famous around the area. And as I’m putting these cookies in the giant mailbox, they roll up and they like the car honks, and they roll down the window. It was an Uber, they rolled out of the back windows and they’re like, “You must be Ryan!”And I was like, “Yeah!” And they were like, “Do you have time to come in for a drink?” And I’m like, “Yeah, why not?” it’s 9:45 at night. No, it wasn’t, it wasn’t a Thursday. I think it was a Wednesday because if it was Thursday, I would have had to go home and write the email for Friday. But since it was Wednesday, I didn’t have to get one out to the next day.So I was like, “Yeah, I have time for a drink!” And I ended up sitting on their back porch for two hours, drinking wine, just talking about their life, my life, the business, the guy, it was just the ...

Cherie Hu is an accomplished musician, an award-winning writer, a columnist, entrepreneur, and self-described “professional overthinker.” Cherie specializes in analyzing, tracking and critiquing innovation in the global music business.Cherie earned her bachelor’s degree in statistics from Harvard, studied piano and music theory at The Juilliard School, and has taught as an Adjunct Professor at New York University. Cherie has worked for Forbes, Billboard, and Music Business Worldwide.Cherie is also the founder of Water & Music. Water & Music is an independent newsletter, research hub and community forum that is “dedicated to unpacking the fine print of commercial, technological and cultural change in the industry.”The Water & Music newsletter reaches over 10,000 free subscribers and 1,000 paying members. Subscribers represent numerous industries: music, film, fashion, advertising, gaming, investment banking, venture capital and more.In this episode, you’ll learn:How to leverage your life experience to dramatically improve your newsletter  Why freelance writers should focus on a core group of clientsWhy your audience needs a dedicated venue to find your contentLinks & ResourcesZack GreenburgForbesBillboardMusic Business WorldwideRevueGreg IsenbergKendrick Lamar Meets Quincy Jones on HypebeastConvertKit Creator SessionsSpotify GreenroomTwitter SpacesTim McGrawArnold Schwarzenegger’s newsletterCherie’s LinksCherie’s Twitter Page: @cheriehu42Water & MusicWater & Music on Twitter: @water_and_musicWater & Music on PatreonCherie’s LinkedIn“Five Lessons From My First Year of Running a Patreon Page”Episode TranscriptCherie: [00:00:00]A 2015 interview between Kendrick Lamar and Quincy Jones, and Quincy Jones says the last two things to leave this planet will be Water and Music. I was just watching, and I heard that and it just immediately clicked with me. It’s been called a universal language for a reason. I liked that concept of always having that at the center, even of conversations about the business side.Nathan: [00:00:30]In this episode, I talked to Cherie Hu. Cherie is an entrepreneur journalist writer, and she writes about the intersection between music and technology. She has this popular newsletter in a community called Water & Music. We have a lot of fun talking about how she grew the newsletter, her journey from piano performance, through to math and then into journalism. We spend a lot of time in this episode on some trends in the industry, not just, crypto and things like that, but also, Spotify and podcasts, and how the world of music and podcasts and newsletters is all intertwined. It’s a fun episode.There’s a little less hard hitting tactics of, “Do this next to the newsletter,” and a lot more on: this is what’s going on in the industry and what you should pay attention to.Those are some of my favorite episodes, and this one is pretty great. So let’s dive in.Cherie. Thanks for joining me.Cherie: [00:01:25]Thank you so much for having me, excited to be here.Nathan: [00:01:27]All right. So I want to start with your love for music and the music industry. Where did that come from? You went to Juilliard for piano performance. Tell me more about it.Cherie: [00:01:41]Yeah, sure. Yeah. It almost feels like a past life at this point. Right? I guess to be more specific about that, I did the Juilliard pre-college program. It’s like a weekend program out of conservatory. And did that throughout high school where I would go to Juilliard, to the city on Saturdays, do private lessons, have classes in music theory, chamber music.And that, that was my path for a while, to just go to conservatory for piano and study that, and be a full-time performing pianist ideally. Very, very different from what I do now, but, still very near and dear to me. A lot of my closest friends, I kind of made in that environment, very intense, but fun environment.So, I guess my first and most intense involvement growing up with music was definitely on the performing and on the creative. At the same time academically, I was really into math and I was on the math team, did math competitions in school. I ended up majoring in stats in college, taking a lot of math and stats classes, but at the same time, a lot of music classes, and from a very early stag, trying to think about where those two worlds intersected.So, because I was more like a performer initially, I was thinking, applying math to music theory. I think that’s still a really interesting like application area. I guess also in spite of learning, studying piano for 10 to 15 years, I wasn’t even aware of the scope of what the music industry involved in terms of the jobs that were possible, the new kinds of jobs that were emerging, until I would say 2013, 2014.That’s when I had the opportunity just to explore, this career path, to do a two week, two to three weeks shadowing experience at Interscope. It was with their A&R team. In terms of like actual like tasks, I didn’t do that much because it was a short amount of time, but just that experience opened my mind, even to things like, like real questions, like what is A&R?I didn’t really know what that was before, being in the middle of it. And also at that time streaming had been around for a while, but I think that period of time was really when Spotify had just launched in the U S, and it’s really starting to pick up; Apple music with launch just a year or two later.So, the whole conversation around like who the main players were in streaming was also changing pretty drastically at that time. So, timing also plays a huge role in my journey to where I got to now. So, it’s kind of through that. I realized I was interested in maybe applying like my academic interests on the staff side to more of a data analyst, or data-facing role in the music industry, whether that’s at a label streaming service, music startup, et cetera. So, did a handful of internships kind of in that world, did some academic research on the music business from a tech perspective.So, especially looking at music, startups, and I’m super randomly at a career fair that my friend dragged me to, I very serendipitously read into my first freelance gig. I happened to meet an e...

Jack Butcher is the founder of Visualize Value, a design, consulting, and educational company in New York City.Jack spent 10 years working in advertising for Fortune 100 companies as a creative director for multi-billion dollar brands that include Amazon, Nokia, McDonald’s, and Mercedes-Benz. It was a job he found enjoyable but constraining.In search of freedom, Jack started his own advertising agency, which he describes as “No fun, and even less freedom.” However, after two years of iteration, Jack figured out how to transition to highly specialized (and fun) consulting, and a product business that scales infinitely.Visualize Value is the product of that transition, a project Jack has used to build a network of mentors, a $1M/year product business, and a media platform with an audience of over 500,000 people.In this episode, you’ll learn:How to use your unique skills to stand out on social mediaWhy repetition in your design is the fastest way to build your brandHow designing for niche markets makes your job much easierHow to scale your business without compromising qualityLinks & ResourcesDHH on Twitter: @dhhJason Fried on Twitter: @jasonfriedBasecampNick Huber on Twitter: @sweatystartupDavid Perell on Twitter: @david_perellWrite of PassageBrian Norgard on Twitter: @BrianNorgardAnthony Pompliano on Twitter: @APomplianoMaven AdviserJack Butcher’s LinksJack’s website: Visualize ValueJack’s email newsletter: VV/155Jack’s Twitter: @jackbutcherVisualize Value merchandiseVisualize Value on Twitter: @visualizevalueJack’s Instagram: @jckbtchrVisualize Value on Instagram: @visualizevalue Build Once, Sell TwiceEpisode TranscriptJack: [00:00:00]You build something digital that runs on code or media, and can be served up infinitely at zero cost replication to you, something like a product or an information product you build at once, and you can sell it to a hundred, a thousand, 10,000, a hundred thousand people. The bulk of the value is created once.And then just becomes a game of how effective are you at spreading that story and reaching people that need the thing that you’ve done. Nathan: [00:00:37]In this episode, I talk to Jack Butcher. Jack has a really interesting visual style where he’s taking these complex concepts: it could be leverage, it could be this idea of build once, sell twice (that I’m super jealous of by the way), how he framed that… any of these things, he takes them and distills them down to these graphics:Black background, white text, white line drawings, slightly pixelated looking. It’s very distinct style and he’s used it to build a massive following; well-over a hundred thousand followers in social media, he built his email list, he’s doing fantastic revenue from courses. So, we dive in on what it takes to be unique.How a lot of marketing Twitter, you know, marketers talking about marketing is repetitive. A lot of people don’t have a unique angle on it. And so how he makes unique content that’s more interesting and engaging and stands out.How constraints really drive that.We talk about a lot of other things, exactly how he makes money and monetization. There’s a lot of great stuff, who inspires him, so much more. Jack’s someone that I’ve wanted to have on this show since I started it. And so I’m very excited to talk to Jack. Let’s dive in. Jack, thanks for talking with me today.Jack: [00:01:49]Thank you for having me, man. I appreciate it. Nathan: [00:01:51]Okay. I feel like so many people on the internet are—especially in the content marketing audience growth space—are doing the exact same thing as other people, you know, it’s just like, it’s similar playbook. Everyone’s going over it repeatedly. The amazing thing is that it still works. You don’t actually have to innovate that much to make like a hundred grand a year or more on the internet, which is mind blowing, but then you come out and you actually have like a really unique visual style.You’re doing something different instead of just like another random tweet thread, or like summarizing the same quotes that everyone else is doing. It feels like you’re doing something unique. And in, you know, in these little graphics, you’re explaining these same concepts that everyone else has talked about, but in a really condensed format.So, I’m curious, well, one, let’s just start with where that came from, and then I want to get into like what you think other people should do to differentiate and not be the same. Like, you know, it’s just copying everybody else.Jack: [00:02:52]Yeah, sure, so very quick background. I studied design in school, graduated in 2010. That was in the UK. I moved to New York and started working agency jobs in basically every different capacity. So design art direction, creative direction, worked for small boutique agencies that would build like, small brands to big global behemoths at work on like.Multinational billion dollar brand campaigns. And one of the skills, one of the skills I built up, I think, across all of those experiences was working on pitch decks. So what all of these different ad agencies have in common is you have to tell compelling stories to get the opportunity to work on a project.But the pitch deck is kind of a work in the agency, right? Nobody wants to be the last one in work on the pitch deck, waiting for everybody’s emails to say include this, include this. So, early in my career I sort of got stuck with that by default, but for whatever reason, not quite into it quite, enjoyed the process of distilling all of these different people’s ideas that would come at you from all different parts of an agency or trying to convey something to a business.Basically tell their story back to them in a more compelling way than they’ve ever heard it told. And that’s essentially what gets you the opportunity to work on these projects? So, yeah, a lot of late nights working on pitch decks was the, I think the eventual catalyst for visualized value as a style, I went through a ton of iterations to get there.Worked at agencies for eight years, started my own agency and then slowly narrowed down the type of work I was doing as an agency to that really, , specific aesthetic and that very specific deliverable. So before visualize value was a media company, it was a very hig...

Alex Lieberman is the co-founder and chairman of Morning Brew. Morning Brew is a media company bringing informative and digestible business news to your inbox every morning. They educate nearly 3,000,000 daily readers on the latest news from Wall Street to Silicon Valley.Alex also hosts The Founder’s Journal Podcast where he gives listeners a “backstage pass” into building Morning Brew, and in turn, helps them build a better business or career.Morning Brew is considered to be the largest email newsletter on the web. Business Insider recently acquired a major stake in Morning Brew at a rumored valuation of over 75 million dollars. In this episode, you’ll learn:The foundations for building a great media brandWhat methods and metrics work best for rapid subscriber growthHow to optimize a referral program to gain explosive growthHow to be the leader your employees need as you scaleLinks & ResourcesBusiness InsiderKara Goldin’s LinkedIn pageHint WaterPat FlynnPat Flynn: Why I Switched from AWeber to Infusionsoft to ConvertKitKickoffLabsViral LoopsRobinhoodTim FerrissHarry’s RazorsLenny RachitskyPacky McCormickGuest’s LinksAlex’s LinkedIn pageMorning BrewFounder’s Journal podcastMorning Brew Accelerator (MB/A)Alex’s Twitter: @businessbaristaEpisode TranscriptAlex: [00:00:00]That’s the beautiful thing about just business in general, this diversity of what brings people joy. People who love building process and planning who have a foundation and building on top of that foundation. You have people who have zero foundation. They want to prove to the world and prove to themselves that the crazy thing that’s been in their head that they think is valuable, there’s no proof of yet, that the actually people will love it.Nathan: [00:00:30]In today’s episode, I talked to Alex Lieberman, who is the co-founder, and now chairman—formerly CEO—and now chairman of Morning Brew. They grew the newsletter to over 3 million subscribers, which is insane. Making it the largest email newsletter on the web. So if we’re talking about newsletters on this podcast who better to talk to than Alex.We get into why he transitioned from CEO to chairman. We talk about the exit: they sold a majority of the company to Business Insider rumored at over a $75 million valuation, which is really, really impressive. One of the things we talk about the channels that drove growth, their affiliate program, the referral program that so many people talk about and reference, what works, what doesn’t.We get his take on sponsorships versus paid content, details on the type of ads that they used in their paid acquisition when they were growing Morning Brew, so much.Anyway, there’s a lot of good stuff. I’ll get out of the way. Let’s dive in.Alex, thanks for joining me.Alex: [00:01:32]Thanks so much for having me, pumped to do this.Nathan: [00:01:34]All right. So I want to start with, your role has shifted. You just moved from CEO of Morning Brew to chairman. And tell me a little bit about that.What, what instigated it. What made it time for that move? I know a lot of people who have run companies for years consider a move like that.Alex: [00:01:52]There’s many months in the making. and I think in a lot of ways, the last year has kind of been like a unspoken transition, based on just the things that I was spending my time on and the things my co-founder Austin was spending his time on. You know, I think the, the way that I think about it is I loved—I’ve loved every part of Morning Brew, but like the things that have really given me energy is when I am building things from scratch, I love building things from scratch.And that’s what I was able to do in, in the early days of the Brew, you know, our original newsletter, our B2B newsletters, our podcasts, like really creating the foundation for something that could obviously become a large media brand. As we’ve scaled, obviously like, you know, you’ve, I’m sure experienced this in your role, the roles of a CEO change 50 different times.And so the way, you know, the way I think about it is the first role that I had at Morning Brew was every role Austin. And I had every role. I always tended to lean more towards sales, marketing, and content, like more the creative and people facing side of the business. Austin always, spend more time on growth product, and like the finance, the finances of the business.And so I wore many different hats and I loved doing those things. And then as we started to grow, as we got the flywheel going of creating great newsletter content, attracting audience and monetizing our audience through advertising. My role shifted. And I went from a hundred percent doing to what I would say is like 50% doing, and 50% managing.And I really enjoyed managing, like I loved, I loved coaching people, supporting people, but what I also learned pretty early on in Morning Brew is that managing there, there were aspects of managing that I loved, and there are many aspects of managing that I didn’t love. The way I think about managing is I think there’s two aspects to managing there’s call it like leadership and there’s operational management, operational management, really being about.Like goal setting, metric checking, and making sure that you’re holding someone accountable to continuing to do the job they’re supposed to do really important job for a manager. Then on the flip side, I would say the leadership side of managing is kind of the empathetic management part, which is how do you support someone in their career growth?How do you talk to someone about the things that are impacting them in their job performance, whether it’s things within their career or things in their personal life that are coming into their career, because that inevitably obviously happens as well. And what I realized is I really loved the second thing.I didn’t necessarily really loved the first thing. The reason I bring that up is because as we’ve scaled as Morning Brew, let’s say got to 50 people and. And at 50 people, we really, that was the point in time when we had to go from bein...

Eric Jorgenson is a writer, course creator, blogger, and podcaster. He is also on the founding team of Zaarly, an online marketplace for hiring home service providers.Eric has been publishing online since 2014, and operates a monthly newsletter. His business blog, Evergreen, has educated and entertained over a million readers.Eric is the author of The Almanack of Naval Ravikant: A Guide to Wealth and Happiness. Naval Ravikant is an entrepreneur, philosopher, and investor. Naval's principles for building wealth and creating long-term happiness have captivated the world.The Almanack of Naval Ravikant is a collection of Naval’s wisdom and experience from the last ten years. It's a curation of his most insightful interviews and poignant reflections.Eric’s current project, Building a Mountain of Levers, teaches “how to accomplish superhuman feats by playing a different game — building leverage.”In this episode, you’ll learn:The most important things to do when starting a newsletterWhat leverage is, and how to use it to exponentially scale your businessHow a random tweet blossomed into Eric’s best-selling bookLinks & ResourcesThe Almanack of Naval RavikantNaval Ravikant’s podcast@FAKEGRIMLOCKBen CaballeroReworkAnything You Want: 40 Lessons for a New Kind of EntrepreneurPeter BevelinPoor Charlie's Almanack: The Wit and Wisdom of Charles T MungerBerkshire Hathaway Letters to ShareholdersEric Jorgenson’s LinksEric’s website: ejorgenson.comTwitter: @EricJorgensonEpisode TranscriptEric: [00:00:00]Munger said the best thing a human being can do is to help someone else to know more. Everyone has something to teach. Everyone can participate as a student and as a teacher at different points in their lives. There’s always somebody who’s one step ahead of you to learn from, and always somebody who’s one step behind you that you can help.I think counseling and learning keeps us humble and keeps life exciting. Teaching is rewarding. The fact that we can all kind of be a part of it is really fun.Nathan: [00:00:29]In this episode, I talked to Eric Jorgensen, who is the author of one of my favorite books. It’s actually the book that I have gifted the most recently, and that is The Almanack of Naval Ravikant, which is a distillation of the wisdom writing podcast episodes of Naval. So Eric did this awesome project where you compile all this edited down into a book.And I know we talked about that at the end of the episode, but throughout the episode, we talk about online education, leverage—we spend a lot of time talking about leverage—which is sort of this thing that Naval has really made the centerpiece to a lot of his content that he’s produced.Eric has gone even further and produced a course on and talked about so much great stuff. Really important concepts that I think you’re really gonna enjoy. So I’ll get out of the way and we’ll just dive in.Eric, thanks for joining me.Eric: [00:01:18]Thanks for having me. You’re on like the Mount Rushmore of heroes of like bootstrappers, turned content creators, turned bootstrappers. So like I’m super excited to be talking to you in any context. This is going to be fun.Nathan: [00:01:30]Well, good. And now, now I’m curious who else is on Mount Rushmore?Eric: [00:01:33]I knew you were going to ask me that. And I don’t, I, I don’t know. I have not prepared for it, but we can start Photoshopping it up later.Nathan: [00:01:41]Yeah, exactly. That’d be a really good use of both of our time.Reading through all of your stuff online, you are obsessed with education, specifically online education. You’ve got Course Correctly where you’re like reviewing online courses with a friend of yours.You’ve got like there’s a lot going on and you truly care a lot about the details of online education, and I’m curious, like why, where does that come from? Where does the interest turn into obsession?Eric: [00:02:12]So long-term I think like going to Mars is awesome, and curing cancer is awesome, and like solving world hunger is awesome. But education is the variable with the biggest coefficient into all of those things over the long term. So, like all of us who are alive right now are kind of like, Oh God, we’ve got to solve all these problems that are like affecting us.But if we just kind of look at the species over like a few hundred years or a few thousand years, like our ability to educate ourselves. And then the next generation is like a huge, huge, heavily weighted variable. I guess into like the outcome that we achieve over a long period of time and like how we can affect that.And I think like there’s no, you know, the, the first principles kind of like where’s the laws of physics limitedness is like, we have the ability to be so much better at education than we are, and we are. There’s some specific context where we’re incredible educators. Like our doctors are incredibly well-educated; the rigor of like a pilot’s education or doctor’s education compared to, you know, somebody who maybe like a writer, like different creative pursuits or do an MBA, like is just, we’re just missing easy opportunities to kind to become significantly better.And the internet lowers the cost of that and increases the accessibility of it. And so I think we’re going to see like a really kind of cool transformation of that over our lifetimes. I was excited to kind of see it, see it come together.Nathan: [00:03:40]Yeah. So what I hear in that is there’s individual pursuits, you know, that will like advanced civilization. You know, in like one very specific and highly effective area, but then education is like the rising tide for everything of like, if you can help people teach well, you know, learn well, any of those things and make those, those tools and Content, everything available, then that can go in any, any, and every direction.Eric: [00:04:09]Yeah. Yeah. I mean, like Munger said, like the best thing that human being can do is to like help someone else to know more. And I think that’s a really, like everyone has something to teach and. We are all trying to learn. And, it’s something that everyone can participate in as a student and as a teacher at different points in their lives.And there’s always somebody who’s like one s...

Steph Smith is a growth marketer, writer, and indie maker. In 2019, Steph founded Integral Labs. Integral Labs supports top tech companies with technical writing, content strategy, marketing, and analytics.In 2020, Steph became the Senior Manger of Trends.co. Trends identifies emerging patterns in business months before they become mainstream. In less than a year, Steph grew the number of paying subscribers by more than 400%.In this episode, Nathan and Steph discuss her proven approach to starting and running a profitable newsletter. They cover everything from pricing models to avoiding burnout.Topics from the show include:How to price your newsletter for explosive growthThe best pricing model for dramatically reducing churnHow to make your newsletter stand head and shoulders above the restLinks & ResourcesTrends.coTheHustle.coSam Parr Twitter030: Sam Parr – Growing to 2M Subscribers and Selling Your NewsletterWolfram AlphaahrefsJungleScoutKeywords EverywhereMy First Million PodcastToptal3-2-1 NewsletterExponential ViewGuest’s LinksPersonal site: stephsmith.ioSteph’s Twitter: @stephsmithioEpisode TranscriptSteph: [00:00:00]Once you actually take the energy to write an idea down and it’s implanted into your brain, almost like a seed, it starts to grow and you start to notice other things around you that are aligned with watering that seed with different examples, with intentional research, with data, by the time you actually want to write about it or publish it, or even start a business around it, you’ve thought about it in many different ways and giving it time to breathe.Nathan: [00:00:28]Today’s episode has been Steph Smith who runs trends.co, which is the paid newsletter from The Hustle. So, they have their 2 million subscribers newsletter and they have their paid newsletter called Trends, which is a little smaller, but drives a ton of revenue. This is super interesting. We get into her approach to growth, to research, she’s actually a chemical engineer who turned into this whole world. So, it’s super fascinating; she’s got a bunch of tips and tricks that she shares around doing research. I love her thoughts on differentiating products. There’s so much more; she gets into business models, everything. She’s one of those people who’s basically running the show at one of the largest paid newsletters. She’s incredible. So anyway, I’ll get out of the way let’s dive in and, made stuff.Steph. Thanks for joining me.Steph: [00:01:17]Yeah. Thanks for having me.Nathan: [00:01:18]Okay. So I’ve got to start with the question. what’s it like working for a crazy person and specifically, how are you so good at managing up? And before you answer this question, did in fact come from the crazy person that we’re talking about?Steph: [00:01:34]I didn’t see that question.Nathan: [00:01:37]And he’s like, Oh, I don’t know.But you got to find out like how, how she manages to deal on a day-to-day basis.Steph: [00:01:44]Well, I think we all are on a spectrum of being so good at executing. Some people are great at executing, and logistics, and processes and all that stuff. And some people are just visionaries and just have so many ideas and it’s crazy to work with them, but in a great way. If you can just give them the space to like, be that visionary and not necessarily depend on them for certain things like processes and logistics.And so I’ve just learned over time to not necessarily bucket people, but understand what they’re great at and maybe what they’re not so great at. And Sam loves hiring operators. And he he’s hired CEOs or presidents to work alongside him. So I actually think one of the great things about working with Sam is how self self-aware he is because sometimes visionaries or people who are like the idea guy don’t realize that perhaps they’re not so great at some of the other things.And so I just like to give Sam the space to give his ideas and be the visionary. And it’s funny. Cause sometimes when people first start working with Sam, they’re like, Oh my God, he has so many ideas. Do I have to do all this stuff? And Sam will tell you like, no, don’t do all the things I say.I just love sharing these ideas and getting things out there, but you have to decide what’s important, what should be prioritized. And so I do think it was a little bit of a learning curve, but now I love working with him because he does actually just give you the trust to make those decisions.Nathan: [00:03:03]Yeah, that’s interesting. I think so many people run into that and I’ve had the same thing with our team at ConvertKit where people are like, Okay, you said this, does this mean I need to start working on it? And you’re like, no, no,Steph: [00:03:14]Yeah.Nathan: [00:03:14]I was just talking and I’m not even as wild and crazy as Sam is on that spectrum. Sam’s off the charts, but it is a good differentiation.And maybe I shouldn’t be more extreme that way people would know that it’s not humanly possible to do all the ideas and to just ignore most of them.Steph: [00:03:32]Well, I mean, Sam will tell you, like right away that he’s just throwing ideas out there. And I think that’s really great because you’re just like, okay, so we’re on the same page. I know how much of this I need to pay attention to. And then he will explicitly say, which I think is also helpful, when he does want you to do something, versus some bosses or some people you work with, it is a little more muddy and it’s hard to tell what’s important. What’s not.Nathan: [00:03:56]Yeah. That makes sense. Another thing that Sam was talking about that he wanted you to share more with listeners is, your process around organization and creativity. I imagine at The Hustle, there’s so much going on. There’s tons of content going into the newsletter side, that Trends side, everything.And, I’d love to hear more about your process for keeping all that straight, making sure you’ve got nonstop deadlines, crazy ideas. And what do you use for organization? Like maybe somewhat on tools, but even more so like.Steph: [00:04:36]Yeah. So I think so I will candidly say that on that spectrum where there’s people who are like incredible executor’s and organizers, I’m maybe a little further ...

Nat Eliason is the founder of Growth Machine, a successful SEO and content marketing agency. Nat also teaches the popular Roam course, Effortless Output.Nat earned his B.A. in Philosophy from Carnegie Mellon University, and has worked for companies such as Zapier, and Sumo Group. Nat co-hosts the Made You Think podcast with Neil Soni.Nat also writes a weekly newsletter called Monday Medley. Each Monday Medley has ten articles, videos, discussions, pieces of research, or other interesting finds from around the Internet, spanning a broad range of topics.In this episode Nat discusses the evolution of his newsletter. He shares his strategies on developing online courses. He also explains how to find product-market fit before launching a course or product.Highlights of the conversation include:How Nat made $300,000 from his online courseWhat separates a mediocre newsletter from a great newsletterThe differences between running a newsletter and teaching a courseHow Nat balances work, family, and leisureLinks & ResourcesShane ParrishFarnham Street Sunday Brain Food newsletterTim FerrissFive Bullet FridayAzeem AzharExponential ViewairrBuilding a Second BrainTiago ForteWes BosDerek SiversNat Eliason’s LinksEffortless Output with RoamNat’s TwitterNat’s websiteThe Monday MedleyMade You Think podcastEpisode TranscriptNat: [00:00:00]Build up little channels. There’s a lot to be said for having one thing that drives 10 grand a month. But if you’ve got 20 little things that drive $500 a month, that’s cool too. In some ways it’s a little more resilient because if one fails, you’ve only lost 5% of your revenue versus if the $10,000 a month thing fails, you’ve lost all of your revenue.Nathan: [00:00:26]In this episode, I talked to Nat Eliason. We talk about a bunch of different things ranging from his newsletter, the course that he’s running, you know, earning a crazy amount of money from the course, his thoughts on paid newsletters versus courses. Really just how he approaches life. It’s kind of a meandering episode as we go through those details.I love the way that he’s not trying to grow and optimize everything. And then also the way that he’s taking internet money and bringing it into like tangible, real world life experiences, connection with friends, things like that. So it’s a great episode. I hope you enjoy it. And, actually before we dive in, I’d love for two things.One, if you’re listening to the podcast and you just clicked through from random clips or things like that, and you haven’t subscribed, go ahead and subscribe in iTunes, Spotify, and, you know, wherever you listen to podcasts, really appreciate that. And then the other thing is, I realized I’ve never actually asked for reviews and it turns out reviews help, you know, with rankings and more people to discover the show.So I would love it if you would go on iTunes in particular. Is iTunes a thing? Apple podcasts, I guess you go on Apple podcasts in particular and subscribe and then write a review or just a rating. That’ll help more people discover the show. So thanks for doing that. And let’s dive into the interview.Alright, Nat, thanks for joining me.Nat: [00:01:40]Yeah. Thanks for having me, excited to be here.Nathan: [00:01:41]Why don’t you just kick things off by talking a little bit about the newsletter that you have, and I’m actually curious, you know, how long ago you started.Nat: [00:01:51]Yes. So my name is Nat. Hi, in the world of newsletters, I started my newsletter, which is called the Monday Medley or often just the Medley in may of 2015, no 2016.Nathan: [00:02:08]Either way it’s been awhile.Nat: [00:02:10]Yeah, it must be only 2016, cause I’m coming up on five years next week. I think it’s next Monday is the five-year anniversary.So, I’ve been sending it out every single Monday for five years straight, which is kind of absurd. I actually, I have no idea how I haven’t messed one up in that time, but here we are.Nathan: [00:02:34]At 200, what was that, 260 weeks?Nat: [00:02:37]Yeah, it would be what, 260? Yeah, three times five. So it’s a lot of newsletters.Nathan: [00:02:42]That is. So what made you start the newsletter? Were there particular people you were following? And you’re like, “Oh, I want to be like them.” Or was it solving a business problem for you?Nat: [00:02:52]Yeah. So I was originally following sort of the standard advice of emailing every time an article came out. And that was working fine. And this was for my personal site NatEliason.com. and I was emailing for every article, but it’s like too many emails. Cause I was writing like a couple of posts a week back then, and I didn’t like having to like write a specific email for each article. And it felt like there wasn’t that much like extra value with being on the newsletter besides getting updates on posts, which people can do if they were just like on Feedly and subscribe to the RSS feed or whatever.So, I saw Shane Parrish start his, brain food kind of newsletter for Farnam Street. And, Tim Ferris had launched his like Five Bullet Friday, around that time too. So the Medley started as very similar to those two where it was like, you know, here’s like something interesting. I read this week. Here’s like a video I enjoyed just kind of like a little, link dump.And it was kind of that way for two or three years probably. And then it transitioned into kind of a different vibe where I got a lot of inspiration from Azeem Azhar and his Exponential View newsletter, which is like really, really good. And I just loved how, like, he wasn’t really just sharing stuff that he found interesting.He was kind of like going in depth on each thing. And what I liked about his was I felt like a lot of the link dumpy newsletters were, they didn’t feel very like high effort or very high value. And it was just like, okay, like, here’s kind of like a dump of things, but you can kind of get that from Twitter or elsewhere, plus like everyone was doing it right.It wasn’t that special anymore. So I was trying to think of how I can make it higher value. Azeem’s was such a great model because he was like going into detail on each thing. So I shifted in that direction first, where it was like, okay, here’s, you know, five, six, seven things from this week that are interesting.They’re kind of lik...

Ann Handley is the founder and Chief Content Officer for MarketingProfs, a marketing and training education company with more than 600,000 subscribers. She is a well-known public speaker, and has been writing a newsletter called Total Annarchy for the last three years.Ann is also a Wall Street Journal best-selling author of Everybody Writes: Your Go-To Guide to Creating Ridiculously Good Content, and Content Rules: How to Create Killer Blogs, Podcasts, Videos, Ebooks, Webinars (and More) That Engage Customers and Ignite Your Business. Ann was named a top thought leader by Forbes and one of the seven people shaping modern marketing by IBM.In this episode, Nathan and Ann discuss: - Tiny-house offices - How to connect with your audience and grow your email newsletter - How to grow your social media following by mastering the algorithmsLinks & ResourcesJeremiah OwyangNat EliasonJames KellerClickZFanBridgeRallyAnn Handley’s LinksMarketingProfsPersonal site: annhandley.comAnn’s Newsletter: Total AnnarchyTwitter: @annhandleyEpisode TranscriptAnn: [00:00:00] The notion of voice is essentially how you sound. It’s important to read things out loud. It’s a thousand little choices that you make all along the way that over time, grow your voice and add up to something that’s wholly unique. Find those small moments. Those small moments are the things that become a big differentiation for yourself. Nathan: [00:00:27] In this episode, I talked to Ann Handley. Ann is the Chief Content Officer for MarketingProfs. She’s been around the content marketing online business space for a long time, since 1999. She’s been writing a newsletter for the last three years on a lot of really interesting things. She’s also a really well-known public speaker.So in this episode, we talk about a whole range of things like what she thinks of the multiple rises of email newsletters over the years. The trend email is dead. The balance between email and social media platforms. We get into algorithms. We talk about really a whole range of things. Probably my favorite is when we get into talking about style and voice and how you write, how to make things fun. Her newsletter is called Total Annarchy.Annarchy, it’s spelled like her name. And so you can see if that gives you an idea of the way she likes to write, the energy and passion that she brings to a business and marketing topics. So, anyway, with that, I’ll get out of the way and let’s dive into the show.Ann thanks for joining me.Ann: [00:01:28] I am delighted to be here. Thank you for having me.Nathan: [00:01:30] So I want to start with something that has nothing to do with email newsletters, and it is just a shared love that you and I both have that I discovered in research and that is for tiny house offices.Ann: [00:01:41] Oh, really?Nathan: [00:01:43] Yeah, so I’m in my tiny house office that I built a year ago. I got it finished just before COVID which was good timing. If I understand correctly, you had a tiny house office built, like six or seven years ago.Ann: [00:01:55] Yeah, this is it. Yes. I was, it was, turned out to be a prescient move because who knew? This is very, so I’m in my tiny house office right now. It’s in my backyard. and yes, I built it, oh, six or sevenish years ago, something like that. And I built it at the time as a sort of place where I thought I can come and do my best work.It’s, you know, small enough that it’s just me in here, me and my, and my little dog who’s here with me now. Little tiny porch on the front and a hard wire internet connection. And that’s it. So I built it as a place to really, as I said, do my best work as a place to write, essentially that was just sequestered from everybody else that, that I couldn’t hear anybody breathe back here. It was just, you know, a hundred percent perfect. And then, you know, fast forward COVID happens. And suddenly my tiny house is now thrust onto the international stage. It’s, you know, now the backdrop for all of these online programs that I’m doing, which is fine.Just that I kind of had to clean things up a little bit. So, so yeah, its kind of been forced into that, the white hot lights of the internet suddenly and the tiny house it’s doing its best back here, but this is not necessarily what it was before originally.Nathan: [00:03:13] Yeah. So it started more as like sort of the writing shed, backyard office kind of thing. And now it’s the working full-time.Ann: [00:03:22] Yeah, exactly. I mean, you know, so MarketingProfs, my company, we’ve always been a hundred percent virtual, so I have a, an office in the big house where I lived. A lot of people think I live in a tiny house. I do not live in a tiny house. It’s a tiny house office only. So I live in a regular size house and I have an office there too.And, and I use that mostly, you know, like in the, in the deep winter, it, this place is not insulated. As you can tell by the plywood background here again, this was supposed to be just for me. I didn’t understand that this was going to be, who knew it was going to be a subjected to the internet on a daily basis at this point.But yeah, so it’s, it essentially built it, you know, for me, this is a place to, to come back when I really just needed some space and some quiet. It actually turns out to be probably, like the best investment I ever made. As a writer, it’s just been such a gift to have this place back here.And you know, even in pre pandemics times, that was true. But especially now, because it does feel like it’s a world away from anything going on, not just in my house, but in my town and my state and my community, anything beyond it, you know? So it’s kind of nice just to have this one, place that as a writer, as a creator, you can feel like, all right, it’s all mine.Oxygen is back here, you know?Nathan: [00:04:43] I like that. Yeah, for me, I, my tiny house office is just across the backyard, from my house and, and I have three little kids, and so getting outside the house, my old office is now our one-year-olds room and like, he can have that space. I can have this space and it’s perfect. So I think we’ll see a lot more people that build out tiny house offices or, you know, backyard things.It’s a good trend.Ann: [00:05:12] Yeah, exactly. And in really creative ways too, like my friend Jeremiah yang has it is a digital consultant. he speaks a lot about, you know, what, what’s next, the future of, of digital. Of the digital evolution essentially. and he put an Airstream in his backyard that he retrofitted with, you know, as, as an office.So, you know, there’s all kinds of diff...

Dickie Bush is a full time Portfolio Manager based in New York City. He is a graduate of Princeton, where he received a degree in Financial Engineering and played on the football team.Dickie writes a weekly newsletter called Dickie’s Digest where he shares thoughts and links on growth of all kinds, including personal, intellectual, physical, network, economic, and other forms of growth.Dickie is probably best known as the founder of Ship 30 for 30, an online cohort based course where he teaches writers how to write better, grow their audience, and show up consistently.In this episode, you’ll learn:How Dickie runs Ship 30 for 30How to build an online writing habitHow to shorten your feedback loops to improve your writingTactical tips to build a following on TwitterLinks & ResourcesJames ClearThe Art and Business of Online Writing by Nicolas Cole30 Days to Better Writing by Sean McCabeConvertKitJack ButcherTim FerrissThe Nathan Barry Show 031: Mario Gabriele – From Lifelong Obsession to Thriving BusinessDavid PerellAndrew WilkinsonSahil BloomJulian ShapiroDickie Bush’s LinksShip 30 for 30Substack: dickiebush.substack.comTwitter: @dickiebushEpisode TranscriptDickie: [00:00:00] One that accelerated my growth, every morning, Monday through Friday at 9:00 AM, you’ll get a question to reflect on where a lot of the replies become interesting pieces of advice. Right? I’m playing with one right now that I said, “Give the best advice you can in just two words.” It had 3,000 replies.The Twitter algorithm. When people respond to something, it shows up in more feeds.Nathan: [00:00:27] In this episode, I talked to Dickie Bush, who works in the finance industry, but has this wildly successful side hustle teaching writers how to write better, grow their audience and show up consistently, called Ship 30 for 30. This episode we get into a ton of great stuff, how to grow your Twitter list, how to stay accountable.We deep dive more than any other episode on the Twitter algorithm, what works, what doesn’t, some of it is pure speculation. Some of it are things that have been pretty verifiable. There’s a lot of good stuff. I think you’re going to enjoy it. I particularly love how Dickie has put together these flywheels that he’s refining each time he does a new cohort of the course. There’s a ton of momentum here. He’s just absolutely going to blow up. And it’s really, really impressive. So with that, let’s dive in. Dickie, welcome to the show.Dickie: [00:01:15] I appreciate you having me. Look forward to it. Nathan: [00:01:17] All of our listeners are very active on Twitter. And you can’t be active on Twitter in the circles that you and I run in and not see your Twitter growth. I see Ship 30 for 30 growing, like crazy everyone, you know, posting essays and all of that. Before we dive into all of that, there’s something that I actually didn’t realize until prepping for this episode yesterday.And that’s that everything we see online is just a side hustle for you. Can you talk about, at a high level, what you do day to day, and then, how you balance that with your wildly successful side hustle. Dickie: [00:01:58] Sure. So what I do, full-time, I’m a macro portfolio manager and the way I kind of describe it as my day job is to predict the global economy and how that unfolds. And there’s only so many charts and numbers you can look at on kind of a daily basis from seven or 8:00 AM to five or six. And so my writing online and kind of journey, and that has been just a, a way to kind of step back from kind of the madness of, of markets and economies and things like that.And explore just little interests to me. And that has evolved relatively quickly, over the last, you know, nine months.Nathan: [00:02:38] Oh, I’m glad you said the nine months time. I, cause that that’s roughly what I’ve noticed as well. What was that inflection point where you decided you’re going to really focus on building an online audience and, you know, start writing online?Dickie: [00:02:54] I guess a little bit of a backstory it’s probably longer than nine months. So I started writing online in January of 2020. With just a weekly newsletter. So I came into 2020 saying, I’m consuming all these podcasts and books and articles and just interested in learning. But my notes would end up in the back of a Notion notebook kind of into the void where, you know, there was no upside.And so I started kind of exploring, how can I start to have a forcing function to learn more about the things I’m doing? So I just started writing a weekly newsletter. I had seen people do it and you just curation and et cetera. So that was kind of my foray into it. And I did that for about 35, 40 weeks, and started writing on a blog, exploring dabbling in some things that I was interested in, but in July, I’d probably published 30 or 40 newsletters in a row, a couple of blog posts, but just felt like I was kind of stuck and had so many ideas that I wanted to explore, but didn’t have the medium to do it. When my feedback loop was slow, I was on the weekly cadence, but it was inconsistent, et cetera. And so coming into August, I started just tweeting more and getting through these ideas. And I’m sure we’ll talk more about Twitter. It’s kind of an idea refinery, right? You can just get these ideas clear the junk that’s in your head to find out what you really want to talk about.And so that was, you know, that was kind of the inflection point was when I made a new Twitter account in August and said, “I’m going to start to share these ideas that I think I want to talk about.”"Nathan: [00:04:27] As much as I want to ask there, but you said you made a new Twitter account. You just started more from scratch and kept, you know, forked off of an old one. What did you do there?Dickie: [00:04:34] So that one, I had a Twitter I’ve had Twitter since 2014, 2015, you know, big lifetime, just been involved with the product and loved it. And. There was a little bit of, okay, I’m going to pivot this. I had four or 500 followers at the time, had done some kind of thread curation and things like that. But my follower graph, I think was a little bit not damaged, but Twitter’s algorithm.If you went on my account and said, who are this person similar to? It was all inactive accounts from high school. And so I just wanted a fresh slate too, kind of start over. And so I made the new account and said, Hey, I’m maki...

Jason Feifer is the Editor in Chief at Entrepreneur, an American magazine and website that carries news stories about entrepreneurship, small business management, and business. He also hosts a podcast called Build for Tomorrow, and he is the author of a forthcoming book titled Build for Tomorrow, Not for Yesterday.Jason is a unique blend of individual creator and polished corporate employee, so he offers a balanced perspective on work and content creation. In this episode, Jason and Nathan discuss:How to package your workHow to pitch your content and get press as a creatorTime management for creators balancing full time careersLinks & ResourcesEntrepreneurBoston MagazineMen’s HealthFast CompanyMaximJames BurnettMarc AndreessenPessimists Archive: @PessimistsArcLouis Anslow: @LouisAnslowAndreessen HorowitzJoel WeberJason Feifer’s LinksPersonal site: jasonfeifer.comJason’s Podcast: Build for TomorrowJason’s forthcoming book: Build for Tomorrow, Not for YesterdayJason’s Instagram: heyfeiferJason’s Twitter: @heyfeiferEpisode TranscriptJason: [00:00:00] You make the thing that you want to make. You believe in it, and you don’t give up on it, and you spend years doing it. And if you’re good at it, and if you were right that this was a thing that was worth making, people will find it because good really does rise up. It happens slowly, but it does happen.Keep going. Nathan: [00:00:23] In this episode, I talked to Jason Feifer. Jason’s the Editor in Chief of Entrepreneur. And we dive into a bunch of different things.One, how he splits his time as an individual creator and, you know, running a very successful, very popular magazine. How he blends those things. He’s got a newsletter, he’s got a podcast, he has several podcasts. He’s working on a book, all of those things. So how he prioritizes his time. All of that.The monthly cadence that he works on, I found really interesting. We also dive into how to package your work. We talk about why he changed the name of his podcast and the research that went into that. Then finally we wrap up by talking about PR and how to get press as a creator, how to think about pitching each individual publication, the work that you need to do to actually get covered a lot of good stuff.So let’s dive in.Jason, welcome to the show.Jason: [00:01:15] Thank you for having me.Nathan: [00:01:16] So I want to dive in, you’ve got two very different things going on. They’re actually, I mean, they’re closely related, but, two different worlds, you know, with everything you’re building on your own audience. And then of course, as Editor in Chief of Entrepreneur, I’m curious just how you spend your time, as I would think the Editor in Chief is a very time-consuming thing. Then you’re building an audience. You’ve got two young kids, you know, you’ve been doing it all through a pandemic. And so I’m curious what, you know, what a day or a week looks like, in Jason’s life. Jason: [00:01:51] it looks like panic. It looks like absolute mass panic. That’s how I feel. Panicked. Okay? So first I’ve made this, I made this realization a couple, more than a year ago. I can’t remember when this took place for me, but I realized that I needed to maximize how my brain works, like work with my brain.Right. Which is to say, when am I best at doing various things? And then let’s make sure that I’m doing those things at that time, because if I can write a full, like 2000 word story, in, let’s just say two hours, which sometimes I can do, that’s going to happen in the morning. If I try to do that at 5:00 PM, it’s going to take four to six hours.So why on earth would I waste my time doing tasks when I’m not primed for them? So I clear out the for if I can manage it up to noon, but that’s almost impossible. So really can I safeguard the first hour and a half of my day for writing? And then what I do with that hour and a half depends upon the needs that are most present for me.So for example, sometimes it’s writing a magazine story. Sometimes it’s writing a chapter in my book. Sometimes it’s writing a podcast script and this is dictated by the deadlines that I have. And then the rest of the day, I’m trying to manage everything that needs to be managed. I’m answering a lot of questions.I’m getting on a lot of calls, but I will, Oh, I, if I can. If I can do it, which I can’t always do, but I can do it. Then I will not book anything back to back. I will always block out like a half an hour in between. And that’s because things are coming at me and they’re coming at me for lots of different projects.And it’s hard. You can, you think that you can switch gears really fast between one project and another one company in another, as I’m sometimes doing, because I have my own company and then I’m also working with Entrepreneur and I mean, I, I mean, I’m employed by Entrepreneur. and so I need that time to make those shifts.And the days that I hate the most are the ones, well, first of all, where I lose that time in the beginning, but also where I’m back to back and I never have time to catch up on any of the inbound because that’s when I’m working late into the night.Nathan: [00:04:13] Yeah, that makes sense. Are there other things that you’ve found? Right. So writing in the morning is something and I can absolutely relate to that where like 3:00 PM. Nathan is, he’s actually just legitimately terrible writer. He wants to do anything, but Write, are there other things that you’ve found of like blocking off days of the week to focus on.You know, one activity or one business or anything like that.Jason: [00:04:35] I don’t, I have too many constant demands to be able to block out full days. I would love to be able to do that. So instead, I tend to think about things in terms of goals for a week. So I know for example, here’s, here’s an example. I know that my Build for Tomorrow Podcast comes out on the last Thursday of every month and it’s a monthly show, which I know is not a great cadence.Yes, yes. I’m aware, but it is such a deeply researched, highly produced show. It is, it is a months worth of work that goes into every episode. And for reasons that we can discuss I’ve decided that that’s okay because the. Ultimate goal of a podcast. Isn’t always just to have a bazillion listeners of the podcast.Sometimes it can se...

Veni Kunche runs Diversify Tech, a newsletter-based business all about helping people who are underrepresented break into the tech world. After working as a Software Engineer since 2003, her main goal now is to help make the tech industry inclusive.Veni’s got a really interesting business model: a mix of sponsorships and also a job board, taking advantage of the robust community that surrounds her newsletter.Nathan and Veni cover everything from how she transitioned from working in tech to starting her business. They dive deep into the mistakes companies make when seeking to hire a diverse team, and and what they can do differently.Veni also shares real numbers. Listen to the end to hear:• How much she’s making per month from her newsletter.• How her revenue has changed over the last year.• How the pandemic has affected her sign-ups.Links & ResourcesBlack Tech PipelineTechqueriaOut in TechVeni Kunche’s LinksDiversify TechBusiness & Ally NewsletterPersonal site: veni.devTwitter: @venikuncheEpisode TranscriptVeni: [00:00:00] Companies write job descriptions, they’re writing for mainly men in tech. Also they’re writing for younger people. Oh, we have ping pong. We have pool at our office. Those are the benefits. My community don’t even care about that. What they care about is focused on how the company will support them in their career.And so those are the signals that they’re looking for.Nathan: [00:00:26] Today’s interview is with Veni Kunche who runs a newsletter-based business called Diversify Tech, which is all about helping people who are underrepresented break into the tech world. She’s got a really interesting business model of a mix of sponsorships, a job board, which I think is a business model on newsletters that we don’t talk about enough when you have that community.There’s a great opportunity there. Anyway, it’s a great episode. We cover everything from how she got started, transitioning from tech to starting her newsletter. We dive deep into companies who are looking to hire a diverse team and mistakes they make and what they can do differently, how transparency really matters.So there’s a lot of good stuff in there. Towards the end of the podcast, she gets into sharing the exact numbers behind the business, how much she’s making per month, how that’s changed over the last year. I think you’re going to love it.Let’s dive in.Veni, welcome to the show.Veni: [00:01:16] Thank you so much for having me happy to be here.Nathan: [00:01:19] So I thought I’d just start. If you could tell listeners a little bit, what is Diversify Tech and, you know, at a high level, like what’s the business model behind it.Veni: [00:01:30] Yeah. So Diversify Tech is a curated newsletter, primary purpose is to connect people who are underrepresented in tech with career opportunities. So I share scholarships that are available, jobs, events that are happening, around the U.S. so the main purpose is to connect, people who are underrepresented, to these opportunities.The reason I started it is because when you’re underrepresented, when you’re in your workplace or in your college at college, or wherever you feel where you’re alone, and you don’t really have a network, of people like you. So I wanted to bring something where I could be that resource for people.Nathan: [00:02:19] Yeah, that makes sense. So when you were working as a software developer in tech was this an idea that you were thinking about for a long time and you’re like someone should make this, and then you realized that that someone was you, what was that? What was that leap?Veni: [00:02:37] So actually like, had no intention of starting something like this. It was, I actually just wanted to start a business. I didn’t know what that was. so I was a staff engineer for quite some time and I didn’t quite fit into the corporate world. I kept switching jobs a lot, so I was like one day I was like, you know what?I think I want to try something on my own. So I started exploring how does one start a business? How does one? And I, you know, I learned that, you know, it takes quite some time to figure out who your customers are, customer market fit, you know, all of that. And as I was learning, I was also volunteering for the women who code chapter in DC here.And, as I was volunteering, I connected with a lot of women in tech and that’s when I realized that there are a lot more, floods than I thought, and blah, and everybody was trying to find each other kind of, to feel connected and to kind of talk through this, you know, our issues. and I started doing just online office hours.So I was like for 30 minutes, I would just get on Google Hangouts and talk with people. And I got connected with so many people from across the U.S. just by offering that. And then that’s when I realized, okay, everybody’s. It’s facing similar issues and we’re all discussing the same thing over in Oregon.So I thought, Oh, why don’t I start a newsletter where I can reach more people. So prior to Diversify Tech, I started a newsletter called Code With Veni, and I was like, Oh, I’ll share what I’m learning. And I will also, you know, share what other women in tech are doing. and you know, it was more supposed to be like inspirational and, you know, that’s how it started.And after a year of running that I started getting requests for sponsorships. People want it to sponsor the newsletter. People wanted to post jobs. Uh that’s when it finally clicked that I was like, Oh, I’m starting trying to start a business. And I think I actually started, okay. So that’s what it is like, Oh, once I started getting, receiving his foundation of, so I was like, Oh, this could be my business.So that’s when I was like, then I kind of pivoted off of good with many. Cause I didn’t want the branding to be just me. So, and then I also wanted to include not just women, but everybody who’s underrepresented in tech. So that’s when I kind of like Diversify Tech from that. Nathan: [00:04:54] It’s always fascinating. How, when you build an audience, sometimes like the, the business model will just come, you know, or the business will just come and you’re like, I don’t know what it is. And then over time, someone’s like, Oh, could I do this? And you’re like, I mean, I guess so like, sure. Yeah.Let’s talk sponsorships. That’s a great idea. Let’s you know, and then I imagine people are like, great, can I sponsor with my job listing, you know, or something like that. I’m trying to get it in front of a more diverse community. And so it was that where like the job board came in,Veni: [00:05:25] Yes. As I started growing the newsletter sponsorships kind of, didn’t make it like, but sense because the demand was higher than I, because I send the newsletter every week, you know, I can’t have that many sponsors showing a...

Venture capitalist Li Jin left Andreessen Horowitz to start her own firm, Atelier Ventures. She started Atelier to fund a specific vision of the world: a world in which people are able to do what they love for a living and to have a more fulfilling and purposeful life.In addition to being an investor, Li is a prolific writer and podcaster, producing not only a newsletter but also writing articles for major publications.Find out whether you should really be writing content every week, or whether your effort is better spent on longer-form, epic articles. Should you be publishing in your newsletter, or in publications like Harvard Business Review?Li and Nathan don’t just talk about content, they also get deep into business models for your newsletter business, with Li sharing her perspective as the founder of a venture fund. Don’t miss Li’s unique combination of deep investment knowledge and artistic creativity!Links & ResourcesAndreessen Horowitz - Software Is Eating the WorldLiveJournal: Discover global communities of bloggers who share your unique passions and interests.MyspaceZyngaThe Nathan Barry Show 028: Packy McCormick – How Much Are 30,000 Subscribers Worth?EvernoteHarvard Business Review - Ideas and Advice for LeadersThe Nathan Barry Show 023: Tiago Forte – Building a Second Brain & Lessons From a $1M/yr NewsletterThe Nathan Barry Show 017: David Perell – Mastering Twitter to Grow Your Newsletter and Make MoneyLi Jin’s LinksNewsletter: Li’s NewsletterWebsite: Atelier VenturesPodcast: Means of CreationTwitter: @ljin18LinkedIn: Li JinEpisode TranscriptLi Jin: [00:00:00] What are your goals and what is the content that you’re creating and why are people subscribed and reading it? The business model needs to fit what your content is, who the audience is, who the creator is, what the platform is. All of those things need to be aligned. Direct user monetization is totally in vogue in the form of donations, ad hoc payments, subscription payments.It’s always charging the user for something. Nathan: [00:00:28] Today’s episode is with venture capitalist Li Jin. So Li was at Andreessen Horowitz, and then she recently left to start her own firm, Atelier Ventures. We talked about a lot of things that I find interesting, like business models for your newsletter, for example, should you monetize through a paid newsletter sponsorships or what she does through running a venture fund?We get into whether you should write content, you know, consistently every week, or should you publish it once a quarter and put out these incredible long form posts we get into writing about, or excuse me, writing for publications like Harvard Business Review versus your own newsletter. There’s so much good stuff in here.So I’ll just get out of the way and we’ll dive right in.Li, welcome to the show.Li Jin: [00:01:14] Thank you. Thanks so much for having me, Nathan.Nathan: [00:01:17] Okay. So I want to dive in and just immediately talk about revenue models, all of that, because you have this tweet that I just loved, that it was like dying, laughing when I saw it. And the gist of it is I have a paid newsletter. It’s my monthly LP update. You were talking about how either those business models is everything else.And I imagine saying like me, why don’t you launch a paid newsletter? So could you talk through how you think about, you know, your business and what you meant with that week?Li Jin: [00:01:50] Yes. So I joke that my LP update, which I send out quarterly as a email is basically my paid newsletter. And I think it’s, it’s basically a riff on the joke that we used to make about a16z, which is the firm that I used to work at the VC firm that I used to work at. We used to joke that it was a media company that monetized through venture capital because a 16, Z as a firm is so prolific in creating content.They have a podcast, actually, a network of podcasts, the blog. they have a series of different clubhouse shows now as well. they just do a ton of different media and content creation activities. And so people used to joke like, Oh, this is actually a media company that happens to monetize through venture capital.And I think of myself now as kind of a miniature version of that, where I’m a solo. Content creator. and I monetize through venture capital. Like that is my revenue model. I have a venture capital fund that I raised last year, called . And that is, you know, my day job. That’s where I spend the majority of my time.And then the content that I put out into the world, It’s free. It’s, it’s mostly free for founders to consume. It’s really designed to help them build companies, and to guide them and their strategies. And I don’t monetize the content at all. And the way that I monetize the content is through investing in the best companies that come as a result of the content creation.So, yeah, that was, that was the Genesis behind, the tweet. And so the LV newsletter, I mean, the LPs are like the investors in the fund and that’s how I monetize it.Nathan: [00:03:33] Yep. That makes sense. And I think once you have this attention, Then there’s so many ways that you can monetize it. I was talking with Trey, remember who wasn’t a past episode. we were talking about how people have alluded to Nike being like they’re just an ad agency who happens to realize that the best model to monetize is through, you know, shoe and apparel sales, but really their core strength is advertising and marketing.And so I think there’s plenty of examples of people who have, like, the. Have this audience and then an unconventional way of earning a living.Li Jin: [00:04:09] Yeah, precisely. And I think to build on that. Like there’s a lot of examples of newsletter writers who do a similar thing where they’re operating a syndicate. Like I think Packy who you’ve had on the show has a syndicate that he invests in deals through. there’s other newsletter writers. I know that angel and fast Lenny Rachitsky is a very active angel investor too.So yeah, a lot of them are sort of blending different business models because newsletters are such a great vehicle to, to build an audience. To get reader attention, to communicate your thoughts into the world and kind of mind-meld with a lot of really interesting folks. And then the best way to monetize that might not be through a straight up subscription or pay.Well, it might be having upside in the businesses that they built. and I think. Content creators are having that rea...

Mario Gabriele is the founder of The Generalist. His mission? To bring the most interesting tech writing to your inbox, every week. And he’s not doing it alone, either: Mario works with a team of contributors to deliver new ideas from some of the most original minds in venture capital and tech.In this episode, Mario talks about how and why he left a career in venture investing to build The Generalist, and his lifelong obsessions with writing and technology. The Generalist is not only a really successful newsletter, it’s a thriving business, too! Tune in to hear how Mario did it.You’ll learn about approaching and collaborating with the people you only dream of working with. Mario talks about how he went from merely admiring certain writers’ work to joining their “club” in 18 months!Mario also shares the most reliable way to advance your career, and the safest ways to accelerate it. There’s a lot of good stuff in this conversation!Links & ResourcesStratechery by Ben Thompson – On the business, strategy, and impact of technology.Exponential View by Azeem AzharThe Nathan Barry Show 028: Packy McCormick – How Much Are 30,000 Subscribers Worth?Acquired PodcastAtonement by Ian McEwanNorwegian Wood by Haruki MurakamiAll-In with Chamath, Jason, Sacks & FriedbergWebflow: The no code platform for web design and developmentPico - Signup and payment tools for the internet’s most passionate communitiesalexdanco.com – subscribe weekly at danco.substack.comMario Gabriele’s LinksPersonal site: The GeneralistTwitter: @mariodgabrieleEpisode TranscriptMario: [00:00:00] I just really love writing very, very much. And so, as soon as I got the width that like, maybe I could make this a real thing, then suddenly like a flip switched in me where I was like, all right, I have to go as hard as possible and feel like the value was accruing directly to me. As soon as I was like fully on my own thing, I suddenly felt like, Oh man, I’m unchanged to go after this. Nathan: [00:00:30] In this episode, I talked to Mario Gabriele. Now Mario runs an email newsletter called The Generalist, which is focused on tech venture capital and investing. He comes from the venture capital world himself, and then he really brings forward all of that into the newsletter. A couple of things really impressed me about Mario. One, he really collaborates, well, he’s got something called the S–1 Club, which is where they do tear downs of filings that companies make before they go public. And he really brings in other creators and they write them together. He also has something called RFS, which is Request for Startups and he brings in other venture capitalists and operators and everyone else to share startup ideas.So he’s got this interesting mix of his own Content, Community Content, and he’s built it not only into a really successful newsletter, but also a thriving business. So it’s a lot of good stuff. Let’s dive in.Mario. Thanks for coming on the show.Mario: [00:01:25] Thanks for having me, Nathan.Nathan: [00:01:26] Okay, so you have this line. I think you said it on Twitter and a few other places that I just want to start with. You said, it sounds ridiculous to announce your dream is to build a great newsletter and then you go into like, you know, but that’s what I’m doing, you know, my love of technology and writing and everything else. So maybe just start with why, like, why did you want to start a newsletter?Mario: [00:01:52] Yeah. I mean, honestly it wasn’t, something that was necessarily in the back of my mind for a long time, it really sort of happened organically. and I think work is often like this where for a long time, you’re not really sure exactly what you’re doing. And then. When you sort of find something that actually feels incredibly right, you can sort of trace back all the little things along the way that brought you there.And so for me, that was really two main, explorations. One was that, you know, from a very young age, I’ve always really enjoyed writing. and so I did a lot of that in school. and then after I’d left university, I started to take night school classes and fiction writing at NYU. Starting in 2012, I started to like write a novel every morning, getting up early, you know, spending an hour before work, just sort of like practicing, practicing, practicing.And it was just sort of this hobby I had. And then simultaneously where I was really building a career was in technology. so. You know, on the operating side, at a few companies and then on the investing side in sort of a few venture firms and, starting The Generalist really was just a way to.You know, I express that hobby in a slightly different way. I had folks be like, all right, cool. You’re spending all this time writing. Like what, why don’t you write a thing or two about, about your actual work? and so just started as sort of a side project on the weekends and then bit by bit, it just was absorbing more of my thought.More of my excitement, more of my energy. And it started to really feel like it was pulling me in this direction. And, once I felt like it might be possible for writing to become. My life’s work and be a viable career, which had always been sort of the reason I hadn’t tried to go full-time as a novelist.You know, even though, you know, unless you’re JK rallying, it’s pretty impossible. newsletters felt like a way I could do that and really write the stuff I wanted to write, and make, make a living out of it. Hopefully.Nathan: [00:04:09] Yeah. So, it’s, we’re recording this in February, 2021. When was it that you started The Generalist?Mario: [00:04:16] So I start, I wrote the first ever post in August of 2019. And honestly was sort of an accident that I started it as a newsletter. I had just been seen seeing people like switch over to Substack over Medium. This is before I had heard the gospel of ConvertKit. So, yeah, I was just like, cool.I’ll do this instead of Medium, like whatever. and then. That first post, even though it was very small circulation just led to so many interesting conversations and people started to sign up. And so it suddenly became like very clear why you should make it a newsletter versus a blog. and then I would say the other sort of critical point was in August of the following year. I went full-time on it. And the growth since, since then has been like significantly different, I would say, just like being able to put more time into it.Nathan: [00:05:15] Yeah. So, there’s a few things that I want to dig into there, but, I think there’s all these creators that we look up to and admire, right? The newsletters that we read, that YouTube chann...

Sam Parr founded The Hustle, a top-flight newsletter that he grew to almost 2,000,000 subscribers… and just sold to HubSpot! Tune in to hear the whole story of how Sam grew a successful newsletter to seven figures per month in revenue, and the roller coaster ride of selling his small business.Despite his success with a paid newsletter, Sam has lots to share about what people are doing wrong when they launch a Substack. Plus, he gives Nathan ideas and tactics for growing a new, local newsletter that focuses on Boise.In this wide-ranging conversation, you’ll also hear about the art of writing quickly, whether writing your newsletter is something you can (or should) delegate, and whether running a solo newsletter is even the right business for you in the first place.Links & ResourcesHubSpot - Inbound Marketing, Sales, and Service SoftwareProduct Hunt – The best new products in tech.DailyCandy - Sweet SorrowThrillist - Find the Best and Most Under-Appreciated Places to Eat, Drink and TravelFool.com: Stock Investing Advice - Stock ResearchJames ClearGumroadGlossier - Skincare & Beauty Products Inspired by Real LifeSam Parr’s LinksSubscribe to The Hustle DailyTrends by the Hustle - Your next business idea, delivered weeklyTwitter: @theSamParrEpisode TranscriptSam: [00:00:00] I think they’re making the wrong mistakes. The first example is pricing. Most people charge way too little, but if you actually want to make a living at this and provide value, you’ve got to charge more money. How are you gonna make a living if you’re charging $4 a month? That’s really, really hard.So charge way more. People tend to like that stuff more. If they paid money for it, they usually appreciate it. Nathan: [00:00:25] In today’s episode, I talked to Sam Parr from The Hustle. Now Sam and I have been friends for a long time. And he’s got some pretty wild news in that, HubSpot just acquired The Hustle. There’s a lot of crazy things that went on with that, but, we dive into the story there. How long due diligence took everything else.It’s a long ranging free-form conversation. But we hit another things like, my new local newsletter that I’m starting. He has some growth ideas and tactics that he shares there. We get into what he thinks people are doing wrong when they’re launching Substacks, which is pretty wild since he has crazy revenue.I think, you know, there are over a million dollars a month in sponsor revenue and getting pretty close to that in paid memberships revenue for The Hustle. And we get into growing the newsletter to almost 2 million subscribers. There’s so much good stuff. I’ll warn you. It’s a very rambling conversation, but we have a great time.So I hope you enjoy it.Sam, thanks for joining me.Sam: [00:01:18] What’s up, man?Nathan: [00:01:19] So you would have been friends for a long time. It was hung out in a lot of different circles. You’re wildly popular on the internet today, not today, over the last couple of months, a couple of weeks. Sam: [00:01:30] Not as popular, popular as you.Nathan: [00:01:32] Exactly. I don’t know, but you just sold The Hustle and we were talking right before we hit record and you’re like, dude, just hit record so that we can have the whole conversation for everybody. On the first question I was asking is how long did it take from when, when HubSpot reached out to the deal actually closing,Sam: [00:01:53] About 90 days. Well also, had you ever sold this business before?Nathan: [00:01:57] I have not, I can’t say what business I acquired, but this week I acquired a company. it just closed. Sam: [00:02:06] Was it a big deal?Nathan: [00:02:07] It was a medium deal.Sam: [00:02:09] Okay. That’s great. Well, we,Nathan: [00:02:11] If you bucket deals into small, medium and large, it was a medium deal. So.Sam: [00:02:15] Well we, We, like, I didn’t know. I mean, I had been part of a company selling before as a shareholder and like a investor, an advisor, a very, very close advisor, but I still didn’t know. I didn’t know like what closing meant. I didn’t know what signing meant. I didn’t know. I didn’t know anything. And so I didn’t, I didn’t know what a LOI was.I didn’t know. I mean, I had heard the words, but I didn’t really know like what that implied. And they reached out to me around September or October. They cold emailed me and we had been recruited or, you know, buyers have talked to us for a long time. And like the first couple of times I took them really seriously.And I was like, Oh my God, like, I’m going to dress up nice and fly out to their office. And I’m going to show them all this school stuff. And then after awhile I was like, I just didn’t take it seriously. And I just said, I would send them like, I would like write up like a one pager and I would like tell them all the reasons basically why they shouldn’t bias where, I mean, I was like, look, we’re really good at this.We are horrible at this. the reason why you should buy us as this, the reason why you should not bias as this, if you are, the, the, the expectations for pricing is around this. If you want to talk, call me and like, it was a pretty straightforward thing. And, they liked that. And most people don’t, most people don’t like that.And so they emailed me and then we, we, the deal was announced, like the last day of January and they emailed me in October.Nathan: [00:03:47] So I feel like that’s pretty quick.Sam: [00:03:49] Is it? It certainly doesn’t feel quick.Nathan: [00:03:51] You mentioned on, on your podcast, that due diligence was. I think hell was the phrase.Sam: [00:03:59] It is so bad. It’s so bad for a bunch of reasons. But first of all, I sold to a public company.Nathan: [00:04:06] Yeah. Sam: [00:04:06] I’ve never sold a company for $300 million, but I have a feeling selling for 300 or 500 or actually have been the same amount of work as for what we sold, which was less than 300 million. it’s a ton of work.And the difference between my small company, it was that I didn’t have a team of like, I don’t ha I had like one woman named ed who works on accounting and finance. And then I had outsourced a lawyer, you know, like an outside law firm. I had an outside tax firm. And then I had me and I had to do a lot of this in private.You can’t really tell employees. And it was very, very hard. They basically, I ha...

Codie Sanchez runs the amazing newsletter Contrarian Thinking, whose topics include passive income, generational wealth, contrarian investing, and learning from strivers who think big.Her motto is “Question everything and stack income streams”, and that’s exactly what we talk about in this episode. Not just “how to build a newsletter”, but one of Nathan’s favorite topics: how to build wealth!You’ll learn how Codie went from journalist to investor to partner in a fund, and how she runs her 100,000-subscriber newsletter plus other companies besides. Codie talks growing a newsletter from 100 subscribers to 1,000 and beyond, but that’s not all.Tune in and find out:Why Joe Rogan’s deal with Spotify was a huge mistake.Getting people to promote you… without sounding thirsty.How to build an all-star team for your growing business.Whether ads or sponsors are a better way to monetize your newsletter.It’s a great show!Links & ResourcesUnconventional AcquisitionsZero to One: Notes on Startups, or How to Build the Future by Peter ThielJoe RoganHoward SternMr. BeastNoah Kagan Marketing & Business Blog - OkDork.comSam Parr CEO at The HustleJonah Goldberg - The DispatchCharles E Gaudet II » Predictable ProfitsContrarian CashflowCodie Sanchez’s LinksNewsletter: Contrarian Thinking by Codie SanchezTwitter: @Codie_SanchezInstagram: @codiesanchezEpisode TranscriptCodie: [00:00:00] The funny thing about audience is money doesn’t care if people care about you. So capital as a leverage source, doesn’t care about relevancy, your dollar, as long as it stays in the market. And you keep reinvesting will have compound interest. The thing about audience is, it can be a depreciating asset. If you don’t pay attention to it, if you don’t upkeep it just like you would a house, then your audience is going to think that you’re not relevant.Nathan: [00:00:32] Today’s episode is with Codie Sanchez. Now Codie has a fascinating background where she started in journalism and there, she was covering a lot of things in Mexico and on the US-Mexico border. So she has crazy stories from that. And then she goes into investing, right? Like it goes to Goldman Sachs and Vanguard and goes to the whole investing world.And then now she’s in not just investing, where she’s a partner in a fund, what was the investing in cannabis companies, but she’s also running a newsletter, with over a hundred thousand subscribers, which is pretty crazy. And we get into how to monetize the newsletter, how to grow it, her take on the creator economy, so many other things. So it was a great conversation and let’s dive in.Codie, thanks for coming on the show.Codie: [00:01:19] My pleasure. Thanks for having me.Nathan: [00:01:20] So you and I have we talk newsletters and everything, which we will, but first we have a shared love for the same topic, a topic that some people love to talk about. Like we do, and other people dance around and think is weird and awkward and everything else. And that is building wealth. Like you and I both love this topic.Why is it something that you, what about so much on all your social channels and your newsletter and everything else?Codie: [00:01:44] Yeah, well, I mean, yeah, I nerd out about this. It might be just because I’ve been in finance for 72 years, but, more than that, I think if you want to. Control the art, you have to control the resources behind the art. And so I’ve always loved creating, I mean, similar to you in multiple different ways, whether you’re creating a business or a newsletter or whatever the case may be.I like the act of creating and if you don’t have the financial resources to actually do the creative, and then there are all of these pressures that get put upon you, and I don’t think you get control of the art. And so that would probably be one of my main reasons. And then secondarily, I just think financial freedom without financial freedom, you don’t have any freedoms. And so that’s sort of one of the building blocks, I think, crucial for people to get.Nathan: [00:02:29] Yeah, that makes sense. So, one thing that you talk about quite a bit is leverage and finding leverage on, you know, as a tool for building wealth, maybe explain some of your thinking behind that and how you’d like to encourage your readers for your newsletter and, you know, companies you invest in to find leverage.Codie: [00:02:46] Yeah, well, we were kind of talking about this before, you know, I thought I was like brilliant and some of these ideas, and then I realized that like the internet also now has caught up and some of this stuff is more normalized, but, You know, when I thought about leverage, I thought about it with four parameters.And that was first you had labor, then you had capital. Then you had code. Then you had audience. Now Naval Ravikant talks about the first three. he doesn’t mention the fourth and the fourth I think is really, in my opinion will be sort of the next frontier, the creator economy, and leveraging your audience in order to get different revenue streams.Because audience is really fascinating in that it’s like an annuity, meaning that it can cashflow consistently, but instead of annuity—only having one revenue stream, you know, they pay you out based on the investment that you make—audience can have have a billion revenue streams. And so anyway, when I think about leverage, I don’t think about it as a financial way.Lots of people think about leverage. Like you loaned me a dollar and I take that dollar and go do something else with it. but the world we live in today that was old school leverage, you know, that was the leverage that created. Basically the biggest Titans of industry in the US: the Rockefellers, the Rothschilds—they were all created right after banking was established.So the banks came out, capital was created. These guys made a ton of money, and then you had code come out, software, right? Robots in the form of software and the next biggest billionaires were created. That’s the Jobs, that’s the Elon Musk, etc. And now in the next realm, I think those with audience will be the next sort of wave of billionaires that are created.And they’re all enabled based on code to some degree. but I think that’ll be the next evolution. So if you are able to understand leverage in a modern day format meaning not just human capital, the most inefficient form—labor like you and I working for living and renting out our time—and not just money like me and the fund, having a bunch of other people...