The Exchanges

Q just judging based on like how you looked and also I'm just like, can't put two and two together because you've done like eight things. And I mean, uh, so I kind of want to wind back a little bit. So starting with Fitbit, like, you know, you, you, you joined this company relatively early. It goes public. Like, why did you leave? Why did you stay with the company?

A Yeah, so I joined Fitbit through an acquisition of a small startup called Fitstar. We were about 15 people at that time. Um, and so, went from being in a very entrepreneurial environment to a pre-IPO tech company that was about 2000 people when I joined. So that was a really big transition, but learned a ton through that process. Like, I think what you get at a later stage company is a bunch of really experienced people who have done this over and over again. And know how to be professional technologists and scale something and have a full sales org and all of that. But late stage companies are probably not for me. Like I like, I like being in a very entrepreneurial role where I get to talk to end users, solve problems for them, make a really big impact. Um, and so I just had that entrepreneurial itch from very early on in my career. And, and that first seeing that first acquisition, I saw those, those founders life Like, really changed through that acquisition as well.

AI assessment note: “late stage companies are probably not for me. Like I like, I like being”

Q And are you more of a bootstrap person? You said you were on indie hackers, which is more of a bootstrap community, or are you more in the camp of like raise venture, go big? How do you think about it?

A I would say I, yeah, I'm good at being an indie hacker type entrepreneur, but I like having VC funding. Like, I think the scale that you can get with VC is very different. You have to have high conviction, convince a bunch of really smart people about it, and then do something fast. And like, if it doesn't work, you get to move on to something else. Whereas with a bootstrap company, you don't get that kind of feedback. So it's like, I think you make money faster. You can be personally wealthy faster and, and you, you get to help people directly. Um, but you don't get that opportunity for scale unless you work on it for like, 15 years. So it's just a very different approach, I think.

AI assessment note: “I'm good at being an indie hacker type entrepreneur, but I like having VC funding.”

Q So you sold the business, you sold Moonlight to Poll Request. What was it? Can you talk a little bit about the M&A process and what you learned around how to sell a company?

A Yeah, um, I had no idea what I was doing, so we just went to our investors and, um, they introduced us to a variety of people who might be interesting, and then we also went back to, like, our first enterprise customers and things like that, and pretty much ran a sales process. Very similar to fundraising, so just having as many calls as possible and then narrowing down a few prospects, um, and then the deal process was pretty quick. I mean, we were an early stage company at that point, Um, so it was kind of like, do you want to do this or not? Like, do we want to keep running this business or raise more funding or do this deal? Um, and so it was, it was the peak of the pandemic when we did that, and it was just the right outcome for us at that time. And then that company bought Moonlight, kept it running in the way that we had originally designed it and like actually bought the platform. It wasn't an acqui-hire situation. So that was really attractive as well. Because we had just built this really strong community of software developers around the world. Um, and they were, you know, living off of the platform. So, um, great experience overall. And I think it's just like, you have to try to get an, an exit in most cases, but if you try, there's something out there that will be a good fit for all of your users that you've built over time.

AI assessment note: “we just went to our investors and... pretty much ran a sales process.”

Q What other, I mean, I'm, I'm loving this hot take stuff. Like what other hot takes do you have that most people probably would disagree with you, but you, you think that, you know, you're on the right track with?

A Well, this is very unrelated, but I think remote work is a very contentious topic right now. Like, my last company was evangelizing remote work, and I was like, everybody should work remote. We never need to go to an office again. Um, but I've spent most of my career as a remote worker at this point, and I feel extremely ungrounded and community-less. Like, I have to work really hard to find those things. Um, so I think We're gonna have to invent something. Like, either we're going back to offices at least a couple days a week, or there's gonna have to be a lot of innovation in how we can engage with each other, especially for junior employees. Like, the reason I have a technical background is because I worked in an office with other people and learned from them, and I just, I don't think I would have gotten that virtually, even with, like, Zoom and everything we have today. But at the same time, I don't really want to go to an office from, from nine to five every single day. So, um, for me, the answer is living in a city and finding community that way. Uh, but I think we're gonna have kind of a crisis if people don't go back to an office at all or build a community outside of their house.

AI assessment note: “I think remote work is a very contentious topic right now.”

Q You, so you sold the company, then you went to the SCIM to do product design. Why did you do that? And what did you learn about newsletter businesses in that process?

A Yeah, mostly I had just been like a long time reader of the SCIM. I was in New York. I wanted to be in person cause I had spent three years remote and was feeling very ungrounded. Um, had never really worked with women either. So the skim is like, I would guess, 90% women and then two female co-founders. So that was mostly why I was attracted to it. And then, um, I actually came on as a product manager and got to hire a team of designers and engineers to relaunch their mobile app subscription. So that was just a cool opportunity to take their content business. Like it was a lot of journalists and media people working there and then bring in the first tech team. And apply more of those mechanisms that I'd learned at other tech companies. So, um, I think it was, it was interesting being at a company with mostly women because I'd never even worked with women before. And then also, um, a company with a lot of media and journalism people who think very differently than the tech world does. So all good lessons. I think I'm, I'm, I'm not meant to be in that role. I like working in a really technical organization with, with a little more balance, but it was a good learning experience again.

AI assessment note: “mostly why I was attracted to it. And then, um, I actually came on”

Q And how did you know you, you weren't meant for that role? Cause I think a lot of people are working jobs that they're kind of like, yeah, I think I like it. I might like it. Like some days are good. Some days are bad. Like, how do you know if something is the right fit or not?

A I think I just wasn't feeling activated there. Like I like being in a company where I can be super ambitious and pursue things that are hard and that where I feel like an entrepreneur. And it just didn't feel like that for me. Like, I think media in general, and this is definitely a stereotype, but it's more of like, you go to work, you do your job, and then you go home unless you're like an investigative journalist or something like that. Um, and so I was just looking for like a little more ambition and, and I wanted to be working really hard in my twenties and making things happen. And I just didn't feel that there, but it's, it's a great organization. Like they've, they've scaled this media company in a crazy way. Um, I think It just, it didn't feel right to me.

AI assessment note: “I think I just wasn't feeling activated there.”