Freelance to Founder

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" q...

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...

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 projec...

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...

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 buil...

Marcus built his agency the hard way—doing everything himself until the clients came, the revenue got steady, and the team grew. But now, with real momentum on his side, he's still the one making every call, reviewing every deliverable, and firefighting every problem. He suspects this habit that once made him successful might now be the very thing capping his growth. Preston and Sabrina sit down w...

Lena is a new freelancer staring down one of the most universally dreaded moments in self-employment: tax season. She knows taxes are confusing, but she's not sure whether to invest in an accountant from the start or try to handle it herself. Preston and Austin Church—both of whom learned the hard way—share what they wish someone had told them earlier, including the costly mistake that set Preston...

Rashid wants to land clients outside his home country, but the unknowns are holding him back — different governments, tricky payment terms, and contracts that feel impossible to enforce across borders. Preston and Austin Church dig into exactly how to protect yourself when working with international clients, and their answer might surprise you: where a client lives matters far less than most freel...

Aisha is just starting out as a freelancer and wrestling with the question that trips up almost everyone in the early days: what should I actually charge? She knows she doesn't want to undersell herself, but she also has no idea where to set her rates. Preston and Austin Church—veteran freelancer and author of Free Money—unpack three different pricing approaches, make the case for building your ra...

Jenna finds herself wanting to build a successful business without sacrificing her values or family time. Preston Lee and Dawn Andrews share what it takes to design a leadership role that truly fits your life, offering compassionate insights for ambitious professionals navigating the complex terrain of work-life integration. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Su...

For Nicole, what started as a quest for freedom through freelancing has morphed into a complex leadership challenge—managing a team that seems to consume more time than the work itself. Preston Lee and Dawn Andrews explore the art of creating standard operating procedures (SOPs) that transform team management from a headache into a strategic advantage. They reveal the secrets to empowering your te...

Amanda is standing at a pivotal moment in her leadership journey—wrestling with the internal doubts that plague many first-time team leaders. As she steps into her new role, the weight of proving herself feels overwhelming. Preston and Dawn Andrews dive deep into the psychology of leadership, revealing how vulnerability, communication, and embracing risk can transform imposter syndrome from a para...

Jason from our listener community is stuck in a common entrepreneurial trap—feeling overwhelmed by the administrative demands of maintaining his LLC. Preston Lee and Bobby Casey dive deep into why business structure matters, how to manage compliance without losing your mind, and the critical steps every business owner needs to know about protecting their assets. Bobby Casey, founder of Business An...

Parker is stuck navigating the murky waters of freelance finance, desperate to transform his business from a mere survival mode into a strategic growth machine. Preston and George Thomas dive deep into the critical financial strategies that separate struggling freelancers from successful business owners. From understanding revenue forecasting to building a financial support team, this episode crac...

Lana has built a successful freelance career but finds herself paralyzed by the complexities of retirement planning. Preston Lee and financial expert George Thomas unpack the essential strategies for independent professionals to build sustainable wealth. Diving deep into retirement accounts, investment opportunities, and wealth-building tactics, this episode provides a comprehensive roadmap for fr...

Lauren is navigating a pivotal moment in her entrepreneurial journey—her business has taken off since becoming a parent, but she's struggling to find harmony between her family's needs and her business ambitions. Preston and Lindsay dive deep into the messy, beautiful reality of being a parent-entrepreneur, sharing hard-earned wisdom about energy management, setting boundaries, and creating a life...

Nicole is standing at a critical crossroads in her entrepreneurial journey. After leaving corporate America to start her own business, she's wrestling with doubts and financial uncertainty. Preston and Lindsay dive deep into the crucial strategies for new entrepreneurs facing this make-or-break moment: understanding that business success is a marathon, not a sprint, and learning how to navigate th...

Amanda is standing at a critical crossroads in her entrepreneurial journey, wrestling with one of the most challenging questions every bootstrapper faces: How do I strategically spend my limited funds without taking on investors? In this powerful episode, seven-figure entrepreneur Lindsay Pinchuk breaks down the exact playbook for making smart financial decisions that can transform a bootstrapped...

Kevin is standing at a pivotal crossroads in his professional journey—transitioning from managing teams to becoming a solopreneur. Preston Lee and Moe Choice dive deep into the mental and strategic shifts required when moving from leading groups to leading yourself. With insights from Moe's extensive background as a six-time co-founder and leadership coach, this episode unpacks the emotional lands...

Daniel is trapped in a calendar packed with work, questioning the true meaning of a "freedom-based business." Preston and Moe dive deep into the nuanced world of solopreneurship, unpacking what freedom really means—and it's not just about having an empty calendar. From passionate contribution to strategic positioning, this episode reveals how to create a business that doesn't just provide income,...

Alex has built a solid freelance income but feels trapped in a cycle of trading time for money. Seeking to transform his business from a job-like grind to a strategic growth engine, he asks a critical question: How do you know when it's time to completely redesign your business or just keep working harder on what you've already got going? Preston and Moe dive deep into the strategies that help fre...

When bad contractor experiences leave you gun-shy about hiring, how do you rebuild trust and create a successful team? Emily's struggle with past hiring mishaps is a common challenge for freelancers and agency owners. In this episode, Preston and Kevin Rice dive deep into the art of effective hiring, offering practical strategies for finding, integrating, and supporting contractors that truly add...

Mark is stuck in the freelance grind—working nonstop and wondering how to transform his solo operation into a real company. Preston Lee and Kevin Rice dive deep into the critical moment when freelancers must shift from doing everything themselves to building a sustainable business. Drawing from Kevin's experience scaling a two-person startup to a 200-person agency with a nine-figure exit, this epi...

Kevin Rice knows the delicate dance of entrepreneurship and fatherhood all too well. After scaling his digital agency to a nine-figure exit, he discovered the hard truth that success means nothing if it comes at the cost of your family connections. In this powerful episode, Kevin shares his personal journey of learning to be an intentional parent while building a thriving business, offering a road...

Michael is standing at a critical crossroads in his entrepreneurial journey—desperate to break through the seven-figure barrier but unsure how to transform his current six-figure business into something truly scalable. In this episode, Charles Gaudet, CEO of Predictable Profits and renowned business coach, cracks open the playbook for moving beyond referrals and hard work into a strategic, demand-...