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
The podcast Dive Club 🤿 is created by Ridd. The podcast and the artwork on this page are embedded on this page using the public podcast feed (RSS).
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:
If you liked this episode then you’ll enjoy the interview with Colin Dunn (co-founder and designer of Visual Electric)
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:
Brian Lovin’s article “Teams should work with the garage door up”
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.
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:
⭐ Don’t forget you can also save $100 on Chris’s Design Storytelling course using the code DIVECLUB
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 (https://join.dive.club/ryan-pm-masterclass-course)
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:
Introducing Craft 3
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 episode here — https://www.dive.club/deep-dives/raphael-schaad
And this episode also pulls in part of my conversation with Julius Tarng about his time at Linear — https://www.dive.club/deep-dives/julius-tarng
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 of Design at Metalab): https://www.dive.club/deep-dives/michael-wandelmaier
And lastly it features insights from Jenny Wen including her original blog post that inspired this episode (definitely bookmark this it’s awesome)👇
https://jennywen.substack.com/p/dont-trust-the-design-process
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 highlights to expect:
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:
Want to work with Diego at Ramp? They’re hiring ✌️
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:
Jenny Wen’s Eigenquestions Figjam template
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 (head of design at Maven): https://www.dive.club/deep-dives/yuan-wang
Alex Cornell (design lead for Gen AI at Meta): https://www.dive.club/deep-dives/alex-cornell
Noam Segal (senior research leader): https://www.dive.club/deep-dives/noam-segal
Femke (design lead at Gusto): https://www.dive.club/deep-dives/femke
Gabe Valdivia (independent designer): https://www.dive.club/deep-dives/gabe-valdivia
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
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 impacts software creation, and everything in between…
These jam sessions have been some of the most inspiring conversations I’ve had this year. So this week’s episode is a way to loop you in on some of those conversations. We go deep into:
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 Design at Anthropic): https://www.dive.club/deep-dives/joel-lewenstein George Kedenburg III (Designer at Humane): https://www.dive.club/deep-dives/george-kedenburg-iii Colin Dunn (Co-founder of Visual Electric): https://www.dive.club/deep-dives/colin-dunn Jason Yuan (Co-founder of Dot): https://www.dive.club/deep-dives/jason-yuan
Chapters 0:00 AI as an organism we grew 1:49 AI as the middle of a field 6:24 AI as a chef in a kitchen 7:37 AI as a new child 8:42 AI as a new material 10:20 AI as the meat of our design deliverable 12:11 AI as electricity
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 designers how to code through Design+Code. So in this episode we go deep into:
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:
Chapters 0:00 Intro 1:32 Designers who can ship 11:18 Dealing with the velocity of tech as an investor 13:27 The importance of brand for startups 18:00 Why Soleio beleives we won't be using smartphones the same way in 5 years 34:23 Qualities that Soleio looks for in first-time founders 36:58 How to succeed as a founding designer 44:53 Founders living in the future 55:05 How to invest in your future founder journey today
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:
Imagine your first traditional “product design” job is designing the Snapchat messaging UX for millions of people across the globe…
Well that’s what Dan Moreno’s journey looked like as an engineer turned designer.
So this week’s episode is a deep dive into his 5+ years designing Snapchat as well as his new role at a rocket ship startup called Captions.
Some highlights:
I remember the exact moment where I first explored MercuryOS. It was clear Jason Yuan was one of the most skilled design thinkers I'd ever encountered. No wonder he landed a role designing AI products at Apple shortly after.
But the main reason I wanted to interview him was to learn more about his new product called Dot. It's by far my favorite personal AI and a beautifully designed experience. So this conversation is a behind-the-scenes of his latest journey and a fun glimpse at what the future might hold for software products. We go deep into:
Mariana Castilho has one of the most impressive career trajectories of any designer I’ve ever met.
I first saw her while mentoring through Shift Nudge and within a few years she’s landed roles at Universe, Vercel, and most recently as the first designer at Pierre.
One of the keys to her growth has been investing in her skills as an engineer. So a big part of this interview is learning what it takes to transition from designer to builder.
Some highlights:
This week’s episode is with Janum Trivedi who makes some of the most stunning prototypes in all of design. So the main goal of this conversation is to answer the question “what makes a piece of software feel great?”
Some of the key talking points:
Ben Blumenrose was one of the earliest designers at Facebook and has spent the last 12 years as a co-founder and Managing Partner of Designer Fund. That’s allowed him to invest in many of the design founders that you’ve heard from on this shown (like Jorn from Framer or Colin from Visual Electric).
So the goal of this conversation is to tap into Ben’s perspective as a designer turned investor. This episode creates a blueprint for people interested in designing for startups or maybe even building a company of your own.
Some highlights:
Apply for the Designer Fund Partnership program
Imagine leading the design of an AI product that skyrockets to a billion+ dollar valuation in under two years…
That’s the story of Perplexity and today we get to hear from their founding designer and current Head of Design, Henry Modisett. Some of the highlights from this conversation:
SHOW NOTES
KEY TAKEAWAYS
Starting with a design system
Before Henry had any idea what the Perplexity product would become, he built a component system in React as the first step. The goal was to give himself a toolbox to make it easy to assemble new features. Many components are obvious (ex: you know you’ll need a grid, type system, color system, buttons, etc.). We don’t have to overcomplicate design systems. They’re the thing you invest in to move fast… not the thing you invest in once you have most of the interface figured out.
Empowerment through code
When you write code, you develop a stronger emotional attachment to the product. You’re also empowered to continually make improvements without having to go through engineers. The more removed you are from what ships, the easier it is to dish blame on someone else for an experience being janky.
“Having designers that can code is a hack…quality just happens”
Velocity is everything
Henry makes a point to prioritize velocity over exploration, debate, visual design, etc. And a big part of what makes that possible is empowering designers to make decisions. If it’s a UX question, the designer needs to make a call (”go with your gut and if you want to change it later you can”). This is also why having designers who can code is key. Nothing is cemented. You don’t need permission to iterate after something ships.
Dynamic UI systems
At the root of Perplexity are UI systems that display dynamic content based on what the user searches. That means as a designer you can’t possibly mock up all use cases. You have to think about interfaces as slightly abstracted (ex: “entity comparison” which can work for comparing dog breeds, restaurants, etc.). Part of designing a dynamic system is you have to be ok with percentage outcomes. Sometimes the formatting isn’t going to be perfect.
You’re designing the system, giving AI the tools to use, and hoping that it works most of the time.
This week's episode is with Ryan Scott who was an early designer at Doordash and then spent years as a design lead at Airbnb. Nowadays Ryan teaches hundreds of designers ranging from seniors to VPs how to make a bigger impact at your company.
This episode is jam-packed with insights about:
Investing in my personal brand has been the best investment I’ve ever made in my career. So I wanted to find the perfect designer to give a personal branding masterclass and I think it’s Oliur.
He’s built a massive audience across YouTube, Instagram, Twitter, etc. and he shares his hard-earned knowledge in this episode:
This week’s episode is with Maheen Sohail who is a senior staff designer working on generative at Meta. She joined as one of the earliest designers on both the VR and AI teams, so a big part of this discussion is about navigating ambiguity when there’s no clear playbook to follow.
We go deep into:
⭐ KEY TAKEAWAYS
Nobody knows what they’re doing
This is especially true when you’re designing products for emerging technologies like AI. It’s easy to look at people working on these AI-native products and assume they have it all figured out… but we’re all still learning and exploring what’s possible. This came up in George Kedenburg’s episode too.
Curiosity > everything
I asked Maheen what traits are more important than curiosity for people interested in designing AI products. Her answer? Nothing.
The importance of passion projects
There’s a trend I’m noticing in these interviews… the designers who are creating cutting edge use cases for AI are the ones actively exploring the technology with side projects. Reading essays isn’t the way to learn. You have to want something to exist in the world and use that as a reason to figure out what’s possible. For Maheen it was using AI models to colorize images of Pakistan. For Nate Parrott it was using AI to hallucinate in HTML.
After 8 years designing at Meta, George Kedenburg III pulled a 180 and joined Humane as a design lead. So this conversation is a deep dive into designing AI products and how the role of product designer evolves in an AI-native company:
Pushing past the pixels
The real value of design is being able to look at an ambiguous situation and understand what you should explore.
Rectangles so happen to be the most common way to express that value. But the real skill is creative problem solving.
Working at a company like Humane forces designers to contribute design thinking beyond the pixels.
Prompt design > prompt engineering
If the AI model is a chef, then you’re responsible for designing the kitchen.
You don’t know what the user will order, so it’s a lot of trial and error to ensure you have the right data on hand at the right moments.
It’s no different than thinking through drop-off in an onboarding flow. Which is why George views working with these models as “prompt design” rather than “prompt engineering”
There are no AI edge cases
When you’re prototyping AI products, your prototypes don’t “break” or “fall over” like they do in Figma. That’s because the boundaries of what exists in the prototype become much blurrier.
Instead of designing contained flows, you’re laying a foundation and allowing the model to extrapolate out from there. There are no more hard edges.
George mentions Claude Artifacts as an example of someone putting the pieces together in the right order
Visual Electric has quickly become my go-to product for image generation and in this week’s episode we get to learn from the founder and designer, Colin Dunn. The whole discussion is an excellent look at the design founder journey as well as a deep dive into AI-native creative tools. We get into the weeds about:
Key takeaways:
The Arc browser is one of the best products I’ve downloaded in the last few years which is why I’m so excited about this interview with their founding designer, Nate Parrott.
This conversation, we get an inside look at what makes design at the Browser Company so unique. We discuss:
This week’s episode is with Dan LaCivita who is a co-founder of Play—a new way to design mobile apps using native iOS materials. As soon as I saw this app clip I knew it was a big deal and that I had to interview him to learn more.
So in this conversation we go deep into:
Gavin Nelson is currently designing the Linear mobile app in addition to the best app icons on the internet. So this episode is a deep dive into prototyping and interaction design:
If you watched last week’s episode, then you heard Jordan Singer say how visual search was actually the “killer feature” (not generative AI). What’s interesting is that this feature was actually a mid-project pivot.
So in this episode we get the full behind-the-scenes of visual search from design engineer Vincent van der Meulen:
Live from Config, this episode with Jordan Singer follows his journey from the Diagram acquisition all the way to Figma’s 2024 AI release. We go deep into:
This week’s episode is with Kathy Zheng who is currently the Head of design at a Web3 protocol called Optimism. But before that she was the first designer at Patreon and went on to spend over 6 years at Github.
So the goal of this conversation is to look at how Kathy grew as a designer while at Github and identify the specific milestones on her journey to reaching senior and eventually staff designer.
We get into the weeds about:
Some of the people mentioned in this episode:
When you think about storytelling in design... Alex Cornell is often the person that comes to mind. And that's a big reason why he's one of the most requested guests on the show. So this episode is a deep dive into the finer details of communication. We talk about:
Remember how Michael Wandelmeier told us Metalab hired a storytelling coach? Well that coach is Ian Wharton. He’s an Apple Design Award winner, CEO of Aide Health, and he teaches storytelling techniques to teams like Dyson, BBC, Huge, etc.
So this episode breaks down the key storytelling concepts that he shares in his course Sell the Idea. We talk about the importance of the inciting incident, how to empower others to share your ideas, and a lot more…
But he also presents some compelling ideas about why designers are the most suited people to start companies that solve societal level challenges. All you need is a bias toward action. So if you’ve been considering starting your own thing, there’s a lot we can learn from Ian’s journey as a design founder.
~6 months ago Amy Lima was laid off and has been preparing for this episode ever since. So in this interview she gives us an inside look at her process for landing a dream role at Duolingo. If you’re looking for your next role then this conversation is quite the playbook. She has the job hunt process down to a science.
Some topics covered:
Show notes:
Sponsors:
So this conversation is a deep dive into what it looks like for designers to approach their work with an engineering mindset. We talk about Julius’s deep background in prototyping, how he collaborates with designers at Linear. And we also get into why the current state of design engineering is a missed opportunity.
If you’re looking to grow as a software designer then you’ll love this episode.
Show notes:
When it comes to design founder stories, Raphael Schaad’s is one of the best. So this episode is the first-ever telling of how Raphael designed and built Cron (which became Notion Calendar). We talk about:
Alex Schleifer was the long-time Chief Design Officer at Airbnb where he grew the team from ~35 to over 600 people. So this conversation is an inside look at what makes design at Airbnb so special. We discuss:
Alex’s “People vs. Algorithms” podcast
Mentioned Airbnb alumni:
Helen Tran was an early designer at Shopify and is now leading product design at AngelList. But in between those two roles she also ran her own startup for three years. So the goal of this conversation is to figure out how that period of time impacted her design practice so we can all learn how to design with a founder’s mindset. In this episode we discuss:
- How Helen is approaching design leadership differently this time around
- How Helen constructors hypotheses to influence product strategy
- Why Helen made sacrifices to her production skills
- The keys to designing in a pre-PMF company
- The #1 way to help founders
- + a lot more
Helen’s website - https://helentran.com/
Dive is where the best designers never stop learning 🤿
🌐 dive.club 🐦 twitter.com/joindiveclub N
ow you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
Today we're talking with designer and entrepreneur, Hunter Hammonds, who has grown 5 different agencies to millions in revenue in less than a year. So in this episode we walk through the different stages of building an independent design business—starting from positioning yourself as a solopreneur all the way to scaling operations to 7 figures. We get into the weeds about:
- Hunter’s framework for selling yourself on a landing page
- The tactics OffMenu uses to convert more leads to customers
- Why Hunter thinks MRR is a misguided metric
- What operational fat you can trim to increase margins
- How you can improve your sales calls
- + a lot more
- Petr Knoll - https://twitter.com/iampetrknoll (design partner OffMenu)
- Christian O’Brian - https://www.linkedin.com/in/obrienchristian/ (CEO OffMenu)
- Sahil Bloom - https://twitter.com/SahilBloom (partner OffMenu)
- Agencies
- Instrument - https://www.instrument.com/
- Basic - https://www.basicagency.com/
Dive is where the best designers never stop learning 🤿
Ready for a masterclass in positioning? Nick Pattison has been working for himself for well over 10 years... but recently he's laser-focused on running 1-week brand sprints (and it's working). So this episode is a deep dive into his new freelance playbook:
- The automations that allow him to focus on sales and creative direction
- Lessons learned from running 25+ brand sprints at $15k each
- How Nick focuses on growing his creative muscles
- His strategies for presenting work to clients
- Why he stopped writing proposals
- + a lot more…
- Nick’s agency: Primary Studio - https://primary.studio/
- Nick’s talent company: Stellar - https://www.stellar.work/
- Nick’s Twitter - https://twitter.com/thenickpattison
Dive is where the best designers never stop learning 🤿
This episode is the ultimate design founder story. Dennis shares all of the ups and downs along his journey to build Amie—a new productivity tool that captures your emails, calendar, and to-dos in a single beautiful product. Some of the highlights:
- Where Dennis draws inspiration
- The traits Dennis looked for in early hires
- What Dennis looks for in design candidates
- The backstory behind Amie’s viral website launch
- How Dennis balances his intuition with product feedback
- How Dennis thinks about innovating vs. capitalizing on familiarity
- Things 3 app - https://culturedcode.com/things/
- Stefan - https://twitter.com/_animify the Amie design engineer
- Devin - https://www.cognition-labs.com/introducing-devin—AI coder
- Brian Chesky interview - https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach on Lenny’s Podcast
- The Amo app - https://amo.co/
- Dennis’s custom Amie pants - https://pbs.twimg.com/media/GEoOIsjW0AUYiTj?format=jpg&name=900x900
Dive is where the best designers never stop learning 🤿
🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
Over the last few months, design engineering has by far been the #1 most requested topic. So I wanted to get the inside scoop from the team at Vercel to learn more. In this episode we get to hear from:
1. Glenn Hitchcock - https://twitter.com/glennui (Director of design engineering)
2. John Pham - https://twitter.com/JohnPhamous (Lead design engineer)
The goal of this conversation is to help people understand the role that design engineers play and to outline a path you can take to develop some of these skills. We talk about:
- The strategy behind Vercel’s new website
- Why Vercel built a design engineering team
- How designers collaborate with design engineers
- What Vercel looks for when hiring design engineers
- How Vercel is always building with re-usability in mind
- + a lot more - Maggie Appleton’s quote on software creation from our group interview
- https://anthonyhobday.com/blog/20240122.html
- Framer components - https://drams.framer.website/ (inspired by Dieter Rams’ design principles)
- Screwball scramble - https://us.tomy.com/screwball-scramble/
- Dead Simple Sites - https://deadsimplesites.com/
Dive is where the best designers never stop learning 🤿
🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
Since the beginning of my design career, I’ve looked up to Metalab. So this interview is a special one because we get to learn from their Head of Design, Michael Wandelmeier. We go deep into how design works at Metalab and talk about specific strategies around:
- Mike’s go-to storytelling tactics
- The importance of opinionated design
- When they ignore constraints on a project
- The unique way they map out user journeys
- Tips for driving alignment on complex projects
- How they use the “ridiculously early hypothesis”
Dive is where the best designers never stop learning 🤿
🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
One of the tools I'm most interested in right now is Relume. 200k+ people are using it to design and build websites faster with AI. They have a massive set of Figma/Webflow components which allows them to take a unique approach that “respects the process” of web design. In this bonus episode, their co-founder Adam gives us an end-to-end demo where he sitemaps, wireframes, designs, and builds a full website in ~30 min. We then get into the weeds about:
- How the web design process will evolve with AI
- What this means for the role of designer
- His journey as a design founder adapting to AI
- Where Relume is headed next as a company
👀 Dive is where the best designers never stop learning 🤿
- Relume’s Figma library - https://www.relume.io/figma-library
- Relume’s Webflow library - https://www.relume.io/components
- Galileo - https://www.usegalileo.ai/explore (another AI tool we mentioned)
🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
Rich Arnold was the Head of Design at Vine, a design lead on the early Instagram Stories team, and now he works as a design manager at Coinbase. So this episode goes deep into:
- How Rich grew as a storyteller at IG
- Why we cant let data be the designer
- The importance of “zooming out” in your work
- How to grow your creative problem solving muscles
- What it takes to design successful consumer products
- Ian Spalter (Old Head of Design at Instagram) - https://www.linkedin.com/in/ianspalter/
- Rus Yusupov (Cofounder of Vine and HQ Trivia) - https://en.wikipedia.org/wiki/Rus_Yusupov#:~:text=Rus%20Yusupov%20(born%20May%204,and%20CEO%20of%20HQ%20Trivia.
- Lapse (Mobile App) - https://www.lapse.com/)
If you’ve dabbled in design systems then you’re no doubt familiar with Brad Frost and atomic design. He’s laid the foundation for design systems teams around the world. So in this discussion we talk about the types of challenges he faces at Big Medium and how he’s envisioning the future of design systems:
One of the most requested guests has been Gabe Valdivia. He was an early designer at Facebook, a designer manager at Google, and has led design for different startups over the years most recently as the head of design for Patreon. But in the last year he's made the jump to start his own practice and position himself as a fractional design partner for early stage teams. So a lot of this conversation gets into the weeds about what it's like to design 0 to 1 experiences. We talk about tactics for speed, storytelling, prototyping and a lot more...
Dive is where the best designers never stop learning 🤿
As soon as I read No More Boring Apps I was hooked. Andy Allen immediately became one of my design heroes and now I use his Not Boring apps daily. So this conversation is a behind-the-scenes of his journey, an analysis of the state of software design, and a glimpse of where we’re headed next as an industry. Some highlights:
- The design tools Andy is most excited about
- Andy’s advice for people wanting to learn 3D
- The differences between good and great design
- The 4 things needed for design to have cultural impact
- How AI will empower us to deliver tailored software at scale
- Why the future of design tooling might mirror the game industry
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
In this episode we get to hear from Jenny Wen who is the person who originally designed and brought Figjam to market. This conversation is full of inslights like:
This episode expands on 8 key insights that I took away from interviewing designers like Soleio, Kevin Twohy, Molly Hellmuth, Soren Iverson, etc.
1. A unique way to stand out as a design candidate
2. How to grow as a vision caster
3. The question every freelancer should ask clients
4. The curse of knowledge in web design
5. When systems thinking is most important
6. Strategies for Figma variables
7. The Craft Flywheel
8. How to know which details matter
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
Soleio made a name for himself as the 2nd design hire at Facebook and eventually went on to lead design at Dropbox. Now he invests in extraordinary software startups like Figma, Framer, Vercel, Perplexity, Replit, Universe, tldraw, and dozens more worldwide. So in this discussion we go deep into:
- The fascinating story behind project Motion
- How Soleio’s skillset evolved during his time at Facebook
- When it makes sense to invest in craft (and when it doesn’t)
- what Soleio looks for when hiring designers
- How startups can attract the top design talent
- Why Soleio is so excited about spatial computing
- The type of companies Soleio is looking to invest in next
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
Galileo recently broke design twitter with the launch of their new generative AI tool for builders. So in this episode we talk with their co-founder and lead designer, Helen Zhou about:
- Her journey as a design founder
- Why user research for AI tooling is unique
- How AI will change the day-to-day role of a designer
- Her response to concerns about LLMs and creativity
- The potential breakthrough use case for UI generation
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
Webflow has had as big an impact on design as any company over the last decade. So this episode is an inside look at their design culture, rituals, and key insights from their Head of Design, Kevin Wong. Here’s a preview of some of the ideas we cover:
- How Webflow executed a massive rebrand leading up to their conference
- The different types of prototypes for driving alignment
- The role of design systems in their latest visual refresh
- How designers can handle situations where stakeholders disagree
- Ways to improve the way you share your work via Loom
- The rituals and processes used by designers at Webflow
- How design casts vision with “north stars”
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
In this episode we get to hear from Ryo Lu who was one of the very first designers at Notion. This conversation is an inside look at the Notion design process, how they think about product, and a lot more:
- How Notion approached the user research process for AI
- Strategies for improving your systems thinking
- How design at Notion sources feedback on meaty problems
- How Notion thinks about their design system
- What Ryo is looking for in your portfolio
- How to operate outside the traditional “design” role
Dive is where the best designers never stop learning
🤿 🌐 dive.club
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
In this episode we’re talking with Molly Hellmuth who is the creator of UI Prep where she has an incredible newsletter, design system, and course where she’s taught hundreds of designers all over the world. This discussion gets into the nerdier side of Figma 🤓 We talk all about:
- When it does and doesn’t make sense to adopt variables
- How to make sure you don’t invest in a Figma strategy that you later regret
- Molly’s favorite Figma plugins for design systems
- How she’s building components differently in V8 of her UI Prep design system
- Her journey as an independent creator
- + a lot more
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
There’s a new design super team emerging at Clerk and in this episode we get a behind-the-scenes from the leader, Derek Briggs. We get into the weeds about:
- How Derek assembled an A-list team from scratch
- Why Derek pushed for a dedicated UI engineering team
- How Clerk is approaching their massive redesign
- Why Derek doesn’t believe in design deadlines - The business case for prioritizing quality - Derek’s #1 piece of advice for younger designers - + a lot more Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
In this episode we get to learn from Tommy Geoco who has launched countless projects, sold a startup, and built an audience of almost a million designers online. This conversation has everything—here’s a little taste of what you can expect:
- The wild story behind Tommy selling his first company
- Why design tools matter more than ever
- How to become better at selling yourself
- Tons of strategies for your next side project
- Tommy’s mental model for learning as a self-taught designer
- Why Tommy doesn’t care about being novel
- Ways to improve your “taste” as a designer
- Why Tommy acquired UX Tools (and his plans for it)
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
This episode looks at Kevin Twohy’s 10+ year journey going from solo freelancer to independent design studio. We cover a LOT including:
- Strategies for cold outreach and pricing
- Tips for getting aligned quickly with clients
- How Kevin gets plugged into a new team
- Why Kevin has started positioning himself as a studio
- A better way to take equity in client projects
- Why you should be wary of starting a productized agency
- + a lot more
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
Lauren LoPrete shares lessons from her experience leading design systems at Dropbox and now at Cash App. We talk about:
- What design systems actually look like at scale
- Why she’s approaching documentation differently at Cash
- Her experience in the Figma variables beta
- Why Lauren is so excited about string variables
- Traits of successful DS designers that we don’t talk about enough
- + a lot more
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
Kate Syuma was the 3rd designer at Miro and went on to become the Head of Growth Design during her 6+ years at the company. This episode is a masterclass in designing for business impact. We discuss:
- Her process for identifying the aha moment in your product
- How Kate overcame imposter syndrome in her first year
- Ways designers can ask better data questions
- Insights from researching onboarding at 80+ companies
- The importance of designing for emotion vs. solving problems
- + a lot more
If you want to learn more about Kate definitely check out: Growthmates - https://katesyuma.substack.com/ ✌️
Dive is where the best designers never stop learning 🤿 🌐 dive.club 🐦 twitter.com/joindiveclub
Now you can join advanced courses taught by the top designers to help you take a huge leap forward in your career 💪
If you’ve opened Twitter in the last year then you’re definitely familiar with Soren Iverson’s satirical designs like Uber Hotbox and the iMessage typing indicator. So in this episode we get an inside look at his process and lessons he’s learned throughout his career:
In this episode, Kathryn Gonzalez walks us through how she built the DoorDash design language as the first designer and frontend engineer. We talk about what it's like designing for a 3-sided marketplace, how to figure out the right level of craft for your product, and get an inside look at how DoorDash structures their design system.
Kathryn spent almost 7 years at DoorDash and eventually became the Head of Design Infrastructure so this episode is chalk full of wisdom ✨
This Deep Dive is a special one because we get to hear from Niko Klein and Garrett Miller from the prototyping team at Figma.
We get a behind-the-scenes look at everything that led up to the advanced prototyping release at Config 2023 as well as:
In 2022, Marco Cornacchia was coming off of a failed startup and started working on his new portfolio. Little did he know this project would land him a role as the founding designer at Diagram, lay the foundation for design Twitter’s most viral website, and spawn a talk at Webflow’s conference 🤯 In this episode, Marco shares how he (accidentally) created a new trend of animated bento grids. And we also get a behind the scenes of what it was like being the founding designer of Diagram and ultimately getting acquired by Figma. If you’re interested in designing at a startup then you’ll love this episode ✌️
This episode is a panel discussion hosted by Maven where we talk about specific strategies that you can use to become more valuable as an individual contributor on your team. We cover a lot of ground including:
In this deep Dive, James gives us a behind-the-scenes of his creative process and how he is reimagining every pixel of the Clerk brand. We get into the weeds of how he establishes visual languages, his approach to animation, and what he looks for in a motif.
We also discuss which design trends are worth jumping on, which ones have peaked, and which ones to avoid. If you're into branding, visual design, or landing page techniques then you'll love this episode.
In this episode, Brian Lovin talks about his journey as a second-time founder and gives a behind-the-scenes of building his new startup, Campsite. He also shares key insights from hundreds of interviews he’s conducted to learn more about what makes a great design process. We talk about: - Strategies for sharing your work and getting feedback - Why Brian thinks we’ve gone too far with landing page design - Finding the right level of craft as a design founder - Why Brian no longer thinks every designers should start a company - The problems with post-COVID design process - What he’s doing differently as a second-time founder - The three values he’s instilling in the design culture at Campsite + a lot more
In this Deep Dive, David Hoang gives us a peek into where he thinks the industry is headed and how product designers can prepare for the future. We talk about:
In this episode, we analyze four different websites (Lemonade, Formcarry, Stella Domo + Runway) to help you confidently write and design landing pages that sell 💪 Listen to learn how to:
If you want to go even deeper 👉 check out Erik's new Landing Page Academy 💻
In this episode we get to go backstage with the design team at Loom! They teach us all about their design process and share takeaways from their recent AI launch including stories about:
- Prototyping and researching early concepts
- Collaborating with engineers and other cross-functional teams
- Using Figjam to gather feedback live
- Developing a visual language for AI
- Documenting edge cases and all the potential user states
- Pivoting mid project 👀
This week's Deep Dive features early-career designer, Perry Wang. Previously at Google and now working at Discord. This Deep Dive is a masterclass for junior designers looking to jumpstart their career. We cover a lot👇
This episode of Deep Dives highlights the 5 things I learned from interviewing designers like Dan Mall, Grace Walker, Adrien Griveau, Yuan Wang, and Luis Ouriach. You'll learn:
1) How to organize variables in Figma and think strategically about primitives vs. semantic tokens
2) How to price yourself as a first-year freelance designer
3) How the best design systems teams operate
4) How to level up your design portfolio and rethink your case studies
5) How to collaborate with engineers like the founding designer at Linear
It’s impossible to overstate the impact that Linear has had on the design world. So you can imagine how excited I was to have the opportunity to learn from their founding designer, Adrien Griveau 🙌
This Deep Dive is an all-access pass to design at Linear including Adrien’s approach to collaborating with the engineering team, the traits that Linear looks for in design candidates and a behind-the-scenes of Linear’s product process.
Enjoy :)
🗣 This interview was special because I got to reconnect with former team member at Maven — Yuan ✌️
Yuan led design at Twitter, Airbnb and Maven and actively coaches creative leaders in the industry ✨
In this interview we talk energy through your career, how we organize our portfolio websites and strategies for presenting work to stakeholders.
Making the jump and diving into that first year of freelancing can be pretty daunting… 🥲
I wish I could’ve had this chat with Grace about 5 years ago because she was very transparent about the lessons she learned in that first year.
In this Deep Dive, she breaks down her strategies for pricing, balancing project work, her tool stack, and a lot more...
If you’re familiar at all with design systems then I definitely don’t need to introduce you to Dan Mall. He’s as OG as it gets.
In this Deep Dive, Dan shares his take on Figma variables, where design systems are headed in the coming years, and a lot more…
Anthony Hobday, a self-taught interface designer, became an expert by obsessively studying the works of top designers around the world. 🌎
Now he is dedicated to bridging the knowledge gap for fellow self-taught designers by sharing every step of his design process.
In this episode, Anthony highlights simple yet effective techniques everyday designers can make to elevate their visual design skills to create a more compelling final product. 🔐
This episode is all about engineer turned designer Grace Ling, who scored her dream job as product designer at EA and is also now the founder of the biggest design community online, Design Buddies. Grace jumpstarted her career by putting herself out there as a content creator and using some unique tactics when applying for roles. In this interview we talk about how Grace fast-tracked her learning journey, her playbook for breaking in to a new company and practicals to stand-out as a designer in today's job market.
If you're looking to level up how you use variables in Figma then this episode is for you ✌️ Luis goes deep into strategies based on team size, provides naming guidance, and even breaks down how he thinks about structuring libraries with variables in Figma. Lastly, Luis shares a behind-the-scenes of his journey as a designer advocate and even gives a unique prediction for how AI will take shape inside of Figma.
Don't forget to follow Luis on Twitter and check out his awesome files in the Figma community
Steph Golik was an early design leader at the self-driving car startup Cruise 🚗 But 2 years ago she left to launch her own company Huddle. In this episode we're talking all about how designers can take the leap to start that next project or even raise venture funding like Steph. If you're interested in entrepreneurship or even just want to get better at selling your ideas... you're going to love this episode. 🧡
Fons was the one who originally designed the Dive brand 🤿 so this episode is a branding masterclass. We walk through a mock project and Fons goes deep into each phase of his branding process. We also discuss spatial computing, how to make you designs stand out, and strategies for leveling up your visuals 😎
In this episode, Charli takes us behind the scenes of her role as Creative Director at ConvertKit. She shares all kinds of insights about brand and marketing strategy, how to tell data stories, and how to level up as a copywriter. If you're looking for creative inspiration or ways to advance your career, then this episode is for you ✌️
If you're looking to level up your storytelling and make a bigger impact on product strategy, then this is the episode for you 💪 Femke shares practical insights from her time at Uber, WealthSimple, and now as a design lead at Gusto. We go deep into strategies for collaborating with PMs, handling pushback in design, and how designers can more effectively sell their ideas.
In this episode, Dan shares his insights on using Framer from his experience as an early adopter. He also discusses his approach to learning to code while building his own product and shares some tips for others looking to do the same. And obviously, we couldn't call it a Deep Dive without chatting a bit about the impact of AI as well as learning how Jay-Z used to influence the product roadmap at TIDAL 👀
In this episode, Mia shares stories and lessons learned from her time as an early design leader at Square and Pinterest. We discuss all sorts of practical ways to increase your influence as a designer including strategies for CRIT, how to learn from your PMs, how to prepare for an AI future, and much more... if you're looking to become more of a leader at work (even if you're not interested in management) then this episode is for you ✌️
Fonz gives a masterclass on growth design in this episode as he pulls back the curtain on designing at Netflix and what it takes to ship to millions of users. We also discuss our journies as entrepreneurs, dealing with ambiguity at work, and the importance of growing as a writer. Fonz is truly a lifelong learner and this episode is gold for anyone who wants to grow in their understanding of business 💪
In this episode, Jorn shares the full Framer story starting with his journey as an early designer at Facebook. He also provides insights into Framer’s 9-year overnight success story and a sneak peek of their plans moving forward. We also jam on the potential impact of AI on design—just wait until you hear Jorn's take on the future of design systems ✌️.
En liten tjänst av I'm With Friends. Finns även på engelska.