Freelance to Founder

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 with Jesse P. Gilmore from Niche in Control to help Marcus understand the difference between scrappy resourcefulness and a founder bottleneck—and what to actually do about it. 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

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 back $20,000 to $30,000, and the simple mindset shift that makes all the difference. 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

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 freelancers think. The real work is learning to read the room early, set airtight expectations before a project begins, and build habits that filter out bad-actor clients no matter what country they're in. 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

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 rate around what your life actually costs, and explain why anchoring high (and negotiating scope, not price) is the move that separates confident freelancers from the ones who always feel underpaid. 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

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 Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Dawn on Linkedin -> ⁠https://www.linkedin.com/in/freerangethinking/⁠ Listen to Dawn's Podcast -> ⁠https://open.spotify.com/show/5tFfxkHltyeAeetz9ao4pu Learn more about your ad choices. Visit megaphone.fm/adchoices

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 team, reducing management overhead, and reclaiming the entrepreneurial freedom you originally sought. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Dawn on Linkedin -> ⁠https://www.linkedin.com/in/freerangethinking/⁠ Listen to Dawn's Podcast -> ⁠https://open.spotify.com/show/5tFfxkHltyeAeetz9ao4pu Learn more about your ad choices. Visit megaphone.fm/adchoices

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 paralyzing force into a catalyst for growth and confidence. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Dawn on Linkedin -> https://www.linkedin.com/in/freerangethinking/ Listen to Dawn's Podcast -> https://open.spotify.com/show/5tFfxkHltyeAeetz9ao4pu Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Anywhere and an international tax lawyer, breaks down the essential reasons why entrepreneurs should never shy away from proper business structuring. From liability protection to strategic asset management, this episode is your roadmap to understanding the sometimes mundane but critically important world of business administration. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask George's Freedom Builders Academy -> ⁠www.freedombuildersacademy.com Learn more about your ad choices. Visit megaphone.fm/adchoices

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 cracks open the playbook for freelancers ready to take control of their financial future and scale their businesses with confidence. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask George's Freedom Builders Academy -> ⁠www.freedombuildersacademy.com Learn more about your ad choices. Visit megaphone.fm/adchoices

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 freelancers looking to secure their financial future without the safety net of traditional employment. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask George's Freedom Builders Academy -> www.freedombuildersacademy.com Learn more about your ad choices. Visit megaphone.fm/adchoices