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
This Mistake Cost Me $30,000 [not-audio_url] [/not-audio_url]

Duration: 18:49
Lena is a new freelancer staring down one of the most universally dreaded moments in self-employment: tax season. She knows taxes are confusing, but she's not sure whether to invest in an accountant from the start or try…
This Matters Less Than You Think [not-audio_url] [/not-audio_url]

Duration: 19:11
Rashid wants to land clients outside his home country, but the unknowns are holding him back — different governments, tricky payment terms, and contracts that feel impossible to enforce across borders. Preston and Austin…
Are You Missing Out on Money? [not-audio_url] [/not-audio_url]

Duration: 22:53
Aisha is just starting out as a freelancer and wrestling with the question that trips up almost everyone in the early days: what should I actually charge? She knows she doesn't want to undersell herself, but she also has…
Do I Have to Sacrifice Family for Growth? [not-audio_url] [/not-audio_url]

Duration: 19:09
Jenna finds herself wanting to build a successful business without sacrificing her values or family time. Preston Lee and Dawn Andrews share what it takes to design a leadership role that truly fits your life, offering c…
The Real Power of SOPs [not-audio_url] [/not-audio_url]

Duration: 20:35
For Nicole, what started as a quest for freedom through freelancing has morphed into a complex leadership challenge—managing a team that seems to consume more time than the work itself. Preston Lee and Dawn Andrews explo…
Fighting Imposter Syndrome [not-audio_url] [/not-audio_url]

Duration: 17:26
Amanda is standing at a pivotal moment in her leadership journey—wrestling with the internal doubts that plague many first-time team leaders. As she steps into her new role, the weight of proving herself feels overwhelmi…
When Paperwork = Death [not-audio_url] [/not-audio_url]

Duration: 23:41
Jason from our listener community is stuck in a common entrepreneurial trap—feeling overwhelmed by the administrative demands of maintaining his LLC. Preston Lee and Bobby Casey dive deep into why business structure matt…
With Money, 'Just Surviving" Isn't Enough [not-audio_url] [/not-audio_url]

Duration: 15:45
Parker is stuck navigating the murky waters of freelance finance, desperate to transform his business from a mere survival mode into a strategic growth machine. Preston and George Thomas dive deep into the critical finan…
Will You Actually Have Retirement Money? [not-audio_url] [/not-audio_url]

Duration: 19:42
Lana has built a successful freelance career but finds herself paralyzed by the complexities of retirement planning. Preston Lee and financial expert George Thomas unpack the essential strategies for independent professi…
Family vs. Business [not-audio_url] [/not-audio_url]

Duration: 17:33
Lauren is navigating a pivotal moment in her entrepreneurial journey—her business has taken off since becoming a parent, but she's struggling to find harmony between her family's needs and her business ambitions. Preston…