The Exchanges

Q What are two or three books that you've recommended most to other people?

A I really love Elad Gill's High Growth Handbook. It's organized into chapters about sort of foundational company building, building a leadership team, building a board. And in addition to the thoughtful synthesis on that topic from Elad, there's also, he has a, like an interview of someone that he does relevant to that, that section on each of the chapters. Really, really great read and, and super actionable if you're a leader in a, in a, a young company. I mean, in a completely different end of the spectrum, I, I love big, complicated science fiction. Um, and, uh, I mean, there's like a lot of garbage science fiction out there to be sure, but when you find something special, it's like, it's the best. So probably through the years in that category, there's a book called Hyperion by Dan Simmons. That's, it's just like a total classic. Everybody should read it.

AI assessment note: “I really love Elad Gill's High Growth Handbook.”

Q Is there something that you took away from that experience that taught you what to try to avoid, what to try to pull towards?

A I think I sort of misunderstood or misjudged companies sometimes by thinking about them Like really focused on the, on the, the product execution, you know, kind of, if you find an interesting problem that people, you know, people care about and you, you solve that problem in a really beautiful, elegant, delightful way, that's 10 times better than, than anything else that they can get in that same space. They'll tell their friends and like all the rest of it will sort of take care of itself. And so that was always my ambition. Find a thing that I cared about building. Do a great job building it a really delightful way. Go really deep on listening to people and their feedback and iterate your way to success and sort of breaking through that membrane that we all strive to get across the, you know, kind of really great word of mouth. But I think the thing I've come to better appreciate is that Companies are also kind of like a, they're kind of a math problem that describes how you take, you know, investment and pour them into the equation and out the other side comes returns on some time horizon. And yes, There are variables in that equation that are influenced by the product that you build and all of the little details and decisions that you make about making that product great. But if the equation is fundamentally broken or a big swing in and of itself, no amount of like iterati…

AI assessment note: “if the equation is fundamentally broken or a big swing in and of itself”

Q I thought it'd be fun to start with a story about your time at Apple and you building this now very ubiquitous feature of dragging and dropping something into a folder, which is how you tweet about or talk about it at a talk and the fact that it's still around. Can you just share that story and maybe a lesson from that experience that you've taken away?

A Sure. So Let's see, I was 15 years old when the Macintosh came out. I remember really clearly my entire, you know, teenage years, like all I wanted to do was to move from Columbus, Ohio to Cupertino and work for Apple. And my, you know, my, my heroes were that team of people that were, had like, you know, written their signatures on the inside of the Macintosh. We cracked open the first Macintosh case. You would find the signatures of the 20 people or so who worked on the Mac. And that was like, That was my only ambition, truly. And then this was a period where, like, no one wanted to work for Apple. I mean, that wasn't a thing. And, uh, it seems like maybe a little obvious today, but it wasn't an obvious ambition at all back then. So anyway, I went to college. That's all I wanted to do. Study computer engineering at University of Michigan. And as we talk about my career, it's just over and over and over. I'm going to say, you know, an incredibly lucky thing happened. And the first incredibly lucky thing that happened for me in my career probably was that University of Michigan like happened to be a place that Apple recruited from. I didn't know that when I chose the school, but it made it reasonably easy to connect to a hiring app manager at Apple. And I wrote an actual letter and put it in an actual envelope and put it in the mail and got an internship and drove out. And my d…

AI assessment note: “I was 15 years old when the Macintosh came out.”

Q now the CEO of a company called Xero. What is it like to move from just being a product leader, an engine leader at a company to being the CO for the first time? Why did you do zero as that role? And what have you learned as CO that you wish you knew as a product leader or an engine leader at a company that listeners might find useful?

A It's been a really, really incredible couple of years. You know, in the aftermath of Quibi, I spent a lot of time sort of as I'll do sort of, you know, soul searching about what I learned and what I might want to do next. And You know, as I thought about it, I realized that I, I really wanted to, to move on to something where I could have like a direct impact on the culture and values of the company that I was involved in. I really, you know, got that opportunity at Pandora in a big way. And, you know, I had spent the five years of like Snapchat and Quibi working for Evan and Meg and Jeffrey, who are all incredible business leaders, but have their own very specific sort of style and approach and That leaves, you know, a mark on the culture that's unique to the founder. And then as we just, you know, discussed, like, I'm, I'm always really interested in, in building things that are, you know, are near and dear to me. And I was particularly thinking about like, what can I do that could have like a really positive impact on the world in, in my next chapter. I've been with an awful lot of media stuff through the years, video games and streaming services and so forth. And it seemed like maybe there was something that was Had a little bit more weight to it that I could, I could spend my time on. And so, you know, I, my first thought was I would start something. So I had a company ide…

AI assessment note: “I realized that I, I really wanted to, to move on to something where I could”

Q Did not know that. Let's talk about Quibi. What went wrong there? Do you think there was a path to Quibi having worked out any big lessons that you took away from that experience that you bring with you?

A The kind of miraculous thing about Quibi for me was it relit my enthusiasm for the industry for doing this work. I had left in I think it was December of 2018, and I thought that maybe I was just done making software. I had done it for a really long time, I had done it for like 25 years or something, and I had changed a lot, the industry had changed a lot, and I thought maybe I just didn't have the same passion for it that I had, you know, a decade before. It also seemed like maybe it would be fun to have like another chapter of my life That was just completely different. And I had a whole list of things that I thought I might want to do. I mean, they were really, they're kind of ridiculous. It's like, maybe I want to be a pastry chef. Maybe I want to be a landscape photographer. Maybe I want to, you know, learn to make bad music to put up on SoundCloud or something. I mean, really the only thing they had in common were they were all things that I knew nothing about. People would be like, oh, you think you might want to be a pastry chef? Do you like to bake? And I'd be like, no, I don't know anything about baking. You know, oh, you think you might have landscape photography. Do you take photos? No, I don't make photos. But I was kind of committed to the bit, actually to the point where when, when TechCrunch interviewed me about my departure from Snapchat, I was like, you know, …

AI assessment note: “The kind of miraculous thing about Quibi for me was it relit my enthusiasm”