5 • 1.5K Ratings
🗓️ 12 June 2025
⏱️ 102 minutes
🧾️ Download transcript
Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions.
What you’ll learn:
• Why design should report to engineering, not product
• The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60
• How to create design tenets vs. principles (with real examples)
• The counterintuitive reason to delay drawing or prototyping as long as possible
• Why software is fundamentally a medium, like film or music (not just a tool)
• Why Bob “bounced off the culture” at Pinterest, and lessons from failure
• The lunar landing story that teaches us about championing radical ideas
• How to evaluate if a company truly values design before joining
• The moral obligation of software makers to build great products
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This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue.
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Where to find Bob Baxley:
• Instagram: https://www.instagram.com/baxley/
• LinkedIn: https://www.linkedin.com/in/bbaxley/
• Website: http://www.bobbaxley.com/
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Where to find Lenny:
• Newsletter: https://www.lennysnewsletter.com
• X: https://twitter.com/lennysan
• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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In this episode, we cover:
(00:00) Introduction to Bob Baxley
(03:52) Apple's lasting culture
(06:15) Navigating unique company cultures
(13:19) Finding a company that truly values your role
(15:46) What is design?
(17:17) How to help founders understand the value of design
(23:08) How to align product managers and designers
(26:31) Design reporting to engineering
(30:54) Integrating engineers early in the design process
(33:43) The maker mindset
(35:14) Challenging the assumption that design is time-intensive
(38:04) Design tenets vs. design principles
(45:25) The moral obligation of great design
(51:48) Understanding software as a medium
(01:01:20) Reducing ambiguity for product teams
(01:07:04) Giving designers space for creativity
(01:08:48) The "primal mark" concept
(01:12:05) AI prototyping tools: benefits and risks
(01:17:00) AI as a life coach
(01:21:22) Life lessons from the Apollo program
(01:28:24) Lightning round and final thoughts
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Referenced:
• Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs
• Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney
• Pinterest: https://www.pinterest.com/
• X: https://x.com/
• Uber: https://www.uber.com/
• Airbnb: https://www.airbnb.com/
• Slack: https://slack.com/
• Ed Catmull on X: https://x.com/edcatmull
• John Lasseter on X: https://x.com/johnlasseter5
• Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on
• Humane: https://en.wikipedia.org/wiki/Humane_Inc.
• Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive
• Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/
• Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/
• Tim Cook on X: https://x.com/tim_cook
• ThoughtSpot: https://www.thoughtspot.com/
• Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/
• Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/
• Honeywell: https://www.honeywell.com
• IDEO: https://www.ideo.com/
• Nutanix: https://www.nutanix.com/
• Lego: https://www.lego.com/
• Leica: https://leica-camera.com/
• Porsche: https://www.porsche.com/
• Patagonia: https://www.patagonia.com
• Brian Eno’s website: https://www.brian-eno.net/
• Scenius: why creatives are stronger together: https://thecreativelife.net/scenius/
• The Beatles website: https://www.thebeatles.com/
• Disneyland: https://disneyland.disney.go.com/destinations/disneyland/
• Tomorrowland: https://disneyland.disney.go.com/destinations/disneyland/tomorrowland/
• Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product): https://www.lennysnewsletter.com/p/unorthodox-product-lessons-from-n26-and-more
• Larry Page: https://en.wikipedia.org/wiki/Larry_Page
• Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin
• Design Principles: https://principles.design/
• Tableau: https://www.tableau.com/
• Figma: https://www.figma.com/
• Target self-checkout: https://corporate.target.com/press/fact-sheet/2024/03/checkout-improvements
• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch
• eBay: https://www.ebay.com/
• Williams Sonoma: https://www.williams-sonoma.com/
• Amazon: https://www.amazon.com/
• Monument to a Dead Child | Raw Data: https://podcasts.apple.com/ca/podcast/monument-to-a-dead-child/id1042137974
• Toast: https://pos.toasttab.com/
• The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas
• The Plant: https://pixar.fandom.com/wiki/The_Plant
• Microsoft CPO: If you aren’t prototyping with AI you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai
• How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna
• Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/
• John C. Houbolt: https://www.nasa.gov/centers-and-facilities/langley/john-c-houbolt/
• The Apollo program: https://www.nasa.gov/the-apollo-program/
• Archive clip: JFK at Rice University, Sept. 12, 1962—“We choose to go to the moon”: https://www.youtube.com/watch?v=QXqlziZV63k
• Alan Shepard: https://www.nasa.gov/former-astronaut-alan-shepard/\
• Blue Origin: https://www.blueorigin.com/
• Yuri Gagarin: https://en.wikipedia.org/wiki/Yuri_Gagarin
• Wernher von Braun: https://en.wikipedia.org/wiki/Wernher_von_Braun
• Yuri Kondratyuk: https://en.wikipedia.org/wiki/Yuri_Kondratyuk
• John Houbolt’s memo: https://space.stackexchange.com/questions/2823/text-of-john-houbolts-letter-proposing-lunar-orbit-rendezvous-for-apollo
• Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx
• Lawrence of Arabia on Prime Video: https://www.amazon.com/Lawrence-Arabia-Peter-OToole/dp/B0088OINTU
• Leica M6: https://leica-camera.com/en-US/photography/cameras/m/m6
• Habitica: https://habitica.com/static/home
• Andor on Disney+: https://www.disneyplus.com/browse/entity-faba988a-a9f5-45f2-a074-0775a7d6f67a
• Edward Tufte quote: https://quotefancy.com/quote/1449650/Edward-Tufte-Good-design-is-clear-thinking-made-visible-bad-design-is-stupidity-made
• Ansel Adams quote: https://www.brainyquote.com/quotes/ansel_adams_106035
• It Takes a Village to Determine the Origins of an African Proverb: https://www.npr.org/sections/goatsandsoda/2016/07/30/487925796/it-takes-a-village-to-determine-the-origins-of-an-african-proverb
• Henry Modisett on LinkedIn: https://www.linkedin.com/in/henrymodisett/
• Perplexity: https://www.perplexity.ai/
• Golden State Warriors: https://www.nba.com/warriors/
• Steph Curry: https://www.espn.com/nba/player/_/id/3975/stephen-curry
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Recommended books:
• From Counterculture to Cyberculture: Stewart Brand, the Whole Earth Network, and the Rise of Digital Utopianism: https://www.amazon.com/Counterculture-Cyberculture-Stewart-Network-Utopianism/dp/0226817423
• Hare Brain, Tortoise Mind: How Intelligence Increases When You Think Less: https://www.amazon.com/Hare-Brain-Tortoise-Mind-Intelligence/dp/0060955414
• The Elements of Typographic Style: https://www.amazon.com/Elements-Typographic-Style-Robert-Bringhurst/dp/0881791326
• Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0060589469
• Time and the Art of Living: https://www.amazon.com/Time-Art-Living-Robert-Grudin/dp/0062503553/
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
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Lenny may be an investor in the companies discussed.
Click on a timestamp to play from that location
0:00.0 | Almost everyone living in a modern economy now is going to have hundreds of interactions with the phone or with the computer. |
0:07.0 | And unfortunately, a lot of those interactions are not going to be great. |
0:09.8 | We have an obligation is product people to put that emotional energy back into people's lives. |
0:14.6 | You actually have a really unique perspective on just what is design. |
0:17.5 | Design is trying to imagine the future you want to live in and then take the steps to make it real. Saying a company is design-led does not mean it's design. Design is trying to imagine the future you want to live in and then take the steps to |
0:21.9 | make it real. Saying a company is design led does not mean it's designer led. I've never seen |
0:26.4 | somebody grafted on after the fact. It's there at the beginning in the root DNA or it doesn't |
0:30.9 | exist. It wasn't a successful stint at Pinterest. I just sort of bounced off the culture. I came |
0:35.3 | in thinking I was supposed to behave the way I behaved at Apple, which is very direct, fighting hard. Why did you decide to join Apple? I just seek out |
0:43.0 | opportunities to witness history. The whole company is constantly asking, how can the thing that I'm |
0:47.8 | working on, be a little bit better? Why do you think that people that have left Apple, like a lot of |
0:51.9 | amazing things haven't emerged. |
0:57.0 | Today, my guest is Bob Baxley. |
1:03.2 | Bob is a designer, executive, and advisor who's built-in lead design teams at Apple, Pinterest, |
1:05.6 | Yahoo, and most recently Thoughtspot. |
1:09.0 | Over the course of his career that spanned over three decades, Bob has played a pivotal role in the design of the |
1:11.9 | Apple Online Store, the Apple App Store, Pinterest, and early in his career, Yahoo! Answers, |
1:17.8 | products that have been used by hundreds of millions of people around the world. |
1:21.5 | Bob also mentors individuals and advises organizations that are working to improve the practice, |
1:26.6 | craft, and culture of digital |
1:28.0 | product design. |
1:29.5 | There is something in this conversation for everyone, from why you should consider having |
... |
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