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, this episode is a real look at the risk, discipline, and timing behind turning freelance income into an actual company. 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

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 means to balance ambition and fatherhood, why "they won't remember anyway" is a dangerous excuse, and how intention — not hours — is what actually makes kids feel like they matter. 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

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 leave zero room for the average, generic freelancer. 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

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 writers of Independence Day and a $5 million villa, to explain exactly how top performers train their brains to switch into—and out of—deep focus. 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

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 actually lead. 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

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 starting to wonder if he's destined to stay a burned-out freelancer forever. Preston and Steven Puri, a former film studio executive who's raised over $21 million in venture capital, break down why most online advice is worthless, how to tell if you're solving a painful enough problem, and where to actually find mentors who've done the thing instead of just talked about it. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 break down when a jack-of-all-trades VA is the smarter first move, when client-facing or technical work demands a specialist from day one, and how to structure that first hire—hours, pay, and processes included—so it actually sticks. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Vitale break down exactly where to start delegating without the risk, from running accountability calls to tracking key business metrics. They dig into how to build trust with a new teammate gradually, why emotional safety matters just as much as task lists, and how to know when you're ready to hand off bigger, client-facing work. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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, or is the real question strategic instead? Preston and business lawyer Joey Vitale break down the difference between hiring employees and contractors, why "bottom-up" hiring often beats bringing on expensive experts too soon, and how to build a team that can run without you—even while you're on vacation. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 exactly when a real contract becomes non-negotiable. Business lawyer Joey Vitale joins Preston to break down why a contract isn't just legal armor, it's a communication tool that sets expectations, prevents scope creep, and keeps every client relationship on solid ground. They dig into the most common contract mistakes freelancers make, from generic templates to a simple LLC naming error that could put your personal assets on the line. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠ Join our FREE online event -> ⁠https://10Xfreelance.com/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices