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

**Bob Baxley** (0:00)
Almost everyone living in a modern economy now is going to have hundreds of interactions with the phone or with the computer. And unfortunately, a lot of those interactions are not going to be great. We have an obligation as product people to put that emotional energy back into people's lives.

**Lenny Rachitsky** (0:14)
You actually have a really unique perspective on just what is design.

**Bob Baxley** (0:17)
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 designer-led. I've never seen somebody grafted on after the fact. It's there at the beginning in the root DNA or it doesn't exist.

**Lenny Rachitsky** (0:31)
It wasn't a successful stint at Pinterest.

**Bob Baxley** (0:33)
I just sort of bounced off the culture. I came in thinking I was supposed to behave the way I behaved at Apple, which is very direct, fighting hard.

**Lenny Rachitsky** (0:40)
Why did you decide to join Apple?

**Bob Baxley** (0:42)
I just seek out opportunities to witness history. The whole company is constantly asking, how can the thing that I'm working on be a little bit better?

**Lenny Rachitsky** (0:49)
Why do you think that people that have left Apple, like a lot of amazing things haven't emerged? Today, my guest is Bob Baxley. Bob is a designer, executive, and advisor who's built and led design teams at Apple, Pinterest, Yahoo, and most recently, ThoughtSpot. Over the course of his career that spanned over three decades, Bob has played a pivotal role in the design of the Apple Online Store, the Apple App Store, Pinterest, and early in his career, Yahoo Answers, products that have been used by hundreds of millions of people around the world. Bob also mentors individuals and advises organizations that are working to improve the practice, craft and culture of digital product design. There is something in this conversation for everyone. From why you should consider having design report to engineering, why it's your moral obligation to build great products, why you should wait as long as possible to draw a picture or create a prototype of your idea, to what the moon landing can teach us about building better teams and products. I could listen to Bob all day. I learned a ton from this conversation, including a bunch of really unique insights that I've never heard before. A big thank you to Annie Warner, Andrew Hogan, Irene Ah, and Joff Redfern for suggesting questions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of incredible products, including Linear, Superhuman, Notion, Perplexity, Granola, and more. Check it out at lennysnewsletter.com and click bundle. With that, I bring you Bob Baxley. This entire episode is brought to you by Stripe. There's a reason that I've had more guests on this podcast from Stripe than any other company. It's because they hire the best people and they build incredible products. You probably know them for their payments platform which powers my newsletter, and also companies like Nvidia and Salesforce and Zoom and DoorDash. What you may not know is that they have several other products that can help accelerate your revenue such as Stripe Billing which powers billing for companies that you may have heard of OpenAI, Anthropic, Figma, Atlassian and over 300,000 other companies. Stripe Billing lets you bill and manage customers however you want, from simple recurring billing to usage-based billing to sales negotiated contracts. There's also Stripe's Optimized Checkout Suite which is a plug-and-play super optimized payment flow that natively supports over 100 global dynamic payment methods. There's also a product called Link which is an accelerated checkout experience built specifically to increase your checkout conversion. Every single one of the Forbes top 50 AI companies that have a product in the market today use Stripe to monetize it. Half of Fortune 100 companies use Stripe. $1.4 trillion dollars flows through Stripe annually which is equivalent to over 1% of global GDP. Use Stripe to handle all of your payment-related needs, billing, manage revenue operations, and launch or invent new business models. Learn more at stripe.com.
Bob, thank you so much for being here and welcome to the podcast.

**Bob Baxley** (4:00)
Lenny, thank you so much. Thanks for having me. But also just thank you for what you do.
We are still in early days to try to figure out how to make software together. I think of it sort of like where the film industry was in the 1920s. We've had our talkie moment. We're kind of on the cusp of having our shift to color involvement, but we're still trying to figure out how to make movies. And a podcast like yours, specifically yours, I think is one of the greatest resources we have for learning from one another. So I appreciate all you're doing for the community and for helping us as a community make better software.