Freelance to Founder

Millo
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Jan 19, 2026 • 18min

The Real (Unexpected) Reason You Need Contracts

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 freelancers looking to level up their professional relationships. In this episode, you'll discover how to transform contracts from intimidating legal documents into strategic assets that help you communicate clearly, set boundaries, and establish a foundation for long-term client success. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠ Connect with Joey -> https://indielaw.com @TheJoeyVitale on all social media Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 15, 2026 • 18min

"Jack of All Trades" Agency...Good or Bad?

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 niche to intelligently adding complementary services, this episode is a masterclass in scaling your agency with intention and strategic insight. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Jason Linkedin -> ⁠https://www.linkedin.com/in/jafishman/⁠ Jason's Business -> ⁠https://www.digitalnicheagency.com/⁠ Jason's Podcast -> ⁠https://www.youtube.com/@digitalnicheagency Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 14, 2026 • 17min

What does "Charge by Your Value" Actually Mean?

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 business rate, this episode is a masterclass in transforming your creative skills into a profitable business. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ ⁠⁠⁠Buy Amy's new book -> ⁠⁠https://amysuto.com/power⁠⁠ Join Amy's substack -> ⁠⁠https://www.makewritingyourjob.com/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 13, 2026 • 18min

Your Emotions Are Keeping You Poor

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 freelance professional, offering a compassionate and strategic roadmap for valuing your art, understanding your worth, and building the confidence to get paid what you deserve. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask ⁠Buy Amy's new book -> ⁠https://amysuto.com/power⁠ Join Amy's substack -> ⁠https://www.makewritingyourjob.com/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 12, 2026 • 19min

Keep Working for Clients...or Build My Own Thing?

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 freelance writer to a writing entrepreneur who owns their creative destiny. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Buy Amy's new book -> https://amysuto.com/power Join Amy's substack -> https://www.makewritingyourjob.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 9, 2026 • 17min

Do Clients See You as Just 'The Talent'?

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 comprehensive, high-value agency with a talented team behind you. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Jason Linkedin -> ⁠https://www.linkedin.com/in/jafishman/⁠ Jason's Business -> ⁠https://www.digitalnicheagency.com/⁠ Jason's Podcast -> ⁠https://www.youtube.com/@digitalnicheagency Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 8, 2026 • 22min

Hire without Losing Money

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 sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Jason Linkedin -> https://www.linkedin.com/in/jafishman/ Jason's Business -> https://www.digitalnicheagency.com/ Jason's Podcast -> https://www.youtube.com/@digitalnicheagency Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 7, 2026 • 19min

Her Agency is Having an Identity Crisis

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 strategies for positioning yourself as an agency while keeping the human connection that makes your business unique. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠⁠ Connect with Haley: ⁠⁠https://HaleyRaymond.com⁠⁠ ⁠⁠https://www.linkedin.com/in/haleyadams25/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 6, 2026 • 20min

Do Your Clients See You as an Expert?

Haley Raymond, a PR consultant and publicist, shares her expertise on positioning oneself as an industry authority. She discusses the importance of tailored messaging and using LinkedIn effectively to showcase insights and work examples. Haley emphasizes the value of answering public questions to enhance visibility and credibility. To maintain consistency without burnout, she recommends batching and scheduling content. Additionally, she encourages using AI wisely for content brainstorming, while avoiding low-quality output. Discover practical tips to stand out and attract clients.
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Jan 5, 2026 • 20min

Free Advertising for Your Business?

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. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Haley: https://HaleyRaymond.com https://www.linkedin.com/in/haleyadams25/ Learn more about your ad choices. Visit megaphone.fm/adchoices

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