I'm running low on money and just scrapped an entire episode.

This week I made an executive decision: postpone the Figma episode. We're getting worse, not better. I launched a UX tools bundle at 5am, kept D&D night sacred, and realized I might just be a Dungeon Master LARPing as a founder (still not ready to accept how accurate that is).

This is what it looks like trying to balance play with reality.

CHAPTERS:
00:00 - Executive decision: We're postponing Figma
00:53 - The morning chaos with four teenagers
01:44 - Why we're getting worse, not better
02:42 - "Optimize for chaos, not process"
03:29 - The real cost of on-location shoots
04:56 - Skeleton crew breakdown
05:38 - Overwhelm sets in
06:32 - UX Tools Bundle: Down to the wire
07:03 - 11:30pm and still debugging
07:23 - 5am: Time to hit publish
07:53 - Why D&D night stays sacred
08:13 - "Maybe I'm just a Dungeon Master LARPing as a founder"
09:18 - The Figma multiplayer controversy parallel
10:04 - "If you want to make the wrong decision, ask everyone"

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.

ABOUT STATE OF PLAY
Host Tommy Geoco discovers what fuels the internet's most interesting designers and builders, and shares the messy reality of building in public.

SPECIAL THANKS:
Agustin Eguia: https://agustineguia.com
Adam Stewart: https://www.instagram.com/adnastu/
Tom Fox: https://catalog.tomfox.site/

LINKS:
UX Tools Newsletter: https://uxtools.co
UX Tools Bundle: https://uxtools.co/bundle

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 went from Notion's founding designer to cloning himself with AI at Cursor. This is the full conversation.

From building anime fansites at 11 to architecting Notion's core systems to creating his own OS in a browser - Ryo reveals why the best designers are actually tool makers in disguise.

We dig into creative burnout, why he stopped asking permission, and how AI is turning designers into parallel processors of their own brains.

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 - Building websites at 11 years old
02:00 - The Chinese Apple fanboy community
03:50 - Failed startups and depression
07:00 - Creating "Chinese Stripe" in Shanghai
09:00 - How payment friction created China's internet boom
11:00 - Ivan's daily 4:30pm design critiques at Notion
14:00 - "I was not wrong either" - handling creative friction
17:00 - Becoming a sponge for information
20:00 - The fog of war problem in design
24:00 - "There is one ultimate solution"
27:00 - Why all SaaS tools are the same underneath
30:00 - From Figma to code - killing the abstraction layer
35:00 - Building prototyping environments
38:00 - Why Notion and Cursor solve the same problem
42:00 - What is RyoOS really?
45:00 - "Constant flow state" - rediscovering creative joy
48:00 - Designer burnout and serving too many masters
50:00 - 16-year-olds will out-build senior engineers
52:00 - "We're just builders and makers"

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.

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

LINKS:
UX Tools: 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

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

UX Tools Bundle: $129 for $9k+ in software value. Limited codes, first come first served (details on 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

Ben Huffman built a freelance platform with NO fees. Every investor told him it was the stupidest idea they’d ever heard.
Now Contra has 1M users and a $120M run rate.

We talk about living in the pain cave (the place your ideas live before anyone believes in them), building mission-driven companies, avoiding the “marketplace commodity problem,” and why community-led growth might be the future of creative work.

Get the UX Tools Newsletter (written by me)
Join 90,000+ designers for weekly insights on creative software and the people shaping it: https://uxtools.co

CHAPTERS:
00:00 – The “pain cave” explained
01:12 – Investors called it the “worst idea ever”
04:51 – Why rejection always feels personal
07:32 – Building for the younger version of yourself
10:47 – The humanity problem with commission fees
13:41 – Early internet communities (Themeforest, torrent sites, Newegg)
15:30 – Solving the marketplace commodity problem
18:44 – Going “feed first” to foster authentic connections
20:28 – Becoming an independent discovery engine
24:08 – Partnering with creative tools like Framer
27:26 – Why open networks might win over closed platforms
30:28 – Building leverage as an independent creative
33:53 – The “Hollywood model” for creative projects
37:55 – Resumes are dead, project-based identity is the future
40:39 – Small core teams + specialist networks
43:17 – How indie communities share work and clients
46:05 – Branding yourself to get discovered
48:01 – The story of a 19-year-old making $50K/month from design
50:31 – How Contra makes money without fees
52:21 – Almost out of the pain cave

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

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

NARRATIVE EPISODE:
Spotify: https://open.spotify.com/episode/2CrESEW03tMCrVGMCWlO8d?si=NVpYWxEKSVugGu5okwvh7w
Apple Podcasts: https://podcasts.apple.com/us/podcast/he-built-a-freelance-platform-with-no-fees-now-1m-use-it/id1829478829?i=1000719514305

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