Business vs. Family: What's the answer?

Business vs. Family: What's the answer?

Author: Millo August 13, 2026 Duration: 21:55
Jason is building a business he's proud of, working harder than he ever has — but his kids only ever see him working, and he's afraid he's running out of time to change it. Kevin Rice knows that fear firsthand. He scaled his agency from a garage to a nine-figure exit, then discovered his kids had never actually seen him work hard, only felt him absent. Preston and Kevin dig into what it really means to balance ambition and fatherhood, why "they won't remember anyway" is a dangerous excuse, and how intention — not hours — is what actually makes kids feel like they matter. 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

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.
Author: Language: English Episodes: 50

Freelance to Founder
Podcast Episodes
Most Common VA Question [not-audio_url] [/not-audio_url]

Duration: 20:34
Omar is ready to bring on his first virtual assistant, but he's stuck on one question: hire a generalist or go straight to a specialist? Preston and business lawyer Joey Vitale break down when a jack-of-all-trades VA is…
Evil VA? [not-audio_url] [/not-audio_url]

Duration: 15:30
Melissa is drowning in her own to-do list but terrified to bring on help—what if a new hire messes up a client deliverable or damages her brand? Preston and business lawyer Joey Vitale break down exactly where to start d…
The #1 Burnout Cure [not-audio_url] [/not-audio_url]

Duration: 18:22
Keisha's agency is growing, but everything still runs through her—and she's starting to wonder if that's sustainable. Should she form a bigger legal structure before she hires, or is the real question strategic instead?…
Big Contract Oops [not-audio_url] [/not-audio_url]

Duration: 19:27
Hannah's freelance business is growing—bigger clients, bigger opportunities, and bigger risk. She's still working off handshake deals and email threads, and she wants to know exactly when a real contract becomes non-nego…
Stop Guessing Your Prices, Start Doing This [not-audio_url] [/not-audio_url]

Duration: 17:52
Sam is new to freelancing and stuck on a question every beginner faces: how do you charge for value when there's no hourly rate to fall back on? Preston and bestselling author Amy Suto break down what value-based pricing…
This Emotional Block is Killing Your Rates [not-audio_url] [/not-audio_url]

Duration: 18:18
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…
The $191K Substack That Changed Everything [not-audio_url] [/not-audio_url]

Duration: 19:46
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 $19…
Should You Ever Say 'No' to a Client? [not-audio_url] [/not-audio_url]

Duration: 18:29
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 tal…
Getting Your Clients to Respect You 100% [not-audio_url] [/not-audio_url]

Duration: 17:35
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 b…
Who Should Be Your First Hire? [not-audio_url] [/not-audio_url]

Duration: 22:31
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 j…