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We talked about why designers are shipping production code now, why "UX designer" as a role feels outdated, and this framework she keeps coming back to: automate toil, augment creativity.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47:51 - Is "UX designer" becoming outdated?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

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

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

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

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

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

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

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

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

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