Freelance to Founder

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

Melissa is spending hours on custom proposals—and she knows something is off. The pricing second-guessing, the laborious back-and-forth, the sinking feeling that all those unbillable hours may not even convert. Preston and Austin dig into why the traditional proposal process might be the problem itself, and lay out smarter, faster alternatives that can actually win more work with less wasted time. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Mark has built something real—a growing agency with contractors doing solid work and clients getting results. But success has come with an unexpected side effect: guilt. He's making money from other people's labor, and it doesn't sit right with him. Preston and Austin Church unpack where that guilt actually comes from, why it's often a sign of good character rather than bad business, and how to think clearly about fair pay, profit, and what you truly owe the people on your team. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

A question from Austin Church's Freelance Cake community puts tax strategy center stage: is taking an S-Corp election actually worth it? Preston and Austin break down the real mechanics behind this often-misunderstood move—how splitting your income between a salary and shareholder distributions can save you tens of thousands of dollars a year, why your state tax laws matter more than you might think, and exactly when it stops being worth the extra paperwork. If your freelance or agency revenue is approaching six figures, this is the conversation that could 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 Community for Advanced Freelancers -> ⁠⁠⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Hannah is ready to make her first hire and is seriously considering looking beyond U.S. borders — but she doesn't know what she doesn't know. In this episode, Preston is joined by Brian Samson, a three-time founder who has scaled recruiting agencies to $4 million ARR by building teams across Latin America and beyond. Together they walk Hannah through exactly how to approach international hiring for the first time: where to start, which regions tend to excel at what, how to think about time zones, and the blind spots that trip up most first-time international managers — including the costly "follow-the-sun" communication trap that can burn a full week on a single misunderstood task. 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 is getting pulled in every direction by his clients — new requests keep piling on top of the original project, and he doesn't know how to push back without risking the relationship. Preston and Austin Church, founder of the Freelance Cake Community, dig into exactly how to handle scope creep with confidence: from crafting airtight contracts and expectations docs, to the subtle language shifts that remind clients you're a business partner — not an employee on the payroll. Plus, when to just say yes anyway. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Maya has a clear goal: charge more. She's doing solid work, she's got clients, but she knows she's leaving money on the table—she just doesn't know how to structure a premium offering that actually feels worth the price tag. Preston and Austin dig into the real psychology behind high-ticket packages, from learning to charge for your thinking (not just your deliverables) to using the "magic wand" question to uncover what clients will actually pay a premium for. If you've been wondering how to move upmarket, this episode is the practical push you need. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Victor is a freelancer based in Berlin doing solid project work—delivering results, getting paid, and then watching clients disappear into the void. No follow-up, no next project, just silence. He wants to know how to build real, lasting client relationships instead of one-and-done engagements. Preston and Austin Church, founder of Freelance Cake, break down why clients go quiet (hint: it's almost never about you), how to build an offboarding process that keeps doors open, and how to plant the seeds of a long-term relationship before you even send the final deliverable. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Dana in Seattle went freelance for the freedom—and now she's drowning in deadlines and client expectations she can barely keep straight. Sound familiar? Preston and Austin Church unpack the promise that draws most people into freelancing in the first place, and whether the "no boss, no calendar" dream was ever really the point. Along the way, they share three dead-simple systems for keeping projects organized without the suffocation—including a one-page brief that replaces a hundred scattered emails and a counterintuitive trick involving more deadlines that actually sets you free. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Dave's agency is humming along, but everything — how he prices, how he delivers, how he handles problems — lives entirely in his head. It's worked so far, but he can feel it starting to strain. So he's asking the question every growing agency owner eventually faces: if I had to pick just one or two things to systemize first, what would they be? Preston, Sabrina, and Jesse P. Gilmore from Niche in Control dig into exactly that — walking through a practical, priority-ordered approach to getting out of your own head without turning your business into a corporate machine. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Connect with Jesse: - Website - ⁠https://www.nicheincontrol.com⁠ - LinkedIn - ⁠https://www.linkedin.com/in/jessepgilmore/⁠ - SAA trial - ⁠https://nicheincontrol.com/triangle⁠ - Book - ⁠https://www.nicheincontrol.com/book ⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Priya left her full-time job to build an agency on her own terms — and now finds herself buried under client obligations she can't seem to escape. Every new project feels like a trap, and turning down work feels like a risk she can't afford. Preston and Sabrina sit down with Jesse P. Gilmore of Niche in Control to map out exactly how agency owners can build for freedom instead of accidentally building another job — covering time systems, ideal client selection, offer design, and the mindset work that makes all of it stick. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Connect with Jesse: - Website - ⁠https://www.nicheincontrol.com⁠ - LinkedIn - ⁠https://www.linkedin.com/in/jessepgilmore/⁠ - SAA trial - ⁠https://nicheincontrol.com/triangle⁠ - Book - ⁠https://www.nicheincontrol.com/book ⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Marcus built his agency the hard way—doing everything himself until the clients came, the revenue got steady, and the team grew. But now, with real momentum on his side, he's still the one making every call, reviewing every deliverable, and firefighting every problem. He suspects this habit that once made him successful might now be the very thing capping his growth. Preston and Sabrina sit down with Jesse P. Gilmore from Niche in Control to help Marcus understand the difference between scrappy resourcefulness and a founder bottleneck—and what to actually do about it. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Connect with Jesse: - Website - https://www.nicheincontrol.com - LinkedIn - https://www.linkedin.com/in/jessepgilmore/ - SAA trial - https://nicheincontrol.com/triangle - Book - https://www.nicheincontrol.com/book Learn more about your ad choices. Visit megaphone.fm/adchoices

Lena is a new freelancer staring down one of the most universally dreaded moments in self-employment: tax season. She knows taxes are confusing, but she's not sure whether to invest in an accountant from the start or try to handle it herself. Preston and Austin Church—both of whom learned the hard way—share what they wish someone had told them earlier, including the costly mistake that set Preston back $20,000 to $30,000, and the simple mindset shift that makes all the difference. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Rashid wants to land clients outside his home country, but the unknowns are holding him back — different governments, tricky payment terms, and contracts that feel impossible to enforce across borders. Preston and Austin Church dig into exactly how to protect yourself when working with international clients, and their answer might surprise you: where a client lives matters far less than most freelancers think. The real work is learning to read the room early, set airtight expectations before a project begins, and build habits that filter out bad-actor clients no matter what country they're in. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Aisha is just starting out as a freelancer and wrestling with the question that trips up almost everyone in the early days: what should I actually charge? She knows she doesn't want to undersell herself, but she also has no idea where to set her rates. Preston and Austin Church—veteran freelancer and author of Free Money—unpack three different pricing approaches, make the case for building your rate around what your life actually costs, and explain why anchoring high (and negotiating scope, not price) is the move that separates confident freelancers from the ones who always feel underpaid. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠ Join Austin's Community for Advanced Freelancers -> Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Jenna finds herself wanting to build a successful business without sacrificing her values or family time. Preston Lee and Dawn Andrews share what it takes to design a leadership role that truly fits your life, offering compassionate insights for ambitious professionals navigating the complex terrain of work-life integration. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Dawn on Linkedin -> ⁠https://www.linkedin.com/in/freerangethinking/⁠ Listen to Dawn's Podcast -> ⁠https://open.spotify.com/show/5tFfxkHltyeAeetz9ao4pu Learn more about your ad choices. Visit megaphone.fm/adchoices

For Nicole, what started as a quest for freedom through freelancing has morphed into a complex leadership challenge—managing a team that seems to consume more time than the work itself. Preston Lee and Dawn Andrews explore the art of creating standard operating procedures (SOPs) that transform team management from a headache into a strategic advantage. They reveal the secrets to empowering your team, reducing management overhead, and reclaiming the entrepreneurial freedom you originally sought. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Dawn on Linkedin -> ⁠https://www.linkedin.com/in/freerangethinking/⁠ Listen to Dawn's Podcast -> ⁠https://open.spotify.com/show/5tFfxkHltyeAeetz9ao4pu Learn more about your ad choices. Visit megaphone.fm/adchoices

Amanda is standing at a pivotal moment in her leadership journey—wrestling with the internal doubts that plague many first-time team leaders. As she steps into her new role, the weight of proving herself feels overwhelming. Preston and Dawn Andrews dive deep into the psychology of leadership, revealing how vulnerability, communication, and embracing risk can transform imposter syndrome from a paralyzing force into a catalyst for growth and confidence. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Dawn on Linkedin -> https://www.linkedin.com/in/freerangethinking/ Listen to Dawn's Podcast -> https://open.spotify.com/show/5tFfxkHltyeAeetz9ao4pu Learn more about your ad choices. Visit megaphone.fm/adchoices

Jason from our listener community is stuck in a common entrepreneurial trap—feeling overwhelmed by the administrative demands of maintaining his LLC. Preston Lee and Bobby Casey dive deep into why business structure matters, how to manage compliance without losing your mind, and the critical steps every business owner needs to know about protecting their assets. Bobby Casey, founder of Business Anywhere and an international tax lawyer, breaks down the essential reasons why entrepreneurs should never shy away from proper business structuring. From liability protection to strategic asset management, this episode is your roadmap to understanding the sometimes mundane but critically important world of business administration. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask George's Freedom Builders Academy -> ⁠www.freedombuildersacademy.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Parker is stuck navigating the murky waters of freelance finance, desperate to transform his business from a mere survival mode into a strategic growth machine. Preston and George Thomas dive deep into the critical financial strategies that separate struggling freelancers from successful business owners. From understanding revenue forecasting to building a financial support team, this episode cracks open the playbook for freelancers ready to take control of their financial future and scale their businesses with confidence. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask George's Freedom Builders Academy -> ⁠www.freedombuildersacademy.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Lana has built a successful freelance career but finds herself paralyzed by the complexities of retirement planning. Preston Lee and financial expert George Thomas unpack the essential strategies for independent professionals to build sustainable wealth. Diving deep into retirement accounts, investment opportunities, and wealth-building tactics, this episode provides a comprehensive roadmap for freelancers looking to secure their financial future without the safety net of traditional employment. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask George's Freedom Builders Academy -> www.freedombuildersacademy.com Learn more about your ad choices. Visit megaphone.fm/adchoices

Lauren is navigating a pivotal moment in her entrepreneurial journey—her business has taken off since becoming a parent, but she's struggling to find harmony between her family's needs and her business ambitions. Preston and Lindsay dive deep into the messy, beautiful reality of being a parent-entrepreneur, sharing hard-earned wisdom about energy management, setting boundaries, and creating a life where both your family and your business can thrive. This episode is a raw, honest look at how to grow your dreams without losing sight of what matters most. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Lindsay -> ⁠⁠https://www.DearFoundHer.com⁠⁠ Follow Lindsay on Instagram -> ⁠⁠https://www.instagram.com/DearFoundHer⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Nicole is standing at a critical crossroads in her entrepreneurial journey. After leaving corporate America to start her own business, she's wrestling with doubts and financial uncertainty. Preston and Lindsay dive deep into the crucial strategies for new entrepreneurs facing this make-or-break moment: understanding that business success is a marathon, not a sprint, and learning how to navigate the challenging early stages of building your own venture. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Lindsay -> ⁠https://www.DearFoundHer.com⁠ Follow Lindsay on Instagram -> ⁠https://www.instagram.com/DearFoundHer Learn more about your ad choices. Visit megaphone.fm/adchoices

Amanda is standing at a critical crossroads in her entrepreneurial journey, wrestling with one of the most challenging questions every bootstrapper faces: How do I strategically spend my limited funds without taking on investors? In this powerful episode, seven-figure entrepreneur Lindsay Pinchuk breaks down the exact playbook for making smart financial decisions that can transform a bootstrapped business from surviving to thriving. With candid insights from her own entrepreneurial path—building a multi-million dollar company from just a $500 investment—Lindsay reveals the nuanced art of investing in your business, from strategic hiring to game-changing software and network opportunities that actually move the needle. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Lindsay -> https://www.DearFoundHer.com Follow Lindsay on Instagram -> https://www.instagram.com/DearFoundHer Learn more about your ad choices. Visit megaphone.fm/adchoices

Kevin is standing at a pivotal crossroads in his professional journey—transitioning from managing teams to becoming a solopreneur. Preston Lee and Moe Choice dive deep into the mental and strategic shifts required when moving from leading groups to leading yourself. With insights from Moe's extensive background as a six-time co-founder and leadership coach, this episode unpacks the emotional landscape of going solo, building support networks, finding the right mentors, and discovering the unique freedom of being your own boss. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠⁠ Connect with Moe on Linkedin -> ⁠⁠https://www.linkedin.com/company/moechoice/⁠⁠ Join Moe's FREE webinar -> ⁠⁠https://moechoice.com/podcast⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Daniel is trapped in a calendar packed with work, questioning the true meaning of a "freedom-based business." Preston and Moe dive deep into the nuanced world of solopreneurship, unpacking what freedom really means—and it's not just about having an empty calendar. From passionate contribution to strategic positioning, this episode reveals how to create a business that doesn't just provide income, but fuels your daily excitement and purpose. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Moe on Linkedin -> ⁠https://www.linkedin.com/company/moechoice/⁠ Join Moe's FREE webinar -> ⁠https://moechoice.com/podcast Learn more about your ad choices. Visit megaphone.fm/adchoices

Alex has built a solid freelance income but feels trapped in a cycle of trading time for money. Seeking to transform his business from a job-like grind to a strategic growth engine, he asks a critical question: How do you know when it's time to completely redesign your business or just keep working harder on what you've already got going? Preston and Moe dive deep into the strategies that help freelancers break free from the "bricklayer" mentality and become true business owners who sell transformative outcomes. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Connect with Moe on Linkedin -> https://www.linkedin.com/company/moechoice/ Join Moe's FREE webinar -> https://moechoice.com/podcast Learn more about your ad choices. Visit megaphone.fm/adchoices

When bad contractor experiences leave you gun-shy about hiring, how do you rebuild trust and create a successful team? Emily's struggle with past hiring mishaps is a common challenge for freelancers and agency owners. In this episode, Preston and Kevin Rice dive deep into the art of effective hiring, offering practical strategies for finding, integrating, and supporting contractors that truly add value to your business. From communication techniques to creating robust systems, they reveal how to transform hiring from a source of stress to a powerful growth strategy. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Connect with Kevin on Linkedin -> ⁠https://www.linkedin.com/in/kmrice/⁠ Listen to Kevin's podcast -> ⁠https://www.ceosandabcs.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Mark is stuck in the freelance grind—working nonstop and wondering how to transform his solo operation into a real company. Preston Lee and Kevin Rice dive deep into the critical moment when freelancers must shift from doing everything themselves to building a sustainable business. Drawing from Kevin's experience scaling a two-person startup to a 200-person agency with a nine-figure exit, this episode reveals the strategic secrets of knowing when and how to start delegating, hiring, and working on your business instead of in your business. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Connect with Kevin on Linkedin -> ⁠https://www.linkedin.com/in/kmrice/⁠ Listen to Kevin's podcast -> ⁠https://www.ceosandabcs.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Kevin Rice knows the delicate dance of entrepreneurship and fatherhood all too well. After scaling his digital agency to a nine-figure exit, he discovered the hard truth that success means nothing if it comes at the cost of your family connections. In this powerful episode, Kevin shares his personal journey of learning to be an intentional parent while building a thriving business, offering a roadmap for entrepreneurs struggling to balance professional ambition with meaningful family time. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠ Connect with Kevin on Linkedin -> https://www.linkedin.com/in/kmrice/ Listen to Kevin's podcast -> https://www.ceosandabcs.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Michael is standing at a critical crossroads in his entrepreneurial journey—desperate to break through the seven-figure barrier but unsure how to transform his current six-figure business into something truly scalable. In this episode, Charles Gaudet, CEO of Predictable Profits and renowned business coach, cracks open the playbook for moving beyond referrals and hard work into a strategic, demand-driven growth strategy. From leveraging LinkedIn to understanding the nuanced art of content creation and AI-proof marketing, this conversation is your blueprint for building a business that doesn't just grow, but multiplies. Support our show sponsors -> ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question -> ⁠⁠https://freelancetofounder.com/ask⁠ Connect with Charles -> https://www.linkedin.com/in/charlesgaudet/ Charles' Website -> https://predictableprofits.com/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Jordan is struggling with the modern remote work challenge—feeling like his brain never fully switches off. Preston and Steven dive deep into practical strategies for creating mental boundaries, exploring how freelancers and remote workers can design intentional work rituals that help them transition in and out of professional headspace. From creating dedicated workspaces to developing personal 'commuting' routines, this episode offers a roadmap for maintaining work-life balance in an always-on world. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Steven Puri's Focus App -> ⁠https://thesukkha.co⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Anthony is standing at a critical crossroads in his entrepreneurial journey—he's just hired his first two teammates and is wrestling with the most fundamental leadership challenge: how to spend his time effectively. Preston and Steven Puri dive deep into the art of leadership, unpacking the delicate balance between empowerment and oversight, and revealing the transformative power of deep work in a world increasingly dominated by AI and shallow tasks. From setting clear goals to creating space for meaningful strategic thinking, this episode is a masterclass for any freelancer transitioning from solopreneur to team leader. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Steven Puri's Focus App -> ⁠https://thesukkha.co⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Ethan has been hustling for three years, but feels stuck in a business that's just "meh". Preston Lee and Steven Puri dive deep into the critical strategies for transforming a stagnant freelance business into a thriving agency. From identifying true market pain points to finding authentic mentors who have actually achieved what you're aiming to do, this episode provides a raw, no-nonsense roadmap for breaking through entrepreneurial barriers and creating real business momentum. Support our show sponsors -> https://freelancetofounder.com/sponsors Submit your own question -> https://freelancetofounder.com/ask Steven Puri's Focus App -> https://thesukkha.co Learn more about your ad choices. Visit megaphone.fm/adchoices

Omar is standing at a critical crossroads in his business, wrestling with a fundamental hiring decision that could shape his team's future. Should he bring on a jack-of-all-trades virtual assistant who can handle multiple tasks, or invest in a specialized VA with laser-focused expertise? Preston Lee and Joey Vitale dive deep into the strategic nuances of VA hiring, revealing a framework that helps entrepreneurs make smarter team-building decisions that scale their businesses effectively. From understanding the power of generalist VAs as "Swiss Army knives" to recognizing when specialized talent becomes essential, this episode unpacks the art of building a flexible, high-performing remote team. Learn how to start small, create robust processes, and empower your virtual assistants to become true partners in your business growth. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠ Connect with Joey -> ⁠https://indielaw.com⁠ @TheJoeyVitale on all social media Learn more about your ad choices. Visit megaphone.fm/adchoices

Melissa is standing at a critical crossroads in her freelance business—overwhelmed by workload but paralyzed by the fear of delegation. Preston and Joey Vitale dive deep into the art of hiring your first virtual assistant (VA) without risking your business's reputation or quality of work. From accountability strategies to building emotional safety for new team members, this episode provides a roadmap for freelancers ready to scale their business while maintaining peace of mind. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠ Connect with Joey -> ⁠https://indielaw.com⁠ @TheJoeyVitale on all social media Learn more about your ad choices. Visit megaphone.fm/adchoices

Keisha's agency is at a critical turning point. As her business grows, she's wrestling with the ultimate entrepreneurial challenge: how to build a team without losing control or compromising quality. Preston Lee and Joey Vitale dive deep into the strategic art of hiring, revealing a nuanced approach to scaling your business from a one-person show to a thriving agency. From the risks of top-down hiring to the power of building a team from the bottom up, this episode is a masterclass in smart team expansion for freelancers ready to level up. Support our show sponsors -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠⁠ Connect with Joey -> ⁠https://indielaw.com⁠ @TheJoeyVitale on all social media Learn more about your ad choices. Visit megaphone.fm/adchoices

Hannah is wrestling with a critical question every growing freelancer faces—when and how to implement professional contracts that protect both parties and set the stage for successful client relationships. Preston Lee and business lawyer Joey Vitale crack open the playbook for creating contracts that do more than just protect your business—they build trust, clarify expectations, and serve as a powerful communication tool for freelancers looking to level up their professional relationships. In this episode, you'll discover how to transform contracts from intimidating legal documents into strategic assets that help you communicate clearly, set boundaries, and establish a foundation for long-term client success. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠⁠ Connect with Joey -> https://indielaw.com @TheJoeyVitale on all social media Learn more about your ad choices. Visit megaphone.fm/adchoices

Luis is standing at a critical crossroads in his agency's journey. Clients keep requesting additional marketing channels—email, influencers, partnerships—but he's worried about becoming a "do everything" agency that loses its core focus. Preston and Jason Fishman dive deep into the strategic art of service expansion, revealing how to grow your offerings without sacrificing quality or diluting your expertise. From finding your niche to intelligently adding complementary services, this episode is a masterclass in scaling your agency with intention and strategic insight. 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

Samantha is wrestling with one of the most critical challenges for new freelancers: how do you actually price your services based on value? Preston Lee and Amy Suto dive deep into the nuanced art of pricing your freelance work, breaking down the myths of the starving artist and revealing strategic approaches to valuing your unique expertise. From understanding the emotional weight of your deliverables to calculating a sustainable business rate, this episode is a masterclass in transforming your creative skills into a profitable 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

Beatriz has been a graphic designer for six years, working for others, but now stands at a critical crossroads. She wants to start freelancing as a digital artist but finds herself wrestling with an internal conflict: how can she confidently charge for her creative work without feeling like she's "selling out"? Preston Lee and Amy Suto dive deep into the psychological hurdles creatives face when transitioning from employee to freelance professional, offering a compassionate and strategic roadmap for valuing your art, understanding your worth, and building the confidence to get paid what you deserve. 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

David is at a pivotal moment in his writing career, caught between continuing lucrative client work and pursuing his dream of building a personal writing platform. Preston and Amy Sudo dive deep into the strategic approach of simultaneously serving clients while investing in your own intellectual property. From leveraging Substack to creating multiple income streams, this episode reveals the blueprint for transforming from a freelance writer to a writing entrepreneur who owns their creative destiny. 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

Natalie Chen is standing at a pivotal moment in her entrepreneurial journey, wrestling with a challenge many freelancers face: breaking free from being seen as just "the talent" and establishing herself as a true agency owner. Preston Lee and Jason Fishman dive deep into the strategic art of repositioning your business, revealing how to transform client perceptions from viewing you as a solo contractor to seeing you as a comprehensive, high-value agency with a talented team behind you. 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 stuck at a critical turning point in his freelance paid ads consulting business. Every time he tries to hire, his carefully built margins evaporate. Preston Lee and Jason Fishman dive deep into the strategic approach of scaling your agency, revealing the essential insights for hiring the right talent, structuring your offer, and ensuring each new team member contributes directly to your bottom line. 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 has achieved an incredible milestone, growing her business from a solo venture to a thriving team of 12 in just two years. But as her company expands, she faces a critical challenge: how to update her messaging, website, and social media to reflect her agency's growth while maintaining the personal touch that helped her succeed. Preston and Haley Raymond dive deep into the art of scaling your brand's story, revealing strategies for positioning yourself as an agency while keeping the human connection that makes your business unique. 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 is stuck at a critical moment in his freelance career—desperate to stand out but unsure how to transform his skills into undeniable expertise. Preston and Haley Raymond crack open the playbook for positioning yourself as the go-to professional in your field, revealing the strategic secrets of content creation, platform selection, and building a reputation that magnetizes clients. From leveraging LinkedIn to understanding the nuanced art of consistent, value-driven communication, this episode is your blueprint for breaking through the professional noise and becoming the expert everyone wants to hire. 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

Navigating the world of publicity can feel like a mysterious art, but it's actually an accessible strategy for freelancers and agency owners looking to amplify their message without paying out huge advertising bills. In this episode, PR consultant Haley Raymond breaks down the essentials of earned media, revealing how even small businesses can start building credibility and reaching new audiences through strategic publicity. 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

Transitioning from a solo freelancer to a business leader isn't just about hiring employees—it's about fundamentally changing how you approach work, leadership, and success. In this episode, Preston and Vijay dive deep into the critical mindset shifts required to move from being the person who does everything to the leader who enables others to do their best work. 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

Breaking free from the day-to-day grind isn't just a dream—it's a strategic necessity for freelancers and small business owners looking to transform their work. In this episode, Preston and Vijay Rajendran dive deep into how to create a meaningful vision and actionable roadmap for your business, offering insights that go far beyond traditional growth strategies. 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

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 Connect with Amy -> Book: ⁠https://amysuto.com/power⁠ Website: ⁠https://MakeWritingYourJob.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Freelancing offers incredible freedom, but it can also lead to overwhelming stress and exhaustion. Many freelancers find themselves trapped in a cycle of constant work, juggling client demands, marketing efforts, and administrative tasks. But it doesn't have to be this way. Support our show sponsors -> ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question -> ⁠https://freelancetofounder.com/ask⁠ Connect with Amy -> Book: ⁠https://amysuto.com/power⁠ Website: ⁠https://MakeWritingYourJob.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices