Freelance to Founder

Freelance to Founder

Freelance to Founder is a call-in show helping real-life freelancers grow their businesses and escape the feast-famine lifestyle. The podcast is hosted by Preston Lee, a former freelancer who has started, built, and even sold successful businesses of his own. Preston is joined nearly every weekday by other expert founders, freelancers, and entrepreneurs to help you take your solo business to the next level. You can submit your questions at FreelanceToFounder.com/ask If you enjoy content from shows like The Futur, Being Freelance, The Accidental Creative, Smart Passive Income, or The Side Hustle Show, then you'll love Freelance to Founder. Join us every weekday to take the next step on your journey from ... freelance to founder.

Episodes

When Your Business is "Meh"

January 23, 2026 • 16 mins
Ethan has been hustling for three years, but feels stuck in a business that's just "meh". Preston Lee and Steven Puri dive deep into the critical strategies for transforming a stagnant freelance business into a thriving agency. From identifying true market pain points to finding authentic mentors who have actually achieved what you're aiming to do, this episode provides a raw, no-nonsense roadmap for breaking through entrepreneuria...
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Most People Get This Wrong When It Comes to Hiring

January 22, 2026 • 20 mins
Omar is standing at a critical crossroads in his business, wrestling with a fundamental hiring decision that could shape his team's future. Should he bring on a jack-of-all-trades virtual assistant who can handle multiple tasks, or invest in a specialized VA with laser-focused expertise? Preston Lee and Joey Vitale dive deep into the strategic nuances of VA hiring, revealing a framework that helps entrepreneurs make smarter team-bu...
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Why You're Scared to Hire a VA (& How to Overcome It)

January 21, 2026 • 15 mins
Melissa is standing at a critical crossroads in her freelance business—overwhelmed by workload but paralyzed by the fear of delegation. Preston and Joey Vitale dive deep into the art of hiring your first virtual assistant (VA) without risking your business's reputation or quality of work. From accountability strategies to building emotional safety for new team members, this episode provides a roadmap for freelancers ready to scale ...
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How to Hire w/out Losing Control

January 20, 2026 • 17 mins
Keisha's agency is at a critical turning point. As her business grows, she's wrestling with the ultimate entrepreneurial challenge: how to build a team without losing control or compromising quality. Preston Lee and Joey Vitale dive deep into the strategic art of hiring, revealing a nuanced approach to scaling your business from a one-person show to a thriving agency. From the risks of top-down hiring to the power of building a tea...
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The Real (Unexpected) Reason You Need Contracts

January 19, 2026 • 17 mins
Hannah is wrestling with a critical question every growing freelancer faces—when and how to implement professional contracts that protect both parties and set the stage for successful client relationships. Preston Lee and business lawyer Joey Vitale crack open the playbook for creating contracts that do more than just protect your business—they build trust, clarify expectations, and serve as a powerful communication tool for freela...
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"Jack of All Trades" Agency...Good or Bad?

January 15, 2026 • 17 mins
Luis is standing at a critical crossroads in his agency's journey. Clients keep requesting additional marketing channels—email, influencers, partnerships—but he's worried about becoming a "do everything" agency that loses its core focus. Preston and Jason Fishman dive deep into the strategic art of service expansion, revealing how to grow your offerings without sacrificing quality or diluting your expertise. From finding your nich...
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What does "Charge by Your Value" Actually Mean?

January 14, 2026 • 17 mins
Samantha is wrestling with one of the most critical challenges for new freelancers: how do you actually price your services based on value? Preston Lee and Amy Suto dive deep into the nuanced art of pricing your freelance work, breaking down the myths of the starving artist and revealing strategic approaches to valuing your unique expertise. From understanding the emotional weight of your deliverables to calculating a sustainable b...
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Your Emotions Are Keeping You Poor

January 13, 2026 • 17 mins
Beatriz has been a graphic designer for six years, working for others, but now stands at a critical crossroads. She wants to start freelancing as a digital artist but finds herself wrestling with an internal conflict: how can she confidently charge for her creative work without feeling like she's "selling out"? Preston Lee and Amy Suto dive deep into the psychological hurdles creatives face when transitioning from employee to freel...
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Keep Working for Clients...or Build My Own Thing?

January 12, 2026 • 19 mins
David is at a pivotal moment in his writing career, caught between continuing lucrative client work and pursuing his dream of building a personal writing platform. Preston and Amy Sudo dive deep into the strategic approach of simultaneously serving clients while investing in your own intellectual property. From leveraging Substack to creating multiple income streams, this episode reveals the blueprint for transforming from a freela...
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Do Clients See You as Just 'The Talent'?

January 9, 2026 • 17 mins
Natalie Chen is standing at a pivotal moment in her entrepreneurial journey, wrestling with a challenge many freelancers face: breaking free from being seen as just "the talent" and establishing herself as a true agency owner. Preston Lee and Jason Fishman dive deep into the strategic art of repositioning your business, revealing how to transform client perceptions from viewing you as a solo contractor to seeing you as a comprehens...
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Hire without Losing Money

January 8, 2026 • 22 mins
Marcus is stuck at a critical turning point in his freelance paid ads consulting business. Every time he tries to hire, his carefully built margins evaporate. Preston Lee and Jason Fishman dive deep into the strategic approach of scaling your agency, revealing the essential insights for hiring the right talent, structuring your offer, and ensuring each new team member contributes directly to your bottom line. Support our show spon...
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Her Agency is Having an Identity Crisis

January 7, 2026 • 19 mins
Layla has achieved an incredible milestone, growing her business from a solo venture to a thriving team of 12 in just two years. But as her company expands, she faces a critical challenge: how to update her messaging, website, and social media to reflect her agency's growth while maintaining the personal touch that helped her succeed. Preston and Haley Raymond dive deep into the art of scaling your brand's story, revealing strategi...
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Do Your Clients See You as an Expert?

January 6, 2026 • 19 mins
Andre is stuck at a critical moment in his freelance career—desperate to stand out but unsure how to transform his skills into undeniable expertise. Preston and Haley Raymond crack open the playbook for positioning yourself as the go-to professional in your field, revealing the strategic secrets of content creation, platform selection, and building a reputation that magnetizes clients. From leveraging LinkedIn to understanding the ...
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Free Advertising for Your Business?

January 5, 2026 • 20 mins
Navigating the world of publicity can feel like a mysterious art, but it's actually an accessible strategy for freelancers and agency owners looking to amplify their message without paying out huge advertising bills. In this episode, PR consultant Haley Raymond breaks down the essentials of earned media, revealing how even small businesses can start building credibility and reaching new audiences through strategic publicity. Suppo...
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The Power of a Mindset Shift

December 29, 2025 • 13 mins
Transitioning from a solo freelancer to a business leader isn't just about hiring employees—it's about fundamentally changing how you approach work, leadership, and success. In this episode, Preston and Vijay dive deep into the critical mindset shifts required to move from being the person who does everything to the leader who enables others to do their best work. Support our show sponsors -> https://freelancetofounder.com/sponsor...
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Are You Thinking Big Enough?

December 23, 2025 • 17 mins
Breaking free from the day-to-day grind isn't just a dream—it's a strategic necessity for freelancers and small business owners looking to transform their work. In this episode, Preston and Vijay Rajendran dive deep into how to create a meaningful vision and actionable roadmap for your business, offering insights that go far beyond traditional growth strategies. Support our show sponsors -> https://freelancetofounder.com/sponsors ...
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From $90/hr to $750/hr

December 22, 2025 • 18 mins
Freelance writing can feel like a financial rollercoaster, with many creators struggling to price their services confidently. In this revealing conversation, Preston and Amy Suto crack open the complex world of freelance pricing, sharing hard-earned strategies that transform how independent professionals value their work. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://...
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How to Work Less (Yes, That's OK)

December 19, 2025 • 19 mins
Freelancing offers incredible freedom, but it can also lead to overwhelming stress and exhaustion. Many freelancers find themselves trapped in a cycle of constant work, juggling client demands, marketing efforts, and administrative tasks. But it doesn't have to be this way. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Amy -> ...
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Will Freelancers Survive AI?

December 18, 2025 • 20 mins
The world is transforming FAST, but creative professionals aren't going extinct—they're evolving. In this eye-opening episode, Preston and Amy Suto dive deep into how freelancers can not just survive, but truly thrive in the age of AI, revealing surprising opportunities for those willing to adapt and specialize. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetof...
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Feeling Overwhelmed?

December 17, 2025 • 18 mins
Feeling overwhelmed by the endless tasks of running a solo business? You're not alone. In this episode of Freelance to Founder, Preston and guest Amy Suto dive deep into practical strategies for automating your workflow, saving time, and protecting your mental energy. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Amy -> Book: ⁠ht...
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