Freelance to Founder

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 actually need a strategy first. Do you upsell them on the spot and risk scaring them off, or just deliver what they asked for and eat the extra work for free? Preston and Austin break down exactly when to introduce a stra...

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 of Niche In Control, joins Preston and Sabrina to map out exactly which systems to build first, from client onboarding to capturing the tribal knowledge that only exists in a founder's brain. Sabrina pushes the conversation...

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, terrified that saying no will kill her momentum. Preston, Sabrina, and Jesse P. Gilmore unpack the five-step framework for reclaiming time, documenting your work, and pricing based on value instead of hours—plus why getting selec...

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 decision, reviewing every deliverable, and jumping in the moment something goes wrong. Is that scrappy founder energy, or is it holding the business back? Preston, Sabrina, and agency coach Jesse P. Gilmore break down the...

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 share the expensive lessons they each learned the hard way — including a mistake that cost Preston tens of thousands of dollars — and lay out exactly when it makes sense to bring in a CPA versus when you can DIY. They dig i...

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 contract isn't really about winning in court — it's about setting expectations before the work even begins. They walk through the deposit rules, red flags, and reference checks that keep freelancers from getting burned, whether...

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 head-on, walking through the pitfalls of using your old salary as a benchmark and the trap of pricing based on what your freelance friends charge. They introduce two numbers every freelancer needs — a survival rate and a dream...

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 a...

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 A...

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 ha...

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,...

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 road...

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...

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 n...

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...

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...

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...

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 w...

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—n...

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 communic...

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, t...

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 mea...

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 l...

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...

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...