Freelance to Founder

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 hi...

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 pow...

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...

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 delivera...

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 t...

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 bluep...

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 contr...

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...

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 you...

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 levera...

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...

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 -> http...

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:...

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 Submi...

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://freelancetofounde...

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 q...

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...

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 strate...

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 Rajend...

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...

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 Submi...

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...

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://freelancetof...

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://free...

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...