The Exchanges

Q And what has been one of the hardest decisions you've had to make? While running this business.

A There were two points that I had the most agony in the business. I think the first was the first outside money that we raised, you know, suddenly when I wasn't just, you know, just wasting my own time and money and potentially, you know, someone else's money was, was, uh, involved. That was very scary. And then again, when we, when we hired our first employee, suddenly, you know, I was taking You know, someone that was very skilled and very good and having them come work at a, at a company and, and, you know, early stages of a company, you still don't know if they're going to succeed and by all rights, most startups, you know, shouldn't succeed or won't succeed. And so that was certainly scary. And then, you know, along the way, we, we've done, uh, you know, a couple of layoffs, you know, around COVID and around some, You know, economic turmoil and those decisions are always hard because it's not, you know, it's not a spreadsheet. Certainly you can use spreadsheets to help you make the decisions, but at the end of the day, you're, you're impacting people's lives and you know, that's a, those are always really hard things to do as a, as a founder, as an operator.

AI assessment note: “we've done, uh, you know, a couple of layoffs”

Q Beyond that, what are some other things that you didn't know being a CEO would be like? Like, um, I guess what, what was the romanticization versus the reality?

A I don't know that it was ever that romantic for me, if I'm being honest. Like, I never wanted to be an entrepreneur. Like, that wasn't my goal. I know there's a lot of folks out there that, you know, want to be a CEO, want to be an entrepreneur, want to start a company, and they kind of start with that, and then they go search for an idea, where I very much was on the other side, where I never really wanted to do that, but I had an idea that I thought needed to be worked on, and so that's how I became an entrepreneur. I will say, the one thing that I certainly wasn't prepared for, um, and in retrospect, I, this should be obvious, or maybe it is obvious to people, it just wasn't obvious to me, but You know, making a company successful requires sort of all the different teams, all of the different functional areas within the company to be successful, to do well, and to work with each other. Having come from a product management background, I thought product management was the center of the world. I thought if you build a great product, you know, the rest is sort of ancillary because, you know, especially in technology companies, it's all about product, product, product. But in reality, you could have the best product in the world, and no one knows about it, and you're not going to have a successful company. Or you could have the best marketing in the world and everyone knows your…

AI assessment note: “the one thing that I certainly wasn't prepared for”

Q Have you ever thought of stopping this business or walking away?

A Never considered walking away. I mean, maybe in like, you know, in a non-serious way, like in the same way that I, you know, consider going to the moon. Uh, you know, there have been a couple of times that there has been inbound interest from companies around acquisition. Um, I, I had investors, I had board members ask, you know, if the company were to be acquired, you know, would you want to stay on board? Actually, we had to, you know, potential acquirers ask that question. And, and I would like, again, you know, the goal was never to be an entrepreneur, you know, while it's, you know, there are certain nice things about being the CEO, like being, you know, in many ways, the final decision maker around the things. That's not really why I started the company. I started the company and solved the problem. So if there was an acquirer, I think I'd want to stick around and help solve that, that problem. If, if they would have me, Um, you know, I'd also like to go on a real vacation at some point, you know, a two or three week vacation, and so, you know, maybe the real dream is to get to the point where the, you know, I feel like I can entirely unplug for three weeks or, or a month. Uh, and, and, you know, unwind a little bit, and then come back and, and, you know, get, get, get back at it.

AI assessment note: “Never considered walking away. I mean, maybe in like, you know, in a non-serious way”

Q What is something that you've had to change about yourself through this process?

A I'd like to think that I haven't changed myself at all. Um, I said, you know, something I'm really bad at that I'm trying to get better at is I don't like to ask for help. I get just, it's, you know, I, I'm sure it's psychological and has something to do with my childhood, but like, it is not comfortable for me to ask someone for help in any form, right? Whether it's to do something simple, like make an introduction that someone knows or do something harder, like, you know, literally anything. Um, and so, you know, I have realized that I can't do everything on my own and, you know, I have a, a great network of friends and colleagues and, Investors and board members that are more than happy to help. I just need to ask them for it. And so I've tried to get better at, at, at doing that. It's still a very uncomfortable thing for me. Again, not because my network doesn't want to help me and they wouldn't be more than happy to. It's just, it's not a natural thing for me to do.

AI assessment note: “something I'm really bad at that I'm trying to get better at is”

Q How do you spend your days mostly now?

A Well, I've read this article. Three years ago about how Jack Dorsey spends his days. And I think this was before he was a dual CEO and maybe before he went a little bit off the deep end with some of the things he went off the deep end with. And, you know, he was like, I have a day of the week where I spend it on marketing. I have a day of the week that I spend it on sales. And I have a day of the week I spend on product and engineering. You know, he kind of had broken his week up into the major functional areas. And I'm like, that sounds like a great idea. I should do that. Uh, that didn't work at all. So that's not how I spend my days, to have one day for each of those, those various areas. You know, what I started doing is, is basically laying out goals for every week, the things that I, that I want to get done. Uh, and depending on what those goals are, we're, we're starting to do a fundraise right now. And so it's reaching back out to, to investors that I've talked to historically and getting time on their calendar. So the goal for this week is to set up 25 of those emails and get those, get those meetings scheduled. So I'm spending a lot of time Sort of, you know, sending out those emails, but also preparing all the materials for those meetings when, when they get started. Um, you know, next week, it may be actually doing those meetings. The week after that, it may be, it …

AI assessment note: “laying out goals for every week, the things that I, that I want to get done.”

Q What's been one of the more expensive mistakes that you've made?

A Early on in a company, you're always looking for, you know, the famous product market fit. Um, I'm still not fully sure that I, I could, I could define what that is, you know, but you're basically saying that, you know, your sales motion, your go to market, your growth, you know, can be Templatized in some ways, right? Where, you know, there, there, there's a need, you've got a product, you've got process and you can, it's all repeatable. And I think there's a, there's an urge, especially for venture backed companies to say that you have product market fit, because that makes it easier to fundraise. And one of the things that you do when you have product market fit is you go, you know, you go invest in the company because you think if everything's repeatable, if you can put in a dollar and get out two dollars and you go put in a million dollars, you get out two million dollars. And you know, if it works like that, You know, every, everything would be great. Unfortunately, if you don't have that product market fit, if things aren't repeatable and you start investing in the company too soon or before you have that, you put in a dollar and you get out 20 cents. Uh, and certainly the more dollars you put in, the more money you lose. And it's not one of those things that you can make up at, you know, with just, just by scaling the amount of money that you lose. Um, and, and, you kno…

AI assessment note: “we've, you know, effectively invested before we probably should have invested”