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State of Play

State of Play

By: Tommy Geoco
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Deep cuts with the internet's most interesting technology creators. Host Tommy Geoco sits down with founders, designers, and tastemakers to uncover the creative DNA connecting everyone building on the internet. Part confessional, part creative archaeology, each episode traces the invisible threads between how we create, why we create, and what the internet's becoming because of it.© 2025 Internet Enjoyers, LLC
Episodes
  • Escaping the design founder's pain cave w/ Ben Huffman
    Jul 28 2025

    Ben Huffman built a company everyone called stupid. Until more than 1M people were using it.

    In this episode of State of Play, the Contra's design founder shares how he went from college dropout to building a new path for creative independence.

    We get real about the pain cave: that brutal, lonely gap between your vision and the world’s doubt, and how to keep going when no one believes in you.

    If you’re building something and feel like no one gets it, this one’s for you.

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    Join 100,000+ designers for weekly insights on creative software and the people shaping it: https://uxtools.co

    CHAPTERS:
    00:00 - Why investors laughed
    02:04 - Getting your first client
    03:03 - Trust issues with platforms
    04:32 - Building with 0% commission
    05:40 - The sting of rejection
    07:36 - Near burnout and losing it all
    08:57 - How Contra makes money
    10:02 - A 20-year-old earns $50k
    12:24 - $50k/month playbook
    13:40 - Why it’s a great time to be creative
    14:25 - The “Hollywood model” shift

    SPECIAL THANKS:
    - Sam Chapman: https://x.com/editedbysam
    - Mapal Berenson: https://www.youtube.com/@mapal
    - Bernabe Bolanos: https://www.youtube.com/@BernabeBolanos
    - Adam Stewart: https://www.instagram.com/adnastu/
    - Tom Fox: https://catalog.tomfox.site/

    ABOUT TOMMY GEOCO
    I spent 15+ years in tech and design. Former military. Father of five. Now building Internet Enjoyers, a weird little media + product studio rediscovering soul in creative tech. This show is how I stay sane and spotlight the outsiders reshaping how we enjoy the internet.

    ABOUT STATE OF PLAY
    A narrative podcast about building things that matter told through deep conversations with designers and builders.

    LINKS
    UX Tools Newsletter: https://uxtools.co
    Follow Ben: https://x.com/_BenHQ
    Check out Contra: https://contra.com

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    16 mins

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