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

Why We Struggle to Delegate

November 28, 2025 • 20 mins
Delegation is the critical skill that separates struggling freelancers from successful business founders. In this episode, Preston Lee and Vijay Rajendran break down the complex art of managing subcontractors, offering a roadmap for entrepreneurs who find themselves constantly fixing mistakes and feeling overwhelmed. Learn how to transform your leadership approach from constant oversight to strategic team development. This episode...
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How to Navigate Your First Big Project

November 27, 2025 • 18 mins
Growing your freelance business often means taking on larger projects that require collaboration. But how do you successfully manage a team when you've been a solo operator? In this episode, Preston Lee and special guest Vijay Rajendran dive deep into the art of building and leading your first team project, offering invaluable insights for freelancers ready to level up their business. Vijay Rajendran brings a wealth of experience ...
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Why You're Still Afraid to "Sell" Yourself

November 26, 2025 • 16 mins
Feeling uncomfortable promoting your business? You're not alone. Many freelancers struggle with the fine line between effective self-promotion and feeling like a pushy salesperson. In this episode, Preston Lee and George Azar dive deep into strategies for marketing your services genuinely and confidently. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.c...
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The Real Truth About S-Corps (Don't Get Tricked)

November 25, 2025 • 28 mins
Navigating the world of business taxes can feel like walking through a minefield of conflicting advice and flashy marketing promises. In this eye-opening episode, Preston and George Azar pull back the curtain on S-Corp elections, revealing the nuanced truth behind those tantalizing internet ads claiming massive tax savings. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://f...
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Should You Hire a Bookkeeper? (This Might Surprise You)

November 24, 2025 • 18 mins
Managing finances can make or break a freelance business. In this episode, CPA George Azar breaks down the critical decisions around tracking your money – from simple spreadsheets to professional bookkeeping services. If you're wondering whether it's time to upgrade your financial tracking, this episode offers practical insights that could save you time, stress, and potentially money. Support our show sponsors -> https://freelance...
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How to Budget When Your Income Fluctuates

November 21, 2025 • 21 mins
Freelancing offers incredible freedom, but it also comes with financial uncertainty. If you've ever stressed about managing your money when paychecks vary from month to month, you're not alone. In this episode, Preston and George dive deep into practical strategies for creating a solid financial foundation, even with an unpredictable income stream. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your o...
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Client Asks for Favors—What Should I Do?

November 20, 2025 • 13 mins
Freelancing can be challenging, especially when clients expect ongoing work without additional compensation. In this episode, Preston and Chanda Coston dive deep into a common freelancer dilemma: how to handle clients who continuously ask for small free favors after a project is completed. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect ...
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Switch From Hourly to Flat Rate (w/out Losing Money)

November 19, 2025 • 18 mins
Switching from hourly to flat rate pricing can feel like navigating a minefield for freelancers. In this episode, Preston and Chanda break down the strategies that will help you confidently transition your pricing model, protect your revenue, and position your services as a premium offering that clients will love. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelanceto...
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Is It Best to Drop Late-Paying Clients?

November 18, 2025 • 14 mins
Freelancing offers freedom, but it can also bring financial uncertainty—especially when clients drag their feet on payments. In this episode, Preston and Chanda dive deep into a common freelancer nightmare: managing clients who consistently pay late while trying to maintain a healthy, stress-free business. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder....
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Should You Fill Income Gaps w/ Low-Paying Clients?

November 17, 2025 • 20 mins
Every freelancer faces moments of financial uncertainty. When bills are mounting and opportunities seem scarce, the temptation to accept low-paying work can feel overwhelming. But is compromising your rates really the smart move for your business? In this eye-opening episode, Preston and guest Chanda Coston dive deep into the critical question: Is it ever smart to take on low-paying clients just to fill an income gap? Their insigh...
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5 Places to Get More Leads and Attention

November 14, 2025 • 20 mins
Struggling to grow your freelance business and attract quality clients? In this episode of Freelance to Founder, Dr. Noah St. John breaks down his proven MAPSSS method for generating leads that can transform your business from a side hustle to a thriving agency. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠⁠ Connect with Noah -> ⁠https:...
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These Habits May Be Holding You Back

November 13, 2025 • 24 mins
Breaking free from self-imposed limitations isn't just about willpower—it's about understanding the deep-rooted habits that keep you stuck. In this eye-opening episode, Dr. Noah St. John reveals the psychological mechanisms behind procrastination, fear, and success, offering freelancers a transformative roadmap to move from survival mode to founder status. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Sub...
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How Long Does It Take to Succeed?

November 12, 2025 • 19 mins
Freelancing promises freedom, but the path to steady income can feel uncertain. In this episode, Preston and Meredith dive deep into the strategies that help freelancers build a reliable revenue stream, sharing practical insights from their own experiences of transitioning from uncertain earnings to a stable business model. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https:...
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What We Wish We Knew Before Jumping In

November 11, 2025 • 17 mins
Embarking on a freelance journey can feel like navigating uncharted waters. Many aspiring freelancers get stuck in the preparation phase, overthinking branding, websites, and perfect portfolios instead of taking the most crucial first step: getting clients. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Meredith: Website: ⁠⁠www.pa...
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Our Biggest Lessons Learned as Freelancers

November 10, 2025 • 17 mins
Freelancing isn't just about the work you do—it's about understanding yourself, managing your time, and staying flexible. In this episode, Preston Lee and Meredith Cooley dive deep into the most valuable lessons they've learned while building their freelance businesses, offering insights that go far beyond simple tactics and touch on the personal growth required to truly succeed as an entrepreneur. Support our show sponsors -> htt...
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Balancing Self-Employment Dream with Full-Time Job

November 7, 2025 • 21 mins
Dreaming of launching a freelance business while working full-time can feel overwhelming. What if you could strategically carve out time, optimize your schedule, and build momentum without burning out? In this episode, former teacher turned copywriter Meredith Cooley shares her proven strategies for transforming side hustle aspirations into reality. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your ...
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How We Got Our Very First Clients

November 5, 2025 • 11 mins
Breaking into freelancing can feel like an impossible challenge when you're just starting out. But what if landing your first client is simpler than you think? In this episode, Preston and AJ Cassata dive deep into practical strategies for new freelancers looking to secure their inaugural client, sharing personal stories and actionable advice that can transform your freelance journey. Support our show sponsors -> https://freelance...
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Buying Back Your Time as a Freelancer

November 4, 2025 • 16 mins
Freelancing offers freedom, but it can also lead to working more hours than ever before. In this episode of Freelance to Founder, Preston and AJ dive deep into a listener's struggle with time management, offering practical strategies for freelancers feeling overwhelmed and overworked. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with ...
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Why You're (Still) in the Feast-Famine Stage

November 3, 2025 • 18 mins
Freelancing can feel like riding a rollercoaster of unpredictability. One moment you're scrambling for leads, the next you're buried under a mountain of projects. In this episode, Preston and AJ dive deep into practical strategies for stabilizing your freelance business, transforming sporadic opportunities into a consistent, sustainable income stream. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit you...
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Stuck with Low-Paying Clients? Here's the Fix...

November 1, 2025 • 21 mins
Preston and AJ dive deep into strategies that will help you break free from the local client trap and attract high-value, premium international clients. Learn proven tactics for transforming your outreach, positioning your agency, and landing the clients you deserve. Links: Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with AJ -> htt...
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