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Freelance to Founder

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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.



679 Episodes
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Will AI Replace You?

Will AI Replace You?

2026-11-0932:26

Kendall Cherry walked out of a Fortune 100 C-suite ghostwriting job with $10,000 in savings and built a multi-six-figure ghostwriting business from scratch. Now, with AI pumping out more content than ever, she's seeing something most people wouldn't predict: demand for premium, human-written sales copy is climbing. Preston calls an audible on this episode and puts his own question to Kendall: what does AI really mean for the future of writing careers? They dig into "lowest common denominator messaging," why editing an AI draft can take an expert twice as long as writing from scratch, how Kendall tackles the AI question head-on in her sales process, and why people's craving for real, human connection isn't going anywhere. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Kendall Cherry → https://kendallcherry.com Here to Sell (Kendall's book) → https://www.heretosellbook.com Kendall Cherry on LinkedIn → https://www.linkedin.com/in/kendall-cherry/ Learn more about your ad choices. Visit megaphone.fm/adchoices
Preston and guest AJ Cassata dive deep into the art of pricing, revealing how freelancers can confidently raise their rates without losing momentum. Learn the counterintuitive strategies that can help you attract better clients, work less, and earn more. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with AJ -> https://www.youtube.com/@ajcassataofficial https://www.linkedin.com/in/ajcassata/ Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode of Freelance to Founder, we dive deep into the art of finding your niche, exploring practical strategies for designers and content creators navigating the complex world of freelance work. Preston and Christine break down the myths about specialization and offer invaluable insights for finding your unique professional path. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices
Are you a freelancer struggling with the nerve-wracking task of increasing your prices? In this eye-opening episode, Preston Lee and guest host Christine Olivas dive deep into the art and science of rate increases, offering invaluable insights for freelancers at any stage of their career. Whether you're battling imposter syndrome or wondering if your rates truly reflect your worth, this episode is your roadmap to confident pricing. Links: Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices
Portfolio = Proof

Portfolio = Proof

2026-11-0318:43

It can be a real challenge to create a portfolio that actually converts new clients. This episode of Freelance to Founder dives deep into creative ways to showcase your professional expertise, even when you're new to the freelance world. Preston Lee and Christine Olivas share insider tips on how to build a compelling portfolio that attracts clients and demonstrates your value. Links: Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices
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