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PODCAST

Freelance to Founder

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

business entrepreneurship

All Episodes

19:11

Red Flags Every Freelancer Should Know Before Signing

Freelance to Founder ·

2026/09/08

Rashid is ready to take on international clients, but he keeps hesitating over how to protect himself if a contract dispute crosses borders. Preston and Austin argue that a contract isn't really about winning in court — it's about setting expectations before the work even begins. They walk through the deposit rules, red flags, and reference checks that keep freelancers from getting burned, whether their next client is down the street or halfway around the world.Support our show sponsors ->

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22:53

How Do You Price Yourself Without Underselling?

Freelance to Founder ·

2026/09/07

Aisha wants to charge what she's worth, but like most beginner freelancers, she isn't sure where to start. Preston Lee and Austin Church tackle the age-old pricing question head-on, walking through the pitfalls of using your old salary as a benchmark and the trap of pricing based on what your freelance friends charge. They introduce two numbers every freelancer needs — a survival rate and a dream rate — and explain how packaging your work, not just your hourly rate, can be the difference between

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19:09

Success vs Family: Do You Have to Choose?

Freelance to Founder ·

2026/09/04

Jenna wants to grow a successful business without losing the family life she cares about most. Preston and business strategist Dawn Andrews dig into what it actually takes to build a career on your own terms, separating true values-based decisions from the guilt so many ambitious women carry. They swap real stories, from raising kids while running a business to blocking off six weeks of vacation and building the year around it, landing on one clear idea: your work should fit your life, not the other

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20:35

Freedom Vs Control: Can Founders Have Both?

Freelance to Founder ·

2026/09/03

Somewhere between freelancing solo and running a full team, Nicole lost the freedom she built her business for in the first place. Preston and Dawn Andrews unpack the messy middle of management, where leaders mistake a process problem for a people problem, and share a simple, collaborative way to build standard operating procedures your team will actually use. From word-vomiting your vision into AI to running a low-stakes test before it matters, this episode is a roadmap back to the freedom Nicole

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17:26

Why "Fake It 'Til You Make It" is Bad Advice

Freelance to Founder ·

2026/09/02

Amanda is leading a team for the first time, and every meeting feels like an audition. She second-guesses her ideas, questions her own qualifications, and can't shake the sense that eventually everyone will figure out she doesn't belong in the room. Should she wait until she feels ready, or lead anyway? Preston and business strategist Dawn Andrews unpack why vulnerability builds more trust than having all the answers, how taking strategic risks quiets imposter syndrome over time, and why the leaders

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24:11

Is Sole Proprietor the Right Path?

Freelance to Founder ·

2026/08/28

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

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16:15

3 Questions That Fix Your Finances

Freelance to Founder ·

2026/08/27

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 ->

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20:12

Freelancers and 401Ks

Freelance to Founder ·

2026/08/26

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

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18:03

Is Work-Life Balance a Fairy Tale?

Freelance to Founder ·

2026/08/25

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 ->

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20:38

One Year In, Zero Clients... Give Up?

Freelance to Founder ·

2026/08/24

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 ->

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19:14

From $500 to 7-figure Business

Freelance to Founder ·

2026/08/21

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

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18:40

Is Downsizing Smart?

Freelance to Founder ·

2026/08/20

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

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25:39

"I Thought I'd Have More Freedom"

Freelance to Founder ·

2026/08/19

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 ->

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21:42

The Positioning Shift Will 2X Your Rates

Freelance to Founder ·

2026/08/18

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

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18:34

The Real Reason Your Contractors Keep Failing

Freelance to Founder ·

2026/08/17

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 ->

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19:45

Parable of the Paintbrush

Freelance to Founder ·

2026/08/14

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

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21:55

Business vs. Family: What's the answer?

Freelance to Founder ·

2026/08/13

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

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34:52

This Content Strategy Doubled His Pipeline

Freelance to Founder ·

2026/08/12

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 ->

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14:47

Struggling to Turn Off Your Brain?

Freelance to Founder ·

2026/08/11

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

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20:01

Deep Work vs. Busywork

Freelance to Founder ·

2026/08/10

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

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