Breaking Solo

Do you know what AI is telling people about your business right now? Bryan Eisenberg has spent 30 years helping businesses get found, understood, and chosen. He and his brother coined the term conversion rate optimization, wrote New York Times and Wall Street Journal bestsellers, and worked with brands like Dell, Disney, and Google. Today, he'd rather work with owner-operators. In this episode...

What happens when the client you gave eleven years to hits pause without warning? For Jeanne Tan, that moment, along with losing her husband to pancreatic cancer in 2020, forced a hard truth: she'd been running a business while thinking like an employee. In this episode of  Breaking Solo , Jeanne shares how she stopped trading hours for someone else's stability and repackaged her expertise...

What if the thing that keeps your business alive for four decades isn't a niche, a funnel, or a framework — but plain curiosity? Lisa Bastian has been working for herself since the late 1980s. She started Bastian Public Relations while raising a young son, back when a woman who worked from home was too corporate for the playgroup moms and too domestic for the corporate clients. She's writt...

What if the "law of attraction" is actually doing women entrepreneurs a disservice? Donna Price, founder of Compass Rose Consulting, works with women entrepreneurs on building more profitable, efficient businesses that make a bigger impact — for their clients and the world. She went solo after five years managing an outdoor education camp, working 16-hour days with a two-year-old at home...

What happens when a solopreneur's kitchen-table business turns into a national franchise — run by her own daughter? Liz Wahl is president of Young Rembrandts, an after-school drawing franchise that started in 1988 when her mother, a fine arts major with no interest in becoming a business owner, began teaching a handful of neighborhood kids in their living room. Liz grew up watching that grassr...

What if your business could feel the way Disney feels — that unmistakable rush of happiness the moment you walk through the gates? Shaun Whynacht, founder of Blue Cow Marketing, has spent 15 years in marketing automation helping small business owners bring their expertise and their ideal client experience to life through systems, CRM, and AI. He grew up in an entrepreneurial family without even re...

Most overwhelmed entrepreneurs don't need another productivity hack. They need to stop carrying everything themselves. Dortha Hise has spent more than 20 years helping entrepreneurs build clarity, capacity, and breathing room into their businesses through systems, delegation, and strategic support. Her core insight, after two decades in the trenches: people aren't overwhelmed because they...

What if the best sales advice you've ever heard is: stop trying to sell? Diane Helbig has spent 20 years as a business advisor and trainer, working with small and micro business owners on sales, leadership, customer service, and conflict management — all "the people stuff." She went solo after a full-time job started making decisions that weren't in her best interest, and her fat...

There's a story hiding inside every business — even the ones that swear they don't have one. Jen Bullington is a business storyteller who helps entrepreneurs find the six stories buried in their business and use them strategically to shorten their sales cycle and make people genuinely fascinated by what they do. Her path there wasn't a straight line: after years as a corporate software...

What if the thing that makes you unforgettable isn't your polish — it's your story? Dawn Stebbing has spent 16 years as a global image and presence expert, helping women close the gap between blending in and becoming unforgettable. But her real differentiator isn't styling or color analysis — it's her refusal to separate image from mindset, leadership, and the deeper story undernea...

What does it actually take to become "the obvious choice" when AI is now doing the recommending instead of just the ranking? Chuck McKay has spent decades in marketing — starting as a disc jockey and radio ad producer, moving into advertising sales, and eventually walking away from a steady paycheck (after one memorably honest, three-beer conversation with his sales manager) to become an...

What happens when the business you build is born from the hardest thing you've ever survived? Hannah Darby didn't set out to become an entrepreneur — she became one because she couldn't ignore what her own grief journey had taught her. As a holistic healer and grief guide, Hannah blends subconscious therapy, energy work, and counseling to help people heal at the root. But her path to s...

"That's not my job" — five words you'll never hear Scott Keene say. As a serial solopreneur turned professional bookkeeper and payroll specialist, Scott has run everything from a family restaurant and lounge to a pandemic-crushed kayak tour company before finding his true niche: helping business owners who are great at their craft but drowning in their books. In this episode, Sco...

What happens when you close the biggest deal of your life… and feel nothing? That's the question that cracked open this conversation with Harland Merriam — former pastor, military chaplain, and now a real estate investor who facilitates masterminds for high-performing entrepreneurs across Central Florida. After 40+ years serving congregations and the military, Harland "repurposed" (h...

You're never going to have all the time, all the budget, or all the information. So how do solopreneurs move forward anyway — without burning out, without radiating desperation, and without sunsetting the right project at the wrong moment? In this episode of  Breaking Solo , we explore the mindset that carries solopreneurs through the messy middle of building something on their own. Drawing on...

What if consistent, predictable income isn't a personality trait — it's a recipe? In this episode, I sit down with Dan Rochon, real estate agent, sales trainer, host of the  No Broke Months  podcast, and author of the upcoming book  Teach to Sell  (published by Post Hill Press and distributed by Simon & Schuster). Dan has spent the last 15 years documenting the exact framework that get...

What happens when a fifth-generation doctor walks away from one of the most established medical institutions in the UK to rebuild healthcare the way it used to feel? In this episode, I sit down with Dr. Suhail Hussain, a UK-based GP (the equivalent of a family physician in the States) who left the NHS during COVID to launch his own private, home-visiting medical practice. Dr. Hussain shares why te...

What happens when a four-year-old gets a coin pulled out of his ear and decides that's what he's going to do with his life? In this episode, I sit down with Magic Brad — magician, event marketer, and a refreshingly contrarian solopreneur — for a conversation packed with hard-won wisdom, weird brilliance, and one of the most unbothered takes on competition I've ever heard. Brad shares h...

What if the reason your revenue is stuck isn't that you're doing the wrong things — but that you're doing them in the wrong order? In this episode, I sit down with Ken Steven, business growth consultant and creator of the Revenue Growth Readiness Scorecard, for a conversation that genuinely shifted how I think about scaling a solo business. Ken spent years turning around companies stuc...

What do you do when the medical world keeps telling you "it's just hormones" and you know it's something more? In this episode, I sit down with Donna Thorell, founder of Vitality by Donna, who became her own case study after years of being dismissed by doctors — and ended up building an entire holistic wellness practice for women out of what she learned. Donna shares how she lost...

What do you do when a client tells you your entire industry is "churning fluff"? If you're Richard Cook, you let it shake you — and then you use it to reinvent the way you work. In this episode, I sit down with Richard, founder and managing director of London-based B2B PR consultancy Champion Communications, for a conversation that ranges from accidental solopreneurship to running a...

What happens when sheer will gets your business to the point where willpower alone isn't enough? In this episode, I sit down with Beth Sanders, founder of Ballast Ops and a fractional COO who specializes in being the "number two" for founders who've outgrown going it alone. Beth shares why she left full-time work to partner with multiple founders at once, how being EOS-certified...

What happens when you stop waiting for permission and start building because you can see exactly what's broken? In this episode, I sit down with Dr. Sarah Choudhary — PhD in data science, Forbes Technology Council member, and CEO of ICE Innovations — for a conversation that completely reframed how I think about solopreneurship at scale. After 20+ years building AI strategy for 150+ organizatio...

What do a Y2K programmer, a Las Vegas lease-option real estate expert, and a sci-fi novelist building a Marvel-style universe have in common? They're all the same guy. In this episode, I sit down with Kevin A. Dunlap — author, speaker, and creator of the Crimson Alliance Universe — for a wide-ranging conversation about adaptability, perseverance, and what it really takes to keep going when the...

What do you do when your name is all over the internet and every background check becomes a closed door? In this episode, I sit down with Matt Melvin — author of  Bully Behind Bars: A Gay Christian Trump Supporter Goes to Prison — for a raw and deeply personal conversation about accountability, faith, and reinvention. Matt has lost more than a hundred jobs to background checks, walked away from an...