Drowning? Here's the Fix.

Christine Olivas scaled from solo freelancer to leading a 24-person operation—but the path wasn't as simple as just "hire when you're busy." Preston and Christine dig into one of the most misunderstood decisions in freelancing: when to bring someone on, who to bring on first, and how to avoid trading one grind for another. If you're turning down work and losing sleep, this episode will help you figure out whether you're ready to grow—or just ready to burn out faster. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

CodeCrafter is talented, working hard, and building something real—but a nagging voice keeps whispering that he's not expert enough to charge more, land better clients, or call himself a professional. Preston digs into one of the most common mental traps freelancers fall into: waiting to feel ready before they act. This episode breaks down how to reframe what expertise actually means, why your clients don't need the world's best—they need someone who can solve their specific problem, and how to start building confidence not by knowing more, but by doing more. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Subcontracting can feel like a smart move—until you realize your business is quietly disappearing into someone else's brand. Sound familiar? In this solo episode, Preston digs into a question from Garrett, a 30-year-old nonprofit consultant who's starting to wonder: am I building my business... or just theirs? He's been subcontracting for a seasoned consultant, and the lines between "partnership" and "being swallowed up" are getting blurry fast. Merge, stay, or go solo? Preston walks through how to test your market without blowing up a valuable relationship, set real boundaries before resentment kicks in, and make the leap from subcontractor to independent consultant—without burning the bridges that got you here. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Dream client. Huge project. Zero team. Do you say yes and figure it out later—or build the team first and hope they stick around? Preston and Austin break down the classic chicken-and-egg trap every growing freelancer hits... and reveal a third option that could save your reputation, your sanity, and your shot at finally making the leap from solo to agency.Support our show sponsors → https://freelancetofounder.com/sponsorsSubmit your own question → https://freelancetofounder.com/askJoin Austin's Premium Community → ⁠⁠https://www.freelancecake.com/community⁠⁠Get Austin's Book, Free Money → ⁠⁠https://austin-l-church.kit.com/cf0feb3e27⁠This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Does your zip code actually matter to American clients? Dieter's freelancing from Europe and wondering if the US market is even worth chasing. The answer might surprise you. Preston and Austin break down why being "foreign" isn't the handicap you think it is — and how to flip your location into a competitive edge that US-based freelancers simply can't match. If geography's been your excuse, this episode pulls the rug right out from under it. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → https://www.freelancecake.com/community Get Austin's Book, Free Money → https://austin-l-church.kit.com/cf0feb3e27 This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Think you're ready to hire a VA... but have no idea where to start? You're not alone. Every growing freelancer hits that wall — a million tasks, not enough hours, and zero clue who to trust with the work. In this episode, Preston sits down with Austin Church (founder of Freelance Cake Community) to break it all down. Austin brings 4+ years of real VA experience and shares the one thing most freelancers get wrong when hiring — plus his dead-simple framework for knowing exactly what to hand off first. Character vs. skills. Freedom vs. burnout. This one might 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 Premium Community → ⁠⁠https://www.freelancecake.com/community⁠⁠ Get Austin's Book, Free Money → ⁠⁠https://austin-l-church.kit.com/cf0feb3e27⁠ This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Still leaving money on the table? Here's the uncomfortable truth: most freelancers underprice themselves—not because they lack skill, but because they're scared of what clients will say. In this episode, Preston and Austin Church dig into the fear of raising rates and what's really holding freelancers back from charging what agencies charge. Austin breaks down the psychology behind client decisions, why replacing you costs them more than you think, and how higher prices can actually make clients trust you more. If you're ready to stop trading time for too little money and start positioning yourself like the authority you already are... this one's for you. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → https://www.freelancecake.com/community Get Austin's Book, Free Money → https://austin-l-church.kit.com/cf0feb3e27 This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Lana runs Homewear Designs and has built a steady stream of home staging clients through real estate agent referrals in New York and the Hamptons. It's working — but she wants to scale up. Is it smarter to double down on those existing relationships, or start exploring new channels to reach a wider audience? Preston and Austin break down how to grow what's already working while branching out strategically through visual content and key partnerships. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → https://www.freelancecake.com/community Get Austin's Book, Free Money → https://austin-l-church.kit.com/cf0feb3e27 This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

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