Episodios

  • Pay Gap: Freelancers vs. Agencies

    Pay Gap: Freelancers vs. Agencies
    Apr 17 2026
    Amy Bridges posed a simple question in the Milo Mastermind community and it sparked a conversation Preston and Clay couldn’t let go: does presenting yourself as a freelancer or as an agency actually make a difference in closing clients? The answer turns out to be more nuanced than a simple either/or. In this episode, Preston and Clay dig into the psychology of the sales pitch, why individual trust almost always drives the buying decision, and how the structure you choose—solo or team—should match the kind of client you actually want to work with. Support our show sponsors → ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question → ⁠⁠https://freelancetofounder.com/ask⁠⁠ Check out Clay's business → ⁠⁠⁠⁠https://golinus.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
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    24 m
  • Letting Go of Source Files = Good Idea?

    Letting Go of Source Files = Good Idea?
    Apr 16 2026
    Kevin did a brand redesign for an old colleague two years ago — got paid, and moved on. Now the client's new marketing manager is asking for the original InDesign source files to update the brand guidelines internally. Kevin knows the owner, considers him a friend, and doesn't want to damage the relationship. But he also doesn't want to just hand over his work and forfeit any future opportunities. Preston and Clay dig into who really owns those files, what the law says versus what good business sense says, and how to turn a potentially awkward situation into goodwill — maybe even a Google review. Support our show sponsors → ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question → ⁠⁠https://freelancetofounder.com/ask⁠⁠ Check out Clay's business → ⁠⁠⁠⁠https://golinus.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
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    15 m
  • Love Your Craft, but Tired of Business?

    Love Your Craft, but Tired of Business?
    Apr 15 2026
    Rachel Stone King still loves design and branding—but the business side of freelancing has started to feel like a weight she can't shake. The thought of networking, hunting for clients, and staying motivated has left her feeling overwhelmed and burned out. Preston and Clay dig into what's really going on beneath that feeling, why losing your passion isn't always a crisis, and what practical steps you can take to reconnect with the reason you started in the first place. Support our show sponsors → ⁠⁠https://freelancetofounder.com/sponsors⁠⁠ Submit your own question → ⁠⁠https://freelancetofounder.com/ask⁠⁠ Check out Clay's business → ⁠⁠⁠⁠https://golinus.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices
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    14 m
  • The Power of Saying "No" To Crazy Clients

    The Power of Saying "No" To Crazy Clients
    Apr 14 2026
    Kirstie runs a design business and a client emails her at 5:22 p.m. on a Friday needing an ad designed that same night. Sound familiar? Preston and Clay break down the real question behind rush fees—not just what to charge, but whether you should say yes at all. From setting clear boundaries with clients to knowing when a favor is actually worth it, this episode gives freelancers a practical framework for handling last-minute requests without burning out or building bad expectations. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ Check out Clay's business → ⁠⁠⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices
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    20 m
  • Don't Charge by Hour or Project. Do this...

    Don't Charge by Hour or Project. Do this...
    Apr 13 2026
    Lanya has a freelance project in front of her, she’s estimated the hours, and her client is open to either hourly or project-based pricing—so now what? Preston and Clay make the case that the real question isn’t hourly vs. project-based at all. It’s about understanding the value you bring to the table and pricing accordingly. From the mechanics of asking the right discovery questions to the mindset shift that separates six-figure freelancers from the rest, this episode breaks down the art of value-based pricing in a way that actually makes sense. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ Check out Clay's business → ⁠⁠⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices
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    17 m
  • Remove Pain from Recurring Revenue

    Remove Pain from Recurring Revenue
    Apr 10 2026
    Erica is a web and graphic designer who invested in a coaching program built to turn designers into full-service marketers—complete with monthly retainers, ad campaigns, and recurring revenue. The strategy looked great on paper, but as she started executing it, something felt off. The project work still lights her up; the repetitive marketing tasks do not. Now she's wondering if she has to keep doing work she doesn't enjoy just to hit six figures, or if there's another way. Preston and Clay dig into why following someone else's exact blueprint can quietly lead you away from the work you actually love—and how to build a thriving, recurring-revenue business around just the services that energize you. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ Check out Clay's business → ⁠⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices
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    22 m
  • The Best Marketing Tactic to Get New Clients

    The Best Marketing Tactic to Get New Clients
    Apr 9 2026
    Matt runs Barrow Studio, a brand identity and strategy agency in Bristol, UK—and he's drowning in advice. Every newsletter, YouTube channel, and podcast promises a different "marketing golden ticket": build an email list, go all-in on social media, launch a course, appear on podcasts, host a podcast. The result? He's done none of it, and his agency still runs almost entirely on word-of-mouth referrals. Preston and Clay untangle the overwhelm and lay out a clearer, more honest framework for building a marketing system that actually fits where your business is right now. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ Check out Clay's business → ⁠⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices
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    22 m
  • Overcoming the Fear of Networking

    Overcoming the Fear of Networking
    Apr 8 2026
    Brittany runs her own design studio and knows she needs to get out from behind her screen and start meeting people face-to-face. The problem: she’s shy, and local networking feels downright terrifying. Preston and Clay walk her through exactly how to break into the local business world without pretending to be someone she’s not—from joining a BNI leads group to an unexpectedly genius $100-a-week community stunt that opens doors without a single sales pitch. Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠ Submit your own question → ⁠https://freelancetofounder.com/ask⁠ Check out Clay's business → ⁠https://golinus.com Learn more about your ad choices. Visit megaphone.fm/adchoices
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    22 m