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Bob Baxley

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116
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2025-06-12
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2025-06-12
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  1. “Yeah, so I'm fortunate at this stage of my career that I usually get to interview with the CEO or the founders or something like that. So what I'm usually looking for is do they have a story as to why they believe in design, like really in their heart and soul, do they care about design? Because if I go into a company that doesn't really value the thing that I do, I'm just not going to have a great time. And I'm going to be constantly buffeting up against all sorts of people. So I want to make sure I've got air cover from the highest people in the company setting the culture. In the case of my, again, my most recent job was with a company called ThoughtSpot. And ThoughtSpot was founded by a gentleman named Ajit Singh. And Ajit grew up in rural India, but he tells this really great story about early in his career. He studied chemical engineering. He moved to the United States. Early in his career, he's working for Honeywell, and they did a couple of engagements with IDO. And as a very young person, he got to see what IDO did. And he realized the power of design. And he's taken that to all of his companies. He started.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “Founders, it's their life. It's very unusual to see founders move out. I have this other theory that a startup is still a startup until the founder moves aside. So by my definition of even meta is still a startup in a way that Amazon's not. And Airbnb is still a startup in a way that Pinterest is not because Ben's moved on. It's really, you don't find out if the culture can sustain itself until the founders are gone. And then you really see what's going to happen.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “I was at Pinterest, I came to think that the job of a startup was to grow the founder so they could continue to lead the startup. And I think what's true for founders is also true for a lot of the other folks in the executive staff. It's very hard to grow emotionally and developmentally at the rate that the company grows. A lot of times I think people get outgrown by the role. And I saw that across Apple. I've experienced that myself at different times in my career. I see that happening with my friends. And it feels like a failure. I mean, if that is the human experience, that's what happens. It's very hard to grow as fast as some of these companies are growing. And I, you know, we could debate the merits of Mark Zuckerberg, for example. But when you think about the trajectory from being a kid in the dorm room to, you know, within like five years, he's like Facebook's a big thing. I mean, think of your own life. Can you like, can you process that level of evolution and change?”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “I think of it more like you're going out on a branch on a tree, and the branch gets a lot more flimsy and can break and you can fall and you get buffeted about by the wind. And it's often at a time in your life when there's a lot going on with your family. There could be things going on with your parents' health. I lost my mother when I was at Pinterest. You know, my kids were starting high schools who were struggling with the teenage years. I had a long, long commute. I mean, there's just a lot going on. And these jobs are super demanding. Everything around you is changing really rapidly. And you're under tremendous pressure because the financial and success stakes are super high. So I think the people like falling off of these jobs is the common use case. That is the common story. We have a bias towards survivors and we all talk about how it looks like they made it to the top. But everybody that makes it to the top, there's hundreds of people that don't. One of the things I took away.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “Of my friends that was at Pinterest, I'm still friends with, he said, You know, I just sort of thought of it as you bounced off the culture. And I think that's kind of the way to think of it. I came in thinking I was supposed to behave the way I behaved at Apple, which is very direct fighting hard. Everybody cares about each other. It's never insulting, but it's intense. And that's not really where Pinterest was at the time. And again, all this is like a decade ago, so I don't know what any of these companies are like today, but at least when I was there, Pinterest had posters in every conference room that said a big poster that said say the hard thing. Well, that's where Pinterest was at the time. And I can assure you, nobody at Apple was having to remind you to say the hard thing. And so I probably could have picked up on that better than I did. I'll say, these careers are really hard. And the higher up you go, I sort of, people think of it like your climate pyramid.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “Thing I took away from Apple, and I think this is true for anybody changing from one major culture to another, is most likely the new place hires you because of the values of the organization you left, but not the behaviors. And so I think it's important to kind of recalibrate and say, well, I want to hold on to these values so that Apple attention to detail, product excellence, doing everything you can for the customer and the user. So try to hold on to those values, but then think, okay, how are those values best expressed in this culture? And I was more successful at expressing those values in the culture of thoughtspot, which was my last job than I was in the culture of Pinterest. If I had to do it again, I could probably do better at Pinterest. So I think that's useful for anybody leaving one very specific culture and going someplace else. Like try to hold on to the values, but not the behaviors.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “Operate like that. Airbnb is one exception. And so you have guys like Hirokia Zai, who leads all of marketing and all of product, and Hiroki is crushing it at Airbnb, who's incredibly successful at Apple. It also should be noted that he was a multi-year gap between the time he left Apple and the time he started Airbnb. So he gave himself a little bit of time to get through the, you know, at Apple, I think it was Tim or Steve used to talk about the Apple car wash. And then when you started Apple, they kind of had to take you through the car wash and get off all that stuff that you'd accumulate.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “Yeah, I'm hard pressed. So, obviously, Tony Fidel would be one with Nest, and he had been outlier. I think the people that, you know, I went to Pinterest and did not have a successful time in my year and a half at Pinterest, I think my own particular mistake, and I've seen this with some other Apple executives as well as we went directly from Apple. Like I left Apple on a Friday and I started Pinterest on a Monday. And I didn't give myself time to recalibrate to the Pinterest culture. So I think at some level, a lot of the challenge is that when you Apple, and it's not just Apple, I think every major tech company, like they have really powerful cultures, you know, you get kind of indoctrinated into those, all those standards. And it's really deep. It infuses all of your behavior and how you conduct yourself in the company away from the company. And so I think it's pretty hard to immigrate successfully from one of those environments to another. And Apple is one of the strongest cultures. And there's not many other cultures that sort of natively.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “Decisions. It's a way of behaving. It's a way of seeing the value of technology in the world. And it infuses everything in that company. I mean, everything from the checkout system when you go to the receptionist to what it's like in the cafeteria, you know, at least what I was there, they had patented the pizza box because they had reinvented the pizza box that you would get at Cafe Max because they're just the whole company is constantly asking, how can the thing that I'm working on be a little bit better? And I think that was something Steve brought to them and had them constantly asking that question.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “So, I actually can't remember where I heard this, so, but I believe the story is true. Steve at one point was recounting the products that he had created that he was most proud of. And if I recall the whole list, it was the Apple II, the Mac, the iPod, the iPhone, I think Apple retail was in the list. And then he said Apple itself. And when I heard that and when I've reflected on it, you know, that is the longest lasting thing. And I remember there was also a story that Steve was talking to, I think it was either Ed Catmill or John Lassiter at Pixar. And he said, you know, everything we make is going to be a doorstop in three years. But the stuff you guys make, this is going to be watching in 100 years. And so I think Steve had some concept of the longevity of these things. They knew the products themselves were very ephemeral, but there's something about the culture of Apple that's lasted a very long time. And I personally believe it'll last for some time yet to come. And it's a way of making.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Letty, thank you so much. Thanks for having me. But also, just thank you for what you do. You know, we are still in early days of trying 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 moment, 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.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Super optimized payments flow that natively supports over 100 global dynamic payment methods. There's also a protocol 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 Stripe to monetize it. Of Fortune 100 companies use Stripe. $1.4 trillion 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. Launch or invent new business models. Learn more at Stripe.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “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 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. Open Anth At Lassian. Number 300,000 other companies. Stripe billing lets you bill and manage customers however you want. Simple recurring billing to usage based billing. Sales negotiated contracts. There's also stripes optimized checkout suite, which is a plug and play.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “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. Big thank you to Annie Warner, Andrew Hogan, Irene Ah, and Joff Redford adjusting 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, Get a year free of a bunch of incredible products. Including linear, superhuman notion, perplexity, granola, and more. Check it out at Lenny's newsletter.com and click bundle. With that Bring you Bob.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “My guest is Bob Baxley. Bob is a designer, executive, and advisor whose built-in-led design teams at Apple Yahoo, and most recently, ThoughtSpot. Over the course of his career that spanned over three decades, Bobus 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. 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. Why you should consider having designed report to engineering It's your moral obligation to build great products.”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “Almost everyone living in a modern economy now is going to have hundreds of interactions with the phone or with a 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. You actually have a really unique perspective on just what is design. 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 doesn't exist. It wasn't a successful stinted Pinterest. 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. Why did you decide to join Apple? 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? Why do you think that people that have left Apple, like a lot of amazing things haven't emerged?”

    2025-06-12 · Lenny's Podcast · 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · IDENTIFIED FROM THE TRANSCRIPT · source