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PODCAST

Freelance to Founder

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

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All Episodes

24:04

Pay Gap: Freelancers vs. Agencies

Freelance to Founder ·

2026/04/17

Amy Bridges posed a simple question in the Milo Mastermind community and it sparked a conversation Preston and Clay couldn’t let go: does presenting yourself as a freelancer or as an agency actually make a difference in closing clients? The answer turns out to be more nuanced than a simple either/or. In this episode, Preston and Clay dig into the psychology of the sales pitch, why individual trust almost always drives the buying decision, and how the structure you choose—solo or team—should match

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14:40

Letting Go of Source Files = Good Idea?

Freelance to Founder ·

2026/04/16

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

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14:27

Love Your Craft, but Tired of Business?

Freelance to Founder ·

2026/04/15

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

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20:10

The Power of Saying "No" To Crazy Clients

Freelance to Founder ·

2026/04/14

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

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17:04

Don't Charge by Hour or Project. Do this...

Freelance to Founder ·

2026/04/13

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

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22:09

Remove Pain from Recurring Revenue

Freelance to Founder ·

2026/04/10

Erica is a web and graphic designer who invested in a coaching program built to turn designers into full-service marketers—complete with monthly retainers, ad campaigns, and recurring revenue. The strategy looked great on paper, but as she started executing it, something felt off. The project work still lights her up; the repetitive marketing tasks do not. Now she's wondering if she has to keep doing work she doesn't enjoy just to hit six figures, or if there's another way. Preston and Clay dig into

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22:03

The Best Marketing Tactic to Get New Clients

Freelance to Founder ·

2026/04/09

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

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21:45

Overcoming the Fear of Networking

Freelance to Founder ·

2026/04/08

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

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23:37

Things Are Getting Messy

Freelance to Founder ·

2026/04/07

Emma Clark runs Clark Content Co. and has spent years managing projects from her inbox and a few spreadsheets—until now. With two contractors on board and plans to hire more, things are getting messy fast. Preston and Christine Olivas break down why defining roles and responsibilities is the real foundation of any good system, and share the surprisingly lean tech stack that keeps Christine's 25-person team running smoothly across complex, fast-moving agency engagements. Support our show sponsors →

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21:46

The Power of Trusting Subcontractors

Freelance to Founder ·

2026/04/03

Omar has built something worth protecting—a roster of loyal clients who hired him as a freelancer and trust him personally. Now he’s growing Vision Craft Studios into a full agency, and the hardest part isn’t finding new clients. It’s handing off the old ones. Preston and Christine Olivas, founder and CEO of No Single Individual, dig into what it really takes to transition client relationships to your team without breaking the trust it took years to build.Support our show sponsors →

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23:52

Is This Cheating?

Freelance to Founder ·

2026/04/02

Layla from Bright Horizon Media has built something real — a small social media marketing agency with two part-time team members and real momentum. Now she's facing the question every growing agency owner hits: how much of your client revenue should you give to your sub-contractors? Is it cheating to charge high and pay low? Preston and Christine Olivas dig into the art of agency pricing, the mindset shift around articulating value, and why who you target matters just as much as what you

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19:36

Drowning? Here's the Fix.

Freelance to Founder ·

2026/04/01

Christine Olivas scaled from solo freelancer to leading a 24-person operation—but the path wasn't as simple as just "hire when you're busy." Preston and Christine dig into one of the most misunderstood decisions in freelancing: when to bring someone on, who to bring on first, and how to avoid trading one grind for another. If you're turning down work and losing sleep, this episode will help you figure out whether you're ready to grow—or just ready to burn out faster.Support our show sponsors →

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14:31

Do Clients Care About 'Expertise'?

Freelance to Founder ·

2026/03/31

CodeCrafter is talented, working hard, and building something real—but a nagging voice keeps whispering that he's not expert enough to charge more, land better clients, or call himself a professional. Preston digs into one of the most common mental traps freelancers fall into: waiting to feel ready before they act. This episode breaks down how to reframe what expertise actually means, why your clients don't need the world's best—they need someone who can solve their specific problem, and how to

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13:14

Subcontracting = Invisible?

Freelance to Founder ·

2026/03/27

Subcontracting can feel like a smart move—until you realize your business is quietly disappearing into someone else's brand. Sound familiar?In this solo episode, Preston digs into a question from Garrett, a 30-year-old nonprofit consultant who's starting to wonder: am I building my business... or just theirs? He's been subcontracting for a seasoned consultant, and the lines between "partnership" and "being swallowed up" are getting blurry fast. Merge, stay, or go solo? Preston walks through how to

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19:00

Big Client, No Team...Do You Say Yes?

Freelance to Founder ·

2026/03/26

Dream client. Huge project. Zero team. Do you say yes and figure it out later—or build the team first and hope they stick around? Preston and Austin break down the classic chicken-and-egg trap every growing freelancer hits... and reveal a third option that could save your reputation, your sanity, and your shot at finally making the leap from solo to agency.Support our show sponsors → https://freelancetofounder.com/sponsorsSubmit your own question → https://freelancetofounder.com/askJoin Austin's

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18:10

Can Non-US Freelancers Actually Get US Clients?

Freelance to Founder ·

2026/03/25

Does your zip code actually matter to American clients? Dieter's freelancing from Europe and wondering if the US market is even worth chasing. The answer might surprise you. Preston and Austin break down why being "foreign" isn't the handicap you think it is — and how to flip your location into a competitive edge that US-based freelancers simply can't match. If geography's been your excuse, this episode pulls the rug right out from under it.Support our show sponsors →

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20:41

Hiring a VA? Here's What Actually Matters

Freelance to Founder ·

2026/03/24

Think you're ready to hire a VA... but have no idea where to start? You're not alone. Every growing freelancer hits that wall — a million tasks, not enough hours, and zero clue who to trust with the work. In this episode, Preston sits down with Austin Church (founder of Freelance Cake Community) to break it all down. Austin brings 4+ years of real VA experience and shares the one thing most freelancers get wrong when hiring — plus his dead-simple framework for knowing exactly what to hand off first

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21:59

Are You Charging Enough to be an Agency?

Freelance to Founder ·

2026/03/23

Still leaving money on the table? Here's the uncomfortable truth: most freelancers underprice themselves—not because they lack skill, but because they're scared of what clients will say.In this episode, Preston and Austin Church dig into the fear of raising rates and what's really holding freelancers back from charging what agencies charge. Austin breaks down the psychology behind client decisions, why replacing you costs them more than you think, and how higher prices can actually make clients

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21:59

When You Just Need More Clients...

Freelance to Founder ·

2026/03/19

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 →

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23:00

Proposals = Waste of Time?

Freelance to Founder ·

2026/03/12

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

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