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Freelance to Founder: Daily Summaries Delivered
by Millo
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. 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.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- Today18 min
This Emotional Block is Killing Your Rates
Beatrice has spent six years as a graphic designer working for someone else, and now she's ready to freelance as a digital artist. There's just one problem: she feels weird charging people for her work, caught between a lack of confidence and the fear that taking money makes her a sellout. Preston and bestselling author Amy Suto dig into the mindset shift that separates hobbyists from professionals, why "solving a problem" beats "selling your art," and how to stand out in a world where AI can generate art in seconds. 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
- Yesterday19 min
The $191K Substack That Changed Everything
After years of freelance writing for other people's businesses, David is torn: keep serving clients, or finally build something of his own? Preston sits down with Amy Suto, whose Substack newsletter now pulls in over $191,000 a year, to unpack how freelancers can turn their writing into equity instead of just income. They dig into paid newsletters, self-publishing, and the exact roadmap for building a writing career that doesn't depend on anyone else's 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
- 2 days ago18 min
Should You Ever Say 'No' to a Client?
Luis wants to grow, but every new client request—email marketing, influencer campaigns, partnership deals—feels like a decision that could either build his agency or blur what it stands for. Preston and Jason Fishman talk through how to know when expanding your services makes sense, when it's a distraction, and why staying open to what the market sends you might matter more than sticking to a five-year plan. It's a practical look at growing on purpose instead of by accident. 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
- 3 days ago17 min
Getting Your Clients to Respect You 100%
Natalie has built a growing agency, but her clients still treat her like a freelancer — calling her in, expecting her hands-on every project, and hesitant to work with anyone else on her team. Preston and Jason Fishman break down how to shift that perception, from positioning your team as thought leaders to building the right "emergency guardrails" that give clients confidence in letting go. This episode is a practical guide to repositioning yourself as a company rather than a one-person show, without losing the trust you worked hard to build. 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
- 6 days ago22 min
Who Should Be Your First Hire?
Marcus is crushing it as a solo paid ads consultant, but every time he tries to bring on help, his margins vanish. Is his offer strong enough to actually support a team, or is he hiring the wrong kind of person for the job? Preston and Jason Fishman, CEO of Digital Niche Agency, break down why your first hire shouldn't just be a copy of you, how to know if your pricing can carry a team, and what it really takes to turn solo income into scalable agency profit. 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
- 1 weeks ago19 min
From Solo to 12 Employees... Now What?
Layla went from working solo to leading a team of 12 — but her website and socials still tell the old story. Preston and PR consultant Haley Raymond dig into how fast-growing service businesses should rebrand without losing the personal connection that got them clients in the first place. They cover the "we" vs "I" shift, when to lean into agency branding, and why keeping a human face out front still matters even as the team grows. 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
- 1 weeks ago20 min
Becoming "The Expert" in Your Niche
Andre knows he needs to position himself as the expert in his field, but he's stuck on how. More social media? More speaking gigs? Preston and Haley Raymond break down the real playbook: why LinkedIn tends to be the first stop for service providers, the difference between telling people you're an expert and showing them, and how to batch your content so consistency doesn't turn into burnout. They also dig into where AI tools genuinely help versus where they just create more noise. 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
- 1 weeks ago20 min
Free Marketing? Here's the Catch
Haley Raymond spent years in newsrooms before becoming a publicist, so she knows exactly what makes a journalist say yes and what gets deleted on sight. Preston sits down with her to unpack earned media: the free but far-from-easy strategy of getting press, podcast features, and local news coverage without spending a cent on ads. They cover when a freelancer or agency owner should start thinking about PR, how to find your "story" even if you think your work is unremarkable, and why a tailored pitch always beats a mass email. If you've ever wondered whether you're ready for the spotlight, this episode lays out the roadmap. 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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About 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. 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.
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