Dive Club 🤿

Someone asked me recently... if you had to join a design team, who would you want to work for?

And my answer was easy... Perplexity

So today's episode with Henry Modisett (https://x.com/henrymodis) (Perplexity's VP of Design) is a deep dive into what makes their design culture so special.

Some highlights:

- How to create a culture of decisiveness

- What signals Henry is looking for in designers

- Factors that influence Henry’s leadership style

- How to lay the right foundation fo...

Kyle Zantos is leading the new UX Tools Labs where he's responsible for figuring out what matters for new design tools and workflows.

As a result, he's pretty quickly become my go-to source as I transition into more of a builder with AI.

So this conversation is a deep dive into very specific tactics you can use on your own design engineering journey.

We'll go through recommended tools, workflows, and Kyle's process for building a design engineering "Skill" using Claude Code.

We talk a lot about using AI at startups…

But what are more established companies doing to scale AI prototyping?

What are the best ways to use AI to prototype with your design system?

That's what today's episode is all about because we're talking with Lewis Healey (https://x.com/Lewishealey) and Kylor Hall (https://www.linkedin.com/in/kylorhall/) about how they scaled AI prototyping at Atlassian.

Some highlights 👇

- Their vision for a truly AI-native design system

- What's worked to scale AI prototyping adoption

...

Today's episode goes deep into all of the design details in a new video collaboration tool called Flask.

But the reason I’m so inspired by this product goes far beyond the UI/UX…

Flask is designed and built by one person—Enrico Tartarotti—who was a PM before this so his journey is the perfect example of what it looks like to thrive as a generalist builder.

So this episode tells the story of what it took to build a well-crafted product and all of the lessons that he learned along the way.

As one of the fastest growing companies in the world, Lovable is scaling their design team by tapping into the [Dive Talent Network](https://www.dive.club/talent-network).

So I interviewed their Head of Design, [Nad Chishtie](https://x.com/nadonomy), to learn everything I can about how to get hired as a designer at Lovable.

Some highlights:

- A breakdown of a recent design hire’s portfolio

- How to avoid getting your portfolio screened out

- How to crush the later stages of the hiring process

...

What does it look like to own web design for one of the fastest growing AI companies in the world?

And how do you get that opportunity if you don’t have companies like Apple or Airbnb on your resumé?

That’s what this episode with [Roman Tesliuk](https://x.com/RomaTesla) is all about.

He walks us through the Eleven Labs Figma and talks about the tiniest of design decisions all the way to how he’s building a scalable website system.

We also go deep into Roman's side projects and all...

I’ve probably learned more about visual design from MDS than anyone in the design community.

So I wanted to go deep into the creative process behind the all-new Shift Nudge website to see how he explores visual ideas.

He takes us through his Figma file that is full of very good ideas that didn't ship.

And he even shows us how he built his own Mosaic tool in v0 which became the core motif of the site.

So if you're interested in seeing the windy creative process behind one of th...

I get shown a lot of tool demos and one thing is clear…

Canvas-based UX will play a pivotal role in how we interface with AI.

It’s a big reason why Figma just bought Weavy 👀

So I interviewed Steve Ruiz who is the founder of tldraw where he's spent over 3 years and $5 million dollars building the perfect canvas (which powers many of the startups that we've studied on this show).

Some highlights:

In one of the most popular episodes yet, Vitaly Friedman talked about what’s next for AI design patterns (https://www.dive.club/deep-dives/vitaly-friedman).

In that episode he frequently referenced Shape of AIl (https://www.shapeof.ai/) which is an incredible database of AI design patterns.

So I wanted to get to the source and go deep with the creator Emily Campbell (https://www.linkedin.com/in/emmiecampbell/) to learn how to design great AI experiences. Because she’s studied AI products more than just about anyone I’ve ever seen 👀

Some of my fav...

AI is fundamentally shifting the way we think about digital products and the core deliverables that we're bringing to the table as designers.

So I asked Geoffrey Litt (https://x.com/geoffreylitt) (Design Engineer at Notion) to share his vision for the future of malleable software and AI system design.

Here’s some highlights:

- The keys to effective system design

- Geoffrey’s workflow for “working like a surgeon”

- Why too many products become “nightmare bicycles”

- The principles of malleable software vs. disposable software

- Why v...

Craft gets you hired.

But business impact gets you promoted.

So this week’s episode with [Ryan Scott](https://www.linkedin.com/in/ryanscottcreative/) is a deep dive into how designers can think strategically about their career.

He shares a ton of lessons from his [PM Masterclass for designers](https://join.dive.club/ryan-scott-pm-masterclass-affiliate):

- What it looks like to grow your product muscles

- The right (and wrong) ways to get buy-in for your ideas

- Strategies for making data a part of your design practice

Board (https://board.fun/) has taken over social social media (and for good reason).

It’s one of the most obvious yet innovative products I’ve ever seen.

So as soon as Kevin Twohy (https://x.com/kevintwohy) shared a preview with me I knew we had to do an interview to get the behind-the-scenes (spoiler: I did buy it lol).

So this episode is a deep dive into his design process for the first ever tabletop game console:

- What he learned about prototyping hardware products

- Ho...

AI is reshaping how we design and build software, creating huge opportunities for designers who experiment, adapt, and help define what the practice looks like next. This session is your opportunity to learn directly from some of the best in the industry.

Imagine a world where handoff no longer exists and designers are moving fluidly in code…

[Drew Wilson](https://x.com/drewwilson) is one of the people pulling that future into the present so this week’s episode is a deep dive into his vision for the new design tool [Opacity](https://opacity.app/).

Some highlights:

- How team structures are changing

- How to stand out when everyone is a builder

- What design’s “Github moment” will look like

- The fracturing of the market for design tal...

Over the last few months one product has risen to the top of my inspiration list… ツSupercut (https://supercut.ai/)

The point of this episode is to figure out what it takes to consistently reach that level of excellence.

How do you maintain that level of attention to detail while preserving the speed that you need to hit when going 0 -> 1 on a new product?

This week's episode is with David (https://x.com/okuiux?lang=en) and [Neil](https://x.com/neiltak) the cofounders of Supercut which has quickly become one of my f...

We’re talking about craft in B2B SaaS... but what is it like designing for frontier interfaces like the Apple watch or even neural interfaces?

We find out in this week’s episode with Rooz Mahdavian. (https://x.com/roozm)

He’s the design engineer at Neuralink so we're about to get pretty nerdy and talk about what it’s like designing an experience that allows someone to use a computer with just their mind.

The level of detail and first-principles design thinking is truly impressive.

Some highlights:

- What i...

Imagine it’s your first day as a designer at Perplexity... and the VP of Design hands you the keys for their all-new AI browser, [Comet](https://www.perplexity.ai/comet).

That’s the story for [Escha Vera](https://x.com/eschadiol).

So this week’s episode is a deep dive into her design process and what it looks like to use AI like an artist.

- How she designed Comet onboarding experience

- Creating generative invite codes using multiple AI tools

- How she created the Perplexity design system...

What does the perfect e-commerce platform look like in an AI era?

That’s the question Shopify’s Chief Design Officer Carl Rivera has set out to answer so this week’s episode is all about Shopify’s big bet on design and craft as the ultimate differentiator.

We go deep into:

- What happens when AI makes everyone a 7/10 designer

- What most design teams get wrong when casting vision

- How design can lead the creation of truly native AI experiences

- Why every designer at Shopi...

Only a select few have multiple episodes on Dive Club and today Catt Small joins the ranks.

She has a gift for turning messy ideas into practical next steps so it’s no wonder her Staff Designer course is one of the top-rated on Maven.

In this episode we go deep into all of the ways you can make an impact by building influence on your team and effectively casting vision for your product.

Some highlights:

What does it take to make people feel something with design...?

This week's guest is kind of an expert on the question.

Sara Vienna (https://x.com/sravienna?lang=en) , the Chief Design Officer at Metalab, talks about the responsibility that designers have to shape this AI world that we're entering without losing the heartbeat of a brand.

We don't hold back on the current state of the industry and what it feels like to be a designer today.

Some highlights:

- How to not get swept up in...

I think we're entering a world where the market for fractional design is about to explode…

So this week's episode is with one of my favorite people in the industry, Gabe Valdivia.

We're going to explore his independent journey → how he made the jump, how he's evolved the practice in year two, and all of the lessons he's learned along the way.

Some highlights:

Too much of designing a startup happens behind closed doors

So I want to work with the garage door open while building Inflight (https://www.inflight.co/) as much as possible.

You already saw a bunch of the nitty gritty UI details (https://www.youtube.com/watch?v=D39Dv9MSlhs)…

But when you’re going 0 to 1 on something, the storytelling piece is often the hardest part.

So this episode is a sneak peek of a recent presentation we gave in SF (and some behind-the-scenes commentary to go along with it).

What does it look like to advance your career in the age of AI?

That’s what this week’s episode with Dan Winer (Director of Product Design at Kit) is all about.

He shares insights from his top-rated Maven course "Strategy and Influence for Product Designers" (https://join.dive.club/dan-winer-course)

So if you want to learn how to go from pixel pusher to strategic partner then this is the episode for you 💪

Some highlights:

- Dan’s strategies for effective storytelling

- How to shine a light o...

This week's episode is with Andy Zhang who was the lead design engineer at Windsurf. So we're going to shine a light on all of the ways you can make an impact as a design engineer including:

He also shares some great stories and advice including:

I’d bet real money that you have been on Smashing Magazine at some point in the last 18 years…

Good news is, this week I got to interview the founder, Vitaly Friedman, who is also one of the leading thinkers in UX right now.

In this episode we go deep into how AI is changing the way we interact with digital products and how our patterns and processes are evolving as a result.

Some highlights:

If I told you someone had a background as a senior designer at companies like Uber, Dropbox, Apple, and Patreon then you'd be pretty impressed, right?

Same.

But Adam Noffsinger walked away from all of that to start Alma (which you might remember from the Smith+Diction episode).

So this episode is a deep dive into what it really looks like to go 0→1 as a design founder.

Adam even walks us through his Figma file for Alma so if you’re interesting in startups or designing something from nothing, then I thin...

This week’s episode is with Pietro Schirano who is the founder of the new design tool MagicPath and one of the true forward thinkers on AI. We go deep into the future of prototyping, design workflows, and what it takes to catalyze your career with AI.

Some highlights:

This week I got an inside look at Figma Make while talking to Holly and Nikolas all about the future of prototyping…

We get into real world use cases for different kinds of prototypes and how our workflow is evolving as designers.

One thing is abundantly clear, things aren’t so linear anymore.

Some highlights:

Last month we did the ultimate Raycast Deep Dive, but there's a lot in there… so this week I want to highlight just the segment from the product design team.

We go deep into how they collaborate, why they’ve started shipping more code, and what it takes to build a culture obsessed with craft.

Don’t forget to use code DIVE20YT to get 20% off your first purchase of any Lovable plan ❤️ Valid until August 21, 2025. Go to dive.club/lovable to start creating

Full Raycast episode - The Raycast Deep Dive

This week, Gunnar Gray (Product Design Lead at Perplexity) dives into the art of designing AI-native experiences.

He shares lessons from shaping Voice Mode and how prototyping with AI is changing the design process at Perplexity.

Some highlights:

Cursor is easily one of the most impactful companies in all of tech…

And this week's episode is with their Head of Design, Ryo Lu.

You might've heard of Ryo in this episode back when we talked about early Notion and systems design.

So this week we're going to get an inside look at how design operates at Cursor and all of Ryo's experiments with AI 👀

Some highlights:

This week's episode is with Julian Lehr who is the storytelling lead at Linear

So we're going to step out of the pixels for this conversation and focus more on how you can get people excited about what you're designing.

Because in the age of AI, stories are what makes your product defensible.

So we're going to go deep into Julian's creative process and how he kinda thinks of his role more as packaging.

Some highlights:

You probably know Intercom… but did you know they recently incubated a new startup called Fin that has already surpassed the core business?

They’ve pulled off a massive transition to an AI-native product and design org so today we’re going behind-the-scenes with their VP of Design Emmet Connolly.

Some highlights:

In last week’s episode, the Head of Design at The Browser Company shared a totally new way to think about your portfolio.

He says one of the most valuable things you can demonstrate today is the ability to solve real problems with code (no matter how small).

I’m literally doing this with a side project right now and I’ve learned a lot so I decided to share my new playbook for vibe coding 👇

Teo Connor (VP of Design at Airbnb): https://www.dive.club/deep-dives/air-bnb

Alex Schl...

Dia from The Browser Company has completely taken over the internet. We’re finally seeing what an AI-native browser can be and it’s pretty exciting :)

So this episode is a behind-the-scenes with their Head of Design, Dustin Senos.

Some highlights:

We mentioned Nate Parrott’s...

This week’s episode is a first of its kind because we’re doing the ultimate deep dive into one of my favorite products: Raycast

We’ll here from the founders, design team, and even the hype team and go deep into all kinds of topics:

This is easily the most in-de...

The last two weeks with Inflight have been the most exhilarating of my entire career…

So I want to use Dive Club  to provide unprecedented levels of access to life as a design founder.

I’m talking about the messy behind-the-scenes, hideous Figma concepts, and all of the winding turns that we've taken to get where we're at today.

This is gonna be as raw as it gets.

And hopefully by shining a light on some of the things I'm learning, it turns into a video series that you want to keep w...

This week's episode is with Darrin Henein who is the VP of Design at Shopify. We talk about how they create a culture of excellence and how AI is influencing the way they practice the design.

Some highlights:

There’s a new design tool called Subframe that’s officially caught my eye 👀

So I asked their co-founder Filip Skrzesinksi to give us a demo and talk through their vision.

I found some of their AI interaction patterns fascinating (especially the way they approach prototyping and contextual edits).

If you’re interested in the future of design tooling then I think you’ll like this episode and you can use the code DIVECLUB to get your first month free 👌

There are two types of companies today:

This week’s episode is all about #2 because we get to hear from Ioana Teleanu who was the first AI designer at Miro and is now a dedicated AI+Design consultant.

So a big theme of this conversation is how to identify the right opportunities to design AI into a product that’s already working. Ioana shares a bunch of stories and lessons learned from her time at Miro as well as a refreshing perspective on A...

This week we get to hear from Jesse Kulp who is the original designer for Google AI Studio.

He shares what it was like going 0→1 as the sole designer and his ideas for where AI design is headed next

I think we're gonna look back in a couple years, the kind of silly stuff we're doing today and say it looks like child's play… Jesse Kulp

some highlights:

Stephen previously co-founded Modulz which created Radix UI, now used by Vercel, Linear, and Jetsi.

Now he’s the founder of the most influential design tool on the market — Paper.

In this episode, Stephen gives us a look at how Paper is fundamentally changing the speed of traditional design flows.

Some highlights:

A year ago, it felt like AI-generated UI was about to have its moment. But now the landscape looks a LOT different than what people expected.

So this episode answers the question "what's next?"

Because there's still an untapped opportunity that I believe will become very real soon...

This week, Zach Leach (Head of Design at Gamma) gives a behind-the-scenes of what it’s like designing one of the hottest AI products in the world today.

He shares a ton of techniques and lessons learned from working with LLMs—including some ways to make AI fun again :) And we also learn what makes design at Gamma a bit unorthodox in all the best ways.

Some highlights:

The more I study today's top design teams, the more clear it’s becoming that we're entering the era of a new type of design leader— one with taste and the skills necessary to uphold craft.

So this episode studies this new archetype of leader by highlighting clips from design leaders at Airbnb, Ramp, Duolingo, and more…

Mig Reyes is the VP of Product Experience at Duolingo (and a design director at Instagram before that).

In this episode he shared a behind-the-scenes of how design operates at Duolingo (as well as some harsh truths designers need to hear).

I talk to a lot of designers at the pinnacle of their career…

So I’m always trying to figure out how they’ve evolved the way they practice design over the years.

Once I hear the same answer from a few different people I start to pay attention 👀

So here are a few trends I’m noticing for how the best designers get alignment on their teams.

Anthropic has quickly become a category-defining company and in this episode Kyle Turman (their first full-time designer) shares a behind-the-scenes of what it was like designing Claude.

If you’re interested in startups, AI products, or the art of prompting then this conversation will be right up your alley.

Some highlights:

There's a parallel I'm noticing between what's happening today with AI and what happened way back in 2013.

So this episode studies the early days of Snapchat, the emergence of high-fidelity prototyping tools, and answers the question “what does it look like to have agency in 2025?”

Tuhin Kumar has designed at some of the most prolific companies in the world (early Facebook, Airbnb and Apple).

But everything’s changing in his new role…

Because now he’s the Head of Design at Luma AI which is one of the companies leading the charge on generative AI.

So this episode goes deep on how the value prop of design is shifting.

Some highlights:

There are two goals that designers almost always group together:

But my interview with Sam Stephenson changed my thinking completely 👀

So this episode breaks down Granola’s go-to-market strategy and why I’m copying it for my own startup.

Jack Brody joined Snapchat as one of the early designers where he spent 10 years and eventually became Head of Product.

So this week’s episode features a lot of lessons learned from the early design team at Snap and an inside look at what makes their culture so special.

But we also go deep into Jack’s new role as the Chief Product Officer at Suno where he’s helping design the future of music. So we end up having quite the discussion on creative launchpads and the impact of AI.

Some highlights:

I’ve interviewed a lot of designers who have landed some pretty high profile roles and I’m starting to notice some trends 👀

So this video breaks down 6 portfolio tips that you can use to stand out.

Lovable has quickly become the go-to way I build my ideas with AI and this week we get to hear from their first designer Nad Chishtie.

We go deep into what it takes to succeed as a founding designer and all of the ways AI is shaping modern product teams.

Some highlights:

My #1 source of imposter syndrome is when I see designers prototyping beautiful interactions like this or even this.

It’s one thing to create gorgeous interfaces, but crafting complex interactions from first principles is designing on expert mode. And it’s a big reason why Linear lists interactions as a requirement three separate times in their job description for principal designer.

So this week’s episode is all about how to unlock the skill of interaction design 👇

I use Granola every single day and it’s quickly become a beloved product in the tech community.

But it was a winding journey to get there…

So in this episode their co-founder and designer, Sam Stephenson, gives a behind-the-scenes of what it was like going 0 → 1 with Granola:

I’ve spent a lot of time studying how the best design teams operate and two of my favorites are Ramp and Plaid.

So this episode shines a light on specific practices they put in place to create a culture of craft 👇

What do Raycast, Daylight, Amo, The Browser Co, and Mainframe all have in common?

They all hired Ellis Hamburger to help tell their story.

So this episode is a bit different...

We're going to get away from the pixels and go deep into how you can use language to tell a compelling story about your product.

Some highlights:

AI introduces an opportunity for all kinds of novel interaction patterns.

But it creates a whole new category of design challenges too…

And this episode breaks down the biggest challenge of all.

This week’s episode is with Alejandro Matamala Ortiz, the cofounder and Chief Design Officer at Runway—one of the leading generative AI companies in the world today.

The way they work is incredibly unique. So a big focus of this interview is digging into how AI is shifting the way products get built and what it all means for designers:

Most designers fall into the same trap when presenting their ideas.

So this ~5 min episode breaks down how to pitch your designs like a pro.

This week’s episode is with Christophe Tauziet who is the Head of Design at Plaid—one of today’s leading fintech companies.

We go deep into the ways he’s building a culture of craft and the rituals they’ve evolved to consistently sweat the details. There are a lot of practical processes and ideas in this episode.

Some highlights:

You can have the greatest design concepts in the world, but none of that matters if they don't make it into production.

So this episode is all about how to create an aura of inevitability around your ideas.

It features stories from early Facebook, Webflow, and Figma 👇

Palantir is one of the most powerful products in existence today.

It provides critical government and enterprise infrastructure from the factory floors to the front lines. You can literally build your own Airbnb on top of their development platform.

But with great power comes lots of complexity… So in this week’s episode, Design Lead Aashman Goghari gives us a behind-the-scenes of what it’s like designing products at Palantir.

Palantir is one of the most powerful products in existence today.

It provides critical government and enterprise infrastructure from the factory floors to the front lines. You can literally build your own Airbnb on top of their development platform.

But with great power comes lots of complexity… So in this week’s episode, Design Lead Aashman Goghari gives us a behind-the-scenes of what it’s like designing products at Palantir.

When comes to brand design, Mike and Cara from Smith & Diction are pretty much top of the game (you might recognize them as the ones who did the brand identity for Perplexity).

During our interview, it didn't take me long to realize that these two have more hacks and mental models for creativity than just about anyone I’ve met.

So here are a few of my favorites.

Watch the full episode with Smith & Diction here: https://www.dive.club/deep-dives/smith-diction

If you asked me “who has the best taste in design right now?” one of the first people I’d mention is Thiago Costa.

His product Fey is in the S-tier of design and I’ve studied his visual techniques for many years.

Finally, after over a 12 months of pestering he agreed to share his secrets in a interview 🙌

We go deep into:

Today we get to hear from Ammaar Reshi who is the Head of Design at ElevenLabs—the AI audio platform that has come up multiple times in past episodes.

So a big focus of this conversation is learning what it's like designing an AI-native product. We go deep into topics like:

How do designers from today’s top teams collaborate with engineers?

After many interviews I'm starting to notice a trend…

The highest functioning product teams throw away a lot of code and it’s a good model for what the new “handoff” process will look like. So this video highlights how it works at teams like Figma, Vercel, Perplexity, Airbnb, and more.

This week's episode is with Chris Abad who has led design teams at companies like Google, Square and Dropbox so needless to say he's given a lot of design presentations over his 20+ year career.

So this conversation is a deep dive into storytelling and everything you can do as a designer to effectively share your vision and persuade stakeholders.

He shares every step of his process including a ton of practical tactics like:

Systems thinking is often mentioned as the #1 trait teams are looking for in designers.

But what does it look like to be great at it?

This episode answers that question by highlighting stories from Notion, Anthropic, and more 👇

This week's episode is with Anthony Menecola who is a longtime staff product designer at Shopify so we’re going to do a deep dive into ways you can make a bigger impact at your company as an IC.

One of the big themes of this episode is Anthony’s journey becoming more technical and contributing to the Shopify code base so if you’re interested in building your ideas I think you’ll get a lot out of this one.

We also talk about:

When I say high stakes design project, what comes to mind?

How about Ryan Scott redesigning the Airbnb checkout flow right before a  $3.5 billion IPO? Now THAT is a big time project…

So this episode is all about tactics you can use to make big ideas happen at your company (even as an IC).

And if you want to go even deeper you can use these links to get $100 off Ryan Scott’s top rated Maven courses 👇

1️⃣ Describing the ROI of Design (https://join.dive.club/ryan-scott-roi-course)

2️⃣ PM Masterclass for Designers (ht...

What does it take to create a product worthy of winning Mac app of the year?

I interviewed the founder of Craft Docs, Balint Orosz, to find out…

So this episode is a deep dive into how they work and what it takes to achieve this level of design excellence, including:

I’ve interviewed a lot of staff designers to figure out what it takes to have real influence at companies like Shopify, Github, Airbnb, etc.

One thing is clear… if you want to make strategic impact as a designer then you have to get to a place of altitude that allows you to see the bigger picture.

This episode is designed to help you do just that.

How do the best staff designers influence and lead as individual contributors?

I interviewed Catt Small to answer that question and it turned into one of the most practical episodes yet. She pulls from her 14+ years of experience designing products like Etsy, Asana, and Soundcloud to share techniques you can use to level up your influence and scale your impact as an IC.

Some highlights:

What are the best teams looking for in design candidates?

That’s become one of my favorite questions to ask so this episode shines a light on some of those traits and what you can do to stand out.

It includes insights from:

This week’s episode is with Tyler Angert who was the first design hire at Replit. So we get a behind-the-scenes look at what it’s like designing for a hyper growth startup. However in early 2024, Tyler left to pursue a startup of his own, so a good chunk of this discussion focuses on his vision for Patina and the future of “spontaneous software”.

Some highlights:

I’m designing a new product and a few months ago I would’ve confidently said it’s not an AI product. But I was wrong.

This new technology creates endless opportunities… we just have to be able to see what AI makes possible. And that’s what this episode is all about.

I’ve followed Mike Smith ever since he designed the Perplexity brand identity and quickly realized he’s one of the most creative designers I’ve ever seen. Turns out his wife Chara is a positioning mastermind too so it makes sense why Smith & Diction is one of the hottest agencies in the game today.

So this week’s episode is a deep dive into brand strategy and what it takes to stand out in 2025 and beyond. We get into:

Being able to think like an engineer helps you collaborate with developers more effectively, design UIs that make sense, and empowers you to build your ideas with AI tools like v0, Claude, etc.

So this video is going to break down a few traits of designers who I believe are already doing this at a high level.

It includes insights from:

We've heard a lot on this show about designers becoming builders using tools like v0 and today we get to do a deep dive with Pranathi Peri who is leading the design of v0 at Vercel. We discuss:

Craft is so much more than a shimmering landing page or micro animation…

It’s sweating all of the tiny details and having a thorough understanding of the edge cases in your product.

But there’s one detail most designers miss… 👀

So this episode highlights one of my favorite ideas ever shared on the show from Raphael Schaad (founder of Cron and now the Head of Calendar at Notion).

It’s a fantastic example of what it looks like to obsess over the craft of your product

You can find his full...

This week's episode is with Sam Peitz who quickly became one of my favorite designers to follow in 2024.

He regularly shares experiments like TextOS, his scribble running app, and assorted letter prototypes. So this conversation is a deep dive into his creative process and how he’s redefined his career path over the past ~10 months. We go deep into:

Designers have become servants of “the process” so this episode features stories of people who are breaking the mold in the way they explore and prototype ideas.

It includes insights from:

Gabe Valdivia (Fractional design leader): https://www.dive.club/deep-dives/gabe-valdivia

Dennis Muller (Designer + founder of Amie):

https://www.dive.club/deep-dives/dennis-muller

Gavin Nelson (Designing Linear mobile app):

https://www.dive.club/deep-dives/gavin-nelson

Nikolas Klein (Designing Prototyping at Figma):

https://www.dive.club/deep-dives/figma-prototyping

Michael Wandelmaier (Former Head...

Did you know that the very first interface designer at Adobe was also the first designer to work on Figma? 🤯

His name is Andrei Herasimchuk and he knows a lot about design tooling…

So this week’s episode is jam-packed with stories about designing the earliest interfaces for Illustrator and Photoshop, as well as what it was like seeing the original seed of an idea that became Figma.

Not only that… Andrei gives us a behind-the-scenes of his new design tooling startup and shares his vision for where software creation is headed next 👀

Some hi...

Many of my favorite episodes are when we get to hear from the earliest designers at companies like Linear, Perplexity, Ramp, Facebook, etc.

So this episode pulls out the key insights so you can learn what it takes to thrive as a startup designer:

Imagine joining an early stage startup as the first senior designer and within a few years, it becomes the fastest growing company ever.

Well… that's the story of Diego Zaks who is now the VP of design at Ramp.

This week’s episode is all about how they were able to win with design and what makes their culture so special. We go deep into:

Imagine you’re asked to lead the design of a new project. It’s complex, open-ended, and full of interconnected problems…

How do you attack that ambiguity and get momentum quickly?

This episode is an attempt to answer that question by unpacking tactics used by designers like:

2024 was the year the Perplexity brand took over the design community. And a big reason why is because of Phi Hoang.

So this week’s episode is a deep dive into brand experience design and creativity with AI tools. We get an inside look at:

It doesn’t matter how good your designs are if they never get built. So this episode breaks down specific tactics you can use to become a better storyteller and get people excited to build your ideas.

Michael Wandelmaier (former Head of Design at Metalab): https://www.dive.club/deep-dives/michael-wandelmaier

Gavin Nelson (designing the Linear mobile app): https://www.dive.club/deep-dives/gavin-nelson

Ian Wharton (storytelling coach): https://www.dive.club/deep-dives/ian-wharton

Kathy Zheng (head of design at Optimism): https://www.dive.club/deep-dives/kathy-zheng

Yuan Wang (he...

A little over a year ago, Joey Banks and I were DM’ing each other in Slack about leaving our W-2 jobs and going independent.

So this week’s episode is a reflection on his journey working for himself and it’s as human and relatable as any conversation I’ve ever had on this show. We go deep into:

The pendulum has swung too far with design systems. Somehow they’ve become synonymous with scale. But I believe they’re the perfect first step for startups. So this episode looks at stories from Perplexity and Cron to reframe design systems as the key to speed in the early days.

Henry Modisett (Head of Design at Perplexity): https://www.dive.club/deep-dives/henry-modisett

Raphael Schaad (founder of Cron / Notion Calendar): https://www.dive.club/deep-dives/raphael-schaad

Brad Frost (author of Atomic Design): https://www.dive.club/deep-dives/brad-frost

After writing a viral article called “The Missing Tool” I was fortunate to meet Gab and Nim who are the co-founders of a startup called Dessn.

Dessn is a new way to ship design changes without having to write code. Their extension overlays a Figma-like interface on your live web app so designers can easily make changes. Their AI then writes the code and pushes it to your Github. That means designers can now contribute directly to production.

Over the last few months we’ve had regular jam sessions about the future of design tooling, how AI...

Over the last few months, I’ve interviewed the people designing cutting edge AI products like Perplexity, Claude, Dot, Humane, Visual Electric, and more…

During that time I’ve created a running list of all the metaphors and mental models they’ve used to explain what it’s like.

So this episode breaks down 7 mental models for designing AI products.

Maggie Appleton (Design engineer at Normally): https://www.dive.club/deep-dives/maggie-appleton

Henry Modisett (Head of Design at Perplexity): https://www.dive.club/deep-dives/henry-modisett Joel Lewenstein (Head of Product De...

One of the most impressive things I’ve seen a designer make all year is Meng To’s Dreamcut.

It’s the perfect example of what it looks like to transition from traditional designer to builder 💪 So if you’re interested in becoming a designer who ships then this is the episode for you.

Meng gives a highly practical breakdown of what it looks like to go from 0 to 50,000+ lines of code as a designer. And Meng is the perfect person to onboard you into tools like Claude and Cursor because he’s spent 10+ years teaching desi...

Airbnb is making 3 big design investments to bring soul back to the app. So this episode pulls from interviews with their VP of Design, Teo Connor, and prototyping specialist Janum Trivedi. Learn why Airbnb is investing in 3D, motion design, and leaders who still have their hands in the clay.

Teo Connor (VP of Design at Airbnb): https://www.dive.club/deep-dives/air-bnb

Alex Schleifer (former Chief Design Offer at Airbnb): https://www.dive.club/deep-dives/alex-schleifer

Janum Trivedi (prototyping specialist at Airbnb): https://www.dive.club/deep-dives/janum-trivedi

As soon as I finished our original interview, I knew I had to have Soleio on as the first repeat guest. He led early design efforts at Facebook and Dropbox. Now he invests in design-driven startups like Figma, Framer, Vercel, etc.

So this week’s episode is all about how designers and startups can succeed in a world where everything is changing. We go deep into:

This week’s episode is with Joel Lewenstein who is the Head of Product Design at Anthropic where he works on cutting edge AI products like Claude. After 80+ episodes, I can honestly say this one’s “juice per minute” score is off the charts.

Some of my favorite highlights:

Airbnb is one of the truly iconic design-driven companies. They set the bar for design innovation in so many ways. So this week’s episode is a deep dive with their VP of Design, Teo Connor.

She gives us a behind-the-scenes look at how design operates at Airbnb including: