Freelance to Founder

Emily has hired contractors before, and it blew up on her—badly enough that she's not sure she can trust the process again. Preston and Kevin Rice, who scaled a business from two people to two hundred, break down why bad hires happen, how to rebuild systems (not just confidence) after getting burned, and why the real fix often has less to do with the contractor and more to do with how you communicate, onboard, and follow through. 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

Working around the clock and still can't shake the feeling that something's not sustainable—that's exactly where Mark finds himself. Preston sits down again with Kevin Rice, who turned a garage side project into a nine-figure agency exit, to unpack how he knew it was time to stop grinding solo and start building a team. From outsourcing your first project to walking away from clients like Pepsi, this episode is a real look at the risk, discipline, and timing behind turning freelance income into an actual company. 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

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

AI just rewrote the rules for getting found, and most freelancers haven't noticed. Charles Gaudet explains how AI tools are quietly building an "expert profile" on every business owner, scraping LinkedIn posts, podcasts, and reviews to decide who gets recommended and who disappears. Preston and Charles talk through what separates authentic, high-consumption content from AI slop, and why 2026 may leave zero room for the average, generic freelancer. 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

Jordan works remotely and can't seem to shut his brain off—work follows him everywhere, from his bathroom to Bali to a bench under a bridge. Preston and Steven Puri, a former film studio executive and three-time startup founder, break down how to build mental boundaries when you don't have a physical office. They dig into the power of ritual and physical association, sharing a wild story about the writers of Independence Day and a $5 million villa, to explain exactly how top performers train their brains to switch into—and out of—deep focus. 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

Anthony just hired his first two teammates and immediately feels the ground shift under him. Solopreneur instincts don't translate to leadership, and he's not sure where his time should go—sales, training, or growing the business. Preston and Steven Puri break down the difference between giving people tasks and giving them goals, and why real leadership means stepping back enough to let your team actually lead. 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

Ethan has been hustling for three years straight, doing everything the internet gurus told him to do—and his business is still just "meh." He can't afford to hire help, and he's starting to wonder if he's destined to stay a burned-out freelancer forever. Preston and Steven Puri, a former film studio executive who's raised over $21 million in venture capital, break down why most online advice is worthless, how to tell if you're solving a painful enough problem, and where to actually find mentors who've done the thing instead of just talked about it. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 the smarter first move, when client-facing or technical work demands a specialist from day one, and how to structure that first hire—hours, pay, and processes included—so it actually sticks. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 delegating without the risk, from running accountability calls to tracking key business metrics. They dig into how to build trust with a new teammate gradually, why emotional safety matters just as much as task lists, and how to know when you're ready to hand off bigger, client-facing work. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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? Preston and business lawyer Joey Vitale break down the difference between hiring employees and contractors, why "bottom-up" hiring often beats bringing on expensive experts too soon, and how to build a team that can run without you—even while you're on vacation. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join our FREE online event -> ⁠⁠https://10Xfreelance.com/⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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-negotiable. Business lawyer Joey Vitale joins Preston to break down why a contract isn't just legal armor, it's a communication tool that sets expectations, prevents scope creep, and keeps every client relationship on solid ground. They dig into the most common contract mistakes freelancers make, from generic templates to a simple LLC naming error that could put your personal assets on the line. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠ Join our FREE online event -> ⁠https://10Xfreelance.com/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 actually means in practice, from calculating a true hourly baseline to pricing in the emotional weight and complexity clients bring to a project. Whether it's ghostwriting a memoir or knocking out a quick copywriting job, they show how to size up a client and land on a number that actually reflects what the work is worth. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Buy Amy's new book -> ⁠https://amysuto.com/power⁠ Join Amy's substack -> ⁠https://www.makewritingyourjob.com/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 lack of confidence and the fear that taking money makes her a sellout. Preston and bestselling author Amy Suto dig into the mindset shift that separates hobbyists from professionals, why "solving a problem" beats "selling your art," and how to stand out in a world where AI can generate art in seconds. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Buy Amy's new book -> ⁠https://amysuto.com/power⁠ Join Amy's substack -> ⁠https://www.makewritingyourjob.com/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 $191,000 a year, to unpack how freelancers can turn their writing into equity instead of just income. They dig into paid newsletters, self-publishing, and the exact roadmap for building a writing career that doesn't depend on anyone else's business. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Buy Amy's new book -> ⁠https://amysuto.com/power⁠ Join Amy's substack -> ⁠https://www.makewritingyourjob.com/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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 talk through how to know when expanding your services makes sense, when it's a distraction, and why staying open to what the market sends you might matter more than sticking to a five-year plan. It's a practical look at growing on purpose instead of by accident. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Jason Linkedin -> ⁠https://www.linkedin.com/in/jafishman/⁠ Jason's Business -> ⁠https://www.digitalnicheagency.com/⁠ Jason's Podcast -> ⁠https://www.youtube.com/@digitalnicheagency Learn more about your ad choices. Visit megaphone.fm/adchoices

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 break down how to shift that perception, from positioning your team as thought leaders to building the right "emergency guardrails" that give clients confidence in letting go. This episode is a practical guide to repositioning yourself as a company rather than a one-person show, without losing the trust you worked hard to build. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Jason Linkedin -> ⁠https://www.linkedin.com/in/jafishman/⁠ Jason's Business -> ⁠https://www.digitalnicheagency.com/⁠ Jason's Podcast -> ⁠https://www.youtube.com/@digitalnicheagency Learn more about your ad choices. Visit megaphone.fm/adchoices

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 job? Preston and Jason Fishman, CEO of Digital Niche Agency, break down why your first hire shouldn't just be a copy of you, how to know if your pricing can carry a team, and what it really takes to turn solo income into scalable agency profit. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Jason Linkedin -> ⁠https://www.linkedin.com/in/jafishman/⁠ Jason's Business -> ⁠https://www.digitalnicheagency.com/⁠ Jason's Podcast -> ⁠https://www.youtube.com/@digitalnicheagency Learn more about your ad choices. Visit megaphone.fm/adchoices

Layla went from working solo to leading a team of 12 — but her website and socials still tell the old story. Preston and PR consultant Haley Raymond dig into how fast-growing service businesses should rebrand without losing the personal connection that got them clients in the first place. They cover the "we" vs "I" shift, when to lean into agency branding, and why keeping a human face out front still matters even as the team grows. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Connect with Haley: ⁠⁠⁠https://HaleyRaymond.com⁠⁠⁠ ⁠⁠⁠https://www.linkedin.com/in/haleyadams25/⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Andre knows he needs to position himself as the expert in his field, but he's stuck on how. More social media? More speaking gigs? Preston and Haley Raymond break down the real playbook: why LinkedIn tends to be the first stop for service providers, the difference between telling people you're an expert and showing them, and how to batch your content so consistency doesn't turn into burnout. They also dig into where AI tools genuinely help versus where they just create more noise. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠⁠ Connect with Haley: ⁠⁠https://HaleyRaymond.com⁠⁠ ⁠⁠https://www.linkedin.com/in/haleyadams25/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Haley Raymond spent years in newsrooms before becoming a publicist, so she knows exactly what makes a journalist say yes and what gets deleted on sight. Preston sits down with her to unpack earned media: the free but far-from-easy strategy of getting press, podcast features, and local news coverage without spending a cent on ads. They cover when a freelancer or agency owner should start thinking about PR, how to find your "story" even if you think your work is unremarkable, and why a tailored pitch always beats a mass email. If you've ever wondered whether you're ready for the spotlight, this episode lays out the roadmap. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Haley: ⁠https://HaleyRaymond.com⁠ ⁠https://www.linkedin.com/in/haleyadams25/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Fatima has been running solo for years and finally feels ready to lead a team—but she's stuck on how to actually think like a CEO instead of a freelancer doing everything herself. Preston and Vijay Rajendran break down the real transition between founder and executive, introducing the idea of becoming a "chief enablement officer" before you can become a chief executive one. They dig into building trust with new hires, using a RACI framework to clarify who owns what, and why letting go of control—not working harder—is what actually lets your business grow. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Vijay -> ⁠⁠⁠StartupSystem⁠⁠⁠  | ⁠⁠⁠Read My Book⁠⁠⁠ | ⁠⁠⁠Follow me on Substack⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Lucas runs a freelance business he knows has real potential — but every time he tries to think bigger, the daily grind of client work pulls him back in. He wants a genuine roadmap for growth, not just more hustle. Preston and Vijay Rajendran, founder coach at Startup System and partner at GAI Ventures, walk through what it actually takes to build that bigger vision: why your values have to come first, the simple three-part framework that keeps a growth roadmap grounded, and how to carve out the mental space to act like a CEO — even when your inbox is full. 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

Freelance writing can feel like a financial rollercoaster, with many creators struggling to price their services confidently. In this revealing conversation, Preston and Amy Suto crack open the complex world of freelance pricing, sharing hard-earned strategies that transform how independent professionals value their work. 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

Malik is juggling client work, marketing, and admin—and he's running on fumes. Preston and Amy Suto, creator of the bestselling Substack Make Writing Your Job and author of the upcoming Write for Money and Power, dig into why most freelancers burn out not from working too hard, but from undercharging, context-switching, and never actually deciding who they want to be. This episode is a practical and surprisingly personal look at how to restructure your week—and your identity—so you can grow without collapsing. 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

Amy Suto has built a seven-figure freelance writing career in an era when most writers are watching AI erode their client base. Her secret? Memoir ghostwriting — a niche so deeply human, so dependent on trust and storytelling craft, that no language model can touch it. In this episode, Preston sits down with Amy to explore what separates the freelancers who are thriving right now from those who are struggling, why the shift from "typist" to "storyteller" is the most important repositioning a writer can make, and how to think about AI as a powerful assistant rather than a career-ending threat. Whether you're a writer, designer, or marketer, this conversation is a blueprint for staying irreplaceable. 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

Jonas runs a solo service business and feels buried under tasks he can barely keep up with. He knows systems and automation are supposed to be the answer—but with everything on his plate, he has no idea where to even begin. Preston and Amy Suto, a seven-figure freelance writer and creator of the bestselling Substack Make Writing Your Job, walk Jonas through a practical framework for identifying what to automate first, why a time audit changes everything, and how managing your energy—not just your calendar—is the real secret to sustainable solo business growth. 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

Lucia has hired her first subcontractors—a milestone worth celebrating. But now she's spending more time correcting their work than she is on her own, and she's starting to wonder if the whole thing is worth it. Preston and Vijay Rajendran, startup coach and author of The Funding Framework, unpack the real reason delegation breaks down and lay out a practical spectrum—from direction to deferring—that helps leaders calibrate how much oversight each person actually needs. If you've ever found yourself quietly redoing someone else's work, this one's for you. 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

Nia has been freelancing solo for years and just landed the kind of project that changes everything—her first big team project. She's excited, but the reality is setting in fast: she can't do this one alone. Preston and Vijay Rajendran, founder coach at Startup System and partner at GAI Ventures, walk through what it really takes to go from lone freelancer to effective team leader. From identifying your zone of genius to knowing exactly what to look for in your first collaborators, this episode is a practical guide for anyone approaching that pivotal moment when the work gets bigger than one person. 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

Noah loves his work — but the moment it comes to promoting it, something freezes up. He knows he needs to market himself, yet every attempt feels either pushy or performative. Preston and George Azar, CPA and founder of Bright Budget, dig into why that discomfort is actually a signal worth paying attention to — and what to do about it. From understanding your real value, to finding the clients who genuinely need what you offer, this episode reframes the whole act of selling as something that can feel completely natural. 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

A freelancer scrolling through TikTok sees the same ad for the hundredth time: "Convert to an S-Corp and save $10,000 in taxes—easy!" Preston has seen it too. So has CPA George Azar, who has spent years cleaning up the mess left behind when people make the switch without understanding what it actually involves. In this episode, they break down what the S-Corp election really means, why the self-employment tax is the number that should actually scare you, and what the TikTok ads conveniently leave out—including the salary requirements, the payroll costs, and the moment the math stops working in your favor. 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

Alicia Martinez is running a freelance business and tracking every dollar in a spreadsheet. It's working — for now. But she's wondering if it's time to graduate to real bookkeeping software, or skip straight to hiring a professional. Preston and George Azar, CPA and founder of Bright Budget, break down the honest answer: it depends on where your business is headed, how comfortable you are with your numbers, and whether your time is better spent elsewhere. 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

Tanya has been freelancing full-time for a year, but her income swings wildly from month to month—and she has no idea how to build a budget around a paycheck that never looks the same twice. Preston and George Azar, CPA and founder of Bright Budget, walk through the practical money systems that actually work for self-employed people: from percentage-based saving and high-yield accounts to the structural business move that can finally give you a steady, predictable paycheck from your own company. 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

Sophia has a client who won't stop asking for small favors after the project wrapped. The work is done, the deliverable was handed off—and yet the requests keep trickling in. Preston and Chanda Coston break down how to set clear boundaries, build them into your contracts from the start, and even turn the situation into a recurring revenue opportunity. If you've ever felt awkward saying "that's going to cost extra," this one's for you. 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

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

Shalimdar quit his 9-to-5 as a UI/UX designer, went full-time freelance, and hit a new income high. The problem? He's working more hours than ever—and still doesn't feel like he owns his time. Preston and AJ Cassata from Revenue Boost dig into exactly why this happens and walk through a practical framework for diagnosing where your time is actually going, what to cut, what to automate, and what to hand off—so you can stop trading every hour for a dollar and start running your business like a founder. 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

Tamer put it bluntly on X: one week he's scrambling for leads, the next he's buried in work with no time to look up. It's the defining tension of freelance life—and it doesn't fix itself. Preston and AJ Cassata from Revenue Boost unpack why the feast-famine cycle is really a marketing problem in disguise, and what it actually takes to build the kind of predictable lead flow that makes growing an agency feel possible instead of reckless. 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

Poivino runs a design agency and he's hit a ceiling—his local clients don't pay what his skills are worth, and he knows it. He wants to break into the premium market: higher-budget clients, international companies, serious engagements. Preston and AJ Casada from Revenue Boost break down exactly how to make that leap, from building a digital presence that passes the credibility test to running targeted cold outreach campaigns that speak directly to the clients you actually want. 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

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

Meg has been freelancing for eight months and can't figure out why inquiries keep going cold. Her skills are solid, her rates are fair—but her portfolio just isn't closing the deal. Preston and Christine crack open what actually makes a portfolio convert, from the way you frame past work to what potential clients are really looking for when they land on your page. If your portfolio exists but isn't working, this episode will show you exactly where it's breaking down. 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

Clay knows firsthand that the wrong networking group doesn't just waste your time — it drains your energy and kills your momentum. After building his agency through intentional, high-quality connections, he's developed a sharp eye for spotting the groups worth joining and walking away from the rest fast. This episode breaks down the framework Clay uses to find communities built on genuine value, and how the right room can quietly become one of your most powerful growth engines. 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

Sarah delivered exactly what her client asked for—until the spouse entered the chat. Now the feedback is contradictory, the timeline is slipping, and the relationship feels like it's unraveling. This episode breaks down how to protect your process, set boundaries without burning bridges, and get a project back on track when an unexpected voice starts calling the shots. 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

Clay is buried in proposals and contracts—jumping between tools, second-guessing every software decision, and wondering why nothing ever feels quite right. Preston and Clay pull back the curtain on the client management tool conversation freelancers keep getting wrong. It turns out the search for perfect software is actually the problem—and what really moves the needle has nothing to do with features or pricing plans. 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