Freelance to Founder is a call-in show helping real-life freelancers grow their businesses and escape the feast-famine lifestyle. The podcast is hosted by Preston Lee, a former freelancer who has started, built, and even sold successful businesses of his own. Preston is joined nearly every weekday by other expert founders, freelancers, and entrepreneurs to help you take your solo business to the next level. You can submit your questions at FreelanceToFounder.com/ask If you enjoy content from…
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After years of leading teams, Kevin wants to go solo — but he's worried about losing the structure and support that came with managing people. Moe Choice, a six-time co-founder turned solopreneur coach, shares the exact moment he realized independence didn't mean isolation, and the three-step framework he now teaches: commit fully to going solo, build a circle of support, and find mentors who are…
Daniel's calendar is packed, his to-do list never ends, and he's starting to wonder if "freedom" was ever real to begin with. Preston and Moe Choice get into a candid, sometimes contentious conversation about the different types of freedom—time, money, mental, emotional—and why loving what you do might matter more than how much of it you're doing. They also tackle a harder question: what happens…
Moe Choice left the co-founder life to build a solopreneur business on his own terms, and now he's helping others do the same. In this episode, he and Preston tackle a question from listener Alex, who feels trapped by his own freelance success. They dig into the mindset shift from bricklayer to cathedral builder, why chasing hours keeps you stuck, and how repositioning your offer around…
Emily has hired contractors before, and it blew up on her—badly enough that she's not sure she can trust the process again. Preston and Kevin Rice, who scaled a business from two people to two hundred, break down why bad hires happen, how to rebuild systems (not just confidence) after getting burned, and why the real fix often has less to do with the contractor and more to do with how you…
Working around the clock and still can't shake the feeling that something's not sustainable—that's exactly where Mark finds himself. Preston sits down again with Kevin Rice, who turned a garage side project into a nine-figure agency exit, to unpack how he knew it was time to stop grinding solo and start building a team. From outsourcing your first project to walking away from clients like Pepsi,…
Jason is building a business he's proud of, working harder than he ever has — but his kids only ever see him working, and he's afraid he's running out of time to change it. Kevin Rice knows that fear firsthand. He scaled his agency from a garage to a nine-figure exit, then discovered his kids had never actually seen him work hard, only felt him absent. Preston and Kevin dig into what it really…
AI just rewrote the rules for getting found, and most freelancers haven't noticed. Charles Gaudet explains how AI tools are quietly building an "expert profile" on every business owner, scraping LinkedIn posts, podcasts, and reviews to decide who gets recommended and who disappears. Preston and Charles talk through what separates authentic, high-consumption content from AI slop, and why 2026 may…
Jordan works remotely and can't seem to shut his brain off—work follows him everywhere, from his bathroom to Bali to a bench under a bridge. Preston and Steven Puri, a former film studio executive and three-time startup founder, break down how to build mental boundaries when you don't have a physical office. They dig into the power of ritual and physical association, sharing a wild story about the…
Anthony just hired his first two teammates and immediately feels the ground shift under him. Solopreneur instincts don't translate to leadership, and he's not sure where his time should go—sales, training, or growing the business. Preston and Steven Puri break down the difference between giving people tasks and giving them goals, and why real leadership means stepping back enough to let your team…
Ethan has been hustling for three years straight, doing everything the internet gurus told him to do—and his business is still just "meh." He can't afford to hire help, and he's starting to wonder if he's destined to stay a burned-out freelancer forever. Preston and Steven Puri, a former film studio executive who's raised over $21 million in venture capital, break down why most online advice is…
Omar is ready to bring on his first virtual assistant, but he's stuck on one question: hire a generalist or go straight to a specialist? Preston and business lawyer Joey Vitale break down when a jack-of-all-trades VA is the smarter first move, when client-facing or technical work demands a specialist from day one, and how to structure that first hire—hours, pay, and processes included—so it…
Melissa is drowning in her own to-do list but terrified to bring on help—what if a new hire messes up a client deliverable or damages her brand? Preston and business lawyer Joey Vitale break down exactly where to start delegating without the risk, from running accountability calls to tracking key business metrics. They dig into how to build trust with a new teammate gradually, why emotional safety…