Rylan Hamilton shares his experience selling a company to Shopify for $450M. He also discusses his journey of raising $60M to build autonomous ships.
Rylan Hamilton shares his experience selling a company to Shopify for $450M. He also discusses his journey of raising $60M to build autonomous ships.
be ambitious because you only get one chance to decide on the start of the mission that you want to go on. And so just be very like deliberate about what [music] you start because once you start it, there's no turning back. Uh and you're going to be on that journey for [music] all righty. Hello everyone and welcome to the Dealmaker Show. So today we have an amazing guest joining us. I mean, we're going to be talking about all the good stuff that we like to hear you when it comes to building, scaling, and also exiting. You know, his last company was quite a success, one of those 10x, you know, and more, you know, for some other investors. But we're going to be hearing all the ins and outs. We're going to be talking about what happened, you know, when he went to the Navy, uh some of the other stuff like raising money as well as how to create a a vessel, you know, that is autonomous that
goes on its own up in the ocean. So, uh, again, brace yourself for quite the inspiring conversation. And without further ado, let's welcome our guest today, Ryland Hamilton. Welcome to the show. >> All right. Thanks for having me. >> So, originally born and raised in Boston, Massachusetts. So, give us a walk through Memory Lane. How was life growing up for you? >> Uh, I love growing up in Boston. I actually grew up right next to the Freedom Trail, but I never really did the whole Freedom Trail sort of from start to finish. But it's a great city. um great universities just and what I love about the city and uh I know you're from around the greater New York City area, but we have people who work in at universities, people who work in technology, we have doctors. It's just it was a great environment to grow up in. >> Now, I know that for you, you ended up going to
Harvard and one of the good things there is that you were able to experience and test things out. I mean one of them for example even working you know in in in finance you also got a taste of startups too. So tell us you know what were you testing there when it cames to more the career you know side of things and and what kind of like sparked you know like that decision on what would be the the path to follow you know after that. >> Yeah. If I go back to the 20-year-old Ryland uh at Harvard I really didn't know what I wanted to do. The most common jobs uh back then were either being in consulting or being in some type of finance role. And so I actually had the opportunity to have an internship in finance in New York City. Uh and I surrounded myself with amazing people. I learned a ton, but I realized after that summer that it just wasn't really the calling for me. I wasn't kind of
designed to be behind a computer from 9 to5 or even for much longer hours doing spreadsheets all day long. Uh and actually a couple weeks after I left that job uh in New York City, 911 happened and I actually worked in an office that was looking at the um the World Trade Center uh the towers that were there. And so at that moment it kind of really shook me up and I said there's got to be something else that I want to do with my life. Uh and a couple you know a year later I ended up joining the Navy. >> Obviously you know you had it in the family too. Your father was in the Navy, your grandfather was too. >> So tell us how was that experience for you? I mean, that sounds quite like the the forming, you know, experience. No. And and probably crazy stuff that that you experienced. >> It definitely was one of the best decisions I've ever made in my life. Um, but it wasn't
obvious at the time. Uh, so as you mentioned, my grandfather served in the Pacific. Uh, my father actually went to the Naval Academy and was on nuclear submarines in the 60s, but he passed away when I was younger. So, I didn't kind of grow up with that kind of legacy around sort of the dining room table. And my adoptive father at the time when I told him I was considering kind of joining the Navy, he's like, it just didn't make sense to him. He's like, you're at Harvard right now, like no one from Harvard joins the Navy. And I said, 'Well, why do you think it's a bad idea or what are you thinking? He's like, well, why don't you talk to all my friends who are in the Navy and they can give you some career advice. And so I talked to all his friends who'd been in the Navy and they all said like, join the Navy. It'll be the best decision you ever do. So I kind of jumped into that decision.
Uh, but I had amazing experience. And so I found myself going from school in Boston, Massachusetts to six months later I was at officer candidate school in Pensacola, Florida with a shaved head uh and trying to figure out, you know, what this whole experience would be like >> and obviously going around the world too. So how was that experience of being deployed in in some of those areas that were not as as as pleasant, you know, to to be in, you know, with all types of crazy stuff around you? >> It was. So, the first ship that I was on was an amphibious transport ship. And I just finished, as I mentioned, Officer Can School in Pensacola, Florida. And I flew out to meet the ship in the Persian Gulf. Uh, and it was just before we invaded oper uh, you know, Iraq at the time. And it was called Operation Iraqi Freedom. And so, here I was on a ship and the ship was offloading
Marines and all their equipment. And then it moved into doing some mind sweeping. And this was like my experience for the first couple weeks of being on a real Navy ship. and just basically drinking from the fire hose trying to learn how to do this job. In fact, the first day that I was on a ship in the Persian Gulf, the Iranians actually fired some missiles and the whole ship went to general quarters. And so at that time, because I just, you know, flown in on a helicopter, the ship, I was still in my civilian kind of garment or clothing. And I was basically running around the ship and an officer grabbed me and said, he said, "En Hamilton, it doesn't look like you know what you're doing." He grabbed me and pulled me into a room. And that was like my first kind of experience of being in in the Navy. But uh started off in the Persian Gulf, had an experience to go through the Suez Canal,
the Panama Canal, and then I ended my naval career being in the Eastern Pacific doing counter narco terrorism operations on a frigot. >> I remember the um reading the book Extreme Ownership. Uh I don't know if you've had the chance to read it, but it's a phenomenal book. I guess one thing that comes to mind now is what do you think that experience gave you uh in terms of like the top three things that you apply uh on the way that you approach life and perhaps business? >> Yeah. So ownership is definitely one of them. When you're on a ship or when you're in the military, you can't just necessarily take no for an answer or if something doesn't work say I guess it doesn't work. like you're literally on a ship with your shipmates in the middle of the ocean and you just have to make sure everything works that the whole team kind of operates uh you know cohesively. Uh so
ownership's one. Um the second is leading from the front. You have to be uh willing to do the job uh and kind of show people that you're willing to do whatever it takes. You can roll up your sleeves. You can work the long hours because if you're not willing to do that work, why would anyone who was working for you be willing to do that? And then the third thing what I really appreciate from the Navy is and it's kind of like being at a startup. Uh I'd call it this wardroom mentality where when you're in the Navy, everyone like you know what everyone makes like literally your salary is posted on the wall. So it's not about getting promoted. It's not about a bonus or anything. It's just like we're all in this room together. How do we make this work and what's the mission that's important? And so it really removes a lot of the politics and kind of other layers of bureaucracy that you get in
bigger companies. And I feel like you have the same sense of camaraderie when you're at a startup. It's like we're all in this room, titles don't matter and like what does it take to make this work. Whereas, you know, sometimes if you work at a big company and people are really kind of, you know, they care about their promotion, they care about their titles, they care about stuff that's really not as important to the mission. So then you got out of the new of the Navy and then you uh married your you married your college sweetheart and then you know you you went at it now on the on the professional side of things with start you started working at KA systems which was quite also quite pivotal for you because you know the company ended up getting acquired then you launched your first company which was a smashing exit to a smashing success I guess how was that experience too with KA systems
you know like what…