Dive Club 🤿

Ridd

Where designers never stop learning 💪

Dive Club is an interview series hosted by Ridd that is designed to unlock knowledge from today's most prolific designers. We go deep into craft, storytelling, tools, design engineering, startups, and much more.

You can find all of the episodes, key takeaways, and bonus resources here 👉 Dive.club

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212 episodes
Updated Wednesday
Explicit

Episodes212

Newest first

Charlie Deets - Designing the internet computer
Charlie Deets (https://x.com/charliedeets) has designed Safari, Arc, and now Dia… Needless to say he knows a thing or two about designing browsers 😅 So in this week’s episode Charlie shares the principles that guide his design practice and takes us on a tour of some of the finer craft details inside Dia. Some highlights: - Charlie’s tips for presenting design work - How to protect your special sauce as a designer - What makes Apple’s decision-making culture unique - The differences between designing at Apple vs. The Browser Co. - Why Charlie is spending more time in Figma and less time prototyping with AI - + a lot more - Nate Parrott episode on Dive Club (first design hire at the Browser Company): https://www.dive.club/deep-dives/nate-parrott - Gabriel Valdivia episode on Dive Club: https://www.dive.club/deep-dives/gabe-valdivia-2
Wednesday · 54 min
Pablo Stanley - Protecting your creativity in an AI world
Pablo Stanley (https://www.pablostanley.com/) has built as many creative tools as anyone in our industry. So in this episode he gives us a behind-the-scenes of his latest creations (including how he prototyped the all-new design mode in Vercel's v0). We go deep into: - The two types of design builders at Vercel - Pablo's approach to prototyping the new v0 - Behind the scenes of Pablo's custom design tools - What historic artists teach us about AI and creativity - How Pablo gets people excited about his ideas with Loom - The moment Pablo realized “I don’t design like this anymore” - Efecto: Pablo’s design tool with shaders, ASCII effects, and AI agents on the canvas (https://efecto.app/) - hilos: Pablo’s team chat that ships code (https://hilos.sh/)
July 21 · 51 min
Jason Yuan - Designing 99 "No"s for a single "Yes"
Jason Yuan (https://x.com/jasonyuan) has one of the most fascinating minds in design so naturally I like to keep tabs on what he is creating 😎 This episode is a deep dive into Jason Yuan’s creative process for Hivemind (his new social intelligence product). He screenshares dozens of unused concepts, novel art directions, brand identities, and everything in between. Some highlights: - The journey of designing Dot - Why Jason doesn’t believe in user research - The surprising sources Jason uses for design inspo - building a system to generate infinite branded images - How Jason thinks about art direction and world building - + a lot more
July 15 · 57 min
Meaghan Choi - Designing Claude Code (and what's coming next)
It kinda feels like how design operates at Anthropic is consistently 3-6 months ahead of the rest of the industry. As a result, Meaghan Choi (https://x.com/meaghaneschoi) (Design Lead for Claude Code) has quickly become a staple guest on this show. In today’s episode we go deep into her design process, how she uses the new Artifacts feature, how the shape of designer is evolving, and a lot more… Some highlights: - Designing experiences that don’t have UIs - How Meaghan collaborates with Claude Tag - What it’s like designing the Claude Code CLI - The shape of designers that will thrive in the coming years - Collaborating with the models for execution vs. brainstorming - + a lot more
July 8 · 53 min
Meng To - Codex superpowers for designers
Meng To (https://x.com/MengTo?lang=en) is one of the people I keep tabs on to see how he's evolving his workflow as he builds his ideas with AI. So I sat down with him to get a look into what his process looks like now… (spoiler: he’s moved everything to Codex) We do a ton of screen-sharing and go deep into his strategies for prompting, how to get better outputs from the models, and more 👇 Some highlights: Why Meng built his own local Notion tool Why Meng writes 0% of his own code now Strategies for design.md and agents.md files How Meng uses GPT Image 2 to brainstorm UI design How Meng’s workflow has evolved in the last 1.5 years a lot more
June 30 · 35 min
Loredana Crisan - Figma's big bets for the future of AI design
This week we are going behind the scenes of Config 2026 with Loredana Crisan (Figma’s Chief Design Officer) https://www.linkedin.com/in/loredanacrisan/ We talk about Figma’s vision for AI, why design is having “an identity crisis and a renaissance at the same time,” and what it means to use AI to express what’s already in your head (not outsource creativity to it). It’s a clarifying conversation about taste, tools, and the future of design 👇 Some highlights: - Designing systems not screens - Loredana’s mental model for AI as a tool - Building your own tools and mini apps in Figma - What Figma is learning in their own UX research - What types of designers Figma is hiring right now - + a lot more
June 24 · 50 min
Brett Williams - How a Visual Designer Became a Builder
What does it look like when a designer with zero technical background commits to shipping something real? That’s what this week’s episode with Brett Williams is all about. He gives us a behind-the-scenes of his journey building Gather including: Brett’s process for iterating on a design Brett’s new prototyping.md skill workflow How Brett maintains control while building with AI Brett’s strategy for adding sound design to Gather When Brett relies on Figma vs. explores directly in code a lot more
June 16 · 50 min
Ron Goldin - Building your ideas as a design leader
This week's episode is with Ron Goldin who has led design at Google, Shopify, UberEats, and in my opinion... he's the perfect example of what it looks like to thrive as a design leader in an AI world. So this week’s episode is a deep dive into his journey as a builder and it’s full of stories: Redesigning the Shopify checkout Ron’s unique research tactics for UberEats Building MTCHMKR from scratch in Lovable Navigating the job market as a design leader a lot more
June 9 · 54 min
How Anthropic, Every, & Ramp design with AI
A couple of weeks ago I recorded my first ever episode in front of a live audience (at Ramp HQ in NYC) 🗽 So today I’m excited to share the panel discussion recording with 3 incredible guests: Meaghan Choi who is the design lead for Claude Code and Cowork Dan Shipper who is the CEO of Every and one of my favorite thinkers when it comes to AI And Bradley Ziffer who is a design engineer at Ramp It’s a deep dive into AI design workflows at Anthropic, Ramp, and Every and I think you’ll enjoy it :) The event was hosted by Double Diamond and Ramp
June 2 · 39 min
Andy Madrick - Why AI changed design handoff forever
⭐️ Check out Andy’s course - Craft at Speed https://join.dive.club/maven-aff-andy-madrick Use code DIVECLUB for 15% off Andy Madrick ( https://x.com/andymadrick ) is rethinking what it means to be a designer in 2026. While at Notion, he’s developed a workflow where he prototypes directly in code, ships frontend PRs, and uses AI tools like Cursor to own the final polish of user interfaces. In this episode we get a look into how he keeps all these things in motion and still designs with insane attention to detail. Some highlights: Building one of Notion’s most visible UIs Why recreating interactions teaches you craft Owning the last 5-20% of frontend polish work The “jelly bean factory” problem with AI output When to start in Figma vs. jumping straight to code How Andy creates prototypes that content teams can edit a lot more
May 26 · 52 min
Tommy Geoco - The state of the design industry right now
Over the last few months, Tommy Geoco has went on site to study today’s top design teams (Vercel, Perplexity, Metalab, Ramp, etc.). So this week’s episode is a deep dive into all of the trends he’s seeing around AI workflows and where design is headed next. Some highlights: Why 59% of designers build their own tools Tommy’s current tool stack for AI design work What signals show AI fluency in job interviews Why internal tool building is the new career path Why now is the best time to grow in the design community How design workflows have become creative director roles a lot more Ben Blumenrose (mentioned as having good insights on design)
May 19 · 1 hr
Katarina Batina - Making big bets with design
How do the best designers shape strategy at companies like Shopify? That’s what today’s episode with Design Director Katarina Batina is all about. Some highlights: Balancing metrics and vision Redesigning the shopping cart UX Taking a big bet on the shopping feed How product strategy has changed with AI How to get people excited about your ideas How to make sure you don't overcook your app a lot more Katarina mentioned John Rundle and Luke Dupont
May 12 · 55 min
Rafa Conde - Make your designs memorable
Rafa Conde (https://x.com/rafahari) is a design engineer at Retro and one of the most creative designers I know. I still remember where I was when I first saw the video on his personal site (https://rafa.design/) 😂 In this episode we unpack what it means to design experiences that bring delight :) Some highlights: - Finding ways to introduce delight - How to make users feel something - The power of humor in your design - How to lean into video as a superpower - Balancing accessibility and delightful UX - Behind the scenes of Rafa's side projects - + a lot more - Metal Gear Solid (PlayStation 1) — directed by Hideo Kojima, referenced for its fourth-wall-breaking design moments (Meryl’s codec frequency hidden on the game box; Psycho Mantis boss fight requiring the controller to be switched from port 1 to port 2) - Sunlit app — gyroscope-based app for tracking sun position and light direction, referenced as a recent example of surprising UI: https://play.google.com/store/apps/details?id=io.lonepalm.coloringworld&pli=1 - Retro app — private social network for friends and family (what Instagram used to be); Rafa’s current employer: https://apps.apple.com/us/app/retro-photos-with-friends/id6443709020 - Splat app — Retro’s generative AI app for iPad/iPhone that turns photos of kids into coloring book pages: https://apps.apple.com/us/app/splat-magic-coloring-book/id6749165093 - Hand Mirror app — Rafa’s most popular side project, a menu bar camera app: [https://handmirror.app](https://handmirror.app/) - Gabe Valdivia’s episode — early Dive Club episode (~ep. 30) where Gabe talked about designers needing to be like “little TikTok creators” inside their orgs: https://www.dive.club/deep-dives/gabe-valdivia - Final Cut Pro — Rafa’s video editing tool of choice: https://creatorstudio.apple.com/info/try?itscg=20201&itsct=acs-sem-187498456050-794866723417&pt=2003&ct=css-187498456050-794866723417
May 5 · 59 min
Polly D’Arcy - Going from IC to VP of Design at Wealthsimple
Imagine going from IC to leading the Wealthsimple design team in a few short years… That was Polly D’arcy’s (https://www.linkedin.com/in/pollydarcy/) journey and today’s episode covers everything she’s learned along the way. We go deep into design leadership, craft, hiring, and a lot more. Some highlights: - Why Polly hires specialists over generalists - Tactics to nail your next portfolio presentation - What it looks like to lean into the moment with AI - How Polly defines design quality at WealthSimple - Polly’s go-to interview question to evaluate designers - How AI is changing team composition and design roles
April 28 · 55 min
Brandon Jacoby - Seeing Taste vs. Creating Taste as a designer
Capital, early Cash App, and most recently, X, all have one designer in common — [Brandon Jacoby](https://x.com/JacobyBrandon). In this episode Brandon is talking about how he’s combining his years of experience designing with fresh, high-functioning teams and is now launching an all-new independent practice to help founders push past good enough. He shares some really interesting thoughts on taste, being creative with AI, and how to thrive in a 0->1 environment. Some highlights: - The types of designer who get most amplified by AI - What it takes to thrive while designing a 0→1 experience - How Brandon is positioning himself as a new independent - The difference between "seeing taste" and "creating taste" - What Nikita (X Head of Product) taught Brandon about onboarding - + a lot more - John Lasseter (Pixar director) quote - https://www.youtube.com/watch?v=uFbOOjAC_Fg - Tolan app (mentioned as example of creative onboarding) - https://www.tolans.com/ - Owen Jennings at Block (Brandon’s mentor for 4 years) - https://www.linkedin.com/in/owenbrittonjennings/ - Nikita (former Head of Product at X) - https://x.com/nikitabier
April 21 · 52 min
Brian Lovin - How to level up with AI as a designer
When it comes to tools and workflows, Brian Lovin (https://x.com/brian_lovin) is someone I pay very close attention to. He’s actually the one who first got me hooked on Conductor (https://www.conductor.build/). But times are changing (again 😅)… So today’s episode is a deep dive into his design process and all of the ways he’s iterating on his approach to both using AI tools as well as building AI tools at Notion. If you like getting into the weeds of how the best designers are wrangling AI then you’re going to love this episode. Some highlights: - Why his first Notion design offsite was so impactful - How Brian built Notion’s prototyping playground - Why Brian has started using Cursor again - Practical tips for prompting AI more effectively - Behind-the-scenes of Brian’s new side project - How to stay relevant as a designer in an AI world - + a lot more - Agentation and Dialkit for frontend ([https://agentation.com](https://agentation.com/), https://joshpuckett.me/dialkit) - Cursor and Conductor for coding ([https://conductor.build](https://conductor.build/)) - Brian’s side project Shiori ([https://shiori.sh](https://shiori.sh/)) - Max Schoening nerd snipes Brian (https://x.com/mschoening) - Karri’s issue tracking is dead article (https://linear.app/next)
April 14 · 55 min
Ian Silber - What it's like designing at OpenAI
If you're like me you gotta be curious... what's it like designing at OpenAI? So I’m excited to share today’s episode with you :) It’s a deep dive with OpenAI’s Head of Product Design, Ian Silber (https://x.com/iansilber). Some highlights: **** - The traits of the best systems thinkers at OpenAI - What makes the design culture at OpenAI unique - The vision for OpenAI's dynamic interface library - What it's like designing around chat as a primitive - What makes designing with AI as a material so unique - How tools like Codex are changing the practice of design - + a lot more - Mike Matas and Brandon Walkin (creators of Origami) https://mikematas.com/ , https://medium.com/designatmeta/introducing-origami-live-and-origami-2-0-a68116294e65 - Cursor and Codex (AI coding tools) https://cursor.com/ ,(https://chatgpt.com/codex/?c_id=23226110534&c_agid=188421385415&c_crid=800871103650&c_kwid=kwd-111182835&c_ims=&c_pms=9017288&c_nw=g&c_dvc=c&gad_campaignid=23226110534&gbraid=0AAAAA-I0E5dO-SVXduV4xJjtnqTNMNrAP)
April 8 · 45 min
Marvin Schwaibold - Inside Shopify's New Product Design Studio
Remember when the Carl Rivera (https://www.dive.club/deep-dives/carl-rivera) told us about his vision to create the new Shopify Product Design Studio? Well in this episode I got to sit down with Marvin Schwaibold (https://x.com/MSchwaibold) from Molly studio who Shopify recently acquired to bring that vision to life. We go deep into creativity, Marvin's journey with Molly, how he's building his ideas with AI, and a lot more. Some highlights: - How to become a well of creative ideas - How AI unlocks how designers work at Shopify - What design differentiation looks like at Shopify - What Marvin has learned diving into Claude Code - How designers at Shopify create and leverage internal tools - Behind-the-scenes of redesigning the famous Collins website - + a lot more - Jaytel - Marvin’s design partner from Molly studio https://x.com/Jaytel - Brian Collins - legendary designer who worked on the Collins website redesign https://wearecollins.com/ - Carl Rivera - Shopify’s Chief Design Officer (referenced previous Dive Club episode) https://www.dive.club/deep-dives/carl-rivera - Design Fluid Interfaces video from Apple’s Human Interface team (2019) [https://developer.apple.com/br/videos/play/wwdc2018/803/?time=1551](https://developer.apple.com/videos/play/wwdc2019/808/) - Claude Code - AI coding tool by Anthropic https://claude.ai/login - Artifact - internal Shopify tool for showcasing design work https://www.linkedin.com/posts/jaytel_this-was-meant-to-stay-inside-shopify-but-activity-7422739773561384960-oqiU/
April 2 · 54 min
Flora Guo - How to accelerate your design career with AI
Flora Guo (https://x.com/floguo) has one of the more impressive career trajectories of anyone I've interviewed on this show. She's currently the founding design engineer at Paradigm. But before that Guillermo (Vercel CEO) personally DM'd her to join the Vercel team. So we're going deep into career growth, design engineering, what it's like being a founding designer at an AI-native startup. - What it’s like being a founding design engineer at Paradigm - The challenges of designing AI-first products that work at scale - Flora’s experiments with new design tools like Paper and Variant - What Flora learned working alongside top design engineers at Vercel - How Flora evolved her workflow with Claude Code over the past year - Mental models for using AI as a learning tool rather than just a task executor - + a lot more - Tokyo Design Forum (February 2026) - https://www.tokyodesignforum.com/ - UI Engineering 101 by Mariana Castillo and Derek Briggs - https://maven.com/pixeljanitor/uiengineering-101-for-designers - We talked about Rauno Freiberg's portfolio (Vercel design engineer) - https://rauno.me/ - New tools: Paper - https://join.dive.club/paper-ad-email
March 25 · 46 min
Kris Puckett - Becoming an AI-native designer
Today's episode is with Kris Puckett who has led design at Mercury, Dropbox, and now as a design manager at Stripe. His journey is the perfect example of what it looks like to lean into this moment in time with AI. Some highlights: - Behind the scenes of Kris’s Epilogue app - How to create custom skills with Claude Code - How to start building personal systems with AI - How Kris taught Claude to be a metal shader expert - Building internal tools and workflows with AI at Stripe - + a lot more
March 19 · 52 min

Dive Club 🤿

Charlie Deets - Designing the internet computer

Pablo Stanley - Protecting your creativity in an AI world

Jason Yuan - Designing 99 "No"s for a single "Yes"

Meaghan Choi - Designing Claude Code (and what's coming next)

Meng To - Codex superpowers for designers

Loredana Crisan - Figma's big bets for the future of AI design

Brett Williams - How a Visual Designer Became a Builder

Ron Goldin - Building your ideas as a design leader

How Anthropic, Every, & Ramp design with AI

Andy Madrick - Why AI changed design handoff forever

Tommy Geoco - The state of the design industry right now

Katarina Batina - Making big bets with design

Rafa Conde - Make your designs memorable

Polly D’Arcy - Going from IC to VP of Design at Wealthsimple

Brandon Jacoby - Seeing Taste vs. Creating Taste as a designer

Brian Lovin - How to level up with AI as a designer

Ian Silber - What it's like designing at OpenAI

Marvin Schwaibold - Inside Shopify's New Product Design Studio

Flora Guo - How to accelerate your design career with AI

Kris Puckett - Becoming an AI-native designer