Freelance to Founder

Freelance to Founder

Author: Millo Language: English Episodes: 100
There’s a common gap between working for yourself and truly building something that lasts, and Freelance to Founder lives in that space. This isn’t just theory; it’s a daily conversation for freelancers who are tired of the unpredictable income and ready to create a real business. Host Preston Lee draws from his own journey from freelancer to someone who has built and sold companies, and he brings that grounded perspective to every episode. Nearly every weekday, Preston is joined by other founders and entrepreneurs who’ve navigated the same path, breaking down the practical steps you can take to scale your solo operation. The call-in format means you’re hearing real questions from people in the trenches, facing the same client issues, pricing dilemmas, and growth plateaus you might be. Listening to this podcast feels like having a direct line to a supportive and experienced mastermind group, one that focuses on actionable strategies over vague inspiration. It’s for the designer, writer, developer, or consultant who’s ready to move beyond the feast-or-famine cycle and lay the foundation for something more substantial and sustainable. The discussions are candid, the advice is tested, and the goal is always clear: helping you transition from a solo practitioner to the founder of a thriving business.
Episodes
Don't Charge by Hour or Project. Do this... [not-audio_url] [/not-audio_url]

Duration: 17:04
Lanya has a freelance project in front of her, she’s estimated the hours, and her client is open to either hourly or project-based pricing—so now what? Preston and Clay make the case that the real question isn’t hourly v…
Remove Pain from Recurring Revenue [not-audio_url] [/not-audio_url]

Duration: 22:09
Erica is a web and graphic designer who invested in a coaching program built to turn designers into full-service marketers—complete with monthly retainers, ad campaigns, and recurring revenue. The strategy looked great o…
The Best Marketing Tactic to Get New Clients [not-audio_url] [/not-audio_url]

Duration: 22:03
Matt runs Barrow Studio, a brand identity and strategy agency in Bristol, UK—and he's drowning in advice. Every newsletter, YouTube channel, and podcast promises a different "marketing golden ticket": build an email list…
Overcoming the Fear of Networking [not-audio_url] [/not-audio_url]

Duration: 21:45
Brittany runs her own design studio and knows she needs to get out from behind her screen and start meeting people face-to-face. The problem: she’s shy, and local networking feels downright terrifying. Preston and Clay w…
Things Are Getting Messy [not-audio_url] [/not-audio_url]

Duration: 23:37
Emma Clark runs Clark Content Co. and has spent years managing projects from her inbox and a few spreadsheets—until now. With two contractors on board and plans to hire more, things are getting messy fast. Preston and Ch…
The Power of Trusting Subcontractors [not-audio_url] [/not-audio_url]

Duration: 21:46
Omar has built something worth protecting—a roster of loyal clients who hired him as a freelancer and trust him personally. Now he’s growing Vision Craft Studios into a full agency, and the hardest part isn’t finding new…
Is This Cheating? [not-audio_url] [/not-audio_url]

Duration: 23:52
Layla from Bright Horizon Media has built something real — a small social media marketing agency with two part-time team members and real momentum. Now she's facing the question every growing agency owner hits: how much…
Drowning? Here's the Fix. [not-audio_url] [/not-audio_url]

Duration: 21:06
Christine Olivas scaled from solo freelancer to leading a 24-person operation—but the path wasn't as simple as just "hire when you're busy." Preston and Christine dig into one of the most misunderstood decisions in freel…
Do Clients Care About 'Expertise'? [not-audio_url] [/not-audio_url]

Duration: 14:31
CodeCrafter is talented, working hard, and building something real—but a nagging voice keeps whispering that he's not expert enough to charge more, land better clients, or call himself a professional. Preston digs into o…
Subcontracting = Invisible? [not-audio_url] [/not-audio_url]

Duration: 13:14
Subcontracting can feel like a smart move—until you realize your business is quietly disappearing into someone else's brand. Sound familiar? In this solo episode, Preston digs into a question from Garrett, a 30-year-old…