Freelance to Founder

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 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.

Episodes

Success vs Family: Do You Have to Choose?

September 4, 2026 • 19 mins
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, lan...
Listen
Watch
Mark as Played

Freedom Vs Control: Can Founders Have Both?

September 3, 2026 • 20 mins
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 befo...
Listen
Watch
Mark as Played

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

September 2, 2026 • 17 mins
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 st...
Listen
Watch
Mark as Played

Is Sole Proprietor the Right Path?

August 28, 2026 • 24 mins
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...
Listen
Watch
Mark as Played

3 Questions That Fix Your Finances

August 27, 2026 • 16 mins
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 wonder...
Listen
Watch
Mark as Played

Freelancers and 401Ks

August 26, 2026 • 20 mins
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...
Listen
Watch
Mark as Played

Is Work-Life Balance a Fairy Tale?

August 25, 2026 • 18 mins
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...
Listen
Watch
Mark as Played

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

August 24, 2026 • 20 mins
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 f...
Listen
Watch
Mark as Played

From $500 to 7-figure Business

August 21, 2026 • 19 mins
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 thre...
Listen
Watch
Mark as Played

Is Downsizing Smart?

August 20, 2026 • 18 mins
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 ...
Listen
Watch
Mark as Played

"I Thought I'd Have More Freedom"

August 19, 2026 • 25 mins
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, bill...
Listen
Watch
Mark as Played

The Positioning Shift Will 2X Your Rates

August 18, 2026 • 21 mins
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 bigge...
Listen
Watch
Mark as Played

The Real Reason Your Contractors Keep Failing

August 17, 2026 • 18 mins
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 thro...
Listen
Watch
Mark as Played

Parable of the Paintbrush

August 14, 2026 • 19 mins
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...
Listen
Watch
Mark as Played

Business vs. Family: What's the answer?

August 13, 2026 • 21 mins
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 fa...
Listen
Watch
Mark as Played

This Content Strategy Doubled His Pipeline

August 12, 2026 • 34 mins
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, gen...
Listen
Watch
Mark as Played

Struggling to Turn Off Your Brain?

August 11, 2026 • 14 mins
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 ...
Listen
Watch
Mark as Played

Deep Work vs. Busywork

August 10, 2026 • 20 mins
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 s...
Listen
Watch
Mark as Played

3 Years. Still Broke. Here's Why.

August 7, 2026 • 17 mins
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'r...
Listen
Watch
Mark as Played

Most Common VA Question

August 6, 2026 • 20 mins
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 o...
Listen
Watch
Mark as Played

Popular Podcasts

    Stuff You Should Know

    Stuff You Should Know

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    Betrayal Weekly

    Betrayal Weekly

    Betrayal Weekly is back for a new season. Every Thursday, Betrayal Weekly shares first-hand accounts of broken trust, shocking deceptions, and the trail of destruction they leave behind. Hosted by Andrea Gunning, this weekly ongoing series digs into real-life stories of betrayal and the aftermath. From stories of double lives to dark discoveries, these are cautionary tales and accounts of resilience against all odds. From the producers of the critically acclaimed Betrayal series, Betrayal Weekly drops new episodes every Thursday. If you would like to share your story, you can reach out to the Betrayal Team by emailing them at betrayalpod@gmail.com and follow us on Instagram at @betrayalpod and @glasspodcasts. Please join our Substack for additional exclusive content, curated book recommendations, and community discussions. Sign up FREE by clicking this link Beyond Betrayal Substack. Join our community dedicated to truth, resilience, and healing. Your voice matters! Be a part of our Betrayal journey on Substack.

    Dateline NBC

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    The Joe Rogan Experience

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

    Love Trapped

    Love Trapped

    Former Bachelor Clayton Echard’s casual one-night fling turned into a paternity nightmare. When the news broke about the scandal, no one believed Clayton at first. He was a reality TV star, and an unpopular one at that. Clayton found himself trying to prove the truth, while trapped in a web of lies, manipulation, and threats. He would soon discover he was not the only one. At its core, this is a story about who you believe and why. It’s an epic battle that would take a group of strangers, citizen sleuths from across the world, to crack the case and finally hold someone accountable. New episodes of Love Trapped are released every Thursday, starting February 26th, 2026. If you would like to reach out to the Love Trapped team, email us at lovetrappedpod@gmail.com and follow along on Instagram @glasspodcasts.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

Explore

iHeart

Live Radio

Podcasts

Artist Radio

Exclusives

News

Features

Events

Contests

Photos

Information

About

Advertise

Blog

Brand Guidelines

Contest Guidelines

Subscription Offers

Jobs

Get the App

Automotive

Home

Wearables

© 2026 iHeartMedia, Inc.

  • Help
  • Privacy Policy
  • Terms of Use
  • AdChoicesAd Choices