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...
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Perfecting Your Weekly Schedule
<p>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 upcoming Write for Money and Power, dig into why most freelancers burn out not from working too hard, but from undercharging, context-switching, and never actually deciding who they want to be. This episode is a practical and surprisingly personal look at how to restructure your week—and your identity—so you can grow without collapsing.</p> <p>Support our show sponsors -> https://freelancetofounder.com/sponsors</p> <p>Submit your own question...
Can You AI-Proof Your Business?
<p>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 deeply human, so dependent on trust and storytelling craft, that no language model can touch it. In this episode, Preston sits down with Amy to explore what separates the freelancers who are thriving right now from those who are struggling, why the shift from "typist" to "storyteller" is the most important repositioning a writer can make, and how to think about AI as a powerful assistant rather than a career-ending th...
Of Everything to Automate, This Matters Most
<p>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 his plate, he has no idea where to even begin. Preston and Amy Suto, a seven-figure freelance writer and creator of the bestselling Substack Make Writing Your Job, walk Jonas through a practical framework for identifying what to automate first, why a time audit changes everything, and how managing your energy—not just your calendar—is the real secret to sustainable solo business growth.</p> <p><br></p> <p>...
You Hired. But Now You Just Fix Their Errors All Day.
<p>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 wonder if the whole thing is worth it. Preston and Vijay Rajendran, startup coach and author of The Funding Framework, unpack the real reason delegation breaks down and lay out a practical spectrum—from direction to deferring—that helps leaders calibrate how much oversight each person actually needs. If you've ever found yourself quietly redoing someone else's work, this one's for you.</p> <p><br></p> <p>Support our show sponso...
This Kind of Project Changes Everything
<p>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: she can't do this one alone. Preston and Vijay Rajendran, founder coach at Startup System and partner at GAI Ventures, walk through what it really takes to go from lone freelancer to effective team leader. From identifying your zone of genius to knowing exactly what to look for in your first collaborators, this episode is a practical guide for anyone approaching that pivotal moment when the work gets bi...
Are You "So Over" Sales as a Freelancer?
<p>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. Preston and George Azar, CPA and founder of Bright Budget, dig into why that discomfort is actually a signal worth paying attention to — and what to do about it. From understanding your real value, to finding the clients who genuinely need what you offer, this episode reframes the whole act of selling as something that can feel completely natural.</p> <p><br></p> <p>Support our show sponsors -> https...
Accountant For Freelancers Issues this Warning...
<p>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 Azar, who has spent years cleaning up the mess left behind when people make the switch without understanding what it actually involves. In this episode, they break down what the S-Corp election really means, why the self-employment tax is the number that should actually scare you, and what the TikTok ads conveniently leave out—including the salary requirements, the payroll costs, and the moment the math stops working in y...
It's Time for You to Ditch This
<p>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 bookkeeping software, or skip straight to hiring a professional. Preston and George Azar, CPA and founder of Bright Budget, break down the honest answer: it depends on where your business is headed, how comfortable you are with your numbers, and whether your time is better spent elsewhere.</p> <p><br></p> <p>Support our show sponsors -> https://freelancetofounder.com/sponsors</p> <p>Submit your own question -> https://freelancetofounder.com/ask</p> <p><b...
When Your Income is a Roller Coaster, Try This.
<p>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 same twice. Preston and George Azar, CPA and founder of Bright Budget, walk through the practical money systems that actually work for self-employed people: from percentage-based saving and high-yield accounts to the structural business move that can finally give you a steady, predictable paycheck from your own company.</p> <p><br></p> <p>Support our show sponsors -> https://freelancetofounder.com/sponsors</p> <p>Submit your own q...
The Secret to Handling Needy Clients
<p>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. Preston and Chanda Coston break down how to set clear boundaries, build them into your contracts from the start, and even turn the situation into a recurring revenue opportunity. If you've ever felt awkward saying "that's going to cost extra," this one's for you.</p> <p><br></p> <p>Support our show sponsors -> https://freelancetofounder.com/sponsors</p> <p>Submit your own question -> https://freelancetofounder.com/ask</p> <p><b...
