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...
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Nov 13, 2026 · 19:16
Freelancing can feel like riding a rollercoaster of unpredictability. One moment you're scrambling for leads, the next you're buried under a mountain of projects. In this…
Nov 12, 2026 · 22:18
Preston and AJ dive deep into strategies that will help you break free from the local client trap and attract high-value, premium international clients. Learn proven tactics for…
Nov 11, 2026 · 18:45
Ihoku Binatonu has years of experience in their field, and clients keep saying the same thing: “You should write a book” or “You should start a podcast.” But Ihoku isn’t sure…
Nov 10, 2026 · 25:04
Fratella has spent eight years building a consulting practice almost entirely on referrals. She knows publishing her ideas would grow her reputation, but client work wins every…
Nov 9, 2026 · 32:26
Kendall Cherry walked out of a Fortune 100 C-suite ghostwriting job with $10,000 in savings and built a multi-six-figure ghostwriting business from scratch. Now, with AI pumping…
Nov 6, 2026 · 20:10
Preston and guest AJ Cassata dive deep into the art of pricing, revealing how freelancers can confidently raise their rates without losing momentum. Learn the counterintuitive…
Nov 5, 2026 · 16:37
In this episode of Freelance to Founder, we dive deep into the art of finding your niche, exploring practical strategies for designers and content creators navigating the complex…
Nov 4, 2026 · 15:36
Are you a freelancer struggling with the nerve-wracking task of increasing your prices? In this eye-opening episode, Preston Lee and guest host Christine Olivas dive deep into…
Nov 3, 2026 · 16:58
It can be a real challenge to create a portfolio that actually converts new clients. This episode of Freelance to Founder dives deep into creative ways to showcase your…
Nov 2, 2026 · 18:02
Tired of networking groups that feel more like spam factories than genuine connection opportunities? In this episode, Clay breaks down the art of finding professional groups that…
Oct 30, 2026 · 12:15
What happens when a client's spouse starts meddling in your carefully crafted design process? In this episode, we dive deep into the tricky dynamics of managing client…
Oct 29, 2026 · 16:26
Drowning in proposal and contract paperwork? Clay and Preston reveal the surprising truth about client management tools—it's not about finding the perfect software, but something…
Oct 28, 2026 · 14:57
Have you ever sent a proposal, completed extra work, and then panicked about sending the invoice? Laura did exactly that—and she's convinced she's about to lose a valuable…
Oct 27, 2026 · 24:34
Is it just me, or does it seem easier to close a sale when you're a freelancer than as a full agency? Amy Bridges asked this question which lead Preston and Clay to tackle the…
Oct 26, 2026 · 15:10
An old client from two years ago wants the original design files from a past project—but you're worried about losing future work by handing them over. Should you push back,…
Oct 23, 2026 · 14:57
Feeling burned out on the business side of freelancing? You still love the creative work, but networking and client acquisition feel overwhelming? You're not alone. In this…
Oct 22, 2026 · 20:40
As your freelance business grows, you hit an inevitable ceiling: there's only so much you can do yourself. But delegating effectively is harder than it sounds. How do you train…
Oct 21, 2026 · 14:02
It's 5:22 PM on a Friday, and a client emails asking if you can design an ad tonight. Do you drop everything and work late? Charge a rush fee? Or simply say no? In this episode,…
Oct 20, 2026 · 17:34
Should you charge by the hour or by the project? If you've ever struggled with this question, you're not alone. But here's the truth: you might be asking the wrong question…
Oct 19, 2026 · 22:39
Feeling pressured to add marketing services to your web design business just because a course told you to? In this episode, Preston and Clay challenge the "supposed to" mentality…
Oct 16, 2026 · 22:33
Feeling paralyzed by the endless stream of marketing tactics you "should" be doing? You're not alone. In this episode, Matt from Barrow Studio asks the question every service…
Oct 15, 2026 · 22:15
Feeling nervous about networking? You're not alone. In this episode, Brittany asks how to break into local networking as a shy person, and Clay shares exactly how he built a…
Oct 14, 2026 · 24:07
As your freelance business grows from solo operator to team leader, the chaos can hit fast. Emma Clark's question about transitioning from inbox management to real systems is one…
Oct 8, 2026 · 22:16
Omar's business is growing, and so is his workload. His longtime clients love working with him, which is the problem. As he builds Vision Craft Studios into an agency, every…
Oct 7, 2026 · 24:22
Layla built Bright Horizon Media from the ground up, and now her social media agency has a team and real momentum. Her next challenge is splitting the revenue: what's fair to her…
Oct 6, 2026 · 21:36
Christine Olivas has a calendar that won't quit and a pile of projects she keeps saying no to. The obvious move is to hire, but she knows the wrong hire at the wrong time just…
Oct 5, 2026 · 15:01
CodeCrafter's skills are solid and his work speaks for itself, but he keeps holding back. Charging more feels presumptuous, and calling himself an expert feels like a lie.…
Oct 2, 2026 · 13:44
Garrett is a 30-year-old nonprofit consultant doing great work for a seasoned consultant. The problem is that almost nobody knows it's his work. The more he delivers, the more…
Oct 1, 2026 · 19:30
A solo designer finally gets the call from a big-name client, and it's the kind of project that could turn a freelance business into a real agency. Excitement turns to panic…
Sep 30, 2026 · 18:40
Dieter is weighing a big question from his home base in Europe: is it worth going after US clients at all, or is he fighting a battle he can't win? Preston and Austin show that…
Sep 29, 2026 · 21:11
A freelancer is buried in admin work, turning down good projects and missing dinners at home. The fix seems obvious: hire a VA. But which tasks should go first, and how do you…
Sep 28, 2026 · 22:29
A freelancer sits down to send a quote. The work is agency-level and the results are real, but the number that goes out is half of what an agency would charge. The reason isn't…
Sep 25, 2026 · 22:29
Lana runs Homewear Designs, and real estate agents in New York and the Hamptons keep sending her home staging jobs. The referrals are steady and the business is healthy, but…
Sep 24, 2026 · 23:00
Andre from New York keeps watching his projects balloon past their original scope, and he's tired of feeling like the bad guy for saying no. Preston and Austin Church break down…
Sep 23, 2026 · 20:51
Maya wants to offer more high-ticket services, but she's stuck on how to package them without just pulling a number out of thin air. Preston and Austin break down the exact…
Sep 22, 2026 · 18:55
Victor is doing great work for his clients in Berlin, but once the deliverables ship, the emails stop coming. He's left wondering if he did something wrong or if this is just how…
Sep 21, 2026 · 20:39
Hannah is ready to make her first hire, but she's stuck on one big decision: stay local or go global. Brian Samson, founder of Plugg Technologies and a three-time agency builder,…
Sep 18, 2026 · 20:16
Dana runs her freelance business hoping to stay organized without sacrificing the freedom she went into business for in the first place. Preston and Austin Church share the exact…
Sep 17, 2026 · 19:53
Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Learn more about your ad…
Sep 16, 2026 · 18:49
Melissa wants to sell more consistently, so she asks Austin Church and Preston to walk through their actual sales process, step by step. They break down the handoff from…
Sep 15, 2026 · 20:14
Mark and a few others in Austin Church's Freelance Cake community keep running into the same wall: a client asks for a website or a logo, but the deeper conversation reveals they…
Sep 14, 2026 · 19:17
Dave's agency works, for now. Pricing, delivery, client issues—it's all running through his head, and he's starting to feel it crack under the weight. Jesse P. Gilmore, founder…
Sep 11, 2026 · 23:32
Priya built her agency to escape the nine-to-five, but somewhere along the way, the business started running her instead. She's taking on every client that comes her way,…
Sep 10, 2026 · 26:58
Marcus built his agency by doing everything himself, and it worked—until it didn't. Now he's got steady clients, recurring revenue, and a small team, but he's still making every…
Sep 9, 2026 · 18:49
Lena is staring down her first tax season as a freelancer and wants to know whether she should hire an accountant right away or figure it out herself. Preston and Austin Church…
Sep 8, 2026 · 19:11
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…
Sep 7, 2026 · 22:53
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…
Sep 4, 2026 · 19:09
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…
Sep 3, 2026 · 20:35
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…
Sep 2, 2026 · 17:26
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…
Aug 28, 2026 · 24:11
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…
Aug 27, 2026 · 16:15
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…
Aug 26, 2026 · 20:12
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…
Aug 25, 2026 · 18:03
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…
Aug 24, 2026 · 20:38
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…
Aug 21, 2026 · 19:14
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…
Aug 20, 2026 · 18:40
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…
Aug 19, 2026 · 25:39
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…
Aug 18, 2026 · 21:42
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…
Aug 17, 2026 · 18:34
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…
Aug 14, 2026 · 19:45
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…
Aug 13, 2026 · 21:55
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…
Aug 12, 2026 · 34:52
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…
Aug 11, 2026 · 14:47
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…
Aug 10, 2026 · 20:01
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…
Aug 7, 2026 · 17:22
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…
Aug 6, 2026 · 20:34
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…
Aug 5, 2026 · 15:30
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…
Aug 4, 2026 · 18:22
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,…
Aug 3, 2026 · 19:27
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…
Jul 31, 2026 · 17:52
Sam is new to freelancing and stuck on a question every beginner faces: how do you charge for value when there's no hourly rate to fall back on? Preston and bestselling author…
Jul 30, 2026 · 18:18
Beatrice has spent six years as a graphic designer working for someone else, and now she's ready to freelance as a digital artist. There's just one problem: she feels weird…
Jul 29, 2026 · 19:46
After years of freelance writing for other people's businesses, David is torn: keep serving clients, or finally build something of his own? Preston sits down with Amy Suto, whose…
Jul 28, 2026 · 18:29
Luis wants to grow, but every new client request—email marketing, influencer campaigns, partnership deals—feels like a decision that could either build his agency or blur what it…
Jul 27, 2026 · 17:35
Natalie has built a growing agency, but her clients still treat her like a freelancer — calling her in, expecting her hands-on every project, and hesitant to work with anyone…
Jul 24, 2026 · 22:31
Marcus is crushing it as a solo paid ads consultant, but every time he tries to bring on help, his margins vanish. Is his offer strong enough to actually support a team, or is he…
Jul 23, 2026 · 19:47
Layla went from working solo to leading a team of 12 — but her website and socials still tell the old story. Preston and PR consultant Haley Raymond dig into how fast-growing…
Jul 22, 2026 · 20:25
Andre knows he needs to position himself as the expert in his field, but he's stuck on how. More social media? More speaking gigs? Preston and Haley Raymond break down the real…
Jul 21, 2026 · 20:50
Haley Raymond spent years in newsrooms before becoming a publicist, so she knows exactly what makes a journalist say yes and what gets deleted on sight. Preston sits down with…
Jul 20, 2026 · 13:41
Fatima has been running solo for years and finally feels ready to lead a team—but she's stuck on how to actually think like a CEO instead of a freelancer doing everything…
Jul 10, 2026 · 18:28
Lucas runs a freelance business he knows has real potential — but every time he tries to think bigger, the daily grind of client work pulls him back in. He wants a genuine…
Jul 9, 2026 · 19:24
Freelance writing can feel like a financial rollercoaster, with many creators struggling to price their services confidently. In this revealing conversation, Preston and Amy Suto…
Jul 8, 2026 · 20:02
Malik is juggling client work, marketing, and admin—and he's running on fumes. Preston and Amy Suto, creator of the bestselling Substack Make Writing Your Job and author of the…
Jul 7, 2026 · 20:35
Amy Suto has built a seven-figure freelance writing career in an era when most writers are watching AI erode their client base. Her secret? Memoir ghostwriting — a niche so…
Jul 6, 2026 · 19:13
Jonas runs a solo service business and feels buried under tasks he can barely keep up with. He knows systems and automation are supposed to be the answer—but with everything on…
Jul 3, 2026 · 20:34
Lucia has hired her first subcontractors—a milestone worth celebrating. But now she's spending more time correcting their work than she is on her own, and she's starting to…
Jul 2, 2026 · 18:54
Nia has been freelancing solo for years and just landed the kind of project that changes everything—her first big team project. She's excited, but the reality is setting in fast:…
Jul 1, 2026 · 16:31
Noah loves his work — but the moment it comes to promoting it, something freezes up. He knows he needs to market himself, yet every attempt feels either pushy or performative.…
Jun 30, 2026 · 29:03
A freelancer scrolling through TikTok sees the same ad for the hundredth time: "Convert to an S-Corp and save $10,000 in taxes—easy!" Preston has seen it too. So has CPA George…
Jun 29, 2026 · 18:27
Alicia Martinez is running a freelance business and tracking every dollar in a spreadsheet. It's working — for now. But she's wondering if it's time to graduate to real…
Jun 26, 2026 · 21:32
Tanya has been freelancing full-time for a year, but her income swings wildly from month to month—and she has no idea how to build a budget around a paycheck that never looks the…
Jun 25, 2026 · 14:13
Sophia has a client who won't stop asking for small favors after the project wrapped. The work is done, the deliverable was handed off—and yet the requests keep trickling in.…
Jun 24, 2026 · 18:31
Marcus Thompson is a copywriter ready to ditch hourly billing—but he's worried that switching to flat-rate pricing means leaving money on the table. Preston and Chanda Costin…
Jun 23, 2026 · 14:55
Priya has a client she genuinely enjoys working with—the work is solid, the money is good, and the relationship is smooth. The problem? They never pay on time. Not occasionally…
Jun 22, 2026 · 20:39
Jasmine Lee is weighing a decision that trips up nearly every freelancer at some point: a potential client wants to pay less than her rate, and there's a gap in her income that…
Jun 19, 2026 · 20:39
Bremley is running a real business — four clients, $8,100 in monthly recurring revenue — and he wants to know how to scale it. He's already proven he can close. Now he needs the…
Jun 18, 2026 · 24:52
Dr. Noah St. John has spent his career helping Hollywood celebrities, professional athletes, and nine-figure CEOs break through the invisible ceiling holding them back. Now he…
Jun 17, 2026 · 20:23
Kwame is wrestling with a question almost every freelancer has whispered to themselves late at night: when does the money actually get steady? Preston and Meredith Cooley—founder…
Jun 16, 2026 · 18:18
Diego Morales is thinking about making the leap into freelancing and wants to know what seasoned freelancers would do differently if they could start over. Preston and Meredith…
Jun 15, 2026 · 18:18
Aisha Raman wants to know the single biggest lesson you learn when you first go out on your own. Preston and Meredith Cooley—copywriter, educator-turned-entrepreneur, and founder…
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