The Exchanges

Q In terms of inculcating that in the company, do you just behave that way? And everyone models that behavior after you, and so it's sort of you're unconsciously aligned, or is it something you're constantly pushing as a small team?

A I think a lot of a company's culture is a consequence of its founding team, or what have you. I think the founding team at Unblocked, and you know, same with BuddyBuild, was customer obsessed. It was funny, when we looked through our, kind of, all our support channels at BuddyBuild, the two, the people who answered the most questions over time were my co-founder and I. He beat me. Which just drives me nuts to this day. I would get up at four or five o'clock in the morning and do support for buddy builds, and it's the same thing I do with unblocked. Every piece of feedback that comes in, I see it. I respond to most of them at this point. I think that will be less likely the case as time progresses, but I will see every single one of them for sure.

AI assessment note: “I think a lot of a company's culture is a consequence of its founding team”

Q got started, and then you participated kind of in this next generation when Twilio was coming up, Stripe was coming up, you started to build your last company. Could you sort of break apart those different chapters, what was required to be successful, have things shifted, or kind of the same tenets of building great products for that audience, distributing great products for that audience, more or less the same?

A There's kind of Probably three and a half shifts in my mind, in my career. BizTalk Server was an on-premise, like it was a physical box that you bought with disks, and then we, you know, started to shift CDs or whatever. There was the on-premise. Then I think there was cloud. So when I think of Stripe and Twilley and things of that nature, I think that's kind of in that cloud genre, right? Which is like you call an API, people can use it to perform some function. And then mobile was obviously like kind of the next shift for really a developer ecosystem. And the business models that actually shifted along with them. So you went from like, A site license to like a SaaS based model to kind of free to pay. So every time you have these kind of significant technology shifts, you tend to find that there is actually a shift in the business model that goes along with it. I think the one that we're the half that we're looking at now is the kind of the advent of this AI LLM generative AI technology.

AI assessment note: “There's kind of Probably three and a half shifts in my mind, in my career.”

Q When did you start to get a sense as you started to iterate and work on the company that there was some, some really strong signs of product market fit?

A Actually, the highest compliment I've ever received in my career, I remember it was a gentleman who was based in Eastern Europe, and he wrote in and said that, like, the time that BuddyBuild saved him, having to manage a Mac Mini and all this other stuff, that's the time that he gets to spend with his family, and he really appreciated that. And I was like, that's it. If we can get people to unsolicitedly provide feedback, even if the company doesn't work at that point, I was like, I made an impact in that person's life to the point where they want to take the time to let us know. That was fantastic. So when people start telling us that they love the product.

AI assessment note: “So when people start telling us that they love the product.”

Q Do you think at all about sorting those, or a way that you try to make sense of all of that at any given point in time, or the balance between all those different opinions, your own intuition, and the direction that you want to go, sort of all that type of stuff?

A Maybe another Amazon thing. I think the people closest to the problems are the ones best positioned to solve them. And I think, like, I truly, truly believe that. It's like one of the things that I was really, really impressed by at Amazon. Jeff would have a perspective, but he's like, who's the person actually solving it? You know, give them the data, but let them make effectively the operational decision. I'm being flippant. I don't listen a lot, but the things I optimize for to the things that I sort, sort on is people who have been there, done that. If I have conviction that they've actually experienced this thing before, what kind of idiot doesn't take the advice of someone seriously internalizes it for someone who's been there, done that, and it has like an interest in you being successful. That is like such a wasted opportunity. That would be my magical superpower. If I could like shake people's hands. We've talked about this in the past. Shake people's hands and benefit from all the life lessons without having to go through the experience. I would do that over fly or be invisible any day. What do I sort by? Yeah. With one of the things that I, the investors that I work with, as an example, I like people who have operational experience, who've done something similar that can say like, Hey Dennis, I know every situation is different, but when I had something similar, here…

AI assessment note: “the things that I sort, sort on is people who have been there, done that.”

Q In building Unblocked, did you leave Apple and say, okay, I'm gonna go start a company, and then started to root around for areas that you were gonna spend time? Or did you bump up into sort of the starting point for Unblocked?

A I definitely, you know, I left Apple thinking, like, I basically wouldn't take any conversations if they related to anything technology related. I'd sat on a couple of, like, boards as a consequence of some angel investments, but that was it. If people wanted to talk to me about anything tech related, I was not interested in it. Zero. I'm just kind of burned out on it. I didn't, basically wouldn't talk about it, wouldn't take any meetings, wouldn't discuss it for about a year and a half. I just wanted some space from it. I mean, probably not to do something from what we were talking about earlier, which is you just need distance from things to see what's important versus what's not.

AI assessment note: “I left Apple thinking, like, I basically wouldn't take any conversations”

Q When you think about where the people came from, the first five, 10, 15 people that, that were really successful in the context The context of BuddyBuild and now potentially in Unblock. Do they come from all sorts of small companies, big companies, startups? There's just no rhyme or reason.

A Arguably, I was a big company person when we started BuddyBuild, right? I worked at a big company at Microsoft and Amazon. What does this guy know about starting and running and operating a business or what have you? I think that's just intellectually lazy. I don't know where I would find it now. I copied and pasted it. You had these great interview questions, which I thought were the most, you know, those behavioral type. Yeah, there was behavioral type questions that you can see all over the place. You know, I've done interview training at these other companies. But the thoroughness and thoughtfulness of the questions that you asked specifically, we would use those as a tool to figure out how do we basically speed up the first three to 50 hours of working with someone.

AI assessment note: “You had these great interview questions, which I thought were the most”