Lessons From Working In Pe Hedge Funds And Vc

TITLE: Lessons From Working in PE, Hedge Funds, AND VC CHANNEL: rareliquid DATE: 2026-06-02 ---TRANSCRIPT--- Hey everyone and welcome to the Rare Liquid podcast. Today’s guest is Kevin Jen who has an insanely stacked finance resume. He started off at Goldman in banking, then went to Apollo for private equity, was on the founding team of SoftBank’s 100 billion vision fund, worked as a hedge fund investor at Soros, and now is the founder and CEO of Mangusta, a venture capital and growth equity firm. All of this before the age of 35. Now, most people aim to work in one of the byside industries, but Kevin has literally worked in them all. So, I felt like I could have interviewed him five times and still not run out of things to talk about. In this episode, we cover a wide range of topics, including what it’s like to start a VC firm, stories about SoftBank’s founder, Masa, how he implements lessons from his hedge fund days as a VC investor, and a whole lot more. Now, before getting started, if you’re listening to this episode because you’re interested in breaking into private equity, you may want to check out the PE investing certificate program being offered by Wall Street Prep and Wharton. This program is sponsored by top firms like Blackstone, Carlile, and KKR. And over eight weeks, you can learn at your own pace through this online course that’s taught by Wharton professors, Wall Street Prep’s PE program director, and real PE investors, including David Rubenstein, the founder of Carell, and Martin Brand, the head of North America PE at Blackstone, who will cover topics like the PE deal process, valuation, how to think like a private equity professional, and more. By completing the program, you also unlock access to the alumni member database, buyersside chats with PE investors, and exclusive networking events with the world’s top private equity recruiters. This program runs three times a year and be sure to use my code Rare Liquid to get up to $500 off and I’ll leave information for everything discussed in this video’s description. All right. Hey Kevin, thanks so much for joining. And first thing I wanted to just ask is if you could walk everyone through your background.

Sure, happy to. Um, I’ll keep it quick and then we can dive into all the different elements uh over the course of this. Um, so I’m originally from Silicon Valley, uh, Chinese American, uh, grew up in a town called Certino, which a lot of people may know as like the birthplace of Apple. And, um, studied on the East Coast. So, I went to school at Harvard and then I’ve been working in I started out in more traditional finance, uh, and in particular, Goldman investment banking, and then I joined a private equity firm called Apollo. um after that and then for most of my career I was at SoftBank as one of the early team members at the vision fund. So I joined in 2017 and I was there until about 2 years ago where um I started my own VC fund called Mongusta Capital and Mongusta means mongus in Italian. Um it’s very interesting backstory on how the name came to be. Um but we are an early stage uh AI focused VC fund. We invest primarily at kind of series A and series B um based here in Silicon Valley which is where I live now in SF. Um and we invest across all kind of layers of the AI value chain everything from applications all the way to infrastructure uh and hardware as well. So been doing that for about 2 years. Um we started our first fund in 2024 and going to start gearing up for a potential new fund uh probably in the next 6 to 12 months. So really excited to be here and thank you so much for having me on the podcast. Um you know have always been a admirer of the work that you put in and the content um and that you that you do. So finally excited to be on here. Yeah, thanks Kevin. I appreciate that. And I think everyone who’s listening today will have a lot to learn from because, you know, as you’ve probably seen from my channel, I cover like banking, private equity, hedge funds, venture capital to some degree. And it’s rare to have a guest who has dabbled in all of these industries. Um, but before we get to any of the professional stuff, I actually had watched some of your other interviews and one story you talk about and something I want to kind of get into before we go into any of like the professional stuff is just kind of how your your story was or how you were kind of shaped when you were younger. Um, one thing you kind of talk about is how your parents came to the US with just $200. you know, it’s a lot of immigrants, I guess, like for myself too. My parents didn’t came to the US without too much money as well. Um, but I’m wondering for you like how did that shape who you were growing up like in high school and in college? Yeah. No, it’s it’s a great question, right? And I think it’s the beauty of this country, you know, America, that um, you know, people can come from anywhere in the world uh, and make make a beautiful life for themselves and their family. So, um, yeah, my parents, they grew up in China. Um, they came here for grad school, actually, Canada in particular. And so, when my dad and my mom first moved to Canada, um, they literally came with a suitcase and $200 in their pocket. Um, and they made do with what, you know, what they had. I remember my mom would always tell me the story of like when they went grocery shopping when they were young, like they would go to find bread that was like on sale or like they would go, you know, purchase um whatever was kind of the cheapest option available. Uh and now we have like, you know, Whole Foods, you can go get really expensive. You could go to Air1 and buy, you know, $20, $30 smoothie. uh which sometimes is crazy in my mind um just because of like where I came from and my background but it was obviously a huge influence in like for myself like thinking about financial independence and the importance of kind of building a good um financial foundation for myself and my family uh which has also motivated me a lot in terms of like career aspirations and building as well. So I think um you know that that kind of emerging underdog like immigrant mentality has really uh driven a lot of who I am and what I you know the the kind of passion that I bring to the work that I do and it’s also something that frankly we look for in a lot of founders as well when we’re kind of deciding who to back like you want to feel like there’s a hunger and a drive that this founder has for whatever reason it doesn’t have to be that you know they came from an immigrant background but there’s something that they’re out to prove and they have a chip on their shoulder. Um, and you know that kind of goes back to the mongoose mentality as well of like our firm is literally the symbol is like a mongoose. Um, and we want to find people who are hungry, punch above their weight, and they’re kind of like an underdog in what they’re trying to do. Do you feel like that background has caused you to be risk averse or did it is that something you fought at all as you were growing up? cuz I I can imagine and just also seeing from your first job, right? You go into banking which is a little bit more quote unquote safe but of course tough to get into. And then now when I compare it, you’re in an industry that’s known for being risktaking, right? You’re taking a lot of risk at times by investing in these early stage startups. So I guess the question is more of how do how has your approach and thought process with to risk changed from when you were younger up until until now? Yeah. I mean, I think you bring up a very interesting dichotomy, right? Which is, you know, as an immigrant, kind of coming from an immigrant family, the idea is like, oh, you want to find like a highpaying job that will make sure that you feel comfortable uh and you make enough money, right? And so I think you’re right that in the beginning of my career I started with slightly more I would say risk averse and more kind of stable kind of career paths uh which is joining an investment banking program being an analyst for 2 years then I joined a private equity firm you know all jobs that pay quite well from a you know coming out of undergrad as a you know fresh newly minted you know graduate right um but then I think the switch that flipped is that at some point I think you make enough that you’ve built a financial foundation you feel comfortable with and then that point was one at which I’ve decided well hey I can keep doing this and you know I could stay at Soft Bank or join another private equity firm or growth fund and you know be a managing director or partner and obviously make good money as well at that or you can kind of strike out on your own and start something of your And obviously the risk is higher but the opportunity you know upside opportunity is also higher too. And I think for me it was at a point maybe call it 3 or 4 years ago where I felt I’d built a bit of a financial foundation for myself where you know I I bought a place that I felt very comfortable with. I had some savings in the bank. Um, and I knew that, you know, if for whatever reason I didn’t have a job for a a year or two, I would be fine. Um, and that’s the point at which I feel like I wanted to kind of take that switch and just say, “Hey, let’s take some risk. Um, let’s do something really out there. Um, you could start a fund, you could start a company. Uh, but let’s do something that I’m really excited about.” And I feel like there’s going to be a lot more upside involved. So I think there was definitely a bit of that mindset shift from kind of the beginning of my career to kind of where I am today. And what would you say was what shifted your perspective? Because you kind of mentioned, you know, you have built some savings and so you have like a financial foundation, but was there I we’re kind of getting ahead of ourselves a little bit as well because um there’s a lot to go through, but was there some kind of shift that happened in your mentality or some moment where you decided, okay, I’m not going to go the route where I’m just going to stay at Soft Bank or work in private equity. I’m going to start my own fund. You know, I don’t think there was a specific like mindset shift moment per se, but it was also like I also have this very firm belief that life is very like serendipitous in that opportunities come and go from your life that you may not expect and you kind of just have to like grab on at the right time if you feel like it’s the right opportunity for you. And so frankly um you know I guess we’re getting a little bit ahead of ourselves but there was a point when I was at SoftBank where I started thinking about um joining an earlier stage kind of fund where maybe it’s a fund one or fund two like a relatively new firm where they could bring on like a senior person and also talking to um potential investors or LPs in venture capital funds and seeing if there would be an opportunity for me to raise capital and I built a very strong relationship with the family that is now my anchor LP in the fund. And so when the opportunity came around and they basically verbally committed say that they would anchor the VC fund I wanted to start, it was kind of like the opportunity is here in front of you. You’ve got to decide are you going to take this opportunity and run with it or are you just going to continue down whatever other path you’re still going. So in some ways I think sometimes life gives you a fork in the road and you just kind of have to decide at that point like do I take this opportunity and run with it or not and that was kind of where I was left call it two years two three years ago um after I’d built this relationship with my inker uh family office in the fund and what did that feel like cuz I’m also thinking at a smaller degree to people who are I guess familiar I guess a bit with my story where I left banking when I was around 25ish when I uh had just finished or was in my third year in banking and I didn’t have much lined up but that was like one of the big risks I’ve taken ever in my life and where I didn’t have my next step planned and I decided to eventually start my own business and all of that to me was very thrilling but daunting at the same time. So, I wanted to know for you like how did it feel to transition from having this very set out kind of path and then can you walk us through maybe I don’t know if you remember your day one or week one of like starting your new fund and what that was like? Yeah, I mean it was crazy because at the time I also had a lot of life changes at that same time. Uh so I’d actually got gotten married. I we got a dog. So, we had a puppy that I was like training at home and potty training at home. Uh and then we had also just bought a new place that we me and my now wife were going to move into. So, it was it was actually a crazy hectic time um that you know when when the fund started. Um but I remember just being at home and like just trying to figure out everything right like setting up the legal entities. I was on the phone with the lawyers all day figuring out different taxation schemes and what’s like the most optimal way to set up this fund, what’s the process of like getting all the documents signed up and filing filing the documents with like regulators or the SEC. Um, and so I just remember like the first few weeks I was just sitting at home just on the phone all day trying to figure out all these things I I knew nothing about. Um, so I definitely think it felt kind of overwhelming uh at first, but at a certain point, you know, if you have good adviserss that are working with you, like our law firm, Oric, um, they were always available, so I could like call call them anytime, talk about anything I had questions about. Um, we brought on like a fund administrator who does all of our back office stuff. And so slowly but steadily, I think if you have the right people around you that are helping you with setting up all these things and answering your questions, you feel a little bit more comfortable over time that like things are slowly working out and getting more um more and more kind of settled. But I think the first like month or two was definitely like chaos and just like I don’t know what I’m doing. Um and we’re just going to kind of figure this out as we go along. Um, and it’s fine, you know, I think it’s part of the journey of like learning and of being like an entrepreneur yourself. Yeah. I mean, would you consider that the first few months were more challenging or did you find it more like in that following few months or has the most recent few months like what part of the journey has been the most challenging? It’s been like two years or so since you launched the fund, right? Which is still relatively a new fund. Yeah, I would say the beginning actually there’s just so much like excitement and adrenaline that you feel in the beginning. I think it carries you through where you feel pretty excited about everything and also like the freshness um of like what you’re doing and starting something I think gives you a little bit of like a high that you kind of stay on for a couple months. I think the hardest part by far was fundraising. Um, so call it the first year of when we started kicking off the fundraising process and it was just a real grind because I was traveling a bunch all around the world. You’re refining the story and you’re refining the materials and figuring out what works and who you should be talking to. And it’s a very uncharted and kind of lonely journey I would say actually for fundraising for a firsttime fund because it’s unless you have someone that has gone through the process before. If you have a co-founder or adviser that can like really handhold you a little bit more through the steps, it’s just a very like lonely and long and hard journey to fund raise for a first-time fund. Um, so that was probably definitely the hardest part. I think that as an entrepreneur, you always feel the need to like challenge yourself though. So for me, even now, right, we’re always pushing. I’m always pushing myself and pushing my team to like do as much as possible to like there’s always more projects that we can take on. We always can bring in more investors into kind of the fold and collaborate with um different LPs or different VCs. You can always host more events. You can also do always do more social media, podcast stuff. So like for me, every day is a challenge and I purposely want to like push ourselves to continuously challenge ourselves. But I would say like the hardest part of the journey is probably that first year of fundraising cuz it’s just such a unique experience and it’s never easy asking people for money. So let’s say then that someone’s watching this right now and eventually they want to start their own fund. I guess like it could take hours for you to even explain so much of the nitty-gritty, but what kind of advice would you give them? And are there any stories also maybe that you could give us to portray just like how challenging it is at times or what it’s like basically to raise money because I think a lot of people even myself when I see all these funds like raising a lot of money even entrepreneurs when they raise money a lot of times they say that fundraising is extremely tough but then we we we don’t always know exactly what that means. So is there anything that kind of comes to mind? Yeah, I mean I can give you some like more concrete kind of data points, right? So, basically we were fundraising for about a year from call it like the fall of 2024 to the fall of 2025. Um, and I think I talked to I should go through the records, but I know that I talked to at least a thousand LPS. So whether it was Zoom calls, in-person meetings, um I met with at least a thousand potential investors for the fund. And during that period of time, I traveled probably for about like 40 to 50% of my time for that year was on the road. So I was traveling to conferences like Super Return is one of the big ones. Um they do conferences throughout Singapore, Berlin, New York, Miami, LA. So they host conferences all throughout the world. Was going to a bunch of those. Um there’s other big conferences like that as well. Um that are hosted by other organizations. Um and then I was getting introductions as well from like friends of friends, former work colleagues. Um and so I would often set up a trip around I’m going to go to Monaco for like a week, I’m going to go to London for a week and meet with like these 20 or 30 investors and just set up backtoback meetings, right? So there was trips where I would be in, you know, a city and I would basically be back to back, like eight meetings from morning to night, 1 hour each, where I’d meet like person after person. I’d sit in like literally a conference room or I’d sit in like a cafe of the hotel and just have people come to me one after the other, right? Um, and if you can imagine doing that for basically a full year, that’s like the level of kind of I don’t know what you want to call it, hustle or grind that it takes to like meet so many different people. Because one of the things I I learned during fundraising is your story and your um thesis and what you’re building is going to resonate with certain people and it’s not going to resonate with others. And part of the process, at least for me, was figuring out who are the type of people this is going to resonate with and who is not going to. And I think you can only do that kind of by trial and error. Uh, and collecting the data points, right? So we realized pretty quickly after meeting with a lot of different types of LPs, institutional LPs, family offices, individual angels and high netw worth individuals that what really spoke to like what the story that resonated most was kind of as a first-time fund, my background, the things I’d done resonated mostly with angels and high net worth individuals in some family offices and institutional LPs for a variety of reasons including the fact that a lot of them got burned during co had kind of stopped allocating a lot to venture capital and also many of them just couldn’t really invest in a firsttime fund or even a second time fund at that. So we realized quickly like here’s the profile that we need to target and sometimes in like a 30 minute meeting you can pretty quickly feel out whether someone’s really interested in what you have to offer or not. Um, and the goal is to like meet as many of those folks as possible and they’re going to kind of convert on their own timeline. Like there were times where I would meet with like a LP and uh we do a 30-minute call and it would be done after that. They’d sign the documents, they’re in there people where I met 6 months ago, we did, you know, many many meetings and they kind of disappeared. They ghosted us for like six months and then suddenly one day they reach out through the email and they’re like, “Hey, I actually think I want to invest in your fund now and then they they finally, you know, sign the documents.” And so it’s just a very like random I guess the best way to put it is like a super random process and trying to put some structure around it is helpful but in some ways I think it’s also just a lot of luck and randomness and noise and you just kind of have to keep going through and grinding through it with the expectation that like if you put enough hours and effort into it it will eventually work out. M. So I guess more person personal question is did that strain your relationship with cuz you said you had like a dog that you were taking care of and you’re traveling like 50% of the time. How did you manage like all of that or Yeah, I it’s it’s tough, man. Um I think my my wife is obviously like super supportive and amazing person. Uh my parents also like helped a lot. So they still live here in the Bay Area and we would often like drop off our dog with them for a week if we were if I was traveling a lot or if we were both traveling. Um so certainly like takes a big strain. Um, but you know, like I think there’s, you know, an understanding between like me and my wife that like this is something that I’m super excited about and you know, being like a founder, being an entrepreneur is like it’s a tough journey. So, you’ve got to make some sacrifices and I think having like people around you that understand and support that is also very valuable, right? Because it’s not going to be a 9-to-five, you know, job and journey. like there’s going to be late nights, there’s going to be really tiring, frustrating days and you want someone who kind of, you know, people around you that understand that and will like help support you through that at least if not like operationally then at least like emotionally as well, right? Yeah. I guess as you were talking about the most like frustrating times and then I was wanted to just know if and to close out I guess the fundraising portion a bit one maybe story of like the most frustrating moment or day and then one of like the best days. Oh wow. That’s that’s a that’s an interesting one. Um I I think during like the most tough like one of the most tough days was probably there was a very big um I think I think both stories tie in with like a big investor, right? Because I will say we have a lot of LPs in the fund. I think we have around 70 to 80 LPs in the fund. many of which are like angels and individuals, but the ones that like obviously stay in my mind are like the larger LPs, right? Because it’s like the one that got away that like the whale the whale hunting in a way. So, I remember there was one um bigger LP that we were kind of we had done a lot of meeting meetings with. It was kind of like a Londonbased family office um that had some like South African roots as well. And we had done I think like maybe six or seven like due diligence calls, meetings in person. I’d met him like two times in person, flew out to London. Um met for the first time in Berlin as well at a conference. And then after like six, seven meetings, suddenly they just like ghosted us. Um, and so that was one of the toughest things because they they said they wanted to potentially write like a5 to$10 million um, investment in the fund and those just really hurt because you feel like when you get to a point where you’ve done six or seven meetings with someone, they’re very serious. We put together tons of like materials and data room requests for them and to suddenly just kind of like lose lose that it just felt like a you know kind of a big blow. Um on the other hand there are also like there was another big Korean investor. So the interesting angle is we actually also have a very strong Korean uh network uh through venture capital friends from college and high school that I’ve known um and also just like a lot of the Silicon Valley um kind of Korean network here we’ve built out. We actually have a handful of family offices as well as two institutional LPs that are investors in the fund. And I remember one of these um institutional investors which invested almost $10 million into the fund um like we had been meeting and chasing them for like a year. Um and so to finally close out the investment from them after a year of talking to them and similarly doing a bunch of diligence requests, filling about around filling out a lot of Excel files and writing up memos and you know really long like text writeups about each of our portfolio companies and team composition and all this stuff. Finally closing them uh a year later was obviously like a fantastic day, right? cuz when you get one of these larger um commitments as well, it’s a very good way to build momentum with other investors you’re talking to because you can say, “Hey, we just closed this giant, you know, LP, institutional LP.” Um, you know, it lends a lot of reputation and credibility to like what you’re doing and the fact that you actually were able to get someone like that, right? So, I think those are probably like the two moments in the journey that I felt most kind of compelled by. I mean, this sounds like so much work and I I don’t know if this is true or not, but um if you’re constantly raising your next fund, then hopefully I mean, I guess you tell me that the process gets easier and it’s more efficient. But then I guess if you’re spending all this time fundraising then how do you manage the time to also actually do your other you know part of the job that’s kind of more important which is actually investing like how do you balance those two? That is a really really good question and it’s a super tough balance to strike. So, I will say that because Fund One, we kind of focused I was able to more focus on fundraising for Fund One and a little bit less on investing during that period of time when we were just first starting everything up. Um, I don’t know if I’ve actually gone through trying to balance those two yet. Um, which I think we’re going to go through for fun too. So, I’m not I’m not really looking forward to that because I agree it’s going to be really difficult to manage and balance both of those where we’re going to continuously be investing out of fund one and finishing out probably a few investments and then at the same time starting to fund raise for fund two. So, I’ll have to let you know how that goes. Um, but I think you’re right. There’s a saying in investing in in in venture capital or any kind of probably investing where you’re starting a fund where you’re always fundraising because even when you’re not actively raising your current fund, um you’re building relationships with LPS that hopefully could invest in your future funds. So I think the best way to do it is to always build a relationship as early as possible and to maintain that relationship so that the person already knows you even before you say hey we’re just started raising fund too like you know me for you’ve known me for 6 months let’s chat more if you’re actually interested in investing in fund two and I think that’s a far easier story than oh you know out of the cold hey first time I met you but you know we’re raising fund two you know I need to know within the three months whether you’re in or you’re out like it’s a much easier to just have that rolodex available um that you’ve built over the years slowly and steadily. Um, I think inevitably one side of investing or fundraising has to take a bit of a backseat. And in my opinion, if you’re in an active fund raise for your next fund, I think the investing kind of has to take a backseat, which is an unfortunate sacrifice that I think kind of has to be made unless you are a large institutional fund or a large enough fund that you can have like a dedicated IR team that does all the investor relations work. Um, or you just split the work where it’s like, hey, this partner does all the fundraising stuff. this person, this partner does all the investing stuff just so you can have like divide and conquer, right? Um, but I think inevitably you you have to make sacrifices on one side or the other if you have a really small team and you’re a relatively new fund like we are. So, I feel like when I hear about what you’re doing and all these different ways you’re being stretched, I kind of I think I feel like I relate to it a bit. um probably in very different context where if I’m I’m running my own you know small little operation and I have to do all these things for I’m I even do our own accounting on QuickBooks for example as a small detail and for you yourself you know if you’re a part of a larger fund then people have like these specialized roles but for you you have all these different things that you have to be doing um this more of kind of like just you personally um rather than a professional lesson but like personally do you feel I at anytime like overwhelmed with all these different things that you need to do and then if so like how do you approach actually getting through your list of things to do? This is actually something that I deal with quite a lot is like oh I I have a neverending list of things that I do I have to like prioritize and sometimes honestly I do get overwhelmed with all the things I have to do. How do you approach all of that? Yeah, I mean it’s funny I still like approve a lot of our wires like I do I don’t do the accounting. We do have a back office like uh a team, a third party vendor that does all of our accounting, taxes, etc. Um, and we do also hire like legal counsel when we look at deals and and documents. Um, I think, you know, for me it’s it’s trying to figure out where we can offload efficiently things like, for example, some of the finance things that we need to offload. Um, I think a lot of it’s also kind of figuring out are there things that I can bring on like a team member to help out with. So, we do have a few kind of full-time team members that um will take on some of these more kind of menial like maybe more administrative operational type of tasks. Um, but you know, I’ve I’ve figured out tricks, tips and tricks to like try, you know, offload as much as possible and then for things that I have to do, right? Like I think you know wires are a very important investment. You know we’re we’re wiring large amounts of money to make new investments and ultimately it’s either you get a CFO that’s very serious that you can trust to do that or I think like I should still be doing some of these things. You just find ways to be really really efficient um as much as possible. Like email is one thing that um it it takes a lot of time. Uh, I I wake up in the morning, I’ve got probably hundred emails plus. Um, and I use Superhuman. I have it filter a bunch of stuff. It’s super snappy and quick. I use AI, the AI drafting tools for a lot of emails that, you know, I can automate a bit more of. Um, and I think it’s finding ways to like quickly go through a lot of those operationally important and administrative tasks, but like doing it as efficiently as possible. Um, and you know, I think the benefit also of kind of, you know, running your own business as well is you have a bit more, I would say, autonomy in terms of like when you do things. So for me, like I try to get through a lot of my emails in the morning and also try to like do a lot of stuff at night or during the weekends when things are not as busy, right? So that I can get those things done that I know are important and I should do, but I have control over my own schedule cuz I’m, you know, not tied to the desk at like investment banking or private equity. And so, you know, I’m not looking I’m not making sure that I have facetime with my boss, but that means that I can schedule my time more appropriately so that I get the things done when maybe I have a little bit more free time and I should focus on these specific things at a different time, right? One thing you’ll notice about almost every person working on the buy side is that they started off their careers in investment banking. And that’s because it provides the most solid foundation for a career in finance. If you’re early on in your career and you’re trying to break into banking, I want to tell you about a student I recently helped named David, who landed four offers after working with me in my mentorship program, the Banking Accelerator. With every student, we apply our three-step recruiting formula. And so, we started with step one, which is pairing students with coaches that best fit their backgrounds and goals. David, for example, was a non-target student targeting New York. So, we paired him with a coach who went from a non-target to Goldman Sachs New York for all of David’s one-on-one calls. His coach then walked him through step two, which is going from zero to interview ready by covering recruiting foundations, resume revisions, networking best practices, behaviorals, and technicals. And the best part of the program is that you’re never recruiting alone. Step three is our community. David attended weekly group calls with me and other coaches and had 24/7 chat support from me, his coach, and other students. Ultimately, David landed not one but four offers from a non-target school. And if you want targeted help like this to maximize your chances of breaking into banking, book a free strategy call with my team using the link in the description or by scanning the QR code on the screen. We’ll assess your situation and let you know if you’re a good fit for the program. At the very least, you’ll get some good career advice. Hope to meet you and work with you soon. I guess on that note of there’s like FaceTime culture and banking. And when I’m thinking about the word culture and you running your fund right now, you know, you’ve worked in intense industries like Apollo is also known for being very intense. I’m sure SoftBank was also like very intense as well. What kind of culture do you have you kind of built at Mangusta? Yeah. Um, actually I have a funny story from Apollo. Um, it is it is a very famously intense place. Uh, but actually one one thing that I remember a lot, I don’t know if you saw it in one of my previous videos uh or interviews that I did, but there was once I was on a live deal. We were buying um Koba from uh Jack in the Box. It was like a very complicated like carveout transaction. And I remember the last few days of the investment committee and the deal closing, I literally slept in the office on the sofa in the lobby for like 2 days straight because I didn’t have the time to like go back home. You know, it didn’t really make sense for me to go back home cuz I would have like 2 to three hours of sleep. Might as well just nap it out on the couch. Um but yeah I you know just I guess it confirms you know it’s a very very intense work hard kind of culture. Um you know for me I think we are fully remote which is kind of interesting. Um I think even though we’re fully remote we are all like constantly on online reachable. So the entire team like I can pick up the phone and call anyone almost any time unless they’re sleeping and they will pick up or if I text we’ll respond within I would say usually within like 15 to 30 minutes but some you know usually a lot faster than that but like no later than probably like an hour. Um, and and I think it’s just part of like the culture of what we do. Like things move very quickly. Founders make decisions very quickly. Deals, you know, rounds, fundraising rounds and deals come together very quickly. Um, investors and LPs make decisions very quickly. Sometimes they’re hot and heavy for something, sometimes they’re not. And you’ve got to strike while the iron’s hot. Um, and speed like is is absolutely important here in Silicon Valley too. Like sometimes if you miss out you miss out on a deal, it could be literally the difference between like a day or two days of getting in touch with a founder, right? So I think that element of intensity when it comes to like responsiveness and just like the velocity of the work that we do is important to me. Um I think there’s a lot of things that are very different from like Apollo or like investment banking right I think there’s a lot less I would say financial modeling analytical kind of like uh rigor when it comes to like you have re you know have tons and tons of data that you can like sort through you know often times you don’t have that right you might have a deck basic financial model maybe some like customer matrix um and like cohort data and that’s kind of all you got to work with. So the I would say the name of the game I think in venture capital more so than you know private equity and and hedge funds is just getting access to deals, building the relationship that you have with other VCs, founders, building a reputation for yourself as a firm and a brand as well that people recognize, hey I’ve heard of Mangusta, like they’ve done really great things for their portfolio companies, help them grow um and you know they’re extremely supportive in Europe. I want to work with those guys. They’re really sharp. They’re really smart. Whatever it is. Um, and I think that is the core kind of focus of where we spend our time and intensity is like building out those relationships, strengthening them, doing events, building community, and then moving really fast when we need to around deals as they come together. Um, and so I think it’s intensity, but kind of in a in a different way, right? And I also think for what it’s worth, I don’t know why private equity firms and hedge funds and investment banking firms do this, but I feel like there’s almost this element of kind of being like very like sharp elbowed and having like a very a culture per se, like a personality in the office that’s like very cold and blunt where that just doesn’t fly in venture capital, right? like you’ve got to make friends with other investors. You’ve got to make friends with other founders that will vouch for you. Um, and same thing, I I I want my team to be happy and to enjoy coming to work and to be excited to work with me and work with all of our portfolio companies. Um, and there’s, you know, not really a place for in, I think, what we do, right? So I do think the culture when it comes to like personalitywise is a lot more I would say I don’t want to say relaxed but it’s a lot more like socially conscious that like we can’t be like we can’t be dicks like we have to be nice good people that people want to work with us and people want to support us and hang out with us because that’s just what we do right there’s so many I guess like questions that come off of what you just said I wanted to ask about first though when you know you’ve also mentioned previously that you had times when you were fundraising you met like a contacted or spoke with a thousand LPs and then for a lot of your work today you have to meet with a lot of founders and potentially other investors at times and it’s a very people facing role so and for you are you more introverted or extroverted and I I I’ve heard from my other V friends in VC that that doesn’t really matter, you know, like both can do very well. But I was wanted to ask about for you, which one are you and how have you kind of I guess if it’s extroverted, then I guess it’s obvious that you just played that to your strengths. But if you’re more introverted, then yeah, I think you have to use that in a different way. Um like how would you what would you consider yourself and what do you do you feel like it makes a difference if you’re one or the other in VC? Yeah, absolutely. So number one, I think extroverts in general from what I can see in in like business broadly I think have a advantage as an extrovert. Um, I think there’s probably quite a lot of I don’t know if there’s a bunch of data points and studies out there, but I think people who thrive off of like meeting a lot of interesting people and like communicating a lot and spending a lot of time with other people just innately have an advantage when it comes to building relationships. Um, I am actually very introverted. um which is very hard to potentially see when I am interacting in public or when I’m um you know at an event or speaking at a conference or something and just like my persona right I like I think I I do have energy and I do have a lot of passion for what I do but I would say that I am very introverted when it comes to like in my own free time what I like to do is just like stay at home watch TV hang out with my dog uh hang out with my wife like not not not going out and like socializing a ton when it’s not something that’s like workrelated. Um and so I am I guess like a trained like extrovert in some sense for my job, right? Because as as you mentioned and as I mentioned like I had to go out and meet say a thousand LPS. Well there’s that’s a lot of people to meet, right? And that’s going to a lot of events, going up to a lot of strangers. And I think there is an element of even if you’re an introvert, I think it’s helpful to train yourself to be an extrovert, you know, from time to time, right? Like you can selectively turn it on and off. You don’t have to be an extrovert always, but if you’re going to a networking event, if you’re going to a conference, if you’re going to, you know, um, something that’s like a dinner, like it is helpful for you to make new relationships and contacts at that event and you need to put yourself out there. Um, and if if that’s not what you want to do, then maybe this is not the right job for you too, right? Because you have like in a field like venture capital, part of the job is like you have to build relationships, you have to source uh deals, you have to source LPs and investors. Um and it’s not easy, but the more you do it, the easier it becomes, right? Um I was very shy when I was in um middle school, even high school and even college, I would say. But like there were things that I would do which would gradually get me out of my shell. Like one of those things is like speech and debate I did in high school. I highly highly recommend for I mean I don’t know if you have high schoolers or like college students probably college students watching but like you know highly recommend like public speaking uh speech and debate type of activities just because it like forces you out of your comfort zone if you’re naturally a shy person and you have to go out and say something and not be afraid to like make mistakes or say something stupid right in front of a big crowd. And that’s fine, you know, we all make mistakes. We all learn from those mistakes and that’s part of the process of growing and improving, right? Um, and so I just constantly kept putting myself in those situations where I’d be, you know, vulnerable and I would make mistakes, but I’d learn from those opportunities. And I keep doing that even now, too. Right? I’ll I’ll go speak at conferences. Um, and you know, you try to prepare as best you can, but it’s also just an opportunity for you to practice putting yourself out there. Um, so yeah, I mean it’s it’s a fascinating question because like I think it on one hand it’s like a question of like can you change who you are? And I think in some ways like yes, I think you can. You know, we’re all very moldable and our skill sets are very transferable. Um, and you know, you should do and and I find I will say another difference is I have a lot of energy when it comes to like talking one-on-one with people. I think I don’t like being in kind of larger group settings and having to like spend a bunch of time in kind of larger groups. But when it comes to like one-on-one conversations, I find that I can go for like hours with talking to one person if there’s like a really interesting thread or conversation here. um because I think it’s just really interesting to like learn about someone else and hear what they have to offer and what they what their life experiences are. And so I often find myself asking a lot of questions to like even LPs that I meet because I want to understand who they are and how they think about the world. Um, and it also helps me figure out, hey, is this someone that actually, you know, is probably interested in what we’re doing and, you know, I want to spend more time on because part of the thing I learned about sales and fundraising is it’s actually less about pitching. It’s more about listening, right? You have to listen to what does this person care about? What does this person want? And is what I’m offering aligned with what they want? because if it’s not, there’s no amount of pitching that’s going to get them over the line, right? Um they just they’re just not interested in what you have to offer. And that’s fine, right? You should that’s a great way to say, “Okay, I’ve put in enough time and effort here. This is probably not necessarily a good lead for me to continue following and let me go and find another lead that I can go, you know, follow, right?” Um but it’s helpful information for me to know what does this person care about? Um, and that only comes by listening and asking questions. Yeah, that’s kind of similar to what I said my friend in VC who is an introvert. And when he went into VC, I was, you know, I hear a lot of the times that in VC you have to spend your times like meeting people all the time and whatnot. And so I asked him about it and I feel like he did he said something similar to you that you can play to your strengths as an introvert by kind of like being a good listener and being more in tune kind of when someone else is speaking, leaving more room for them to speak. And I would imagine that there are a lot of people who are VC investors who are, you know, very maybe like loud, really good with people, which is great, but then when it comes down to a one-on-one conversation, yeah, the when you’re trying to convince maybe a founder or investor to work with you, they don’t want to hear you talking all the time, you know, they want to be the ones talking and you you’re kind of listening, I guess. Um, so that makes a lot of sense. And I think we we kind of strayed away a bit from uh what I wanted to talk about at the beginning so people could have more context, which is kind of like your experience um in at at in private equity and in in at your hedge fund and at SoftBank, which is a bit more growth. Um, so I wanted to kind of shift a little bit there and then we can I guess go back into VC a bit more. But um, one thing that you’ve talked about in your previous convers in your previous interviews is that at Soros you kind of learned how to take chips off the table and sell into sell down into appreciation. And so I wanted to, you know, there are not a lot of people who can talk about ex their experience like at a hedge fund. So I wanted to kind of first focus on that lesson that you learned and if you could walk us through maybe like a specific trade where that kind of lesson got drilled into you. Yeah. No, it’s it’s a good um it’s an interesting point, right? because um in most private investing whether it’s like private equity or like venture capital you typically don’t have an opportunity for liquidity every day right you typically you enter an investment you hold it for a number of years and then you do an IPO or an M&A um but that exit is kind of sometimes it’s out of your control and sometimes it takes a very long time um with a hedge fund you know you are looking at your portfolio every day and you can decide to buy more or sell every single day and so the world of possibilities is open to you which makes things honestly quite hard too right because you have a choice to make every day do you buy sell or do you hold it um and one of the things that my um the PM that I worked with at Soros always said was you know when when a stock goes down. You know, it’s very counterintuitive, right? Because um in some ways it’s like kind of going against what the market is is saying or doing, which is if something goes down, uh if a stock goes down in price, but you still believe in the thesis and you still believe in the upside, then you should buy more, right? So something goes down, you buy more and you keep loading up on more stock of something that you believe in. And then similarly if something goes up and it hits say your target price you know say you buy whatever Apple for example and it goes you know doubles in stock price over the course of 3 months and you’re like oh this is great like this is where I thought it should trade. Well then if it reaches your target price you should sell out of that position as it gets to your target price. Right? Theoretically, once it reaches your target price, if you are accurate and you have a lot of confidence in the analysis that you’ve done, then theoretically you should sell out of your position entirely by the time you get to your target price because you don’t think it’s going to go up anymore, right? Um, and so that way of thinking is something which I also try to bring a little bit into venture capital because I think that there’s a bit of a there’s venture capitalists I think are very good at entering positions and investing and picking companies. They’re very bad at exiting companies. Um, and they often don’t really think at all about exiting companies, right? they just kind of let it sit there or hold it until it either dies or it IPOs. Um, and I think taking a little bit more of an active approach to managing your portfolio and positions is very helpful and thoughtful. Um, which a lot of VCs don’t frankly do. So when I bring it up with LPs, they actually really like that because they’re like, “Oh, this guy actually has spent some time investing in other things rather than just being a VC for his entire career, right? Um, but it’s one of the lessons that I took away from kind of my hedge fund experience. And I think if you talk a lot of uh hedge fund folks, they will probably say something similar that it’s it’s important to kind of trim add and trim to your positions as you gain conviction in the price uh of an opportunity or you lose conviction in the price of an opportunity. But how do you think about that where in hedge funds there’s a ton of data and you can build models that are quarterly even like monthly maybe even weekly if you have the right information. I guess in VC you if you have access to it with your portfolio companies then you can get that data as well but then ideally you know when you’re at the early stage the growth is supposed to be kind of explosive. So then I guess the two-part question is first how do you sell into appreciation and build the confidence when your models which famously you know any model you build is most likely wrong because uh it’s there’s just so many things that change. So then like how do you think about in your current role in VC actually feeling confident, oh we should sell into appreciation when things are supposed to explode the the earlier you you you’re in so you may like lose out on potential gains. Um how do you model that out and think about that? Yeah, it’s it’s a good question. So I would say for us we underwrite like every every investment we make we underwrite to at least a 10x opportunity and that’s our base case because that’s what we that’s what we’ve uh told our investors is kind of what we expect the return of the the fund will be over the course of the fund life. Um and so every investment our base case is at least 10x and then the upside case can range but usually anywhere from whatever 20x to maybe 100x plus right I would argue that if a opportunity if a portfolio company of ours has performed so well that they’ve reached kind of the upside case scenario that we that we modeled out. I would say whether it’s whatever 20x 50x, we should take some of the chips off the table, right? Doesn’t mean that we have to take all of it off the table. Like, we’re not going to sell 100% of our position, but if we can take 20% of our position off the table, a quarter of our position off the table, and then we return some uh equity, you know, return some cash and dividends to our LPs. I think that is a very prudent way to manage money because we don’t know where the world will be going, you know, next year, five years from now. Um, we could be in a global pandemic. Um, and if you invested in a business that does travel, you know, it’s going to be a really tough it’s going to be a really tough path, right? Um, but if you can take some chips off the table and if you sell, you know, whatever it is, 20% of a position that’s gone up 10x, 20x, you’re going to make still a very, very good, you’re going to return the basis of that investment at least, plus probably some upside on top of that, right? And I think there’s very few LPs out there that will be disappointed or angry that you liquidated, you know, 20% of a position that’s gone up a ton. Uh because they also want to know, hey, you’re thinking about my capital as if it’s your capital, making sure that we return at least our basis. Um and setting at least a foundation, right? A financial foundation of like, hey, this is, you know, we’ve already returned your basis in the fund. So you can know that like your capital is at least preserved, you know, whatever 1x and then on top of that we still have 80% of the position that’s still has upside uh exposure. Um and so I think for me there is obviously an element of like oh say that it becomes a,000x one day then you know you lost out on 20% of a,000x. Yeah. Um, that’s true. But I think in a lot of these scenarios, I feel much more comfortable with telling our investors like, “Hey, you know, we are very prudent, fiscally responsible managers of your money, and we’re going to make every effort we can where we think our target return or upside return has been hit for this specific investment and we are we want to take some money off the table and return it to our investors.” Okay, that makes sense. And so that sounds like a very important lesson you’ve implemented from your hedge fund days. I was wondering maybe also from your private equity days. Was there anything that you learned from there that you also imply to what you do today? You know, it’s it’s a it’s a good question. I would say there’s not as much that’s I would say directly applicable perhaps. Um cuz I I just remember in our private equity days, a lot of time was spent on uh financial modeling and um really detailed drivers and assumptions in those models which obviously we don’t do as much of in early stage or growth stage venture capital. Um and the second area we spent a lot of time on was negotiating legal documents and uh financial kind of accounting documents or working capital pegs and things like that which obviously we don’t also negotiate a lot in venture capital either. So I feel like there isn’t a ton that’s directly applicable. The only area that I think is interesting I would say is just the element of relationships and deal making. Um you know I think making deals happen and making investments happen is just a highly personal especially private transactions happen. It’s a very relationship driven business and it’s a personal human human to human kind of business, right? And I think, you know, regardless of what you think about Apollo, I think that there was definitely an emphasis on like relationships, building good relationships with good operators. Um, and if they can help you come in to run a business, fix a business, like they would often bring in the same CEO if they were just a rock star to run one business and then you know that does well, they bring them in the same person in to run another business. Um, and just finding good people to work with that you trust and trying to make those deal opportunities is something that, you know, I do bring into what we do here. Um, obviously it’s a little bit different because instead of dealing with probably like more middle-aged kind of um, you know, professional business professionals of like almost public companies at private equity, you know, usually we’re dealing with kind of 20 to 30year-old young founders here in Silicon Valley. So, it’s different ways of building relationships and getting to know someone, but in a similar way, you’re really trying to find a connection with someone and making the relationship such that you believe like they’re going to be someone that you can count on that you want to work with. And it’s a long journey, right? If you invest in a a startup and um you know you join their board, you’re with them for the life cycle of that company, which can be three year, it can be one year, 3 years, 5 years, 10 years. Um and so it becomes a very very long-term relationship that you build. And that’s something that I I really enjoy about what we do as well. And it seems like honestly you didn’t enjoy the PE part too much. I can also maybe gather that for because you stayed there for just one year, but is there was there a big reason you decided to make the the move? Um cuz you know a lot of people obviously after banking they go into PE that’s kind of what they want to do and they they’re there for like at least a few years and then maybe move on to something else. But was there something that caused you to want to move into hedge funds? Yeah, there I mean there were a couple of things and just to be clear by the way I joined um so I was at Apollo for about a year and then I joined SoftBank and then hedge fund was actually in the middle of my time at Soft Bank. So yeah, it’s a bit of a strange journey. I joined I joined Soros for one year during COVID kind of just as a way to try out the space. Um but the the transition from private equity to to uh soft bank to more like growth and venture. Um there were a couple of things that really influenced my decision there. One was when I was at Apollo, you know, no offense to Apollo, but the way that they think about private equity investing is very valueoriented, right? Almost in some cases distressoriented. um where they’re looking for a cheap multiple, really good cash flow, and um an opportunistic transaction where for some reason this company or this business has fallen out of favor or has self-inflicted some big issues in itself. Um and I saw I think they’ve performed very well as a firm, right? They’ve obviously become one of the best firms in what they do. But for me, it wasn’t as personally exciting to be investing in and kind of helping turn around businesses that were really really struggling sometimes because it was just a fact that their industry or what they did, their business model was starting to become more obsolete. Um, you know, I think, uh, there was one business that was like Chuck-E-Cheese. Um and you know I I used to remember love going to it as a kid. Uh but like there are just so many trends against against it. Um you know healthier foods like other you know sorts of recreation not not indoor and you know such a space and co obviously was also not a great not a great thing for them as well. Um, but it just felt like the businesses we were investing in were not going to be the businesses that would be around for like the next 5, 10, 20 years. Um, and so I think for me a big part of it was um, do I want to be working with the businesses that will be growing in the future or just kind of helping these businesses that will probably sunset over the near term and just extract some value and cash flow out of it over the next few years. Um, so that was one thing is just kind of like a philosophical perhaps difference in how I thought about investing and what I personally want to invest in. And then I think the second thing that I felt um really influenced my decision was I I thought about like what do I think I’m good at? What do I really want to be doing with my time and is it, you know, sitting in front of an Excel file and a really complicated financial model and making sure that all the drivers are really buttoned up and there’s no there are no busts in the model. um and negotiating legal documents for hours on the phone with with lawyers. Um and you know, don’t get me wrong, some people love that. Like there are plenty of uh you know, graduates from for example, there were a lot of Wharton graduates at Apollo uh both undergrad and and MBA grads and I think they genuinely many of them genuinely loved doing the accounting, financial modeling, legal due diligence and negotiations. Um, and they just really enjoyed that work. Um, and that’s fantastic for them. I think private equity is great for them. But for me, I just realized that’s not what makes me excited to get up and go to work in the morning. I want to like meet interesting people. I want to uh learn about really interesting new spaces, new markets, new technologies. Um, and I I felt like I really wasn’t getting a lot of that like relationship building or kind of um networking and sourcing experience. And you won’t really get that I think in private equity until you get to like a senior level as a partner or maybe you know maybe as like a you know whatever junior partner principal level in private equity like unless or maybe if you’re at like a mid-market firm um that’s different because they’re probably more sourcing models involved there but at like a large private equity mega cap firm like the sourcing and relationship building side of things really only kicks in once you’re kind of like a senior level person and so I felt like Well, you know, I could try to grind it out for the next whatever 5 to 10 years and see if I can get to that or I can just put my what I think are my strengths and what I want to do to practice today and actually try to do that in venture or growth which is what I ended up deciding to do. Um, so it was yeah, I think it was, you know, both of those kind of elements that I thought about which takes a while. Like I’ve always believed trial and error is the way to figure out like what you enjoy, what you’re good at, um, and where the world is going. Like those are the three things that I always triangulate for. Um, is like where’s the world going? What do you think you’re good at and can excel at? Um, and what what do you enjoy doing? Um, and if you find something that kind of hopefully matches those three things, I think that’s like a recipe for like career success and kind of happiness. Mhm. Yeah. Yeah, I like that framework and I’ll definitely have to think about that more myself as well. Um I So you went from I actually probably looked at your LinkedIn wrong cuz I I think I saw Apollo then Soros and then SoftBank but I didn’t look at the years or something then. Um so then you went from Apollo to Soft Bank’s vision fund and you know everyone knows that they started the hundred billion dollar fund and um you were kind of there in the early days in the first in the second year or so. Is that right? Yeah. I think we I think officially maybe started in like I don’t know 2016 but it was announced pretty publicly in 2017 and that’s 2017 2018 is where the team did most of the hiring and growing like did the most growth I guess and so when you were there um cuz as we talked about before uh we actually began speaking like I went through the interview process when I was back in banking as well and so I remember during that time a lot of people were being like hired and it was a pretty exciting opportunity. And when you got there in the first few weeks, you know, like how was, you know, the first few weeks there, first year there, like what was that like? Yeah. I mean, the way that I kind of describe it for people is like think about being at a really well-funded startup. Um, and that’s kind of how it felt for like the first year or two. Um like one is in the beginning we didn’t even have titles. They were like you know everyone was an investor and then they had HR then they brought on an HR team. They had to standardize titles. They also had to standardize uh compensation. I think for a while they didn’t even have standardized compensation levels which like most private equity and investment bank like most finance firms have a very um very very organized like compensation and title structure for every single level. Um, and so over the first like 2 to 3 years, it was just like everything was being built, like the boat was being built as we were going, setting sail. Uh, which was kind of cool in some ways because I think it allowed people to basically take on much more responsibility than you would typically get. Um, you know, I was technically like a senior associate when I first joined and I was like running deals as if I was like the managing director or like a partner on like a a traditional kind of like whatever growth or private equity fund because I would be like helping negotiate the term sheet and I’d be like, you know, presenting in front of the investment committee which typically like you don’t usually like the deal partner or like the lead partner is like presenting ing the deal, right? So, I think it was just a really unique opportunity for me to and and for everyone and in those early days to just get so much more career experience and acceleration in learning that you wouldn’t really get somewhere else. And that’s the beauty of joining a startup too, right? If you if you start your own startup or you join a startup, arguably there should be more opportunities for you to step up and push the boundaries of your own skill set because they want everyone to do as much as possible. Um, and so for me like you know I I remember there was one time I was presenting I brought a company to MASA who is effectively our investment committee and it was like a robotics company and Masa really loved the company. So, at the end of the call, he was like, he looked at me and he was like, “Kevin, you need to get this deal done. Like, get this deal done. You know, we need to invest in this company.” And I’m like, “Okay, yes, Masa. Like, I will I will do this for you. Like, I understand.” Like, and I’m like, “Oh my gosh, like if I don’t am I going to get fired if I like don’t get this deal done? Like, is it is it over for me?” You know, there’s there’s a certain level of like pressure. Like in some ways it’s obviously great to like get that experience of like you know interacting with basically the CEO of of you know one of the biggest investment firms in the world but on the other hand like you feel a lot of pressure and uh intensity of like your neck and is on the line right like you’re really responsible for this. Um so it’s like exhilarating and like terrifying at the same time. So, how did the meeting cadence work in terms of like maybe with MASA or like did you guys because there are different like pods almost in SoftBank and you guys all kind of were managing different things. I’ve also heard that at times it didn’t feel as much investing because sometimes be like Masa wants this and this and this so we’re just going to have to like do what he wants. But I guess you mentioned in your example that you had brought an idea to him. So I guess how did the meetings work? How did the investment decisions work um in the fund? Yeah, so it changed over time but generally um in the like the the heyday of like when we were very active, we would basically have a meeting with Masa every week. Um, and so he would do like a I forget what day of the week it was, but think of it as like a Monday morning kind of meeting where we would run through the pipeline of whatever people were bringing forward to him and then there would be investment committee where you get official approvals. Um, and in the very beginning before COVID happened, we would actually fly out all the founders to meet with MASA in Tokyo. Um, so it was crazy because sometimes you’d literally fly a founder out for like a 30 minute or one hour meeting and then you fly right back. Um, and you you know you’d usually try to like tag on some other meetings and maybe stay for a weekend if you could. Uh, because it’s a long flight, right? Even from the west coast to like Tokyo. Um, but I remember like we would be bringing, you know, Masa always liked to meet the founders in person and so we would try to bring like at least one or two founders to meet with him every month and there were about five or six teams at the time that were kind of structured like pods. So there was one managing partner who would run their own pod and so think of like six different pods that were each bringing forward the deals that they wanted to do. Um, and there was an element of both of the things that you kind of mentioned, right? There was some element of if there’s a managing partner that really liked a particular founder and deal, they would bring it forward to MASA and kind of, you know, have their own conviction and agenda with wanting to do that deal. There are also cases where Masa would say, “Hey, I really like this company. Like, can we get in front of this founder or this company?” Uh, or he’d say, “I really like this space. like I want to do some more robotics investments for example and people would go crazy and be like okay I’m going to go source this robotics company and then you know inevitably there’d be some kind of overlap because this team reached out that team reached out um so there would there’s also like a decent amount of like chaos when it came to covering different areas and different founders but through multiple different teams. Um, so lot of interesting I mean so many interesting stories from SoftBank times. Um, but you know all in all like I still feel like it was a very great learning experience for me and for a lot of us because especially when you’re earlier on in your career like you usually don’t get to meet and take on that much responsibility. You kind of mentioned a little bit that there were a lot of great stories from SoftBank. So yeah, I was wondering if you could share any that are particularly interesting. Also, people love hearing stories about Masa as well. So, anything that comes to mind that you feel like would be like fun, entertaining, insightful, educational. Yeah, I mean there’s just so many funny stories um about him. I mean, I think there’s a couple I’ll start with maybe a couple of things that are like I respect and and think that he’s one of the best in the world at. Um, I think one area is like he is the most charming person that you could ever imagine that like a relatively short like Japanese gentleman could be. Um, like he has a really good sense of humor. He like makes Star Wars jokes. Um, he’s has this like presence or like aura about him that’s just like gets people. It’s like kind of mysterious, but in a way like because of it, people think that he’s like a genius. Um, and I think he’s just like a really good storyteller and very charming in the way that he does it. And I think the best kind of manifestation of that that proves that fact is that it’s not easy to raise a hundred billion dollars, right? Um, and the fact that he was able to do that, um, is is pretty is like I think a testament to the capabilities that he has as a as kind of like a charming like storyteller and like as a a salesperson honestly, right? Um, so I think that’s like the first thing that I would put out there. He’s like super super optimistic. He understands the art of deals as well. Like one of the interesting things that he used to do a lot um including in one of the deals that I worked on when he’s in a meeting with a founder in person and he likes it so much he will effectively either write on the whiteboard a term sheet so he’ll basically say I’m going to invest $1 billion at you know 4 billion valuation uh we will have you know JV in Japan an uh we will help you expand here and we will close this deal in the next 2 weeks and he’s like I sign here you sign here you know uh on the spot like after like you know a 30 minute 1-hour meeting with the founder or he’ll do it on like a napkin. So, we used to have these um it was like the craziest thing for our legal team cuz we’d basically like he would write the same thing on a napkin and they would sign the napkin and then we would have to take a picture of the napkin and send it to our legal team and say, “Hey, we need to draft a legal document that reflects what is written here on this napkin.” It’s like this is a term sheet that was written on a napkin. Now, make it legal and binding. So then even though all the details aren’t on there, so I’m sure like after that would there still be a lot of negotiation or like because is it more symbolic or Yeah, in some ways it’s symbolic I guess. So like you know obviously a napkin is not a binding, you know, document with like five scribbled words on it, right? But I think in a lot of ways it it set it set the stage. it set the most important details of like here’s the valuation, here’s how much we’re going to invest, and like at least you’ve gotten like the big things out of the way, right? So, there’s not a lot of negotiation on those bigger points, but obviously on the finer details like maybe you want to negotiate um you know, when the deal closes or like is it you know, is the valuation fully diluted? Does it include like an options pool? like there’s some finer details you can hash out, but at the very least you get like the big details sorted out with the napkin, right? Um, and I think it also just represented like Masa as a as a dealmaker, right? He understood the the art of like if there’s something that’s really hard to get access to or there’s a founder that he really likes and he really likes this business, he knows that like you’ve got to pounce and you’ve got to strike while the iron’s hot. And the moment when you know part of that is kind of like an intimidation. I feel like people are charmed when they get flown to Tokyo and they meet with Masa and it’s a huge boardroom and you know he’s he’s got this presence around him and then he’s got his like entourage of like five or six advisors that are sitting around the table and you just feel like you’re going to make the deal of your life, right? Um and so it’s also a great opportunity for MASA I think to basically say here’s the deal. you need to sign this now if you want to like if you want to be like the next Nvidia or the next like Door Dash or Uber like you should sign this deal right now with me because I’m going to make you a superstar. Um so I think there you know when I think about it there was also this kind of like reverse sales salesmanship that he was doing with the founders where he was like striking while the iron’s hot and also getting them very excited about partnering with MASA. Right. Interesting. Okay. Yeah, I I mean I can imagine being a founder in that situation as you said being flown to Tokyo and then meeting with him and then all of a sudden you’re just like signing this term sheet on it. It almost sound sounds comical but at the same same time it’s like fun because of that and all of that I’m sure like pulls together really well to to ultimately like get deals done or at least the deal process started. Um, so you’ve kind of mentioned before in other interviews that um, Masa was like and as you’ve spoken about he was like a big influence in terms of like dreaming really really big. So I wanted to ask for you and Mangusta like how big are you trying to build the firm into? Yeah, I mean that’s a good question. Um, and it’s one that I think about a lot myself because you know the first thing I’ll say is bigger is not always better. Um, and you know it’s something that I want to be very thoughtful about because when I think about what’s like what’s the north star when you’re starting an investing firm, I don’t think it’s about building like the biggest fund possible, right? I think for me my northstar is I want to generate the best possible returns um for my investors and to help them achieve whatever their goals may be right. Um you know most of our investors are financial investors in which case you know um investment returns is probably their northstar as well but you know for some like maybe they have strategic goals where they’re learning about AI or they want to implement AI into their you know businesses uh that are more legacy businesses and we’re helping them get more educated and more exposure through kind of investing and and learning about these assets um and technology. technologies. And so for me, when I think about where we want to take this, I think a part of it is like growing in a reasonable um thoughtful way to continue to achieve those goals of like providing the best possible returns to our our LPs. Um but at the same time like you know I do want to build I think a generational kind of firm and a platform that I feel like captures the essence of like who we are and who I am as a as kind of like a founder and entrepreneur as well. Um which means I think hopefully getting you know bigger over time. um but with a focus on continuing to find like the best hungry entrepreneurs who want to partner with us and who like we want to change the world with. Um and so I think you know we we’ll start with fund two you know it’ll probably be bigger than fund one that’s you know whether it’s you know two times larger or something else we’ll see but I think it’ll be larger than fund one um I do think we are going to do a bit more growth investing just because the way that the markets have been evolving uh quite recently with AI and tech investing. I do think a lot of the best opportunities almost jump to kind of a growth stage very very quickly at least in terms of valuation. Um and those are often the teams that are best equipped to like succeed in what they’re doing. Um and so I think we need to adapt to where the world is going and I think that part of that involves being willing to play a little bit later stage as well which plays in very well to kind of my softbank background and network too. Um and then over time, you know, I think we’ll we’ll see where the world takes us. Um you know, I think there always are thoughts about, you know, the secondary market is a very interesting one that I’ve also thought about potentially doing more in in the next kind of 2 to 3 years if we have the right people and the right platform for it. Um and yeah supporting other kind of emerging fund managers like I think uh there’s a lot of really really interesting funds and a lot of very close friends who are you know also starting funds and I think there’s ways that I want to work with them as well to help support them. So, a lot of different ideas that we’re exploring, but I think for us the focus is going to be on Fund 2, making sure that we uh do a good job with with performance there and and finding great companies and great LPs to partner with. Um, and for me, it’s a bit also like not really thinking too far ahead in terms of like, you know, what is necessarily like the end goal. I think a lot of what I how I want to like build things is like one step at a time cuz like I think you can always see maybe like a year 6 months to a year in the future I think you have good visibility to like what you want to do where the world is going but like when you think about like 3 years out 5 years out 10 years out it just becomes a lot harder because there’s so many different variables at play and the world changes so quickly that it’s hard for me to say like where do we want to be in 10 years. Like, who knows? We could be in space. You know, maybe we’ll be starting a space colony fund in Mars or something. And, you know, there’s no way that I would be able to predict that today. Yeah. Yeah. Yeah. That that makes a lot of sense. I mean, I always I also think back to my own life and I think the same exact same thing. I thought my life would turn out a certain way and then here I am like running a YouTube channel talking to you when I started off my career in banking. Thought I’d be in like a normal finance path. Um, but I think uh we’ve covered so much. Um, and I just had a quick few last few questions for you though to kind of pick your brain a little bit. Um, one is since you invest in so many AI companies, I wanted to know a bit about your own personal like AI stack and like what what products you use um, and you think are kind of like the best out there. Yeah, it’s a good question. So, I will say with a caveat that I’m probably not the most um how should I put it like technically oriented uh like GP out there in terms of like testing out a lot of the latest like AI tools. Like I know a few of my um fellow like emerging manager friends uh that actually have built like their own like open claw agent and they bought like a MacBook um whatever it’s like a Mac Mini and they like booted up with everything and it’s crazy. Um so I have not done that but what I do use AI for I use it a lot for I would say email um drafting uh document review when it comes to like agreements uh sometimes like just preliminary legal doc review as well a lot of like memo writing and drafting when it comes to that too we do a decent amount of kind of like due diligence memos IC memos um so I usually use Claude for that. Um, honestly, I find a lot of them pretty similar. I would say Claude is maybe like slightly better, but I use like Gemini. I use GPT as well. Like I find them pretty interchangeable honestly. Uh, for things that I’m doing which are not super super advanced. Um, I do use um from time to time I’ll play with like Replet, which is also one of our uh portfolio companies when it comes to like thinking about changes to our website. Um, and like helping like code very simple apps here and there. Um, and then a aside from that, like not really that much to be honest that comes to mind. like we maybe a little bit of like editing software like um like video editing stuff like I started doing talking head videos as I I talked about like I’ll use like cap cut and stuff for that um but you know I don’t count it as like really super hardcore AI tools. Um we are also going to experiment we’re starting to experiment with some interesting like CRM AI agent oriented like CRM tools because um we use Affinity right now which is a very common like VC uh CRM system but it’s quite expensive and it’s a very like legacy it’s like an Excel table online where you like fill in each of the cells and like it’s okay but I’ve heard that now there’s like these AI agents which you can like literally give them commands and it will go and do the things that you want like send a bulk email to these people or whatever it is and you can like have a conversational CRM effectively. Um and so that’s something that we’re going to try out as well. So we’re always looking for like new tools uh and tech stacks that we could use that will help us with what we’re trying to do. Um, but my general view is like if something is working pretty well for me, um, you know, I’m not necessarily going to switch unless I see a huge ROI from it. Gotcha. Gotcha. Okay. And then last two questions. Uh, one is, you know, you’re a founder and you have to hire a lot of people. You also interact with so many people. So you have like now some you know you’ve built a pretty strong radar I was I would assume of getting to know someone pretty quickly. So let’s say you’re hiring someone. What kind of interview questions do you like to ask and look for in people you hire? Yeah. So this is an interesting question because I actually don’t believe that interviews are a great way to hire people. um if you can do it and if you can afford to do it, I like to have people do like a trial period. Um and so just think of it as like someone works with you part-time for a month or two. Um obviously it’s hard to do if they have a full-time job that they’re already at. But I find that the best way to figure out who you should hire is by actually working with them for some period of time. Um so we we try to do that a lot here at Mangusta as well. um like most of the full-time folks we have started out as like part-time trial folks. Um but in terms of like interview, I would say like we obviously try to do interviews in the first few kind of meetings to decide if we want to bring them on and and help them, you know, have them do a trial period. I think one of the things I really look for is um I would say like competitiveness. Um, you know, I want to know that someone has a certain level of like drive and hunger to like succeed. And so I’ll probably ask like what’s like the most competitive thing that you’ve done, you know, in your life or like what what were some like highly competitive activities, whether it’s sports or some other activities like chess, whatever it is, something that someone just really got very passionate about and really wanted to succeed in. Um because frankly I think most people there’s like a smart enough bar that I think most people pass and after that it’s basically like do you have the drive to continue to succeed and push yourself and improve and I can teach someone almost anything that they need to learn for venture capital. It’s not rocket science but I need to know that someone’s going to really push it hard and be willing to like put in the effort to grow and succeed, right? Mh. And so I think that’s like one of the key things I look for. Um I think the other thing is like you know depending on what role that you’re hiring for obviously you need to ask technical questions if you’re hiring hiring for a very technical role. Um but for me I think the other area that you know I really look for is like responsiveness. Um, and that’s something that you get from just like strange like little strange tests here and there, right? Like responsiveness or what I call like being always on. And so like there’s a couple things that I I test for. So one is like say that I um send you an email asking for like your resume or something like how long does it take for you to respond? Say that we do a Zoom call and I say hey oh why don’t you shoot me a text afterwards? I’d love to like, you know, we should connect more closely. So like send me a WhatsApp or iMessage, here’s my phone number, see if they do it like after the call and like how long it takes. Um, and like we like people who are very proactive. So it’s like, oh, like if you read something interesting like let me know if you, you know, see any interesting news next week about, you know, AI or tech. Um and then sometimes also like if you provide options for like uh scheduling a call, you know, I can provide some options that are weekdays, provide some options that are weekends, provide some options that are like later nights. And so I get a sense of like, oh, does this person are they willing to do a call on the weekend? Are they willing to do a call late at night? Um like are they willing to push like that that they’re willing to do work outside of like regular business hours? because you know if you’re doing a startup or you’re starting a startup fund like you want someone who’s willing to put in the effort not just during like a 9 to5 Monday through Friday right um so it’s like a lot of these like small things that I honestly look for that may not be the most conventional questions yeah I like those all of those tips one you said about trial uh trial work that’s something that I’ve also learned kind of the hard way of like working with people letting them go and that’s what I actually try to do now with all the people I work with as well. And then the competitiveness responsiveness thing. Um, you know, honestly, mostly a lot of times I guess like maybe in your field you do, but the whole competitiveness, it’s almost the opposite of what people kind of openly talk about nowadays cuz I feel like a lot of conversation has gone more towards good work life balance, like work is not everything, etc., etc. But then I I guess like both of us have a banking background where it’s like we’re mo we’re the type of people who would think about that a little less than like let’s say the average person. Um but um I think that was like super interesting actually to to hear how how you think about that. Um the the last question I had for you was uh the question I always ask at the end which is you know there’s a lot of people who are listening or watching to this who are going to be in college and um if you could speak to your younger self and kind of give young Kevin some advice like what would you say to him? Yeah. No, it’s a really good question. Um it’s been a while since I think I’ve been asked that question but I used to get asked it a lot actually. Um, I think the main thing I would say is try a lot of different things that you’re interested in and try to figure out as fast as possible what you want to do. Um because for me, I think the faster that you get to what it is that you’re I don’t want to say like everyone is meant to do like one thing, but I do think people all have different strengths and weaknesses and things that they’re they’re good at, things that they like, things that they don’t like. And the faster that you can figure it out, the faster you will be in a position or in a role where you are destined or best set up to succeed. Um, I think a lot of people kind of follow the path of like, oh, I’m going to do banking. I’m going to do private equity. I’m going to join a hedge fund. Like, you know, especially probably a lot of your listeners, they they may fall in this category of this is the path. Um, and I think that’s fine to a certain degree. Um, but at each step of the path that you take, try to like be introspective and think about, am I good at this? Do I enjoy this? Because at some point you will have to make a decision that like if you don’t enjoy this and you’re not good at it, you probably should do something else because either someone’s going to tell you like the the outside world is going to force it upon you to like do something else or you will feel so unhappy and unfulfilled that you will have to do you will decide yourself to do something else. And the earlier that you get to that realization and hopefully try to figure out what it is you are I don’t want to use the word destined but like more like fit to do like what is a good fit for you I think the sooner you will hopefully you know take off to the moon and actually be really successful in what you do because if I think if I had started out if somehow I had figured out that I wanted to do venture capital and and you know this type of investing straight out of college. You know, I think you know there there would be so much more time that I could have and opportunities that I could have invested in like some of the companies that unfortunately like at the point in my career it was already too late for, right? Like um I think like you know Uber for example was probably one that if I had found out earlier I could have you know if I was in a VC role earlier I might have been able to like get into companies like that. Um like Stripe and things like that. Like there are a lot of companies where the the time the window of time is just very fast and things move very quickly. And so the faster you get to what it is that you really are I don’t know meant for doing I think that’s like a huge advantage. And if you can just trial and error, test a bunch of different things, do a bunch of internships, you know, bounce around. I think it’s completely fine when you’re young, like no one’s going to hold it against you if you spent like 6 months here and another 6 months there. Um, I think that is probably the advice I would give to like try to find your forever home fast. Yeah, I mean, I would echo that a lot as well, having tried a bunch of different things over the past uh decade for myself. Um, I guess we’ll uh we’ll leave it leave it there. Um, thank you so much, Kevin, for spending this time. I’m sure you have a lot of people to meet and uh people to speak with and you’re you’re you’re quite busy. So, I appreciate you making the time and I’m sure everyone who’s listened also um gained a lot from the myriad of different experiences you’ve had over the past uh since college basically. No, thank you so much, Ben, for having me on. like uh you know again I have a ton of respect for this platform that you built and super excited to be able to get on here and talk to all your listeners. Um and hopefully we can do it again sometime in the future too. Yeah, sounds good. Thanks so much, Kevin. All righty. Take care. See you. Bye. All right, so that concludes the episode with Kevin. I actually try to keep these episodes to 1 hour, but there was so much to talk about and I feel like we just barely scratched the surface. Let me know in the comments if you enjoyed this episode. And with that, thank you all so much as always for tuning in and hope to catch you in the next one.