00:03:28 · Charlie Gearside
[00:03:28] S0: Yeah. I won't lie. It was one of the hardest decisions I've ever made. It's like when you frame it like that, it's like, oh, massive company growing awesomely. People are like, oh, why would you, like, leave that? And that's like, on the face of it, you tend to agree. And then I think it's just... It was... Yeah. It was tough. It was a painful journey of, like, a lot of introspection and sort of a lot of... Essentially a lot of therapy. You know, what... You know, I should be better at this. Why why am I not enjoying this as much? And then you sort of just, like, reach a point where you go... You get comfortable with who you are and what you're good at, what you're not good at. And I think that's where where I was, like, comfortable going, okay, there's more to life necessarily than this company, my identity being, like, intertwined with the company as well. And so there was it like that that part. And then there was the other part of why Eucalyptus is obviously just doing so well. And the the people and personalities there is... Are, like, very... Yeah. They're perfect for this stage of the business. So, like, the question was, like, does me being there actually help to make it an incrementally better company? And the answer that I got to was like, probably not. And so, yeah, it's been six months since I've been out of the game.
00:04:59 · Adam Miller, Charlie Gearside, S2
[00:04:59] S1: And was there... That sounds like quite a, like, a rational decision. Like, there was you, the company, and you felt over time there was less of a fit, almost like a very mutual and sort of happy breakup. But was there also any element to burnout after that? You were working there for six years. It was such a wild ride. The company's producing million... Hundreds of millions of dollars of revenue. There's a lot of stress on that. [00:05:20] S0: Yeah. I mean, you have to burn yourself, right, to, like... People talk about balance, but there's not really balance as a founder as you guys know. But you don't don't really wanna change that. It's like a... An awesome thing. I think the telling part about burnout was, like, once I was, like, four months out. And I think I went to, like, the first board meeting since I'd been out just like how mentally... How I felt so much sharper. So it's kinda like this, like, low grade flu that you carry. [00:05:57] S2: Burnout's like a Brain fog. [00:05:58] S0: Right? It's a brain fog. [00:05:59] S2: Right? Yeah. [00:06:00] S0: So, yeah, I think you're right, Adam. It was a factor. I just didn't really notice it.
00:06:00 · Charlie Gearside, S2
[00:06:00] S0: So, yeah, I think you're right, Adam. It was a factor. I just didn't really notice it. [00:06:05] S2: Yeah. I think even just seeing you since when we first met, you seem a lot more energized. You seem a lot more, like, present, which is which is a really interesting thing to see. I think when I think about you, I think I think about a polymath. Right? Because you're an art director. You taught yourself how to code. You're like a creative meets technology. Those kind of personalities are often very good at the early stage and and thrive a lot in chaos. Did you always know about that about yourself, or is this kind of a a recent introspection thing that you've come to around, like, the places where you think you thrive the most?
00:06:05 · S2, Charlie Gearside
[00:06:05] S2: Yeah. I think even just seeing you since when we first met, you seem a lot more energized. You seem a lot more, like, present, which is which is a really interesting thing to see. I think when I think about you, I think I think about a polymath. Right? Because you're an art director. You taught yourself how to code. You're like a creative meets technology. Those kind of personalities are often very good at the early stage and and thrive a lot in chaos. Did you always know about that about yourself, or is this kind of a a recent introspection thing that you've come to around, like, the places where you think you thrive the most? [00:06:40] S0: Yeah. It's a little bit of a recent introspection. I think you're like... You sort of like... It's like... Yeah. You look back and you're like, oh, okay. This narrative makes sense. Yeah. Yeah. I've always liked getting my hands dirty and understanding, like, the technology at a core level or, you know, I'm a terrible drawer, but I believe that, like, given enough time, I can, like, draw something that sort of resembles what I'm trying to do, for example. So it's sort of... But, like, this approach that learn all the skills and then eventually when it's time to hand the skills off to other people that, like, at least you can have, like, a more serious conversation about, like, what to do. Yeah. So, like, jack of all trades and sort of master nun has been my my approach. And, yeah, you're right. General... Generalists are great... Good at the early stage, but less so later on.
00:06:40 · Charlie Gearside, S2
[00:06:40] S0: Yeah. It's a little bit of a recent introspection. I think you're like... You sort of like... It's like... Yeah. You look back and you're like, oh, okay. This narrative makes sense. Yeah. Yeah. I've always liked getting my hands dirty and understanding, like, the technology at a core level or, you know, I'm a terrible drawer, but I believe that, like, given enough time, I can, like, draw something that sort of resembles what I'm trying to do, for example. So it's sort of... But, like, this approach that learn all the skills and then eventually when it's time to hand the skills off to other people that, like, at least you can have, like, a more serious conversation about, like, what to do. Yeah. So, like, jack of all trades and sort of master nun has been my my approach. And, yeah, you're right. General... Generalists are great... Good at the early stage, but less so later on. [00:07:35] S2: But then, like, the counterexample of that is this whole kind of founder mode thing that took over probably about a year ago where people like Brian Chesky were, like, coming back in who are more generalists. Like, Brian's a designer and, you know, a creative at heart. Yeah. And then there's a whole, like, Steve Jobs coming back in. Yeah. Do you think that there's a role for, like, the generalist CEO? Like, you know, Tim's a generalist. You're probably more creative than Tim.
00:07:35 · S2, Charlie Gearside, Adam Miller
[00:07:35] S2: But then, like, the counterexample of that is this whole kind of founder mode thing that took over probably about a year ago where people like Brian Chesky were, like, coming back in who are more generalists. Like, Brian's a designer and, you know, a creative at heart. Yeah. And then there's a whole, like, Steve Jobs coming back in. Yeah. Do you think that there's a role for, like, the generalist CEO? Like, you know, Tim's a generalist. You're probably more creative than Tim. [00:07:59] S0: It's the CEO. Like, the CEO part... You're right. It's like the ultimate generalist. Right? So if you're the CEO, there's there's that role for you. But if you're realistically an executive, you need to sort of Yeah. Be strong in, like, your area. Yeah. And thankfully, like, Tim is, like, an absolute amazing, like, generational CEO in so many different areas. Like, many of which were areas that, you know, like, marketing and stuff that we we both worked on. So, like, I felt even more comfortable that, like, I wasn't leaving a Yeah. Much of a Yeah. A hole. [00:08:36] S1: Yeah. And you mentioned balance before, the lack of it. It's like when you look at your past six years with you can... Being at a hyperscaling company, like, were there periodic elements of balance and peace or is it retrospectively? It was just always pushing it to the limit, and it just always felt like chaos.