WSO Podcast | E158: Corp Dev at DropBox & Twitter after IB Stint at Perella
About
In this episode, we learn about Calvin's path from investment banking at Perella Weinberg Partners (PWP) to corporate development at some of the top technology firms in the world including DropBox and Twitter. Listen to hear how he broke into investment banking out of Berkeley, the big risk he took going into his senior year and what it's really like working on the inside of one of these tech darlings. We talk about pay, lifestyle and some great advice for those of you looking to follow in his footsteps.
WSO Mentor
Want to work with Calvin? Check out her profile here!
Or Listen to the Podcast Here:
Apple Podcasts
Spotify
Stitcher
Resources:
WSO Podcast (Episode 158) 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 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 learn about Calvin's path from investment banking at Perella Weinberg Partners to corporate development at some of the top technology firms in the world, including dropbox and Twitter. Listen to hear how he broke into investment banking out of Berkeley, the big risk he took going into his senior year, and what it's really like working on the inside of one of these tech darlings. We talk about pay, lifestyle and some great advice for those of you looking to follow in his footsteps. Enjoy. All right, Calvin, welcome to the Wall Street Oasis podcast.
Calvin: [00:01:01] Yeah, thanks for having me, Patrick.
Patrick (CEO of WSO): [00:01:03] So it'd be great if you could just give the listeners a short summary of your bio.
Calvin [00:01:06] Yeah, sure thing, so I did my undergrad at UC Berkeley. I had a focus on economics. And yeah, I think towards my junior senior year, it seemed like banking was the hot thing to do for people who wanted a career in business to be perfectly candid, had no idea what banking was.
Patrick (CEO of WSO): [00:01:28] But like a lot of this, like a lot of us,
Calvin [00:01:30] Yeah, exactly right. You grow up and you think, you know, banking is kind of, you know, you go to a teller, you go to an ATM, but there's a whole other industry kind of behind all of that, right? So yeah, I decided to invest in banking. I've always been kind of a very finance and numbers oriented guy, at least kind of at a macro level that always made sense to me. So after college, I worked at Perella Weinberg Partners, which is a boutique bank. There's offices, of course, kind of across the world. But I worked out of San Francisco focusing on tech M&A, and we covered a pretty broad range of both sectors within tech, as well as kind of types of companies, both from large, well-known blue chip names to small startups. Yeah, so I did. A couple of years up, Perella worked on a number of different types of transactions. It was a great learning experience, but I never really considered myself a long term banker. I thought the industry was a great way to ramp up on certain kind of skills and foundations, but I've always wanted to get to that next layer deeper. It's great to advise companies on how they should think about capital raises and M&A. But it's different where you're kind of sitting in the driver's seat and really kind of thinking about that at a more strategic level and being able to make an impact at that level, right? So I knew I want to jump to tech and corporate. And luckily for me, obviously within San Francisco Bay Area, there's a lot of great tech companies that are growing quickly trying to become more acquisitive. I jumped after a couple of years to Twitter. I was on their
finance and M&A team for a couple of years to work on a number of different types of things, including we made an investment in a music company called SoundCloud, and we worked on a number of different.
Patrick (CEO of WSO): [00:03:17] Yeah, great.
Calvin [00:03:19] Yeah, yeah. It's a cool community, obviously not at the scale of Spotify, but really a lot of unique content on that platform. So very much fit the cultural vibe over there on Twitter. I'll Twitter for two years and then jumped over to Dropbox, where I was an early member of their corporate development team. I think a scene for me was always, I love working on companies where I use the product right. I am a Twitter user. I've been a Dropbox user since college, so I understand the product. I like the product and that's that's kind of a recurring theme as I kind of continue on my career journey. But yeah, I was a Dropbox for two years as well helped them kind of ramp up the M&A efforts there, worked on a couple of acquisitions and partnerships as well. And yeah, I think about two years ago, I started getting itch within tech. There's always there's so much growth and so much disruption going on. And by no means are
Twitter and Dropbox companies that are mature and no longer disruptive. But you always kind of want to go earlier stage, always work out in your flash form somewhere that's a little bit unstructured so I decided to look earlier stage and fintech has always been an interest of mine, especially on the consumer side, just a lot of innovation really in that space to be had. And I feel like we're still very much in the early innings of that. So I joined a fintech consumer. Fintech called Chime was their first strategy and corporate development hire at the time was a fairly small company. Just one hundred and fifty people, probably at the stage where they're starting to think about, you know, hiring the first deaf person. And hey, maybe we should start making more acquisitions. So yeah, I've been here for about a year and a half. It's been a great, great ride so far. The company is doing amazing, amazing things.
Patrick (CEO of WSO): [00:05:09] That's so cool, man.
Calvin [00:05:10] Well, very impressive background.
Patrick (CEO of WSO): [00:05:11] I want to start all the way back at Berkeley. So yeah, kind of. You started school right after like as the global financial crisis hit the bottom. And so I'm curious, I would think that people kind of that started college around when you did wouldn't kind of. Be, you know, putting investment banking at the top of their list. Were you always thinking like finance was for you? I know you said you're good at numbers, all the stuff and you didn't really know what it was in college like, like most of us. It's just kind of a good path. I'd love to hear like, you’re an econ major. You probably didn't have like the finance courses, the accounting courses tell me a little bit about just like the decision to even apply to these roles and what that whole recruiting process are like, do you have an internship? What was it like?
Calvin [00:05:56] Yeah, yeah. Of course, I would say I was a bit of a late bloomer. I when I joined college, I wanted to be an engineer and then after my first semester, take an engineering course, intro to engineering of all courses, I was like, All right, I'm not cut out for engineering. And then I decided to switch to environmental science and policy management did a semester that also did not feel like it really fit my personality, either. And it was kind of like a broad major, right? It's a combination of qualitative and quantitative. It's broadly applicable. It's a skill set that you can always leverage in a number of different kind of career paths. So I thought that always made sense. It's a little bit of finance, a little bit of macro, a little bit of qualitative thinking. But I had really no idea, to be honest. I think midway through college, I had no idea what I wanted to do. Luckily, there's a pretty, pretty vibrant business community within Berkeley, right? It's it's a large school and one that had a very big presence in terms of business. They had an undergraduate business administration program, and even a lot of people who weren't in that program were always thinking about business, particularly consulting, accounting, finance. So I met a lot of other folks, you know, a lot of my classmates were interested. They had a much more kind of guided opinion about where they want to do with their lives. So I feel like that kind of rubbed off on me, right? I had a chance to kind of learn from them like, OK, is your
Patrick (CEO of WSO): [00:07:21] Family not in finance?
Calvin [00:07:23] No, they're engineers, which is why I started my career and my my my college. Was it just
Patrick (CEO of WSO): [00:07:29] Crazy competition there?I assume it was like just brilliant people.
Calvin: [00:07:33] Oh yeah. Oh yeah. I mean, that's not just true for engineering. It's true for a lot of the majors at Berkeley, but in engineering. I'm like, I knew immediately. I'm not cut out for this relative to some of the people that were in my classes, right?
Patrick (CEO of WSO): [00:07:43] That's an intro one on one.
Calvin: [00:07:45] Yeah, exactly. Exactly.
Patrick (CEO of WSO): [00:07:48] These people are on another level. Yeah. Very good. So tell me a little bit about just once you kind of came around to, you're like, Oh, well, UConn's interesting. I enjoy the class a little bit more. Has that blend which kind of suits you well and then people are like, started telling you about investment banking? How did you hear about it and did you get that junior summer internship?
Calvin: [00:08:06] Yeah, yeah, so I think Junior is when I first started taking it pretty seriously, I felt like I had a pretty good grasp of what investment banking was. I mean, as much of a grasp as someone who's a college junior could have back then. Obviously, the Wall Street business forums was a great resource for that as well, because I'm like, Wow, there's a lot of people that talk about this.
Patrick (CEO of WSO): [00:08:25] I know you were a troll back then. I'm just kidding.
Calvin: [00:08:27] I was a troll, for sure. Kind of just quietly lurking in the background. But yeah, so a lot of a lot of my friends were going to recruit for consulting and banking, so we definitely pressed together cases together. We read all the different guys. You know, there's a Wall Street Oasis guide, of course, and then mergers and acquisitions kind of all the standard stuff. Yeah, I feel like back then it's a little bit easier. I feel like kids nowadays are probably doing internships before they're even going to college and, you know, during the spring and the fall. But back then it's, you know, you get a summer internship, ideally maybe an unpaid internship in your sophomore year, but then by junior year, you really seriously recruit, right? So I my junior year, I landed at a middle market firm called Stiefel, did a summer there. It was a great way to just like, really understand like, OK, this is actually what investment banking is, right? And I felt like I had a much better grasp of like, yeah, one, I can do this and to actually do want to do this as my first job out of college, right? It was kind of good soul searching and disturbing for myself. And then
Patrick (CEO of WSO): [00:09:31] Coming back from I was at SF yeah, asset base as well. And then was it tell me what the like was a recruiting process like? Were there like résumé drops on campus and then like, you get selected. So tell me about your like numbers. Was it like twenty banks? You dropped it. You got like 10 interviews, ten interviews and like two offers? Or how did how did it come out? Yeah. So roughly, I mean,
Calvin 00:09:51] Yeah, yeah. So, you know, Berkeley is a target school for a lot of banks, especially if you have an asset based officer, you're going to recruit a Berkeley, Stanford, UCLA, USC, typically on the West Coast. So, yeah, we had a we had a career center. You can apply online for different banks, you know, they all kind of pop up at the same time. There's probably, you know, there's obviously like the 10 or 15 names everybody knows, and there's kind of a longer tail of some little Marcus boutique banks there as well. I obviously dropped my resume everywhere because I know it's a numbers game. I probably dropped my resume at twenty different places, got four or five first round interviews, was fortunate to convert one. I was by no means like crushing it in my junior year.
Patrick (CEO of WSO): [00:10:33] Wait a second, you got out of the 20, you got four to five first round interviews. So that that means that engineering course might have actually hurt you because the GPA was not like a three to eight.
Calvin [00:10:40] Yeah, it is. I think that's right, especially within like the business community, people typically have three, seven, three eights.
Patrick (CEO of WSO): [00:10:46] That's right. So you have like a three going into this or
Calvin [00:10:50] You're pretty close. I was not I was not a stellar student.
Patrick (CEO of WSO): [00:10:54] I'm just seeing the conversion rate and I'm like, OK, that means that, you know, that means you're probably fighting an uphill battle, right? But yeah, it's good. You got those interviews and you were prepped it sounds like.
So tell me how you convert from the four or five first rounds.
Calvin [00:11:09] Yeah. So my GPA was not stellar. My I think my experience was also not light, but definitely not as stacked as some of my as my classmates. So I knew I had to be aggressive that I couldn't count on. The brackets are going to get back to me or these banks are doing back to me. I had to just apply everywhere and try really hard, right? I did a ton Of kind of interviews With my friends. We would prep each other. We would try to trade questions if we kind of got them from a certain bank, right? Like, OK, I just want to hear from Deutsche Bank or this way I hear from Citi.
Patrick (CEO of WSO): [00:11:44] Yeah, by the way, people can access the company data, but if you look at the company database, we have over, I think 5000 10000, which a little plug there. I think over ten thousand questions or more now. No, sorry, like 30000 questions yeah. For like invest in making interviews or in our database. So it's basically unlimited, but it's by company by position. Ton of summary analyst interview.
Calvin [00:12:05] Yeah, that's really helpful, man. I think, yeah, I was definitely like lurking in the forums too. And sometimes I I'll see some questions from certain banks like, Oh my god, I have no idea how to answer that right? And it's kind of back to the drawing board. How do you figure that out? But yeah, I mean, like, I didn't do anything special. I think just prep my answers. I knew there's going to be a series of 10 to 20 questions that I think 80 percent interviews are going to ask some combination of this, right? So really narrowing it down. I think the hardest part for me was like answering, OK, why this bank or like why investment banking and not giving a very generic answer, right? It's easy to say like why Goldman or why Morgan Stanley's like, OK, well, these are premium premium banks, right? It's easy. You say you can have the best deal experience. You work with the
Patrick (CEO of WSO): [00:12:47] Top people like why people and you. It's a little bit harder. It's a little bit harder yeah, yeah.
Calvin [00:12:53] I still think there's a good answer for that, right? I think there's a level of exposure and that you can get at some of these other banks. You can get a better deal experience. You can work with great people. So there's a lot of very talented people in the industry.
Patrick (CEO of WSO): [00:13:05] Sometimes you work directly with the VP and so like, there's no associate because they're really.
Calvin [00:13:09] Yeah, that's exactly exactly. But it's hard to know that coming in right? Like, yeah, it's just hard to know that. Cool. Ok, so you're doing all these interviews
Patrick (CEO of WSO): [00:13:18] You do for interviews, you end up with just the Stiefel offer or do you have another offer just as equal offer? Ok, so you're like, Yeah, I made it. I got something. Do you have that summer internship? And yeah, was that like, was it heavy hours like your typical summer analyst position? And then were you able to convert it, or did you have to go into senior year kind of with nothing?
Calvin [00:13:39] Yeah. So I had a really good summer experience. I was placed into kind of the telecom side of the team where network technology team, which is the strongest team there. They had a lot of activity and I was lucky to get placed there, I think and yeah, I mean, the hours are tough, but nothing out of the ordinary. I think typically six days a week occasionally get a Sunday off and then you work from nine to midnight, typically, sometimes a little bit early or sometimes a little bit later. Nothing that I wasn't worried about coming in. It wasn't like one hundred twenty hours for the entire summer, but it was a really good experience. I worked on a few projects and they were also, I think maybe just given the culture of the office know they were very internet friendly. They try to promote our growth, they try to kind of challenge us and get us excited about the work too. They had a little project into the summer project for each one of us that we could to present in front of some mds and beeps, which was fun. A little bit scary at first, but you know, they kind of cared about that, right? They want to make sure that people felt included, even the interns. So I did get a I did get a return offer. I did. I did really well in my summer, but I thought, you know, for me, I felt like I had enough of a grasp on the industry that I definitely, when I came back to school, wanted to test the markets a little bit more right. I've always very much believed in my abilities, and not that CFA wouldn't be a great place to launch my career, but I want to see what else was out there. So I came back for a full time recruiting.
Patrick (CEO of WSO): [00:15:04] Did they give you a an exploding offer or were you able to kind of shop it a little bit?
Calvin [00:15:09] It was not an exploding offer, but by the time recruiting kind of started a ramp up for other banks, it had expired. You had to let it go. I did have to let it
Patrick (CEO of WSO): [00:15:19] Go before you had anything else lined up.
Calvin [00:15:21] Goldman Man. Yeah, I'm typically not a risky person,
Patrick (CEO of WSO): [00:15:25] Especially coming out of the financial crisis. You know, we're only like three or three Years removed from like the depth of that. Yeah, I
Calvin Think I was just young and stupid. Probably to some extent.
Patrick (CEO of WSO): [00:15:35] I just you believed in yourself? Yeah. So tell me how that were things kind of looking up? Had you put your GPA up a little higher where you're getting more first rounds on the on the full time or where, like most of the slots
filled by interns and there wasn't much left?
Calvin [00:15:49] Yeah, I think full time recruiting is a bit of a different animal than junior summer recruiting, right? It's especially if you've already done it, a pretty significant junior year internship like that's validation for the market. Like intern at this bank, they gave me an offer. I got good reviews. The GPA becomes less of a factor at that point, right? Gpa four for most banks, it's just an indicator. If you don't know anything about a person that they had limited working experience, it's like, OK, that's a proxy for how maybe intelligent or hardworking someone is right. But by the time you've already validated yourself with work experience like real working experience, that becomes much smaller factor. So my GPA was a little bit better by starting my senior year. But still, like no ones going to like, be wowed by it, right? But I think it's really that internship that gave me kind of a leg up for full time recruiting. And I think full time recruiting is both harder and easier. In a way, it's easier in a way because a lot of people have already accepted. All time offers, right, coming back from their junior internships, so the pool of candidates are recruiting are going to be it's going to be a little bit less competitive, right?
Patrick (CEO of WSO): [00:16:52] There's less banks to write looking.
Calvin [00:16:53] There's also less spots. So that's what makes it harder. So you have to really stand out from the competition. ] So what do you think like in for like
Patrick (CEO of WSO): [00:17:01] Summer analysts recruiting, at least back then? Would you say they were pulling like 30 or 40 people in four analyst spots, like some random spots and then the full time senior year they're only looking for like five to 10 something like that?
Calvin [00:17:13] Yeah, I think whatever the number of spots are trying to hire for, probably multiply that by eight to 10. That's how many first round interviews you probably want to be doing. Yeah, yeah, it's interesting. So, yeah, so your
Patrick (CEO of WSO): [00:17:26] Hit rate on actual interviews, though for full time you had the you had good deal experience. You had a good summer. You had yeah. Were you smart enough to indicate on your resume that you had received an offer or did you think that would look cheesy?
Calvin [00:17:41] I think I I think I did. I actually didn't think it was cheesy because I think that's actually one of the most important things to have, right? That like I did a successful enough job that they wanted me back
Patrick (CEO of WSO): [00:17:53] Or something like that.
Calvin [00:17:53] Exactly, exactly. And you know, and that's going to be the first thing that they're going to ask you anyways in an interview, it's like, Well, did you get a return offer? And you have to be candid about that, right? There's no point in hiding that. So there's there's no harm in highlighting that fact, for sure.
Patrick (CEO of WSO): [00:18:08] Cool. Ok, so you managed to recruit and tell me about that whole process so again, you dropped at 20 places or to maybe just 10 this time because there wasn't as many? And what would it look like?
Calvin [00:18:19] Yeah. So I felt like I was in a decent enough spot. I didn't feel like I had to just get a job anywhere, because now that I've had some experience under me, I kind of know what I'm talking about. I can talk about specific project and deal experience. I have a better, more visibility into what I'm actually trying to get out of my full time job, right? So I think I probably dropped at 10 places at this time, more focused on the bulge brackets and a few different boutiques that I held in high regard. And yeah, the hit rate this time was much better. Like, I think I got at least the first round everywhere. I converted at least 50 percent of my first rounds into final round.
Patrick (CEO of WSO): [00:18:56] Nice. And then how many offers you end up one or two?
Calvin [00:19:00] Well, I just got one because I interviewed a Perella fairly early in that process. I got an offer on Friday, had a few more super days the following Monday, and they asked me to take the offer over the weekend. And you know, that's totally valid. Again, you don't want to lose out on candidates, right? So for me, I really like the team. I thought it was a good firm. I like to lean kind of nature and structure of it so great. Yeah, yeah. I thought, you know, be foolish not to say yes. Like, what am I optimizing for here? That's just a lot of risk for very little upside. So, yeah, I like the team a lot, so I decided to go with them.
Patrick (CEO of WSO): [00:19:37] Nice. And at this stage, so you're basically signing on the dotted line. They're paying you like a ten thousand dollars signing bonus or 15 or something like that. And then what, 75 base, 80 base at that point? I can't even
Calvin [00:19:48] Remember. Yeah. Yeah, it got a lot higher as I became a second year. I think the whole industry started something
Patrick (CEO of WSO): [00:19:53] Like 90 or something or 80.
Calvin [00:19:55] Yeah, yeah, yeah, something like ninety five for four years. But I was like, well, seventy five for first years when I first started was good. I thought I was like a little bit above market. But yeah, that's the high level of it.
Patrick (CEO of WSO): [00:20:05] Nice. And so you're there for a good two years doing M&A, you know, some strategic transaction stuff like that. And tell me a little bit about just how it evolved. Like, did you feel like that internship experience had prepped you well or was there like a heavy ramp up period because you were in Econ Major? You didn't have the finance and accounting background, like, was it really tough the first five or six months? For me, it was so I'm just curious for you what it was like.
Calvin [00:20:28] Yeah, I actually did take some finance and accounting courses at Berkeley. Yeah, I did.
Patrick (CEO of WSO): [00:20:33] We're more well-prepared. Yeah.
Calvin [00:20:35] Sometimes I feel like most of my oundation was built off the Wall Street. Always guys l like, how do you even get to what is EPA? How do you get free cash flow? All that stuff. I feel like I learned from the guys, from my friends. But yeah, I would say the part of me, well, I think not just of technicals, but also like the expectation that you have to be highly detail oriented, that you have to get things done right. You have to understand where your role within the team is right. So I think that all prepped me well. Obviously, you know, the first year of banking especially is a very kind of aggressive ramp up period. Like, there's no amount of that could prepare you for a full year of doing that right and not just as an intern, but is actually like a very, very critical full time member of the team. So that was obviously tough, but it's nothing unusual within an industry like it's more so a burden of like being able to manage different expectations, timelines, you know, just getting everything done rather than how big is
Patrick (CEO of WSO): [00:21:36] How big is the office out here?
Calvin [00:21:38] It was, I think, eight people when I joined. I think today it's like 30. It's like,
Patrick (CEO of WSO): [00:21:44] Wow, it was pretty small back then. Ok yeah, yeah.
Interesting is there. I think there is there. Boston office the main office, though. Boston, New York, New York is OK. Well, OK, so you're you're kind of going through your two years crazy, heavy ramp up its long hours, it’s tough as expected, but you're learning probably a ton. Mm hmm. That second year or when do you start kind of thinking, you know, I'm going to go private equity or, you know, at this stage, I remember 2013 is like, it was already accelerating. So you were probably already there were probably fellow analysts kind of talking about that. And what were your what was your thought process in terms of where you wanted to go next?
Calvin [00:22:20] Yeah, it definitely changed. When I first started thinking it was very much I had to do private equity. I actually didn't even know why myself. It just it seemed like a natural next step. That's your banker. And then you go. Exactly. I feel like I didn't truly start thinking for myself until a few years ago, but I just felt like the natural progression. And I definitely
Patrick (CEO of WSO): [00:22:41] This podcast is actually really the whole point of the episode podcast is to kind of highlight different paths. And so I think It's important to highlight your path because so many people are just like, I need to go Ibp, which is it's great. It's an amazing career. It's what I did. But there's like so many other ways to do well and be happy and stuff like that. So yeah, sorry, I continue. Just want to.
Calvin [00:23:02] Yeah, yeah, no. I think that's absolutely right. I mean, there's so many things you can do with that foundation, right? I think 10, 20 years ago, maybe he felt like about the only choice, but the best choice, right? But now there's just so many like especially within tech now it's a very vibrant kind of industry. There's just a lot of cool jobs you can do beyond just being a p p guy, right? But yeah, I mean, like at least I very much started with that mentality like I want to do. I talked to all the different headhunters. I interview a bunch of different shops and I was never really excited about it, right? I went through the processes. These like small offices with like 10 or 20 people. Everyone's in their own office. It's quiet, like you could hear a pin drop. And I was excited because I'm like, OK, this is a good opportunity, but I never felt personally excited by it, right? So I think kind of towards the end of my first year, especially beginning my second year of banking, I started thinking, like, what about corporate? Like, I think there's a lot of cool corporate jobs out there, a lot of cool tech companies. I had friends who had transitioned from banking to tech in like finance or corp dev type roles. I would visit them sometimes during like their companies. Happy hour. And that's a thing like this. Happy hours are pretty common within tech prior to COVID. And I would just go, I'm like in my banking outfit, buttoned up shirt with my like banker bag and I would go and everyone's wearing t shirts. And you know, there’s people riding scooters around the office and there's, you know, whiskey and beer flowing everywhere. I'm like, Oh my God, like, what is this world? This felt crazy to me. Like, why would anybody do private equity or whatever when you can have such a vibrant, happy kind of atmosphere, right? So I think at that point, I started thinking about it more seriously. Like, like, have you really fun to work at like a twenty three thousand person company, you know, building really cool pieces of technology that everyone uses and not have to work 80 to 90 hour weeks? And yeah, yes, I started interviewing a lot of different tech companies. And I think for
Patrick (CEO of WSO): [00:25:00] Me, before we jump there, let's talk a little bit about the stuff that you did go through some processes. Did you did you make it to like final rounds on any of them to like what was it like any firm? Do you remember specifically, it was all West Coast like you wanted to stay here, right?
Calvin: [00:25:15] Yeah, mostly West Coast.
Patrick (CEO of WSO): [00:25:16] I did any growth, equity, any growth, equity shops and stuff.
Calvin: [00:25:20] Yeah, I mostly just be a couple of growth like iconic and then but mostly like middle market shops. I felt like maybe I didn't quite have the pedigree to go, you know? To the mega shops, right, like I I don't know, because again, I'm like, I I wasn't that even had that much conviction that I wanted to be, so I thought, OK, maybe I'll test the water a little bit with the middle market shots. I had a number of final rounds. I didn't necessarily close any of them, and I think I probably would have joined if I did, right? I think I'd probably been like, OK, well, this is what I'm supposed to do. I should just have to do. Yeah, exactly. I think looking back now, I would have gone probably harder into your growth equity. I think that is a type of investment structure and product that probably fits my skill set and my personality the best. So if I had to do it again, I probably look at the top growth stocks a little bit more actively. Mlp itself probably wasn't nearly as interesting to me. Probably. Look, take a deeper look at that corner of the world. What about VC? I am I think it depends. You see, there's a broad spectrum, depending on stage and focus. I don't see myself as a very early stage person. I think again, it's about your own aptitude and about what type of work you like working on. I like doing financial work. I like doing true due diligence. It's not about I met these founders and I feel like. They could be a great. This could be the next Zuckerberg or the next CEO, I must, but it's I like actually working with numbers and understanding with the story that the numbers are trying to tell, right? And I think our growth, especially there's a level of just like opportunity ahead for these companies that's exciting. By the same time, it's still grounded in technical analysis, which I think would fit the type of work I enjoy doing the most. I think kind of the financial engineering aspect of private equity probably was never that appealing to me, you know, acquiring assets that,
Patrick (CEO of WSO): [00:27:16] You know, off cash flow, levering up the debt.
Calvin: [00:27:18] Right, exactly like large auto dealerships, you know, and the three actually made over five years. That's not really appealing to me. I'd rather bet on the next Snapchat or Twitter or Facebook, right? I think that to me, was much more thrilling.
Patrick (CEO of WSO): [00:27:32] Ok, so you're kind of coming up through your second year, you get some you get pretty far and some key middle market shops doesn't convert. Do you feel like the headhunters were giving you looks, though? They're still giving you chances because you're making the final rounds? Or were or
did you feel like that lack of conviction was hurting you?
Calvin: [00:27:49] Yeah, I'm still getting looks. I was still converting pretty well on first rounds, I thought, I'm
Patrick (CEO of WSO): [00:27:56] Saying, if you're doing that, they're beating you because they know you're a place.
Calvin: [00:28:00] Yeah, like I wouldn't embarrass them right in front of a client.
That's a big Deal. It's like, why did you send me this guy? Like, No, I wasn't. I hopefully was not in that tier.
Patrick (CEO of WSO): [00:28:10] Yeah, that's fair. Ok, so but this is now kind of coming into year two at that Perella and you're at the stage where you've done a bunch of processes and you're thinking, OK, what else is there? You're having a good time at all these happy hours and so how did you go? How did you go about thinking of like, OK, Twitter is the right fit for me or like, how do you even know? Because like, there's so much, especially in the Bay Area, there's so many of these like why not Facebook? Why not Google? Why not Dropbox initially, like, you know, you know what I mean? Yeah, yeah. About how you thought about that because it's I think that's a tough decision, right? Not knowing what the internal you see all the happy hours stuff, but like, you guys still have to work some, right? There's like, you know, what is it really like? You know, what's the culture really like? So can you tell me a little bit about that and how you went about it?
Calvin [00:28:57] Yeah, I would say it is hard because I'm not going to say like five this homogenous, it's not by any means your experience affirmed affirmative firm will differ, but the high level they all operate in a very similar manner. But a tech company is very different. They're just very, very different stages, very, very different types of industries. But then technology and even at similar companies within tech, you've got to look outwardly the same. But the corp dev teams might have a very different mandate, a very different approach to how they think about M&A and strategy and finance, right? So honestly, a lot of it you don't really know until you're in the interview process and you are able to test the other side about how they operate as a team and how they think about the strategy for the company. The other good thing. The other resources. You know, I was lucky. You know, I went to Berkeley. A ton of my classmates and friends were in the Bay Area. A lot of them went into tech, right? So I had a chance to speak with a lot of them, like, Hey, what was your experience at Dropbox? What's your experience like Engineers or engineers? You know, finance, Business operations, Products? Kind of a very broad spectrum. But yeah, like different thoughts. Like what is it like working at this company? Like, what do you like about it? What do you what you like about it? What would you not expect at the end of the day? I think you just have to kind of go through the process yourself. A lot of times, you know, you get to speak with the recruiter and get a sense for what the team is looking for and then think to yourself, like, what is your criteria like? Why do you want to jump to tech? Like what types of tech companies are interested in you? What type of work do I want to be doing at that company, right? Am I trying to just grind out deals? You're trying to grind out deals and yeah, actually join like a Salesforce or Oracle or Cisco that do 20 deals a year. Do you like being a part of like a scrappy early stage team? Then maybe you should be looking at a Series C Company Series D company that's looking for their first or second finance hire, right? So I kind of found myself somewhere in the middle like a
Patrick (CEO of WSO): [00:30:50] Company that Twitter was kind of in the middle where they weren't raising like a bunch of money anymore, right?
Calvin [00:30:55] Or, yeah, they had just gone public.
Patrick (CEO of WSO): [00:30:57] They just gone public. Ok, so like that, that was it. They weren't like doing any more series, whatever f you know, at that stage. Was it profitable at that point or no?
Calvin [00:31:09] Or close approaching? Yeah, approaching it.
Patrick (CEO of WSO): [00:31:12] And so at that point, though, like how big was the the M&A team within Twitter or, you know, proxy and getting the exact numbers. But just like, is it like five people? Is it like 30? Like, I have no idea, you know what I mean? So yeah, yeah. And then how were you thinking of that? And like your place in it, like coming out of investment banking analyst stint? Like where were they? Where do they place you in the whole hierarchy of that group? Yeah. The team was about
Calvin: [00:31:38] Eight to 10 across the entire kind of spectrum of M&A, right from strategy to sourcing execution and aviation. I, you know, as a second year banking analyst, I came in kind of at the very junior level. Most of the people that they were creating, like Corp Dev teams, will never recruit someone out of college. I'm not saying it would never happen, but it's. They're looking for people who are coming from banking or coming from other core dev teams like people who understand how these things work, who have the M&A skill set, right? So I came in at the very most junior level. My responsibility is primarily were for financial modeling and due diligence stuff that I was obviously very good at and worked with more senior team members who are more in
charge of the negotiation process, a sourcing process defining the strategy. And yeah, so working kind of hand-in-hand with them around that.
Patrick (CEO of WSO): [00:32:28] Yeah, you're still kind of like almost jumping. It's like a buy side role, though, right? So you still it's a little bit different because whereas in banking, you were yeah, you were helping manage the process, like in when you're in-house, you're now like responsible for like actually looking at it as. Is it actually a good investment or not and not trying to sell it right? So tell me how that what was that transition like they didn't care about like if your PowerPoint was perfectly aligned or the comma was in a certain thing, but they cared more about like the numbers being right. So tell me, was it was that like a big transition? Like, were your bosses like, did they also come from a banking background or were they from somewhere else? And they just wanted to know, like, I guess, how did they measure you?
Calvin [00:33:07] Yeah, yeah. Yeah. So 90 percent of that people probably have some banking background. Yeah, I think it's starting to become more diversified in certain cases. Having a technical background, it's actually useful for evaluation of new products and technologies. But for the most part, you're going to see a lot of bankers and yeah,
I would say the work itself is similar at a high level, but also very different. You're absolutely right. Like it's in banking, you're trying to pitch deals. Your goal is just to get a deal done and get a big fee for it, right? So you're going to pitch big ideas. Most of them probably don't make sense. You just want to get it done right because you're not measuring success based off of what the accretion really would be for the company where the strategic value you're going to measure it based off of. What can I put on a tombstone? How much fees am I going to get from it? I know that's not how all bankers think, but at high level it is the strategy of the business.
Patrick (CEO of WSO): [00:34:01] They're in sales. Exactly Yeah.
Calvin: [00:34:03] But the difference is and this might be even within Corp Dev and company, I think it's even more different than even the buy side, right? Because in the buy side, you have to make smart sound investment decisions. So your ultimate goal is just pure financial value accretion, but there might be different criteria and different strategies within a corporate environment. There might be types of deals that you do that you can measure purely on an IRR basis, right?
Patrick (CEO of WSO): [00:34:29] Like strategic, like competitive reason. Like, even
though that's the deal financially is not a great deal, it actually helps you corner a market or something like that.
Calvin: [00:34:39] Exactly. Exactly that. Or even like more tactical, like,
Patrick (CEO of WSO): [00:34:43] Hey, like how Facebook goes like they should antitrust issues when they acquire Instagram, WhatsApp, where it's like really smart. If they get away, if they can do it right, but like, then there's concern, right?
Calvin: [00:34:56] So right, right? Like it's it like WhatsApp, right? They bought that for 20 billion dollars of growth investor ever invested that 20 billion? No, they would never. Maybe, maybe today. I think everyone could get a 20 billion valuation today. But no, they would not have done that right. But even like practically like, we need a specific type of engineering talent that has this background and this area machine learning like we need acquire into it because it's impossible to hire at that or we need a specific piece of technology that would accelerate a particular roadmap by three to six months or six or 12 months, right? Stuff that's like very difficult to measure from a financial model, but you know how strategic value. So that's like the difference in thinking, right? There's a lot of different types of deals you can do in a corporate environment that have a lot of different types of impact, and you have to be able to think about how do you approach that deal? Like, how do we think about ROI justification? How do we think about integration? It's going to be very, very different for a lot of different types of deals. It's not always about buying a smaller business and thinking about the revenue multiple that multiple like it's it's
Patrick (CEO of WSO): [00:36:03] Multiple, like we're going to buy it at five x and sell it at 10X. Exactly. Yeah. Not all about that. There is some of that, I'm sure, because obviously the multiples that whatever Twitter is trading at or Facebook trading are especially now insane. But let's come down a little bit but I one sec. So I guess. What was the thought process in terms of like or what was your trajectory there and then why? Why move to another corp dev? Why not move up within their why jump to to a Dropbox? Is it more like wanted a change of scenery? What was the what was the rationale and when did you kind of start looking and what was that process like? Yeah.
Calvin: [00:36:47] I think for me. I I think kind of a recurring theme I square is that I wanted to do more right. I think after a couple of years at Twitter, maybe like a year and a half into the job, I mean, it's a pretty big team. I thought we had maybe a pretty. Large team for maybe the amount of M&A activity that we're contemplating, it felt like maybe I wouldn't get as much exposure as I would are to join a leaner team. Right. And I think for me, one Dropbox has always been very high on my list of companies that I kind of respected and held in high regard.
Patrick (CEO of WSO): [00:37:23] And do you ever look at going to Dropbox before? Had you been in the process with them before?
Calvin: [00:37:28] I think I did interview with them when I was in banking for a non corp dev role, but that was like a long, long time ago, OK? But yeah, but that's like, that's like one of the companies where, you know, I went to their office and I was just blown away by the kind of environment they're right. And a lot of my friends always talked very fondly about their time at Dropbox as well. Again, it's a lot of it is just about who your network is, work somewhere and what do they think about that business and where it's heading, right? So.
Patrick (CEO of WSO): [00:37:52] So like at Twitter, it was a pretty still pretty small team, but it was just more like the the pace and the amount of deals that were coming through wasn't at somewhere where you felt like, OK, if I stay here like. There's there's no real path up, I'm either at this position and go to business school. Do I really want to go to business school? I assume you thought of like mba like maybe that's. Tell me about that whole thought process, like, oh man, I don't want to go to spend three hundred thousand dollars on an MBA.
Calvin: [00:38:18] Yeah, it's funny because I was actually debating between going to Dropbox and going to business school. I had been accepted at a business school. I was considering going to Kellogg at Northwestern, but then I was thinking like, Oh my God, like, where am I going to business school for? Like, I kind of know what I want to do like, I mean, I'm surely it would have been a great experience, but does the opportunity cost really make sense here? So I started panicking, actually about having to go to business school around April. I'm like, Oh my God, I guess I have to go in two months. And then I got reached out to actually by a headhunter, which is actually very rare. Most tech companies do not use headhunters to source roles, even for things like Corp Dev.
So they reached out to me. It's a headhunting firm that I had worked with before, and they said, Look, Dropbox is looking for their second caught fire. And at that time, Twitter, especially like the company, wasn't super acquisitive at the time. They're going through some restructuring. We had a pretty large corp dev team, so I thought, you know, this is actually what I'm looking for. Like more responsibility, a leaner team at a company that I really, really liked and admired, and I think it would be a great kind of growth opportunity for me there. How did you get
Patrick (CEO of WSO): [00:39:26] Comfortable that they were going to be acquisitive enough even as number two? You know, their?
Calvin: [00:39:32] Yeah, I think one, just the fact that they had two people meant, like even if they had 50 percent of the volume that Twitter had, that would be seen. You're still doing more work right there. Yeah, and especially at that time, Dropbox was like in a really strong position, like growing really quickly, had a very lucrative and profitable business from a cash flow perspective, was probably going to go public soon and was a brand that people knew in tech, right?
Patrick (CEO of WSO): [00:40:00] So has is there ever a business, a tech business like? That is profitable before they go. I mean, I know Facebook was because they waited so long and stuff like that. But the majority of them are losing money, right? When they go public and they're like, Yeah, revenue is like this, but their earnings are like this. Yeah, tell me about that. Like, you know, was there ever like some sort of unicorn out there? It was. It was Dropbox closer to it where like, you saw really crazy growth, but like, it wasn't. So I mean, I don't know. Probably wasn't. They're probably dumping so much into growth but tell me a little bit how you think about that as like somebody who comes from a banking background, maybe a little more conservative and maybe not that the company's not making any money.
Calvin: [00:40:42] Yeah, I didn't like the asset bubble for so long. I always kind of wonder, like, how did people outside of technology perceive what we're doing here, right? It's like, Oh, these this company is like worth 40 billion dollars. They're not nearly close to profitable
Patrick (CEO of WSO): [00:40:56] Or losing two hundred million a year.
Calvin: [00:40:57] Yeah, exactly right. Could even be billions, right? Like, I always wondered about that, and I think you just have to have a different mindset. It's really about you have to look very far out, right? What is the potential of this company in five or 10 years, right? And can they capture outsized market share? Can they actually leverage technology to do that? And if they can, then what is it true earnings potential of that company, right? It's probably huge if you kind of pick the right company for me. Dropbox wasn't that risky. They had already kind of built a very powerful business model, right? Very efficient with it. Sas did not lean on sales and marketing for growth as much as their peers.
Patrick (CEO of WSO): [00:41:32] The Amazon Referral Network, I've heard, I've read about that.
Calvin: [00:41:36] Exactly, exactly.
Patrick (CEO of WSO): [00:41:38] You get more space if you invite your friend like, really smart.
Calvin: [00:41:42] Yeah, yeah, brilliant. I mean, they had more users than pretty much every social network outside of Facebook, right? Which is crazy and the SAS world, it's very much like a consumer business within kind of a SAS ecosystem, which is what's appealing. So yeah, so I didn't think it was a risky move at all, and it was going to be a step up for me in terms of responsibility. I thought it made a lot of sense that makes a ton of sense.
Patrick (CEO of WSO): [00:42:10] Yeah, I mean, yeah, it makes sense. Tell me a little bit about how you think about joining a tech company like this, like pre IPO was Twitter pre IPO before you went and was that like a big carrot where they're like, Hey, we're going to give you options and we're going public in a year? Like, How do they communicate that to you and how should you? How much value should you give that? Because I've had friends out here who was like working at some large, large firms and they're like, Yeah, we're gonna go public and it’s like three years later, right? Yeah. Tell me how you should discount those options and think about that a little bit. Yeah.
Calvin: [00:42:44] So I mean, I joined. Twitter right after IPO and I joined Dropbox right before IPO, so very much like it was kind of a sure thing, like nothing's a sure thing, but it was as close to a sure thing as you can have. So I wasn't going to get crazy upside.
Patrick (CEO of WSO): [00:42:58] Wework showed nothing to sure thing.
Calvin: [00:43:00] Yeah, that's true. That's true. That's fair. Yeah. There's always going to be work out there. Yeah. But for me, like it wasn't a gamble really like it was. I was not given a package. I was going to have 10x upside, but it was also going to have very minimal downside, right? So I didn't have to overthink that too much. It was pretty much equivalent to an offer package if I were joining a public company obviously, a little bit more upside, maybe a little bit more risk, but I kind of within those bounds, but it's more difficult. Like the more can we talk to can we talk about
Patrick (CEO of WSO): [00:43:31] Pay just kind of going through? So you're probably making like, what, one 30 your first year out of school at Parilla? Yeah, I don't know. 150, maybe. I don't know they pay pretty well, I think, but maybe a little bit more. One fifty one sixty max and then second year, I assume they didn't dock. You did you tell him you were leaving before to Twitter before you got your bonus? Or was I going to say, Yeah? Yeah, I I did.
Calvin: [00:43:54] I did let them know. I told them, like in April, and bonuses came in June, but I had a good relationship with them. Like, like, OK, well, you. This is the earliest date you can leave and still get your kind of full bonus Yeah. And I essentially quit that day and started the week after that.
Patrick (CEO of WSO): [00:44:09] Twitter I have a break, unfortunately, but OK. So now and then. Tell me about like pay going to M&A because oftentimes it can be a pretty big pay cut, right? Going from like the finance world to in-house. Was it a big like? I assume the base was similar, like around one hundred, but was bonus, like gone and it was just all in options at this point. Or was it like? How should how should we think about that and you can give a range it doesn't to be like, this is what I got paid.
Calvin: [00:44:35] Yeah, yeah, of course. So you're right. I think salary typically within corporate and banking, especially at the more junior levels, are going to be pretty comparable. Right. So if you're two years out of banking, you're probably looking at one hundred, maybe upwards of 120 base there. Some companies have a cash bonus program. It's never going to be like anything near what a banking bonus would be. Maybe 10 to 15 percent of your salary would be an annual bonus and contingent on performance. And then the last component would be stock right than the way to do it is. It's a four year grant. You get the full first year grant after your first year and then every quarter after that, you vest another one 16. Right. So yeah, so I mean, again, how much?
Patrick (CEO of WSO): [00:45:23] How much? Yeah. Like, how do you even value that? I mean, I know they give you a strike price
Calvin: [00:45:28] Or something. Yeah, those options
Patrick (CEO of WSO): [00:45:30] Like how do I?
Calvin: [00:45:31] Yeah. So public companies and even companies that are approaching public would typically not grant stock options anymore. It would be reduced. So it's like a stock option, but with a zero dollar strike price. So it's essentially just a share, right? Yeah. So you can you can you can value that at face value. Like, it's pretty. It's pretty straightforward. It's like we're going to give you a thousand shares a year at today's value that might be twenty or forty thousand a year. Obviously, there's opportunity during the four year vesting schedule for your stock price to appreciate. Obviously, there's potential decreases and downside so you have to make your own judgment call. You have to understand what is it worth today and what do I think the company could go in the next few years, right? This be a company that could 5x.
Patrick (CEO of WSO): [00:46:15] Yeah, yeah, yeah. So obviously, yeah, there's more variability up and down there, but you can think of it as like you're still getting a pretty good base. And the stock grant two years after banking isn't going to be at least on day one. It's not going to be as it's not going to be like $100000 face value right that day. It's going to be probably closer to two hundred twenty to fifty thousand ish in terms of. But like with the potential to double or triple and then become that interesting. Ok. So you say that's pretty typical for that type of role, kind of a junior corporate Bank Corp dev
Calvin: [00:46:47] Role coming out? Yeah, I would say so. A couple of years out of banking, you're not going to be like, it's a taker. Yeah, it's
Patrick (CEO of WSO): [00:46:56] A pickup, but it's not a massive pay cut. It's not.
Calvin [00:46:58] It's not. Yeah, I guess the comparison would be like, compare to your second. You're a banking analyst. Yeah, maybe like a slight pay cut, but then compared to, Hey, I'm going to make associate next year, then that's going to be a bigger pay cut, right? That's really the consideration you should be weighing against. Like, what about our interest?
Patrick (CEO of WSO): [00:47:14] What about hourly rates? Oh, you're
Calvin: [00:47:15] Crushing your question.
Patrick (CEO of WSO): [00:47:17] It's a pay raise. Oh yeah, you're crushing
Calvin: [00:47:19] It for sure, depending on what bank you went to work that
Patrick (CEO of WSO): [00:47:23] Making 20 percent more per hour, but you're uh, 20
percent less
Calvin: [00:47:28] And unlimited vacation days, man. Like, it's there's a lot of perks for sure.
Patrick (CEO of WSO): [00:47:33] Yeah. Does anybody take that? Like when more than two.
Calvin: [00:47:38] Studies have shown that companies that offer unlimited voice take less right, they'll take less. Yeah.
Patrick (CEO of WSO): [00:47:45] Maybe I should do that. Yeah, no. So like, we're OK. So we're here. You're here at Dropbox. It's great that you've wanted to be here. It's fast growing it's exciting and this is pre IPO.
Calvin: [00:47:57] Yeah, about a year before they went public or about nine months.Tell me what it's like being in the corp
Patrick (CEO of WSO): [00:48:03] Dev team of a pre-IPO company. Was it exciting or is it whatever it is, is taking care of us? Somebody else is dealing with this? Did they have you deal with the bankers at all or were there? Was it reckless? Or was it no bankers? I was not a part
Calvin: [00:48:16] Of the IPO process. That was another team that did that. Yeah, pre IPO actually like Dropbox was pretty acquisitive, pre IPO. That's one of the things that gave me conviction. Like, I want to go here like they had done a ton of deals for like a three or four years prior. A lot of them are small, like, not like huge transformative deals like that. Like they were
Patrick (CEO of WSO): [00:48:35] Paying. One hundred million like that tend to
Calvin: [00:48:36] I don't know the exact figures, but yeah, nothing big. It would be like the companies that they were acquiring were probably like five people to like 30 people. So it's not like a gigantic company acquisitions. They're just like a high velocity, smaller deal type environment. And I think what they wanted to do with my hire and the director did that they brought in before me was like, OK, let's start thinking larger, right? It's great to hire like small teams or acquire small teams and acquire small companies. But what is really going to move the needle here, and that's going to be an evolution of like how every company is going to be like pre IPO. You probably don't really need a person that much until you reach a certain stage, but then you might be focusing all your time on talent based acquisitions or small technology acquisitions. And then once you start raising bigger rounds and once you're the value of your private stock is like approximately the value of your public stock. When people actually value that as a currency, you can start looking more strategically a larger deals, right? Like actually acquiring new businesses, new revenue streams very much before. It's much more tactical about filling up talent gaps or technology gaps, which will still be a part of the focus. But you're going to be able to do more and do bigger, more later stage. You are.
Patrick (CEO of WSO): [00:49:51] Great, so like, yeah, you're with them through the IPO and then yeah. Tell me a little bit about you’re your it sounds like it's like I'm looking at your LinkedIn, it's like two years to your future. It's very like, So is there a two year thing here where it's like it's time to move? After a year and a half, you start thinking, OK, what's my next stage are like, I know it's very normal.
Calvin: [00:50:12] Yeah, it's funny because for my first three jobs, I pretty much stayed at every single one of them two years to the dot, like exactly twenty four months. That was not intentional. It just kind of happened to work out that way. And that's not really like the approach I'm taking to my career. Like, I'm not going to just stop somewhere for two years. It's not like a private equity line to your standard. And I got kicked out or anything, but it just kind of happened that way but but yeah, yeah, Dropbox is great. Like, it's a company that had gone through a lot of change. In the two years that I was there, we my team had done kind of the first big deal that they had done. Like an actual new business business line. We acquired a company called Hellerstein, which is a DocuSign competitor, OK, kind of in twenty nineteen or early parts of twenty nineteen, which is which is great. It was a really fun deal process. It's always really fun helping a company do its first kind of like big deal because a lot of folks within the company, they don't really know what to expect, right? And it's kind of fun going through that process for the first time. It might be a little bit more difficult, but it's a huge, fresh challenge.
Patrick (CEO of WSO): [00:51:20] Interesting. I was just looking at up to Dropbox stock, so you're just out of curiosity and yeah, you haven't missed much upside.
Calvin: [00:51:31] Put it that way. No, I have not. I would say I didn't quite strike out my first two companies, but I definitely did not do party like I'm not questioning from the stock.
Patrick (CEO of WSO): [00:51:42] So, I mean, Twitter was such a big name to you. I mean, it's almost impossible for it not to be overvalued because it's such a especially consumer wise. I feel like these stocks. Well, Twitter's now done well recently, but for a long time it languished.
Calvin: [00:51:55] Yeah, I was part of that languishing. I think I was there for the two years where they were languishing the most. I think it's one point I was at like fourteen bucks a share, and when I joined it was that it was 50, so I had my share price cut by almost three quarters, right? But it is what it is. You know, it's that's a variability that you have in tech, right? You can join a zoom that grows one hundred x and like a year and a half, and sometimes you'll train. We work that goes the opposite direction and within a year as well. That's kind of the fun and the challenge of working in this industry.
Patrick (CEO of WSO): [00:52:32] It's really interesting. So, yeah, so yeah, in terms of the year, I know you didn't plan it out for two year to year to year, like you said. But when did you was the team bigger by the time you left Dropbox? Was it like four or five people then at Corp Dev and. That's true just to steal. Ok, so it was more like, Hey, I'm looking for a new challenge, that type of thing. It had been public for a while and you were like, Hey, I want to go earlier stage. Was that thought?
Calvin: [00:52:55] Yeah. New challenge, earlier stage. I think also I was looking for like a more diverse role. I think I draw Box Corp. Dev was very much a person. It's yeah. Yeah, exactly right. You meet some companies, you execute deals and that's fine. But we weren't also like an M&A machine. We weren't doing like six or seven deals a year that would really occupy you. Just focusing on that one specific role. I wanted to kind of expand my skill sets a little bit like, I like doing Corp. I like doing M&A. But is there other types of projects I can work on? Can I do fundraising for the company? I do. Yeah, yeah.
Patrick (CEO of WSO): [00:53:35] Tell me about strategy a little bit and like, what?
What that's like is it? Does that just mean you're like with the CEO at certain meetings and you're discussing like. I don't know. Tell me what that means at a fast growing startup.
Calvin: [00:53:48] Yeah, I would say strategy is a very nebulous kind of title. It could take on a lot of different forms at different companies and even within a company, there's going to be different strategy teams who are focused on different things, right? So I think at a high level, there's kind of two different elements of strategy, like a tech companies. When you hear like this Opt-In strategy or strategies, usually you are helping kind of implement a process or execute on like a project, like you're helping get a product to market or you're helping improve internal processes. Yeah, exactly. Like you're helping a product team and engineering team to pushing things along. You're like trying to drive initiatives. That's to me more of an operational type of strategy. And then there's kind of more corporate level strategy like zooming out, thinking very macro level,
like what does the vision, what is the vision of the company like? What is our place
within this industry? What do we need to look like in three years to be an industry leader? How should we plan against that? How should we think about our company
kind of structure and narrative? And how do we engage investors and be able to relay that story to them and in a very productive manner? Right. So that's more of the role that I'm taking on in my current role, which is kind of more macro focus, more industry.
Patrick (CEO of WSO): [00:55:04] It's a little investor, it's a little investor relations.
Calvin: [00:55:07] Yeah, it can be. Yeah, it can be.
Patrick (CEO of WSO): [00:55:09] Because you're, well, he's for fundraising, right? For on that side, I guess it's not really er in the sense of like your public or anything like that. So, so yeah, how how did you get comfortable? I guess we don't have to talk about that. I guess just in terms of. You've shared you've been really forthcoming sharing all your entire path, which is really impressive, I just is there anything Kind of looking back?
Any final words of wisdom? Looking back at your whole run, I know you've had a couple like you've been at some great companies in the transition from private to public didn't make you able to retire at 20 or I don't know how old you are like super young, but it's probably been. It's been a great career so far for you. So tell me a little bit about just what you'd suggest to people who might be interested in following in your path.
Calvin: [00:55:57] Yeah, I would say these are roles that really like you can make what you want out of it. There's just so much opportunity to learn, right? Don't think of the
corporate development position. As I'm an M&A guy, I'm going to make financial models and I execute, execute deals to be really, really good at your job. You have to spend a lot of time with folks within the company. You have to spend time understanding the product, understanding the technical architecture, understanding what is our go to market strategy or marketing hooks, even understanding things like you're working with HR and people team and figuring out how compensation or structuring and stuff like that and like benefits work, right? So it's an opportunity for you to absorb a lot from all aspects of the business and so you should go into it like very wide eyed, very receptive.
Just be a sponge, right? And to be good at your job. It's not to just be good at finance, you have to be good at everything. And I would have encouraged my earlier self to do that right. I thought, OK, I'm going to come in. I know how model I can kick ass. That's not enough to do the job well, and it's not enough for you to continue to rise in your career and especially in the corporate world is very much kind of like you can rise up as quickly as you can as you want if you're good enough. There's really no ceiling to how high and how quickly you can go. There's, I think, probably I think, for example, is hyper structured. Banking is hyper structured. I think in VCs, you see people who are twenty eight twenty nine make partner. That's possible in tech, too, like if you're super, super good and you can buy credibility because you are able to provide value for the company. There's no ceiling, right? So just be aggressive, be earnest. What would that
Patrick (CEO of WSO): [00:57:34] Look that look like for you? Like CFO role at a fast growing company? Like what is that? What's the standard like from Corp Dev? Don't, don't a lot of them go CFO eventually?
Calvin: [00:57:44] Or now. Yeah, I think like most everyone is doing your best. Some people do like chief strategy roles or CFO roles. I think if you're a CFO, probably more of a strategy oriented CFO rather than being a technical accounting, finance based CFO. Not that. Not that people don't have that foundation, but there's a different type of archetype, right, for different types of CFOs. But yeah, I think I think Cfos are a possibility or but most people just end up being like a VP of Corp Dev or Corp. Typekit. Got it
Patrick (CEO of WSO): [00:58:18] Fair. Well, listen, Calvin, thanks so much for taking the time and sharing your story with all the all the monkeys.
Calvin: [00:58:24] Thanks for having me, Patrick.
Patrick (CEO of WSO): [00:58:25] This is fun 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.
or Want to Sign up with your social account?