The Quarter

Download the Bootstrapped Report: https://www.jointhequarter.com/bootstrappedWe're heading into the start of the academic year where many students want to start their own business while taking classes. Building a startup within a university is actually a great time to do it – you have stability from classes and lifestyle, plus lots of people to bounce ideas off of quickly.But your time as a student entrepreneur is extremely limited, especially if you're an MBA student with two years max. Two years might feel like forever right now, but that's nothing in the grand scheme of building a business.How do I know this? My full-time job is leading student entrepreneurship at Yale, and as a creator, I've developed The Bootstrapped Report where I've analyzed 50+ bootstrapped businesses that have grown past $250,000 in annual revenue. It takes on average two and a half years to reach that mark.In this video, I'll cover:- The biggest traps for student entrepreneurs- How to overcome the most common challenges- How to make the most of university resources that you only have access to as a student founder

Download the Bootstrapped Report: https://www.jointhequarter.com/bootstrappedLearn more about Centered: https://centered.teamFull Deep Dive: https://www.jointhequarter.com/blog/hoomhouseIn 2020, raising money was easier than ever before, and yet, Bryce Kaiser and his wife Lauren did something that was a bit crazy.They said no to all of it.While everyone was raising money because it was "free money" during the COVID boom, the HoomHouse founders deliberately chose to stay bootstrapped.Then on top of that, they walked away from maybe the hottest market in the entire world at the time: telehealth.And instead they just doubled down on one simple growth strategy.Three years later it all worked out. They sold the company on their own terms.In this deep dive I break down with Bryce, his simple approach to building a marketplace business, why saying no to VCs was actually the smartest move they ever made, and the surprisingly simple approach that made their exit possible.

Download the Bootstrapped Report: https://www.jointhequarter.com/bootstrappedRead the full deep dive: https://www.jointhequarter.com/blog/processdrivenCheck out ProcessDriven: https://processdriven.coBy saying it's my MBA business, I basically gave myself permission for the first three years to just focus on learning and getting paid anything to learn is great when you compare it to an MBA where you're paying to learn."That's Layla Pomper the founder of ProcessDriven, a company that helps small teams clean up their operations so they can turn their messy chaos into control.Layla has bootstrapped ProcessDriven to over $250,000 in annual revenue and over 100,000 subscribers on YouTube. But here's the thing - ProcessDriven was never supposed to be like this.It was supposed to be just a business that she would run for maybe two or three years. Well, seven years later, and Layla still hasn't applied for a new job.In this deep dive, we'll explore the mindset that helped Layla grow ProcessDriven initially, the three different chapters or pivots of ProcessDriven, and how Layla has used YouTube to grow ProcessDriven to where it is today.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedSilkscreen Marketing: https://silkscreenmarketing.comFull Deep Dive: https://www.joinstation.co/blog/silkscreenmarketingPhoto Credit: https://www.hollandsentinel.com/story/news/2011/12/25/mygreatlakeonline-allows-fans-to-show/45298490007/When I started my entrepreneurial journey, Kylen Blom was one of the founders I immediately looked up to. He had legendary stories like sleeping in boats to sell his t-shirts, and he was already running his business full-time right after college while I was just getting started.That felt like the dream.Today, Kylen is a good friend and someone I still admire. He's the founder of Silkscreen Marketing, an art-focused production studio in Holland, MI. He's built an incredible studio that takes swag items that usually come out generic and boring and makes them genuinely creative and memorable.In this deep dive, we'll explore how a college pitch competition led to sleeping in boats around the Great Lakes, how a small local team competes with giant competitors, and how Kylen and his team think about growth in a different way than most.

Download the free Bootstrapped Report: https://www.joinstation.co/bootstrappedRead the full deep dive: www.joinstation.co/blog/brandibernoskieLearn more about Brandi: https://brandibernoskie.comBrandi Bernoskie didn’t set out to build a million-dollar business. In 2011, she was writing content for NASA and running a small blog on the side, mostly for herself.As she taught herself to code websites and friends started asking for help, a small side project grew into something more.A couple of key mindset shifts turned that side hustle into what is now a $1M website agency, Alchemy & Aim.In this deep dive, we’ll explore the mindset shifts Brandi made to go from side hustler to $1 million business owner, how her focus on service helped her stand out, and why her approach directly challenges one of the other founders I’ve featured here on The Quarter. And after studying dozens of bootstrapped businesses in The Bootstrapped Report, Brandi’s story stands out as one of the clearest examples of how to grow a healthy, sustainable company.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedPlausible Analytics: https://plausible.ioPlausible's Live Public Stats: https://plausible.io/plausible.ioFull Deep Dive: www.joinstation.co/blog/plausibleIn 2018, when Uku Täht was asked to set up Google Analytics for his company, he asked a key question: "Can we just use something other than Google Analytics?"At the time, the answer was no. But fast forward to today, and there's a good chance you might use a company called Plausible Analytics, which now makes over $1 million in annual revenue by being everything Google Analytics isn't.Plausible is simple to use, doesn't track individual users, and isn't free…You might think charging for something Google gives away for "free" is business suicide, especially for a bootstrapped two-person team. But Plausible's story shows that sometimes being the paid underdog with a clear "we're not Google" positioning is exactly what people want.Now, how Plausible has grown this has been a little unique compared to the dozens of bootstrapped companies I’ve studied in The Bootstrapped Report because it’s maybe the most straight forward growth strategy I’ve seen. With online privacy being a key concern for many right now, let's dive into how Plausible Analytics has bootstrapped their way to over $1 million in annual revenue by being the privacy-focused alternative to Google Analytics.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedCheck out Sam's book: https://www.samvanderwielen.com/book/Try Kit for free: https://partners.kit.com/matthewgira (this link is an affiliate link, so I do get some credit/rewards if you sign up to Kit!)The full deep dive: www.joinstation.co/blog/samvanderwielenSometimes the thing people want from you isn't what you're trying to sell.That's exactly what happened to Sam Vander Wielen. After spending 4 years as a corporate lawyer, she decided to become a health coach in 2016. But when she showed up at a creator conference called "The Good Fest" to find clients for her health coaching business, something unexpected happened.A lot of people wanted to meet with Sam, so much so that there was a line to meet her, but it wasn’t about her health coaching business. They wanted to meet her to talk about how to protect their online business legally.Mind you - Sam barely had an audience at the time. She had around 600 Instagram followers and that was it.Fast forward to today, and she's built a business that has made over $8 million in the last 8 years with the same core products she started with.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedFull deep dive: https://www.joinstation.co/blog/elenasonorangeElena's on Orange: https://www.elenasonorange.comElena's on Orange Instagram: https://www.instagram.com/elenasonorange/Blank Mason Deep Dive: https://www.joinstation.co/blog/blankmasonWhat happens when a Head of Data Science from Airbnb opens an ice cream shop? You get a store with 1,000 potential customers before making a single scoop, flavors tested through Instagram with 10,000 views per post, and a neighborhood hub that became the go-to spot for a 9,000 person community.Elena Grewal opened Elena's on Orange in November 2022, bringing her data scientist mindset to the world of ice cream. Within just seven months, this small neighborhood shop hit $250,000 in annual revenue – all because Elena understood exactly which metrics actually matter.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedDuett: https://duett.coHappy Subscribers Podcast: https://duett.co/blog/new-podcast-welcome-to-happy-subscribers/If I told you someone could create a $12,000 proposal in 8 minutes and get it signed that same day, would you believe me?That's exactly what Allea Grummert, founder of Duett, does regularly as part of her email marketing and copywriting agency for bloggers.But having the ability to close five-figure deals this quickly didn't happen overnight.It took a $5,000 investment in an incubator program, creating one perfect productized service, and valuing long-term relationships over short-term gains.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedFull deep dive: https://www.joinstation.co/blog/geniuslinkGeniuslink: https://geniuslink.comSometimes the best businesses start with solving your own problem. For Jesse Lakes, that problem was losing affiliate commissions from international traffic to his niche extreme sports soundtrack website.That single frustration eventually turned into Geniuslink, a company that has survived four "revenue-cut-in-half-overnight" catastrophes and still emerged as the leading smart link platform for creators.I sat down with Jesse and Shannon, two of Geniuslink's co-founders, to hear the full story of how they bootstrapped this business from the ground up and grew it to over $250k in annual revenue.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedLearn more about franchising Blank Mason here: https://blankmasonfranchise.com/Blank Mason store: https://www.blankmason.comFull Blank Mason Deep Dive: www.joinstation.co/blog/blankmasonThese days, to run a business that provides experiences, you have to make it Instagram-worthy - something people want to share.For Sara Jennetten and Blank Mason, they didn't just make candle making a great experience, they built a business that was Instagram-worthy from Day One.Here's the catch though: Blank Mason only has 4,500 Instagram followers and 400 on TikTok. So how are they driving business from these platforms? Well, let's dive into Sara's story and how she bootstrapped Blank Mason to over $250,000 in annual revenue in just 6 months.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedFor the past 6 months, I've been creating deep dives on how bootstrapped businesses grow from $0 to $250k. While I started noticing patterns, I wanted data to validate these gut feelings.So I spent months digging deeper - analyzing my deep dives, listening to podcasts with bootstrapped founders, and studying "build in public" posts. The result? Research on 64 founders (56 businesses) that reveals who they are, what they built, and exactly how they built it.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedChris & Sara: https://www.chrisandsara.comFull deep dive: https://www.joinstation.co/blog/chrisandsaraIt's not too often someone tries to recreate MTV's Cribs with their van and gets over 1 million views overnight. Yet, that's exactly what Chris & Sara Pochiba did.Here's the thing though - there's a lot more to Chris & Sara's story than just a viral YouTube video. Getting 5 million views on that first video is incredible, but it also created an interesting challenge: how do you actually build a sustainable business from a viral video on YouTube?That's exactly what I wanted to know when I sat down to chat with Chris & Sara about their journey to building a $200k+ business around their YouTube channel.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedDuett: https://duett.coHappy Subscribers: https://open.spotify.com/show/3Y2y92bQE59MwWkU6JATYc?si=baf73e58d22f4ec3If I told you someone could create a $12,000 proposal in 8 minutes and get it signed that same day, would you believe me?That's exactly what Allea Grummert, founder of [Duett](https://duett.co), does regularly as part of her email marketing and copywriting agency for bloggers.But having the ability to close five-figure deals this quickly didn't happen overnight.It took a $5,000 investment in an incubator program, creating one perfect productized service, and valuing long-term relationships over short-term gains.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedWritten Deep Dive: https://www.joinstation.co/blog/autodsLior's LinkedIn: https://www.linkedin.com/in/liorpozin/Lior's Instagram: https://www.instagram.com/liorpozin/AutoDS: https://www.autods.comIn 2016, Lior Pozin emailed his list and said he was going to create 100 videos in 100 days all on the topic of dropshipping. All because no YouTuber would talk about his all-in-one dropshipping platform, AutoDS.There's a lot more to AutoDS's story and growth than just YouTube videos and thankfully, I had the opportunity to chat with Lior about his journey with AutoDS.We talked about how he started AutoDS as an internal software tool to start, how it becoming the "secret" dropshipping tool was key to growth, and how they were recently acquired by Fiverr.To understand the full story of AutoDS, let's start at Lior's journey of becoming a dropshipper.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedLearn more about Kendall & The Candid Collective: https://candidcollective.coMost founders who have built a services business will tell you referrals are the lifeblood of their business. But Kendall Cherry believes referrals are actually holding entrepreneurs back.It's a bold stance, especially considering she's built The Candid Collective into a $20,000/month ghostwriting business. Even more surprising? She did it with just 572 email subscribers.Kendall didn't figure this out right away though. It took four different versions of The Candid Collective before she found what actually worked.Let's dive into how Kendall turned her writing talent into a thriving business, and why she believes the traditional "referrals-first" approach is broken.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedSpringGR: https://www.springgr.comSometimes the best thing an entrepreneur can do is choose themselves over their business.That's exactly what Jermale Eddie did when he made the difficult decision to close Malamiah Juice Bar, a successful Grand Rapids juice bar that he had built from zero to $250,000 in annual revenue in just two and a half years.Let's dive into how Jermale built Malamiah Juice Bar and the growth strategies that led to its success, even though the business eventually closed its doors.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedWeekly Newsletter: https://pages.matthewgira.com/youtubeFull written deep dive: https://www.joinstation.co/blog/insightlimeanalyticsInsight Lime Analytics: https://www.insightlimeanalytics.comMaryBeth's LinkedIn: https://www.linkedin.com/in/marybethmaskovas/"You have no business being employed.” That’s what MaryBeth Maskovas’ future business coach told her the first time she met MaryBeth, the founder of [Insight Lime Analytics](https://www.insightlimeanalytics.com). Insight Lime Analytics is an agency that helps companies with their data strategy. In other words, they help companies measure the right data and then understand what that data is actually telling them. As you may have noticed in that opening quote, starting this agency was a bit of an accident for MaryBeth. It began as a small side hustle that grew to over $3,000 in monthly revenue. By year three, they had made over $1 million in annual revenue.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedFull deep dive here: https://www.joinstation.co/blog/fearlesscommunicatorsFearless Communicators: https://www.fearlesscommunicators.comEduardo Placer: https://eduardoplacer.comBlue Ocean Strategy: https://www.blueoceanstrategy.com/what-is-blue-ocean-strategy/Artists often find it challenging to build businesses, as trading their time or skills for money doesn't come naturally to many of them. They prefer to focus on perfecting their craft rather than worrying about its financial viability. Society can also undervalue or underestimate an artist's earning potential.Yet, artists bring a wealth of entrepreneurial skills to the table. They naturally create content (marketing), constantly pitch their work to shows (selling), and possess a great deal of grit (as they face frequent rejections or critiques).Eduardo Placer, the founder of Fearless Communicators, exemplifies this transition from artist to entrepreneur. With a 15-year acting career under his belt, Eduardo has successfully leveraged his skills, experiences, and unique story to build a public speaking coaching business that is distinctly his own.Through Fearless Communicators, Eduardo has elevated people poised to make the biggest difference, all while building a business with over $700k in annual revenue. Who said you couldn’t make good money by being an artist and a social entrepreneur?

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedRead the full deep dive here: www.joinstation.co/blog/amyporterfieldAmy Porterfield: https://www.amyporterfield.comTwo Weeks Notice: https://twoweeksnoticebook.comCircle's Podcast with Amy Porterfield: https://youtu.be/1p90ADBWUGg?si=DPHUcbSWOwsavtv3Buffer Blog Post: https://buffer.com/resources/law-of-the-double-peak/Email Marketing ROI: https://www.emailmonday.com/dma-national-client-email-report-2015/Amy Porterfield has become the queen of online marketing. She’s the host of one of the top marketing podcasts, Online Marketing Made Easy, and has made over $100 million in total revenue since starting her business in 2009. I had the privilege of seeing Amy speak at ConvertKit’s Craft & Commerce event in 2023 and was given her new book, Two Weeks Notice. When I picked it up, I just took it as “Oh, another business book” and after reading it, that just wasn’t true. It was part motivational but also highly tactical for aspiring and early-stage entrepreneurs. It also led me to this deep dive. How did Amy Porterfield get her first $250k in annual revenue? She discusses it briefly in her book, but not as much as I was hoping for. Thankfully, I was able to read, watch, and listen to a lot of Amy’s content and interviews to learn how she earned her first $250k in annual revenue. 

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedRead the full deep dive here: https://www.joinstation.co/blog/hugoandhobyHugo & Hoby website: https://www.hugoandhoby.comIt sometimes takes a few swings to craft the right product to meet market needs.For Ben Young and Fred Kukelhaus, the co-founders of Hugo & Hoby, it took them a few swings at creating a B2C company by creating a standing desk, a coffee table, and even beds before they finally hit their home run with B2B products.Today, Hugo & Hoby builds custom furniture to create unique spaces, strengthen communities, and better our planet. This all stems from the co-founders’ grandparents, Hugo & Hoby.Hugo & Hoby is almost 10 years old, operating as a 7-figure business, and I’ve had the incredible privilege to watch from the sidelines since nearly the beginning when I met them at Yale in 2015.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedRead the full deep dive here: https://www.joinstation.co/blog/erin-rollenhagenLearn more about Erin and Entrepreneurial Technologies: https://www.entretechno.comIn 2007, everyone was naïve about what was about to happen to the economy.Erin Rollenhagen was no exception—she was equally unaware of the economic turmoil ahead and the challenges of starting a software agency simultaneously.Erin is the founder and CEO of Entrepreneurial Technologies, a software agency with over 20 full-time employees based in Iowa.Yes, the state you might associate only with cornfields and a football team with a questionable offense is home to a highly successful software agency. Who knew?It's been over 17 years since Erin founded Entrepreneurial Technologies. Let's dive into how she started the company and grew it into what it is today.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedLearn more about OnePointFive here: https://www.opf.degreeLearn more about Neil Yeoh here: https://www.linkedin.com/in/neilyeoh/OnePointFive connects and develops Climate Experts in Residence. Today, OnePointFive acts as an agency of Climate Experts in Residence and helps others become those Climate Experts in Residence through their OPF Academy.In just 4 years, OnePointFive earned over $1 million in annual revenue.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedLearn more about Asia Orangio & DemandMaven: Website - https://demandmaven.io/LinkedIn - https://www.linkedin.com/in/asiaorangio/Newsletter - https://demandmaven.substack.com/X - https://x.com/AsiaOrangio“I’m probably more stable” was Asia Orangio’s response to when I asked her “why start your own venture?”. She’s right, she’s more stable than both VC-backed startups she led marketing efforts at before starting her company, DemandMaven. DemandMaven is an agency that helps early stage c-stage companies with growth operations. Another way to think about it is hiring them as a fractional head of growth. This is different than just marketing and demand generation though. As Asia put it, “there are no silver bullets” to growth. Your product and marketing efforts have to both work for growth efforts to really work. DemandMaven has over $500k in annual revenue and Asia has worked with organizations like Moz, Sparktoro, MicroConf, TinySeed, and Techstars.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedLearn more about Terry: https://terryrice.co/ and https://www.linkedin.com/in/terry-rice/Sometimes being fired is a blessing in disguise. For Terry Rice, getting fired from Facebook was one of the best things that happened to him.Within 18 months of being fired from Facebook, Terry Rice developed a consistent six-figure business as a teacher. Today, Terry has become prolific creator by being a contributor for Entrepreneur, an Expert-in-Residence at SPI Media, and is a Managing Director at Good People Digital. Let’s dive into Terry’s story and the tactics for how Terry built a six figure business within 18 months.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedTally's Build in Public posts: https://blog.tally.so/our-bootstrapped-journey-towards-100k-mrr/Tally's Product Hunt Guide: https://blog.tally.so/product-hunt-launch/Two founders launching a travel startup at the beginning of a global pandemic and somehow that leads them to building a company that just makes better online forms?That is the story of Marie Martens and Filip Minev, the duo behind Tally Forms. Marie & Filip have bootstrapped Tally forms to over $1.2 million in annual reoccurring revenue (ARR) today and were able to get to $250k ARR in 20 months.

Download the Bootstrapped Report: https://www.joinstation.co/bootstrappedNathan's ConvertKit Story: https://youtu.be/5bzMHKOMaxY?si=lb3GXFnx4L8bRy0pWritten Deep Dive Here: https://www.joinstation.co/blog/nathanbarryToday, Nathan Barry is the CEO and founder of ConvertKit soon to be Kit. Today, ConvertKit makes over $40 million in annual revenue, has over 80 full time employees around the world, and is completely bootstrapped.There’s a lot of cool stories about how ConvertKit became what it is, but the story I want to focus on is Nathan’s journey from full time employee to creator.This is a journey that Nathan was pretty public about on his blog post and I spent about 20 hours going through all of it so you can potentially implement some of the strategies Nathan used to create his $256,000 business.Full blog post: https://www.joinstation.co/blog/nathan-barrys-growth-tactics-for-a-256k-business