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

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

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
- 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