BusinessEntrepreneurshipEducationSelf-Improvement

Freelance to Founder

Millo

Freelance to Founder is a call-in show helping real-life freelancers grow their businesses and escape the feast-famine lifestyle.

The podcast is hosted by Preston Lee, a former freelancer who has started, built, and even sold successful businesses of his own.

Preston is joined nearly every weekday by other expert founders, freelancers, and entrepreneurs to help you take your solo business to the next level.

You can submit your questions at FreelanceToFounder.com/ask

If you enjoy content from shows like The Futur, Being Freelance, The Accidental Creative, Smart Passive Income, or The Side Hustle Show, then you'll love Freelance to Founder.

Join us every weekday to take the next step on your journey from ... freelance to founder.

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55 episodes
daily
Avg 19 min
English

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Today · 15 min
Do Clients Actually Care If You're an "Expert"?
CodeCrafter's skills are solid and his work speaks for itself, but he keeps holding back. Charging more feels presumptuous, and calling himself an expert feels like a lie. Preston unpacks why so many talented freelancers stay stuck waiting for a confidence that never shows up on its own. This episode redefines expertise from the client's point of view and gives you a practical way to stop second-guessing yourself and start acting like the professional you already are. 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
Friday · 13 min
Is Subcontracting Quietly Erasing Your Business?
Garrett is a 30-year-old nonprofit consultant doing great work for a seasoned consultant. The problem is that almost nobody knows it's his work. The more he delivers, the more his name fades into someone else's brand, and the line between partnership and being swallowed up gets blurrier every month. In this solo episode, Preston helps Garrett weigh three paths: merge, stay, or go solo. He covers how to test the market without putting a valuable relationship at risk, how to set boundaries before resentment builds, and how to go independent without burning the bridge that got you started. 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
Thursday · 19 min
Should You Go For Giant Projects?
A solo designer finally gets the call from a big-name client, and it's the kind of project that could turn a freelance business into a real agency. Excitement turns to panic fast, though, because nobody's there to help deliver it. Preston and Austin tackle the question every ambitious freelancer faces sooner or later: grow the team first, or win the work first? They also share a lesser-known approach that lets you say yes with confidence, without hiring before you're ready. 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
Wednesday · 18 min
Non-US Freelancer: Roadblock or Excuse?
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
Tuesday · 21 min
"I'll Just Do It Myself" = Burnout
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
September 28 · 22 min
Undercharging… or Just Scared?
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
September 25 · 22 min
Referrals Work... But is it Enough?
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
September 24 · 23 min
The Fix to Scope Creep
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
September 23 · 20 min
How Do You Package a $10K Offer?
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
September 22 · 18 min
Client Ghosted You? Here's What To Do
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
September 21 · 20 min
Don't Let Your First Hire Backfire
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
September 18 · 20 min
Say Goodbye to Anxiety with This Deadline Trick
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
September 17 · 19 min
Is LinkedIn Still Worth Your Time?
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
September 16 · 18 min
This Follow-Up Habit is Gold
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
September 15 · 20 min
Charging 2X for the Same Job?
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
September 14 · 19 min
You Need a Vacation
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
September 11 · 23 min
Chasing Clients vs Choosing Clients
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
September 10 · 26 min
Eliminate, Automate, Delegate
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
September 9 · 18 min
The Tax Mistake That Cost Me $30K
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
September 8 · 19 min
Red Flags Every Freelancer Should Know Before Signing
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

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