Solopreneur Stories

In this episode I speak with Gregory Foran.  Gregory is the founder of a solo marketing agency called Breakaway Marketing.  After working in marketing leadership positions for over a decade helping to turn poor performers into market leaders and generating over $129M in incremental revenue, Gregory jumped into entrepreneurship.  He and I have some very similar stories, which we talk about, including topics such as: Scaling a business Experiences with subcontractors  Family, fatherhood, and taking time off to focus on those things Building a niche while being adaptive to market signals And other topics. This was a great one, and pretty meaningful for me personally. I mention pretty early in this episode that I felt like I was talking to my own conscience at a few points. His story and the way he shares it hit me in the chest, and I felt like some of our similar experiences make for some good lessons to anyone listening. Gregory is a great guy and I’m rooting for him and what he’s building.  As always it was a great conversation and I learned a lot. And I think you will too. Here is - Gregory Foran.

In this episode I speak with Joe Fitzpatrick. Joe is a fractional CMO who has spent his career working with tech founders who were struggling to attract new customers and who needed to switch their marketing from an ad hoc approach to a strategic, long-term approach. We cover topics including: Understanding the context behind a business’s numbers, and developing strategy beyond a spreadsheet The logistical side of running a one person business Being the voice of reality for your client The challenges of doing marketing for companies that aren’t clear about their broader business strategy What Joe has learned on his path of self-employment, including versions of door-to-door sales early in his career and the humbling lessons roles like that can bring And other topics. Joe was another great guest - a great guy with a great resume and a great story. I love his “throw me in and I’ll figure it out” attitude. I’d encourage listeners to pay attention to his story from his sales roles and how his curiosity and drive made him a top performer. I think anyone listening can extrapolate Joe’s lessons for their own professional journey to bring a willingness to learn and develop opportunities. So I hope you enjoy listening to my conversation with - Joe Fitzpatrick.

In this episode I speak with Trent Warner. Trent is a fractional CMO and the managing director of Strategic Brand Builders. Where he focuses on bringing marketing strategy and systems into businesses to create clear and consistent growth - not marketing whack-a-mole.  We cover topics including: Some of the problems with the agency model of today  Having high expectations of yourself  Trust, the currency of relationships  The importance of strategy Working remotely and the ‘return to the office’ collision Establishing strategies and systems  And other great topics. Trent is an old colleague from a lifetime ago, so it was great to reconnect with him and hear about all of the great stuff he’s doing.  I was personally able to learn some pretty tactical things as takeaways from my conversation with Trent, and I’m betting for other solopreneurs out there you’ll find the same. So don’t miss this one. Here is - Trent Warner.

In this episode I speak with Parul Bhandari. Parul is a Customer Success startup advisor and consultant.   Following a career in ergonomics consulting and in HR, Parul launched her first Customer Success (CS) team from the ground up, and from then on has focused on driving startup Customer Success journeys.   In addition to Customer Success, she is a passionate advocate of all things food and fitness, and of promoting DE&I. We covered topics including: Her initial path to becoming a doctor  Ergonomics  The “build phase” of companies  Launching a community Being a contributor for online publications like Inc. The importance of documentation  And other topics. It was great to speak with someone in the customer success space. We get into the importance of its function and contributing to revenue in businesses, from hiring to developing and other details that can bring this function to life.  If you’re in that space or working with them, you’ll definitely learn some things from Parul. So here she is. Here’s my conversation with - Parul Bhandari.

In this episode I speak with Shailvi Wakhlu. Shailvi is a seasoned Data Leader and Self-Advocacy Expert with over sixteen years of experience building technology products.  She has spoken at nearly 100 global conferences and Fortune 500 events, coached close to 500 individuals, and authored the best-selling book "Self-Advocacy." Which I’ve read and would recommend you read, too. Her career includes notable roles at Salesforce, Fitbit, and as the Head of Data at Strava. We cover topics including: Her experience writing her best selling book, and the supporting speaking engagements she’s done The topic of self-advocacy, which I think a lot of listeners will get a lot of value out of  Her experience building an online course  And other topics. It was a great conversation. Her passion for self-advocacy really comes through. The word authenticity gets thrown around a lot, but when you speak with someone like Shailvi you can really connect with how genuine she is for the work she’s doing and why she’s doing it. I learned a lot. And I think you will too. Here is - Shailvi Wakhlu.

In this episode I speak with Michael Strachan. Michael has served in all roles of digital agency life, starting in the weeds, overseeing cross-channel teams in multiple locations, developing strategy for companies of all sizes including several fortune 500.  He’s since gone on to found Mediaconfidant. The initial market opportunity Michael saw was identifying where data was inaccurate - in his agency life he saw more clients leave due to fights over what the numbers were than actual performance, so he created a tool to identify not only what the issues were but where they came from.   When he showcased it to Google, they put MediaConfidant in their Google Startups for Cloud program at the Scale level and awarded them dev hours to build the next gen of reporting that includes forecasting, data source comparisons, anomaly detection, PII detection, hacking vulnerabilities, and real actionable insights.  Michael is an old colleague and friend and it was great to catch up with him. We cover other topics including: Fatherhood and family  Data vs. insights  Qanon, 4chan, and shady website data  Leveraging AI Setting your own boundaries  And other topics. Please enjoy my conversation with - Michael Strachan.

In this episode I speak with Garrett Jestice.  Garrett is a GTM Strategy consultant and advisor for B2B startups.  Before founding Prelude Marketing, Garrett was the Chief Marketing Officer for Eddy, where he helped build a successful go-to-market strategy that boosted revenue 3x and website traffic 10x in his first 18 months in the role.  I reached out to Garrett to come on the show. He is someone who operates in a similar space and function as I do, and he wrote an open letter to himself on LinkedIn that covered some of his current thoughts on his own future in solopreneurship. If things go well, there seems to be a somewhat inevitable intersection one faces with their solo operation, which includes scenarios like: Hiring more people to grow - which puts you in whole new area essentially running an agency Niching even further and trying to become more of an expert in a single function Do nothing and continuing on the path you’re on You get the idea. Garrett was super easy to talk to. He’s a great guy with a lot of smarts, and there were moments where I felt like I was talking to the voice in my own head with how similar some of our experiences have been. It was a ton of fun, and another conversation I got a lot of lessons and value out of. And I think you will too. So here it is. Here is - Garrett Jestice.

In this episode I speak with Rachel Meltzer. Rachel is a freelance tech writer, writing business coach, and also host of her own podcast, The Guidebook. Rachel and I cover topics including: Working with a business coach as a solopreneur Healthy outside perspectives  Perseverance vs stubbornness  Developing honest internal signals and learning how to trust yourself  Comparison and how to avoid comparing your own joy away And other topics. Since filming, Rachel and I have become pals. We’re both located in New England, Rachel in Massachusetts and myself currently in Rhode Island. We’ve been hosting meetups at some local breweries to connect with other fellow freelancers, consultants, and solopreneurs in the New England area. It’s been a lot of fun - meeting new people, discussing what’s working and what’s not, making introductions to each other’s network, and all the good stuff to help each other learn, grow, and win out there. So if you’re a New Englander, stay tuned for more events - we’d love to see you there. For now, here’s my conversation with - Rachel Meltzer.

In this episode I speak with Christy McCreath. Christy is a seasoned B2B marketing strategist with over 15 years of expertise in revenue marketing. She specializes in Account-Based Marketing strategy and execution, and managed services for ABM tech implementations. Christy brings efficiency and data-driven insights to drive programmatic successes for GTM teams at medium-sized tech companies. We cover topics including: Being a working parent Freelancing and focusing on your craft as a solopreneur The FIRE retire early movement Overemployment Organization as a solopreneur The details of fractional engagements And other topics. Christy was great to speak with. I wanted her on the show to share her story as, to date, I had not had anyone specifically focusing on Account Based Marketing as a solopreneur. For those unaware, doing this requires one to be a veritable one person army - which Christy is. Carrying both technical expertise in different marketing technologies and also business expertise in understanding the big picture strategy a business needs to have in place before committing to an ABM program. She was a ton of fun to speak with and I think you’ll enjoy hearing her story. So, here it is. Here is - Christy McCreath.

In this episode I speak with Gargi Potdar. Gargi is an Agency founder and Solopreneur, at GKP Consulting. She’s a passionate and driven founder and marketing growth consultant who specializes in B2B marketing for startups and scale ups. She’s built successful demand generation growth functions and thrives on aligning sales and marketing to work together and not against each other.  Gargi started her solopreneur journey a little over a year and a half ago so that she could spend more time with her son and make her own schedule.  Probably something that resonates with any fellow or aspiring solopreneurs who might be listening. If so, stay tuned for how we explore that topic. Speaking of topics, we  cover ones including: Being intentional with one’s time as a solopreneur Identifying what’s important in one’s life and honoring it Why Gargi is comfortable billing hourly - something that, at least at the time I’m filming this, I am also comfortable with under certain conditions Networking events and professional growth as a solopreneur And other topics. Apologies to my audience for how I sound in this episode.  I was on the cusp of losing my voice from a cold that made me a bit froggy, so I hope it doesn’t come off as too rough on your ears. Anyway - Gargi was a great guest. I loved her story and really appreciate her taking the time to share it with me. And now it’s shared with all of you - so please enjoy my conversation with - Gargi Potdar.

In this episode I speak with Peter Wilken. Peter is a Madman, Brand Man, Dad-man, Coach-man, Author and Speaker.  He used to run ad agencies, his last corporate role being Head of BBDO Asia Pacific. He also ran agencies for Leo Burnett and Ogilvy before co-founding one of the first specialist Brand Consulting firms, The Brand Company.  Peter continues to consult through his private company, Dolphin Brand Strategy, but increasingly spends his time coaching business owners and aspiring brand strategists and Chief Brand Officers through his online programs at The Lighthouse Brand Strategy Academy. Peter was a great guest. We cover topics including: Superficial brands and substantive brands  Branding vs brand strategy  Golden handcuffs  His experience selling a company  Pakistani royalty  His experience of writing a book, Dim Sum Strategy - which you should check out And other topics. We had a little bit of network challenges while filming. All my fault. But Peter was a total gentleman rolling with it. He has a seriously impressive resume with great, global experience. And he’s out there continuing to do great things with his online academy. I hope you enjoy this conversation as much as I did. So, here it is. Here is - Peter Wilken. 

In this episode I speak with Hilary Swan. Hilary is the founder of Rebel Scout Consulting where she supports founders and CEOs as a fractional sales leader.  From the early days of founder-led sales advisory all the way to a growing sales team in need of leadership and strategy, Hilary has the background, tenure, and nimbleness to hop in and make an immediate impact.  Hilary and I cover topics including: Figure skating  Networking as a solopreneur and asking for referrals and connections Fear setting, which is the reverse of goal setting  Productized services - which was a healthy discussion How Hilary structures her offerings across areas including advisory and fractional engagements And other topics. This was another conversation I’m grateful for, rich with valuable lessons and takeaways. Since filming, Hilary had her live event speaking gig and it appears it was a success - so great work Hilary on bringing that to life - you can hear us get into the details of her preparing to speak later in this episode. So here it is. Here is - Hilary Swan.

In this episode I speak with Leslie Greenwood. Leslie is the founder and CEO of Chief Evangelist Consulting, which provides strategic guidance and insights to organizations looking to build impactful communities.   Before starting her consulting company, Leslie was the VP of Member Success & Member Advocacy at Pavilion, where she built the team and programs that drove membership growth from 2k-10k in two years.  She is also the co-founder of Wednesday Women, an organization that amplifies and spotlights women executives and entrepreneurs.  Leslie and I cover topics including: Putting yourself out there, focusing on what you can control, and allowing the universe to handle the rest Curiosity plus action  The first live, in person event she put on for Wednesday Women The importance of mentors as a solopreneur And other topics. Leslie was great to speak with. We get into her journey, which includes the professional event of at one point being fired - many of us have found ourselves facing that type of event, so you can listen to that chapter of Leslie’s journey in this one. She was a great guest and, as usual, someone I learned a lot from. And I think you will too. Here is - Leslie Greenwood.

In this episode I speak with Gabe Fontana. Gabe is a solopreneur based out of Vancouver, Canada. He helps farms and landscaping companies market their products and services online with web design, SEO, and content strategies. Gabe and I cover topics including: His experience niching as a solopreneur Virtual assistants Doing cold outreach and business development as a solopreneur Working with mentors and coaches as a solopreneur Raising your rates as a solopreneur Some great resources like the “Build your copywriting podcast” and “the comprehensive copywriting academy” And other topics. I love Gabe’s background. You’ll have to listen to the episode to get the full feel for it, but he went from working on a farm to working on his laptop and has picked up really valuable lessons as a solopreneur along the way. There’s also great analogies to his experience in farming and how he’s now running his own business. The seasons, the patience, the labor - it was a lot of fun to explore with him. Gabe and I talk a bit about repositioning and I share some details about what I had recently gone through myself in terms of my services and audiences. All this is to say - this space can move quickly, and I try to keep up with it. So we’ll see how this episode ages and if Gabe and I are still doing in a few months what we’re doing currently. It was a great episode. I hope you like it. Here is - Gabe Fontana.

In this episode I speak with Chipper Watcott. Chipper is the Founder of Whelm – a software platform built specifically for solopreneurs and freelancers to take the administrative headache out of doing great work. He lives in St. George, Utah with his wife, baby boy, and their dog. Chipper started doing freelance design work in 2017, and launched Whelm in 2023 to address the problems he faced as a solopreneur. We cover topics including: Chipper’s experience buying a business Urbanism and working from home Utah’s tech scene Solopreneur side hustles And other topics. I could have kept Chipper on for another several hours. He’s a smart guy with a great story and was a ton of fun to speak with. And I love that he took his own experience, understood the persistent challenges folks in similar roles face, and is out there building something to address it for today's solopreneurs. So for all of you freelancers and solopreneurs in the audience - go check out Whelm. Here is - Chipper Whatcott.

In this episode I speak with Taylor Crane. Taylor is the founder of Fractional Jobs, helping startups reach and recruit fractional leaders (think fractional CMOs, CTOs, Heads of Sales, etc.). He's also the founder of Clubs Poker, acquired in 2023, and before that was a Product Manager for 10 years. Taylor and I cover topics including: Quantifiable goals as a solopreneur The benefits of fractional work and solopreneurship The downsides of fractional work and solopreneurship The 40 hour work week and the industrial revolution And other topics. My conversation with Taylor was a total delight. I’m fascinated by the concept of work. Why we do it. The way we do it. Anachronisms from culture and history and technology that persist despite there being better options. Taylor and I cover all of this. It felt like a really fun philosophical exploration of the notion of “work” - and Taylor is building something with Fractional Jobs to walk the walk he believes in, and I admire that with all my love and respect. He was a great guest, so here he is. Please enjoy my conversation with - Taylor Crane.

In this episode, I speak with Adam Goyette. Adam is the founder at Growth Union, a marketing agency that works with growing B2B start-ups to help them scale faster. He is a former Senior Marketing Executive, who previously led Marketing at Help Scout and Growth at G2 - named one of the Fastest-Growing Private Companies in America by Inc 500 and Deloitte. We cover topics including: Experiencing supportive leaders and CEOs Leveraging your network as a solopreneur Giving away value as a solopreneur Adam’s experiences as a growth advisor and solopreneuer Saying no to clients and ending relationships that aren’t working And other topics. Confession from me - Adam is someone I’ve been following on social media for a while. I’ve looked up to him for a while, at least in terms of vicariously getting to know him through his posts and comments. He’s such a great guy. We had audio issues, which were all my fault, and Adam was a total gentleman as I bumbled my way through things. What Adam is doing with Growth Union is, in my opinion, a real needed shift in the agency and client business model. We get into this in our episode, so you’ll have to check it out, but I’m impressed with what he’s doing and wish him all the best doing it. So here’s my conversation with - Adam Goyette.

In this episode I speak with Morgan Snyder. Morgan is the founder of ThoughtLeaderToday.com, where he helps executives tell their story. We cover topics including: Working at a startup Defining what you want out of your life Surrounding yourself with people doing cool shit The challenges of Credentialism in the market as a solopreneur Confidence as a solopreneur Self discovery, self acceptance, and self compassion And other topics. Utah - you have taken the lead with podcast guests reigning from your state. Something about Utah these days, it is cranking out awesome people I have been getting along with. Speaking with Morgan was a great experience. He’s been on some other podcasts, so definitely check them out. I had before having him on and his personality did not disappoint. So here it is - please enjoy my conversation with Morgan Snyder.

In this episode I speak with Neil Weitzman. Neil is the founder of revenue•x, a revenue advisory providing fractional CRO services. Neil helps early-stage ​and medium-sized businesses build and grow. CEOs call Neil when ok is not good enough. We cover topics including: Family What makes a good fractional leader Companies learning from the mistakes of the market Hiring fractionals before departments How tactical should fractionals get The art of expectation setting And other topics. Neil is an impressive guy. He’s someone I look up to as a voice in the fractional space and the great work he’s doing building a community, Porch, which you’ll hear about in our episode together. Thank you Neil for all of the great information. Neil is someone who for me personally, amidst all of the noise one may encounter on social media, always stands out as having something interesting to say and add to the conversation. And I’m grateful that part of that conversation is what I’m bringing you with this episode. So here it is. Here is - Neil Weitzman.

In this episode I speak with Tory Kindlick. Tory is the founder of Growth Trajectory, a growth marketing consulting company. Prior to his move into the world of solopreneurship, Tory worked as VP of Marketing at Corti (a Healthcare AI company) and Refine Labs (a full-service Demand Gen agency), as well as several demand gen leadership positions at B2B SaaS start-up's. Tory's super power is "figure-it-out-ability", and he's always ready to shift into problem solving mode when his clients or network of B2B marketers need help with GTM motions, RevOps, or customer acquisition strategies. We cover topics including: Sharing your work in the open as a solopreneur Adjusting to working as a solopreneur and developing a rhythm to running your business Imposter syndrome, which I think to date every guest has experienced some form of Leadership Incremental improvements as a solopreneur And other topics. Tory was another fun guest. I learn a lot from everyone I speak with on this show and Tory was no exception - he’s a great guy with a great attitude and it was a total pleasure having him on and hearing his story. So here it is. Here is - Tory Kindlick.

In this episode I speak with Jennifer Baron. Jennifer is a solopreneur and strategic B2B SaaS marketer with decades of experience running successful marketing programs and teams. After a long 20-year career in corporate marketing, she’s now founded her solopreneur operation, Willow and Bee, where she helps tech start-ups grow. We cover topics including: How even after 20-years honing her craft she can still experience moments of imposter syndrome - which I found totally endearing Niching to industries without going overboard niching Resilience as a solopreneur The story behind her brand name and the creative process of branding yourself And other educational topics. She was a great guest, and I love that even after two decades being a corporate professional she’s still embracing the “beginner’s mindset” and being open to learning and developing. I hope you enjoy my conversation with - Jennifer Baron.

In this episode I speak with Ezekial Rochat. Ezekiel is a solopreneur and website designer based in Knoxville, Tennessee. He works with consultants, coaches, solopreneurs, and creators to help them get a website they are proud to share. Ezekiel and I cover topics including: How the origins of his career include a love story Thematic challenges in personal branding for solopreneurs The psychology of personal branding Niching as a solopreneur through experiencing, learning, and adapting Determining your cap for clients and projects as a solopreneur And other topics. I mentioned it during this episode, but this was one of those really valuable conversations for my own professional journey. I’m working on this about myself, but too frequently I can allow some of the industry voices and popular LinkedIn posts get into my head. And while that advice tends to be well intentioned, at least I think it does, what it lacks is a long form examination of the nuance and an unraveling of the anatomy of some of this advice. And Ezekiel and I cover a lot of that in our conversation. So here it is. Please enjoy my talk with - Ezekiel Rochat.

In this episode I speak with Sherehan Ross. Sherehan is a seasoned marketer, recognized for her innovative thinking and ability to challenge the status quo. She has a proven track record of driving revenue, engaging customers, and establishing distinct brand identities in both B2B and B2C markets. Sherhan and I cover topics including: Building a personal brand in public Some of the changes having 2 pandemic babies brought to her life The many challenges of fractional and solopreneur work Hot sauce Leading with empathy and servant leadership And other topics. One of the reasons I wanted to speak with Sherehan is she has been an executive and a fractional leader and solopreneur, and is now open to working with companies as an employee again. Her and I get into some of the specifics that have been influencing her decision. But I want to reiterate as I have previously on this podcast, that a lot of the conversations and advice and lessons that get shared on here are as much for employees as they are for aspiring or seasoned solopreneurs. Like Sherehan, I’ve been very open that, under the right conditions, I am more than willing to become an employee again. And while we see a lot of bad press in the headlines about how rough things can be out there, there are still a lot of really extraordinary companies out there doing great work that offer a ton of rewarding experiences as an employee. So let’s dive into that. Here’s my conversation with - Sherehan Ross.

In this episode I speak with Kate Erwin. Kate went from a B2B SaaS marketer to full-time freelancer and solopreneur in 2023. She's been a copywriter and content marketer for nearly a dozen years. Kate is sharing the raw truth about this transition to solopreneurship on TikTok and LinkedIn. Her content is great. In fact that’s how I found her. Some of it hits spot on, so when I found her I immediately reached out and she was generous enough to come on the podcast. We cover topics including: Thinking of side clients and side income as having lifeboats The challenge and importance of setting the right prices as a solopreneur TikTok for solopreneurs The attitude clients can take to make solopreneurs feel more deeply part of their organization Good clients, bad clients, and cultivating client relationships as a solopreneur The importance of good briefs and good direction for solopreneurs And other topics. Kate was a lot of fun to speak with, we had a lot of laughs and I learned a lot from her story. Give it a listen, because I think you will too. Here is - Kate Erwin.

In this episode I speak with Simon Mills. Simon is a growth consultant and solopreneur at George St. Growth, where he works with B2C Seed to Series A startups as a fractional head of growth. Outside of work, you can find him playing water polo or traveling somewhere warm to escape the cold. Simon and I cover topics including: Digital nomadism as a solopreneur The importance of trial and error as a solopreneur Listening to feedback and signals from the market and clients Getting comfortable putting yourself out there on social media and developing your voice in front of an audience And other topics. Simon was a ton of fun to chat with. He’s making a trip to the New York City area this year. There are a lot of folks in that area that I’m well overdue to link up with, so hopefully Simon and I will go from podcast friends to in real life friends when he’s visiting. Until then, I hope you enjoy this conversation as much as I did. Here is - Simon Mills.

In this episode I speak with Ari Mason. Ari is a Utah-based fractional CMO and business consultant who is on a mission to humanize the workplace.  She’s a former journalist and a storyteller at heart.  Ari builds disruptive brands that turn purpose into profit through authenticity and emotional connection. Ari and I cover topics including: The Utah tech scene and silicon slopes New undertakings as a solopreneur Emergent, organizational culture  The shortcomings of individual contributor paths and paths toward solopreneurship Integrating culture into go to market And other topics. It was another fun episode. I think San Diego and Utah are now competing for where most of my guests are based, so it’s really great to be having these conversations with today's solopreneurs and building these relationships with brilliant folks out there who I hope to one day meet in real life. All of that aside, I hope you enjoy this episode as much as I did. Here is - Ari Mason. ========== Are you a freelancer who wants to focus on the work that actually gets you paid? Whelm handles all of the necessary but boring and time consuming administrative work so you can focus on the work that you love and makes you money. You can create invoices, receive payments, generate client contracts, manage projects, and collect vital client feedback. All in one, simple platform. Check it out with my link here.

In this episode I speak with Erin Simmons. At the time we filmed, Erin was less than a month into their freelance and solopreneur journey as an events and community manager. Erin is an old friend, and someone I wanted to speak with right at the beginning of their journey.  After a collective decade worth of agency work and 4 years across various in-house brands, Erin is using the upcoming year to chase after connection and joy with every professional and personal opportunity they choose to work on. Erin and I cover topics including: Why in-person events are so important  Finding community and what it feels like when you’ve found it Developing a work cadence across multiple time zones How Erin will be helping me with a GPT model - which was an idea they came up with on the fly that totally won me over And other great topics. It was a ton of fun catching up with Erin, and their perspective on following their heart into this next season of life of theirs really resonated with me. And I think it will with you too. Here is - Erin Simmons.

In this episode I speak with Nancy Chu. Nancy is a Product Management Leadership and Solopreneur Coach, whose mission is to develop the courage of product leaders to reach their goals faster, and tech employees to make their first $10k months outside of corporate. Nancy has accumulated nearly 2 decades of experience in engineering and product management, building products for hundreds of millions of users generating tens of millions in revenue across her roles at companies like Meta/Facebook and Roku.  We cover topics including: Toxicity in the workplace and overcoming traumatic workplace experiences The connection of mental health and physical health for solopreneurs and employees Her experience with the forum Blind Livestreaming with Buddhist master teachers And other topics.  Nancy was such a pleasure to speak with and we hit some really deep topics. What I love about conversations like these is that, as much as some of Nancy’s story and advice can be applied to solopreneurship, its application really finds itself squarely talking about life and our own psychology. It was another great discussion where I learned a lot from her story, journey, solopreneurship, and life lessons. And I think you will too. Here is - Nancy Chu. ========== Are you a freelancer who wants to focus on the work that actually gets you paid? Whelm handles all of the necessary but boring and time consuming administrative work so you can focus on the work that you love and makes you money. You can create invoices, receive payments, generate client contracts, manage projects, and collect vital client feedback. All in one, simple platform. Check it out with my link here.

In this episode I speak with Lala Cooper Carver. Lala is a Content & Communications Consultant, with an extensive background in brand identity, communications, and content. She’s partnered with some of the biggest names in consumer tech, healthcare, energy and publishing over the past decade. Lala launched her micro-business, Goldline Content, in September 2021. Since then, it's grown rapidly, and currently supports a wide range of businesses and organizations in the UK and around the world. Lala and I cover topics including: The benefits solopreneurs can have coming from an agency background and wearing different hats Accepting the challenges of solopreneurship and focusing on solutions Jumping in, taking action, and being bold as a solopreneur The importance of saying no to things, but also the challenge of embracing a no mindset as a solopreneur Burnout, being aware of it and being empathetic about it And other topics. We talk about perspectives that are as much for employers as they are for solopreneurs.  While the primary audience of this podcast is aspiring or seasoned solopreneurs, a lot of this advice is very actionable for employers out there looking to learn from those who have gone out on their own and why they’ve done so. I’ve said on this podcast before that I am personally 100% open to being an employee, but that employer would have to meet certain criteria - and the bar seems to remain low for a lot of corporations out there, so I hope some of the perspectives discussed with my guests may get through to anyone willing to listen. So I hope you enjoy my conversation with - Lala Cooper Carver.

In this episode I speak with Tim Hillison. Tim is the Founder & CEO of Entry Point 1.  He’s launched over $1B in products and campaigns for some of the world’s most recognized companies like Visa, Microsoft, and PayPal, and led global go-to-market strategy in the US, EMEA, and APAC for PwC and Cognizant.  Currently, he helps scale B2B startups and transform scaleups into enterprises. Tim was a ton of fun to speak with. We cover topics today's solopreneurs will find a lot of value from, including: The myth of linear career paths  Some of the limitations put on specialist roles  Stoicism and the works of Epictetus Growth at all costs Web 1, 2, and 3 and career 1, 2, and 3 Some thoughts I really enjoyed regarding modern business, and where there’s a gap in satisfying modern life needs And other topics. Tim is someone I’ve been in touch with a few times outside of the podcast, and he’s just a great example of how generous some folks are in the solopreneurship space who is out there working to make the pie bigger and support everyone winning. It’s really great. I learned a lot, and I think you will too. Here is - Tim Hillison. ========== Are you a freelancer who wants to focus on the work that actually gets you paid? Whelm handles all of the necessary but boring and time consuming administrative work so you can focus on the work that you love and makes you money. You can create invoices, receive payments, generate client contracts, manage projects, and collect vital client feedback. All in one, simple platform. Check it out with my link here.

In this episode, I speak with Tenisha Griggs. Tenisha is a solopreneur, agency founder, and public speaker. As part of her solopreneur journey, she’s launched 37X, a digital marketing agency catering to B2B and e-commerce brands. She’s a former All-American track and field athlete, has been recognized as 'Advertiser of the Year' by ADWEEK, and is a sought-after speaker, where she shares her expertise on leveraging AI, digital advertising, and championing diversity, equity, and inclusion initiatives in the ever-evolving marketing landscape. Throughout our discussion, Tenisha shares valuable insights on the ups and downs of her journey as a new solopreneur, offering tangible advice for fellow solopreneurs who can be successful on their own journey. We explore topics including: The importance of personal alignment in goal-setting,  The art of networking and winning clients,  And the transformative power of continuous daily improvement inspired by the works of James Clear and his book, Atomic Habits. But that's not all – we also delve into the wisdom of proverbs and Buddhist parables, adding a lot of emotional depth and richness to our conversation. This episode is a treasure. Tenisha is a total professional, and her dedication and expertise really comes to life as she shares her story, experience, and wisdom. I hope you enjoy my conversation with - Tenisha Griggs. ========== Are you a freelancer who wants to focus on the work that actually gets you paid? Whelm handles all of the necessary but boring and time consuming administrative work so you can focus on the work that you love and makes you money. You can create invoices, receive payments, generate client contracts, manage projects, and collect vital client feedback. All in one, simple platform Check it out with my link here.

In this episode I explore the world of solopreneurship with Nick Lafferty, Growth Consultant and Founder of Early Exit Club.  Nick shares his backstory, insights, and experiences on his journey of quitting his job to pursue his solopreneur dreams. We get deep into some of Nick's areas of expertise, the challenges and highlights of his solopreneur venture thus far, and the backstory on his work with digital products, including The Competitive Conquesting Playbook and Notion templates. Nick shares some of his personal strategies for success, from the power of journaling and positive affirmations to the significance of a compelling personal positioning statement.  Nick also fearlessly and transparently opens up about sharing his personal finances with his audiences and what other solopreneurs should consider when doing the same. Nick is a wealth of knowledge and someone who is thriving in this era of fractional work and solopreneurship. The topics we cover are essential for aspiring and seasoned solopreneurs, with tactical insights and actionable advice others can leverage to grow their brand and pursue solopreneurship success. ==================== Are you a freelancer who wants to focus on the work that actually gets you paid? Whelm handles all of the necessary but boring and time consuming administrative work so you can focus on the work that you love and makes you money. You can create invoices, receive payments, generate client contracts, manage projects, and collect vital client feedback. All in one, simple platform Check it out with my link here.

In this episode I speak with Shirin Shahin. Shirin is a seasoned solopreneur who has worked in product marketing for over 10-years both at larger enterprise companies like Constant Contact and Brightcove, and then as a founder and consultant for herself, which she’s been doing since 2019. She works with primarily B2B organizations of all sizes who are either starting to build their product marketing foundation or expanding on it.  In our conversation we covers topics including: What it was like transitioning from large companies with large teams to her own company as a solopreneur of one WeWork and what it's like as a solopreneur working in public spaces Her experiences in mentorship with organizations like Tech Stars Productized services and some common misconceptions And other great topics. We have a lot in common and this was a really fun episode, so I hope you’ll learn something and enjoy my conversation with - Shirin Shahin. ========== Are you a freelancer who wants to focus on the work that actually gets you paid? Whelm handles all of the necessary but boring and time consuming administrative work so you can focus on the work that you love and makes you money. You can create invoices, receive payments, generate client contracts, manage projects, and collect vital client feedback. All in one, simple platform Check it out with my link here.

In this episode I speak with Rachel Kumar Cross. Rachel is a brand strategist, culture consultant, and marketing communications expert. She’s worked with global companies across industries including Google, Qualcomm, Intuit, and more. We cover topics including: How her first taste of working from home piqued her interest in working for herself  Cognitive dissonance and what it feels like working on projects one doesn’t believe in  Defining A and B and C clients - what that means and how to prioritize who you work with And how setbacks from injuries forced her to be intentional about slowing down and evaluating the work she was doing She was a really great guest, another one I’ve had on from San Diego that’s made me miss being out there. If I have a few more San Diegans come on we may need to host a meetup out there. Anyways, Rachel was a pleasure to speak with and I hope you learn as much as I did.  I hope you enjoy my conversation with - Rachel Kumar Cross.

In this episode I speak with Tracy Laranjo.  Tracy is a Fractional Head of Conversion Rate Optimization and Experimentation who builds high-performing optimization programs for direct-to-consumer brands and agencies. She was Experiment Nation's #1 Must-Meet CRO in 2023, one of Kameleoon's top experimentation influencers from 2022 to 2023, and the former co-host of “From A to B,” the experimentation podcast. She is an advocate of neuroinclusion in the workplace and openly shares her experiences as a woman with ADHD, which we touch on in our conversation. She was a great guest, and we covered topics including: Self-care, self-reflection, and self-awareness  Living intentionally Avoiding playing the short game and building value beyond immediate gratification The importance of word of mouth while being mindful of developing outbound sales motions Rejection and not taking things personally And other topics. Tracy was a ton of fun to speak with. We covered some deep topics and her journey really resonated with me. And I think it will with you too.

In this episode I speak with Dylan Cinti. Dylan is the co-founder of Yarrow, a real estate firm dedicated to enlivening historic properties in Ypsilanti, Michigan.  We cover topics including: How his experience in marketing agencies and leading creative teams led him to founding his company A refurbished, healthier way of thinking about ‘resilience’  Taking time to reflect on and understand one’s values, and then align our working lives towards those values The importance of community and peers and creating a brand identity And other topics it was great to discuss with him. Dylan wasn’t shy about including how mental health was one reason he began reconsidering his career path. It’s something I’m sure a lot of listeners can relate to, myself included. So you can hear all of that and more in my conversation with - Dylan Cinti.

In this episode I speak with Garren Glachman. Garren is the Founder of Follower Fuel, an Instagram marketing agency that connects businesses with real people to boost brand awareness and increase sales.  Garren and I cover topics including: The non-negotiables for setting yourself up for success, like exercise and time management Prioritization Niching in one category before moving to adjacent categories Leveraging systems and more efficient processes to free up time, and then reinvesting that time into high leverage activities The difference between “more” and “better” And other topics. Garren was a great guest and is doing really cool things in the social media space, so definitely check him out. So I hope you enjoy everything he and I speak about.

In this episode I speak with James Ricks. James is the Co-founder of Consulting Launchpad. A one-on-one mentorship program for solopreneurs looking to explore a new side-hustle or fully commit to building a 9-5 business. He’s also a Fractional Director of Marketing and the creator of Prepare My Legacy, a product he created to help families document legacy will information as part of their estate planning. In this conversation, James and I cover topics including: James’ experience doing door-to-door sales and how it taught him he could accomplish hard things How his intentions to land a position in Germany put him on his path to solopreneurship Some of the consistent sticking points he sees new solopreneurs encounter and how he helps them get unstuck And other topics. James was a fabulous guest. In his businesses there’s this theme of helping others get through challenges which I think is just a great calling that James has shaped his life around.

In this episode I speak with Emily Amos. Emily is the founder and CEO of Uplift Content, a content marketing agency that writes case studies, ebooks, white papers and blog posts for high-growth B2B SaaS companies.  Emily and I had a great conversation, that covered topics including: The importance of building meaningful relationships with customers, partners and peers inside the content and customer marketing communities  Her journey from solo operator to running an agency of freelancers How her background in linguistics lent itself to developing clear content for clients Some of the hardest challenges she’s encountered, and how thinking with a profit first mindset has helped The importance of unique perspectives in differentiating yourself And other topics.  It was a lot of fun to speak with her. Like a lot of my guests, Emily gave me a lot to think about and I came out of our conversation feeling like I learned some valuable lessons. And I hope you’ll feel the same way.

In this episode I speak with Raul Hernandez Ochoa. Raul is the founder of Do Good Work, where he partners with founders to deliver profitable growth. He’s also the author of ‘Growth Plan,’ where he shares his blueprint of how he designs revenue engines, and is working on his second book. He’s also a speaker, trainer, and has his own podcast which also carries the name ‘Do Good Work.’ We cover topics including: The importance of developing communication, including communication with yourself and your inner dialog Confidence - you may be surprised by Raul’s response like I was when I asked him to talk about confidence Addressing self-limiting beliefs and living into your potential Documenting your wins to remind yourself what you’ve capable of achieving And other topics it was great to discuss with him. Raul was great to speak with and his wealth of knowledge in all of these topics really came through. It was a ton of fun to have him on. I hope you enjoy my conversation with - Raul Hernandez Ochoa.

In this episode I speak with Jon Itkin. Jon is the Principal of In The Kitchen where he provides positioning, messaging, and brand work for growth stage tech companies and tech enabled services. In this episode we cover topics including: The skillsets he developed early in his career he brought into launching his own operation The importance of diagnostic and technical work including writing scopes, estimating projects, and how essential it is to develop systems for the back of the house of your business The difference between first principles and frameworks, and the importance of repeatable processes without becoming overly reliant on them We also developed a few new hashtags on the fly. Jon is a total wealth of knowledge. This was a great, fun conversation. I learned a lot hearing him share his perspectives and experience, and I think you will too.

In this episode I speak with Amanda Berg. Amanda is a fractional head of growth, helping consumer startups launch, analyze, scale, and optimize their marketing programs.  We cover topics including: The distinction between fractional and freelancer roles and how she embeds herself into her client’s businesses The importance of identifying the right problems to solve before committing to business investments like full-time hires Some of the important lessons she’s picked up in her first year as a solopreneur And other really interesting topics. She has a really honest reflection on some of the lessons she’s taken away and how she’s learning and improving and getting 1% better every day by taking ownership and continuing to build her business and add value to her clients.  She’s a newly minted transplant to the Denver area, so if you’re in the business and want to meet your new neighbor please hit her up.

In this episode I speak with Heidi Hattendorf. Heidi is an innovative commercial leader who’s worked with top brands and now leads her own business, Transformation Insights.   She guides companies in marketing, go-to-market strategies, and business transformation through fractional CMO consulting, operationalizing strategy to execution, and business coaching.  She’s a thought leader, frequent speaker, and influential voice shaping the industry. She’s been named as one of the 'Top 40 Women in Innovation’ by Front End of Innovation; Top 100 Executive Leaders by Diversity MBA magazine, and the eWOW Global award for inspiring future leaders.  She also holds 2 patents for innovations in software solutions.  If that sounds like the resume of someone with rich, experienced, compelling points of view to share - trust your instincts, and you’re in the right place.

In this episode I speak with Vince Moreau. Vince is the Founder and CEO of ScaleCrush, where he helps B2B software companies double their revenue from Google with short-term SEO projects. Vince and I share a lot in common with our business and marketing philosophies, and his wealth of knowledge really comes through as someone who has experienced growing his own operation. His origins in Upwork and how he grew his freelance business  Learning to be comfortable with the uncertainties one faces Having a clear process to solve problems for clients And a lot of other really great topics I hope you enjoy this conversation as much as I did.

In this episode I speak with Savannah Boone Allen. Savannah is founder and CEO of Boone Consulting, the author of ‘The Art of Adaptation: How to Tackle the “Now What” of Life' and is in the process of writing her second book, and she’s also the director of ‘The Boone Podcast,’ the popular baseball podcast that gives listeners a look behind the curtain they don’t get on channels like ESPN. She has a lot going on and is handling it all with grace like a total pro. She was a great guest and we cover topics including: The power of disciplined habits in reaching your goals The importance of a smooth client onboarding and setting the right expectations Learning by doing  And other topics She’s doing really cool stuff. So I hope you enjoy hearing all about it in my conversation with her.

From time to time I plan on doing some solo episodes where I talk about some things on my mind I think you’ll find useful. And this is one of those times. In this episode I point out the misconceptions of the phrase "it's who you know" when it comes to developing relationships.

In this episode I speak with Chris Konowal. Chris is a growth partner to businesses looking to grow their paid media programs, among other things. I really enjoy Chris’s perspective on understanding a client’s entire business before prescribing tactics. In our conversation we cover topics including: What he’s learned in his first chapter of self-employment How he was very intentional about setting up an off-ramp from the world of employee to the world of solopreneur, and how he’d advise others consider the same How he approaches operational roadblocks and leans in as a partner to his clients to deliver real progress Chris has a very clear approach to what he’s doing. While he’s on the earlier stages of his solopreneurship journey he has the philosophy, work ethic, and hard skills to continue doing really great work out there.

In this episode I speak with Jeff Baker. Jeff helps small businesses generate revenue with fractional CMO services, emphasizing their SEO and analytics programs. He’s also co-founder of Beach Commute, where he helps job candidates find authentic remote employment.  Jeff also runs a mezcal review site and, like a true entrepreneur, is involved with a few other interesting ventures. Jeff is a great friend, and we covered topics including: His digital nomad lifestyle and how he balances work commitments with travel Criticisms of the “return to office” movement and its effects on productivity How Jeff manages a portfolio of businesses and how one can pursue similar interests Jeff will no doubt be on again soon to share his latest ventures, travels, and stories as he continues growing his business.

In this episode I speak with Silvi Specter. Silvi is a marketing consultant who specializes in the ground floor of start-up marketing strategies, helping founders build go-to-market strategies from scratch. She’s also a founder herself of Growth Tribe, a private Slack community for marketing freelancers. Silvi is a friend and always great to speak with. In our conversation we cover: Her days in the Israeli startup scene as one of the first 25 employees at Lemonade What it was like starting her journey as a first time solopreneur How she manages expectations with clients with the help of clearly articulated contracts We spend a good amount of time exploring a balanced life, taking care of oneself and mitigating burnout. Something we both had a lot of thoughts on. I loved this conversation.  She was a great first guest to have on the podcast, and I’m sure we’ll reconnect on here again soon.

Welcome to Solopreneur Stories - the podcast that examines the best insights other solopreneurs have already figured out so you can use them in your life. On this show, I speak with guests ranging from brand new consultants to seasoned solopreneurs, and passive side-giggers to hardcore hustlers. We’ll discuss the ideas, the opportunities, and the strategies that they’re taking advantage of so all of you listening can do the same.