Remove Pain from Recurring Revenue

Remove Pain from Recurring Revenue

Author: Millo April 10, 2026 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 on paper, but as she started executing it, something felt off. The project work still lights her up; the repetitive marketing tasks do not. Now she's wondering if she has to keep doing work she doesn't enjoy just to hit six figures, or if there's another way. Preston and Clay dig into why following someone else's exact blueprint can quietly lead you away from the work you actually love—and how to build a thriving, recurring-revenue business around just the services that energize you. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ Check out Clay's business → ⁠⁠https://golinus.com 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: 100

Freelance to Founder
Podcast Episodes
Why We Struggle to Delegate [not-audio_url] [/not-audio_url]

Duration: 20:04
Delegation is the critical skill that separates struggling freelancers from successful business founders. In this episode, Preston Lee and Vijay Rajendran break down the complex art of managing subcontractors, offering a…
How to Navigate Your First Big Project [not-audio_url] [/not-audio_url]

Duration: 18:24
Growing your freelance business often means taking on larger projects that require collaboration. But how do you successfully manage a team when you've been a solo operator? In this episode, Preston Lee and special guest…
Why You're Still Afraid to "Sell" Yourself [not-audio_url] [/not-audio_url]

Duration: 16:01
Feeling uncomfortable promoting your business? You're not alone. Many freelancers struggle with the fine line between effective self-promotion and feeling like a pushy salesperson. In this episode, Preston Lee and George…
The Real Truth About S-Corps (Don't Get Tricked) [not-audio_url] [/not-audio_url]

Duration: 28:33
Navigating the world of business taxes can feel like walking through a minefield of conflicting advice and flashy marketing promises. In this eye-opening episode, Preston and George Azar pull back the curtain on S-Corp e…
Should You Hire a Bookkeeper? (This Might Surprise You) [not-audio_url] [/not-audio_url]

Duration: 18:12
Managing finances can make or break a freelance business. In this episode, CPA George Azar breaks down the critical decisions around tracking your money – from simple spreadsheets to professional bookkeeping services. If…
How to Budget When Your Income Fluctuates [not-audio_url] [/not-audio_url]

Duration: 21:02
Freelancing offers incredible freedom, but it also comes with financial uncertainty. If you've ever stressed about managing your money when paychecks vary from month to month, you're not alone. In this episode, Preston a…
Client Asks for Favors—What Should I Do? [not-audio_url] [/not-audio_url]

Duration: 13:43
Freelancing can be challenging, especially when clients expect ongoing work without additional compensation. In this episode, Preston and Chanda Coston dive deep into a common freelancer dilemma: how to handle clients wh…
Switch From Hourly to Flat Rate (w/out Losing Money) [not-audio_url] [/not-audio_url]

Duration: 18:01
Switching from hourly to flat rate pricing can feel like navigating a minefield for freelancers. In this episode, Preston and Chanda break down the strategies that will help you confidently transition your pricing model,…
Is It Best to Drop Late-Paying Clients? [not-audio_url] [/not-audio_url]

Duration: 14:25
Freelancing offers freedom, but it can also bring financial uncertainty—especially when clients drag their feet on payments. In this episode, Preston and Chanda dive deep into a common freelancer nightmare: managing clie…
Should You Fill Income Gaps w/ Low-Paying Clients? [not-audio_url] [/not-audio_url]

Duration: 20:09
Every freelancer faces moments of financial uncertainty. When bills are mounting and opportunities seem scarce, the temptation to accept low-paying work can feel overwhelming. But is compromising your rates really the sm…