Is Freelancing Freedom a Lie?

Melissa is spending hours on custom proposals—and she knows something is off. The pricing second-guessing, the laborious back-and-forth, the sinking feeling that all those unbillable hours may not even convert. Preston and Austin dig into why the traditional proposal process might be the problem itself, and lay out smarter, faster alternatives that can actually win more work with less wasted time. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Mark has built something real—a growing agency with contractors doing solid work and clients getting results. But success has come with an unexpected side effect: guilt. He’s making money from other people’s labor, and it doesn’t sit right with him. Preston and Austin Church unpack where that guilt actually comes from, why it’s often a sign of good character rather than bad business, and how to think clearly about fair pay, profit, and what you truly owe the people on your team. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

A question from Austin Church's Freelance Cake community puts tax strategy center stage: is taking an S-Corp election actually worth it? Preston and Austin break down the real mechanics behind this often-misunderstood move—how splitting your income between a salary and shareholder distributions can save you tens of thousands of dollars a year, why your state tax laws matter more than you might think, and exactly when it stops being worth the extra paperwork. If your freelance or agency revenue is approaching six figures, this is the conversation that could change how you run your business. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Hannah is ready to make her first hire and is seriously considering looking beyond U.S. borders — but she doesn't know what she doesn't know. In this episode, Preston is joined by Brian Samson, a three-time founder who has scaled recruiting agencies to $4 million ARR by building teams across Latin America and beyond. Together they walk Hannah through exactly how to approach international hiring for the first time: where to start, which regions tend to excel at what, how to think about time zones, and the blind spots that trip up most first-time international managers — including the costly "follow-the-sun" communication trap that can burn a full week on a single misunderstood task. 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

Andre is getting pulled in every direction by his clients — new requests keep piling on top of the original project, and he doesn't know how to push back without risking the relationship. Preston and Austin Church, founder of the Freelance Cake Community, dig into exactly how to handle scope creep with confidence: from crafting airtight contracts and expectations docs, to the subtle language shifts that remind clients you're a business partner — not an employee on the payroll. Plus, when to just say yes anyway. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Maya has a clear goal: charge more. She's doing solid work, she's got clients, but she knows she's leaving money on the table—she just doesn't know how to structure a premium offering that actually feels worth the price tag. Preston and Austin dig into the real psychology behind high-ticket packages, from learning to charge for your thinking (not just your deliverables) to using the "magic wand" question to uncover what clients will actually pay a premium for. If you've been wondering how to move upmarket, this episode is the practical push you need. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Victor is a freelancer based in Berlin doing solid project work—delivering results, getting paid, and then watching clients disappear into the void. No follow-up, no next project, just silence. He wants to know how to build real, lasting client relationships instead of one-and-done engagements. Preston and Austin Church, founder of Freelance Cake, break down why clients go quiet (hint: it's almost never about you), how to build an offboarding process that keeps doors open, and how to plant the seeds of a long-term relationship before you even send the final deliverable. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Dana in Seattle went freelance for the freedom—and now she's drowning in deadlines and client expectations she can barely keep straight. Sound familiar? Preston and Austin Church unpack the promise that draws most people into freelancing in the first place, and whether the "no boss, no calendar" dream was ever really the point. Along the way, they share three dead-simple systems for keeping projects organized without the suffocation—including a one-page brief that replaces a hundred scattered emails and a counterintuitive trick involving more deadlines that actually sets you free. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Dave's agency is humming along, but everything — how he prices, how he delivers, how he handles problems — lives entirely in his head. It's worked so far, but he can feel it starting to strain. So he's asking the question every growing agency owner eventually faces: if I had to pick just one or two things to systemize first, what would they be? Preston, Sabrina, and Jesse P. Gilmore from Niche in Control dig into exactly that — walking through a practical, priority-ordered approach to getting out of your own head without turning your business into a corporate machine. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Connect with Jesse: - Website - ⁠https://www.nicheincontrol.com⁠ - LinkedIn - ⁠https://www.linkedin.com/in/jessepgilmore/⁠ - SAA trial - ⁠https://nicheincontrol.com/triangle⁠ - Book - ⁠https://www.nicheincontrol.com/book ⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Priya left her full-time job to build an agency on her own terms — and now finds herself buried under client obligations she can't seem to escape. Every new project feels like a trap, and turning down work feels like a risk she can't afford. Preston and Sabrina sit down with Jesse P. Gilmore of Niche in Control to map out exactly how agency owners can build for freedom instead of accidentally building another job — covering time systems, ideal client selection, offer design, and the mindset work that makes all of it stick. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Connect with Jesse: - Website - ⁠https://www.nicheincontrol.com⁠ - LinkedIn - ⁠https://www.linkedin.com/in/jessepgilmore/⁠ - SAA trial - ⁠https://nicheincontrol.com/triangle⁠ - Book - ⁠https://www.nicheincontrol.com/book ⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices