WSO Podcast | E191: Middlebury College to Goldman Sachs Internship to FinTech Startups
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In this episode, we follow Alex on his winding road through various VC and IB internships in college, including one at Goldman Sachs to his latest jump to the fintech space at Lex Markets. Learn what went wrong at the Goldman internship and the first start-up and advice to some of the younger listeners trying to navigate similar waters.
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WSO Podcast Episode 191 Transcripts:
Patrick (CEO of WSO): [00:00:06] Hello and welcome. I'm Patrick Curtis, your host and chief monkey, and this is the Wall Street Oasis podcast. Join me! As I talked to some of the community's most successful and inspirational members to gain valuable insight into different career paths and life in general. Let's get to it. In this episode, we follow Alex on his winding road through various B.S. and eye internships in college, including one at Goldman Sachs to his latest jump to the fintech space at Lex Markets. Learn what went wrong at the Goldman internship and the first start-up, and advice to some of the younger listeners trying to navigate similar waters. Enjoy. Ok, Alex, thanks so much for joining the Wall Street Oasis podcast.
Alex: [00:00:55] Yeah, thank you for having me.
Patrick (CEO of WSO): [00:00:56] Be great if you could just give the listeners a short summary bio.
Alex: [00:01:00] Yeah. So I work for a real estate investment banking fintech. Previously was at a fintech debt fund kind of thing, lending operation and licensing out software. And before that had a string of investment banking, internships and the like, both in New York and London. A little bit of political experience earlier on, but have mostly been on the finance track. And way back when I was at Middlebury.
Patrick (CEO of WSO): [00:01:26] Awesome. Thanks for thanks for that. So let's talk about your time. Back in Middlebury, I went to Williams so familiar with the liberal arts. I would love to hear just, you know when you went to school, were you thinking finance? And I know who. I know you're who. I worked with your father. Just for the readers to know I. Alice's father was at tailwind where I worked way back when. But yeah, I'd love to hear just. Was he an influence of you saying, like, oh, you should go to finance? Or was there family members that were in finance?
Alex: [00:02:00] Yeah, I mean, he was definitely an influence. It was never. It was never coached, but it was one of those things of. And you probably know from Bell End of it always came home. Right. It was a nonstop job. And so I was around it growing up and, you know, had a lot of exposure growing up through my dad. And then later on in high school, I'd say, you know, a good portion of people's parents either worked in corporate law or in finance of some sort. And so there's a lot of exposure all around. I started interning back in high school, so my high school actually had an internship placement program and I was entering that R.V.S and Barclays before I was 18, which was a great experience just to have a foot in the door. Your high school did that. Yeah.
Patrick (CEO of WSO): [00:02:38] How was that? I've never heard of that. So that young. It like a rotate or rotation? Or was it a real internship?
Alex: [00:02:44] Somewhere in the middle, I mean, look, these were these very, you know, banks agreed to take out a high school student for three or four weeks or whatever. So, you know, the expectations are obviously pretty low and it's, you know, You're not actually working on real stuff, but you get to be in the office and meet people and be a part of it. And you know, you sort of get an early flavor. The school sort of organized for us and there were still, you know, you apply this quarter resonate workshops. So I started pretty early on the track with that.
Patrick (CEO of WSO): [00:03:09] Just to your high school or do you know if there's other high school programs that do that?
Alex: [00:03:12] I haven't heard of another high school that does that. I think that that may have been unique to my high school. And it was a great opportunity. I grew up in London and that was, you know, we just, you know, hop on the tube and go over to Canary Wharf and intern over the summer.
Patrick (CEO of WSO): [00:03:23] I am in London. Ok, yeah. Yeah, so very cool. Yeah, tell me a little bit about that. That's before we even dive in. What do you mean? You grew up in London and what's the background there?
Alex: [00:03:32] Yeah. So as you said, you worked with my dad at Tailwind and my dad left tailwind to go and take a job over in the UK and moved the family over with him. So I went to the American school in London and call London home. My dad is actually still there and, you know, got an American high school experience with a bunch of, I would say, 50 percent plus ish Americans and everyone else Americanized. And yeah, had had a sort of interesting experience being sort of a third culture kid, I guess they call it. And, you know, very different than where I was in the New York area before that. But, you know, very glad I did it and got me sort of a lot of international exposure early on. I also played rugby and travel all over Europe, so it really got the travel in my teens and was pretty formative on my life going forwards.
Patrick (CEO of WSO): [00:04:21] That's lucky. Yeah, that's amazing. So you're kind of getting out of high school, you're applying to colleges, you end up at Middlebury. Do you think at this point, Hey, you've done, you've worked at some banks. Were you thinking, hey, investment banking all the way when you were?
Alex: [00:04:36] I was. I was dead set from day one, and it was a joke amongst my friends from day one. So, so I. I threw my Barclays internship, had some, you know, personal connections. I thought I was going to go back and there is some turnover at Barclays in 2014, and the guys that I knew there didn't go back. And so my sort of freshman year idea sort of evaporated in mid air and freshman summer. You mean, for my freshman summer, I was hoping to go back and have that be organized and have, you know, really sort of solid thing to go down that road as a freshman? Yeah, totally evaporated in late April of my freshman spring and totally by chance. You know, someone I knew met someone walking their dogs in the park and Rock Creek Park in D.C., whose daughter was on the early days of the Clinton campaign. And they need it and someone had dropped out. They needed someone. And so I sort of just fell into a clinton campaign internship for my freshman year. Summer it was my brief diversion from banking.
Patrick (CEO of WSO): [00:05:42] That's actually a really interesting topic, simply for the fact of like resume building and politics. And, you know, the thought of, do you put that on your resume or do you? Well, that's
Alex: [00:05:54] Exactly it was on the resume through up until the twenty sixteen election and then it fell off. But it isn't. Hey, it is still on my LinkedIn way down there at the bottom. So if someone really wants to know they can go, look at it. But yeah, it's a sensitive topic, depending on who
Patrick (CEO of WSO): [00:06:10] Would you recommend putting that for four people who do work in politics or campaigns if do you feel like it's
Alex: [00:06:18] I think it's helpful, I think depends on what you're doing and who you're working for. Right? I mean, I don't want to get too political on this podcast. There are certain politicians that are particularly inflammatory that I would maybe be worried about. Yeah, to be honest, I was on the fence about Hillary Clinton. I think that was a lot that was a very sort of sore topic for a while, but it was a really great experience to have an 18, 19 years old. And I got I really stepped up in that internship. They gave me a lot of responsibility, and so I was able to speak to that. Yeah, yeah, yeah. I was the organizer for the East Coast for them, you know, volunteering out of the D.C. office and the end. So that was, you know, that was a really sort of cool thing to talk about for a while.
Patrick (CEO of WSO): [00:06:55] Yeah, for sure. Ok, so you're doing that. You come into sophomore year and now you're thinking, Okay, for sure, I'm going to have this investment banking Internship, sophomore
Alex: [00:07:03] Summer school sophomore year. I came in the part where my friends made fun of me over the sophomore was the banks started networking at Middlebury. We had on-campus recruiting early, early on and it's not class-exclusive, but it tends to be attended to be juniors. Now it's probably sophomore. All the process works and I went as a freshman and I think it took me probably two or three years to live down going to those events as freshmen. So on the focus of that, that was, you know, something in there as well. Yeah, sophomore year I came in still dedicated towards it. I had done a bunch of networking starting in those sort of freshmen coffee chats on campus. And whatnot, and you
Patrick (CEO of WSO): [00:07:46] Know, with that, what do you mean? The networking freshman coffee chat says, like, I know you went to the info sessions, but were you doing other stuff like Middlebury alums that were or were in banking? Were you already putting in the ground?
Alex: [00:07:58] I did get to that in the end, not as a freshman. It was much more talking to people on campus and talking to people they might know and using my dad's connections and high school connections and sort of anyone that I knew. I think it was really there was a lot of hustle that went into getting my sophomore internship, probably more than any other internship, to be honest, because there's not really if you're not a diversity candidate. There's no structured process for sophomores. And it was the sort of really,
Patrick (CEO of WSO): [00:08:23] You know, accelerated at least back then there was no accelerated.
Alex: [00:08:26] Yeah, exactly. It was not even that accelerated. They wouldn't even take your application, right? I mean, you couldn't get into anywhere big unless someone reached out and pulled you in. And so there is a lot of pounding the pavement cold emails going through the Middlebury network again, high school friends and dads, friends and anyone of that on-campus and anyone, anything I could think of to just talk to someone. And I think I did. I think I found my spot in late January, early February of sophomore year. Yeah. And what was it? And how did you find it? It was. It was a friend of my dad's who had a son who he'd introduced me to a while back and I reconnected with the son, who is, I think he's about 10 years older than me. So, you know, somewhere in the middle there and they were his venture fund was this tiny little thing at the time. It was, you know, two partners, maybe three partners and two associates, and they wanted to go bring on a handful of interns for the summer. But I had a whole process to navigate because they there's a whole bunch of laws about like college credit. If you're going to pay your interns, you have to give college credit. And Middlebury refuses to take college credit, or at least did. And so it was this awkward thing of, well, they're not going to pay me and they can't give me college credit. And how are they going to take me? We ended up figuring it out, but went over and it was funny. It was. It was a know British internship and went back to the Uk, all american intern class. And again, I still look back at it. Incredibly, incredibly funny. That was one of the really formative experiences of my career because I loved that summer. And it's crazy because at the time, like I said, they
Patrick (CEO of WSO): [00:10:01] Hire all American interns. So it was just that was the class that they wanted to bring over or something.
Alex: [00:10:05] I, you know, I never got that far into that. I think it was a combination of they didn't have to pay them and they were people, people in network. They had the college, the college credit thing, it worked out. But the crazy part now is, well, it was a small fund. Then they're now the largest retail venture capital fund in Europe, I believe. Wow. And the guy I was working with really great guys and I got to learn a ton. And even as an intern, you know, they had me on the investment team and I'm learning how to screen pitches and learning how start-ups work. And then they started to realize, Well, actually, maybe Alex can be operational too. And they started putting me in because they run a Y Combinator style fund over there where they bring they literally share an office space with these, you know, firms they invest in to. You have the venture fund upstairs and all the start-ups downstairs, so you walk downstairs and go and consult with some of these guys. And I was doing a sort of split day a week thing, so I got a really cool experience being on the ground floor of start-ups and being on the investment side as well and learning both sides of business. And again, with really, really great people who I'm still in contact with and really were formative for me.
Patrick (CEO of WSO): [00:11:12] That's amazing. So besides, like having good connections and connecting with that sun, for people who don't have that, what do you suggest like they do to develop those relationships?
Alex: [00:11:25] Yeah, I mean, it's really hard. And you know, like I said, like you sort of said, I got very lucky that I was able to come in with some of those connections. The people that I knew that sort of did well. Without that, we all sort of followed the same process. I sort of struck gold because I had an extra bump, but I think everyone sort of did the same thing I did. You just talked to as many people as possible. And I think if you're very open with what you want and you talk to, you talk to as many people, honestly, and you're interesting. Eventually, someone connects you. And so I know there was actually quite funny. My first week of freshman year like literally orientation. There were three in my class Middlebury. I was fab. So this class of 100 people, we have our own orientation. The three of us in this orientation all said to each other the first like three or four days of school that we're all going to work at Goldman Sachs and all three of us went to go. And all three of us left. But the other two guys who were in that as well, they did the same thing, right? I don't think they came in with the same sort of connections, but they really grounded out and they got involved on campus. They met other people. They got introductions. A lot, a lot, a lot of cold emails.
Patrick (CEO of WSO): [00:12:35] Give me a sense, give me a sense of that, like the scale of it so people can kind of wrap their head around it. Like when you were coming into sophomore, you're like, how many? How many? Phone calls or how many emails are LinkedIn requests, did you send out and then how many phone calls that turn into before like,
Alex: [00:12:48] I had a spreadsheet of about two hundred and fifty or three hundred people that I had researched and wanted to go and talk to. And I emailed every single one of them.
Patrick (CEO of WSO): [00:12:58] Let's back up, though. How do you even form that list? Was it LinkedIn filtered searches like?
Alex: [00:13:02] Well, it started with the Middlebury Alumni Network, and I went through the list of every firm that there was a Middlebury alumni at that I was interested in. I skipped all the big ones because I knew going in. No Big Firm is going to hire a sophomore candidate, right? So going to all the small firms. Any person I can find and then asking my dad for introductions that he has going back to my high school friends,
Patrick (CEO of WSO): [00:13:27] This is venture funds. This is private equity. This is,
Alex: [00:13:30] Yeah, private equity wealth managers like
Patrick (CEO of WSO): [00:13:34] Anything finance related because this is a sophomore internship.
Alex: [00:13:37] Exactly. Any- anything I can do to get my foot in the door, you know? And you know, I'm very lucky that the fund did great after. It looks even better now. But at the time, yeah, it was a, you know, a five-man job, an unpaid internship. It wasn't. It wasn't a big, sexy thing, but it got my foot in the door and got me experience and that was all I was.
Patrick (CEO of WSO): [00:13:55] Cool. Ok, so you have that experience over the summer. You're kind of coming back now. You have something good on the resume, right? Yep. This is now your junior summer or sorry, junior year.
Alex: [00:14:07] So yeah, it's a good note to make here, too. So it's a junior year with an asterisk to back to that part where I said I was part of a class of 100 people. I took six months off for coming to Middlebury as a part of a structured program they have. And I had the credits from high school where I could have graduated early. So I got to pick my junior year. And so I basically said in this summer, I'm going to graduate. Even though I took time off, I'm going to graduate early and be quote unquote on time or whatever to, you know, be in that class of people. And I recruited for investment banking and went through the fund through the full process to internships.
Patrick (CEO of WSO): [00:14:40] But you had enough credits from high school with like AP classes and all that stuff where you knew you didn't need to take as many credits at Middlebury to graduate.
Alex: [00:14:49] That's where I could have graduated a full semester and a better
Patrick (CEO of WSO): [00:14:54] Three and a half, three and a half years or so. Exactly. Exactly three and a half with a light semester or something like that.
Alex: [00:15:00] Yes, a Middlebury has a four one four, and I think I had four and four being four classes, one class four classes. How they structure. I think I had five or six credits, so I could have sort of just skipped the whole last semester in a bit.
Speaker121: [00:15:13] So what was your thought process? Would you were you leaving it as like an insurance policy in case you didn't get it? Exactly.
Alex: [00:15:20] That was it. It was I'm going to try to go, go about it and do this. And you know, at
Patrick (CEO of WSO): [00:15:24] That point what you decided because I had to go to internship, I'm going to go for it now. I'm going to recruit down for message. Is that the?
Alex: [00:15:30] Yeah, no, I had the grades. I had two good internships, right? I mean, Clinton was not a toxic asset yet. Yeah. And so I had, you know, two great things to speak to. I looked like a junior. On paper, the only thing missing was one semester of grades and I had I had the APS right behind me and say, Look, you want me to graduate on this date? congratulate on that date. So, you know, got to go be a part of that recruiting class.
Patrick (CEO of WSO): [00:15:58] Ok, cool. So and then what would have happened if like, let's say, it didn't work out and you didn't get an internship? Would you have been able to push back then and go?
Alex: [00:16:06] So that's sort of what happened? Ok, so let's
Patrick (CEO of WSO): [00:16:09] Talk about to your we'll call it your junior year,
Alex: [00:16:13] Right
Patrick (CEO of WSO): [00:16:14] To it back with that class. And then so you're doing resume drops there coming in? Yeah. How many resume drops 30, 20, 50. What?
Alex: [00:16:24] Well, north of 50 little, I think a little bit under a hundred in terms of,21
Patrick (CEO of WSO): [00:16:28] Yeah, people coming on campus to Middlebury and well,
Alex: [00:16:31] Combination of on-campus and listing school. Oh, and listings online. Right, right. Right. I would say on campus there were probably closer to. There are probably two dozen fish that came on campus, of which I probably got half right, maybe say, a dozen a dozen things that I talked to people before the first round. Yeah, exactly. Ok, so talk to me.
Patrick (CEO of WSO): [00:16:50] Let's talk about on-campus first. So first round, you kind of do well, you know, go. You drop twenty-four resumes your resume rather. Twelve first-round interviews. What does it look like? What does it look like? Are these mostly banks investment banks?
Alex: [00:17:01] These are. I'm purely looking at investment banks.
Patrick (CEO of WSO): [00:17:04] Okay, so all of us banks middle-market gold brackets?
Alex: [00:17:07] Yep. Combination thereof, not all the bulge brackets. It's funny. Middlebury is very sort of funny about who goes there, right? So, you know, Goldman is very heavy. Morgan Stanley, for sure. Deutsche Bank, Bank of America, Barclays. There's not a lot of presence from credit Suisse or from JP, or at least there wasn't when I was doing it, but I know some people there as well. But it was a very sort of different feel about how that was all going to work. And yeah, there are sort of random guys who come on as well. A lot of sort of boutique banks of Middlebury alums end up their income. You know, what's interesting about Middlebury is, I think it's sort of it's only recently come into its prime as like a, you know, more of a course school for these guys. And a lot of it is alumni-driven. So if we end up with a lot of alumni at a bank, they come on campus. And the story that I've heard I haven't validated, but the legend rumor or whatever was that there was someone senior at Lehman Brothers from Middlebury. So Lehman Brothers, I think again, this is someone should validate this, but with sort of the Middlebury Bank and post-2008, everyone sort of scattered and you know, we got to go and have a lot more reach across Wall Street as people sort of went elsewhere. And, you know, it was very, you know, very alumni driven, but who goes where? but yeah, had a bunch of different on-campus interviews, bombed a fair number of them. Right. It's, you know, it's definitely a practice makes perfect sort of thing.
Patrick (CEO of WSO): [00:18:33] And did you not have our Ivy interview course yet, Alex and I just.
Alex: [00:18:37] No, no, I actually did. And it's funny. So there were two things that got me through the process, really? Right. And one of them was absolutely your course. I would. You said, you know, early on, you know, liberal arts school Middlebury, while I was there until the very end, didn't even have an account, of course. And when I wanted to go take one separately, which I ended up doing, I did. I did a summer Harvard accounting course when I was at the venture internship. They were upset about it. They didn't want account for credit. They didn't even want me taking the course like they were very focused on this. As a liberal arts school, you shouldn't be focused on that. So all of my technical came from your guide for the most part, which was an absolute lifesaver. Still very grateful.
Patrick (CEO of WSO): [00:19:19] Even at a liberal arts college, I think nowadays, or even when you were, you were interviewing. They had started grilling the liberal arts kids. They expected you to know it at that point. Whereas, you know, to when I was going through it, It was more of like, OK, do you know it or not? And if you said no, you kind of scoot through and it was more fit overall. But yeah, tell me about that. So they were pretty heavy on the technical for you guys, even with no accounting background.
Alex: [00:19:43] It was, it was very it differed by firm. We definitely didn't get the words to it, right? I have friends who went to other schools where I have heard of some crazy technical questions that I never got right. But we definitely got into accounting and you had to walk through an income statement and walk through what happens in a transaction across, you know, the three statements. The basics, right? You know, I think you're. I have friends who had questions that were far outside the scope of your guide. They went to, you know, more technical programs. I don't think I ever had a question outside the scope of your guide. Right. So it was very much, you know if you knew the Wall Street Oasis guide backwards and forwards, which I basically had memorized it, I read it way too many times. It was my textbook of how to learn the stuff. You were going to be fine with the technical. My other huge thing that I'm forever grateful for. I had a whole crazy housing mix-up on campus where I ended up in an apartment of people that I didn't know at all. So it was just totally. I forget exactly how it happened, but it was driven by one of my friends, surprisingly transferred. I had gotten messed up out of my house and he gave me his housing and I fell into this thing. And two of the girls in my apartment were really hard-core investment bankers. And so one of them went to UBS and is now at a D capital. And the other one is a hotshot at Apollo. And between the two of them, the practice interviews that they, you know, they took the time to give me. They were a year ahead of me and they'd already sort of seen it. They had their offers lined up. They really carried me through the process and taught me and I would be. I would not have made it if they hadn't sat with me for hours and practiced. So I was very, very lucky that I fell into that speed and met them.
Patrick (CEO of WSO): [00:21:27] Yeah, the mock interviews are a big, big thing that a lot of people underestimate. They think they can go in and wing it, especially if they feel confident about their speaking ability. Then they get in there and it's like, oh, that could have been a little bit smoother. And that's just enough to get the ding.
Alex: [00:21:41] And so I was really not smooth. And actually, there's a separate side story here as well where I apologize. It's a tangent, but I still think it's so funny. So. I was really dead set on Goldman Sachs, like I mentioned, and in this
Patrick (CEO of WSO): [00:22:00] The way is not a good strategy for those listening. Oh yeah,
Alex: [00:22:03] No, it's absolutely not. And that look, I hedged my bet. But I was. I was. I really wanted that and I got rejected in that after that first round that first time around. And it was the same night that one of the people in my apartment had broken up with their person. They were dating and the two of us had this ridiculous night. We finished off a bottle of vodka. And at like two in the morning, she calls up her friend Barclays and gets me an interview for like the next day. Oh no.
Patrick (CEO of WSO): [00:22:36] The next day. And.
Alex: [00:22:41] Look, I could blame the hangover. I'm not going to blame The Hangover. I was not a good interviewer at that point, and the feedback was basically like, you're a terrible interviewer and the luckily, the guy MBA at Berkeley is like me enough to sort of say, Look, you know, you're an interview again gave you a second chance. Go and talk to this guy, this analyst a few times and have him coach you and teach you how to do it. And so got even more help along the way. Pure luck off of this random night out of I get introduced to this guy who further sort of coached me on, you know, think about your points that have a B and C. Make sure every answer has a logical flow because I was and I'm doing it right now, I can sort of be all over the place if I don't.
Patrick (CEO of WSO): [00:23:25] You like the tangents? It's all good.
Alex: [00:23:27] Yeah, yeah,
Patrick (CEO of WSO): [00:23:28] I like it. I think it's more interesting anyways. So, OK, so you do. You do finally? Kind of. So this is again your junior summer or yeah, you're applying for it here early in junior year. You so happens. So what happens? Yeah. So I end up with.
Alex: [00:23:45] With so I had with three different offers, I'm friends, I want to tell the story best. And so one of the offers I got when it ended up taking, I had interviewed at Wells Fargo and Wells Fargo, had a quote from Middlebury or from Middlebury for their whole listing school category. We weren't the court school for them. And so basically, I think no one from Middlebury that year, but one of the guys that I had liked me and I was in a computer science class with a guy a couple of years older than me who was who had gone there, and the two of them sort of referred me to you still secured, which they owned at the time. And they knew that I came from a real estate background and I talked about it through my dad. I introduced still security in Wells Fargo and then put together, oh, wait, you're from London, you can work in London, you have work authorization. Our London office needs somebody. And I got stuck into the process in London through this sort of random connection at Wells Fargo, having failed out of the normal interview process. So I had that and a couple of other offers, and I won't I won't shame the bank. But one of the other offers, the MD who called me with the offer, literally said, Can I use language here and quote, or should I literally called me and said, You were fucking terrible? Luckily for you, you were the least fucking terrible. And so I wasn't super excited about that offer in the way that it came and share the bank. I will I won't shame the bank on that one. But they had a reputation for being like that at the time, and I would say that it's true based on my brief experience. Yeah. So had had a big bank offer that came with sort of a jerky form, a sort of, you know, not as prestigious offer. And then he still secured. He still secured at the time was the number one ranked real estate investment bank in the world by a good margin. And even better, they were very small team having that ranking. The guys were super friendly. I wanted to be in London. It was sort of like the dream offer, like it sort of worked out perfectly. If it wasn't going to be Goldman, I'm glad it was them. Now this is summer 2016. So there's a lot going on and it's firstly an incredible internship experience. I'm a very strong modeller. It's entirely because of and I'll think I'll thank him by name here because I'm again, I'm incredibly grateful. There's a guy, there's an analyst. I worked with tom Anderson, who spent way more time than I deserved with me on a really ridiculous deal that it's a whole other story we don't run out of time. Basically, he's still got staff on a mega deal, and I got roped in as an intern and it was there were some crazy intern stories that came through this mega-deal, some of which are on Wall Street Oasis and really just got the full banking experience right 100 hour, weeks and multiple all-nighters in a week. We had a dedicated fridge full of Red Bull for the analysts and the interns. I mean, it was full force, right? We it was heavy drinking, you know, work hard, play hard. It was everything that banking was advertised to be other than it was terrible money. I think it worked out to like five dollars an hour. They were, you know, the UK market is below the U.S. market is still below the UK market. And it was like, Yeah, what did I hear anything? But again, I learned a tremendous amount and I was really excited to go and hopefully go back. And then June 2016, Brexit. So my first ever pay check comes the morning that the pound drops like 30 percent after the election, after the election results and the whole summer after that become the last half of the summer. It's all sort of panic mode of what's going to go on, and the summer sort of comes out and offers don't get made to any of the class and sort of like, ok, stay tuned. We don't know what's going on. Are we hiring or firing Brexit? So Brexit happens. No offers get made. We have to sort of figure it out. They sort of tell us to stay on hold. They had sort of told me, you know, expect to hear back something around January or February or early winter. But Middlebury had to know if I was going to graduate early or not by September. And so I had to give them an answer way before I was going to know. And I was not willing to go gamble right. And so I told, I told he still, you know, forget about it and went back and re recruit it again. So I had a second junior year of summer recruiting process.
Patrick (CEO of WSO): [00:28:13] But now you're all polished.
Alex: [00:28:14] Now I'm polished and now I've got a big transaction. You know, I couldn't talk about it in the recruiting process hadn't closed yet, but I got to put, you know, a well north of 10 billion transaction on my resume. And I came from a fancy bank and all was always going to be good. And I loved real estate banking. That's what I wanted to do. And I went down the whole process and went through it all over again, came out with again three offers and it was actually funny. They all came within ten minutes of each other. And I remember I remember literally getting one, putting them on hold, getting the second, putting them on hold, getting the third right. I had three phone call. It was like simultaneous.
Patrick (CEO of WSO): [00:28:54] Well, probably because they all knew they were all jumping. It was earlier. You're I'll call it your junior senior year. Was it early or junior senior year that you got that where it was like. It was October.
Alex: [00:29:07] Yeah, late October. I think it was something like that.
Patrick (CEO of WSO): [00:29:09] Had they all kind of become on campus at the same time and like, we're just trying to like super days, we're close. So how did that work? How would they all close?
Alex: [00:29:16] So it was so basically all the interviews were really close together as well. So actually what it was this crazy again brief side tangent story I had. So I had interviewed at William Blair and Macquarie back to back where it was Chicago, New York, and I had I remember I had to take the Macquarie IQ test in my hotel room and it's like 1:00 in the morning with William Blair and then doing the William Blair thing, coming back to New York and doing a Jeffries interview. Um, and then
Patrick (CEO of WSO): [00:30:00] Actually just in the middle of a school week, a normal school,
Alex: [00:30:02] This is the middle of a normal school week and I'm coming back and all night or in school or when I get back and had amazing classmates who helped begin this whole story is I had the support of so many people helped me out. But actually, on the timing, as we're thinking about this, this actually happened in mid-October that I'm having these interviews. Yeah. And I then get a call from the Clinton campaign and this is October of 2016. And so I end up taking two weeks off of school to go and work for them again in central Pennsylvania. And I come out of that. Immediately after election night, the morning after election like election night, I drove out of Pennsylvania and I drove to New York for my Goldman interview.
Patrick (CEO of WSO): [00:30:45] Oh my gosh, crazy.
Alex: [00:30:47] And I think I got the offer from all three the following day. So Jefferies and Macquarie had waited a little bit and Goldman moved quickly, and it just coincidentally happened like quite literally on the same phone call. It was really something else.
Patrick (CEO of WSO): [00:31:05] And then I had the results. Do you think it's because they knew the other ones were going, do you think they move fast because they knew the other ones were extending offers like they have intel or something?
Alex: [00:31:14] Maybe I just thought I crushed my Goldman interview, to be honest, and it was, which is actually the next transition of the story of all of these guys. I wanted to be on the real estate investment banking thing, and the Macquarie sort of gave it a name Macquarie really wanted me. I had a fraternity brother who was helping me the whole way through. They were going to, you know, we were talking about doing an infrastructure fund offer. It was really going to be pretty great. Jefferies, you know, sort of said, well, our real estate team is not strong, but health care health care team is and they were really sort of courting me and Goldman didn't really court, right? Goldman. I showed up and I just sort of hit it off with his VP while I was interviewing. He really liked me. I liked him. And Goldman has. Goldman doesn't do group specific offers. They do a placement process. And so, you know, you take your offer and then you can figure out what your group is going to be. And so I ended up with these offers and it was OK. It was really strong. Macquarie Group, really strong. Jefferies Group or roll the dice on Goldman and Goldman had been the goal the whole time. And to your point about bad strategy focusing on Goldman, this was in hindsight, probably a bad decision
Patrick (CEO of WSO): [00:32:22] Of, well, no, what I meant by only. Yeah, yeah,
Alex: [00:32:26] I hear you. But no, no.
Patrick (CEO of WSO): [00:32:28] Now that you have the offer, take it.
Alex: [00:32:30] Well, that was I thought. I have the offer in hand. It's a generalist offer and know where I'm going to be, but I hit it off with this VP and the, you know, sort of derivative structuring group. And you know, I had networked heavily with real estate and leveraged finance, and I really thought I would end up in one of those two groups. And I put both of those groups on my selection list. But when I finally got Thursday, I took the Goldman offer I made. I made the decision to turn down Macquarie and Jefferies and wait out Goldman. And when I finally got placed at Goldman, I didn't get placed in leveraged finance or in real estate. I got placed with the derivatives group, which, you know, I had this great relationship with the VP all as well. And I think all as well. And it's going to be great, you know, not what I was looking for, but it's Goldman and cool group, cool guy. And I mean, I don't want to shit on Goldman here. My summer there was just not what I wanted at all. And it was just not going to work. And I sort of halfway through the summer, I'd already seen investment banker. I knew what it was like to work hard. I knew what a hundred-hour week was. It wasn't about that, but it was the. Just sort of the group dynamic and where I was and how the group functioned and what we were doing and just the whole thing, I sort of said I can't do this for two years. I need to go, try to lateral and do something else.
Patrick (CEO of WSO): [00:33:43] And by the way, for the record, when I say bad strategists, go for Goldman or be so focused on one bank, it's more around the specific odds. It's not like you were just applying to Goldman in the bulge brackets dressed. Everybody listen. He said he had interviews with Harris Williams and with other middle market banks. That's what I said. It was like you get this bulge bracket or bust mentality on Wall Street and it's really toxic and it's really actually not healthy. And there's some amazing elite boutique banks, middle-market banks that are pay just as well, if some of them even better. That's absolutely right. Yeah.
Alex: [00:34:15] So at the time, William Blair was, I think, the highest name bank on Wall Street. I actually really wanted that one, and I don't know exactly why I didn't get it, but I have a feeling why I didn't get it. And it was a literally a high school bullshit thing from way back when it's my. My suspicion as I bumped into someone who we never got along. And I think that's what did it. So.
Patrick (CEO of WSO): [00:34:36] So you're so, but you're at Goldman. You're happy to have somebody like this is not the group I want to be in. It's not.
Alex: [00:34:41] And I asked the transfer right. And apparently I was not the only one. And they were there were it was sort of one of those things of, well, they can't all leave and all transfer. So no. And so I think actually, I think all of my class or at least, you know, the people I was interning with, I think we were all sort of looking at it elsewhere. It wasn't that good of an experience. To be perfectly honest and nothing against Goldman or even that group, it was just. The vibes weren't there, we'll say.
Patrick (CEO of WSO): [00:35:10] Was it just because there wasn't enough volume, was it all pitching?
Alex: [00:35:14] No, no. There's a lot of deal volume. It was again, I just I really don't want to speak too negatively of anyone.
Patrick (CEO of WSO): [00:35:21] It was just a certain leadership. There wasn't it wasn't exactly teaching you or wasn't. It wasn't a
Alex: [00:35:26] It wasn't going to be. It wasn't going to be the right fit where I could spend two years and feel like I was, you know, alive and accomplishing things. And, you know, the group. Yeah, it wasn't. It wasn't the right thing. And so that's a pretty, pretty
Patrick (CEO of WSO): [00:35:41] Ballsy move in the middle of your internship to ask for a transfer.
Alex: [00:35:44] Well, I tried to do it softly, right, and it was brought up of like, you know, you should figure it out in Goldman. Goldman actually really encourages that, which I think is actually a great thing because they really try to have people network across the firm and figure out where they fit. And I actually know a number of people I interned with who moved groups, right? It's a very doable thing. And I went to a school alumni there who I had a relationship with and trusted and talked to him about it. And you know, I was really trying to figure it out the smart way. It was probably a little bit ballsy. The balls of your part really was making the decision of, I don't want to go back here and, you know, taking the time to go, look at it elsewhere instead of focusing on the internship, there was not time to do both. And I kind of made that decision of, I need to figure out something else. This is not going to be it. And so how did you approach
Patrick (CEO of WSO): [00:36:32] The end of that internship, the second half?
Alex: [00:36:35] So I wanted to leave office thoughtfully as possible. I wasn't I wasn't trying to be a bottom bucket person, right? But I also made sure that I, you know, was hedging my bets. And if it meant leaving a little bit earlier at night or saving some time at the end to go in-network or go and eat, fly to things and go and interview and you know, I was trying to go and it was probably apparent, to be honest, but I was trying to do my best to go and mask it. I'm not going to stick it out here for two years. Yeah.
Patrick (CEO of WSO): [00:37:05] And it was confusing, a turn offer came correct. Yeah, yeah, yeah. I would imagine now you're going into your senior year with the unenviable position of having no return offer.
Alex: [00:37:17] That's exactly right. And it was really, really stressful. I thought I was hot shit, right? I thought, Well, you're coming
Patrick (CEO of WSO): [00:37:26] Out, but still you still you
Alex: [00:37:28] Still Goldman. Yeah, yeah. You still Goldman. I already, you know, you still had its own weird thing. Do it explainable but weird, Goldman, you know, not come in with an offer. Coming out with an offer is not the right look and having two junior year internships. And at that point, the Clinton thing is toxic is not Trump is in office. So that has come off the risk that has to come off the resume, but it's way to see
Patrick (CEO of WSO): [00:37:50] Why. So Goldman, like you knew you did you know you weren't going to get an offer because like things were going poorly in the first half? Or did you feel like, like, did they tell you halfway through? And I had
Alex: [00:38:02] A conversation with my MD basically sort of said, we've noticed that things have been slipping, you know, are you trying to get an offer here and make this happen or not? And I didn't give him a straight answer, but I gave him an answer that sort of said, we're not. And you know, I had the intervention conversation part way.
Patrick (CEO of WSO): [00:38:23] Why would you do that? It was really because the reason yeah, I realize it's like you'd worked so hard to get up to that point,
Alex: [00:38:32] It was a really emotional process to go through because you're exactly right. I know not just for another
Patrick (CEO of WSO): [00:38:38] Six weeks suffer. And get them the offer
Alex: [00:38:43] With the smog problem. I probably should have, but in my view, all the recruiting was happening right then and there and it was a get-it-now before it's all gone. Because if you wait till the end, there's going to be nothing left.
Patrick (CEO of WSO): [00:38:56] Got it. So. Oh, I got it. So your whole thing was like, if I don't lateral in this late summer, if I just ahead and take it and smile and take it, I get an offer. I'm going to want to miss all of the few lateral seats that are actually.
Alex: [00:39:11] Exactly, exactly.
Patrick (CEO of WSO): [00:39:12] So you had to kind of you're kind of hedging, trying to trying to get the offer still sort of, but still sort of. But like not super. And it was a very because the offer the value of the offer is not the actual offer value. The offer is just the signal it sends to other potential employers.
Alex: [00:39:28] Right, that's exactly it. But to your point, I had to go ahead. Right. It was a yeah, if I miss, if I missed the boat because everyone's already filled their lateral seats, then I'm going to end up with this offer and then probably not taking it. And then where am I? Are the listeners
Patrick (CEO of WSO): [00:39:43] That aren't aware of that. Talk about that process and like, were you able to get into any lateral interviews? Because so for people that don't know lateral interviews, like for four seats that aren't filled from other internship classes, know lateral just means from bank to bank. So it's like you want to switch for whatever reason. So, you know, Alex here was at Goldman. Theoretically, you probably got some looks.
Alex: [00:40:05] I'm thinking, Yeah, no, I had. I had a number of them, and it's really, really hard to make it work. But I made I made, you know, I probably got into, you know, three to six processes, something like that three, four, five, I don't know exactly how many. None of them got all that far because that's the thing is, it's your you're coming off and you're exhausted. You're being, you know, I mean, I particularly had a very, very grindy summer at Goldman, and I was just worn down. I wasn't coming off. Well, you know, it's we're seeing here. It's a hard thing to sort of explain to people like, yeah, like, I wanted this and now I don't want it and talking to you, but also I'm not sure, you know? Yeah, they're like, Why
Patrick (CEO of WSO): [00:40:46] Are you going to get your offer at Goldman?
Alex: [00:40:48] Right, right. So it was it was. I did it poorly is the honest answer. I really sort of flubbed that process.
Patrick (CEO of WSO): [00:40:56] It sounds like it was a meat grinder and you having done. The previous meat grinder of the week, the summer before you had at that point ready to be working, it was kind of like this weird in between. You got caught in between of like not quite going fully full bore.
Alex: [00:41:14] So I differentiated actually. I think people and a lot of people say like, Oh, banking is a meat grinder and it stays like banking. You know, people say thank you to the meat grinder. There are a lot of different kinds of meat grinder, right? There are a lot of different ways to work one hundred hours and a lot different ways to take your life. And you know, I think Goldman was really actually fewer hours than you, though the problem was it was more intensive hours and it was much more stressful hours. You know, my friend, you know, you hear about people who work two-hour weeks and say, Oh yeah, we're waiting for. We didn't do a turn of Dec and you go to the gym and you toss a ball around, you're throwing stuff at the desk and you're hanging out. You still we do a hundred-hour weeks, but you know, we'd order benihana for dinner and you get 45 minutes to hang out at the bar. You know, it was just different. And Goldman, it was. It was just nonstop at my desk. And there was absolutely no room coming up for air. And that just made it much harder.
Patrick (CEO of WSO): [00:42:09] Yeah. So do you feel like? That's a really good lesson, I mean, for people listening in terms of like knowing the specific risks of when you don't know what group you're going to. You don't know who you're really working for and what the top levels is going to be like in what group you're going to be slotted into. It's kind of like that can totally change your summer and change whether you can actually make it, make it through with an offer. Yeah. And the return operates, they're not even in the 80s or 90s percent. So they're about 60. Yeah, 60 days.
Alex: [00:42:45] And that was a part of my life, too, was I. So I had heard, and the previous summer, Macquarie had only made 10 percent return offers. All right. And
Patrick (CEO of WSO): [00:42:57] I'm running away
Alex: [00:42:57] From where I'm like, Yeah, like Macquarie. Like, I don't know if I'm actually that's going to turn out, you know, Jefferies, you know, was its own thing. And again, I don't want to be too negative, but that's the guy that's sweaty, too sweaty, too. And the guy is I actually would have worked for there, I think actually got some very public trouble. So that was probably a bullet dodged. Yeah. So really, in hindsight, like it was, you know, Macquarie ended up making all the offers that year went from 10 percent to 90 plus percent. You know, of course I missed it. But with the knowledge that I had, I probably don't know if I made the right decision. Still, it's something that I still sometimes think of that.
Patrick (CEO of WSO): [00:43:33] Well, I mean, I think people who are looking for a return offer data that you're in a company database that we do have percentages for. So people are trying to look for that data. But like you said, it's not always, you know, past performance
Alex: [00:43:49] Rates, it can vary significantly.
Patrick (CEO of WSO): [00:43:51] Let's put it this way if you have two middle-market banks that are equal weighting or similar weighting or like, let's say, one slightly, but they have like a 90 percent offer rate and the other one has a 50 percent off rate. I would almost always tell you to go with the ninety like historically like just go with that because it's safer. But anyway, so OK, so you're pretty. It sounds like a brutal summer. I was.
Alex: [00:44:11] It was real hard.
Patrick (CEO of WSO): [00:44:12] Yeah, yeah. And so you're kind of coming in. You don't get the offer. Was it kind of like you already knew you didn't have it kind of going to that? Yeah, I it was.
Alex: [00:44:19] It was, you know, it's never fun to hear it, but it wasn't unexpected either. Yeah. So you know that look, it was a hard time, right? I had a really hard fall that that fall at school. It was also again having graduated on time. It's now my super senior year. So almost all my friends are gone. So I'm sort of like, I felt like one friend left on campus. Yeah, and I'm in this super sort of dark place. If I'm basically by myself and don't have my job lined up, I haven't figured this out. You know, I have more. I've missed the bulk of the lateral recruiting process and it was
Patrick (CEO of WSO): [00:44:52] You're back to the drawing board. The kid who knew everything was lined up his freshman year, which I would always say. Usually if you know that early, you're going to be fine, right? It's very rare to be kind of throwing a curve. It sounds like you almost like peaked early, like in your college career, then like somehow stumbled at the last time. Like, you're like the finish line and you're like, wow, I really it really
Alex: [00:45:16] Just sort of fell apart there at the end.
Patrick (CEO of WSO): [00:45:18] Now, tell me, has a twenty-two-year-old, maybe even twenty-three at this point, you're like, you said you're super confident, which is very normal for a guy. You know, a guy who's done all those things. These are coming in senior year and saying, you know, I should be at X Y Z Band. Great. Yeah, the reality is those seats are filled.
Alex: [00:45:34] Yep, that's right.
Patrick (CEO of WSO): [00:45:35] So tell me how you kind of went about when did you kind of have the realization that you know, Hey, this may not be, oh,
Alex: [00:45:42] I knew before I got back to campus that basically all the lateral seats were filled, right? Because I'd been I've been talking to them, right? And I knew I had missed this boat, missed that boat, missed that boat. I had all the deadlines. I talked to all the people they said were going to know, you know, by X, Y and Z. I had an excel sheet of everyone's timelines. And, you know, basically by September one, it was just right. Yeah. And so I got back to school and I had a real thing, right? Because I thought I got to thinking, why did I want to be an investment banking in the first place? Right? And the answer when I was a little kid was, I don't know what I want to do, and I know I'm good with numbers and I want to make a lot of money. And, you know, I've sort of seen it and I'm going to do it and I'll figure it out later. Right. And the sophomore summer thing was really influential because I really saw what I saw it sort of it's almost like Shangri-La, right of like, you see these really smart guys doing really cool deals they don't make, you know, you're not making, you know, mega fun private equity money, but you're making really good money and you're having fun the whole time. Yeah. And I had that in my mind. Okay. I want to do banking to get into better capital, right? And that the seed was planted that sophomore year. And so as I'm going into senior year and I'm like, all the lateral seats are gone, you know, venture capital is what I came in this way. How do I make that happen? And I start doing a ton of networking with VC firms. Really, really difficult to do. Got very little response rate. Yeah, they're like,
Patrick (CEO of WSO): [00:47:07] What do you mean? You have banking all plastered all over your eyes? Ok, yeah, sure. That's one internships right here, right? With at that
Alex: [00:47:14] Time it was growing job, but it wasn't even bigger now, it would mean a lot more of it. It meant not as much. Yeah, luckily, the private equity firm still had stuff going on. There were a number of private tech firms looking for full-time analysts. So I got into a bunch of private equity processes thinking, OK, I can go make this work. And at the same time, I'm like saying, OK, how are we going to do it? How do we get into venture? Well, venture-backed start-ups are one of the best ways to go do that right? And I knew I knew that I liked being an operator. I knew that I had the financial knowledge and I sort of said, OK, maybe a fintech start-up is another alternative option. Yeah. And went through the process for the fintechs with the process of private equity firms and came out, in the end, a really, really one of those simultaneous moments of like two offers at the same time with like truly picked your path of a real but not super well-known fund. But it was out in Connecticut, right? It would have been either living in the suburbs or a reverse commute. And it was in a group in the funds that I didn't really want to be in. And it was,
Patrick (CEO of WSO): [00:48:19] You know, me about that. What do you mean, like a private equity fund?
Alex: [00:48:21] Yeah. Private equity fund doing secondary transactions before those were sexy. Yeah, OK. And I was in their secondary transactions group. And to be honest with you again, not cheating on the fund. I didn't like the guys and that's what it really came down to was. I mean, all these interviews and like all these guys kind of feel like bricks and I'm dealing of the start-ups. They're all like coolest people. And the guy I was actually a workforce. I was talking to the start-up where this is oak north on my resumé. So fastest ever fintech unicorn fest. Every unicorn in Europe. It's the fastest ever. It's got to be a billion valuation them like nine months to a billion-dollar valuation. Wow. Right. They had, you know, a few hundred million dollars in capital raised like really sort of there in that growth phase, but they want to go and open up a U.S. office and they want and they've brought in this guy x Deutsche Bank X, Palantir, like x Israeli Special Forces. It's just really all over the place, but really cool. Awesome guy who I love right now. I'm like, OK, like, you know, you talk to your mentors and your parents pick the person you want to work for. And I even sort of learn that previously. Yeah, and I was thinking, OK, you know what? I can earn a little bit more money in this private equity firm. Then I'm living in the suburbs. I'm reverse commuting or I can go be the first analyst, second person, and the super well funded, super-fast growing start-up with like a really cool guy to go work for and be on the ground in New York. And so that was the decision. Yeah, and I hope I don't know how much time you have.
Patrick (CEO of WSO): [00:49:54] Oh, go ahead. I want to hear it. Let's talk about North and I want to get to what you're doing now.
Alex: [00:49:58] Yeah. So, OK, north was all over the place. So we built out a team in New York,
Patrick (CEO of WSO): [00:50:04] I can't imagine. Yeah, you're the number one. You're the number one employee from that office. Ok, so
Alex: [00:50:08] Yeah, yeah, I'm the number two employee number one, junior employer. They hired a guy to run the office and I was, you know, the first person. Yeah, a lot of
Patrick (CEO of WSO): [00:50:17] First tell me what they do, what it's
Alex: [00:50:18] Yeah. So Oak North is a fintech, they've got an artificial intelligence underwriting platform. They license out the big banks. And so and so they basically wanted someone with a, you know, sort of predatory financing group, you know, leveraged finance type background, which I had. And they were actively recruiting investment banking interns and people like me. I was literally their profile, right? And they told me straight up, like, we want people who have been in the investment banks and decided they wanted to work for a start-up, and they have some basic technical skills. They know what they're doing, but they want to go work for a start-up. And they recruited, reached out to me, actually, and got in the process there. And it was all just sort of seemed perfect. It was a very sort of honeymoon period coming in.
Patrick (CEO of WSO): [00:51:00] Talk to me about pay was for super low because of it being a start-up
Alex: [00:51:05] Base with super low.
Patrick (CEO of WSO): [00:51:06] Not because it was like 50 low.
Alex: [00:51:09] Not like 50 low. No, no. But put it this way had I had three roommates living in a, you know, pretty shitty apartment. But I say shitty, very cheap with certain things that were not great, but enough upside where I wanted to live there. And you know, it was really, really tight. You know, it was. It was it was hard. You know, you make it work in New York, but not you're not rolling in it. Yeah. And the way that we had negotiated it was they got me down on my base for a guaranteed bonus that would sort of top me up to be about market.
Patrick (CEO of WSO): [00:51:48] What is that market to what?
Alex: [00:51:50] So if I was if I'd gone to go work at it, sort of a middle-market investment bank, my all end up the same if I lasted a year with the idea.
Patrick (CEO of WSO): [00:51:58] So I sold one hundred and twenty-two.
Alex: [00:52:00] Yeah, exactly. About one hundred. About a hundred and twenty. Ok, so if I lasted it out, I had the guaranteed bonus for.
Patrick (CEO of WSO): [00:52:08] Ok, and so did that happen?
Alex: [00:52:09] It did, kind of. Almost not, and that's and that's why I think this is. More interesting parts of the whole, not it's that it's not a boring adventure, but it's one of the more interesting parts of the adventure.
Patrick (CEO of WSO): [00:52:19] I mean, yeah, no.
Alex: [00:52:20] So go to North work, come to go work for this guy. Um. We hire another person who is going to be another person in the office. Right now, there are sort of two mid-level people. Yeah, and me, he gets fired. He has there's north was a very political, very game of thrones. Everyone's got sharp elbows. It was, you know, investment banking on steroids in terms of the environment that sticking around there. And he and he had just got in. He got him beat right, and they were jerking him around and they give him a very hard time and it was really one of those, I quit your fired moments for him. Yeah.
Patrick (CEO of WSO): [00:53:06] This is the guy you were coming into
Alex: [00:53:08] This guy that I came in to work for.
Patrick (CEO of WSO): [00:53:09] Yeah, OK. And so I lost him, which was a huge
Alex: [00:53:13] Which was a huge blow. And I'm thinking, OK, do I even want to be here anymore? I've only been here for a handful of months, some fresh out of school like, I know it's bad luck to hop again, but I should probably start looking around. But in the meantime, I'm working with this other senior person who I really like her as well. You know, frankly, her skill sets less a fit for the job and she has, you know, it's a good thing and a bad thing because I'm getting sort of carry a lot more of the weight I'm actually speaking and pitches you need to talk to. You know, these really, you know, senior executives at 23 years old and being really the face of this thing, whereas I wasn't as much before because, you know, she sort of needed a little bit of help to go carry stuff. And I'm sort of looking around, but it's a not bad life, right? I'm not getting paid as much, but my hours are way better. Right. It's not nine to five, but I'm not an all-nighter and only a handful of times, and it's because of other people dropping balls. Yeah. You know, It was not a terrible thing, and it was mostly just saying, I can stick this out for a couple of years and figure out business, school or venture. You know, this is a good look, right? I was sort of content to stick it out there. And so it's me and her working together. We're looking at hiring people and we're trying to grow. We can't get a hold on the business. There are issues with our execution. There are issues of corporate strategy, there are issues with the product. It's, you know, there are all sorts of issues that we're having and it's just we're not having success. And one of the parts that actually made it difficult as well was in Europe. The CEO of Oak North is a bit of a celebrity. And so he can get any meeting because he's had and anyone will meet with them because like they know who he is, right? And it does not translate to the U.S. and that was not understood. It's like, Well, why can't you get a meeting? We have? We doesn't mean anything here. Yeah, we're just two guys, a girl and a guy, it's like we're figuring it out. But it was a stressful look for the office and what ended up happening. And one of the crazy stories. So we have this. We got a bit. We got a meeting with RBC and there Toronto office and It's through one of the founders and he's worked at McKinsey and someone that was at McKinsey. And we have this whole sort of, you know, it's all sort of set up and we spend. This is like a big meeting. This is like every senior stakeholder, 30, some people from their side. It's a full bank meeting. We spent like a month prepping him for it, like all sort of going well, and the CEO at one point sort of loses confidence. You know, you guys don't just think I'm going to come in and come, take it with you. And we're all going to do it together and I'll see how you guys operate. And at this point, my boss sort of says, Look, I know you're talking to meetings, but CEOs there, you're not supposed to be doing that. Like, Sit there, take notes, carry the pitch books like all-employee meetings, a disaster, a total disaster. Ceo carries the whole thing. My boss didn't execute. I sat there quietly, having been told sit there quietly. In the middle of the meeting, my flight gets canceled. And I am texting the CEO of secretary and the CEO flies private. You know, me and my boss are flying, you know, flying coach. And he says, Oh, well, no problem. I'll put you on the jet. And so we come out of this meeting, it's terrible meeting my boss is not get put on the jet hurts like it's cancelled on the way to the airport, but we're in the Navy, right? And CEOs upfront and boss and I are in the backseat and he's yelling at us, you guys were terrible. You guys were awful, just totally for like forty-five-minute ride of pain. My boss is texting me. Doesn't mean you. He means me. Whatever we get to the airport, I get on the plane. I spend two hours in the air on a very small private jet, face to face with the CEO basically being grilled about how I'm garbage and being told on a post box, What do you do? I don't get hit at any value you. When I was 23, I started my own venture fund. What have you done, really? Just a very a really, really miserable, private jet ride.
Patrick (CEO of WSO): [00:57:20] Yeah. Yeah. Ok. So I get the picture. So like, yeah, it was that like the signal that you needed to get out.
Alex: [00:57:29] Well, it was ish. And so I was actively looking already and I came back and I was like, OK, I'm taking my boss texted me, I have the same thought, like, we're both taking the next day off. Neither of us are working like we're having. We took a mental health day. Yeah, on a Thursday right and Friday morning, I get a text from my boss at seven, forty-five in the morning. They just fired me. I argued for your job. I don't know what's going to happen. You know, let me know what I can do to help. Very, very nice text. So she's yeah. So she's she gets fired. I get a call 50 minutes later. If you want a job, move to London by Monday. And so I moved to London over the weekend. Wow, OK. And I moved to London,
Patrick (CEO of WSO): [00:58:21] You know, over the weekend, but I can see from your LinkedIn, you were only there for five months. That's right. So tell me what happened. How did you know just to speed up the process that you ended up there for other two-plus years after that? Yeah.
Alex: [00:58:34] Yeah, no. I know. I know It's really an adventure, and I'm sorry we're taking so much time. I'll try to. I'll try to accelerate it. So there was a guy there who was hired the same day as me. Same role as me. The same everything is me. Really slick guy. Not that I'm not somewhat polished. This guy's really, really polished, right? And he's just sort of a navigator, a manipulator person. And he saw me as a threat to him because we were in our own territories before, and now we're not. This is in London, lives in London, Thailand, London. On Monday, I put this guy, you know, and he's in all the deals I'm in. None of the deals I'm trying to be friendly. Like, How can I help? And I basically get stuck by the printer like, screw you do nothing, right? I'm trying to get involved in stuff. He's taking me off email chains. He's changing meeting rooms. He is like intentionally keeping me out of stuff just like, screw me. At one point, I'm just having tea with my boss, my new boss. And he saw me outside the conference room and ran his meeting two hours over so I couldn't meet with my boss. It was. It was just really out of hand, and on the Thursday I get, he throws me this PowerPoint that needs to go out to a client in like four hours and it's like a hundred slides long and it's absolute garbage. It needs to be completely redone. Yeah. And it's like, OK, well, it's your responsibility. And of course, I failed at it because it needed at least a full day of work. And I'm racing all morning and whatever gets turned in, I get brought upstairs to the conference room, I get fired and then they and they literally say, like Alex, we're sorry, you know, it's not working out. And I looked I looked the co-founder in the face and I said, This is bullshit. You know, I had positive reviews in the U.S. he moved me 4000 miles four days ago, right? All I've tried to do is be involved. No one's let me be involved. I haven't gotten to meet with my boss yet. And what this is over that PowerPoint that had absolutely no chance of doing correctly, like what's going on here? And the guy says, You know what? You're right. And takes me by the shoulder, walking back downstairs transformed me over to the lending side of the business instead of the set of the tech side of the business assigns me to a new MD. That MD gets in a car accident over the weekend. What do I know? It goes on. It's I think it's a long story, but it continues to twist. I come back, he's not there. I have to make my own way to London. There's a whole bunch of other stuff that happens in London, but the plan is always, we're going to reopen a U.S. office. Alex is gonna be the guy to help reopen the US. So I laughed it out in London. It's a whole big To-Do. There's, you know, good blood, bad blood mixed 15 people or so get fired while I'm there because this fires people all the time left and right, and they just have huge turnover. It's still very stressful. I'm trying to last it out. My girlfriend is furious at me for having done this whole thing in the first place. And they moved back to the U.S. We started up another new office. The first analyst all over again? Yeah. In the interest of time, I'll skip most of the crazy stories here, but we had a little bit more success. We raised money from Softbank. We started up proper debt fund. We're doing lending in the U.s. we built a great team. I love my boss that we hire and all these different people that we've brought in. It's a really great thing. Not a lot of success due to literal like cultural differences. We go to credit committee and guys in the UK say, Well, why don't you have this? Well, it doesn't exist in the US. Why don't you have that? You're going to do that in the U.S. And so we have all these deals that were sourcing and we have a billion-plus dollar pipeline and we're barely getting stuff through because every deal we're having to explain why it's different than I would work in the U.K. and nothing closes. I got frustrated. I thankfully got a few deals on my resume so that you talk about, but not nearly as many as I would have liked.
Patrick (CEO of WSO): [01:02:35] It's time to start looking once you started.
Alex: [01:02:37] Yeah, I was actively looking. I'd been in the process for six months with a dream V.C. and I'm like, so excited for this whole thing to sort of happen in the middle of it. Oak North sends me to India. I spend a month in India building out their back-office from scratch for the U.S.. Yeah, and there's all sorts of adventures for India as well. But I did. I did a month in India, establishing all the U.S. back-office procedures and how all that was going to go work. Yeah, and come back. And I'm still in the recruiting process of the VC and all this is going on. And then it's March 20. Now it's March 2020. Covid hits. Yeah, the VC drops the process. We're not going to hire anybody, OK, nor oak north goes full remote. I go I buy a sports car, I drive out to my family's house in Wyoming, I'm going to go work remote from Wyoming. I don't want to be in New York and my building is full of doctors and diplomats. I don't want to be anywhere near the worst building in New York to be impossible for this situation. I'm out of here. Yeah, we have a meeting with Oak North. We get told there are seven million dollars in cash in the bank. We're not going to fire anybody. You're all safe. Two weeks later, my whole team is fired. Whole office is gone. They have the gall. I'm still I will forever be upset about it. On top of this, twofold of one. They published an article in the paper saying how proud they are. They haven't made any money off after having laid off our whole team. And two, when I first joined up with bonus cycle was basically when you join, it's not. It's not an annualized cycle and there was an accounting issue my first day. So instead of being on the March cycle, I was on the April cycle and so I had been told my bonus expectations for that year and I had earned it. I had multiple all-nighters. We'd closed deals. I went to India for these guys and they came back and said, Well, COVID, we were zero and your bunch and also you're fired.
Patrick (CEO of WSO): [01:04:35] And I think I'm pretty brutal. Place to.
Alex: [01:04:38] It was, yeah, it was honest. There's there is it's a great builder of a person to come through that place. It is a meat grinder of all of the wrong sorts and it helped me out and everything else since.
Patrick (CEO of WSO): [01:04:52] Let's talk about what you're doing now, though. Yeah, yeah. So let's give Lux some time.
Alex: [01:04:56] Yeah, again, apologies for how long this is gone. But yeah, so basically they got fired from Oak north. One of my friends says, Hey, look, I've got this great company, lex. They're hiring like, let's get you in the next day after I get fired on the I'm on the phone with the CEO having an interview. I'm in the process. I take their modelling test and talking to people. It's COVID. The economy is destroyed. I have an I have a verbal offer from Lex. A month later. And so I'm happy right? At this point, I said, OK, cool. Like, I get some time off in my career. I've got this fun little sports car that I bought. You know, they don't need me to start right away. Well, car I had, I had a BMW with the package on it and convertible, and it was the last year with power steering, so it was without power steering. So I hadn't got the proper road feel. And I'm driving around the country and a, you know, very high-powered Bmw sports car.
Patrick (CEO of WSO): [01:05:55] You're still in Wyoming at this point.
Alex: [01:05:56] I'm in Wyoming by myself. I, you know, three months, three months with no human contact having stocked up on food. I have to go and be social. I've got a friend in Montana. I say I'm going to drive up there. It starts what becomes a three 000 mile road trip. And so I drove. I drove the BMW thirty thousand miles all over the country, hit most of the states. I've now been to forty-six states after this road trip end up totaling the car in a surprise snowstorm in January and have the conversation where it's OK, it's time to get started. I've had my fun. I have this thing. Let's go get started. So started almost exactly a year ago, actually. Yeah, a year ago. Tomorrow is my anniversary at LAX. And yeah, again, so I worked for a Series B, same start-up in North Texas at this time as a seed-stage start-up, we've now just this past week raised our Series A, which is super exciting to know more
Patrick (CEO of WSO): [01:06:56] About. What is Lex and what do they do?
Alex: [01:06:58] Yeah. So Lex is a real estate investment bank registered broker-dealer. We basically are trying to go and fill a hole in people's capital structure. It's about how people deal with, you know, who has the equity in the real estate transactions. Right. So we do equity recaps, but the idea of having those recaps be at a premium to the existing market. Right. So the existing recap market, there's usually a discount. So we're saying now you can recap at full market price, right? With permanent capital, right? So you don't have it, you don't have an LP. You need to be cashed out and have many years, right? That's non-voting. So you're not getting married to someone who having to go interview and deal partners, you know, just sort of quiet, easy, full-price capital that you can come in and take out some of your equity with and rework your capital structure
Patrick (CEO of WSO): [01:07:43] For real estate, in particular
Alex: [01:07:45] For real estate in particular. We, well, we'll come back to that in a quick sec, but it's all enabled by we built an ATS from scratch, so we partnered up with Nasdaq for their matching system, and our engineers spent multiple years building out basically a mini stock exchange. You can think of it as where you can actually trade these things. Everything is shipped that goes through the DTCC. It looks, feels and acts like a stock. You can hold it in your brokerage account. It's fully liquid, direct ownership of real estate. That's tax advantage. Just like you owned it directly. Instead of through a rate, you get to go pick a single asset and you're buying in institutional real estate like how a fund would buy, but for $250 of minimum investment with a liquid with a huge liquidity option through our marketplace. So I thought the idea is brilliant. We had a bunch of guys, including one of mine. It was another funny story. I got the offer because I knew Drew or it was Drew social circle. And after getting the offer, everyone realized, Wait a minute, our chairman knows you and I figured out the chairman is a friend of my dad's, and so I was as I'm thinking, as my dad is like, Oh yeah, go work for him and end up actually my analyst now is. And this is a parallel process to me. Started the same day as me as my dad's old boss's son. So it's even more of a perfectly parallel time, just a very sort of incestuous world. I go to Lex, my fourth Lex again key of the fourth day I get transferred. And so we brought in someone from Blackstone who was going to go be our sort of special ops at the firm and do stuff that wasn't real estate. And all of a sudden, I'm not doing real estate. I'm doing, I'm doing special ops, I'm doing jewelry and diamond and an art investment banking. And so I spend six months doing that. That business line, you know, we go back to real estate as the main business is what we're trying to go do. And I've been, yeah, having a great time, a lot of fun, and we're really getting stuff done here now at LAX. So, you know, we have our first we did our we did a beta test IPO, right? As great as I came in back in February of twenty-one. Mm hmm. That was friends and family. Make sure the system works. Yeah, we did our retail test IPO of let's see how we can actually get retail demand going. And, you know, don't push it with institutions, but to see what ordinary people who can buy this stuff because we can sell it, non-accredited investors, anyone can go invest in it. Let's see how that market looks. And now we've we're sort of ramping up into our growth phase with our series. Okay, now we can do bigger deals. We have institutional partners, we can do more and more stuff, and we've got a pipeline of deals coming down to go and launch in twenty-two. So really exciting. You know, I think the takeaway of that, I'm running out of time. One of the things of the start-up in the north, stories and any other story of being transferred in back. You know, I think there you work hard. But one of the biggest things that I started up that's both great and terrible is every day is going to be different and you don't know what the next day is going to bring. And sometimes there are really, really rapid changes in direction that are hard to get used to. And the good news is, having been through a meat grinder like North, everything kind of feels, you know, tame in comparison, and the people here are a lot easier to work with and I'm a much happier person. So it's been a lot of fun. That's awesome. Yeah.
Patrick (CEO of WSO): [01:11:15] Appreciate you sharing your story. Any other final words of wisdom before we call it or any other plug you want to plug it?
Alex: [01:11:22] Yeah, I mean, I would absolutely want to plug leaks as my last going word, and I apologize for very, very overtime interview of, yeah, look, I mean, you know, we raise our series a led by Peak six and CO is following on. We've got an absolute ton of momentum coming into 2022. I came here, you know, aside from the fact that I was in. The connection, you know, I think that this is really the coolest concept going right now in fintech and real estate, right? There's a huge trend in the world of democratization, and I don't think real estate has been properly, properly democratized. I think we have the tools to go do that. And, you know, the fact that we've brought in the right team to go, underwrite and have good deals coming through, I think makes it all the better.
Patrick (CEO of WSO): [01:12:04] It's awesome. Super exciting. Yeah. And check it out at Lex Dash Markets.
Alex: [01:12:09] Awesome, Patrick, thank you so much.
Patrick (CEO of WSO): [01:12:10] Thank you, Alex, appreciate your time. And thanks to you, my listeners at Wall Street Oasis, if you have any suggestions whatsoever, please don't hesitate to send them my way. Patrick at Wall Street Oasis. And till next time.
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