State of Play Transistor (https://transistor.fm) https://feeds.transistor.fm/state-of-play Conversations with designers, founders, and builders behind some of the best work © 2026 Enjoyers Media cb51fb95-3713-53d2-9f70-c383274f070d yes c8f579b0-716d-11f0-b32a-735d275349f0 en Tue, 28 Apr 2026 07:00:13 -0600 Tue, 28 Apr 2026 07:01:26 -0600 https://designertom.substack.com https://img.transistorcdn.com/dNxdbCgBA93Yf5NjtawPHJOdQL6kzyrZuTRs0oFITVY/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9kZTM4/NTdjYjhlYmI5NzU0/YjRlNDNkMjFiNDgy/NTRhNi5qcGc.jpg State of Play https://designertom.substack.com episodic Tommy Geoco Conversations with designers, founders, and builders behind some of the best work Conversations with designers, founders, and builders behind some of the best work. creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business Tommy Geoco tomgeoco@gmail.com No No This is Design At The Most AI-Installed Company: Diego Zaks This is Design At The Most AI-Installed Company: Diego Zaks full 31ce11f8-d6cd-477d-889b-6d39b1bc3d82 https://share.transistor.fm/s/37170f95 Diego Zaks runs design at Ramp, the most AI-installed company in the world. Not kidding, Anthropic showed up at their office because they were using Claude Code more than Anthropic was.

We talk about how Ramp got there, how design changes when everyone is a builder, what AI fluency means inside their company, and what he thinks design becomes five years from here.

Join 100k+ designers reading my newsletter:: https://uxtools.co
Come party with me at Config 2026 (June 25): https://luma.com/usxsrlu1

CHAPTERS:
00:00 The AI-Installed Company
03:50 The Slack Engineer Who Wasn't Human
10:16 The 4 Levels of AI Fluency
13:27 Make Everyone a Designer
22:17 How Ramp Hit 99.5% Installed
28:54 Anthropic Flew to the Office
31:47 Glass: Why Build Your Own AI
49:30 What Design Becomes in 5 Years

LINKS:
Ramp: https://ramp.com
Ramp is hiring: https://ramp.com/careers
Ramp Builders blog (engineering): https://builders.ramp.com
Ramp Labs on X: https://x.com/RampLabs
Diego on X: https://x.com/diegozaks

FOLLOW ME:
X / Twitter: https://x.com/designertom
IG: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Diego Zaks runs design at Ramp, the most AI-installed company in the world. Not kidding, Anthropic showed up at their office because they were using Claude Code more than Anthropic was.

We talk about how Ramp got there, how design changes when everyone is a builder, what AI fluency means inside their company, and what he thinks design becomes five years from here.

Join 100k+ designers reading my newsletter:: https://uxtools.co
Come party with me at Config 2026 (June 25): https://luma.com/usxsrlu1

CHAPTERS:
00:00 The AI-Installed Company
03:50 The Slack Engineer Who Wasn't Human
10:16 The 4 Levels of AI Fluency
13:27 Make Everyone a Designer
22:17 How Ramp Hit 99.5% Installed
28:54 Anthropic Flew to the Office
31:47 Glass: Why Build Your Own AI
49:30 What Design Becomes in 5 Years

LINKS:
Ramp: https://ramp.com
Ramp is hiring: https://ramp.com/careers
Ramp Builders blog (engineering): https://builders.ramp.com
Ramp Labs on X: https://x.com/RampLabs
Diego on X: https://x.com/diegozaks

FOLLOW ME:
X / Twitter: https://x.com/designertom
IG: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Tue, 28 Apr 2026 07:00:00 -0600 Tommy Geoco Tommy Geoco 3710 Diego Zaks runs design at Ramp, the most AI-installed company in the world. Not kidding, Anthropic showed up at their office because they were using Claude Code more than Anthropic was.

We talk about how Ramp got there, how design changes when everyone is a builder, what AI fluency means inside their company, and what he thinks design becomes five years from here.

Join 100k+ designers reading my newsletter:: https://uxtools.co
Come party with me at Config 2026 (June 25): https://luma.com/usxsrlu1

CHAPTERS:
00:00 The AI-Installed Company
03:50 The Slack Engineer Who Wasn't Human
10:16 The 4 Levels of AI Fluency
13:27 Make Everyone a Designer
22:17 How Ramp Hit 99.5% Installed
28:54 Anthropic Flew to the Office
31:47 Glass: Why Build Your Own AI
49:30 What Design Becomes in 5 Years

LINKS:
Ramp: https://ramp.com
Ramp is hiring: https://ramp.com/careers
Ramp Builders blog (engineering): https://builders.ramp.com
Ramp Labs on X: https://x.com/RampLabs
Diego on X: https://x.com/diegozaks

FOLLOW ME:
X / Twitter: https://x.com/designertom
IG: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Amelia Wattenberger: Designing The Next Flow State Amelia Wattenberger: Designing The Next Flow State full 1706a73d-ca23-4134-9353-caf2e462790a https://share.transistor.fm/s/a331168f Amelia Wattenberger spent eight years as a front-end developer before the title on her business card turned into "designer" — she's been at GitHub, now she's building Intent.

This conversation covers why developers are mourning their old flow state, the eras of AI coding tools from Copilot to CLI to the app era, why the spec is becoming the new source of truth, and what Amelia means when she says the work is shifting from implementation to intention.

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:
0:00 — The moment the IDE stopped making sense
2:16 — The ladder of abstraction, and a career moving up and down it
7:35 — Where the abstraction stops: you can't automate eating ice cream
10:29 — Developers are mourning their flow state
16:02 — Eras of AI coding tools: Copilot → CLI → the app
22:43 — Living specs vs. static PRDs
29:38 — Inside Intent: workspaces as desks you pick up and put down
39:02 — Plan, implement, review — and where the medium goes next
42:46 — Advice for people too employed to pathfind
44:33 — Outro: where purpose lives when agents do the rest

LINKS:
Intent: https://www.augmentcode.com/product/intent
Amelia Wattenberger on X: https://x.com/Wattenberger
Amelia's Musings: https://wattenberger.com/

FOLLOW ME:
X / Twitter: https://x.com/designertom
IG: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Amelia Wattenberger spent eight years as a front-end developer before the title on her business card turned into "designer" — she's been at GitHub, now she's building Intent.

This conversation covers why developers are mourning their old flow state, the eras of AI coding tools from Copilot to CLI to the app era, why the spec is becoming the new source of truth, and what Amelia means when she says the work is shifting from implementation to intention.

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:
0:00 — The moment the IDE stopped making sense
2:16 — The ladder of abstraction, and a career moving up and down it
7:35 — Where the abstraction stops: you can't automate eating ice cream
10:29 — Developers are mourning their flow state
16:02 — Eras of AI coding tools: Copilot → CLI → the app
22:43 — Living specs vs. static PRDs
29:38 — Inside Intent: workspaces as desks you pick up and put down
39:02 — Plan, implement, review — and where the medium goes next
42:46 — Advice for people too employed to pathfind
44:33 — Outro: where purpose lives when agents do the rest

LINKS:
Intent: https://www.augmentcode.com/product/intent
Amelia Wattenberger on X: https://x.com/Wattenberger
Amelia's Musings: https://wattenberger.com/

FOLLOW ME:
X / Twitter: https://x.com/designertom
IG: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 20 Apr 2026 09:47:10 -0600 Tommy Geoco Tommy Geoco 2733 Amelia Wattenberger spent eight years as a front-end developer before the title on her business card turned into "designer" — she's been at GitHub, now she's building Intent.

This conversation covers why developers are mourning their old flow state, the eras of AI coding tools from Copilot to CLI to the app era, why the spec is becoming the new source of truth, and what Amelia means when she says the work is shifting from implementation to intention.

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:
0:00 — The moment the IDE stopped making sense
2:16 — The ladder of abstraction, and a career moving up and down it
7:35 — Where the abstraction stops: you can't automate eating ice cream
10:29 — Developers are mourning their flow state
16:02 — Eras of AI coding tools: Copilot → CLI → the app
22:43 — Living specs vs. static PRDs
29:38 — Inside Intent: workspaces as desks you pick up and put down
39:02 — Plan, implement, review — and where the medium goes next
42:46 — Advice for people too employed to pathfind
44:33 — Outro: where purpose lives when agents do the rest

LINKS:
Intent: https://www.augmentcode.com/product/intent
Amelia Wattenberger on X: https://x.com/Wattenberger
Amelia's Musings: https://wattenberger.com/

FOLLOW ME:
X / Twitter: https://x.com/designertom
IG: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Nad Chishtie: Lovable's Design System For Agents Nad Chishtie: Lovable's Design System For Agents full 2fe8ef34-60da-48d3-9c0b-fd444966e13a https://share.transistor.fm/s/cd682833 Nad Chishtie is the Head of Design at Lovable — the company at the center of the AI coding explosion. He nearly got fired before his first day for emailing his CEO a thesis on why Lovable should be a web browser.

Now he's redesigning what design teams look like when everyone in the company can build software. 

We talked about why half of Lovable's design system is now written for agents instead of people, what happened when they went full "agent maxing" for two weeks (and why background agents failed), and there's this moment where he explains who actually ends up owning vibe coding when it lands inside a big company — and it's not who you'd expect.

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:
0:00 — Almost fired before day one
1:20 — Falling into design by accident
2:39 — The call that changed his career
4:45 — Why generalists felt broken in traditional orgs
5:08 — The "gumption" trait for AI-native work
6:54 — Housekeeping vs cannibalizing yourself
8:23 — End-to-end ownership when everyone can build
10:54 — Spiking fast and killing darlings faster
13:06 — People who couldn't prototype before now can
15:05 — How Lovable's org actually works
19:44 — When enterprise came knocking
22:45 — Hackathons and making room for throwaway work
25:15 — The email that almost got him fired (full story)
28:09 — Apple blocking mobile vibe coding apps
30:27 — Half our design system is written for agents
31:34 — Agent maxing: background agents failed, linters won
33:53 — Eating their own SaaS stack
37:15 — Who actually owns vibe coding in the enterprise
42:43 — What Lovable looks for when hiring designers
43:28 — Why every designer should be a founder right now
46:54 — Territory Studio uses Lovable for sci-fi UIs
48:16 — Thesis: everything will be interoperable

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.

LINKS:
Lovable: https://lovable.dev
Follow Nad: https://x.com/nadonomy

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Nad Chishtie is the Head of Design at Lovable — the company at the center of the AI coding explosion. He nearly got fired before his first day for emailing his CEO a thesis on why Lovable should be a web browser.

Now he's redesigning what design teams look like when everyone in the company can build software. 

We talked about why half of Lovable's design system is now written for agents instead of people, what happened when they went full "agent maxing" for two weeks (and why background agents failed), and there's this moment where he explains who actually ends up owning vibe coding when it lands inside a big company — and it's not who you'd expect.

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:
0:00 — Almost fired before day one
1:20 — Falling into design by accident
2:39 — The call that changed his career
4:45 — Why generalists felt broken in traditional orgs
5:08 — The "gumption" trait for AI-native work
6:54 — Housekeeping vs cannibalizing yourself
8:23 — End-to-end ownership when everyone can build
10:54 — Spiking fast and killing darlings faster
13:06 — People who couldn't prototype before now can
15:05 — How Lovable's org actually works
19:44 — When enterprise came knocking
22:45 — Hackathons and making room for throwaway work
25:15 — The email that almost got him fired (full story)
28:09 — Apple blocking mobile vibe coding apps
30:27 — Half our design system is written for agents
31:34 — Agent maxing: background agents failed, linters won
33:53 — Eating their own SaaS stack
37:15 — Who actually owns vibe coding in the enterprise
42:43 — What Lovable looks for when hiring designers
43:28 — Why every designer should be a founder right now
46:54 — Territory Studio uses Lovable for sci-fi UIs
48:16 — Thesis: everything will be interoperable

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.

LINKS:
Lovable: https://lovable.dev
Follow Nad: https://x.com/nadonomy

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Wed, 15 Apr 2026 10:25:02 -0600 Tommy Geoco Tommy Geoco 3017 Nad Chishtie is the Head of Design at Lovable — the company at the center of the AI coding explosion. He nearly got fired before his first day for emailing his CEO a thesis on why Lovable should be a web browser.

Now he's redesigning what design teams look like when everyone in the company can build software. 

We talked about why half of Lovable's design system is now written for agents instead of people, what happened when they went full "agent maxing" for two weeks (and why background agents failed), and there's this moment where he explains who actually ends up owning vibe coding when it lands inside a big company — and it's not who you'd expect.

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:
0:00 — Almost fired before day one
1:20 — Falling into design by accident
2:39 — The call that changed his career
4:45 — Why generalists felt broken in traditional orgs
5:08 — The "gumption" trait for AI-native work
6:54 — Housekeeping vs cannibalizing yourself
8:23 — End-to-end ownership when everyone can build
10:54 — Spiking fast and killing darlings faster
13:06 — People who couldn't prototype before now can
15:05 — How Lovable's org actually works
19:44 — When enterprise came knocking
22:45 — Hackathons and making room for throwaway work
25:15 — The email that almost got him fired (full story)
28:09 — Apple blocking mobile vibe coding apps
30:27 — Half our design system is written for agents
31:34 — Agent maxing: background agents failed, linters won
33:53 — Eating their own SaaS stack
37:15 — Who actually owns vibe coding in the enterprise
42:43 — What Lovable looks for when hiring designers
43:28 — Why every designer should be a founder right now
46:54 — Territory Studio uses Lovable for sci-fi UIs
48:16 — Thesis: everything will be interoperable

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.

LINKS:
Lovable: https://lovable.dev
Follow Nad: https://x.com/nadonomy

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Basement Studio: They Used Wine to Build a Website. Here's How. Basement Studio: They Used Wine to Build a Website. Here's How. full 49b35e2d-529e-4967-8ecf-288921f9eb9e https://share.transistor.fm/s/dac65647 Facundo Santana and José Rago run Basement Studio - 35 people in Argentina, working with Vercel, Mr. Beast, and Kid Super. 

They poured actual wine on a surface to get a WebGL texture right. That detail tells you everything about how this shop operates.

This conversation covers how they protect quality as they scale, the R&D lab that spun out BasHub and XMP, why they open-source everything, how 30 people pile into a single Slack channel before anything ships, and why Basement Ventures is quietly becoming a real VC fund.

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:
0:00 — They used actual wine to build a website
0:24 — Who is Basement Studio?
1:36 — From a Buenos Aires apartment to 35 people
5:17 — The Kid Super World project
7:19 — "Would you show it to your mom?"
9:49 — Working with Vercel on Geist and v0
13:20 — How 30 people review work in one Slack channel
16:05 — Open source: BasHub, XMP, and giving back
18:06 — The lab that becomes real products
21:32 — How AI is changing creative studios
24:49 — Basement Ventures: from studio to microfund
28:43 — Investing in the tools you actually use
31:14 — Building a studio that outlasts its founders

LINKS:
Basement Studio: https://basement.studio
Facundo on X: https://x.com/falanfantana
José on X: https://x.com/ragojose

Watch on YouTube: https://youtu.be/nv7M79lMEnU

FOLLOW ME:
Newsletter: https://uxtools.co
X / Twitter: https://x.com/tommygeoco
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Facundo Santana and José Rago run Basement Studio - 35 people in Argentina, working with Vercel, Mr. Beast, and Kid Super. 

They poured actual wine on a surface to get a WebGL texture right. That detail tells you everything about how this shop operates.

This conversation covers how they protect quality as they scale, the R&D lab that spun out BasHub and XMP, why they open-source everything, how 30 people pile into a single Slack channel before anything ships, and why Basement Ventures is quietly becoming a real VC fund.

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:
0:00 — They used actual wine to build a website
0:24 — Who is Basement Studio?
1:36 — From a Buenos Aires apartment to 35 people
5:17 — The Kid Super World project
7:19 — "Would you show it to your mom?"
9:49 — Working with Vercel on Geist and v0
13:20 — How 30 people review work in one Slack channel
16:05 — Open source: BasHub, XMP, and giving back
18:06 — The lab that becomes real products
21:32 — How AI is changing creative studios
24:49 — Basement Ventures: from studio to microfund
28:43 — Investing in the tools you actually use
31:14 — Building a studio that outlasts its founders

LINKS:
Basement Studio: https://basement.studio
Facundo on X: https://x.com/falanfantana
José on X: https://x.com/ragojose

Watch on YouTube: https://youtu.be/nv7M79lMEnU

FOLLOW ME:
Newsletter: https://uxtools.co
X / Twitter: https://x.com/tommygeoco
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Wed, 08 Apr 2026 07:00:00 -0600 Tommy Geoco Tommy Geoco 2077 Facundo Santana and José Rago run Basement Studio - 35 people in Argentina, working with Vercel, Mr. Beast, and Kid Super. 

They poured actual wine on a surface to get a WebGL texture right. That detail tells you everything about how this shop operates.

This conversation covers how they protect quality as they scale, the R&D lab that spun out BasHub and XMP, why they open-source everything, how 30 people pile into a single Slack channel before anything ships, and why Basement Ventures is quietly becoming a real VC fund.

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:
0:00 — They used actual wine to build a website
0:24 — Who is Basement Studio?
1:36 — From a Buenos Aires apartment to 35 people
5:17 — The Kid Super World project
7:19 — "Would you show it to your mom?"
9:49 — Working with Vercel on Geist and v0
13:20 — How 30 people review work in one Slack channel
16:05 — Open source: BasHub, XMP, and giving back
18:06 — The lab that becomes real products
21:32 — How AI is changing creative studios
24:49 — Basement Ventures: from studio to microfund
28:43 — Investing in the tools you actually use
31:14 — Building a studio that outlasts its founders

LINKS:
Basement Studio: https://basement.studio
Facundo on X: https://x.com/falanfantana
José on X: https://x.com/ragojose

Watch on YouTube: https://youtu.be/nv7M79lMEnU

FOLLOW ME:
Newsletter: https://uxtools.co
X / Twitter: https://x.com/tommygeoco
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Ben Blumenrose: He Sees How 50+ Design Teams Use AI. Most Are Doing It Wrong. Ben Blumenrose: He Sees How 50+ Design Teams Use AI. Most Are Doing It Wrong. full 5bcd18a7-6a08-4db1-bbb0-9ed67559cd8b https://share.transistor.fm/s/2d51d2a7 Ben Blumenrose runs Designer Fund, which means he doesn't just see one team figure out AI, he sees how 50+ design teams across the portfolio are absorbing it. 

This conversation covers what happens when the floor rises, what AI fluency actually looks like inside companies, why the AI ops role is emerging earlier than anyone expected, and how Ben is thinking about keeping his own kids away from the tools — for now.

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:
1:05 — Process flexibility and conflicting signals
2:27 — What Designer Fund's portfolio is actually doing with AI
5:34 — Enterprise adoption: Carvana vs eBay
6:40 — The AI ops role emerging at hire #4
9:59 — AI Imagineer and redesigning how designers work
12:12 — Junior designers vs early career talent
16:09 — AI native vs AI fluency
21:05 — The 19% slower problem and the factory floor
22:12 — The T-shaped designer gets wider and deeper
25:21 — Evaluating AI fluency in hiring
28:25 — Where the tools are now vs nine months ago
30:06 — The floor is high but the ceiling still matters
31:29 — Moral panic and the value of exceptional designers
33:27 — Does the designer-founder thesis still hold?
35:28 — VC path in a world where one person = a team
37:13 — Phantom competency: extraordinary person or extraordinary tools?
40:24 — Keeping kids away from AI and the Tin Can phone
45:14 — Closing: the bar is moving sideways

LINKS:
Designer Fund: https://designerfund.com
Ben Blumenrose on X: https://x.com/benblumenrose

FOLLOW ME:
Newsletter: https://uxtools.co
X / Twitter: https://x.com/tommygeoco
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Ben Blumenrose runs Designer Fund, which means he doesn't just see one team figure out AI, he sees how 50+ design teams across the portfolio are absorbing it. 

This conversation covers what happens when the floor rises, what AI fluency actually looks like inside companies, why the AI ops role is emerging earlier than anyone expected, and how Ben is thinking about keeping his own kids away from the tools — for now.

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:
1:05 — Process flexibility and conflicting signals
2:27 — What Designer Fund's portfolio is actually doing with AI
5:34 — Enterprise adoption: Carvana vs eBay
6:40 — The AI ops role emerging at hire #4
9:59 — AI Imagineer and redesigning how designers work
12:12 — Junior designers vs early career talent
16:09 — AI native vs AI fluency
21:05 — The 19% slower problem and the factory floor
22:12 — The T-shaped designer gets wider and deeper
25:21 — Evaluating AI fluency in hiring
28:25 — Where the tools are now vs nine months ago
30:06 — The floor is high but the ceiling still matters
31:29 — Moral panic and the value of exceptional designers
33:27 — Does the designer-founder thesis still hold?
35:28 — VC path in a world where one person = a team
37:13 — Phantom competency: extraordinary person or extraordinary tools?
40:24 — Keeping kids away from AI and the Tin Can phone
45:14 — Closing: the bar is moving sideways

LINKS:
Designer Fund: https://designerfund.com
Ben Blumenrose on X: https://x.com/benblumenrose

FOLLOW ME:
Newsletter: https://uxtools.co
X / Twitter: https://x.com/tommygeoco
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Sat, 04 Apr 2026 07:00:00 -0600 Tommy Geoco Tommy Geoco 2754 Ben Blumenrose runs Designer Fund, which means he doesn't just see one team figure out AI, he sees how 50+ design teams across the portfolio are absorbing it. 

This conversation covers what happens when the floor rises, what AI fluency actually looks like inside companies, why the AI ops role is emerging earlier than anyone expected, and how Ben is thinking about keeping his own kids away from the tools — for now.

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:
1:05 — Process flexibility and conflicting signals
2:27 — What Designer Fund's portfolio is actually doing with AI
5:34 — Enterprise adoption: Carvana vs eBay
6:40 — The AI ops role emerging at hire #4
9:59 — AI Imagineer and redesigning how designers work
12:12 — Junior designers vs early career talent
16:09 — AI native vs AI fluency
21:05 — The 19% slower problem and the factory floor
22:12 — The T-shaped designer gets wider and deeper
25:21 — Evaluating AI fluency in hiring
28:25 — Where the tools are now vs nine months ago
30:06 — The floor is high but the ceiling still matters
31:29 — Moral panic and the value of exceptional designers
33:27 — Does the designer-founder thesis still hold?
35:28 — VC path in a world where one person = a team
37:13 — Phantom competency: extraordinary person or extraordinary tools?
40:24 — Keeping kids away from AI and the Tin Can phone
45:14 — Closing: the bar is moving sideways

LINKS:
Designer Fund: https://designerfund.com
Ben Blumenrose on X: https://x.com/benblumenrose

FOLLOW ME:
Newsletter: https://uxtools.co
X / Twitter: https://x.com/tommygeoco
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Josh Puckett: Design Has Never Been More in Demand. So Why Can't Juniors Get Hired? Josh Puckett: Design Has Never Been More in Demand. So Why Can't Juniors Get Hired? full 1fe94ad7-492c-4da1-9e20-d1b9f0609197 https://share.transistor.fm/s/07c26101 Josh Puckett went goblin mode for four weeks to ship Interface Craft — a course where you pick a library card, sign your name on it, and insert it into a web interface that unlocks everything behind it.

He's been designing for close to 20 years. Dropbox. Wealthfront. He's mentored and placed hundreds of designers through Upper Study. He invests into early-stage tools companies through Combine VC.

We talk phantom competency, uncommon care, why a chef who cooks one new dish a week should probably find a different career, and whether "AI native" is a real skill or just the new "mobile designer."

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 - "You have to demonstrate high slope"
00:14 - Who is Josh Puckett
01:53 - Coming out of the Interface Craft launch
04:03 - Goblin mode & going dark to build
04:45 - The Wealthfront chapter: 4-person design team
05:49 - Has design actually changed?
08:22 - Phantom competency & AI as apprenticeship
09:34 - LLMs as tutors: where they help, where they miss
11:20 - What are you telling designers right now?
12:32 - Uncommon effort vs. uncommon taste
16:19 - Discovery has changed: social as a portfolio
19:18 - "AI native" is just the new "mobile designer"
21:50 - High slope: what it looks like
24:10 - The playground pattern
25:47 - What to do with the anxiety
29:31 - Uncommon care: just give a shit
31:44 - Shot selection: where to invest your time
35:31 - What multi-perspective gives you
37:30 - Product design is not art
38:42 - Why designers are the least happy with AI
39:52 - One post away from changing your life

ABOUT STATE OF PLAY
Host Tommy Geoco discovers what fuels the internet's most interesting designers and builders.

LINKS:
Interface Craft: https://interfacecraft.dev/
Upper Study: https://upperstudy.com
Follow Josh: https://x.com/joshpuckett

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Josh Puckett went goblin mode for four weeks to ship Interface Craft — a course where you pick a library card, sign your name on it, and insert it into a web interface that unlocks everything behind it.

He's been designing for close to 20 years. Dropbox. Wealthfront. He's mentored and placed hundreds of designers through Upper Study. He invests into early-stage tools companies through Combine VC.

We talk phantom competency, uncommon care, why a chef who cooks one new dish a week should probably find a different career, and whether "AI native" is a real skill or just the new "mobile designer."

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 - "You have to demonstrate high slope"
00:14 - Who is Josh Puckett
01:53 - Coming out of the Interface Craft launch
04:03 - Goblin mode & going dark to build
04:45 - The Wealthfront chapter: 4-person design team
05:49 - Has design actually changed?
08:22 - Phantom competency & AI as apprenticeship
09:34 - LLMs as tutors: where they help, where they miss
11:20 - What are you telling designers right now?
12:32 - Uncommon effort vs. uncommon taste
16:19 - Discovery has changed: social as a portfolio
19:18 - "AI native" is just the new "mobile designer"
21:50 - High slope: what it looks like
24:10 - The playground pattern
25:47 - What to do with the anxiety
29:31 - Uncommon care: just give a shit
31:44 - Shot selection: where to invest your time
35:31 - What multi-perspective gives you
37:30 - Product design is not art
38:42 - Why designers are the least happy with AI
39:52 - One post away from changing your life

ABOUT STATE OF PLAY
Host Tommy Geoco discovers what fuels the internet's most interesting designers and builders.

LINKS:
Interface Craft: https://interfacecraft.dev/
Upper Study: https://upperstudy.com
Follow Josh: https://x.com/joshpuckett

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 30 Mar 2026 07:00:00 -0600 Tommy Geoco Tommy Geoco 2435 Josh Puckett went goblin mode for four weeks to ship Interface Craft — a course where you pick a library card, sign your name on it, and insert it into a web interface that unlocks everything behind it.

He's been designing for close to 20 years. Dropbox. Wealthfront. He's mentored and placed hundreds of designers through Upper Study. He invests into early-stage tools companies through Combine VC.

We talk phantom competency, uncommon care, why a chef who cooks one new dish a week should probably find a different career, and whether "AI native" is a real skill or just the new "mobile designer."

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 - "You have to demonstrate high slope"
00:14 - Who is Josh Puckett
01:53 - Coming out of the Interface Craft launch
04:03 - Goblin mode & going dark to build
04:45 - The Wealthfront chapter: 4-person design team
05:49 - Has design actually changed?
08:22 - Phantom competency & AI as apprenticeship
09:34 - LLMs as tutors: where they help, where they miss
11:20 - What are you telling designers right now?
12:32 - Uncommon effort vs. uncommon taste
16:19 - Discovery has changed: social as a portfolio
19:18 - "AI native" is just the new "mobile designer"
21:50 - High slope: what it looks like
24:10 - The playground pattern
25:47 - What to do with the anxiety
29:31 - Uncommon care: just give a shit
31:44 - Shot selection: where to invest your time
35:31 - What multi-perspective gives you
37:30 - Product design is not art
38:42 - Why designers are the least happy with AI
39:52 - One post away from changing your life

ABOUT STATE OF PLAY
Host Tommy Geoco discovers what fuels the internet's most interesting designers and builders.

LINKS:
Interface Craft: https://interfacecraft.dev/
Upper Study: https://upperstudy.com
Follow Josh: https://x.com/joshpuckett

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Jenny Wen: She Went From FigJam to Anthropic. This Is the New Era of UX. Jenny Wen: She Went From FigJam to Anthropic. This Is the New Era of UX. full d20d66b6-8b86-46bc-ad56-8bea0f6b66ec https://share.transistor.fm/s/364d490a Jenny Wen led design on FigJam, one of the most playful tools to hit design in a decade. Now she's at Anthropic designing Claude. Not just the model, but the product that millions use daily. 

What I didn't expect: she sees these as the same problem. Both hide serious technical complexity behind simple, obvious interfaces. 

We talked about why designers are shipping production code now, why "UX designer" as a role feels outdated, and this framework she keeps coming back to: automate toil, augment creativity.

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 - From FigJam to Claude: same design problem, higher stakes
04:52 - How much model complexity should users actually see?
09:05 - Prototypes over docs in AI product development
16:04 - Why long-term design vision is harder in AI labs
21:27 - The canvas-tool category Jenny is watching
26:30 - Is chat UI over? (Jenny says no)
33:40 - From print magazine dreams to product design
42:03 - Will I ever recreate that FigJam magic?
47:51 - Is "UX designer" becoming outdated?
49:22 - Taste vs execution: the distinction more designers need

LINKS:
Claude: https://claude.ai
Jenny Wen: https://x.com/jenny_wen

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Jenny Wen led design on FigJam, one of the most playful tools to hit design in a decade. Now she's at Anthropic designing Claude. Not just the model, but the product that millions use daily. 

What I didn't expect: she sees these as the same problem. Both hide serious technical complexity behind simple, obvious interfaces. 

We talked about why designers are shipping production code now, why "UX designer" as a role feels outdated, and this framework she keeps coming back to: automate toil, augment creativity.

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 - From FigJam to Claude: same design problem, higher stakes
04:52 - How much model complexity should users actually see?
09:05 - Prototypes over docs in AI product development
16:04 - Why long-term design vision is harder in AI labs
21:27 - The canvas-tool category Jenny is watching
26:30 - Is chat UI over? (Jenny says no)
33:40 - From print magazine dreams to product design
42:03 - Will I ever recreate that FigJam magic?
47:51 - Is "UX designer" becoming outdated?
49:22 - Taste vs execution: the distinction more designers need

LINKS:
Claude: https://claude.ai
Jenny Wen: https://x.com/jenny_wen

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Tue, 24 Mar 2026 07:00:00 -0600 Tommy Geoco Tommy Geoco 3054 Jenny Wen led design on FigJam, one of the most playful tools to hit design in a decade. Now she's at Anthropic designing Claude. Not just the model, but the product that millions use daily. 

What I didn't expect: she sees these as the same problem. Both hide serious technical complexity behind simple, obvious interfaces. 

We talked about why designers are shipping production code now, why "UX designer" as a role feels outdated, and this framework she keeps coming back to: automate toil, augment creativity.

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 - From FigJam to Claude: same design problem, higher stakes
04:52 - How much model complexity should users actually see?
09:05 - Prototypes over docs in AI product development
16:04 - Why long-term design vision is harder in AI labs
21:27 - The canvas-tool category Jenny is watching
26:30 - Is chat UI over? (Jenny says no)
33:40 - From print magazine dreams to product design
42:03 - Will I ever recreate that FigJam magic?
47:51 - Is "UX designer" becoming outdated?
49:22 - Taste vs execution: the distinction more designers need

LINKS:
Claude: https://claude.ai
Jenny Wen: https://x.com/jenny_wen

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Steve Ruiz: He Turned Down Adobe. Then He Shelved His Own Product. Steve Ruiz: He Turned Down Adobe. Then He Shelved His Own Product. full cd953352-bd5b-4818-9f1a-9b5699794052 https://share.transistor.fm/s/58cbb5ff Steve Ruiz was about to start at Adobe. Bags packed. Job accepted. Start date: Monday.

Then he looked at what was happening with his side project — an open-source canvas tool he'd been building — and 200,000 people were using it every month. Hundreds of sponsors had put up 00,000. Two major companies wanted to build on it. He called Adobe and said he wasn't coming.

That project became TLDraw.

Steve's background isn't in software — it's in fine art. He has a masters in it. He spent thousands of hours studying ink on paper — how it moves, how it bleeds, how it dries. And when he later wrote the algorithms for digital ink, he had this deep physical knowledge that most engineers just don't have.

We talk about why he killed his own SaaS product to focus on the SDK, why he thinks craft only matters when you're building for high-agency users, and his surprisingly simple answer to the question every open-source founder faces — how do you actually make money?

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 - Cold open
01:30 - Art school to open source
04:32 - 10,000 hours of unmotivated work
06:08 - Finding ideas without external validation
08:22 - The content-first experimentation loop
11:30 - Why software is easier than art
14:42 - Most software experiences haven't been discovered yet
17:10 - Prototyping obsession and the infinite canvas
17:47 - 200,000 users before you could even log in
19:14 - Make Real: the first vibe code tool
21:13 - Optimize for the points of contact
23:51 - Killing the SaaS to ship the SDK
29:19 - The open source money problem
30:03 - "Just charge for it" — beating React Flow
32:12 - When craft actually matters (high-agency users)
35:57 - What's most fulfilling about building TLDraw

ABOUT TOMMY GEOCO
I spent 15+ years in tech and design. Former military. Father of five. Now building a weird little media + product studio rediscovering soul in creative tech.

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
TLDraw: https://tldraw.com
Follow Steve: https://x.com/steveruizok

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Steve Ruiz was about to start at Adobe. Bags packed. Job accepted. Start date: Monday.

Then he looked at what was happening with his side project — an open-source canvas tool he'd been building — and 200,000 people were using it every month. Hundreds of sponsors had put up 00,000. Two major companies wanted to build on it. He called Adobe and said he wasn't coming.

That project became TLDraw.

Steve's background isn't in software — it's in fine art. He has a masters in it. He spent thousands of hours studying ink on paper — how it moves, how it bleeds, how it dries. And when he later wrote the algorithms for digital ink, he had this deep physical knowledge that most engineers just don't have.

We talk about why he killed his own SaaS product to focus on the SDK, why he thinks craft only matters when you're building for high-agency users, and his surprisingly simple answer to the question every open-source founder faces — how do you actually make money?

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 - Cold open
01:30 - Art school to open source
04:32 - 10,000 hours of unmotivated work
06:08 - Finding ideas without external validation
08:22 - The content-first experimentation loop
11:30 - Why software is easier than art
14:42 - Most software experiences haven't been discovered yet
17:10 - Prototyping obsession and the infinite canvas
17:47 - 200,000 users before you could even log in
19:14 - Make Real: the first vibe code tool
21:13 - Optimize for the points of contact
23:51 - Killing the SaaS to ship the SDK
29:19 - The open source money problem
30:03 - "Just charge for it" — beating React Flow
32:12 - When craft actually matters (high-agency users)
35:57 - What's most fulfilling about building TLDraw

ABOUT TOMMY GEOCO
I spent 15+ years in tech and design. Former military. Father of five. Now building a weird little media + product studio rediscovering soul in creative tech.

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
TLDraw: https://tldraw.com
Follow Steve: https://x.com/steveruizok

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 16 Mar 2026 07:00:00 -0600 Tommy Geoco Tommy Geoco 2323 Steve Ruiz was about to start at Adobe. Bags packed. Job accepted. Start date: Monday.

Then he looked at what was happening with his side project — an open-source canvas tool he'd been building — and 200,000 people were using it every month. Hundreds of sponsors had put up 00,000. Two major companies wanted to build on it. He called Adobe and said he wasn't coming.

That project became TLDraw.

Steve's background isn't in software — it's in fine art. He has a masters in it. He spent thousands of hours studying ink on paper — how it moves, how it bleeds, how it dries. And when he later wrote the algorithms for digital ink, he had this deep physical knowledge that most engineers just don't have.

We talk about why he killed his own SaaS product to focus on the SDK, why he thinks craft only matters when you're building for high-agency users, and his surprisingly simple answer to the question every open-source founder faces — how do you actually make money?

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 - Cold open
01:30 - Art school to open source
04:32 - 10,000 hours of unmotivated work
06:08 - Finding ideas without external validation
08:22 - The content-first experimentation loop
11:30 - Why software is easier than art
14:42 - Most software experiences haven't been discovered yet
17:10 - Prototyping obsession and the infinite canvas
17:47 - 200,000 users before you could even log in
19:14 - Make Real: the first vibe code tool
21:13 - Optimize for the points of contact
23:51 - Killing the SaaS to ship the SDK
29:19 - The open source money problem
30:03 - "Just charge for it" — beating React Flow
32:12 - When craft actually matters (high-agency users)
35:57 - What's most fulfilling about building TLDraw

ABOUT TOMMY GEOCO
I spent 15+ years in tech and design. Former military. Father of five. Now building a weird little media + product studio rediscovering soul in creative tech.

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
TLDraw: https://tldraw.com
Follow Steve: https://x.com/steveruizok

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Ben Fryc: He Quit Freelancing After Doubling His Salary. Ben Fryc: He Quit Freelancing After Doubling His Salary. full 9ea5cc2f-6191-4bc4-b5a9-ce0d42cd3de7 https://share.transistor.fm/s/b4a5ccbb Ben Fryc doubled his freelance salary in a year. Then his wife told him, on vacation in San Francisco, that he was working too hard. 

He quit freelancing and never went back.

Ben taught himself Cinema 4D during COVID and started designing a physical keyboard in Figma. Now he's a household name in motion design, works at Framer, and takes on all manner of passion projects.

We get into the experimentation crash loop of learning 3D tools, why he treats passion projects like hobbies, and what he tells the young creative who wants to do it all.

Get our newsletter: https://uxtools.co

CHAPTERS
00:00 — Intro
01:45 — Comic books, GeoCities, and why Ben wanted to make video games
04:40 — Five years at Mango Languages and the 3D pivot during COVID
07:20 — "You don't need to know everything about a tool"
09:26 — The Polygon Runway course and finding your people
12:51 — The Knob: fantastical devices that probably can't exist
15:33 — Commerce vs. passion and treating creativity like a hobby
17:59 — Photoshop muscle memory and tools that refuse to die
19:47 — Storyboarding as the bridge between static and motion
21:36 — What motion tools still hide behind right-clicks
24:28 — From Figma mockups to firmware in C
29:45 — Moments of delight: what makes motion design captivating
34:20 — The Play-Doh people nobody liked
35:25 — Where AI actually helps creative work
37:32 — Advice for the young creative who wants to do it all
40:38 — "I doubled my salary freelancing. Then my wife said stop."
43:53 — Outro

LINKS
Ben Fryc — https://x.com/benfryc
Framer — https://framer.com

FOLLOW ME
Twitter/X — https://x.com/designertom
LinkedIn — https://linkedin.com/in/tommygeoco
Newsletter — https://uxtools.co

]]> Ben Fryc doubled his freelance salary in a year. Then his wife told him, on vacation in San Francisco, that he was working too hard. 

He quit freelancing and never went back.

Ben taught himself Cinema 4D during COVID and started designing a physical keyboard in Figma. Now he's a household name in motion design, works at Framer, and takes on all manner of passion projects.

We get into the experimentation crash loop of learning 3D tools, why he treats passion projects like hobbies, and what he tells the young creative who wants to do it all.

Get our newsletter: https://uxtools.co

CHAPTERS
00:00 — Intro
01:45 — Comic books, GeoCities, and why Ben wanted to make video games
04:40 — Five years at Mango Languages and the 3D pivot during COVID
07:20 — "You don't need to know everything about a tool"
09:26 — The Polygon Runway course and finding your people
12:51 — The Knob: fantastical devices that probably can't exist
15:33 — Commerce vs. passion and treating creativity like a hobby
17:59 — Photoshop muscle memory and tools that refuse to die
19:47 — Storyboarding as the bridge between static and motion
21:36 — What motion tools still hide behind right-clicks
24:28 — From Figma mockups to firmware in C
29:45 — Moments of delight: what makes motion design captivating
34:20 — The Play-Doh people nobody liked
35:25 — Where AI actually helps creative work
37:32 — Advice for the young creative who wants to do it all
40:38 — "I doubled my salary freelancing. Then my wife said stop."
43:53 — Outro

LINKS
Ben Fryc — https://x.com/benfryc
Framer — https://framer.com

FOLLOW ME
Twitter/X — https://x.com/designertom
LinkedIn — https://linkedin.com/in/tommygeoco
Newsletter — https://uxtools.co

]]> Mon, 09 Mar 2026 07:00:00 -0600 Tommy Geoco Tommy Geoco 2690 Ben Fryc doubled his freelance salary in a year. Then his wife told him, on vacation in San Francisco, that he was working too hard. 

He quit freelancing and never went back.

Ben taught himself Cinema 4D during COVID and started designing a physical keyboard in Figma. Now he's a household name in motion design, works at Framer, and takes on all manner of passion projects.

We get into the experimentation crash loop of learning 3D tools, why he treats passion projects like hobbies, and what he tells the young creative who wants to do it all.

Get our newsletter: https://uxtools.co

CHAPTERS
00:00 — Intro
01:45 — Comic books, GeoCities, and why Ben wanted to make video games
04:40 — Five years at Mango Languages and the 3D pivot during COVID
07:20 — "You don't need to know everything about a tool"
09:26 — The Polygon Runway course and finding your people
12:51 — The Knob: fantastical devices that probably can't exist
15:33 — Commerce vs. passion and treating creativity like a hobby
17:59 — Photoshop muscle memory and tools that refuse to die
19:47 — Storyboarding as the bridge between static and motion
21:36 — What motion tools still hide behind right-clicks
24:28 — From Figma mockups to firmware in C
29:45 — Moments of delight: what makes motion design captivating
34:20 — The Play-Doh people nobody liked
35:25 — Where AI actually helps creative work
37:32 — Advice for the young creative who wants to do it all
40:38 — "I doubled my salary freelancing. Then my wife said stop."
43:53 — Outro

LINKS
Ben Fryc — https://x.com/benfryc
Framer — https://framer.com

FOLLOW ME
Twitter/X — https://x.com/designertom
LinkedIn — https://linkedin.com/in/tommygeoco
Newsletter — https://uxtools.co

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Andy Allen: Why He Takes 3 Years to Build Apps. Andy Allen: Why He Takes 3 Years to Build Apps. full 9ed5cf32-9441-4dd4-b2c1-653b5b41e75d https://share.transistor.fm/s/eba95e0e Andy Allen raised 5 million, built a hardware-software company, had a decent exit, and then walked away from all of it. Most founders would double down and scale. 

Andy did the opposite. 

He started Not Boring Software — fully bootstrapped, no investors, making apps that feel like nothing else on your phone. 

What Andy is doing isn't just different, it's proof that there's another path most designers don't even know exists. You don't have to raise money, scale fast or break things. 

You can just make something beautiful with a point of view where people can feel you in the work.

A refreshing conversation for those tired of the ambient noise lately.

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 - Walking away from 5 million
02:27 - Camera app becomes biggest launch yet
04:04 - Why speed is overrated for quality work
07:25 - Fully bootstrapped vs VC funding pressure
09:17 - Physical prototypes and 3D printing process
13:09 - Avoiding AI hype, focusing on interface innovation
15:45 - Game design principles in everyday apps
18:36 - The "kid in the cockpit" design philosophy
20:49 - Creative recovery and exploration process
22:49 - Leaving VC startup world for sustainable business
25:19 - Defining "enough" as a company and creator
28:44 - Being a beacon for other designers
32:11 - What's missing in design storytelling
36:51 - Hands in the clay vs management roles

LINKS:
Not Boring Software: https://notbor.ing
Andy Allen: https://x.com/asallen
Not Boring Camera App (iOS): https://apps.apple.com/us/app/not-boring-camera/id6737783441

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Andy Allen raised 5 million, built a hardware-software company, had a decent exit, and then walked away from all of it. Most founders would double down and scale. 

Andy did the opposite. 

He started Not Boring Software — fully bootstrapped, no investors, making apps that feel like nothing else on your phone. 

What Andy is doing isn't just different, it's proof that there's another path most designers don't even know exists. You don't have to raise money, scale fast or break things. 

You can just make something beautiful with a point of view where people can feel you in the work.

A refreshing conversation for those tired of the ambient noise lately.

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 - Walking away from 5 million
02:27 - Camera app becomes biggest launch yet
04:04 - Why speed is overrated for quality work
07:25 - Fully bootstrapped vs VC funding pressure
09:17 - Physical prototypes and 3D printing process
13:09 - Avoiding AI hype, focusing on interface innovation
15:45 - Game design principles in everyday apps
18:36 - The "kid in the cockpit" design philosophy
20:49 - Creative recovery and exploration process
22:49 - Leaving VC startup world for sustainable business
25:19 - Defining "enough" as a company and creator
28:44 - Being a beacon for other designers
32:11 - What's missing in design storytelling
36:51 - Hands in the clay vs management roles

LINKS:
Not Boring Software: https://notbor.ing
Andy Allen: https://x.com/asallen
Not Boring Camera App (iOS): https://apps.apple.com/us/app/not-boring-camera/id6737783441

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 02 Mar 2026 07:00:00 -0700 Tommy Geoco Tommy Geoco 2255 Andy Allen raised 5 million, built a hardware-software company, had a decent exit, and then walked away from all of it. Most founders would double down and scale. 

Andy did the opposite. 

He started Not Boring Software — fully bootstrapped, no investors, making apps that feel like nothing else on your phone. 

What Andy is doing isn't just different, it's proof that there's another path most designers don't even know exists. You don't have to raise money, scale fast or break things. 

You can just make something beautiful with a point of view where people can feel you in the work.

A refreshing conversation for those tired of the ambient noise lately.

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 - Walking away from 5 million
02:27 - Camera app becomes biggest launch yet
04:04 - Why speed is overrated for quality work
07:25 - Fully bootstrapped vs VC funding pressure
09:17 - Physical prototypes and 3D printing process
13:09 - Avoiding AI hype, focusing on interface innovation
15:45 - Game design principles in everyday apps
18:36 - The "kid in the cockpit" design philosophy
20:49 - Creative recovery and exploration process
22:49 - Leaving VC startup world for sustainable business
25:19 - Defining "enough" as a company and creator
28:44 - Being a beacon for other designers
32:11 - What's missing in design storytelling
36:51 - Hands in the clay vs management roles

LINKS:
Not Boring Software: https://notbor.ing
Andy Allen: https://x.com/asallen
Not Boring Camera App (iOS): https://apps.apple.com/us/app/not-boring-camera/id6737783441

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Stephen Haney: He Canceled Figma 4 Months Ago. Here's What He Built Instead. Stephen Haney: He Canceled Figma 4 Months Ago. Here's What He Built Instead. full 9deacaeb-d123-4530-abcf-fc5c294be142 https://share.transistor.fm/s/a81947fa Stephen Haney has been quietly building design tools for years. Now he's betting that the canvas wants to talk to your agents.

Paper just shipped MCP support. I've been playing with it. It's wild.

We talked about why he thinks the future stack is just three tools, why his team canceled Figma four months ago, and what happens when your production site becomes your source of truth for design.

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 - Everything changed in nine months
03:57 - Where the puck is going
05:08 - Figma's walled garden problem
06:18 - Agent + Code Review + Canvas
11:42 - Did agents kill collaboration?
15:18 - They canceled Figma 4 months ago
17:27 - What MCP actually means
21:03 - Live demo: production → canvas → code

LINKS:
Paper: https://paper.design
Stephen: https://x.com/stephenhaney

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: / itsdesignertom
LinkedIn: / tommygeoco

]]> Stephen Haney has been quietly building design tools for years. Now he's betting that the canvas wants to talk to your agents.

Paper just shipped MCP support. I've been playing with it. It's wild.

We talked about why he thinks the future stack is just three tools, why his team canceled Figma four months ago, and what happens when your production site becomes your source of truth for design.

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 - Everything changed in nine months
03:57 - Where the puck is going
05:08 - Figma's walled garden problem
06:18 - Agent + Code Review + Canvas
11:42 - Did agents kill collaboration?
15:18 - They canceled Figma 4 months ago
17:27 - What MCP actually means
21:03 - Live demo: production → canvas → code

LINKS:
Paper: https://paper.design
Stephen: https://x.com/stephenhaney

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: / itsdesignertom
LinkedIn: / tommygeoco

]]> Mon, 23 Feb 2026 07:00:00 -0700 Tommy Geoco Tommy Geoco 2810 Stephen Haney has been quietly building design tools for years. Now he's betting that the canvas wants to talk to your agents.

Paper just shipped MCP support. I've been playing with it. It's wild.

We talked about why he thinks the future stack is just three tools, why his team canceled Figma four months ago, and what happens when your production site becomes your source of truth for design.

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 - Everything changed in nine months
03:57 - Where the puck is going
05:08 - Figma's walled garden problem
06:18 - Agent + Code Review + Canvas
11:42 - Did agents kill collaboration?
15:18 - They canceled Figma 4 months ago
17:27 - What MCP actually means
21:03 - Live demo: production → canvas → code

LINKS:
Paper: https://paper.design
Stephen: https://x.com/stephenhaney

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: / itsdesignertom
LinkedIn: / tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Weber Wong: One Person Should Have the Creative Power of Pixar. Weber Wong: One Person Should Have the Creative Power of Pixar. full ceac2da6-6c8d-4c9a-8217-ea722a025bdb https://share.transistor.fm/s/75aa0209 Weber Wong was supposed to be a venture capitalist. Then he realized he wouldn't back himself, so he quit, moved to New York, and got a job at a coffee shop.

Now he's building Flora, one of the most uniquely-positioned AI tools for creative teams.

We talked about why node-based tools have such a bad reputation (and how Flora's fixing it), what "anti-slop" actually means when you're building AI creative tools, and the moment Pentagram reached out and he realized he'd accidentally built something useful.

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 - "They've been cooking"
02:11 - From VC to coffee shop to Flora
05:37 - The pain cave vs. Plato's cave
08:38 - Poetry as the entry point
11:34 - First time using an LLM
13:26 - "The world's most powerful creative operating system"
16:21 - Commerce vs. art — does it have to be at odds?
19:12 - A Berkeley professor and Cat's Cradle
20:25 - Fine-tuning GPT-2 on his own poetry
25:42 - Why node-based?
28:50 - The iceberg: low barrier, high ceiling
32:56 - What "anti-slop" actually means
40:48 - When Pentagram reached out
44:51 - Advice for the next generation of creatives

LINKS:
Flora: https://flora.ai
Weber Wong: https://x.com/weberwongwong

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Weber Wong was supposed to be a venture capitalist. Then he realized he wouldn't back himself, so he quit, moved to New York, and got a job at a coffee shop.

Now he's building Flora, one of the most uniquely-positioned AI tools for creative teams.

We talked about why node-based tools have such a bad reputation (and how Flora's fixing it), what "anti-slop" actually means when you're building AI creative tools, and the moment Pentagram reached out and he realized he'd accidentally built something useful.

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 - "They've been cooking"
02:11 - From VC to coffee shop to Flora
05:37 - The pain cave vs. Plato's cave
08:38 - Poetry as the entry point
11:34 - First time using an LLM
13:26 - "The world's most powerful creative operating system"
16:21 - Commerce vs. art — does it have to be at odds?
19:12 - A Berkeley professor and Cat's Cradle
20:25 - Fine-tuning GPT-2 on his own poetry
25:42 - Why node-based?
28:50 - The iceberg: low barrier, high ceiling
32:56 - What "anti-slop" actually means
40:48 - When Pentagram reached out
44:51 - Advice for the next generation of creatives

LINKS:
Flora: https://flora.ai
Weber Wong: https://x.com/weberwongwong

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 16 Feb 2026 07:00:00 -0700 Tommy Geoco Tommy Geoco 2870 Weber Wong was supposed to be a venture capitalist. Then he realized he wouldn't back himself, so he quit, moved to New York, and got a job at a coffee shop.

Now he's building Flora, one of the most uniquely-positioned AI tools for creative teams.

We talked about why node-based tools have such a bad reputation (and how Flora's fixing it), what "anti-slop" actually means when you're building AI creative tools, and the moment Pentagram reached out and he realized he'd accidentally built something useful.

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 - "They've been cooking"
02:11 - From VC to coffee shop to Flora
05:37 - The pain cave vs. Plato's cave
08:38 - Poetry as the entry point
11:34 - First time using an LLM
13:26 - "The world's most powerful creative operating system"
16:21 - Commerce vs. art — does it have to be at odds?
19:12 - A Berkeley professor and Cat's Cradle
20:25 - Fine-tuning GPT-2 on his own poetry
25:42 - Why node-based?
28:50 - The iceberg: low barrier, high ceiling
32:56 - What "anti-slop" actually means
40:48 - When Pentagram reached out
44:51 - Advice for the next generation of creatives

LINKS:
Flora: https://flora.ai
Weber Wong: https://x.com/weberwongwong

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Pietro Schirano: He Solved Figma-to-Code. It Went Viral Overnight. Pietro Schirano: He Solved Figma-to-Code. It Went Viral Overnight. full ad267293-a9b1-4272-9890-78c38b3f8c6e https://share.transistor.fm/s/e17806e6 Pietro Schirano built one of the first AI search engines before Perplexity existed. He created Cloud Engineer, an open source tool with 11,000+ GitHub stars that got him hired at Anthropic. 

Now he's building @magicpathai (check it out at https://magicpath.ai).
 
We talked about their Figma Connect feature that went viral last week, why he thinks vibe coding is "fast food" (and when you need slow food instead), and there's this moment where he describes two AI plugins combining to do something he never programmed — and how it changed how he thinks about what these models can do.

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 - "This thing seems like it understands"
02:03 - Designer to engineer pipeline
02:29 - The urge to create
05:17 - Before Designer GPT
08:35 - The moment two plugins combined on their own
10:40 - "I shipped four apps in 14 days"
11:52 - Bell Labs reached out about Cloud Engineer
13:41 - Will everyone build their own software?
18:41 - Where prototyping fits now
20:01 - How enterprise teams use MagicPath
24:51 - Vibe coding is fast food. This is slow food.
27:13 - Figma Connect and the viral reception
30:49 - What makes a good canvas editor
35:05 - Live demo: Figma to working code
39:48 - Extracting design systems automatically
50:32 - "You're living in the future"
52:47 - Advice for overwhelmed designers
55:09 - "If we remove the love people have for their work, we fail"

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
MagicPath: https://magicpath.ai
Follow Pietro: https://x.com/skirano

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Pietro Schirano built one of the first AI search engines before Perplexity existed. He created Cloud Engineer, an open source tool with 11,000+ GitHub stars that got him hired at Anthropic. 

Now he's building @magicpathai (check it out at https://magicpath.ai).
 
We talked about their Figma Connect feature that went viral last week, why he thinks vibe coding is "fast food" (and when you need slow food instead), and there's this moment where he describes two AI plugins combining to do something he never programmed — and how it changed how he thinks about what these models can do.

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 - "This thing seems like it understands"
02:03 - Designer to engineer pipeline
02:29 - The urge to create
05:17 - Before Designer GPT
08:35 - The moment two plugins combined on their own
10:40 - "I shipped four apps in 14 days"
11:52 - Bell Labs reached out about Cloud Engineer
13:41 - Will everyone build their own software?
18:41 - Where prototyping fits now
20:01 - How enterprise teams use MagicPath
24:51 - Vibe coding is fast food. This is slow food.
27:13 - Figma Connect and the viral reception
30:49 - What makes a good canvas editor
35:05 - Live demo: Figma to working code
39:48 - Extracting design systems automatically
50:32 - "You're living in the future"
52:47 - Advice for overwhelmed designers
55:09 - "If we remove the love people have for their work, we fail"

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
MagicPath: https://magicpath.ai
Follow Pietro: https://x.com/skirano

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 09 Feb 2026 07:00:00 -0700 Tommy Geoco Tommy Geoco 3366 Pietro Schirano built one of the first AI search engines before Perplexity existed. He created Cloud Engineer, an open source tool with 11,000+ GitHub stars that got him hired at Anthropic. 

Now he's building @magicpathai (check it out at https://magicpath.ai).
 
We talked about their Figma Connect feature that went viral last week, why he thinks vibe coding is "fast food" (and when you need slow food instead), and there's this moment where he describes two AI plugins combining to do something he never programmed — and how it changed how he thinks about what these models can do.

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 - "This thing seems like it understands"
02:03 - Designer to engineer pipeline
02:29 - The urge to create
05:17 - Before Designer GPT
08:35 - The moment two plugins combined on their own
10:40 - "I shipped four apps in 14 days"
11:52 - Bell Labs reached out about Cloud Engineer
13:41 - Will everyone build their own software?
18:41 - Where prototyping fits now
20:01 - How enterprise teams use MagicPath
24:51 - Vibe coding is fast food. This is slow food.
27:13 - Figma Connect and the viral reception
30:49 - What makes a good canvas editor
35:05 - Live demo: Figma to working code
39:48 - Extracting design systems automatically
50:32 - "You're living in the future"
52:47 - Advice for overwhelmed designers
55:09 - "If we remove the love people have for their work, we fail"

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
MagicPath: https://magicpath.ai
Follow Pietro: https://x.com/skirano

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Sara Vienna: Metalab's "Kind Not Nice" Rule Changed How She Gives Feedback. Sara Vienna: Metalab's "Kind Not Nice" Rule Changed How She Gives Feedback. full a9dced9f-28a3-445d-8b3f-d4259f2edf10 https://share.transistor.fm/s/5c3d967b Sara Vienna is the Chief Design Officer at Metalab. Slack, Uber, Coinbase... the list of products that came out of that shop is GOAT'd.

We talked about how they actually ship that work, their Tarantino process, why measuring velocity is "absolute bullshit," and a culture rule called "kind not nice" that changed how I think about feedback.

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 - "Designers are at a huge advantage"
01:58 - Learning Photoshop because tobacco companies lost a lawsuit
04:54 - "I was a really shitty designer first"
08:45 - Speed vs quality: earning space for the work you're proud of
12:05 - How MetaLab ships consistently
15:21 - The Tarantino process explained
17:16 - Building a culture of candid feedback
19:45 - "Kind not nice"
20:26 - Making space for play
26:45 - Burnout and what actually helps
30:05 - How MetaLab uses AI
35:07 - Designers marry the head and the heart
38:47 - Team structures: smaller but mightier
41:59 - T-shaped designers and specialists
44:34 - Why leaders need to stay in the work
48:00 - Advice for first-time design leaders

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Sara Vienna: https://www.linkedin.com/in/saravienna/
MetaLab: https://metalab.com

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Sara Vienna is the Chief Design Officer at Metalab. Slack, Uber, Coinbase... the list of products that came out of that shop is GOAT'd.

We talked about how they actually ship that work, their Tarantino process, why measuring velocity is "absolute bullshit," and a culture rule called "kind not nice" that changed how I think about feedback.

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 - "Designers are at a huge advantage"
01:58 - Learning Photoshop because tobacco companies lost a lawsuit
04:54 - "I was a really shitty designer first"
08:45 - Speed vs quality: earning space for the work you're proud of
12:05 - How MetaLab ships consistently
15:21 - The Tarantino process explained
17:16 - Building a culture of candid feedback
19:45 - "Kind not nice"
20:26 - Making space for play
26:45 - Burnout and what actually helps
30:05 - How MetaLab uses AI
35:07 - Designers marry the head and the heart
38:47 - Team structures: smaller but mightier
41:59 - T-shaped designers and specialists
44:34 - Why leaders need to stay in the work
48:00 - Advice for first-time design leaders

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Sara Vienna: https://www.linkedin.com/in/saravienna/
MetaLab: https://metalab.com

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 02 Feb 2026 07:00:00 -0700 Tommy Geoco Tommy Geoco 3376 Sara Vienna is the Chief Design Officer at Metalab. Slack, Uber, Coinbase... the list of products that came out of that shop is GOAT'd.

We talked about how they actually ship that work, their Tarantino process, why measuring velocity is "absolute bullshit," and a culture rule called "kind not nice" that changed how I think about feedback.

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 - "Designers are at a huge advantage"
01:58 - Learning Photoshop because tobacco companies lost a lawsuit
04:54 - "I was a really shitty designer first"
08:45 - Speed vs quality: earning space for the work you're proud of
12:05 - How MetaLab ships consistently
15:21 - The Tarantino process explained
17:16 - Building a culture of candid feedback
19:45 - "Kind not nice"
20:26 - Making space for play
26:45 - Burnout and what actually helps
30:05 - How MetaLab uses AI
35:07 - Designers marry the head and the heart
38:47 - Team structures: smaller but mightier
41:59 - T-shaped designers and specialists
44:34 - Why leaders need to stay in the work
48:00 - Advice for first-time design leaders

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Sara Vienna: https://www.linkedin.com/in/saravienna/
MetaLab: https://metalab.com

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Lee Black: He Makes Figma Do Things It Wasn't Designed For. Lee Black: He Makes Figma Do Things It Wasn't Designed For. full 86c53d38-3a04-45fe-8d35-104589ddef87 https://share.transistor.fm/s/4acfcf1a Lee Black has been designing for 25 years. He made those Figma pills with goldfish swimming inside. He also ran an app company that nearly broke him.

We talked about chasing money that never made him happy, why his tool stack hasn't really changed in a decade, and what happens when you master your tools so deeply that the rules start to bend.

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 - "It's not about learning everything"
01:59 - Taking apart toys to understand how they work
04:35 - Speed vs. quality
07:19 - Music came first
09:29 - His tool stack (it's simpler than you think)
11:03 - "It hasn't really changed that much"
12:44 - ChatGPT as an ideas buddy
14:40 - How Midlife Engineering was born
16:10 - What "polish" means to him
18:17 - The Matrix scene that started the pills
20:36 - "I want to put a fucking goldfish in there"
21:09 - Designing with restraint
23:27 - Dieter Rams as jazz, not gospel
26:03 - Protecting taste when you scale
31:05 - The app company that broke him
48:16 - Advice for designers struggling right now
51:57 - If nothing mattered, what would you work on?

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Lee Black: https://x.com/mrblackstudio
1042 Studio: https://1042.studio
Midlife Engineering: https://midlife.engineering

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Lee Black has been designing for 25 years. He made those Figma pills with goldfish swimming inside. He also ran an app company that nearly broke him.

We talked about chasing money that never made him happy, why his tool stack hasn't really changed in a decade, and what happens when you master your tools so deeply that the rules start to bend.

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 - "It's not about learning everything"
01:59 - Taking apart toys to understand how they work
04:35 - Speed vs. quality
07:19 - Music came first
09:29 - His tool stack (it's simpler than you think)
11:03 - "It hasn't really changed that much"
12:44 - ChatGPT as an ideas buddy
14:40 - How Midlife Engineering was born
16:10 - What "polish" means to him
18:17 - The Matrix scene that started the pills
20:36 - "I want to put a fucking goldfish in there"
21:09 - Designing with restraint
23:27 - Dieter Rams as jazz, not gospel
26:03 - Protecting taste when you scale
31:05 - The app company that broke him
48:16 - Advice for designers struggling right now
51:57 - If nothing mattered, what would you work on?

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Lee Black: https://x.com/mrblackstudio
1042 Studio: https://1042.studio
Midlife Engineering: https://midlife.engineering

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 26 Jan 2026 07:00:00 -0700 Tommy Geoco Tommy Geoco 3250 Lee Black has been designing for 25 years. He made those Figma pills with goldfish swimming inside. He also ran an app company that nearly broke him.

We talked about chasing money that never made him happy, why his tool stack hasn't really changed in a decade, and what happens when you master your tools so deeply that the rules start to bend.

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 - "It's not about learning everything"
01:59 - Taking apart toys to understand how they work
04:35 - Speed vs. quality
07:19 - Music came first
09:29 - His tool stack (it's simpler than you think)
11:03 - "It hasn't really changed that much"
12:44 - ChatGPT as an ideas buddy
14:40 - How Midlife Engineering was born
16:10 - What "polish" means to him
18:17 - The Matrix scene that started the pills
20:36 - "I want to put a fucking goldfish in there"
21:09 - Designing with restraint
23:27 - Dieter Rams as jazz, not gospel
26:03 - Protecting taste when you scale
31:05 - The app company that broke him
48:16 - Advice for designers struggling right now
51:57 - If nothing mattered, what would you work on?

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Lee Black: https://x.com/mrblackstudio
1042 Studio: https://1042.studio
Midlife Engineering: https://midlife.engineering

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Escha Vera: She Trained Her Own AI to Make Art. Escha Vera: She Trained Her Own AI to Make Art. full 8d05a900-3d4f-4505-b1df-5635de474ce4 https://share.transistor.fm/s/016b4a6f Escha Vera got death threats for posting AI art. She kept posting anyway.

Perplexity's designer runs a record label, trained her own LoRAs, and built the Comet invitations that broke the internet — each one unique, generated at scale, but deeply intentional.

We talk about the hate, the ethics, and why prompting isn't a gimmick skill, but communication.

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](https://uxtools.co/)

CHAPTERS:
00:00 - "I can't post anything without death threats"
01:48 - How I found Escha's work
02:46 - Myspace and Neopets taught her to code
04:39 - Losing self-expression in client work
06:54 - "I call myself a designer and don't elaborate"
08:05 - Perplexity's culture: high trust, high autonomy
09:13 - "There's no roadmap, just do it"
11:53 - How the Comet invitations actually got made
14:51 - Scaling unique outputs to 10K+ generations
17:44 - Evaluating AI tools as inputs vs outputs
20:16 - Pushing Midjourney to break terms of service
21:35 - "Being a good designer is about communication"
24:22 - Trial and error prompting with Comet
26:22 - Prompting as a second-class citizen to features
30:48 - "Can you be pro AI and pro self-expression?"
36:13 - The ethics question that kept her at Descript
38:35 - The hate and vitriol from sharing AI work
40:51 - "Ask how it was made before throwing hate"
43:31 - The blurred line: how much of it is AI?
45:31 - Should we disclose AI in our work?
48:40 - Daily driving tools at Perplexity
50:37 - The spinning planet she shipped in 5 minutes

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.

LINKS:
UX Tools Newsletter: [https://uxtools.co](https://uxtools.co/)
Follow Escha: https://x.com/eschadiol
Perplexity: [https://perplexity.com](https://perplexity.com/)
Comet: https://www.perplexity.ai/comet

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Escha Vera got death threats for posting AI art. She kept posting anyway.

Perplexity's designer runs a record label, trained her own LoRAs, and built the Comet invitations that broke the internet — each one unique, generated at scale, but deeply intentional.

We talk about the hate, the ethics, and why prompting isn't a gimmick skill, but communication.

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](https://uxtools.co/)

CHAPTERS:
00:00 - "I can't post anything without death threats"
01:48 - How I found Escha's work
02:46 - Myspace and Neopets taught her to code
04:39 - Losing self-expression in client work
06:54 - "I call myself a designer and don't elaborate"
08:05 - Perplexity's culture: high trust, high autonomy
09:13 - "There's no roadmap, just do it"
11:53 - How the Comet invitations actually got made
14:51 - Scaling unique outputs to 10K+ generations
17:44 - Evaluating AI tools as inputs vs outputs
20:16 - Pushing Midjourney to break terms of service
21:35 - "Being a good designer is about communication"
24:22 - Trial and error prompting with Comet
26:22 - Prompting as a second-class citizen to features
30:48 - "Can you be pro AI and pro self-expression?"
36:13 - The ethics question that kept her at Descript
38:35 - The hate and vitriol from sharing AI work
40:51 - "Ask how it was made before throwing hate"
43:31 - The blurred line: how much of it is AI?
45:31 - Should we disclose AI in our work?
48:40 - Daily driving tools at Perplexity
50:37 - The spinning planet she shipped in 5 minutes

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.

LINKS:
UX Tools Newsletter: [https://uxtools.co](https://uxtools.co/)
Follow Escha: https://x.com/eschadiol
Perplexity: [https://perplexity.com](https://perplexity.com/)
Comet: https://www.perplexity.ai/comet

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 19 Jan 2026 07:00:00 -0700 Tommy Geoco Tommy Geoco 3346 Escha Vera got death threats for posting AI art. She kept posting anyway.

Perplexity's designer runs a record label, trained her own LoRAs, and built the Comet invitations that broke the internet — each one unique, generated at scale, but deeply intentional.

We talk about the hate, the ethics, and why prompting isn't a gimmick skill, but communication.

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](https://uxtools.co/)

CHAPTERS:
00:00 - "I can't post anything without death threats"
01:48 - How I found Escha's work
02:46 - Myspace and Neopets taught her to code
04:39 - Losing self-expression in client work
06:54 - "I call myself a designer and don't elaborate"
08:05 - Perplexity's culture: high trust, high autonomy
09:13 - "There's no roadmap, just do it"
11:53 - How the Comet invitations actually got made
14:51 - Scaling unique outputs to 10K+ generations
17:44 - Evaluating AI tools as inputs vs outputs
20:16 - Pushing Midjourney to break terms of service
21:35 - "Being a good designer is about communication"
24:22 - Trial and error prompting with Comet
26:22 - Prompting as a second-class citizen to features
30:48 - "Can you be pro AI and pro self-expression?"
36:13 - The ethics question that kept her at Descript
38:35 - The hate and vitriol from sharing AI work
40:51 - "Ask how it was made before throwing hate"
43:31 - The blurred line: how much of it is AI?
45:31 - Should we disclose AI in our work?
48:40 - Daily driving tools at Perplexity
50:37 - The spinning planet she shipped in 5 minutes

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.

LINKS:
UX Tools Newsletter: [https://uxtools.co](https://uxtools.co/)
Follow Escha: https://x.com/eschadiol
Perplexity: [https://perplexity.com](https://perplexity.com/)
Comet: https://www.perplexity.ai/comet

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Devin Matthews: How He Became YouTube's Best New Filmmaker. Devin Matthews: How He Became YouTube's Best New Filmmaker. full c5a2fd22-aba1-4c56-a7cd-cbfac069acb5 https://share.transistor.fm/s/3300cba7 Devin Matthews rebranded his favorite sandwich shop in an effort to rediscover his love for the game. For free. 

He made a documentary ab out it called @SuprOrdinary.

Then his YouTube channel exploded.

Buck's Art Director reveals why SuprOrdinary almost started as a way to sell his feces for passive income (seriously), and how his cousin's death made him ask: "If I passed away tomorrow, would I feel like I did my best work?"

We talk the stress of medical bills, creative identity crises, and why making something you'd actually enjoy might be the only strategy that works.

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 - "Make something you'd enjoy"
02:02 - Devin became my favorite creator
05:22 - The not-so-romantic origin of Super Ordinary
06:30 - Passive income research gone wrong
07:52 - From teaching courses to creative entertainment
10:12 - Being a one-man band (then accepting help)
12:32 - The brainstorm meeting problem
14:09 - How to keep creative people around
21:08 - Balancing money and creative fulfillment
22:10 - "Life is short. Am I doing what I want?"
34:28 - The anxiety of going viral
39:14 - Playing the YouTube algorithm game
40:10 - TikTok gave me permission to experiment
43:39 - The aversion to being sold to
46:16 - Do you call yourself an influencer?
50:02 - Labels: designer, art director, filmmaker?
53:48 - "I still don't feel like a filmmaker"
57:59 - Who are we even making this for?
01:06:29 - Presenting designs as storytelling
01:13:32 - AI and the human side of creativity

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Devin: https://www.instagram.com/suprordinary
SuprOrdinary: @SuprOrdinary 
Buck: https://buck.co

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Devin Matthews rebranded his favorite sandwich shop in an effort to rediscover his love for the game. For free. 

He made a documentary ab out it called @SuprOrdinary.

Then his YouTube channel exploded.

Buck's Art Director reveals why SuprOrdinary almost started as a way to sell his feces for passive income (seriously), and how his cousin's death made him ask: "If I passed away tomorrow, would I feel like I did my best work?"

We talk the stress of medical bills, creative identity crises, and why making something you'd actually enjoy might be the only strategy that works.

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 - "Make something you'd enjoy"
02:02 - Devin became my favorite creator
05:22 - The not-so-romantic origin of Super Ordinary
06:30 - Passive income research gone wrong
07:52 - From teaching courses to creative entertainment
10:12 - Being a one-man band (then accepting help)
12:32 - The brainstorm meeting problem
14:09 - How to keep creative people around
21:08 - Balancing money and creative fulfillment
22:10 - "Life is short. Am I doing what I want?"
34:28 - The anxiety of going viral
39:14 - Playing the YouTube algorithm game
40:10 - TikTok gave me permission to experiment
43:39 - The aversion to being sold to
46:16 - Do you call yourself an influencer?
50:02 - Labels: designer, art director, filmmaker?
53:48 - "I still don't feel like a filmmaker"
57:59 - Who are we even making this for?
01:06:29 - Presenting designs as storytelling
01:13:32 - AI and the human side of creativity

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Devin: https://www.instagram.com/suprordinary
SuprOrdinary: @SuprOrdinary 
Buck: https://buck.co

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Fri, 09 Jan 2026 07:00:00 -0700 Tommy Geoco Tommy Geoco 4738 Devin Matthews rebranded his favorite sandwich shop in an effort to rediscover his love for the game. For free. 

He made a documentary ab out it called @SuprOrdinary.

Then his YouTube channel exploded.

Buck's Art Director reveals why SuprOrdinary almost started as a way to sell his feces for passive income (seriously), and how his cousin's death made him ask: "If I passed away tomorrow, would I feel like I did my best work?"

We talk the stress of medical bills, creative identity crises, and why making something you'd actually enjoy might be the only strategy that works.

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 - "Make something you'd enjoy"
02:02 - Devin became my favorite creator
05:22 - The not-so-romantic origin of Super Ordinary
06:30 - Passive income research gone wrong
07:52 - From teaching courses to creative entertainment
10:12 - Being a one-man band (then accepting help)
12:32 - The brainstorm meeting problem
14:09 - How to keep creative people around
21:08 - Balancing money and creative fulfillment
22:10 - "Life is short. Am I doing what I want?"
34:28 - The anxiety of going viral
39:14 - Playing the YouTube algorithm game
40:10 - TikTok gave me permission to experiment
43:39 - The aversion to being sold to
46:16 - Do you call yourself an influencer?
50:02 - Labels: designer, art director, filmmaker?
53:48 - "I still don't feel like a filmmaker"
57:59 - Who are we even making this for?
01:06:29 - Presenting designs as storytelling
01:13:32 - AI and the human side of creativity

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.

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Devin: https://www.instagram.com/suprordinary
SuprOrdinary: @SuprOrdinary 
Buck: https://buck.co

FOLLOW ME:
X / Twitter: https://x.com/designertom
Instagram: https://instagram.com/itsdesignertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Eric Simons: His Company Had 30 Days to Live. Then He Built Bolt. Eric Simons: His Company Had 30 Days to Live. Then He Built Bolt. full ae298c49-87e8-4b23-9ba0-bb921bfdd954 https://share.transistor.fm/s/1a107b00 This founder set an expiration ate for his company… and then hit 0M 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 0M 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 0,000 reality check vs a 00 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)

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Eric: https://x.com/EricSimons
Try Bolt: https://bolt.new

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> This founder set an expiration ate for his company… and then hit 0M 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 0M 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 0,000 reality check vs a 00 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)

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Eric: https://x.com/EricSimons
Try Bolt: https://bolt.new

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 11 Aug 2025 06:00:00 -0600 Tommy Geoco Tommy Geoco 1062 This founder set an expiration ate for his company… and then hit 0M 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 0M 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 0,000 reality check vs a 00 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)

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Eric: https://x.com/EricSimons
Try Bolt: https://bolt.new

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Ryo Lu: Why He Cloned Himself With Cursor. Ryo Lu: Why He Cloned Himself With Cursor. full 210870ae-ed49-4a98-a375-a97c593cd989 https://share.transistor.fm/s/8028e8d5 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): 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"

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Ryo: https://x.com/ryolu_
Try Cursor: https://cursor.ai

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> 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): 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"

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Ryo: https://x.com/ryolu_
Try Cursor: https://cursor.ai

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> Mon, 04 Aug 2025 09:00:00 -0600 Tommy Geoco Tommy Geoco 3165 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): 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"

LINKS:
UX Tools Newsletter: https://uxtools.co
Follow Ryo: https://x.com/ryolu_
Try Cursor: https://cursor.ai

FOLLOW ME:
YouTube: https://youtube.com/@designertom
Instagram: https://instagram.com/itsdesignertom
X / Twitter: https://x.com/designertom
LinkedIn: https://linkedin.com/in/tommygeoco

]]> creators, design, startup, entrepreneurship, creative process, internet culture, community, founders, digital art, tech, innovation, creativity, maker culture, online business No Ben Huffman: Every Investor Called His Idea Stupid. He Made $40M. Ben Huffman: Every Investor Called His Idea Stupid. He Made $40M. full 2ca468fa-71f9-4356-8596-08804b4b42da https://share.transistor.fm/s/915d924d 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)
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

]]> 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)
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

]]> Mon, 28 Jul 2025 09:58:55 -0600 Tommy Geoco Tommy Geoco 3169 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)
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

]]> contra, benhuffman, ui design, stateofplay, design, internetenjoyers, freelance, startup, paincave, creativity No