Can You Raise Rates w/out 'Scaring' Away Clients?

Can You Raise Rates w/out 'Scaring' Away Clients?

Author: Millo October 31, 2025 Duration: 19:40
Preston and guest AJ Cassata dive deep into the art of pricing, revealing how freelancers can confidently raise their rates without losing momentum. Learn the counterintuitive strategies that can help you attract better clients, work less, and earn more. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with AJ -> https://www.youtube.com/@ajcassataofficial https://www.linkedin.com/in/ajcassata/ 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
Are You Charging Enough to be an Agency? [not-audio_url] [/not-audio_url]

Duration: 21:59
Still leaving money on the table? Here's the uncomfortable truth: most freelancers underprice themselves—not because they lack skill, but because they're scared of what clients will say. In this episode, Preston and Aust…
When You Just Need More Clients... [not-audio_url] [/not-audio_url]

Duration: 21:59
Lana runs Homewear Designs and has built a steady stream of home staging clients through real estate agent referrals in New York and the Hamptons. It's working — but she wants to scale up. Is it smarter to double down on…
Proposals = Waste of Time? [not-audio_url] [/not-audio_url]

Duration: 23:00
Melissa is spending hours on custom proposals—and she knows something is off. The pricing second-guessing, the laborious back-and-forth, the sinking feeling that all those unbillable hours may not even convert. Preston a…
Feeling Major Guilt [not-audio_url] [/not-audio_url]

Duration: 20:51
Mark has built something real—a growing agency with contractors doing solid work and clients getting results. But success has come with an unexpected side effect: guilt. He’s making money from other people’s labor, and i…
Is an S-Corp Election a Smart Move? [not-audio_url] [/not-audio_url]

Duration: 18:55
A question from Austin Church's Freelance Cake community puts tax strategy center stage: is taking an S-Corp election actually worth it? Preston and Austin break down the real mechanics behind this often-misunderstood mo…
Scared to Hire Overseas [not-audio_url] [/not-audio_url]

Duration: 20:39
Hannah is ready to make her first hire and is seriously considering looking beyond U.S. borders — but she doesn't know what she doesn't know. In this episode, Preston is joined by Brian Samson, a three-time founder who h…
The Best Way to Handle Scope Creep [not-audio_url] [/not-audio_url]

Duration: 20:16
Andre is getting pulled in every direction by his clients — new requests keep piling on top of the original project, and he doesn't know how to push back without risking the relationship. Preston and Austin Church, found…
How to Sell High-Ticket Services [not-audio_url] [/not-audio_url]

Duration: 19:53
Maya has a clear goal: charge more. She's doing solid work, she's got clients, but she knows she's leaving money on the table—she just doesn't know how to structure a premium offering that actually feels worth the price…
Stuck with One-Time Clients [not-audio_url] [/not-audio_url]

Duration: 18:49
Victor is a freelancer based in Berlin doing solid project work—delivering results, getting paid, and then watching clients disappear into the void. No follow-up, no next project, just silence. He wants to know how to bu…
Is Freelancing Freedom a Lie? [not-audio_url] [/not-audio_url]

Duration: 20:14
Dana in Seattle went freelance for the freedom—and now she's drowning in deadlines and client expectations she can barely keep straight. Sound familiar? Preston and Austin Church unpack the promise that draws most people…