BusinessEntrepreneurshipEducationSelf-Improvement

Freelance to Founder

Millo

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 shows like The Futur, Being Freelance, The Accidental Creative, Smart Passive Income, or The Side Hustle Show, then you'll love Freelance to Founder.

Join us every weekday to take the next step on your journey from ... freelance to founder.

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31 episodes
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Avg 19 min
English

Episodes 31

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Friday · 24 min
Is Sole Proprietor the Right Path?
Jason wants out of his LLC. Between renewals, state fees, and filings, it feels like the paperwork is running his business instead of the other way around. Preston sits down with international tax lawyer Bobby Casey to make the case for sticking with it, and for finally outsourcing the parts that are draining his time and energy. They cover the liability protection most freelancers underestimate, the privacy risks of registering an entity yourself, and the cheap, automated tools that can take renewals, bookkeeping, and compliance completely off a founder's plate. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
Thursday · 16 min
3 Questions That Fix Your Finances
Growth sounds great until you realize you can't actually explain your own finances. That's where Parker finds himself—profitable, but nervous about scaling without a handle on his numbers. George Thomas, a financial coach with 15 years of experience, walks through the exact order of operations: get a CPA, forecast your revenue monthly, and routinely interrogate your expenses. It's a practical roadmap for any freelancer wondering if they're ready for the next level. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
Wednesday · 20 min
Freelancers and 401Ks
Arav is doing the math freelancers dread: no employer match, no automatic 401k, and a growing business that seems to pay off faster than any stock ever could. Preston and financial coach George Thomas dig into where retirement planning fits for someone building their own income, unpacking net worth, investment timing, and why a Roth IRA might be the most underused tool in a freelancer's financial toolkit. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
Tuesday · 18 min
Is Work-Life Balance a Fairy Tale?
Lauren's business took off right after she became a parent, and now she's caught between two things pulling at her time. Should the business get the same energy that made it grow, or does motherhood come first? Preston and Lindsay Pinchuk, who built her own company while raising kids, unpack why "balance" is the wrong goal entirely and what to focus on instead—setting boundaries, learning to say no, and asking for help before you're forced to. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 24 · 20 min
One Year In, Zero Clients... Give Up?
Nicole is staring down a decision a lot of new business owners face: stick it out or go back to corporate. Preston and Lindsay Pinchuk share the exact email and LinkedIn strategy that took Lindsay from zero revenue-generating clients to three in under two weeks, plus honest talk about the timeline it really takes to know if a business is working. If you're wondering whether you gave your business enough of a shot, this episode is for you. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 21 · 19 min
From $500 to 7-figure Business
Amanda wants to grow her business without giving up equity, but every dollar feels precious right now. Preston and Lindsay Pinchuk dig into the real framework for deciding what's worth paying for—hiring help before it feels affordable, testing software before committing to it, and even outsourcing chores at home to buy back time. Lindsay draws on her own journey from corporate burnout to building a community that reached three million people a month, showing Amanda how the smallest early investments can create the biggest returns. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 20 · 18 min
Is Downsizing Smart?
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 living the specific life you want. Preston and Moe unpack what nobody tells you about trading a team for total ownership of your time. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 19 · 25 min
"I Thought I'd Have More Freedom"
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 when you have kids, bills, and a runway that's running out fast? Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 18 · 21 min
The Positioning Shift Will 2X Your Rates
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 outcomes—not tasks—attracts bigger clients who trust you enough to leave you alone. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 17 · 18 min
The Real Reason Your Contractors Keep Failing
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 communicate, onboard, and follow through. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 14 · 19 min
Parable of the Paintbrush
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, this episode is a real look at the risk, discipline, and timing behind turning freelance income into an actual company. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 13 · 21 min
Business vs. Family: What's the answer?
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 means to balance ambition and fatherhood, why "they won't remember anyway" is a dangerous excuse, and how intention — not hours — is what actually makes kids feel like they matter. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 12 · 34 min
This Content Strategy Doubled His Pipeline
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 leave zero room for the average, generic freelancer. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 11 · 14 min
Struggling to Turn Off Your Brain?
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 writers of Independence Day and a $5 million villa, to explain exactly how top performers train their brains to switch into—and out of—deep focus. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 10 · 20 min
Deep Work vs. Busywork
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 actually lead. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 7 · 17 min
3 Years. Still Broke. Here's Why.
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 worthless, how to tell if you're solving a painful enough problem, and where to actually find mentors who've done the thing instead of just talked about it. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 6 · 20 min
Most Common VA Question
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 actually sticks. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 5 · 15 min
Evil VA?
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 matters just as much as task lists, and how to know when you're ready to hand off bigger, client-facing work. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 4 · 18 min
The #1 Burnout Cure
Keisha's agency is growing, but everything still runs through her—and she's starting to wonder if that's sustainable. Should she form a bigger legal structure before she hires, or is the real question strategic instead? Preston and business lawyer Joey Vitale break down the difference between hiring employees and contractors, why "bottom-up" hiring often beats bringing on expensive experts too soon, and how to build a team that can run without you—even while you're on vacation. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
August 3 · 19 min
Big Contract Oops
Hannah's freelance business is growing—bigger clients, bigger opportunities, and bigger risk. She's still working off handshake deals and email threads, and she wants to know exactly when a real contract becomes non-negotiable. Business lawyer Joey Vitale joins Preston to break down why a contract isn't just legal armor, it's a communication tool that sets expectations, prevents scope creep, and keeps every client relationship on solid ground. They dig into the most common contract mistakes freelancers make, from generic templates to a simple LLC naming error that could put your personal assets on the line. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠ Join our FREE online event -> ⁠https://10Xfreelance.com/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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