Episodes
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A little over a year ago, Joey Banks and I were DMâing each other in Slack about leaving our W-2 jobs and going independent.
So this weekâs episode is a reflection on his journey working for himself and itâs as human and relatable as any conversation Iâve ever had on this show. We go deep into:
Managing your pipeline of clientsCreating a personal knowledge system in NotionFinding companionship as an independent designerStructuring your schedule and maintaining momentumCommunicating your services and pricing yourself effectivelyDealing with uncertainty and all of the unknowns in your first yeara lot moreGet a special offer on Joeyâs âLevel Up with Figmaâ courseJoeyâs Baseline website and newsletterPaul Millerdâs âPathless Pathâ book and his episode on Lennyâs podcastJoey mentioned Oliurâs episode as one of his favorite YouTube creatorsHe also mentioned Stephen Robles YouTube channel -
The pendulum has swung too far with design systems. Somehow theyâve become synonymous with scale. But I believe theyâre 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
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Missing episodes?
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After writing a viral article called âThe Missing Toolâ 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 weâve had regular jam sessions about the future of design tooling, how AI impacts software creation, and everything in betweenâŠ
These jam sessions have been some of the most inspiring conversations Iâve had this year. So this weekâs episode is a way to loop you in on some of those conversations. We go deep into:
The future of design systems with AICrafting a product strategy in todayâs landscapeNavigating the idea maze as an early stage founderWhat it means to have an âAI nativeâ product strategyHow the flattening of the talent stack impacts designersWhy Nim was so inspired by the head of design at UnsplashWhat âtasteâ looks like when operating as a creative directora lot moreCheck out the Dessn websiteNim mentioned V0.dev as a way to create software (also might like Meng Toâs recent episode)The short story Library of BabelStudio Ghibli animation studiosGraza olive oil as an example of what a strong brand looks like in a commoditized product line -
Over the last few months, Iâve interviewed the people designing cutting edge AI products like Perplexity, Claude, Dot, Humane, Visual Electric, and moreâŠ
During that time Iâve created a running list of all the metaphors and mental models theyâve used to explain what itâs 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
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One of the most impressive things Iâve seen a designer make all year is Meng Toâs Dreamcut.
Itâs the perfect example of what it looks like to transition from traditional designer to builder đȘ So if youâre 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 heâs spent 10+ years teaching designers how to code through Design+Code. So in this episode we go deep into:
Mengâs tech stack and go-to AI toolsHow to fine-tune visual details in codeThe secret to an effective first 10 promptsHow to find the perfect first project to buildHow much code you need to know to build with AIWhat parts were easier/harder than Meng expectedWhy Meng considers Claude the newest design toola lot moreâŠMeng uses Claude + Cursor to build his ideasMengâs original .svg pattern product that he build to get startedMengâs new Dream Cut editorMeng previously used Screen Studio (which is awesome), CapCut, and Eleven Labs for videosAI typically uses TailwindCSS (Meng also mentioned the Shadcn component library)Meng also mentioned V0 and Bolt as alternatives to ClaudeScratch is visual programming for kids -
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
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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 weekâs episode is all about how designers and startups can succeed in a world where everything is changing. We go deep into:
Ideal traits for a founding designerHow startups can strategically attack incumbentsWhy the future belongs to designers who can shipThe backstory behind Soleioâs investment in PerplexityA potential future where one designer can service 5+ startupsWhat you can do to invest in your future founder journey todayHow Soleio approaches the design tooling space as an investorWhy we wonât use smartphones the same way 5 years from nowa lot moreSoleioâs first episodeMeng Toâs video editing product (episode coming soon)Granola (Sam and Chris are the founders)Interview with Perplexityâs head of design (Henry Modisett)Pattern Breakers by Mike Maples, JrChapters 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
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This weekâs 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 oneâs âjuice per minuteâ score is off the charts.
Some of my favorite highlights:
How the team prototyped Claude ArtifactsNew mental models for designing AI productsThe way designers shape strategy at AnthropicHow to master the dark art of prompting as a designerThe future of language as the dominant interface for AIDesigning for infinite degrees of freedom vs. user journeysHow Joel designed his interview process at Airtable/Anthropica lot moreâŠThe CEO of Anthropic (Dario Amodei)âs essay: Machines of Loving GraceA new 3 minute video showing how the team built Claude ArtifactsChad Thornton was the Head of Design at AirtableEverett Katigbak is the Brand Creative Director at AnthropicKim Bost is the design leader Joel collaborates with a lotJoel mentioned Jason Yuanâs interview about designing AI products with soul -
Airbnb is one of the truly iconic design-driven companies. They set the bar for design innovation in so many ways. So this weekâs 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:
How Airbnb is bringing vitality to the visual languageHow Airbnb is empowering designers to be designersHow to succeed in a design review with Brian CheskyWhy itâs not enough to think in terms of flows and screensWhy Airbnb is updating their design system to use more 3DHow they redesigned the checkout and welcome experienceWhy Airbnb has prioritized prototyping in code earlier in the processa lot more -
Imagine your first traditional âproduct designâ job is designing the Snapchat messaging UX for millions of people across the globeâŠ
Well thatâs what Dan Morenoâs journey looked like as an engineer turned designer.
So this weekâs 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:
Danâs formula for presenting design ideasHow Dan grew his visual skills as an engineerInside look at the AR exploration team at SnapchatHow to get the CEO of Snap excited about your ideaWhy designing at a startup brings more responsibilityHow Dan rethought what Snapchat messaging could bea lot moreSnapâs Lens StudioAndrew McPhee (Danâs first manager at Snap)Gaurav Misra (founder of Captions)Pop a component plugin for Figma -
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:
What it looks like to design with soulWhat makes Jasonâs design process uniqueWhy Jason left Apple to build New ComputerHow Dot is the spiritual successor to MercuryOSHow more designers need to become AI engineersWhy Jason thinks dynamic interfaces are over-hypedHow to design a product based on one magical interactionWhat Jason learned about storytelling from his background in theatrea lot moreDownload Dot or check out the websiteJason's original MercuryOS projectThe original Dot website featuring Meiâs story (from the Wayback machine so give it a minute to load)Jason references Shigeru Miyamoto (the creator of Super Mario Bros) -
Mariana Castilho has one of the most impressive career trajectories of any designer Iâve ever met.
I first saw her while mentoring through Shift Nudge and within a few years sheâs 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:
The future of design engineeringWhat makes designing dev tools uniqueHow Mariana has grown as a visual designerWhat itâs like working with design celebritiesWhat it means to care deeply about implementationHow she finally succeeded her 3rd time learning to codeHow teams like Vercel consistently hit a high bar for crafta lot moreSave $200 and join me in enrolling for UI Engineering 101 for designersMarianaâs component library UI LabsMariana led the original design for v0 by VercelVercelâs Geist Design System -
This weekâs 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 âwhat makes a piece of software feel great?â
Some of the key talking points:
The 3 levels of animationShipping a major refresh of the Netflix iOS appWhy shaders are a big deal (and how they work)How Janum built the download animation for ArcWhy Janum built his own animation engine (Wave)Learning the principles of fluid design working on the iPad pointera lot moreCheck out Janumâs demos on his website2018 WWDC talk âDesigning fluid interfacesâThe Book of Shaders websiteDisneyâs 12 principles of animation -
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. Thatâs allowed him to invest in many of the design founders that youâve heard from on this shown (like Jorn from Framer or Colin from Visual Electric).
So the goal of this conversation is to tap into Benâs 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:
The story of investing in FramerHow second-time founders think differentlyUnderstanding your gaps as a design founderWhat it looks like to truly act as an owner at a startupWhat Ben looks for when investing in design foundersWhat types of market opportunities Ben is most excited aboutHow Ben transformed customer support in his first month at FBThe things you should be learning on the job before launching a startupa lot moreApply for the Designer Fund Partnership program
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Imagine leading the design of an AI product that skyrockets to a billion+ dollar valuation in under two yearsâŠ
Thatâs 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 didnât 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 NOTES
Ivan (CEO of Notion)âs tweet about not having a design systemPerplexityâs incredible brand designer named PhiWe talked about how booking.com is a masterclass in optimizing UIKEY 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 youâll need a grid, type system, color system, buttons, etc.). We donât have to overcomplicate design systems. Theyâre 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. Youâre 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.
âHaving designers that can code is a hackâŠquality just happensâ
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 itâs a UX question, the designer needs to make a call (âgo with your gut and if you want to change it later you canâ). This is also why having designers who can code is key. Nothing is cemented. You donât 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 canât possibly mock up all use cases. You have to think about interfaces as slightly abstracted (ex: âentity comparisonâ 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 isnât going to be perfect.
Youâre designing the system, giving AI the tools to use, and hoping that it works most of the time.
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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 itâs 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 âPM-yâ 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 Ryanâs course âDescribing the ROI of designâRyanâs 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 Iâve ever made in my career. So I wanted to find the perfect designer to give a personal branding masterclass and I think itâs Oliur.
Heâs built a massive audience across YouTube, Instagram, Twitter, etc. and he shares his hard-earned knowledge in this episode:
Oliurâs 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 workOliurâs iPhone presets and high income streams videosWe talk about his friend Ali Abdaal (YouTuber, Podcaster, NYT bestseller)Jason Levinâs iMessage screenshot of Travis Scott performingI referenced Jack Butcherâs âthis is pointlessâ graphDan Pettyâs âThat Marker PackâThe old Audience Building course on Maven (RIP)Turkish designer Oguz (Oliur talked about the power of his aesthetic)Gabe Valdiviaâs new app Almanac that he built with Cursor -
This weekâs 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 thereâs 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 moreâ KEY TAKEAWAYS
Nobody knows what theyâre doing
This is especially true when youâre designing products for emerging technologies like AI. Itâs easy to look at people working on these AI-native products and assume they have it all figured out⊠but weâre all still learning and exploring whatâs possible. This came up in George Kedenburgâs 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
Thereâs a trend Iâm 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 isnât the way to learn. You have to want something to exist in the world and use that as a reason to figure out whatâs 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 Cornellâs storytelling abilitiesMaheenâs demo for animating drawings (itâs very fun)We referenced Colin Dunnâs episode about the importance of naming in AI productsMaheenâs colorized photos of PakistanMaheenâs FakeID podcastMetaâs 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 thereâs 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 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 youâre responsible for designing the kitchen.
You donât know what the user will order, so itâs a lot of trial and error to ensure you have the right data on hand at the right moments.
Itâs no different than thinking through drop-off in an onboarding flow. Which is why George views working with these models as âprompt designâ rather than âprompt engineeringâ
There are no AI edge cases
When youâre prototyping AI products, your prototypes donât âbreakâ or âfall overâ like they do in Figma. Thatâs because the boundaries of what exists in the prototype become much blurrier.
Instead of designing contained flows, youâre 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
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Visual Electric has quickly become my go-to product for image generation and in this weekâs 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 Electricâs 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 âVisual ElectricâLessons 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 wouldâve been impossible to imagine these types of products. Colin believes the electricity layer will quickly become commoditized, and instead is solely focused on building âappliancesâ 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 đChoosing the level of abstraction is one of the core challenges with designing AI products. Most users donât want to be burdened by all of the knobs and levers of the AI model. Thatâs why itâs essential that we define new patterns and mental models that make AI easy to understand. But you have to be careful, because âthe more you abstract something, the less control users have over itâ. One example Colin shares is why theyâre considering combining the âreference sliderâ and âcreativity sliderâ. 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 Electricâs new product? đ 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 âVisual ElectricâHereâs Manualâs case study on designing the Visual Electric brandVisual Electricâs brand story page (which Ellis Hamburger helped with) - Show more
