How he built the future for 1M freelancers

How this startup's 30-day death date unlocked a world record

This founder set an expiration ate for his company… and then hit $40M ARR. Eric Simons (the builder behind Bolt.new) turned “we’re shutting down” into the world’s largest hackathon.  In this episode, we break down Eric’s probability playbook and how I’m applying it on my 60‑day clock to keep State of Play alive beyond October 1st.  We talk last bets, 100 swings, hackathons that print customers, and the automations I'm using to help me keep swinging. WHAT YOU'LL LEARN: - How an "end date” forces focus (and why it worked for Eric Simons) - The 100‑swing probability game for finding PMF again - Turning ideas into sales leads (not “projects”) - A real automation stack: Polar → n8n → Notion → email for code fulfillment - Why designers are becoming builders and what that unlocks SUPPORT THE SHOW: UX Tools Newsletter (written by me):  Join 100,000+ designers for weekly insights → https://uxtools.co CHAPTERS 00:00 – “In 60 days, it’s over” (cold open) 00:16 – Meet Eric Simons + the $40M ARR plot twist 00:30 – The decade everyone ignores (failure before the hockey stick) 02:30 – The Dropout DNA (living in an office, working 6am–3am) 03:30 – The $30,000 reality check vs a $300 Bolt build 05:00 – The Probability Playbook: take 100 swings 07:00 – The office‑squatter strategy (desperation, channeled) 09:00 – The competitor’s funeral + picking a death date 11:00 – The builder uprising 11:45 – The million‑dollar tweet (how the hackathon started) 13:00 – Meet the 100,000 (designers → builders) 15:00 – The only title I wear 16:00 – The last swing (countdown to Oct 1, 2025) 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’m rediscovering my love for the game. ABOUT STATE OF PLAY Host Tommy Geoco discovers what fuels the internet’s most interesting designers and builders—real numbers, real stakes, no fluff. LINKS UX Tools Newsletter: https://uxtools.co FOLLOW ME Instagram: https://instagram.com/itsdesignertom X / Twitter: https://x.com/designertom_ LinkedIn: https://linkedin.com/in/tommygeoco TikTok: https://tiktok.com/@designertom Threads: https://threads.net/itsdesignertom

Why this designer cloned himself with Cursor

Ryo Lu built his own operating system. In a browser. For fun. Cursor's Head of Design reveals why he evolved from being a "sponge" (absorbing everyone's input) and started building playgrounds instead.  We talk burnout, creative freedom, and why your weird side project might be the most important thing you build. Get the UX Tools Newsletter (written by me) Join 100,000+ designers for weekly insights on creative software and the people shaping it: https://uxtools.co CHAPTERS: 00:00 - "I've been lying to myself" 00:47 - The Front Page generation 01:16 - Becoming a sponge at Notion 02:23 - Why designers should code (differently) 03:18 - The fog of war metaphor 04:39 - What is RyoOS? 05:17 - From Notion's constraints to Cursor's freedom 07:39 - "It's like constant flow state" 09:39 - Stop asking permission 10:60 - Building in days vs. weeks 12:11 - The 16-year-olds building the future 14:50 - Your playground is already in your head PLAYGROUNDS MENTIONED: Sam Peitz experiments: https://x.com/samdape Lee Black: https://x.com/mrblackstudio Kat the Poet Engineer: https://x.com/poetengineer__ Tatiana Tsiguleva: https://x.com/ciguleva 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/ LINKS: UX Tools Newsletter: https://uxtools.co Follow Ryo: https://x.com/ryolu_ Try Cursor: https://cursor.com See RyoOS: http://os.ryo.lu/ FOLLOW ME: Instagram: https://instagram.com/itsdesignertom X / Twitter: https://x.com/designertom_ LinkedIn: https://linkedin.com/in/tommygeoco TikTok: https://tiktok.com/@designertom Threads: https://threads.net/itsdesignertom AUDIO VERSION: Listen on Spotify: https://open.spotify.com/show/3zDPTGHDSHgBekUxZQxUAN Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/state-of-play/id1829478829

How he built the future for 1M freelancers

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. Get the UX Tools Newsletter 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 [https://studio.youtube.com/channel/UCQKbng8d-nh4EpvOrlF7Idw] - 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