Freelance to Founder

Dieter is weighing a big question from his home base in Europe: is it worth going after US clients at all, or is he fighting a battle he can't win? Preston and Austin show that the playing field is more level than it looks, and in some ways it tilts in his favor. They cover how to handle client doubts, build trust across borders, and turn "I'm not in the US" into a reason to hire you. For anyone who has used geography as an excuse, this episode takes that excuse away. 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 is buried in admin work, turning down good projects and missing dinners at home. The fix seems obvious: hire a VA. But which tasks should go first, and how do you find someone you can trust? Preston and Austin Church, founder of Freelance Cake Community, answer both. Austin draws on more than four years of working with VAs to show where most freelancers go wrong, why character comes before skills, and how to pick the first tasks to hand off so you get your time back. 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 sits down to send a quote. The work is agency-level and the results are real, but the number that goes out is half of what an agency would charge. The reason isn't skill. It's fear of what the client will say. Preston and Austin Church dig into the psychology behind raising your rates: what clients actually weigh when they decide, why replacing you costs them far more than you think, and how a higher price can make them trust you more. If you're ready to stop trading your time for too little money and start pricing 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

Lana runs Homewear Designs, and real estate agents in New York and the Hamptons keep sending her home staging jobs. The referrals are steady and the business is healthy, but growth depends on how many agents she knows. She wants more than that. Preston and Austin look at how to get more out of the relationships she already has, and how to add new channels like visual content and partnerships without pulling focus from what's paying the bills. 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

Andre from New York keeps watching his projects balloon past their original scope, and he's tired of feeling like the bad guy for saying no. Preston and Austin Church break down exactly how to set boundaries without blowing up the relationship: scripts for replying to scope-creep requests in writing, when to bill extra versus push a request to phase two, and why most clients aren't trying to take advantage of you — they've just forgotten what's in the contract. It's a practical playbook for protecting your time while keeping clients coming back for more 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

Maya wants to offer more high-ticket services, but she's stuck on how to package them without just pulling a number out of thin air. Preston and Austin break down the exact process for structuring premium offers, starting with the price first and then reverse-engineering the value that justifies it. From identifying the invisible work clients already do around your deliverables to running real client interviews that reveal blind spots, this episode hands Maya, and you, a repeatable framework for building offers people are excited to pay a premium for. 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

Victor is doing great work for his clients in Berlin, but once the deliverables ship, the emails stop coming. He's left wondering if he did something wrong or if this is just how freelancing works. Preston and Austin Church break down why client silence rarely means what you think it means, and share the exact follow-up cadence and offboarding process that turns one-time projects into long-term partnerships. From testimonials to timed check-ins, this episode gives Victor—and every freelancer facing the same silence—a real plan for staying top of mind. 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

Hannah is ready to make her first hire, but she's stuck on one big decision: stay local or go global. Brian Samson, founder of Plugg Technologies and a three-time agency builder, joins Preston to break down what actually separates a great international hire from a costly mistake. They dig into which regions fit which management styles, why the follow-the-sun model can quietly burn out a team, and how to avoid losing a week over one unclear instruction. 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

Dana runs her freelance business hoping to stay organized without sacrificing the freedom she went into business for in the first place. Preston and Austin Church share the exact project brief template, planning ritual, and weekly status report habit that keep clients happy and deadlines met, then dig into the bigger question underneath it all: what freedom actually looks like when you're the one responsible for every deadline. 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 has been posting consistently on LinkedIn, but the algorithm keeps shifting and her feed leaves her frozen, unsure where to spend her limited time. Austin Church breaks down three practical habits—targeted commenting, building a dream client list, and messaging profile visitors—that turn a few minutes on LinkedIn into real client relationships. Preston and Austin share the exact bookmarking system, comment frameworks, and DM approach that keep the algorithm working in your favor instead of against 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

Melissa wants to sell more consistently, so she asks Austin Church and Preston to walk through their actual sales process, step by step. They break down the handoff from marketing to sales, the deck that builds trust before a call even happens, and the recap email that turns a good conversation into a clear next step. The conversation lands on the habit most freelancers skip: consistent, personalized follow-up that turns hesitation into a decision. 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

Mark and a few others in Austin Church's Freelance Cake community keep running into the same wall: a client asks for a website or a logo, but the deeper conversation reveals they actually need a strategy first. Do you upsell them on the spot and risk scaring them off, or just deliver what they asked for and eat the extra work for free? Preston and Austin break down exactly when to introduce a strategy engagement, how to phrase the offer without sounding like a bait-and-switch, and the four pricing containers — from a quick clarity call to a full strategy sprint — that let you charge for expertise you've been giving away. 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

Dave's agency works, for now. Pricing, delivery, client issues—it's all running through his head, and he's starting to feel it crack under the weight. Jesse P. Gilmore, founder of Niche In Control, joins Preston and Sabrina to map out exactly which systems to build first, from client onboarding to capturing the tribal knowledge that only exists in a founder's brain. Sabrina pushes the conversation further, asking what systemizing looks like when your service is literally yourself. It's a practical, no-fluff roadmap for anyone ready to stop being their business's single point of failure. 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 built her agency to escape the nine-to-five, but somewhere along the way, the business started running her instead. She's taking on every client that comes her way, terrified that saying no will kill her momentum. Preston, Sabrina, and Jesse P. Gilmore unpack the five-step framework for reclaiming time, documenting your work, and pricing based on value instead of hours—plus why getting selective about clients is what actually lets an agency grow. This episode is a wake-up call for any founder who's traded one kind of burnout for another. 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 built his agency by doing everything himself, and it worked—until it didn't. Now he's got steady clients, recurring revenue, and a small team, but he's still making every decision, reviewing every deliverable, and jumping in the moment something goes wrong. Is that scrappy founder energy, or is it holding the business back? Preston, Sabrina, and agency coach Jesse P. Gilmore break down the exact framework for figuring out what to eliminate, automate, and delegate—and why the shift from self-employed to business owner starts with knowing your unique ability. 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

Lena is staring down her first tax season as a freelancer and wants to know whether she should hire an accountant right away or figure it out herself. Preston and Austin Church share the expensive lessons they each learned the hard way — including a mistake that cost Preston tens of thousands of dollars — and lay out exactly when it makes sense to bring in a CPA versus when you can DIY. They dig into S-corp elections, bookkeeping systems, and the book that finally made cash flow click for both of them. 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

Rashid is ready to take on international clients, but he keeps hesitating over how to protect himself if a contract dispute crosses borders. Preston and Austin argue that a contract isn't really about winning in court — it's about setting expectations before the work even begins. They walk through the deposit rules, red flags, and reference checks that keep freelancers from getting burned, whether their next client is down the street or halfway around the world. 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

Aisha wants to charge what she's worth, but like most beginner freelancers, she isn't sure where to start. Preston Lee and Austin Church tackle the age-old pricing question head-on, walking through the pitfalls of using your old salary as a benchmark and the trap of pricing based on what your freelance friends charge. They introduce two numbers every freelancer needs — a survival rate and a dream rate — and explain how packaging your work, not just your hourly rate, can be the difference between charging $1 or $3 for the same lettuce. It's a practical, no-fluff guide to setting prices that keep you in business and paid what you deserve. 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

Jenna wants to grow a successful business without losing the family life she cares about most. Preston and business strategist Dawn Andrews dig into what it actually takes to build a career on your own terms, separating true values-based decisions from the guilt so many ambitious women carry. They swap real stories, from raising kids while running a business to blocking off six weeks of vacation and building the year around it, landing on one clear idea: your work should fit your life, not the other way around. 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

Somewhere between freelancing solo and running a full team, Nicole lost the freedom she built her business for in the first place. Preston and Dawn Andrews unpack the messy middle of management, where leaders mistake a process problem for a people problem, and share a simple, collaborative way to build standard operating procedures your team will actually use. From word-vomiting your vision into AI to running a low-stakes test before it matters, this episode is a roadmap back to the freedom Nicole started chasing. 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

Amanda is leading a team for the first time, and every meeting feels like an audition. She second-guesses her ideas, questions her own qualifications, and can't shake the sense that eventually everyone will figure out she doesn't belong in the room. Should she wait until she feels ready, or lead anyway? Preston and business strategist Dawn Andrews unpack why vulnerability builds more trust than having all the answers, how taking strategic risks quiets imposter syndrome over time, and why the leaders who admit what they don't know often earn the most respect from their teams. 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 wants out of his LLC. Between renewals, state fees, and filings, it feels like the paperwork is running his business instead of the other way around. Preston sits down with international tax lawyer Bobby Casey to make the case for sticking with it, and for finally outsourcing the parts that are draining his time and energy. They cover the liability protection most freelancers underestimate, the privacy risks of registering an entity yourself, and the cheap, automated tools that can take renewals, bookkeeping, and compliance completely off a founder's plate. 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

Growth sounds great until you realize you can't actually explain your own finances. That's where Parker finds himself—profitable, but nervous about scaling without a handle on his numbers. George Thomas, a financial coach with 15 years of experience, walks through the exact order of operations: get a CPA, forecast your revenue monthly, and routinely interrogate your expenses. It's a practical roadmap for any freelancer wondering if they're ready for the next level. 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

Arav is doing the math freelancers dread: no employer match, no automatic 401k, and a growing business that seems to pay off faster than any stock ever could. Preston and financial coach George Thomas dig into where retirement planning fits for someone building their own income, unpacking net worth, investment timing, and why a Roth IRA might be the most underused tool in a freelancer's financial toolkit. 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

Lauren's business took off right after she became a parent, and now she's caught between two things pulling at her time. Should the business get the same energy that made it grow, or does motherhood come first? Preston and Lindsay Pinchuk, who built her own company while raising kids, unpack why "balance" is the wrong goal entirely and what to focus on instead—setting boundaries, learning to say no, and asking for help before you're forced to. 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

Nicole is staring down a decision a lot of new business owners face: stick it out or go back to corporate. Preston and Lindsay Pinchuk share the exact email and LinkedIn strategy that took Lindsay from zero revenue-generating clients to three in under two weeks, plus honest talk about the timeline it really takes to know if a business is working. If you're wondering whether you gave your business enough of a shot, this episode is 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

Amanda wants to grow her business without giving up equity, but every dollar feels precious right now. Preston and Lindsay Pinchuk dig into the real framework for deciding what's worth paying for—hiring help before it feels affordable, testing software before committing to it, and even outsourcing chores at home to buy back time. Lindsay draws on her own journey from corporate burnout to building a community that reached three million people a month, showing Amanda how the smallest early investments can create the biggest returns. 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

After years of leading teams, Kevin wants to go solo — but he's worried about losing the structure and support that came with managing people. Moe Choice, a six-time co-founder turned solopreneur coach, shares the exact moment he realized independence didn't mean isolation, and the three-step framework he now teaches: commit fully to going solo, build a circle of support, and find mentors who are living the specific life you want. Preston and Moe unpack what nobody tells you about trading a team for total ownership of your time. 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

Daniel's calendar is packed, his to-do list never ends, and he's starting to wonder if "freedom" was ever real to begin with. Preston and Moe Choice get into a candid, sometimes contentious conversation about the different types of freedom—time, money, mental, emotional—and why loving what you do might matter more than how much of it you're doing. They also tackle a harder question: what happens when you have kids, bills, and a runway that's running out fast? 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

Moe Choice left the co-founder life to build a solopreneur business on his own terms, and now he's helping others do the same. In this episode, he and Preston tackle a question from listener Alex, who feels trapped by his own freelance success. They dig into the mindset shift from bricklayer to cathedral builder, why chasing hours keeps you stuck, and how repositioning your offer around outcomes—not tasks—attracts bigger clients who trust you enough to leave you alone. 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

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