

Freelance to Founder
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.
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.
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
Mentioned books

Oct 31, 2025 • 20min
Can You Raise Rates w/out 'Scaring' Away Clients?
In this insightful discussion, AJ Cassata, Founder of Revenue Boost, shares his expertise on pricing strategies for freelancers and agencies. He emphasizes the importance of gradually raising rates and testing market tolerance to find the sweet spot without alienating clients. AJ explains how higher prices can attract better clients and reduce workload, and stresses that pricing should reflect the value delivered rather than costs. The conversation also highlights the need for confidence and clarity in communicating value to justify rate increases.

Oct 30, 2025 • 16min
Is "Find a Niche" Outdated Advice?
Join Christine Olivas, Founder and CEO of No Single Individual, as she shares her expertise on niching in the creative industry. Christine breaks down the myth that specialization is always essential. Instead, she advocates for a thoughtful approach, encouraging freelancers to experiment before committing to a niche. Discover how to validate market demand through client conversations and the benefits of building a small team to balance various services. Ultimately, it’s about pursuing what you love while ensuring it aligns with market needs.

Oct 28, 2025 • 15min
Charge More (Yes, Really)
Christine Olivas, Founder and CEO of No Single Individual, shares her expertise on pricing strategies for freelancers. She explores the psychological hurdles like imposter syndrome that hold many back from raising their rates. With insights on the impact of inflation, Christine emphasizes the importance of confidence in value assessment. They discuss effective tactics for communicating increases to clients, advocating for tiered pricing to alleviate price sensitivity. Throughout, the focus remains on nurturing client relationships, which can soften the blow of rate hikes.

Oct 27, 2025 • 16min
Is Your Portfolio Broken?
In this engaging discussion, Christine Olivas, Founder and CEO of No Single Individual, shares invaluable insights on crafting an effective portfolio that converts clients. She reveals creative strategies for showcasing limited work, such as using employer logos for credibility and anonymized case studies to illustrate your process. Christine emphasizes collecting predictive testimonials and suggests alternative proof like recorded consultations. Tune in for tips that make building your portfolio both strategic and compelling!

Oct 23, 2025 • 18min
Find Networking Groups That Don't Suck
In this engaging conversation, Clay Mosley, founder of GoLinus.com and agency-builder, offers savvy insights on effective networking. He explains why many local groups can feel spammy and shares tips on vetting them online. Discover the importance of visiting multiple groups to gauge member reliability and the value of personal invitations. Clay emphasizes that higher-cost groups often attract more serious members, making them worth considering. Plus, he encourages building trust through one-on-one meetings for better referrals. Networking doesn’t have to be painful!

Oct 22, 2025 • 12min
Spouse Making Trouble
What happens when a client's spouse starts meddling in your carefully crafted design process? In this episode, we dive deep into the tricky dynamics of managing client relationships when unexpected stakeholders enter the scene. Whether you're a freelance designer, consultant, or creative professional, you'll want to hear our strategies for navigating these delicate professional waters.
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

Oct 21, 2025 • 16min
Best Proposal & Contract Tool?
Struggling with proposal and contract chaos? Discover the overlooked truth that it's less about finding the perfect software and more about simplifying your process. Learn how to automate proposals and contracts, prioritize getting paid upfront, and use templates for efficiency. Clay and Preston reveal that sometimes a simple handshake or email can suffice for trusted clients. Transform your workflow by designing your process before picking tools—no shiny objects allowed! Streamlining success is all about functionality and automation.

Oct 20, 2025 • 14min
Did I Just Lose Money?
Have you ever sent a proposal, completed extra work, and then panicked about sending the invoice?
Laura did exactly that—and she's convinced she's about to lose a valuable client. But here's the thing: the disaster she's imagining might only exist in her head.
In this episode, Clay and Preston tackle the all-too-common problem of freelancers building up worst-case scenarios before anything bad actually happens. They break down why you should send that invoice, how to handle pushback if it comes, and why the story you're telling yourself is probably far worse than reality. If you've ever hesitated to bill a client for work you've done, this episode will give you the confidence to stop panicking and start acting.
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

Oct 17, 2025 • 24min
Is It Just Me? Or...
Is it just me, or does it seem easier to close a sale when you're a freelancer than as a full agency? Amy Bridges asked this question which lead Preston and Clay to tackle the counterintuitive truth about sales, retention, and positioning—revealing why individuals often win deals faster, but teams keep clients longer. Whether you're debating growing your team or staying solo, this discussion will help you understand which approach actually attracts the clients you want (and why the answer isn't what you might expect).
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

Oct 16, 2025 • 15min
Should I Fight This?
An old client from two years ago wants the original design files from a past project—but you're worried about losing future work by handing them over. Should you push back, charge for the files, or just let it go? In this episode, Preston and Clay tackle Kevin's dilemma about whether to fight for those source files or take the high road. Their advice might surprise you: sometimes the smartest business move is the one that feels like you're giving something away for free.
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


