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Winners of WealthTech: Drew Sievers

This month’s Winners of Wealthtech interview is with Drew Sievers, CEO of digital advice technology vendor Trizic. Drew is a serial entrepreneur and investor with a long history of developing innovative fintech solutions.

You can read my previous interviews with Catherine Flax, CEO of Pefin, Brian McLaughlin, CEO of RedtailAnil Arora, CEO of Envestnet | YodleeAngela Pecoraro, CEO of Advicent, Eric Clarke, CEO of Orion AdvisorBill Capuzzi, CEO of Apex ClearingLori Hardwick, President of Advisor Innovation LabsCheryl Nash, President of Fiserv Investment ServicesStuart DePina, President of Envestnet | TamaracBill Crager, President of Envestnet and Aaron Klein, CEO of Riskalyze.

I was inspired to start this series by one of my mentors, Tim Ferriss, who is a best-selling author, incredibly successful investor, entrepreneur, and podcaster. Actually, Tim doesn’t know that he’s one of my mentors, since we’ve never met. But his work and his writing have been a big influence on me, so I’m going to keep saying it until he tells me to stop. (By the way, I highly recommend Tim’s latest book, Tools of Titans, which you can buy online or even in a brick and mortar bookstore.)

The feedback on this series has been overwhelming! If you have a suggestion for someone you think I should interview, please send it to me at craig@ezragroup.co.

Can talk a bit about the previous fintech firms you started and why?

DS: Yeah, the most recent one (I have several) I have is a venture fund that invests in early-stage fintech. We’re investors in companies like SharesPostDigitEquidate, Boomtown, Abra, and a bunch of others. And the reason for that is to target really interesting, early stage fintech companies and then provide our operational expertise. That fund is called Operative Capital, it’s myself and a business partner of mine, a guy named Kelly Rodriques. Kelly is now the CEO of Equidate, but we’re both entrepreneurs who’ve done stuff over the years, and so that’s why we started that fund. That fund still operates; Trizic has an investment from Operative Capital, so the relationship is there.

CI: Early in your career you were working at Saatchi & Saatchi. How did you go from there into financial services?

DS: There was a plan. The plan wasn’t to get into fintech, the plan was to get into tech. So here’s how it all happened, in a very concise way. I was in advertising, and I realized as I was living in Japan with the internet starting to pick up, that mobile technology and internet technologies were going to be a big deal. My first venture was with another person, we started a firm called Saatchi & Saatchi Interactive. That was the early, early days where there was no real internet per se, it was Prodigy, America Online, and CompuServe, and we were creating stuff for brands. Once I saw that I was not going to ever own Saatchi & Saatchi Interactive, I said this is not what I want to do.

So I then went and worked as the President and then ultimately the CEO with my business partner now, Kelly Rodriques. He was the original founder and CEO of what was then called Novo Interactive (and then became Semaphore Partners), and in that business we built all the websites for big brands like Toyota, General Motors, Procter and Gamble, McKesson Healthcare, and then ultimately we built E-Trade’s first sites as well. So that was my first taste of some financial services, but I had successfully transitioned out of advertising to technology, which was my goal. I wanted to get out of advertising. Once we sold Semaphore Partners to Publicis, which is a large French holding company, I took a technology resource from Semaphore and a guy named Rodney Aiglstorfer, and we created mFoundry. Rodney had also lived in Japan, so both of us spoke Japanese and were very into Japanese culture, and we loved the mobile technology there. They had mobile payments already set up and running, so we got very interested in it. But we started the company first (this is before there was an iPhone) to be a write-once, run-everywhere development platform for mobile. Back in those days, you had J2ME, BREW, Windows Mobile, and you had to port everything; it was very difficult. We actually built this solution that allowed you to have one code base, and it ran everywhere.

We quickly realized that we had great technology, but we needed to pick a vertical. So I assessed three different verticals. I looked at being an Enterprise platform, but BlackBerry was THE platform there, so we were never going to get big there. I then looked at content and gaming, but the only people who were really making money there were the carriers. Then, one of my investors had an LP, which was Citibank, and Citibank was introduced to me, and that’s what changed mFoundry’s life. Citi came in and they said, we wanted to do mobile banking; what they called mobile banking 2.0. Because 1.0 was using WAP about 10 years prior. That was in the early days, and of course nobody used it because it was garbage. But what happened and what had changed were that the networks got much faster from a data perspective. So Citibank was my first banking customer, and as soon as I got them I went to my head of sales and I said, “I’m going to get rid of all of our other business.” We had about a million dollars in revenue at that point. I said I was going to resign all of it and that I wanted to focus 100% on banks. He freaked out, it was a Friday and he said, “I’ll get back to you, I’m too pissed off. I won all those deals.” He came back on Monday, he goes, “Dude, there were 14,000 banks and credit unions in the United States, I’m all in. Let’s go.”

So we pivoted the company, and we never looked back. We wound up creating the largest provider of mobile banking and payments in the United States. We built Starbucks card mobile, we did 1/3 of the top 50 banks in the country, and we ended up servicing 1,000 banks and credit unions before we sold it to one of our better channel partners, which was FIS. Coming out of that I formed Operative Capital, then coming out of that I got involved with Trizic. I dropped in as the CEO two years ago, and we’ve been refocusing the company. I’m very focused on, and I believe in, banks. So we tied up with FIS here and we have a strong relationship with them. We’re the company that is integrating into their trust accounting systems and doing account openings, and we have now multiple bank clients and we’ve built a huge pipeline.

I am all about enabling digital wealth technologies for the existing players. If we do our job, there’s no reason to have a B2C robo because your bank and your credit union should be able to offer you the exact same technology, and have a much lower cost of customer acquisition in the process.

Would Trizic be categorized as a TAMP?

DS: Yes and no. We have a couple of partners, one in the banking space who’s the fiduciary (we haven’t announced yet, so I can’t talk about that yet) who is going out and already selling banks, using our technology. We offer the whole thing. We also have a relationship that we have not announced with one of the top 10 asset managers in the world. We have a product partnership with them, so I’m not going to go down the path of creating a model marketplace. Most of these banks have their own product, but some of them do want some low costproduct. So we are tying up and having a relationship with a significant asset manager, where we will pre-package their models in our platform and then distribute those. The banks can use them for their mass affluent solution if they like, and then retain their own mutual funds or whatever else they want, from their own modeling and product perspective for their other clients.

CI: What was it about Trizic that made you want to take it over? You go to Operative Capital, you’re working on all kinds of cool products, you came from mobile banking, and this is very different than mobile banking. What was the one key thing that said, I’ve got to jump in, I’ve got to lead this company?

DS: Well I think it was a series of things. One thing was the CEO who was running it coming to me and saying, “Hey come run this.” I was looking at some other opportunities that were in payments actually, but the thing that I like about Trizic was it’s B2B focus., I’ve never believed that pure robo would be bigger than incumbent robo. I’m a huge fan of banks. I know people don’t like bankers, I can understand that. But I believe that community banks, and credit unions in particular, are an incredibly helpful, important part of the economy. And as naive as that may sound, I do believe that they are critical to the ecosystem. Community banks, credit unions, not just the big five; I think the big five are a whole different ballgame. I’m talking about, there are 13,000 or 14,000 of these things, and I believe that they are very important, very critical to the economy. And I believe that they have clients already, and they are best positioned to actually provide clients with wealth technology.

The thing that I’ve always liked about Trizic is it wasn’t saying, “We’re going to be a direct to consumer brand, and spend $1,000 to acquire a customer that won’t be able to pay off that acquisition cost for seven years.” That never rang true with me. What did ring true to me was the fact that having white label technology that enables the existing incumbents to more cost-effectively deliver the solution to their customer is to a) make more money themselves, and b) provide better service and a more cost-effective solution their customers. To me, that was a winning scenario. And the thing that you have to remember from my perspective was that, when you go to a user’s phone and you look at the top 10 applications, it’s always the same. You’ve got Facebook, Gmail or Google, Twitter. Mobile banking is also typically a top 5 app. So the customer acquisition cost to get somebody into something mobile, given that you already have some of the most valuable real estate in the world on this person’s phone via a bank icon, that to me was a no-brainer. That’s where I go, because those guys can acquire the customer for zero, they can get assets, they can retain it, and if they don’t do this they’re going to lose them, because somebody like Acorns or Robinhood is going to siphon the money out of there.

CI: It’s been two years that you’re at Trizic, so I guess the change of scenery was good for you?

DS: Yes, I’m an operator. I don’t like being a VC, but I do like operating. It is much better, and we’ve made a tremendous amount of progress in two years. This is a hard business, as you said; it’s not mobile banking. Mobile banking is not transactional in nature, I mean the Starbucks stuff we did was transactional, but mobile banking is not. With Trizic, these are regulated entities where we’re moving money, executing trades, doing all this sort of stuff. And the problem is it’s like you’re strapping a Tesla to an old combustion engine, right? It’s ridiculous, like you’re making electricity using combustion. Because there aren’t API’s everywhere; it’s unbelievable to me that everything is still file-based. Probably the biggest surprise to me coming out of payments, retail banking, and lending is the lack of availability of API’s, and how everything is built upon the exchange of files, which is crazy.

CI: Do you see that as an advantage for you, or a disadvantage?

DS: Neither; I think everybody is burdened by it, and I think that what some of the custodians are trying to do is to create API’s so that they can do what mobile carriers tried to do before the iPhone. And I think that’s a losing battle; some are trying to block their ecosystem and add value and not be dumb pipes, or however you want to phrase it. I think the challenge with that is they’re trying to collect tolls and everything else along the way and build these API’s and lock everybody out, but the file-based systems actually allow everybody to have a freewheeling approach to getting and moving data, because that exists and there are so many systems built on it. And while you may not be able to open an account in a particular custodian easily without an API, you can absolutely trade and move money and do everything else that you need to with these files. So from my perspective, everybody’s both burdened and able to leverage the file-based system. I think that it’s not what you really want to have long-term, but it’s what this system is faced with and based on.

How you identify people who are a good fit for Trizic?

DS: Well, some of the people are here already because we’re not just integrating into the wealth systems and portfolio management systems, we’re also integrating into core banking systems and other things as well, because we have a bigger vision around what we want to do. We do have employees who actually left mFoundry years ago to do something else and are now resurfacing. What we look for in the engineering team specifically is we look for people who have full stack knowledge, with some specialization. We also are only looking for people on the main systems. When we’re talking about the integrations teams, that group has to have experience doing integrations into financial systems. It doesn’t matter whether it’s a payment system or an ACH-based system or it’s a core banking system, or it’s an ATM network, the ISO network, whatever. We want to make sure they understand how to handle and work within financial services and all of that, so that’s critical on that side. On the management team, Jen came from Blackrock, John Carey (who is our product guy) came out of FolioDynamix. Steve Lewczyk, who is running my sales, he came out of out of wealth as well; he came out of Fidelity and he also ran his own hedge fund technology company.

How do you stay motivated and keep your entrepreneurial spirit going?

DS: It’s a couple of things. Retirement is pretty boring, is what I will tell you. Not working is horribly boring. And to be really candid, it can threaten your marriage. Because all of a sudden you’re home and your wife’s like, what are you doing here? I’m not the CEO of the house, is what you find out very quickly. So the way I get motivated is really straightforward, which is I have to believe in what I’m doing, and believe that it’s an interesting product that is valuable. In this case, it’s a no-brainer. I think wealth is one of the most dysfunctional technology businesses I’ve ever encountered. So I get motivated by that, because I think the opportunity is huge; it’s a multi-billion dollar opportunity.

But then secondarily, and probably more importantly, (and this is totally cliche) it’s the people. And I have got a great team of people. It’s just starting to get to this point, we just got this team in place now and everything is starting to hum. I’m now actually being able to go up a level and get less tactical and get much more strategic, and that’s where I’m at my happiest. I have this team below that’s doing everything, executing, making the stuff happen. They’re strategic as well, but they’ve got a job to do in terms of getting these banks live and getting all these systems done and everything else, and getting the company marketed. But now I’m able to step back and say, where do I want to take this? Now that we’ve got the foundations built and we’ve got certain things that other people don’t have, how do we exploit those and take them and leverage them to do something really important and dynamic? And that’s what gets me excited. Plus, I get to wear shorts to work; I’m in shorts and flip-flops. I’m a horrible employee if I’m working for someone, and I much prefer working for myself and wearing shorts and flip-flops to work.

How do you maintain your work-life balance?

DS: Well, this is my third or fourth start-up. The most important employee in this company is the person who’s not employed, which is my wife. I sound like I’m running for office, but it’s absolutely true. Because ultimately, you need to have very clear divisions around who’s doing what. For me, I get in between 6 and 7 in the morning but I leave by around 5:00. That way I can get home, see my family, have dinner, and then I’m going to do work in the evening anyway. I have one in college now and the other a senior in high school, 18 and 20, so I’m a guy who has time in the evenings to do some more work. It allows me to find that balance, but also I’m pretty disciplined; I get up at 5:00 in the morning, I go swim, I get to work and I do my work, and then I get home and I’m with the family, and that’s mostly it. It’s not the most exciting life I guess, but I figured out the work balance thing a long time ago because I’m 53 years old, I’m not 30.

What’s your morning routine?

DS: I either get up and swim (I do Masters Swimming four days a week.) Masters Swimming is a program where you have coaches and you swim maybe three or four thousand yards at 5:45 in the morning with 30 or 40 other people as part of a team. So I do that or I go surfing before work, or I go to work. My only exercise really is swimming, surfing, and walking. Those are the three things that I do.

What’s the most important thing you learned about success in the software business?

DS: Well, two things: is there a product market fit, and do you have a great technologist? That’s it. If you have a great technologist and there’s a product market fit, you can work everything else out. But if the foundation of the company is built on rickety technology, it doesn’t matter how good the product market fit is, you’re S.O.L. By the same token, you may have the best technology in the world, but if there isn’t a product market fit or a demand for your product it doesn’t matter. So if you have those two things, you can wrap everything else around it: sales, marketing, fundraising. At its core though, you have to have that. Then you build the team around it. But that technology hire? When I started mFoundry I had Rodney, he was brilliant, he was great. At Trizic we had Steve Mays as the founding architect when I got here. Before that, at Novo, which was Semaphore Partners (which was a software company too) we had Jim Ruggiero, and he was phenomenal. He then became the CTO at Pensco Trust.

Kelly and I have done well because of the engineers; that one engineer that you need, who understands the architecture and makes the right decisions. I’ve been involved with companies as an investor where the underlying technology decisions, the architectural decisions that were made, were horribly flawed or ill-informed. I’ve also seen companies that have missed out on huge opportunities, where they were so well positioned to be successful, had a great team, but the technology was garbage. So if you have those two things, there’s demand for the product and you’ve got a great technologist, then you have what you need; you just need to wrap the rest around in it. Obviously it can still go sideways quite easily on all the rest as well, but you can’t do anything without those two things.

What’s become more important to you in your personal life over the past few years?

DS: Well obviously spending time with my kids as much as I can, and as much as they’ll let me, right? I mean you know, you’ve been through teenagers. The horrible tragedy of the teen years is that you want to spend as much time with your kids as you can because they’re leaving, and they want to spend as little time with you as they can, because they’re leaving. It’s one of the saddest parts of parenting, I would say. So for me, it’s been trying to spend time doing that. But on the other side, the great part has been that I have a great relationship; this will be my 28th year of marriage here. I have a great wife,a really great partner. So what’s been neat for me the last few years is as the kids have been going out, she’s been re-engaging herself in amazing things that she’s doing. And it’s been great for both of us together, because it’s like we’re getting reacquainted. You’ve been through this, I’m sure, but you start to have discussions about stuff that isn’t your kids, which is really nice.

What would your close friends say that you are exceptionally good at?

DS: Good question. Two things: I’m fiercely loyal to my close friends, and I’m super tenacious. You know, I’m not a huge guy. I have two nicknames that I’ve been given by my friends: one is the terrier, and the other one is the mosquito. So that gives you an idea of my personality.

Are there any new behaviors or beliefs you’ve adopted recently?

DS: Aside from getting old and trying to stay healthy, workwise I would say I try to get out of the way now and let my team do what they want to do. Now there are times, as they’ll tell you (right now is one of those times) where I’m dropping down and engaging on a couple of mission critical things that are important to the company. I’ll be there in excruciating levels of detail, and I know it’s probably horrific. On the other hand, one thing I’ve really worked on is allowing them to do what they can do so that I can do what I want to do. So that’s evolved, you know when I was a young CEO I was involved in every single aspect of the business. I felt like if I wasn’t doing that I was failing, and it took years for me to start to realize that as you become the CEO, you get better at picking the right things to do. So that’s one critical belief. Then I have other beliefs as it relates to social causes and things like that, which are more personal, but work-related that’s for sure.

CI: Let’s talk about on a personal note.

DS: Well I’m a huge water person, obviously, I swim, I surf, I fish. So for me, my causes are Surfrider FoundationHeal the Bay, and anything that I can do related to preserving the oceans and ensuring that they’re healthy, right? Because they’re the lungs of the planet. Then I have strong views on a couple other things, which I don’t bring out in a public forum. Only because it can impact your business, so it’s one of those things where when I’m done with business I will drop in.

Who was your biggest influence growing up?

DS: My biggest influence growing up was my father, but probably not in the way that is traditional. My father was an entrepreneur (he’s retired now) and he worked his ass off. He had a business, it was a market research firm, and he worked so hard and had good years and bad years. But the problem with that business was that it was not leverageable. Unless you were J.D. Power, it was very hard to create any leverage in that business, or to create any wealth for yourself. Because it was always bill by the hour, and he was the business.

My brother and I were just talking about this the other day, I have memories of my dad working downstairs in the middle of the night. That’s what he did, so I got a strong work ethic from him for sure. He’s also a super independent guy, he grew up in the Panama Canal Zone and basically had this kind of Huckleberry Finn life. He’s very independent-minded, he worked with his hands a lot when he was younger. Me, I’m an independent problem solver. This is where I’m different from my wife; my wife prefers to have a teacher when she’s learning. And I’m the opposite, I really enjoy (when there’s a problem) figuring it all out on my own, which is a little annoying for a lot of people and my wife, but I really do enjoy that. I get that from my dad, and his work ethic.

We’re a multi-generational entrepreneurial family; my grandfather was an entrepreneur and his father was an entrepreneur, we were German bakers. We had our own bakeries, and then we didn’t insure them and they burned down, and then we were done. So there are all sorts of lessons. But yes, I would say my dad, because he was so influential for me at that time.

Who do you think of when you hear the word successful?

DS: Successful is such a loaded word. Because successful, what does that mean? Right? To some people, success is if you’re a Kardashian. Honestly, I’ll tell you the picture that immediately appeared in my mind, it’s so ridiculous, but it’s Kelly Slater. You’ve probably never heard of him, but Kelly Slater is the 11 or 12-time world champion of surfing. I’d love to give you a better answer, but if you’re asking the first thing to come to my mind, it’s him. He is the LeBron James of surfing. I’ve been surfing for 40 years, it’s a big part of my life, and this guy is extraordinary. He won his last title in his forties, he’s a little bit younger than me now, and he’s incredibly fit and healthy, and just a professional and a great businessman. He’s an extraordinary person.

To me, he’s extraordinary because of the way he lives, what he does, and his example that he sets. He’s never put himself into a compromising position, like other athletes.

Is there anything you believe that other people might think is crazy?

DS: Probably. I’m a big fan of physics and astrophysics, if you want to get totally crazy. I do believe there is life on other planets. Not necessarily intelligent life, but there’s definitely life on other planets, no doubt in my mind.

CI: Just based on the sheer number of planets.

DS: Yes, the law of large numbers says this should happen. And I do believe there’s probably some form of quasi-intelligent life around, there might even be intelligent life. But I definitely believe that in my children’s lifetime (and quite possibly in mine) we will see some form of extraterrestrial life like bacteria, lichen, whatever. Based on the last stuff that came out of Mars and the fact that they actually did find that there is water underneath. Water is a fundamental building block, so that’s a big deal. But then all the Kepler work, so yeah I love all of that stuff. Astronomy is also one of my passions, so I do believe that. I know there are a lot of people who believe that earth is the center of the universe and everything starts and stops here, we’re the best and yadda yadda yadda. But the reality is, there’s way too much going on out there that we don’t know, and I’m pretty confident that it’ll be discovered in the not too distant future.

CI: The problem is of time and distance. Yes, there could be intelligent life somewhere. But if it’s a thousand light years away, we’re never going to find out about it.

DS: No, that’s exactly right. That is the issue. That’s what shows me, you start to look at the Goldilocks planets, of which they’ve identified billions now.

CI: Or if they are intelligent, what if their development of the right technology is a thousand years ahead or behind us?

DS: That’s exactly right. That’s why there’s so much stuff scanning for radio waves, etc. I’m not talking about extraterrestrials in the sense of you a Hollywood sort of thing. I’m more talking about something bacteria-like; there’s going to be some fundamental, carbon-based building blocks that exist in these places, because they could. Intelligent life here is great, and there may be intelligent life way away, and we would just never know. They could have died out 500 lightyears away, and we’ll get their radio waves later.

What bad advice do you hear being given out most often?

DS: In my world of technology, there’s so much bad advice out there. I think the number one thing that I see is really tied to fundraising, when companies are trying to raise money. People getting bad advice around what it takes to raise capital. And the hard part is that when you go to raise money for some of these companies, you have to have the right story. And the CEO ultimately is the storyteller; you’re telling a story and you want to captivate your audience, you want your audience to believe in the story the same way that you believe in it. But sometimes what people say is, “Hey you need a 30 or 40 page, super detailed business plan or deck to go raise money.” I hear that a lot from people, and I think that’s some of the worst advice. Because almost always, they don’t get money. So I always try to counsel these entrepreneurs, if you can’t summarize and get people excited in 10 or 12 slides, then you’re not going to get the money. You might get it from your family, but you’re not going to get it from a professional investor.

Are there any favorite apps that you’ve found recently to be helpful or make you more efficient?

DS: Oh yeah, the best app that I have is Things for Mac. It’s so simple, it’s just a task-tracking piece of software, but it’s critical to my life. I depend on it so incredibly, and the reason is it does two things. The average task program allows you to set your due date for when something’s due, so for example you say hey I’ve got this board meeting, and the deck needs to be done and shipped out two days before the board meeting. So you set a due date. But the problem is, it doesn’t show up in your task list until the day it’s due. Or you end up with a thousand tasks. What’s great about Things is it allows you to set your start workday, when you need to actually do the work, as opposed to when it’s due.

To me, that was life-changing. I’m sure software has improved for everybody, but for me this was critical. I use the software and it pretty much rules my life now, because I’m trying to manage so many different streams of work, and that’s a critical piece. The other piece that I can’t live without for sure is Spotify.

CI: Spotify’s a good one. So you’re a Mac user?

DS: I am a Mac user. It’s funny, when I was in advertising I worked on the launch of Windows 95, and I was miserable. I’ve always been a Mac guy, since the very first ones came out when I was a kid. So when I got put on the account for Microsoft, it was like asking somebody who hates guns to work on the launch of the next line of Winchester rifles.

Do you gift any books, and if you do what’s the most common book you gift?

DS: Well I’m a big reader; I read about a book a week, and I track everything. Talk about another app that I use which I love, is Good Reads.

CI: Good Reads?why we sleep 199x300 - Winners of WealthTech: Drew Sievers

DS: Yes, Good Reads is awesome. So if I gift a book, there’s one book for sure that I will gift, and it’s “A Universe from Nothing.” It is Lawrence Krauss. It’s a great book, I think it’s a more approachable and contemporary version of “A Brief History of Time,” it’s a great physics book. The other book that I’ve been gifting recently and telling people about is this book “Why We Sleep,” which I heard about on NPR. It’s by Matthew Walker and it is awesome, it really gets into how much sleep you need, why you need it, life expectancy if you don’t get enough sleep, all this stuff. A really good book.

I have lots of favorite authors so I flip between different genres all the time, I like history and I like this, but I also read complete garbage. I’ll read the entire Brad Thor “Harvath” series, then Lincoln Rhyme series, and then I’ll read the Lucas Davenport series. I like spy books and thriller books, I like the Silva books about the Israeli guy. Those are the things I can read before bed to calm down and detach.

CI: Are there any business books that you gift or you like?

DS: No, I hate business books. They’re boring.  I mean there are some good ones, John Doer wrote one called Measure What Matters a while back that  I thought was pretty good. But ultimately, I’d rather inject Windex in my veins than read a business book. I’d much rather just do business and talk to people.

CI: So you just get all of your wisdom organically, empirically?chasm 202x300 - Winners of WealthTech: Drew Sievers

DS: Lots of failures, lots of mistakes. That’s the best teacher for me. Also, a lot of time these books are not written by people who’ve actually done any operating. The last book that I read that was a business book that I thought was great was Clayton Christiansen’s “Crossing the Chasm.” That was a great book, and I still use that model today in my head for multiple things. That was the last good one that I read. And then it’s like, I don’t have a lot of time. So why would I go home and read business books, when I can just escape into the life of an Israeli assassin? That sounds way cooler and more interesting to me than here’s a great way to run status meetings.

If you could send a message back to your 25-year-old self, what would it be?

DS: Get a night guard for your teeth, because all those years of stress make you grind your teeth. And get out of advertising sooner.

Would you change that message if you were sending it to your 35-year-old self?

DS: No, my 35-year-old self I would have said stretch more for the house that you’re buying, instead of the one I settled for.

What was the failure that you learned the most from and why?

DS: Well my favorite failure was a sequence of micro failures, which was the first time I really went out to raise money for a company by myself, notwith another person. That was the early days of mFoundry, so we’re talking early 2000’s. And every meeting was a failure. I would fail, and then I would go back to my desk and say, “These guys aren’t giving me money.” The smart thing I did at least is at the end I would say, “Okay you’re not going to give me the money, I get that. Why not?” And then they would tell me, and I would tweak my presentation to address that point. Then I would go to the next guy and the next guy would go, yeah I’m not doing it. And I’d ask why, he would tell me, and I’d go tweak the deck again. I kid you not, I talked to 30 or 40 different VCs before I finally got to the one where he said, “You know what? You’ve answered all our questions.”

Do you have a favorite movie?

Oh, yeah. Jaws. It’s such a good movie. What’s great about Jaws is it’s a classic struggle of the sea, which for me is always rich fodder in an area that I love. Because I love sharks, I love everything about the ocean. Number two, the script is great. The dialogue is fantastic in that movie. And yes, there’s a mechanical shark that looks ridiculous, but that’s actually just become endearing to me over the years. But great, great acting.

You’ve got Robert Shaw doing his bit on the USS Indianapolis, which is phenomenal. It was Spielberg’s first big success, and it was the cause of the summer blockbuster. It was the first real summer blockbuster and it scared people out of the ocean, which made surfing better for me. There were less people in the ocean, for a season.

CI: It kept people away.

DS: It did, it did. I think I was probably 11 when it came out, I think it was 1976 that it came out. I still watch it at least once a year, I just watched it with my whole family in Nantucket in fact, and it still made people scream.

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