35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley

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/

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