Dive Club 🤿

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:What it takes to thrive as a founding designerWhy Henry likes hiring designers who can codeThe challenges of designing dynamic interfacesWhy Henry didn’t want to anthropomorphize the AIThe initial creative direction for the Perplexity brandThe keys to making a consumer product cognitively fastWhy Henry built a mini design system as his very first stepa lot moreSHOW NOTESIvan (CEO of Notion)’s tweet about not having a design systemPerplexity’s incredible brand designer named PhiWe talked about how booking.com is a masterclass in optimizing UIKEY TAKEAWAYSStarting with a design systemBefore 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 codeWhen 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 everythingHenry 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 systemsAt 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:What it’s like presenting at Airbnb CRITWays to unlock your credibility as a designerHow to mitigate risk when presenting your ideasWhat it takes to speak the language of the businessTypes of “PM-y” questions that designers should be askingHow Ryan led a massive redesign of the Airbnb booking flowThe right (and wrong) way to make a case for investing in UX debtHow to talk about your work in a way that resonates with non-designersa lot moreGet $100 off of Ryan’s course “Describing the ROI of design”Ryan’s case study on redesigning the Airbnb checkout flowPast interview with Alex Schleifer (Chief Design Officer at Airbnb)

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:Oliur’s keys to growing on social mediaDifferent ways to create leverage in your careerHow he (accidentally) landed a billion-dollar clientHow you can get more confident putting yourself out thereSpecific ways to build meaningful connections with other designersWhat designers need to know to get better at marketing themselvesa lot moreOliur cites James McDonald as an example of someone sharing their workOliur’s iPhone presets and high income streams videosWe talk about his friend Ali Abdaal (YouTuber, Podcaster, NYT bestseller)Jason Levin’s iMessage screenshot of Travis Scott performingI referenced Jack Butcher’s “this is pointless” graphDan Petty’s “That Marker Pack”The old Audience Building course on Maven (RIP)Turkish designer Oguz (Oliur talked about the power of his aesthetic)Gabe Valdivia’s new app Almanac that he built with Cursor

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:New types of interface patterns for AIThe unique ways she thinks about prototypingEthical considerations when designing AI produdctsHow Maheen explores AI models through side projectsWhy the goal posts for what it means to be a designer are shiftinga lot more⭐ KEY TAKEAWAYSNobody knows what they’re doingThis 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 > everythingI asked Maheen what traits are more important than curiosity for people interested in designing AI products. Her answer? Nothing.The importance of passion projectsThere’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.Maheen references Alex Cornell’s storytelling abilitiesMaheen’s demo for animating drawings (it’s very fun)We referenced Colin Dunn’s episode about the importance of naming in AI productsMaheen’s colorized photos of PakistanMaheen’s FakeID podcastMeta’s AI releaseMaheen raved about the Rosebud journalling app

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:How to become a creative problem solverHow George navigates ambiguity at HumaneWhy there’s no such thing as an edge case with AIWhat George learned while using AI to learn PythonHow AI is reshaping the landscape for software designWhy George created a Slackbot to prototype his ideasWhy designing AI products is a bit like designing a kitchena lot morePushing past the pixelsThe 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 engineeringIf 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 casesWhen 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:Visual Electric’s big bet to take on CanvaThe hidden challenges with designing AI productsColin's approach to early user and market researchThe art and science of raising funds for your startupWhere the value will accrue in the landscape for creative toolsWhere Colin draws the line between abstraction and power in UXThe wild backstory of how the company was named “Visual Electric”Lessons learned learned from early startup ideas that were shot downKey takeaways:AI is like electricity. Once we gained access to this new form of power, we immediately replaced candles with outlets. But it took 50+ years before the microwave and other staple household appliances were invented. When electricity came on the scene in the late 19th century it would’ve been impossible to imagine these types of products. Colin believes the electricity layer will quickly become commoditized, and instead is solely focused on building “appliances” for AI. Because someone is going to build the oven, the sewing machine, the coffee percolator, the electric can opener, etc. It might even be you 😉Choosing the level of abstraction is one of the core challenges with designing AI products. Most users don’t want to be burdened by all of the knobs and levers of the AI model. That’s why it’s essential that we define new patterns and mental models that make AI easy to understand. But you have to be careful, because “the more you abstract something, the less control users have over it”. One example Colin shares is why they’re considering combining the “reference slider” and “creativity slider”. It simplifies the UX but at the cost of control. And striking that balance is one of the challenging parts about designing Visual Electric.Language is an awkward medium for visual ideas. We need more effective ways to provide visual inputs if we want to generate high quality visual outputs.Want to get early access to Visual Electric’s new product? 👉 Click hereColin talks about his great his experience with User InterviewsGreg Rosen was the investor who helped Colin in the early daysJess Lee is the Sequoia partner they met withTom from Manual led the branding and chose the name “Visual Electric”Here’s Manual’s case study on designing the Visual Electric brandVisual Electric’s brand story page (which Ellis Hamburger helped with)

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:How Nate went from engineer at Snap to the Browser Co.Why design at Arc prioritizes fingerprints > consistencyHow Nate collaborates with engineers on ArcThe story behind Arc Search’s hook featureThe Browser Co’s culture of prototypingHow Nate balances intuition and dataa lot more…Nate’s gamified personal websiteA24 film studioNate references the Co-Star astrology app and the old Zenly appPatrick Moberg (the designer on Boosts)Karla Cole (the designer who pulls inspiration outside of tech)Nate’s feeeed RSS app

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:How to unlock the skill of interaction designWhat Apple’s sandbox unlocks for designersWhy they decided to launch Play as a mobile appThe importance of keeping your hands in the clayHow AI might impact the future of interaction designa lot moreDan mentions his cofounder JoonYong ParkThe App Clip that first blew my mind

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:Gavin’s journey learning SwiftUIHow Gavin got into designing app iconsHow to design physics-based interactionsWhat it’s like designing for power users at LinearWhy interaction design is so important for mobile appsWhy Gavin uses code almost exclusively for prototyping nowWhen it makes sense to prototype at the beginning of your processThe interplay between custom and stock components in mobile designThings by Cultured CodeJanum shows interactions in the Netflix mobile appEpisode with Brian Lovin (who Gavin worked with at Github)Episode with Alex Cornell (who started the design of the Linear mobile app)Parallax effect from the Linear onboarding screen

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:Why they decided to pivotHow Vincent went cowboy modeA look at the future of design engineeringWhat good design looks like in an AI worldWhy visual search is a big deal for future AI toolsHow Vincent used video to get Figmates excited about his ideaa lot moreMarco and Jordan from the old Diagram teamMatt Dailey was the engineer that proved designs can be represented as images2024 Config Keynote showing Vincent’s Uber example for visual search

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:What didn’t ship at Config and whyHow they navigated the early idea mazeHow the role of designer will be impacted by AIWhat it will be like designing dynamic interfacesWhat makes Jordan’s new role at Figma so uniqueWhy renaming layers was such a big internal debateWhy the sparkle icon will become the new floppy diskThe surprising pivot that led to Jordan’s favorite AI featureHow Jordan prototypes by hacking on top of the Figma code baseThe old Diagram websiteFigma’s new AI landing pageFigma’s blog post introducing AIFigma’s 2024 Config Keynote

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:How the role of staff and senior designers differThe traits shared by the best designers at GithubHow to give your ideas a chance to become memesHow to avoid conversational spinout on your projectHow to identify opportunities using systems thinkingHow Kathy is growing as a design leader at OptimismSpecific techniques for storytelling and presenting ideasSome of the people mentioned in this episode:Max Schoening (former Head of design at Github)Brian Lovin (bookmarking repo project)Kat Fikui (coworker at Github whose .readme we mentioned)Connor Sears (old manager at Github)Jack Conte (Cofounder of Patreon)

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:The story behind his startup CocoonHow Alex leverages his background in videoAlex’s precision and obsession with languageWhy Alex left linear to work on generative AI at MetaWhy getting buy-in for your ideas is kind of like a math proofBehind-the-scenes of the wild videos Alex made at FacebookLessons learned designing the Substack and Linear mobile appsThe mental models Alex uses to construct compelling narrativesa lot moreAlex’s startup CocoonAlex’s famous Chevron vs. 3 Dot video from FacebookAlex’s favorite monospace font is Jet Brains and his favorite serif font is TiemposKlim is Alex’s favorite type foundryWe discussed the dual-panel approach in the Amie mobile app

This week’s episode with Maggie Appleton is a deep dive into designing for AI products and LLMs. Maggie shares about her experience as the first designer at Elicit (an AI assistant for research papers) and all of the unique challenges surrounding helping users interface with LLMs.We also go deep into:How Maggie’s grown as a frontend developerWhy Maggie feels like she’s in a short-run limboStrategies for improving your technical literacyHow writing online has impacted Maggie’s careerThe AI-native tools that Maggie is drawing inspiration fromHow advancements in AI will redefine her role as a designerHow Maggie’s new understanding of LLMs is shaping the way she designsWhy Maggie is more interested in the cognitive applications of AI rather than generative AIMaggie is currently leading design at Elicit (they’re hiring)“How Trello is different” is where Joel Spolsky explains the differences between horizontal and vertical softwareOpenAI’s introduction of ChatGPT-4oWe talked about the product tldrawThe expanding dark forest and generative AI: Maggie’s talk about the possible futures of flooding the web with AI-generated contentEpisode with Soleio where he talks about looking for “time to proficiency” in design candidates

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.Ian’s course Sell the Idea (use the code RIDD at checkout for 30% off)Ian’s personal websiteIan’s business Aide HealthMackinnon and Saunders (the stop motion company Ian worked with)

~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:Avoiding burnout amidst the chaosHow Amy negotiated her Duolingo offerAmy’s advice to proactively prepare for a layoffThe ways Amy iterated on her portfolio presentationHow Amy’s career coach shaped her interview strategySome hard lessons learned during her job hunt processHow Amy measured everything in her application processa lot moreShow notes:Amy’s layoff announcement postCareer CompassCharlotte Burns (Amy’s job hunt coach)Levels (transparency database + salary negotiation tools)Amy’s job announcement postSponsors:Framer: How I build websitesJitter: How I animate my designsRaycast: How I do everything on my computer

Julius Tarng is the ultimate generalist designer.He started the design tools team at Facebook where he made a massive impact on products like Origami.He then freelanced as a design engineer for companies like Felt, Anthropic, and even prototyped some of the early AI features for the Arc browser.Now he’s in his first-ever engineering role at Linear.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:Julius’s twitterFelt — a better way to work with mapsDaniel Smith (Linear designer that Julius pairs with)Origami (Facebook’s prototyping tool)Brandon Walkin (ex: Facebook, Apple, now at OpenAI) who made the adaptive pointer for iPad.What are GPUs and Shaders? (Julius’s tutorial video)

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:Sketching on paper vs. sketching in codeWhy shipping quality software is like campingHow Raphael identified the MVP of the problemWhat it was like building Cron in YC during COVIDWhy you should design dialogues as first-class citizensWhy Raphael didn’t invest much in the Cron landing pageThe differences between a design toolkit and a design systema lot more lessons from a successful first-time design founderRaphael’s TwitterThe OG Cron websiteScreenshot of the Cron dialogues in Figma

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:How to create a culture of decisivenessWhy great design leaders are like chefsHow to succeed in executive CRITs at AirbnbHow designers should prepare for an AI futureWhat it means to operate with a “first team” mindsetWhat it takes to achieve Airbnb’s level of craft at scaleWhich elements of the Airbnb culture you can instill for your teama lot moreAlex’s Twitter and LinkedinAlex’s “People vs. Algorithms” podcastMentioned Airbnb alumni:Katie Dill (Head of Design at Stripe)Ethan Eismann (SVP Design at Slack)Karri Saarinen (CEO at Linear)

Noam Segal has led research at companies like Meta, Airbnb, Wealthfront, Twitter, and most recently Upwork. He also teaches the #1 user research course on Maven. So this episode is a masterclass in user research. We discuss:How to conduct better interviewsThe keys to an effective research planHow to become a masterful research storytellerHow AI is creating a new wave of research toolsWhen to rely on qualitative vs. quantitative tacticsThe modern user research tools you need to know aboutHow to ensure research is integrated in the product processNoam’s modern research tech stack:SprigGenwayDscoutSteve Portigal’s book: Interviewing users (how to uncover compelling insights)Mr. Beast’s YouTubeLenny’s Podcast with Judd Antin: The UX research reckoning is here