The Exchanges

Q Is there someone that you looked up to when you were younger that maybe made it possible for you to dream For something like this?

A Yeah, that's a good question. You know, I'm kind of one of these odd people that has a lot of people that I feel like I learned from, but not that many people that I look up to from the perspective of, well, this person has done exactly the thing that I want to do. You know, I've had dozens of amazing mentors throughout my career. I still have dozens of amazing mentors that I lean on all the time who I'm deeply grateful for and respect, but, um, You know, there's, I think for me, it was more like I grew up in Silicon Valley, and everybody's parents were doing something spectacular and crazy, but no one parent and no one experience stands out in my mind. In fact, it took me probably, like, 20 years to even realize that one of my best friends in elementary school's dad was, like, one of the first 10 or 12 people at Apple, and I just thought, like, oh, they've got a really big house, that's cool. You know, but I didn't really, I, I didn't, like, look up to him, per se. You know, I'm, I'm one of those people that kind of feels like, You know, you've got to choose your own version of the path, and then you can learn from others about how to do incremental pieces of it. Um, but, uh, you know, I don't have, it actually took me about seven or eight months into the founding of First Principles before I even clearly was able to identify a couple of other people who were doing things that…

AI assessment note: “no one parent and no one experience stands out in my mind”

Q Yeah, I guess I was looking for something like, was your father, or your grandfather, or your uncle, or your aunt, or your mom, is there someone that you had direct access to that was actively running businesses that you had a chance to observe that kind of gave you this idea, or this mindset, or no?

A Yeah, that's the thing is, is no, you know, and I, and I frankly, it's a handicap, right? You know, as I get older, I reflect more on what people have learned before they show up at the table. And, you know, you, especially as you start working with people who are just getting, graduating college, you can really notice this difference, because you can see who has certain instincts and who doesn't have certain instincts, even if they come from the same great school, for example. But I'll give you like a, a really short, but sort of funny story on this. Um, so in, uh, high school as a freshman, um, my favorite sport was baseball, and I tried out for the baseball team, and the previous year I had been an all-star on the baseball team, um, and so I thought, like, No problem. Like I'll make the baseball team. Well, it turns out I got cut from the baseball team. Um, and, uh, this probably had more to do with the fact that like, I didn't really like the coach and he didn't really like me and we were probably. You know, not very nice to each other. It's like, like I literally didn't even get a single at bat and got cut from the team. Um, and this caused me to take up golf and nobody else in my entire family actively played golf at all. And eight months later with no professional training and no access to a country club, I was a member of the varsity golf team of my high school. And so …

AI assessment note: “Yeah, that's the thing is, is no, you know, and I, and I frankly”

Q You mean you, you wish for a European lifestyle?

A I actually lived in the UK for a while, and it was wildly eye-opening because I was working for a US-based startup and living in the UK. And like, literally one part of my job was to try to indoctrinate the same level of urgency culture that we have in America for a startup in a variety of different countries in Europe, in the Middle East, and, uh, and really all around the world. And it was, that part of the job was exceedingly difficult. Exceedingly difficult because, you know, people would say, well, yeah, there's more to life, right? And so you could get someone to work really, really hard from like nine to six. Um, but you know, come seven o'clock was a totally different ballgame.

AI assessment note: “I actually lived in the UK for a while, and it was wildly eye-opening”

Q Would you say you fly internationally often then? Cause I, I would only do it international.

A Yeah. So international is its own whole thing. Uh, you know, the, the honest truth is like the, the airline industry has been dramatically propped up, uh, by our government for far too long. In my opinion, I think it should be, uh, heavily regulated, but more free market. And as a result, we have like nearly inhumane conditions in economy. Um, you know, I make this joke. Every once in a while. And to be very clear to your audience, this is a joke. Like, I do not think there's a real comparison here. But there's a couple of things that are actually worse in economy class than they are in prison. And one of those things is you can't go to the bathroom when you want to go to the bathroom. One is actually the amount of personal space that you have. And I could go on and on. And like, I think that what has happened is unfortunately the airlines, you know, took it so far in terms of trying to economize on price. That, uh, they created a situation where, you know, in, for me, like, I would rather not go unless I can afford a ticket that's gonna have sufficient space that I at least feel like a human. Um, so fortunately, most of my, I do a lot of, um, coaching and fractional engagements, and it's hard to do those across too many time zones, so I don't travel outside the United States for business all that much anymore. It does come up once in a while, but it's usually, like, for a work…

AI assessment note: “so I don't travel outside the United States for business all that much anymore.”