WSO Podcast | E123: Big Law to Investment Banking VP making $400k+... but First Sleeping in His Car

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In this episode, Chicago13 shares his winding path graduating from Berkeley in 2006 and trying to make it big by building apps and living in the start-up ecosystem in Silicon Valley. Listen to why it didn't work out along with some words of warning, what the main turning point was and why he ended up getting his JD and jumping into Big Law...only to leave one year later to join a middle-market investment bank. Learn about the common associate struggles starting out in IB, why he was screamed at during a Holiday Party and how he managed to overcome those obstacles to get promoted to VP.

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WSO Podcast (Episode 123) Transcript:

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 talk 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, Chicago13 shares his winding path, graduating from Berkeley in 2006 and trying to make it big by building apps and living in the startup ecosystem in Silicon Valley. Listen to why it didn't work out, along with some words of warning. What the main turning point was and why he ended up getting his J.D. and jumping into big law, only to leave one year later to join a middle market investment bank. Learn about the common associates struggles starting out in Ibey why he was screamed at during a holiday party and how he managed to overcome those obstacles to get promoted to VP. Enjoy. All right. Chicago 13, thanks so much for joining the Wall Street Voices podcast.

Chicago13: [00:01:12] Hey, thank you, Patrick. Good to join.

Patrick (CEO of WSO): [00:01:14] So it'd be awesome if you could just give the listeners a quick summary of your bio.

Chicago13: [00:01:19] Sure, happy to do that. So I grew up on the West Coast. I went to school at UC Berkeley, spent some time out there in the early 2000s and graduated when the economy was great, chose kind of a complete route, completely different route than what was expected. And I went I went the startup route know, didn't follow my didn't follow my friends at the corporate or go to med school like my parents wanted me to. So I did that for a little bit work for a lot of various startups. It was a pretty exciting time to be in the Bay Area. It was when the App Store was just taken off, so people were creating all these kind of dorky little apps. I try to do the same. Their apps like Message in a Bottle and other ones were, you know, it would give you times when the surf would come in, when the very uncool like the low tide and high tide went, Oh, cool. It's just an app is basically calendar. So we did. We kind of messed around a lot with stupid stuff like that. But the Dafur a bit, the last startup that I worked at was airline company, and I think I was hired to do another backend reservation system, and they kind of moved me over to a more project management role.

Chicago13: [00:02:31] So I did that for a little bit. And then kind of a turning point was when I was sleeping in my car because I didn't want to bother my friends too much. I've been doing that for months, so living out of a car for about a week and I was like, Hey, I need to do something more stable. I remember parking into like, you know, nice Palo Alto areas and then kind of sleeping in in my car and then leaving right before the joggers would come out. So I did that. I was getting a stipend for like 500 bucks a month at the startup and then like was promised like all these great options, but I don't think that really materialized. So doing that, I was like, I can't do this anymore. So I took the LSAT surprisingly well without much preparation. They went to law school. So did that, got a good scholarship and then went in with the idea of doing IP law because that kind of married my interest of the legal protections and also technology.

Chicago13: [00:03:31] So I did that for a bit in law school and focused on that kind of stuff and found out that wasn't for me. You know, through coursework and through my internships, you know, in the summertime. So I ended up going to corporate law route really focused on M&A and corporate finance. And did that at a top ten New York based law firm did that for about a year. Really focused on M&A. It didn't like it too much. I felt like as a lawyer that I was the last to know anything on the deal when I would ask people or ask my partner, you know, why did we make this decision? Why do we concede on this or that provision? The answer was always to get us to business decision for business guys. And that was like, Hey, I want to be a business guy. I want to understand what's going on. So I started looking at different opportunities in investment banking, made the switch in about a year, something that my current bank, it's a middle market bank, really focused on technology and business services. But for about six years now, that's awesome. Now I started out as associate rose up to VP.

Patrick (CEO of WSO): [00:04:36] So, yeah, kind of where you started, when you went from law school to banking, you were able to transition as an associate, right? Like a first year associate, basically.

Chicago13: [00:04:46] I was, yeah. And to be honest, it was a tough transition because I I'm sure I'm trying to manage these analysts, you know, everything. They've been at the bank for two or three years. And well, let's start before,

Patrick (CEO of WSO): [00:04:57] Let's start earlier, because I think there's some really interesting stuff to unpack. Let's go back to Berkeley. So West Coast kid, you're kind of you get into Berkeley. You're obviously pretty sharp because Berkeley's not easy to get into. And you are. What's what are you doing there like? Did you want to major in your parents are pushing you to med school? So were you like pre-med to start?

Chicago13: [00:05:19] Yeah, I was pre-med for a year. I had no idea what I wanted to do. So my I come from a background of my family are all professionals. It's all they know. So anything entrepreneurial, anything in finance, they don't know what that is. So what,

Patrick (CEO of WSO): [00:05:31] What kind of professionals? When I told it, like medicine and lawyer and lawyer, legal

Chicago13: [00:05:35] And yeah, medicine and lawyers, yeah. Basically medicine lawyers. Yeah.

Patrick (CEO of WSO): [00:05:40] And so that's all I knew. When you told them, when do you start ups? Because it's 06, when you're graduating and everything is super hot in Silicon Valley, what was the response?

Chicago13: [00:05:50] Yeah, so that was I mean, it was it was dumb. I kind of tend to agree. I think maybe for me, I didn't have the technical background. I kind of picked it up. I think up programming and trying it out. I just wanted to. I wanted to do something with my friends. I think that was probably the wrong decision. But tell me at the time,

Patrick (CEO of WSO): [00:06:11] Let's unpack that because I think a lot of kids had that. Maybe not so much. Now with everything going on, everyone's looking for safety now with COVID. But tell me, let's unpack like that that idea of in a frothy market, maybe not 06, but maybe like even a year ago, people were maybe thinking, Hey, startups are where it's at. Tell me, like what went into the thought process? Maybe it wasn't much, but maybe it's just a Hey, I want to work with my friends. I think we could make this work because we're smart guys or gals. And what happened? Like, what was the first attempt? And did you have any sort of cash flow coming in when you first graduated? Like, was there something leading up to that gave you confidence that you could do it?

Chicago13: [00:06:48] Well, I had really bright friends kind of going off their ideas and kind of going off their technical experience. I think we really got caught up in the idea of the dream basically of, you know, we were seeing all these what we thought were dumb companies come up and just create amazing products that everyone started using. And we thought it was not bad ideas that turned out to be great. I mean, I remember there was a guy called Justin TV News record himself doing playing video games, walking around. It actually became twitch. And I was like, Wow, that's amazing. We thought if you did anything in tech related, I thought there's a chance of making it big. And I certainly think that my friends had the I had these skills and kind of the drive and kind of the vision to do that. So where did

Patrick (CEO of WSO): [00:07:39] You come in? Were you the business? Were you supposed to be the business person

Chicago13: [00:07:43] Or just absolutely the business person I got? I got to grow up into the coding part of it, too, because if you can't sell your product, no one's buying it, then there's not much for you to do. So I got more into the development side of it.

Patrick (CEO of WSO): [00:07:53] So this is you graduate 06 in what may or June finish classes and then like in May and then like, how much do you have to your name? Are your parents still funding you? How do you convince them to actually pay your rent? Or are you just because like at this point, it sounds like you're really just starting up with a couple friends? Is that accurate?

Chicago13: [00:08:09] Yeah, yes. Yeah, I think that's right. That's right. So I mean, I had a couple of savings just from working in the summertime, so I had thoughts about going to law school. So I had I worked at a law firm for a year in the summer time before that, so I had a bit of savings, wasn't it like I wasn't living expensively? I was living in like a one bedroom with like two other people.

Patrick (CEO of WSO): [00:08:29] So you had like twenty thousand dollars or something saved something like that?

Chicago13: [00:08:34] Yeah, about like fifteen thousand fifteen.

Patrick (CEO of WSO): [00:08:35] Yeah. So you can you can stretch that if you live really cheaply.

Chicago13: [00:08:39] Yeah, yeah, you can. And then I never had a bus pass. I like bought like a bus sticker off a current student at Berkeley. When I graduated, I did that to get around. So that was interesting times. So you

Patrick (CEO of WSO): [00:08:50] Were hustling. Ok, so you're starting one thing the next. Did you ever have an idea that started kind of getting traction or any revenue from any of these ideas? And because it sounds like you didn't go to law school for four years?

Chicago13: [00:09:03] Yeah, I think it last for four years, so

Patrick (CEO of WSO): [00:09:06] You were trying for a while like you kept at it, so tell me like the. Any sort of exciting kind of trends in there. It sounds like you eventually joined a slightly larger startup, the airline one to kind of maybe try and get something more stable. But for some reason they were kind of not paying you or paying you really, really low. Can you tell me about I didn't like what he told me, what to look out for kids that like because you're obviously a sharp kid, but like, is it because you didn't have like any sort of skill set you could bring or point to? Like, why did you why do you feel like they were able to do that and pay you so little? At Great Financial Crisis, like,

Chicago13: [00:09:44] No, no, I think for me, it was it sounds cool. I mean, that's kind of the simple answer. Probably not the best answer, but I think they found naive kids like me. I think everyone that I worked with was pretty bright. But I mean, they're just fresh grads or newly grads and the opportunity to work on a private airline company, it was pretty cool. So I mean, I got roped in that way. We thought that we were building. I think I mean, they became something substantial. So I think in the end it did work out. But at the time when I was there, it was a lot of hurdles and regulatory hurdles. And I think a kind of a warning sign with kids, maybe when they're choosing startup opportunities is looking at the strength of the founder. And we had a strong founder, but I mean, it was just him. I would tend to be if I were to go back, I would look for people who. Calm are have deeper teams, not just not just one guy. Pretty much. And then, you know, one guy. You know, you want someone who lives and breathes this stuff. I think my boss is more of a lifestyle kind of guy. You kind of see him once in a while. Drop in. Try to be the cool guy. But if you really want to, if you really want to succeed and start ups, it's a difficult world because you're not generating revenue. You're burning through cash. You want someone who's obsessed with the product, with the vision, with their go to market strategy. Everything so. So I would, I would say, follow. Someone is super passionate, not just someone who's doing this as a side gig or site passion.

Patrick (CEO of WSO): [00:11:26] I think that's great. Or maybe somebody who's had a few rounds of successful funding and are on the right trajectory, right? If you want

Chicago13: [00:11:32] To get that to you.

Patrick (CEO of WSO): [00:11:33] Absolutely. Or super early. But they're willing to kind of not just say they're going to pay you, but like actually put something in writing and maybe, yeah, actually give you options.

Chicago13: [00:11:48] I got the I got the option, but like, it was not much. And then I mean, they were upfront about payment. But I think, you know, I think when you're hungry and when you're a kid or when you're young, I think you just go for the riskiest thing. And I would caution the listeners that don't always do that, always protect yourself. And, you know, take your time and taking opportunities like you don't have to rush into the first thing that you find. I made that mistake a lot.

Patrick (CEO of WSO): [00:12:17] So did you you'd get excited by whatever company you're looking at and then just jump, basically. And so how many different companies you work for? I know that airline was the last one, the private airline, but what was the was like five before? Was it you for the first couple of years with your buddies trying to make it work? What was the kind of trajectory of that?

Chicago13: [00:12:35] Yeah, so it was I've worked out, probably it was mostly groups of my friends initially and then I

Patrick (CEO of WSO): [00:12:40] Was the reason. The reason I'm asking this is because I really kind of want to break down. Like the ebbs and flows, like, was it like obvious that there was a failure, it was like there were middling success somewhere and you guys are like, then chase that for a year, you know what I mean? Like, was it? Yeah. You know what I mean?

Chicago13: [00:12:57] That type of, yeah, yeah. There was some success early on where there was interest, you know, with one of our apps. So we chase that. That became nothing in the end it and then we tried again. So that took about two and a half years or so. And then I was running out of money, obviously. So I took a lot of temp jobs. So that kind of that delayed kind of my switch over to law too.

Patrick (CEO of WSO): [00:13:24] I worked at you when you were sleeping in your car in Palo Alto and driving kind of just because you had been sleeping on couches for your friends places for a while. Yeah. And you didn't want to bother them. What's going through your head? There are you. Are your parents saying I told you so at any point, like, what's the are they pushing you still to kind of consider law school? What was the whole?

Chicago13: [00:13:47] Dynamic, yeah. My parents are pretty cool. My parents are East Asian, so they're from a background of, you know, education's everything, but my parents are pretty cool. And yeah, they were supportive. I think they thought that I'd figured out in the end. Mm hmm. And you did. Yeah, I hope so. Yeah. Yeah, I one one regret I have, though, is I had I don't know how I got this offer, but straight out of college I got an offer to go to a large hedge fund. You know, at the time was one of the large hedge funds in the world, and I didn't even know what a hedge fund was, but I got the opportunity and I turned it down to create like a surfing app. So I always feel like potentially maybe that was not the right decision.

Patrick (CEO of WSO): [00:14:32] It.

Chicago13: [00:14:32] And then looking back at my kind of how my career has progressed, you know, investment banking, you know, when you join, obviously, as you guys all know, you join as an associate and move on up those opportunities on the buy side is limited. So if that was something I wanted to pursue, it wouldn't be open to me today. I feel it would be a lot harder.

Patrick (CEO of WSO): [00:14:50] It's harder. Yeah, I mean, it's still possible, but it's hard. So tell me a little bit about so that kind of that final straw that broke your back. You realize like this is not sustainable. I'm getting like these tiny stipends, working these temp jobs, sleeping in my car, moving my car. At that point, you're just like, I just got to take the Elsa, I just got to go figure something out that was just kind of, did it come to you like one day or you're like, I just had enough.

Chicago13: [00:15:16] Like, I'm. Yeah, I think when you're young, like you get to a certain point where you start comparing yourself to your friends, you do less of that in your thirties. But when you're in your early to mid 20s, you're like, Am I getting behind in life? And I didn't know I just wanted. I remember thinking, I always want to go to Safeway if the grocery store chain on the West Coast, and I just won't have to worry about buying groceries. I remember that was a huge thought that I had, and I was I didn't want to ask my parents for money because they paid for my college. I felt like I did. They did enough for me. I didn't want to ask for more, so I just wanted to be self self-sufficient. I want to be self-sufficient.

Patrick (CEO of WSO): [00:15:57] Yeah, yeah, that was my big thing coming out of college. I just didn't want to like rely because my parents paid for my college, so I didn't want to fly anymore. I was like, That's enough. That was expensive, you know? Yeah. And so, yeah, I get it. So OK. So you take the L say you do well, you get into a great law school with some, with some aid, it sounds like, which is awesome. Yeah. And then. You end up going, you're kind of interested in IP. You end up going kind of just the big, big law corporate law route with everything corp fin. And so how did you do a summer associate role like with that same firm like that summer or one of the summers?

Chicago13: [00:16:38] During. So, no, I did not, so I actually I summer, I did my summer associate a different kind of big law firm that was more litigation focused.

Patrick (CEO of WSO): [00:16:46] Ok, so tell me like what your thought process was? Was finance ever even on the radar? Ever. You probably wouldn't be at law school. Was my yeah. Was it ever on the radar?

Chicago13: [00:16:57] Yeah, it wasn't. It wasn't until I went. I did that summer internship, my second between my second and third year. So it was a litigation focused, big law shop. But I did a rotation program across restructuring corporate IP, so they put me through the different rotations. And I thought I would like IP a lot and I didn't like it at all.

Patrick (CEO of WSO): [00:17:19] Interesting. Your little more. You found restructuring in the other side. More interesting.

Chicago13: [00:17:25] Yeah, definitely. It's much more interesting, I felt like. Yeah, I just felt like it was more teamwork oriented or litigation still adversarial, like you play these little games like

Patrick (CEO of WSO): [00:17:37] Like referees for the party. I feel like restructuring that for you. I mean, when I was, I was in restructuring at Rothschild for a couple of years. And I remember those meetings in those negotiations, they were pretty, pretty and pretty heated. I mean, you're talking about like hundreds of millions of dollars in negotiating right there and back and forth, and it took years to get to Chapter 11.

Chicago13: [00:18:01] But no one's happier in those in those Typekit.

Patrick (CEO of WSO): [00:18:05] No one's happy or the banks happy and the lawyers tend to be happy, right? Because they're making bank. But yeah, tell me about. So tell me about. So it kind of was a little bit on the radar. And then and then once you accept it, kind of this big law firm and you started working. At what point was it like within the first three months? You're like, This is not going to work out? And was it was it ours? Was it pay? What was the pay is pretty good for you at the top firms you're making like a good three hundred k a year. So this is the first time you're making like,

Chicago13: [00:18:35] No, you're making, you're making your starting salary then was implied was 160. It's stable.

Patrick (CEO of WSO): [00:18:41] So it's like, so it's like two hundred. Ok, yeah. I'm thinking more like now. But is it like with everything? It's like two to 30 to 40.

Chicago13: [00:18:48] I think now it may be

Patrick (CEO of WSO): [00:18:50] Ok now, it may be OK, so back then. Yeah. Ok, so your salary similar to like the banking associate, but the bonus is nowhere near it.

Chicago13: [00:18:59] No, there's like the bonus, I think my first year was like 10 grand. Yeah, OK. I think it was like 170, and now it's like low to hundreds. Kids out of law school.

Patrick (CEO of WSO): [00:19:08] Ok, so that makes sense. So but you're tell me about your hours. They're just brutal, right?

Chicago13: [00:19:14] Yeah, it's pretty, pretty brutal. I mean, up and down, up and down, but I mean, there's an inconsistent and yeah, it's I think it's similar to banking. Yeah, but your role is. If I were to compare it to banking, your role is more similar day to day, you do the same thing over and over again. Whereas in banking, it's pretty dynamic depending on what phase the process you're in. If you're doing M&A, you're doing equity offering or whatever.

Patrick (CEO of WSO): [00:19:42] So you're kind of there for how long before you're thinking, I got to get out of here.

Chicago13: [00:19:46] Yeah, I think within the first three or four months, so not not very long, and usually they try to take it pretty easy on you to kind of kind of get you to buy into the firm culture and all that. But I was learning a lot, but at the same time, I want to learn faster. I mean, I was looking at the bankers on the other side of the deal and, you know, they seem to know more about what was going on. They were closer to the client. They were advising the client from start to finish, whereas I felt like as an attorney, we were brought in as a hired gun at the very end. Yeah, to like paper up decisions that have already been made. So I didn't feel involved in the decision making process, and I that was not, I don't know, for some reason that kind of didn't sit with me the right way, and I really wanted to think about how I was spending my time professionally. I wanted to be kind of the more the most value additive for my client.

Patrick (CEO of WSO): [00:20:41] That's fair. Ok, so you kind of had this epiphany, OK, this is not the right place. So I want to go be those guys. I want to be in banking. So how the hell do you make that transition? Because it's super hard. You just spent three years getting a job before that. You just have startup experience and then you're now at a big law firm. At least you're at a good firm. So there's some that help a lot. There's some respect there. They're like, OK, well, this guy's smart, but tell me how you went about just the entire networking process. Like, what store was it? That story you just told me, was it kind of the summer thing like, I want to be the one to understand this is that is that kind of what you told them?

Chicago13: [00:21:18] Yeah, that was it. Yeah, basically. And the hardest part for me, I think the story was easy to tell. I think they believe that their quality is that carry over from lots of banking, like attention to detail and your hardworking. They know you're going to grind so they don't have any concerns there. I think the burnouts actually hire them. Also, they like that fact, too, so they can't be. Those are all positive aspects.

Patrick (CEO of WSO): [00:21:42] The composition of the comp is higher at the law, at the big law firm than it like a middle market.

Chicago13: [00:21:47] No, no, no. Investment banking yeah.

Patrick (CEO of WSO): [00:21:49] Yeah. But so for now, it's yeah, I get what you're saying.

Chicago13: [00:21:53] Ok, so you're coming from a worst place in bankers minds, coming from big law. So I think they are capable and you can put up a lot. So that's what I'm trying to say.

Patrick (CEO of WSO): [00:22:03] So why would they hire you and not just some kid out of MBA? And how did you convince them to do that?

Chicago13: [00:22:08] Yeah, I don't know that was hard because I don't have the the hardest part for me was a technical because I didn't I didn't take a finance class, I didn't take accounting when I was in college or in law school. Yeah. So it was a matter of me just reaching out to people on LinkedIn, you know, using services like Wall Street, like Wall Street, Oasis and like using that type of service where you're trying to get coaching for interviews. So I booked a couple of sessions through a competitor of yours and, you know, got guys got help that way, and that helped a lot.

Patrick (CEO of WSO): [00:22:39] Yeah, that's big. Getting reps is like huge, especially if you have a technical background. So did you. So you're you're kind of studying up on your technicals, your accounting. You're doing any like financial modeling, training to.

Chicago13: [00:22:50] I did, yeah, good. Yeah, I signed up for like training the street. Yeah, you know, got old guys from. For my business girlfriends, like they would send me their old three industry materials and looked over that book that while YouTube videos accounting for dummies even, did that help?

Patrick (CEO of WSO): [00:23:08] Did you feel like it helped you become a little more dangerous than the interviews?

Chicago13: [00:23:12] I mean, I felt, yeah, I mean, I apparently after the fact, they thought my technicals were superb and I was blown away by that comment because I thought I had barely squeaked through. I knew just enough to squeeze squeak by and if they were to ask a lot of questions. Next level deeper, I would have totally flat failed.

Patrick (CEO of WSO): [00:23:28] So tell me, so tell me about that. Like that process? Or how many? How many like it sound like you were networking and talking with a lot of people? So that was a good start. Like just coffee chats and stuff. And how did you find time given all you sneaking out for lunch and stuff with bankers?

Chicago13: [00:23:44] Yeah, it's mostly on the phone, and then I was in New York at the time, so that makes it easier because, you know, they're all in midtown or, you know, they're all concentrating one area. Yeah. And I started with my friend group first and then had friends of friends connect me and then. And then this went through that multiple times, and then how long did

Patrick (CEO of WSO): [00:24:03] It take for you to like, start getting interviews?

Chicago13: [00:24:06] So I think I would say within a month and a half or so, I might get out of that pretty fast. Yeah. And then once you get an interview, move so fast, we have no time to prepare.

Patrick (CEO of WSO): [00:24:18] Is this is this? Was it one of the first places you interviewed? That is where you ended up.

Chicago13: [00:24:23] No, it's actually one of the last I had trouble getting an offer.

Patrick (CEO of WSO): [00:24:27] So tell me how many people? Yeah, tell me how that doesn't surprise. I was going to be shocked if you like with the first place you talk with. How many places we can strike out with before you kind of got that offer.

Chicago13: [00:24:37] I would say, I don't know too many places. I feel like maybe over 10 10.

Patrick (CEO of WSO): [00:24:41] Yeah. Yeah. Did you start feeling

Chicago13: [00:24:44] Like it was like both brackets? You know, middle market. It was boutique is everything that I could get my rep on, even though like it was a place I knew I didn't want to work at. I would still go for that interview because it was practice.

Patrick (CEO of WSO): [00:24:55] Yeah. And so did you feel like you got a lot better, obviously, as you went along, but in the tech, you got more confident with the technicals, all that stuff, your story got tightened up. Did you feel like at any point like, I'm not going to this is not going to happen. Like nobody makes this jump.

Chicago13: [00:25:10] Feel like I was pretty. Yeah, no, I thought I would get. I knew I would get something, but I just didn't know how given opportunity to be. I had doubts about that. Yeah.

Patrick (CEO of WSO): [00:25:22] Ok, so you finally kind of get through to some final round at this middle market banking right now and things go well, you get the offer, and I assume it's something like one twenty five base. But the bonus opportunity is just massive, right? And it was it specifically for like M&A.

Chicago13: [00:25:38] Grouper. No, not specifically very many, but kind of emanate more M&A focused. I was in a industry group.

Patrick (CEO of WSO): [00:25:44] Have you heard of any other associates, legal associates kind of jumping and making a similar move to you?

Chicago13: [00:25:50] So I'm seeing more of it now, and I'm seeing more people from my network reach out to me who are lawyers want to make the jump. But when I was, this is six, seven years ago or so I thought one or two examples, but not too many.

Patrick (CEO of WSO): [00:26:03] Yeah, yeah. Ok, so you started as an associate? Tell me what the transition was like. You said you initially mentioned it was really hard, but tell me why it was hard.

Chicago13: [00:26:11] Yeah, because. You have of that when you start because you feel like you're. I felt like I was trained for any of this. I felt like everyone else had the technical training and these are all things you can pick up. But when you first joined, you have these doubts and you see the analysts you're supposed to be managing know so much more than you like. They'll just run circles around you.

Patrick (CEO of WSO): [00:26:33] Imposter syndrome or whatever they call it.

Chicago13: [00:26:36] Yeah. You're like, Yeah,

Patrick (CEO of WSO): [00:26:38] You're just like, I don't know. I can't do that like. I think that's super common, even for MBA is for the analysts to run circles. So you shouldn't feel bad. But yeah, you're coming from a legal background. It's tough.

Chicago13: [00:26:48] And I see that from MBA people, MBA folks who just joined. It's hard. I guess when you go in without the analyst training because those analysts are the reps alone that make them so good. Yeah, but at the same time, you have to realize they don't have always the maturity or the professionalism, and they are not good at project management. You have to understand that you have a different role than they do. Yep. So you don't have to be good at everything. You've got to find some things gear that and then have the rest of the team complement you. So that's kind of how we went through it for myself. It was difficult because I didn't understand all the technical. It took me about, I think, a good six months for me to understand all that kind of intuitive detail. Yeah. So you know how to read a financial statement. Even as basic as that, I was starting to score zero. So that took a little bit of time to ramp up. Sure.

Patrick (CEO of WSO): [00:27:39] Sounds like me coming out of a liberal arts background. Going into my analyst program is brutal. The first thing? Brutal. Man, that training not get you ready. Anyways, so it doesn't you just need the wraps, right? You need the wraps you need to spend, yeah, 50 to 100 hours a week in Excel and PowerPoint doing it.

Chicago13: [00:27:58] Oh, for sure. Yeah, yeah. Anyone can learn it, but it just takes time.

Patrick (CEO of WSO): [00:28:01] Yeah. So OK. So you're kind of going through the associate after that six months, things are getting kind of easier. You get more confidence. Tell me how things progress with like the promo to BP and how long that took, what that was like in terms of like your superiors telling you, Hey, you're doing a great job or was there any like any time you felt like I'm going to lose my job?

Chicago13: [00:28:22] Yeah, I think that first year I thought could lose my job all the time because the hours are brutal, like there's no feedback, really, you have to kind of seek it out in investment banking. Yeah. No one's going to tell you for doing a good job or a bad job. Well, I guess I'll tell you if you get a good job, but you really don't know if you're doing a bad job until review time. Yeah.

Patrick (CEO of WSO): [00:28:39] And how about you? What is that six months in?

Chicago13: [00:28:43] Uh, yeah, I guess the mid-year, like they don't really tell you anything, you're mid-year and then at the end of the year, they're like, Well, you could have done this and this and this. It's a little unfair. And this is why we're going to dock your comp this much, you know? Yeah, yeah. But I was happy to survive that first year.

Patrick (CEO of WSO): [00:29:02] Do you mind? Yeah. Do you mind shooting from where your camp was just to give the listeners an idea?

Chicago13: [00:29:08] Yeah, I think my all in I think my back then, I think my comp was I honestly was like one five base and then I think my bonus was around another hundred to twenty five. So I got about 225 to 250, I believe around there. Ok. So, you know, a little bit more than I was getting paid at the law firm, but not substantially more.

Patrick (CEO of WSO): [00:29:30] Were you working long hours?

Chicago13: [00:29:34] Um, I think I was I think I was working longer hours

Patrick (CEO of WSO): [00:29:37] Because you're drinking, you're probably in the first six months, especially, you're like, What

Chicago13: [00:29:40] The hell am I? Yeah, because I think because I'm inefficient and it takes us longer, you know, I think that was probably the big reason why I think if you if you're if you probably better than I was, it probably would have been more manageable.

Patrick (CEO of WSO): [00:29:55] Ok, so you're you do pretty well actually for that first year. So they probably had some decent things to say after that after year one, like you're getting better. Yeah, for sure. And then that second and third year, was it just big pay raises because you I mean, you eventually got promoted? Was it like three years and then the promo?

Chicago13: [00:30:15] Yeah, I can say about three and a half years or so before the primary promotion. That was a steady increases up. And I think it's just a matter of you have to understand getting a promotion is also very political. So the very beginning, I was working with same people in over and over again, and I didn't have a lot exposure to the rest of the firm. And I think that kind of hindered my progression or like people didn't know who I was, even though I was there for a while. Yeah. So I think if you want to get promoted, I think you have to have that into consideration. You got to talk to your staffer and try to get on, you know, a broader type of deal so that you're known across the firm and you're trusted because that goes a long way.

Patrick (CEO of WSO): [00:30:53] And that means like getting into M&A, if M&A is hot, that type of stuff getting on some of those. Basically, yeah, yeah, that makes sense.

Chicago13: [00:31:02] Or different verticals to if you can get into it within your broader group, got it.

Patrick (CEO of WSO): [00:31:08] That makes sense. I mean, yeah, so you'd say, would you say that's true if like, let's say you're in a certain team in a certain silo and that's like the most respected team of the bank. And you guys, you're just crushing it with big deals. I mean, then you're probably going to have a fast track, right? Or no?

Chicago13: [00:31:24] I think so. Yeah. Well, maybe that's probably true. That's probably the case. Great bulge bracket. I think I'm coming from a middle market bank where we're not as siloed. We're more kind of free agent crowd.

Patrick (CEO of WSO): [00:31:34] You were still pretty. You were getting you're still getting siloed in that middle market. So it was almost like you weren't getting exposure, even though it's not even a huge bank, but you still weren't getting that kind of exposure. And so it was almost more important to be a generalist there and get broad exposure. There was no one place that was as super dominant or like you could ride it up all the way.

Chicago13: [00:31:53] Well, my bank, you know, especially used to have very broad groupings and it's got like a technology group is like super broad. So it's, you know, every vertical you can think of is part of that. So it's not working with more than one MBA Patrick (CEO of WSO): [00:32:10] Yeah, that's fair. Ok, so tell me about like how so that you said the pay went up? Eventually, you're making like four or five hundred, whatever as a VP. But tell me about just like how things shifted and changed with your role. Obviously, you start just managing more and like more hands off from the MDS. Is that is that accurate?

Chicago13: [00:32:29] Yes, so there's more direct communication with MDS. You're basically there, right hand execution support, so everything is filtered through you and it's your job to not just crank anymore is to actually put thought behind either the marketing materials, the analysis, whatever it may be.

Patrick (CEO of WSO): [00:32:46] Was that hard for you or that was easier transition for you?

Chicago13: [00:32:49] I liked it more because you have time to actually think. So I feel like, yeah, for sure. And then the details, you know, the analysts and associates, you know, the first pass of figuring that out and your level of thinking is devoted more to kind of structural things like the more important concepts they trying to get across.

Patrick (CEO of WSO): [00:33:12] Can you tell me about that? Like, is it like the way the deal is structured? You mean, like in terms of like

Chicago13: [00:33:16] Finding, Oh no, no, no, no. I mean, like an analysis structure like how you want to lay out a model? Got it. This is this is how you want to structure it. It's more your time is more spent on kind of framing things in ways to make it more intuitive and framing it for buyers to understand more detail oriented.

Patrick (CEO of WSO): [00:33:35] Fair. Okay, so you're doing you're doing a lot of sell side stuff.

Chicago13: [00:33:39] Yeah, I do like all sides. Got it. Yeah, OK. More and more besides.

Patrick (CEO of WSO): [00:33:43] Got it. Ok. And then. I'm trying to think what else anything else you'd want to share in terms of your progression or the things to watch out for because you mentioned something about talking to your staff or to try and get on that broader thing. How do you like navigate those kind of what can be kind of touchy and political conversations? Did you feel comfortable doing that or just you do it respectfully? How did how did you approach it?

Chicago13: [00:34:07] Yeah, so I'm not a political person at all. You know, I I don't want to I don't like to play the game where you try to support someone who's powerful and the firm trying to move up. I try to do it my own way and hope people realize. And if they didn't, then so be it. So I don't think I'm the best person to get advice from on that front. But I think if you're genuine and you put in the hard work and you try, I mean, that's all you can really do and people will notice it eventually. Yeah, and just be a team player. I know people get really stressed out and banking, but really like it's just money moving around. And if you take a step back, no one's going to die. And it seems like it's going to end the world, but people get over it. So even if you make a mistake, don't kill yourself over it. Move on. Someone's being a jerk, then whatever. Screw them, just move on. You know, I think one of the things that you got to have a thick skin to survive in any type of role in finance because it's a very harsh world and nothing personal. I think that's something that you have to realize and treat your team members with respect, no matter who they are.

Patrick (CEO of WSO): [00:35:07] And when you say that, like is it? Are you saying that because like there were several times where like there was super high pressure stakes on you as an associate or V.P. or whatever and like you got screamed at by the client or by the MD or whatever, and everyone was stressed out? Oh, absolutely. Yeah, absolutely. He share like, you know, the specifics, but like, can you give me an example? Like, there is a busted number in the model and you guys gave a presentation to a client. Is there a story you could share?

Chicago13: [00:35:28] Yeah, for sure. So remember, we had a Christmas party for office, and then with the happy time, then I get this call from my VP at the time and we're working with a pretty growth oriented client. So typically a smaller deal than we're used to. So their financials are not very strong and you know, we had to rely on them to get the support for the data to build the model. And we're trying to go out to buyers. I think that next week or so and we're building out this model and the numbers don't tie, nothing makes sense. We can't explain to the VP why this isn't working. And I remember it was like I had like a couple of beers was feeling pretty good and then I'm on the phone getting yelled at by BP. And it was not a fun experience, and that was not just because it happened a couple of times, actually not just on that deal, but other deals.

Patrick (CEO of WSO): [00:36:20] Was that in your first six months where you were like panicked because like. Yeah. And that's normal, though, like, you didn't have those. You didn't have the modeling skills yet. Right.

Chicago13: [00:36:29] And I think, yeah, I don't have the molecules. And also you defer a lot to your client like the CFO at the company and you just take their word for the support. And if you take a step back, it doesn't make sense. So I had a hard time kind of challenging my client because I felt like, you know, they know better than I do. But that's part of your role, even though you're a kid or you feel like a kid and they're like a grizzled veteran, you got you got a question there,

Patrick (CEO of WSO): [00:36:55] Especially when it doesn't make sense. You should be able to step back and be like, I don't understand this. Can you explain this to me? How does this tie, you know, that kind of thing?

Chicago13: [00:37:02] Yeah, pretty much for sure. It's important to make things tie.

Patrick (CEO of WSO): [00:37:07] That's awesome. Well, yeah, that was unfortunately a short, short lived good time at the Christmas party, but yeah, hopefully I think everyone goes through that. I remember my analyst days. I had some really stressful. The first six months it was the worst. I had a guy who was my associate who had just come from HBS, similar kind of no banking background. I'm clueless because I'm coming from a liberal arts. He's clueless because he was in the background and it was just like, he's like, I'm going to let you handle the model. I'm like, OK, but I have no clue what I'm doing is they still go ahead and I'm like, I really have no clue. Like, I don't I don't know what to do. And so I think it was kind of like blind leading blind. It was it was bad. Eventually, what ended up happening is the BP eventually just took me into space. You showed me and entered me, and he ended up doing a couple days and then ended up getting fired six months later because I think he was very much like didn't really want to put it in. It wasn't exactly a team player. I was checking out early. Like this guy, this guy's, it's just not going well. And, you know, I was working nine hundred hours. And so like people, right, at least recognize that you're trying. Yeah. You eventually get it. You eventually get it.

Chicago13: [00:38:22] So it feels like you'll never end, but you could get it.

Patrick (CEO of WSO): [00:38:26] I appreciate you being so candid and sharing all this. Any anything else you want to end. And the pod with any kind of words of wisdom. I think the I think you've really shared a lot, but anything else before we call it.

Chicago13: [00:38:41] Yeah, I think I probably said this before, but just be nice to people like you're going to if you're an analyst, you know, be nice to your associates going out and be a program who who's trying to add value by making do things what you think is not additive like still, just try to take their advice and try to learn from them. Don't, discredit anybody that you work with, especially your team member, because, you know, we're all in this together. We're all trying to do the best we can to try to try to come at it from that perspective. And I think your experience will be better if you do that, if you can keep that in mind.

Patrick (CEO of WSO): [00:39:15] I love it. Great go teamwork. All right, man. Well, thanks so much and we'll be in touch. We'll talk to you. Thank you. 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.