Freelance to Founder

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

Laura completed the work, sent the proposal, and then froze. The invoice is sitting there — unsent — because she's convinced this is the moment she loses a client she can't afford to lose. Clay and Preston dig into the freelancer's oldest enemy: the story you tell yourself before anything has actually gone wrong. They walk through exactly why she should send that invoice, how to respond if the client pushes back, and how to break the habit of catastrophizing before you've even given reality a chance. 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 Bridges posed a simple question in the Milo Mastermind community and it sparked a conversation Preston and Clay couldn't let go: does presenting yourself as a freelancer or as an agency actually make a difference in closing clients? The answer turns out to be more nuanced than a simple either/or. In this episode, Preston and Clay dig into the psychology of the sales pitch, why individual trust almost always drives the buying decision, and how the structure you choose—solo or team—should match the kind of client you actually want to work with. 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

Kevin did a brand redesign for an old colleague two years ago — got paid, and moved on. Now the client's new marketing manager is asking for the original InDesign source files to update the brand guidelines internally. Kevin knows the owner, considers him a friend, and doesn't want to damage the relationship. But he also doesn't want to just hand over his work and forfeit any future opportunities. Preston and Clay dig into who really owns those files, what the law says versus what good business sense says, and how to turn a potentially awkward situation into goodwill — maybe even a Google review. 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

Rachel Stone King still loves design and branding—but the business side of freelancing has started to feel like a weight she can't shake. The thought of networking, hunting for clients, and staying motivated has left her feeling overwhelmed and burned out. Preston and Clay dig into what's really going on beneath that feeling, why losing your passion isn't always a crisis, and what practical steps you can take to reconnect with the reason you started in the first place. 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

Kirstie runs a design business and a client emails her at 5:22 p.m. on a Friday needing an ad designed that same night. Sound familiar? Preston and Clay break down the real question behind rush fees—not just what to charge, but whether you should say yes at all. From setting clear boundaries with clients to knowing when a favor is actually worth it, this episode gives freelancers a practical framework for handling last-minute requests without burning out or building bad expectations. 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

Lanya has a freelance project in front of her, she's estimated the hours, and her client is open to either hourly or project-based pricing—so now what? Preston and Clay make the case that the real question isn't hourly vs. project-based at all. It's about understanding the value you bring to the table and pricing accordingly. From the mechanics of asking the right discovery questions to the mindset shift that separates six-figure freelancers from the rest, this episode breaks down the art of value-based pricing in a way that actually makes sense. 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

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

Matt runs Barrow Studio, a brand identity and strategy agency in Bristol, UK—and he's drowning in advice. Every newsletter, YouTube channel, and podcast promises a different "marketing golden ticket": build an email list, go all-in on social media, launch a course, appear on podcasts, host a podcast. The result? He's done none of it, and his agency still runs almost entirely on word-of-mouth referrals. Preston and Clay untangle the overwhelm and lay out a clearer, more honest framework for building a marketing system that actually fits where your business is right now. 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

Brittany runs her own design studio and knows she needs to get out from behind her screen and start meeting people face-to-face. The problem: she's shy, and local networking feels downright terrifying. Preston and Clay walk her through exactly how to break into the local business world without pretending to be someone she's not—from joining a BNI leads group to an unexpectedly genius $100-a-week community stunt that opens doors without a single sales pitch. 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

Emma Clark runs Clark Content Co. and has spent years managing projects from her inbox and a few spreadsheets—until now. With two contractors on board and plans to hire more, things are getting messy fast. Preston and Christine Olivas break down why defining roles and responsibilities is the real foundation of any good system, and share the surprisingly lean tech stack that keeps Christine's 25-person team running smoothly across complex, fast-moving agency engagements. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ Learn more about guest co-host, Christine → ⁠⁠https://www.linkedin.com/in/colivas/⁠⁠ — ⁠⁠https://nosingleindividual.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Omar has built something worth protecting—a roster of loyal clients who hired him as a freelancer and trust him personally. Now he's growing Vision Craft Studios into a full agency, and the hardest part isn't finding new clients. It's handing off the old ones. Preston and Christine Olivas, founder and CEO of No Single Individual, dig into what it really takes to transition client relationships to your team without breaking the trust it took years to build. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Layla from Bright Horizon Media has built something real — a small social media marketing agency with two part-time team members and real momentum. Now she's facing the question every growing agency owner hits: how much of your client revenue should you give to your sub-contractors? Is it cheating to charge high and pay low? Preston and Christine Olivas dig into the art of agency pricing, the mindset shift around articulating value, and why who you target matters just as much as what you charge. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Christine Olivas scaled from solo freelancer to leading a 24-person operation—but the path wasn't as simple as just "hire when you're busy." Preston and Christine dig into one of the most misunderstood decisions in freelancing: when to bring someone on, who to bring on first, and how to avoid trading one grind for another. If you're turning down work and losing sleep, this episode will help you figure out whether you're ready to grow—or just ready to burn out faster. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

CodeCrafter is talented, working hard, and building something real—but a nagging voice keeps whispering that he's not expert enough to charge more, land better clients, or call himself a professional. Preston digs into one of the most common mental traps freelancers fall into: waiting to feel ready before they act. This episode breaks down how to reframe what expertise actually means, why your clients don't need the world's best—they need someone who can solve their specific problem, and how to start building confidence not by knowing more, but by doing more. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Subcontracting can feel like a smart move—until you realize your business is quietly disappearing into someone else's brand. Sound familiar? In this solo episode, Preston digs into a question from Garrett, a 30-year-old nonprofit consultant who's starting to wonder: am I building my business... or just theirs? He's been subcontracting for a seasoned consultant, and the lines between "partnership" and "being swallowed up" are getting blurry fast. Merge, stay, or go solo? Preston walks through how to test your market without blowing up a valuable relationship, set real boundaries before resentment kicks in, and make the leap from subcontractor to independent consultant—without burning the bridges that got you here. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Dream client. Huge project. Zero team. Do you say yes and figure it out later—or build the team first and hope they stick around? Preston and Austin break down the classic chicken-and-egg trap every growing freelancer hits... and reveal a third option that could save your reputation, your sanity, and your shot at finally making the leap from solo to agency.Support our show sponsors → https://freelancetofounder.com/sponsorsSubmit your own question → https://freelancetofounder.com/askJoin Austin's Premium Community → ⁠⁠https://www.freelancecake.com/community⁠⁠Get Austin's Book, Free Money → ⁠⁠https://austin-l-church.kit.com/cf0feb3e27⁠This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Does your zip code actually matter to American clients? Dieter's freelancing from Europe and wondering if the US market is even worth chasing. The answer might surprise you. Preston and Austin break down why being "foreign" isn't the handicap you think it is — and how to flip your location into a competitive edge that US-based freelancers simply can't match. If geography's been your excuse, this episode pulls the rug right out from under it. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → https://www.freelancecake.com/community Get Austin's Book, Free Money → https://austin-l-church.kit.com/cf0feb3e27 This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

Think you're ready to hire a VA... but have no idea where to start? You're not alone. Every growing freelancer hits that wall — a million tasks, not enough hours, and zero clue who to trust with the work. In this episode, Preston sits down with Austin Church (founder of Freelance Cake Community) to break it all down. Austin brings 4+ years of real VA experience and shares the one thing most freelancers get wrong when hiring — plus his dead-simple framework for knowing exactly what to hand off first. Character vs. skills. Freedom vs. burnout. This one might change how you run your business. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ Join Austin's Premium Community → ⁠⁠https://www.freelancecake.com/community⁠⁠ Get Austin's Book, Free Money → ⁠⁠https://austin-l-church.kit.com/cf0feb3e27⁠ This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Austin Church dig into the fear of raising rates and what's really holding freelancers back from charging what agencies charge. Austin breaks down the psychology behind client decisions, why replacing you costs them more than you think, and how higher prices can actually make clients trust you more. If you're ready to stop trading time for too little money and start positioning yourself like the authority you already are... this one's for you. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → https://www.freelancecake.com/community Get Austin's Book, Free Money → https://austin-l-church.kit.com/cf0feb3e27 This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 those existing relationships, or start exploring new channels to reach a wider audience? Preston and Austin break down how to grow what's already working while branching out strategically through visual content and key partnerships. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Join Austin's Premium Community → https://www.freelancecake.com/community Get Austin's Book, Free Money → https://austin-l-church.kit.com/cf0feb3e27 This episode has been aired previously. Learn more about your ad choices. Visit megaphone.fm/adchoices