Are You Charging Too Little… On Purpose?

Are You Charging Too Little… On Purpose?

Author: Millo June 5, 2026 Duration: 20:10
Adam Barta's design agency just signed five clients in three days — and now he's wondering if it's time to raise his prices. The momentum is real, but so is the fear of charging too much and watching it all fall apart. Preston and guest co-host AJ Cassata from Revenue Boost walk through the art and science of pricing: how to test your limits incrementally, why a high close rate is actually a red flag, and how to start building agency-level pricing into your business before you ever hire your first employee. Links: Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask Attend The "10X Your Freelancing" Summit -> https://10XFreelance.com (FREE) 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
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…
5 Places to Get More Leads and Attention [not-audio_url] [/not-audio_url]

Duration: 20:09
Struggling to grow your freelance business and attract quality clients? In this episode of Freelance to Founder, Dr. Noah St. John breaks down his proven MAPSSS method for generating leads that can transform your busines…
These Habits May Be Holding You Back [not-audio_url] [/not-audio_url]

Duration: 24:22
Breaking free from self-imposed limitations isn't just about willpower—it's about understanding the deep-rooted habits that keep you stuck. In this eye-opening episode, Dr. Noah St. John reveals the psychological mechani…
How Long Does It Take to Succeed? [not-audio_url] [/not-audio_url]

Duration: 19:53
Freelancing promises freedom, but the path to steady income can feel uncertain. In this episode, Preston and Meredith dive deep into the strategies that help freelancers build a reliable revenue stream, sharing practical…
What We Wish We Knew Before Jumping In [not-audio_url] [/not-audio_url]

Duration: 17:48
Embarking on a freelance journey can feel like navigating uncharted waters. Many aspiring freelancers get stuck in the preparation phase, overthinking branding, websites, and perfect portfolios instead of taking the most…