More Clients, Less Freedom — What Went Wrong?

Marcus Thompson is a copywriter ready to ditch hourly billing—but he's worried that switching to flat-rate pricing means leaving money on the table. Preston and Chanda Costin walk through exactly how to make the move: from researching competitor rates and piloting packages with a small group of clients, to navigating the trickier conversation of transitioning existing clients off the hourly model. They also unpack why flat-rate pricing is actually a reward for getting better at your craft, and how the way you talk about your services determines whether clients see you as a commodity or an investment. 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

Priya has a client she genuinely enjoys working with—the work is solid, the money is good, and the relationship is smooth. The problem? They never pay on time. Not occasionally late. Chronically, reliably, always late. And the cashflow stress it's creating is starting to affect her whole business. Preston and Chanda Coston dig into how to have the hard conversation about payment terms, how to restructure contracts to protect yourself, and why solving this one problem might be the unlock that finally makes your business scalable. 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

Jasmine Lee is weighing a decision that trips up nearly every freelancer at some point: a potential client wants to pay less than her rate, and there's a gap in her income that makes the offer tempting. She wants to know if filling that gap with a low-paying client is ever a smart move—or if it always comes back to bite her. Preston and business strategist Chanda Costin dig into the pricing psychology behind the question, when holding the line is non-negotiable, and the specific situations where a little flexibility might actually make sense. 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

Bremley is running a real business — four clients, $8,100 in monthly recurring revenue — and he wants to know how to scale it. He's already proven he can close. Now he needs the leads. Preston sits down with Dr. Noah St. John, the "Zero Friction Doctor" and bestselling author of 25 books, to walk Bremley (and every freelancer hungry for growth) through a step-by-step system for generating warm, qualified leads without burning cash on ads before you're ready. 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

Dr. Noah St. John has spent his career helping Hollywood celebrities, professional athletes, and nine-figure CEOs break through the invisible ceiling holding them back. Now he brings that same framework to freelancers who know exactly what they want to build—but keep getting in their own way. Preston and Dr. Noah dig into the real reason so many freelancers struggle to level up: it's not a strategy problem, it's a habits problem. From dismantling the myth of willpower to understanding why your brain would rather doom scroll than grow your business, this episode is a practical breakdown of how to finally stop self-sabotaging and start moving. 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

Kwame is wrestling with a question almost every freelancer has whispered to themselves late at night: when does the money actually get steady? Preston and Meredith Cooley—founder of Page and Purpose and a mentor for teachers stepping into copywriting—dig into what consistent income really requires: consistent marketing, consistent sales, and the sometimes-uncomfortable habit of reaching out to clients you've never met. They share what it takes to move from feast-and-famine cycles to a business with real, predictable rhythm. 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

Diego Morales is thinking about making the leap into freelancing and wants to know what seasoned freelancers would do differently if they could start over. Preston and Meredith Cooley—founder of Page and Purpose and a copywriter-turned-mentor for teachers—share the honest, practical lessons that most "how to freelance" guides get completely wrong. From skipping the logo obsession to the slow-burn reality of building a side business, this episode is a candid look at what actually matters when you're starting out. 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

Aisha Raman wants to know the single biggest lesson you learn when you first go out on your own. Preston and Meredith Cooley—copywriter, educator-turned-entrepreneur, and founder of Page and Purpose—have a lot of ground to cover. From the sneaky pull of shiny object syndrome to the surprising difficulty of managing your own time when no one else is watching, this conversation gets honest about the real growing pains of building a freelance business. If you're in the early days of figuring this out, you'll find a lot to take with you here. 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

A Reddit question sparks a conversation that hits close to home for thousands of side-hustling professionals: a full-time teacher wants to know how to balance a demanding classroom career with landing and serving their first freelance clients. Preston sits down with Meredith Cooley—former 17-year educator turned full-time copywriter and teacher-to-freelancer mentor—to dig into the real, unglamorous work of building something on the side when your day job leaves almost nothing in the tank. From mindset shifts to a surprisingly simple paper-and-pencil time audit, this episode is a practical guide for anyone trying to grow a freelance business without quitting their day job first. 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

Tharun is ready to take the leap into freelancing—but one question is standing between him and his first paycheck: how do you actually land that very first client? Preston and AJ Cassata from Revenue Boost share their own origin stories (a bagel shop, a school yearbook, a wave of cold calls) and break down the two simplest moves any new freelancer can make to get that first client through the door. No complicated funnels, no elaborate lead gen systems—just smart, human approaches that actually work when you're starting from zero. 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