The Exchanges

Q Detailed, but essentially my bug for entrepreneurship was seeing other people make bad business decisions. And a lot of the time it's surrounded around treating their customers poorly or treating their employees poorly. And I realized if I could do it better than I could probably build a better business and whatever it was I wanted to do. So who was your inspiration for getting started and being an entrepreneur?

A My very first inspiration was actually my grandfather. Uh, and to a degree, You know, I, I've thought about this enough that I think that maybe he was kind of leaning me in the direction of having something to do that wasn't going off and trying to surf. Uh, instead I ended up serving those surfers for a little while. I was just a little kid. He was sort of a polymath and he had been a bit of an entrepreneur himself until he became a doctor later in life. So I was inspired by him in a lot of ways. And he had pointed me in the direction of the idea of creating your own career. And so he was probably my original inspiration. And then early on, I guess in the nineties, I was probably inspired a lot by people like Bill Gates and to some degree, Steve jobs and, you know, the other players at that time. And I read some of their material. I remember business at the speed of thought by Bill Gates. It's a pretty heavy read. It's, you know, he's not the best writer at least back then, but at the same time, it blew my mind what he was talking about, what you could do with technology. And in business and how you could automate things in such ways that was just like, oh my God, this is being done. This is future tech. And I was so enthralled by the future and technology and I wanted to be a part of it. And it felt to me like I could work with other people on their ideas, but I had plenty of…

AI assessment note: “My very first inspiration was actually my grandfather.”

Q So what were some of those first ideas that you had?

A They kind of run a gamut, but I think probably one of the more noteworthy ones after I'd sold my first company, I had started dabbling in this idea of Trying to disrupt the operating system world. My thought was, okay, computers are fairly expensive. And the reason for that is because of the operating system, primarily back in those days. And unless you wanted to build your own operating system, like a Linux or whatever, um, which most people weren't into, then you were going to end up paying just more money than most people could afford for computing. So I thought if I could democratize this a little bit by making Software a little bit more accessible by, uh, making it sort of like a pay as you go service. So we're talking like software as a service before this was a popular notion. But what I ran into was this idea of creating a technology. It's like, think of like a dongle or something that you keep on your key chain. You could plug it into any computer. Didn't matter if it had an operating system, but it would get you online and it would bring you to your hub. And that would have the software that you are paying for that you want to use on a daily basis. So this idea, it seemed like a really cool thing to do, but number one, the bandwidth wasn't really there yet. Most people didn't even have internet in their home. If they did, they didn't have high speed. And then on top o…

AI assessment note: “I had started dabbling in this idea of Trying to disrupt the operating system world.”

Q Let's go a little bit further towards the, the, the, the burst, right? How did the burst affect entrepreneurship?

A You could ask that question like six different ways. How did it affect X? And the answers would be wildly different. Entrepreneurship. I don't know that it was necessarily affected as much besides the fact that like venture capital, especially shrank up. But, um, you know, and the markets were really rough there for a little while, but it actually forced more people into entrepreneurship than you might expect. Um, because from my observation anyway, since I had kind of a pulse on the IT budgets of a lot of companies at the time, what I saw is everybody shrank up their IT budgets. And so hiring immediately just went away and a lot of people were getting laid off. And so what were those people doing? Now there was a pretty good mix of what was happening. Um, I, I knew people that were six figure IT people that were suddenly serving at Bennigan's or, you know, waiting tables somewhere because they couldn't find a job anywhere. And I'm kind of like, hmm, you can't use your skills some way. Now it's not like today where there's like so much more opportunity, but at the same time, I did see a lot of people at that time go, okay, well, I just got laid off, but I'm going to go into business for myself. And some of those people created companies that exist today. It was definitely a roller coaster for a lot of people for those first few years. And then it only was, I think, amplified ag…

AI assessment note: “it actually forced more people into entrepreneurship than you might expect.”

Q when the internet wasn't really a big thing, and not many people could afford to build a website, and there was no social media, no smartphones, how did your company that helped to provide jobs to IT people, Placements. How did you find these people or how did they find you? How did you do the marketing and the sales and the placements without any of the support of technology?

A Okay. So in that particular case, it was a little bit out of the ordinary for the time. This was me just kind of leveraging my own magic previously. And during that time, a lot of people would be using things like radio, direct marketing, um, and just old school, you know? Door to door, walking, you know, into people's offices and actually talking to people. I'm telling you, this is like how you did it. And to a degree, that's exactly how I did it too. But, um, I just didn't do like the radio and the banners and all this kind of stuff. Um, when I worked for someone else doing that placement, what he wanted to do, he had got the idea that he could just hire people to get on the phones, cold call and make these, these deals happen. And he would get a percentage. And this was just a business model that was going to be magic for him. Problem is he didn't know anything about it and he was going about it the wrong way. So when I came in, he was my friend's dad. And when I came in to help him out and I see that he's got a room of like six or eight desks and there's phones and phone books and that's it. Yeah. I sat down and I knew how to cold call. I had some sales experience, whatever, but I realized that there's going to be some times where I'm going to have to go meet people in person. I'm going to have to do a handshake deal in order to make this happen because we're talking huge n…

AI assessment note: “walking, you know, into people's offices and actually talking to people”

Q How did nine 11 change the way people start and run businesses?

A I'm not sure that there was necessarily a direct correlation from nine 11 that was, like, a fundamental shift in how people, um, started businesses. I think that there was definitely some, some weariness from the whole IPO aspect because we had just gone through, you know, the, the.com bubble burst and then people getting wiped out because of wall street being closed for, I think it was five or six business days. Um, and the rest of the world was still trading. And so there was a lot more, I think kind of homegrown and we'll, we'll stick to it for a while approach for, Just a minute there. And then also there was a fundamental shift because I think really the catalyst for it was like when Paul Graham decided to do that experiment, you know, his wife got him the idea. And the next thing you know, Y Combinator came along and that there was a shift in what people expected as Y Combinator grew over the years that became sort of a part of the, the lexicon where people were thinking like, oh yeah, accelerators, this is part of how you do it. It's actually, I think kind of grown to become a bit of a problem over the years where if you listen to the stories of accelerators that start in other countries, especially I've heard this in like, um, Central America and a little bit in South America as well. You, you build the accelerator and all of a sudden the local governments and everybody…

AI assessment note: “I'm not sure that there was necessarily a direct correlation from nine 11”

Q Let's end with, what do you think the next 10 years of the internet and the way people interact with the internet and how businesses do business on the internet? What do you think that looks like?

A So yeah, there's definitely some big question marks here, um, and it's exciting territory for me. I've always been very drawn to future tech, and, um, I'm very interested in seeing how Physical interaction and all kinds of interaction with technology changes over the next 10 years. I think that's probably going to be one of the bigger fundamental shifts. Um, there's a bunch of them that we could talk about, like, I think what we were going to see, and especially over the next couple of years, we should probably see is like, AI in marketing and, and customer development is going to be a really important factor. Uh, because it's like one of the biggest, hardest problems that people have with businesses is figuring out the customer problem. But how we interact with technology is sort of in its infancy still, I think. So I'm a little curious to see how much things like COVID affect touch, like touch screens and touch devices. Like, for example, there's a, an elevator company that realized very quickly, oh, Gosh, our touch screens are not what people are going to want to use in elevators. So they came up with like a pedal system where you could just like tap it with your foot and people were more than happy to use that. Um, and so that's something that wouldn't have happened if it weren't for this particular, you know, pandemic issue. And I don't know that there's necessarily a lot …

AI assessment note: “Physical interaction and all kinds of interaction with technology changes over the next 10 years.”