Jeet Singh: Act Like a Rhino but Never Forget We (A Fireside Chat With Tom Matlack)

In this fireside chat, Tom Matlack sits down with entrepreneur and technologist Jeet Singh to talk about the wild early days of ATG, building one of the first e-commerce and personalization platforms on the internet, surviving cash crunches and lawsuits, going public during the dot-com boom, and eventually walking away to spend a decade making music before launching a new wave of startups. The conversation is part of a summer interview series Tom hosts for his Wesleyan University course, created for first- and second-year college athletes who are beginning to imagine careers beyond sports. Through candid stories from accomplished leaders like Jeet, the series gives students a practical, behind-the-scenes look at entrepreneurship, leadership, and finding their own path in the business world.

Tom: Awesome. So, um, I kind of say this a lot, but I’m super, super excited to talk to you today. Uh, Jeet, it’s been too long, and you know, you’re like one of the most pivotal people in my life, really, in a lot of ways. So we’ll talk about why. But um, the way I like to do this is ask some big kind of hard questions and then start back at the beginning and go through your chronology.

But first, actually, I was curious what you remember about when and how we first met — like our very first meeting.

Jeet: Well… gosh. Well, obviously at that time we were in a really big cash crunch in our little startup at ATG. And we were also in a kind of weird market because everyone was really excited about the dot-internet bubble, and we were doing something very different that no one who was investing cared about. They were like, “Why are you doing that? Why don’t you just do like pets.com?” You know, that was the rage back then.

So we were building software, and we were just discovering our market, and we had some very good customers like Sony and Harvard Business School and MCI — serious customers — in a market we hadn’t anticipated. We didn’t really know much about enterprise software at the time, right? We were a couple of young kids building some neat stuff. But the problem was that we didn’t have much outside investment. We had kind of bootstrapped our company just by doing consulting gigs. So we had enough cash to build stuff, but when we started becoming a product company, our customers were big. They paid really slowly, right?

So we didn’t have enough cash in. No banks would loan us money because we were less than five years old. Young companies just don’t get credit. And so we had been hoping to get some money from some investors, but they turned out to be… you know… not the greatest guys in the world. And that’s when we met, I believe — at that point. And Scott Jones, who was my old boss and really one of the only mentors I had when I was younger, came in to bail us out.

So I do remember you really well. I remember that you struck me as very practical and pragmatic. Your questions were like, “Okay, so what’s going on here?” Even though you didn’t know anything about what we did or anything about our market. I just remember… I remember you had very, very nice chairs.

Tom: We did have nice chairs. But like, I had the sense all hell was breaking loose, but you had these very nice chairs.

Jeet: Yeah. We got them from Herman Miller. We had all these Herman Miller chairs that we got in a fire sale from some company going out of business. They were like, “Well, you know, take some chairs.” So we took like twice or three times as many as we had people… just in case. And yeah, they were really nice. I still like those chairs.

Tom: So… probably the hardest question I’ll ask all day is: what are you most proud of now, having gone through quite a career at this point — from when we met to now? What are you most proud of?

Jeet: That is a tough question. You know, the thing that touches me most is that when you see a lot of people who used to work for us at ATG — and a lot of them are in the industry now, and a lot of them are CEOs of other startups, some very successful ones — they all loved working at the company. And they loved working with the people who were there.

So I’d say I’m most proud of the culture we built. Joe and I had a specific style. You know, Joe and I met in the fraternity at MIT in 1982, and for all those years we sat at the same desk at the company. And we’re still best friends today. I had dinner with him two days ago, even though he travels a lot because he has grandchildren all over the place.

So an old friendship. But we had a very similar way of looking at the world, and I think it percolated down to the staff. We could be tough, but we were always super fair. And I think we created a nice place to work. And you know, there are whatever groups on LinkedIn, and people always say, “Oh my God, that was just the best place to work because of the people and how they treated each other.”

So I’d say that was the most pleasure — just that.

Tom: So, for the students: Jeet’s co-founder is Joe Chung, and they both met at MIT. And we’ll get into that in a minute. But one of the things I always found the most interesting about the company — and we’ll talk about what happened there — was the way you guys actually fit together. Because you’re similar in some ways, but also very different. Like, you’re kind of the outside guy — glass-half-full, the sales guy — and Joe’s a bit the opposite. And I think that was part of the special sauce of how the partnership worked and why it was so successful. And it’s great to hear you’re still best friends and all that. But in terms of the company, that was crucial.

Jeet: Yeah, it was. And it kind of hearkens back to Scott Jones and Greg Carr, the people I worked for at their startup for four years before Joe and I started ATG. Greg and Scott were very similar — Greg was the CEO marketing outside guy, and Scott was the engineer. They met at a Harvard/MIT meetup where engineers would meet people interested in business. Greg was actually at the Kennedy School, and that’s how they met.

When I worked for them, I was employee 13. I left when we were 400 — in four years. And basically everything I learned about startups and business was there. You know, I didn’t learn much at MIT except teamwork, which I’ll get into. That was the big contribution of MIT — the way of thinking about how you work with people.

But Scott and Greg’s interaction and their style of splitting things up was really interesting to me. And I thought it worked really well, even though they were never really good friends. They were very different character-wise, and I know they got on each other’s nerves. I was good friends with both personally, though I became a very close friend of Scott’s over the years.

But to your point — in my case, Joe was the engineer, I was the business guy. We both liked product design, so we both acted almost like a joined brain when we said, “How do we build this?” — me more conceptually and he obviously coding it. But Joe was also a very good salesman, which is funny for the tech guy. He loved going and selling. He had to sell CIOs — the head of IT at, you know, Deutsche Bank or wherever. They wanted to meet the CTO.

So yeah, you’re right — we approached things in certain ways very similarly, but our actual day-to-day tasks were really different.

Tom: So let’s go to the chronology a little bit before we get back to ATG. You grew up in India and went to high school in India. What was that all about? How was that?

Jeet: Oh, no — so my dad was a diplomat. I was born in Sweden. And um, we lived all over the place. I started nursery school in Madrid. We went to Moscow. So we were in Russia ’69 to ’71. We were in Saigon ’71 to ’73 during the war. Then we went to Colombia for four years. And then after Colombia my dad was sent to Uganda during Idi Amin’s time, so it was not a very stable place. I couldn’t go to school there. So at that point they sent me to boarding school in India, in the Himalayas — a Christian missionary international boarding school at 7,000 ft.

It was a great place. Not fancy, but neat. So I stayed there. And then I liked it a lot. And then I could have joined my folks later when they went to Finland, but I was like, look, I’m already almost graduating. I’m happy — I was an athlete, played basketball and volleyball, my girlfriend was there — I didn’t want to leave. So I graduated, and then came to Boston.

Tom: Wow. I didn’t really know that background. So do you think that level of… it sounds like almost chaos in where you were living — did that help you when you got to the tech world? It sounds like you had to be really adaptive.

Jeet: Well, yeah. It’s hard to say. My personality is pretty outgoing. I have friends who grew up like me, and I’d say half of them thrived in a chaotic environment and half didn’t. I think I was lucky that I had four years in Colombia, between 10 and 14, with really good friends. One of them was just here last week staying with us. And then four years stable in India. So I didn’t get jerked around too much when I was 12 or 15, which would’ve been rough socially.

But you do get that sort of outsider mentality — which from a startup point of view is helpful. In a startup, you’re always the outsider. You’re outside the regular business. You’re not one of the big guys. No one believes what you’re going to do. And that outsider mentality is helpful. It’s like, okay — new place, new environment, I don’t speak the language… so what? You’ve got to deal with it.

Tom: So… how did you get to MIT?

Jeet: Well, I think early in high school I decided I wanted to come to the States rather than England, which were the usual options for most kids in the school. Most of the kids were also international — their parents were everywhere from Indonesia to Saudi Arabia to Aramco. There weren’t many international schools in Asia at the time, and ours was accredited by the Middle States Association, so you got an actual American high school diploma. It was a testing center for SATs and APs and all that. So it was kind of a magnet school for international kids from all over Asia who were thinking of coming to the States.

But you could also do O-levels and A-levels like England. By 10th grade, I’d decided, “Yeah, I want to go to the States.”

So after the SATs and all that, you know, this little Christian school had a guidance counselor, and I didn’t know anything about anything. They had these old college catalogs on the walls — usually from places like St. Olaf and Oberlin and the usual somewhat Christian liberal arts schools — not a hint of Ivy League or Stanford or MIT. No internet, right? We were up in the Himalayas. So I wrote away for catalogs, and those giant catalogs started coming. And I thought MIT looked like a cool place.

I didn’t get in — I was on the waitlist. I did get into most of the other places, and I got a full scholarship at Princeton. And my dad wasn’t a rich guy by any means. The maximum salary for an Indian ambassador then was $23,000 a year, even though your expenses are covered because you live in the embassy.

So I sent in my papers for Princeton — like, “Hey, it’s free.” And then I got off the waitlist at MIT. My dad and I visited the U.S. before freshman year — traveled around, visited Caltech and Cornell and Princeton and MIT.

And when I saw Princeton, I really didn’t like it. They were talking about the president’s house and the lawn and the buildings — it felt like a country club. I’d been living in the Himalayas. I was like, I don’t want this.

When I came to Boston, I was like, oh, this is cool. The tour was like, “Here are the secret tunnels. Here’s where we hack the elevator so we can get into places we’re not supposed to.” And it was Boston — restaurants, everything. So I wanted to go there — but I hadn’t been accepted. Then I got in off the waitlist.

Tom: Just by the way — everyone in my family, both my siblings, my father, my grandfather, my uncles — all went to Princeton. And I hate it. I went to Wesleyan, which is much closer to MIT than Princeton. So God bless — you made the right choice.

Jeet: That’s pretty funny, yeah.

Tom: So I want to skip forward because I want to make sure we have enough time to talk thoroughly about ATG. But just for a second — your first job was at Boston Technology with Scott Jones, right?

Jeet: Not really the first.

Tom: Okay — what was your first job?

Jeet: So I thought I was going to be an engineer at MIT — I was a mechanical engineer. I realized I didn’t really like engineering much because it was so cut-and-dry: like, okay, I know the equations, we can make this bridge so it doesn’t fall down. They weren’t complicated questions. I was more interested in political science and economics. So I ended up majoring in political science at MIT, which is very quantitative — policy assessment, more mathematical.

But most people in political science either go into politics, or the Kennedy School, or law. I had no interest in any of those. I didn’t want to be a diplomat like my dad.

The only thing I could do was write — I was a pretty good writer and I could understand technology. I used to write technical manuals and actually made money in college working for a manual-writing company, which paid great. In those days, $12 an hour was unheard of for a student. Minimum wage was $2.75.

So the only skill I had was writing. I got jobs working for a number of tech companies writing, and then it often turned into marketing because they’d say, “Oh shoot, this guy actually understands the product.” And that’s how I got the job at Boston Technology, because they were looking… one of my buddies saw something about voicemail and knew I was a musician — he didn’t really know the difference — and he said, “Hey, this company looks interesting. They’re looking for a writer.”

So I came in as a technical writer. And it’s an interesting story. BT — speaking of how Greg and Scott met — Greg was studying the breakup of the Bell system in the ’70s, when companies could suddenly compete. In the ’80s, they said, “Okay, Bell companies, you can sell additional services too.” And the first thing they sold was call waiting — the little click that tells you someone else is calling. They sold that for like $2. That was their wonderful innovation.

Voicemail was available in companies — you could have a central system — but at home you just had an answering machine. So the Bell companies, with the new laws, said, “Okay, wait. We could sell central office voicemail.”

So they put out RFPs — requests for proposals — to dozens of big companies that sold office voicemail. Uptel, Centagram, Unicus. They put it out to about 55 companies. Greg and Scott responded and said, “We can do — ” you know, the biggest voicemail systems had 12 channels max in your office, or 24 if they claimed it, but they didn’t really have it. We claimed 1500.

And Scott had designed a parallel-processing version where you just stack up PCs with voice cards and transition stuff between them. That was the innovation: how do you do a big one?

And suddenly a new player was entering the space — the phone company. So that’s interesting in business: so many things happen because something else changes — a regulation, a law — and then everyone has to scramble. That’s a good moment for startups to enter the fray. So that happened at Boston Technology.

Tom: So you guys understand — basically, like, this… I mean, they didn’t invent voicemail, but they kind of did actually. Definitely domestically. And there was voicemail commercially, but no one had it at home. These guys provided it — so, kind of a big market.

Jeet: Yeah. Well, yeah. Google didn’t invent search, but they perfected it, right?

Tom: Yeah. So let’s get into ATG. It was started really as a consulting company. Then you started building this enterprise product, and that’s when I showed up. And then… what happened? Like, how did we get from where you were — running out of money — to… we were going… that was November of ’97 in my recollection anyway, and I think we went public July of ’98. Or ’99 — sorry.

Tom: So, it was like, uh, it was a little… it was like 18–20 months or something. So how do we go from running out of money, not quite sure what the hell we’re doing, to going public 20 months later? What happened during that period of time?

Jeet: Yeah. So, I mean, to kind of understand that properly, you have to realize that since we started as a consultancy doing kind of, you know, wacky interactive media — this was a brand-new market at the time — Joe came out of the MIT Media Lab and most of our early employees were from there too.

Since we were doing this sort of high-end consulting, we made good money. But usually, if you build a product, you take in a bunch of investment because it takes years to build a product and then market it. You have to invest a lot. We were just kind of doing it on our own profits from consulting. So that was, you know, I wouldn’t suggest that as an approach. I mean, it worked for us, but barely, right? We almost ran out of money, obviously… more than once. Usually because of either a lack of credit or, you know, at the time you guys came in there was such a big market bubble around a different kind of technology than what we were doing. No one really got it until a couple of years later when they were like, “Oh, wait a minute, this is kind of interesting after all.”

So in some sense, by the time we took the SoftBank money — which was about 7 million or something along those lines, I think — even later, before we went public, we didn’t even use any of that money. But by that time we were a little scared of running out because we’d been in trouble before.

So I think by the time we made that transition, we were also starting to get really good revenue from our customers. So we had that valley-of-death moment, which you guys bailed us out of, right? But that was like… it was a consequence of the fact that the model of changing from consulting to product is a difficult one. And the things that you’re known for are not the things you’re saying you want to do. Most investors are like, “Wait a minute, this is not what you do. What makes you think you can compete against the biggest companies in the world like Microsoft and IBM?”

Tom: So guys, just so you understand the context here of what this product was all about: imagine a world where no one is selling anything on the internet. And basically the consulting work that Jeet and Joe were doing was helping companies figure out how to sell on the internet. And then they built a product which was basically the first e-commerce product platform for people to transact on the internet. Ever. And they were selling that product.

And so while there were internet companies that were basically, you know, a joke — trying to set up pets.com or whatever the hell it was — we were actually building, we were enabling, the world to start transacting on the internet, which turned out to be a great business model.

Jeet: Yeah. Amazon had started doing that for themselves and, as Tom was pointing out, in general people weren’t selling on the internet and suddenly they all wanted to. So now they had to get a product to do it, and that’s where we were — that was the space we were playing in.

The secret sauce, besides just selling on the internet, for us was this idea of personalization. Now we just take it for granted that whatever you click on on your social media is based on what you’ve done before. But this didn’t exist back then. And so people wanted, like, “Oh, well, if you know Tom likes this sweater, shouldn’t we show him these pants as well?” That was a novel concept: personalizing the web page, which means you had to set up a web page specifically for every single person looking at it. That didn’t exist. And that was our real, you know, secret sauce. And also the basis for the lawsuits with BroadVision and so on, which is a pretty funny story.

But we were… and going public was very much related to this BroadVision lawsuit. So to get back to your other question, a lot of stuff was going on. The biggest thing that was going on is we were stealing away customers from our main competitor, who was already public and had hundreds of millions of dollars in the bank. And we were trying to sell to American Express, and to — whatever it was — American Airlines and Blockbuster and big banks and so on. And our competitors would go and say, “Well, hey listen, you’re going to go with these kids? They don’t have any money, no one knows them, and here we are, a big public company with $100 million in the bank.”

So we were losing… and we were still winning. And then BroadVision sued us right around that time, because I think they realized they didn’t want us going public and then suddenly losing the one thing they could say against us, which is that we were small and underfunded. So that was all happening in those same months, Tom.

And so a lot of the… we were at that point pretty close to profitability already. The customers were good. But having the war chest, and especially having credibility versus BroadVision, was a big reason why going public was a good strategic decision.

Tom: So what was the experience like of being on the road show? I mean, I’m sure these guys are interested.

Jeet: Oh, it’s just hellish. It is just the most hellish thing.

So, in a road show — if you guys don’t know what it is — when you want to sell shares to the public, you get an investment bank to come in and be your broker basically, right? And then they go sell to a whole bunch of private investors and other banks the first tranche of your… a small piece of your company, 5 or 10%. And then it’s available for trading in the market.

But the investment bank, which is really a broker of shares that you’re selling — they’re just market makers in a lot of ways — they have to convince all these investors, “At this price, you should do it,” and then they take orders in a book. But since the market can change so quickly — something happens, there’s a war, there’s a market downturn — they have to price that within a very small window, usually a couple of weeks.

So in a couple of weeks, you’ve got to literally meet in person all these fund managers all over the world — mostly in the US, but then Europe and Asia — and you’ve got to meet them all. They want to shake your hand. You tell them the same story that they could hear in a PowerPoint if they wanted to, but they want to meet you. And you do this a gazillion times a day, every day, while you’re traveling at night or whatever, for two weeks. And it’s horribly exhausting, and it’s boring because you say the same thing for 45 minutes — five times in the morning, at lunch (you don’t even get to eat because you’re talking while other people are eating lunch at, you know, Capital Grille or whatever). Then you do it in the afternoon.

And then at the end of it, the fund manager tells your banker, “Okay, we’re in for X million dollars worth of shares,” or whatever it is. And at the very end, on our last day, we were actually on Sand Hill Road in Menlo Park. And after the last meeting, we literally sat in the limo talking to all the bankers like, “Okay, are we in? Is that the price? Are we going to go?” And they said, “Okay, we priced the deal.” And basically a couple days later — or whatever it was, the next day — we’re trading, right?

So it’s kind of nutty. And you’re talking so frequently, saying the same things, that you start losing track of what you’re saying. Like Joe—

Tom: Okay. So it’s actually… uh, you’re breaking up there a little bit, but if you can hear me: one of the things that’s actually fascinating is, part of our class is we have a woman who’s come in teaching students public speaking. And, like, part of my mantra is that’s one of the most important skills you could ever learn. All of life can kind of be reduced to a selling moment or like a political campaign. And God only knows a road show is the political campaign — you have a stump speech, and you’re going to tell it like 10 times a day, every single day. And the quality of a stump speech really matters. It really, truly matters.

Jeet: Yeah. No, it’s really, it’s definitely true. You know, communicating the idea — and the idea is sometimes… you’re not selling Coca-Cola, right? It’s a complex thing in a new industry. And, you know, part of that is: how do you translate it to the things the fund manager will understand?

And the investment bankers do a lot to help: “Here are the things to hit on, because these are the parts they’re thinking about. They’re thinking about this whole new market sector, so talk about that because that’s what they’re interested in.” So it certainly is a good lesson.

Once we went public, we had a PR agency and so on, and before I’d go on CNBC or something like that, they actually trained me — which is absolutely fantastic. And in my gap-year program, I actually taught young people like you guys some of these skills: tape yourself, give a talk, watch yourself. Are you making funny movements with your hands? Are you talking too quickly? Are you not taking enough pauses to let people catch up?

So that was a very good exercise — and it only happened once we were a public company, which is kind of funny, but unnecessarily late. You could learn that stuff in school, right?

Tom: Yeah, we definitely… these guys are definitely doing all that. I don’t know why your video froze there. I don’t know if you can reset that, but yeah, I’m not sure what’s going on there. But I can actually—

So, I do remember you guys being on Sand Hill Road. I remember that pricing call, which was hilarious. And then the next point was: we were fortunate enough that the stock was trading well enough that we did a secondary that November. So it was July we went public and then whatever it was, four or five months later, we were selling more shares that soon—

Jeet: Wasn’t it like about a year or so later? I think it wasn’t quite that quick. It was about a year and a bit later, I think, on the secondary.

Tom: Okay, so whenever we did the secondary. But I remember very clearly the pricing call on the secondary. And so from our perspective — my little group of people — I remember dialing into that call because that was actually the first time we were going to be able to sell a significant portion of shares. And I remember doing the math and where the price of the shares came out in the secondary, where we were able to sell some of our shares, was just north of 100 times our cost basis.

And so I was literally… I was in this offsite in Vermont with my venture capital firm at that point, with my team, and I was in this upstairs bedroom. I just remember I was shaking because it was like real money to me at that point.

And then… so the next point is: just to explain to the guys, when you go public, the bank or the broker forces you to sign a lock-up agreement. And what that means is that if you’re an insider, they don’t want you flooding the market. They want to actually create a liquid market first, and you can only sell into that market after it’s established. So that generally means that for six months you can’t trade. And so even though on paper you may be worth a certain amount of money, it doesn’t really matter because until the lock-up comes off, you can’t sell. You know, you can’t sell it.

And that’s generally a 180-day lock-up. And so the 181st day is a really, really big day. It’s an important day. And my recollection was that was like February of 2000, I believe. And I remember that morning, because there were a bunch of people who had actually shorted our stock, and so there was downward pressure because, “Oh, founders are going to clean out a bit.”

And so the way that works is, if you understand market dynamics, if people are shorting and then a bunch of people show up to buy the stock, the stock actually trades up. And then those shorts have to cover. It actually accelerates the way that the stock moves. The stock will then start to move up more dramatically because the shorters have to bail out basically. And that’s what happened that day. We had a paper amount of wealth, but now this is the first day that the paper amount of wealth is actually going to be liquid. We know there’s a bunch of shorts, right? And they may eat our lunch and the stock may trade down, but in fact what happened is the stock traded up significantly.

Jeet: They bet wrong and lost sort of twice on that one.

Tom: Right. But like, for us — and honestly this is one of the reasons I wanted to have you on — that was life-changing money to me. That was the single day I made the most money of my entire life. And it was like: at that point, my life will never be the same. And so, you know… thank you.

Jeet: You’re welcome. Thank you for bailing us out, otherwise we wouldn’t have gotten there.

Tom: Do you remember when the lock-up came off? Do you remember that day?

Jeet: No, not really. I mean, you know, we went on to selling plans. Joe and I and all the senior managers went on to—

Oopsie… oh, you know what? There you are, you’re back. That was something weird. I just got a note saying “started again.”

But yeah, so one of the things that founders do — especially senior people — so they don’t freak out people or get dinged for insider trading is that instead of actually choosing, “Okay, I’m going to sell 10,000 shares or a million shares,” they put it into a blind selling pool. You don’t know when your bank will sell your shares over a period of time, over a quarter. And I have no idea when those days are, so no one can blame me for saying, “Oh, you knew you guys were just about to lose a big customer, and before it got into the news you sold shares.” That’s insider trading, which happens — you see it a lot.

So we didn’t really want to be in that situation. We were in a blind selling situation where we had no control, and it was sold over time. But to be frank, at that time I wasn’t really thinking about that at all. There was so much going on as a public company. We were growing, everything was kind of… the market was also starting to get a little weird already. So there was a lot going on. I can’t remember thinking at all about the shares at that time. It was pretty busy, busy going.

Tom: So let me — we’re going to get into time — but let me ask you a few more kind of a bit off-topic questions. I know you’ve always been a musician, and there was a period of time after ATG where you had a band. So how do you think about your passion for music and technology and how those kind of weave together?

Jeet: Yeah. Well, I mean, I kind of fundamentally think of myself as a creative person. What I like to do — and Joe likes to do — is, you know, Joe’s also a musician. We played in a band together in the fraternity and then we won the Battle of the Bands at MIT. There were like 55 bands. WBCN was sponsoring the competition and by winning it we got to play all the big rock clubs in Boston — the Rat, TT the Bear’s, Jonathan Swift’s — all the big rock clubs.

So I actually took off a year from MIT just to play rock music at that time. And then suddenly realized, okay, I’d better graduate because I’m going to need a job and the 50 bucks the band gets, split five ways, isn’t going to do much for my living.

So music’s always been a big part of my life. And then, around that time after we went public and after a couple of years after the IPO, I was pretty burnt out. And running the public company part is just not much fun. Before that I was mostly dealing with engineers and designers and customers, which is a lot of fun and very creative — like, how do you solve problems? After you’re public, I was spending 80% of my time talking to bankers and lawyers, which are really not the most fun people to talk to. Nothing interesting going on there — just saying the same old thing, just like on the road show: “Oh yeah, we think things are going pretty well.”

I remember one — I don’t know, you’re probably on this call, Tom — but there was one call where everyone liked these companies that made no money, were losing money but getting customers, and we were profitable. I remember on one investor call someone said, “How come you guys are profitable?” So I said, “We actually spend less money than we make.” Everyone around the table on the conference call is kind of trying not to giggle.

But yeah — I diverged. Running the public company was becoming… I wouldn’t say stressful; it was becoming really boring and difficult. I was traveling all the time. And at that point I was like, “Okay, it’s time to go back to music.” So that’s when I moved to the islands — when I moved to St. Barth, set up a studio, and I played music for the next 10 years. And traveled around the world with the band. We played in all kinds of countries and did crazy stuff. We put out four albums in those 10 years. So it was a much-needed break.

And then later on, 10 years later, Joe and I got together to do RedStar and start some more companies again.

Tom: Yeah. So tell me, just as we wrap it up here: what’s RedStar all about and what have been a few of the wins there, and what’s your unique approach?

Jeet: Well, so we stopped starting new companies about five years ago at RedStar. We did it for about 10 years. We started about five companies. A couple of them got acquired. We did not have any big financial successes. We did have one company that was doing really pretty well called ThirdChannel, but it was retail data analytics and when COVID hit, all our customers — they were shut down. There’s no retail, right? So unfortunately that company sort of got snapped up by a specialist investment firm — kind of a distressed-debt kind of acquisition — where the company’s actually doing pretty well, it’s still out there. But RedStar didn’t make any money out of it. We got kind of washed out by the PE buyers that came in. So ThirdChannel — you can look up ThirdChannel — that’s out there. We started that.

There were a couple other small companies that got bought, but they were small sales, a couple million bucks. So nothing to write home about. But the concept of RedStar was very different. It was: let’s come up with a bunch of ideas with a group of people and then find managers to go run them. So Joe and I were like, “Let’s do the stuff we like the best,” which is: let’s come up with some cool ideas, build the team, the first product, the first two years of it, fund that piece with our own money, and then find outside investors — but also put in a CEO that matches which market it’s going to be in. Because when you start a product, you don’t even know where you’re going to be selling it.

So that was the idea of RedStar. I’d say it was a limited success. It was not a success financially for Joe and me, but it was fun and it was interesting and we came up with some cool companies.

We stopped doing it about five years ago because it just takes so long to get companies going, and Joe and I are both 61. So we stopped doing that about five years ago. And about two years ago, I stopped running one of the firms. So I’ve not been running a company as CEO for a little over two years now. But I’ve been doing research now.

About five years ago, I started doing a bunch of research on my own. So I do music now, I do research in computational theory, and I’m writing a novel. So there you go — back to writing again, where I started.

Tom: So, just for these guys who are 19 and 20 years old, just starting out on their business career, what general guidance would you give them as they’re trying to figure out what to do and how to navigate the world in 2025?

Jeet: Yeah, that’s a really good question. I mean, again, where we started from — and one thing that MIT taught me — is: don’t try to solve any problems on your own. You’ve got to have a team, or at least a good partner that you can bounce ideas off. It’s really easy to get infatuated with an idea you have.

And, you know, Joe and me, it was really interesting because our instant reaction is to disagree with each other. And then we’ll talk it out, right? We were usually sitting at the same desk and I’d be like, “Oh, wouldn’t it be great if we do that?” And he’s like, “Eh, that doesn’t sound so good to me.” And it became our thing. We would just immediately disagree, and then sort of debate ourselves until I was like, “Okay, maybe you’re right.”

And that’s very useful. So don’t surround yourself with yes-people. Find someone you can trust, or a group of people you can trust, when you’re trying to put together a business idea — someone who can shoot holes in it.

So that’s really valuable. And it’s very valuable if you want to do a startup — not all businesses are startups — but in startups it’s particularly important to have that kind of partner to bounce ideas off of, and also to support you when you’re down. Because there are times when you just don’t have the energy, but then somebody else does, right? Someone else can pick up the call with that client, or the guy complaining at you because your product doesn’t work.

So I’d say do that.

The other thing is, depending on what you guys are studying, it’s hard to study business in school. And, you know, I’ve done a lot of teaching at Sloan, at MIT, and at HBS and so on. I’m always struck by how little is kind of learned in those sessions, including in mine. So getting out and doing stuff is a much better lesson to learn. But finding a company — like, for me, Boston Technology was great because I learned about how a small company grows, which is exactly what I needed to start our own.

Some people go to a big company and then they want to do a startup, but they don’t learn anything about startups in a big company. And a company that’s between 100 and 200 people is very different than a company between 50 and 100 or zero and 10. So I think one thing to look at when you’re looking for a job — if you want to — is: think about the environment you want to be in and try to find a job that matches what you’re trying to learn about. Sometimes you don’t have a choice; obviously you take the job you can get. But looking for a big-bank job is very different than looking for a small investment management firm, or looking for a job in a big retail company is very different than getting a job at a consultancy that advises big retail companies like Coca-Cola, whatever.

So environment — different kinds of business environments are very different from each other. The more you can get out into the world, whether it’s through an internship or having some friends or your folks’ friends let you go shadow them for a week, is a very useful way of getting a landscape. Because when I was your age, I just didn’t know anything about anything. And even when we were selling software to these big companies, I didn’t know how they worked. I thought we’d be selling stuff like Microsoft — like 50 bucks a thing — and I realized no, you sell it at a million bucks a pop, and it’s a completely different world. And you need Arthur Andersen consultancy to sell them 5 million of consulting on top of your million in software. So we learned those things the hard way.

Tom: Cool. All right, let’s stop there and get a couple questions from the guys, and then I’ll wrap it up and we’ll get you out of here within an hour.

Student (question, paraphrased by Tom): One book…

Jeet: One book… well, if there’s one subject — maybe it’s not the book — there’s one subject that I would suggest that you understand. And it’s terribly badly taught. It’s taught as statistics and probability and so on. I think almost everything in the world… if you understand that if you look at the aggregate, it’s going to look a certain way, and at the individual level it’s not. Right? So it’s kind of like this… it’s the bell-curve concept.

You have to understand that when you look at a system — a society, economics, anything, leaves on a tree — the big picture is going to have a certain shape that you have to understand to understand the tree. But any individual leaf you pick is going to be different in its own kind of way. And understanding that at a deep level is a good way of understanding a lot of stuff. It’s understanding markets, understanding society, understanding politics. It’s like, “How could this be going on? How could someone be saying that?” Until you realize, well, there’s always someone saying everything — and what does that look like?

So as a topic, I think that’s the one where most people just don’t learn enough. And when it’s taught, it’s taught in such a horrible way in statistics and probability classes that it’s kind of incomprehensible. But if you study it in, like, biology, for instance, it’s more, “Oh, okay, I see what they’re getting at — here’s a patient population, what happens when you put in this cancer drug?”

So I’d say that’s super useful. I mean, there are probably a couple thousand books in the room here. I read a lot of stuff that’s history — history in economics and history in markets — and those are really useful books to read, because I think people don’t study history enough. They don’t realize that a lot of the things we’re thinking about — we’re not the first ones to think about it. They may have been thinking about it 2,000 years ago, and some of the answers are there and some of the questions are still there. And that’s true for politics as much as physics.

I read a lot of physics for a completely different reason — because those are my interests now. But yeah, let’s see. Yeah, speaking of the bell curve, I would read The Bell Curve. It’s probably one of the most significant works in social studies in the 20th century. Most people have never read it and condemn it without understanding what it’s actually about. So that’s not a bad book right there.

Tom: Two questions that I use to wrap it up. One: what’s your favorite movie?

Jeet: That’s a tough one. I love movies. It’s funny — when you’re young, you’re like, “Oh my God, this is my favorite movie.” And then, when you get older, you sort of go back and rewatch movies. And I was thinking about your question. And I think, quantitatively, I would say the movie I’ve seen again and again the most is Alien, which I think is one of the most perfectly built movies.

And also, I know a lot about how it was made. It was made on a very low budget, and they had to do all this wacky stuff to do the effects and it was kind of brilliant how Ridley Scott did it. And it’s kind of like… it’s a perfect science-fiction movie — I love science fiction — but it’s also a perfect horror movie. But it’s also set up so well about these blue-collar guys in the ship, in the Nostromo. So yeah, I guess I’d have to say, just quantitatively, I’ve seen Alien more times than any other movie — you know, The Godfather or Brazil or whatever.

Tom: Right. So the last question: if you want to leave the guys with one word to remember as they go out and try and conquer the world, what would the word be?

Jeet: Oh, yeah. The word is “we,” right? It’s not “me,” it’s “we.” And I think the teamwork thing — the teamwork dynamic — is, for me, the most important thing. Goes back to: what did I think about as the best thing I’m most proud of? It’s the team — the ATG team — which still today, you know, not only am I in touch with, but they still do stuff together, however many years it’s been later. So yeah, the word… I think the word is “we.”

Tom: Awesome, man. Well, thanks for spending an hour with us. A lot of fun, and thanks for being a teammate at ATG. It was an incredible journey together. And let’s catch up soon.

Jeet: Yeah, absolutely. Let’s do it. That’ll be fun.

Tom: All right. Talk to you later, man.

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Other Fireside Chats on The Good Men Project include:

David Kohan on Being Inspired by the Mediocrity of Others

James Kline on Banking, PE, Pro Hockey, and Wedding Crashers

Gregg Stone on Relentless Optimism in VC and Olympics

Kalil Diaz on How to Break Through Limiting Beliefs

Jeff Stevens on Discovering Your Why

Will Thorndike on the Power of Compounding in Investments, Relationships and in Life

Juan de Dios Aguilar on How to Lead, Who to Trust, and Why to Love

Ian MacGregor on Pro Bike Racing, the Secret Drink Mix, Going All In, and Founding Scratch Labs

Tom Macejko on Hunting, Banking, Private Equity, Pulp Fiction and Fulfillment

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You can find the full series on YouTube here:
@FiresideChatsWithTom

Watch for future episodes featuring more leaders from across industries. They all have their own compelling stories and are happy to give advice to the next generation of students, athletes and future business leaders.

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