00:00:02 Speaker 1: Bloomberg Audio Studios, Podcasts, radio News. This week on the podcast My Somewhat Special Guest, Jack Rains is a venture capitalist and author. I've been reading a substack for a couple of years and always found it quite entertaining and interesting. His new book Young Money, A field Guide to Wealth and Purpose in your twenties, is really interesting and wise beyond its years. I wish I had access to a book like this one hundred years ago when I was in my twenties. I thought this conversation was fascinating. I think you will also, with no further ado, my interview of Jack Rains. Jack Rains, Welcome to Bloomberg. 00:00:52 Speaker 2: I mean, the extra special guest is way too kind, but so my special guest, my normally special guest. 00:00:58 Speaker 1: I wouldn't want to call him like my young guest. My you know, I painted myself into the corner with extra special guests. Why once you go that way, you can never go back. 00:01:08 Speaker 2: I'll take it. 00:01:09 Speaker 1: Here's my special guest. Really, what's wrong with Jack? He's a special were a cowboy hat? That's right. Well we'll get into that a little bit. So let's roll back so many years ago to when you're undergraduate studying finance in Spanish while playing football and mercer. That was before you got your MBA from Columbia. Was there ever a career plan? 00:01:32 Speaker 2: Like, not really, it was just I don't know. I feel like basically every white dude ends up studying finance unless they're dead set on going to like med school, law school, or like computer science. So it was study finance, and then I was set to graduate in two and a half years because we had to take summer classes with football, and I was like, I should double major finance and marketing is stupid. I don't like computer science. Let's pick up Spanish because it feels like that could be marginally used living in the South. Spanish is very assiassi right now, but it's like sufficient. There was no real career path other than figure it out from there. 00:02:11 Speaker 1: That's intriguing. I'm cracking up because they have so many different ways to go with this. First gig out of school was a corporate finance at UPS, which you described as mostly moving a mouse around the screen and trying to look busy. Correct tell us about your experience in corporate finance. 00:02:33 Speaker 2: Yeah, I mean to set the stage a little bit. I graduated in December twenty nineteen, which was probably the worst possible date to graduate, given that COVID started like three weeks after that. So I moved to Atlanta in January or February of twenty twenty start working for UPS. I'm in the office for three days, my computer isn't even fully online yet, and then we're told that we're going remote for one week and then one month, and then everybody had the same experience where a year and a half later you're still remote. So I don't think it's great to be a twenty two year old who's never had a real job who's then told you're going to work from home while you have like your Xbox and all of your friends like doing the same thing. And it was actually like a terrible environment to like start learning how to be a worker. And yeah, it was just zoom calls, Excel sheets like modeling out fuel cost projections and forecast for UPS for like twenty twenty two. Yeah, I was honestly bored the whole time. And to build on top of that, I had gotten to business school out of undergrad so like Columbia, I went to business school at Columbia, and they have a deferred enrollment program where when you're a senior in college, you apply and then you work a few years and go to business school. So I knew that I was going to go to grad school in like three years. Covid hit. I was super bored working remote, just doing basically nothing, and it just kind of felt like I was in a work from home purgatory for about eighteen months. 00:03:57 Speaker 1: So having that window where, hey, I know where I'm going to be eighteen months from now in September of twenty twenty blank, what led you to say, I think I'm going to quit and just buy a one way ticket to Barcelona and travel the world. Like that's a giant leap, which not a lot of people have the nerve to make. What led to that decision? 00:04:23 Speaker 2: So, Like, when I was a kid, I always loved to travel, and my grandparents would take me everywhere. 00:04:29 Speaker 1: Your grandma took you on a crazy trip you described in the book to Savannah in Africa. 00:04:34 Speaker 2: Yeah. Yeah, when I was eleven, my grandma Mama roof, she I'm the oldest grandkid in the family, and she hit me with the idea that she wanted to take me on a trip like anywhere in the world I wanted to go. I actually didn't know if she literally met anywhere. I wanted to go, somewhere crazy, like Africa or Asia. And we lived in South Georgia. Initially I pitched Costa Rica and she said, too, you can. Yeah, she said, like, that's like a three hour flight. I was like, okay, Like I thought the like I had a big map in my room as a kid, I thought it'd be cool to go to the Ngoragora Crater and see Mount Kilimanjarro and all this stuff. So she took me and we went, and we went on a two week safari and it was awesome. And then in college I studied abroad in Spain. One summer, I went to France. One summer with my best friend from college, I did a service trip to Ecuador. Like I always loved leaving the US, and it was kind of a thing in the back of my head where I knew, at some point in my twenties it would be really fun to do like a multi month trip abroad with like no itinerary other than just see other stuff. And I was sitting there, It's like you have this, You're working remote for eighteen months on your board, and then I, for better or worse, had a fortuitous run trading spacks and spack warrants during the pandemic, which gave me enough. It gave me more money than I expected to have at twenty three or twenty four, where I was like, I mean, I I don't it wouldn't cost that much to just go hostile hop Europe in Latin America for a year. 00:05:58 Speaker 1: Yeah, I'm glad you were up. You're not a trust fund budd it, but baby, in any stretch of the imagination, no, you scrape together some money, you fly coach, you staying in hostels. You have ten roommates in these. 00:06:11 Speaker 2: Places, eating like McDonald's or Euros or whatever. Every day. It was the best. I mean, I got food poisoning oneside, It was fun. It was fun. 00:06:19 Speaker 1: The more recently, you wrote a story about going to someone's winning and I think it was India and a bunch of people got food poisoning and it was hilarious. 00:06:29 Speaker 2: It feels a little bit like India right now in New York. It's like the air quality today as of recording is pretty similar. 00:06:34 Speaker 1: To those Canadian fires. Are you walk out, it smells like a bar because it's yellow. 00:06:40 Speaker 2: It's like for microdosing New Deli era. Right now, it's great, it's good stuff. 00:06:44 Speaker 1: Only without the e coli that you described. But let's bring it back to your career. So, so you do this trip, you go through a couple of dozen countries, you meet people that you're still friendly with. It was really fascinating, and you get to business school. How do you adjust? How do you make that transition? 00:07:06 Speaker 2: Yeah? It was. It was interesting. Like I in the back of my head, I kind of knew I had this start date moving to New York in August twenty twenty two. So I eventually quit my previous job, first job out of college in August twenty one. It was kind of like, all right, let's spend a year and just have as much fun as physically possible, knowing that then we're gonna go to grad school. Then we'll do our career in New York and YadA, YadA, YadA. It was funny because it was at first weird, like being like I spent basically a full year out of the country, jumping around a lot, and then you're in New York and you have like a home base and you have a business school. Is not a particularly strenuous thing, but you do have a set schedule where you have classes and stuff. I loved it though, I mean, I love Columbia, honestly, I love New York in general, best city in the world, particularly in your twenties. And it took a couple of months to really get in the flow of like living here and then also like you're meeting hundreds of new people like that, but actually getting integrated not hard. It felt like a perfect. 00:08:06 Speaker 1: Fit, really really interesting. So I'm curious. You learn a lot of things in both your office career or remote work from home career and business school. What did you learn about finance, money time while you were traveling. 00:08:25 Speaker 2: I mean, the biggest thing that really jumped out was It's something I write about a lot in the book, like the I call it the stage specificity of life. But by that I mean that it's pretty easy to conceptualize money, like what you're taught from like in high school, how money compounds over time if you invest in and it's you know, you should be frugal and save up money, but what you miss is like what's the optimal time to spend that money on different things? And the example that I give a lot is like I was twenty four and like sleeping in a bunk bed in the hostel with twelve roommates or whatever, and it was actually just a hilarious setup. Like it's just a bunch of nonsense. You have a French guy here and then like a Mexican girl here, and it's like half the a lot of the dorms are co ed, and it's like it's like summer camp for like young adults. But then occasionally you meet somebody in their like early thirties staying in the same hostel and it's like you can almost tell that they noticed they're like probably six or seven years too late to have done that type of trip. And like the biggest takeaway from traveling was like if I really wanted to do this trip, this was the like this was the right window to do this. Like I optimized like that phase of my life correctly for somebody who wanted to do that type of thing. And that's kind of what stuck with me the most after is not just being aware of what you want to get out of life, but like what things have deadlines, where like if that window of opportunity closes, you're just not gonna be able to maximize your like fulfillment or enjoyment or utility from that experience. Like every basically everything you do in life has an expiration date for when you would enjoy the most you can. 00:10:00 Speaker 1: You can go cheap and cheerful in your twenties, maybe even early thirties, but not much past. Correct, So you were also writing before the trip and during the trip. Tell us a little bit about your experience, what you discovered about yourself as you're writing, and why you thought that might be a career path. 00:10:18 Speaker 2: So like, Hilariously, when I was doing the whole spac trading thing in twenty twenty and twenty twenty one, I had a burner Reddit account called Barmelo's Anthony. It's a play on words on Barmelo, Carmelo, Anthony, and xanax bars. It was my name of my college group me. We all had edgy like drug related famous person combination names. I was writing so much stuff about, Like, oh, like Apollo changed the background header of their website from oil rigs to windmills. I think they're going to take an ev company public through a spack And then they announced a deal with Fiscarado motive. Three weeks later it was like borderline conspiracy theory stuff, but it worked a lot of it worked. Yeah, So I like always liked just writing about like stuff I was seeing going on in markets. And then when I was when I was traveling, I tried to get hired by The Morning Brew, the Hustle, a few different like kind of upstart ish media companies. Nobody would hire me for lack of like professional writing experience. So I just started writing, like I just launched a sub stack and started writing a newsletter. And it was like half investing in finance and half travel blog, like detailing everything I was doing day to day, who I was meeting, and I just enjoyed it, Like it's writing something I've always found fun. I've always found it a bit cathartic, like putting your thoughts on paper, and it's a good I don't know, I think it's like a good exercise for anybody to really like distill what you think about a thing is try to sit down and put pin on paper. 00:11:44 Speaker 1: So Daniel Borston, the Librarian to Congress is famous quote, I write to figure out what I think. 00:11:51 Speaker 2: Yep. 00:11:51 Speaker 1: And besides, at that hour, the bars were all closed. 00:11:54 Speaker 2: Yep. 00:11:55 Speaker 1: So you know, until you put it down, until you put pen to paper, a finger to keyboard, it's sort of nebulous and not distinct. Once you write it there it is black and white. Yeah. Yeah, so for sure. So you come out of Columbia, what's the first gig you're doing while you're while you're a new grad. 00:12:16 Speaker 2: So, so to step back a little bit, when I was still in business school, I kind of had this like, I think investing in financial markets are interesting. I really like writing. I had like monetize my newsletter fairly well selling ads, and I was kind of trying to figure out which way I wanted to lean with it. And then I had some publishers who were like loosely interested in me maybe writing a book. So I wanted to leave the book writing door open. And I interned for a venture capital fund called Red Point Ventures my first year, helping them with like building up a newsletter and like editorial strategy and all that stuff. It was like love the team there, it was great. My takeaway from that was I should either like go do media or I should like push you get in like investing seat somewhere, not split the middle and do like the marketing arm of an investment group. So going into my second year, Sam Row, you know, Front of the Show. He was like contracted by Robin Hood to help them with the hiring for they were building out a media subsidiary called Sherwood News. We grabbed coffee and he was like, I don't know what your plan is after business school. I think you'd be a good fit with what they're building here. And he started telling me about it, and it checked a lot of boxes of like, on one hand, it was kind of an upstart new media thing with like I would have a lot of autonomy. On the other hand, we were surrounded by the structure of like a big fintech company, so, like media is a tough business these days, and there was a lot more stability there from like financial backing. 00:13:43 Speaker 1: Tell me about having a media outlet attached to a large fintech or data services company. 00:13:50 Speaker 2: The entire pitch was just trying to like basically make a new Age Bloomberg tell you the truth. 00:13:54 Speaker 1: Did you guys get any hood stock? 00:13:57 Speaker 2: Yeah? Yeah, yeah, so not. 00:13:59 Speaker 1: Terrible, not terrible. 00:14:00 Speaker 2: I mean the issue was I only worked there for a year, so it's not like I got that much but like it. Yeah, like I wish I would have I wish I would have gotten more, and I wish I would have stayed longer had I gotten more, is the takeaway from that. But yeah, I ended up ended up joining them during my second year. I signed the book deal for that book the summer after I graduated. It's about two years ago now, and then I was sitting there and I just like everything was fine. But I realized after working in a like more structured media environment, I actually like like I like writing a blog. I like kind of free range putting stuff on the internet, but like I didn't like the actual like like call it nine to five employed version of like financial media, and my like it kind of clicked to my head that when I was at that point of investing thing versus like media, I actually probably should have gone investing track, but I was so hyper focused on like I don't want to kill a potential book deal momentum and this and that that I took the other one and I had like a total career panic, like to almost too most two years ago, like fall twenty four. 00:15:02 Speaker 1: And there is something to be said about the daily beast that must be fed when you're on a regular deadline, Like that's tough. Yeah, no, it's brutal. And it's why there's so much content that's so useless, because hey, there are minutes and hours to fill in column inches and the infinite more of the Internet. I mean, it just never stops. So that's why we have this fire hose. So, so you had done Young Money as a sub stack, you had done Sherwood for Robinhood. I'm kind of fast anybody in an essay you did how I lost one hundred and fifty thousand dollars in a day trading SPACs yep way back in twenty one. Tell us about your ramp up in the spac world and then the blow up. 00:15:50 Speaker 2: Oh it was, I mean it was awesome, like like I like I was. I don't know if you would have checked my pulse or stress levels at that point they were through the roof, but like it was crazy. So it's like, right when the pandemic hit, I thought I was like the next Michael Burry. I had like ten thousand dollars in my checking account, threw it all in spy puts. They tripled because obviously the market was going to take and I was like, yeah, I'm him, and then you know Bill Ackman. A week later, it was like crying on CNBC say the world's going to hell, and I was like, SMP's going to like a thousand, let's do it again, let's buy more puts. You know, I actually, having not really been an adult during eight I completely underestimated like the FED and quantitative easy. 00:16:32 Speaker 1: And how that could work and how fast that turn is. 00:16:35 Speaker 2: Like I my face got melted off. I shortened the actual bottom and then I basically round tripped ten thousand dollars to thirty back to ten. I have my tailtop between my legs and I was like, I'm never trading a stock. 00:16:45 Speaker 1: Did you ever feel the need to reach over to the waste paper basket and throw up? No? 00:16:50 Speaker 2: But like if it had been bigger numbers, maybe, so I'm like, I'm never going to trade stocks again. I put six thousand dollars in. I opened like a roth Ira do my one contribution first years a you know, adult working, and I don't look at it for a month. And then in May my friend Jake Buddy from undergrad was like, do you know what a spack is? I say no, and he's like, well, if you buy this Desert Eagle spack, It'll turn into DraftKings stock in like two months. And I was like, it's like like an ipo, and he's like, I don't know, dude, I just saw on the internet. If I buy this, you owned Draft Kings. And I was like, okay, I went now the rabbit hole was looking at it, and it's like. 00:17:26 Speaker 1: And it's a pars. It's before it comes out. It was it trading? It was it did trade up. 00:17:32 Speaker 2: It was trading because so the par on most spacks is like ten dollars, and it was trading at like twelve or thirteen. Oh really maybe fifteen. But the warrants had like doubled or tripled, right, because all the warrants have a strike price of eleven fifty. So then I had like traded options enough. I understood like strike prices, expiration dates, whatever. And the thing that jumps out was that warrants don't expire for five years and they have an eleven fifty strike price. So I was doing the math and I watched DraftKings. After the merger happened, it ran out to the warrants ran up to eight or nine dollars. You would have doubled on the stock. We would have made like nine x on the warrants if you bought them at a dollar, like at peak pandemic collapse. 00:18:09 Speaker 1: So I was like, okay, if like this is easy, well, I was. 00:18:13 Speaker 2: Just like spacks obviously kind of seemed like a bubble right now, because there'd been like Nikolai Motors had announce a Spack and there were a couple of others, and I was just like, I bet that this thing is gonna like this is just gonna be a game for a little while. And if I can just pick the spack warrants early, I bet I can make money. So Nicola warrants to trade at three dollars, I bought six thousand dollars worth. I made like twelve grand a couple weeks later, and then I just kept rinting and repeating spack warrants, and like six months later, I got from six grand to one hundred and fifty grand, and I was like, this is so easy. 00:18:42 Speaker 1: So then I, by the way, oh that that should immediately set bells off. 00:18:48 Speaker 2: I doubled down, though it didn't set off any bells, because then I was like, okay, it did set off one bell. I was like, warrants are risky, and if any of these deals collapses, the warrants go to zero, I should start buying the shares close to NAV as possible. So I was in like an online discord chat with a lot of other anonymous people. We built some web scrapers that will pull every spac SEC filing, so as soon as the filing hit the press, like trading halts, when news comes out for a spec, I would get a push notification, open up the deck, skim it. If it was electric vehicles, marijuana, outer space, sports, betting, or renewable energy, I would go all in unless the unless the like valuation of the deal was just egregious, I would go all in. And I knew that the stock would probably pop like at least thirty or forty percent, because they just did every time. So you get in an eleven, your max loss is probably like five percent on any trade, and you sell it fourteen or fifteen, so you're basically risking five percent to make forty percent. 00:19:47 Speaker 1: Of asymmetrical risk reward. That's what you want. 00:19:49 Speaker 2: And I did that like seven times in a row, and then I went from one fifty to four hundred and like I'd only risked on any given trade, like five percent of my portfolio, and they didn't all hit, but like enough did that it didn't matter. And my dad, obviously, I kept telling him what I was doing, and I hit like it was February twenty twenty one, and he called me and he was like, you should probably just sell and just put it in like an index fund. And I was like, I knew this two more times, I'll have a million dollars at twenty four. I'm pretty sure I can get there. That should have been the. 00:20:17 Speaker 1: Screen is the bell ringing that? 00:20:19 Speaker 2: And then when he and his brother were talking to me about potentially managing some of our family's money. You shouldn't have your twenty four year old kid, he just made six thousand percent trading spacks, touching your grandparents like retirement money. I did not, thankfully. I said, I don't feel comfortable doing that. I'm okay. I was self aware enough to know that would have been a bad idea. So getting to how I lose the money at this point, way too many spacks. Shaquille O'Neil has a spack, Paul Ryan has a spack. Like everybody and their mother has a spack and the bubble didn't pop. It just stopped bubbling because there there was kind of this pool of money that was chasing every hot spack and then there's like one hundred of them on the market. Somebody announce is a deal, the terms are getting worse and worse, and the value. 00:20:58 Speaker 1: You're watching this to k in real time. 00:21:00 Speaker 2: Yeah, And it was like by April May of that year, it's getting tougher and like a deal would get announced might jump ten percent. You're just I was like I was addicted to the rush. So there was a buy now, pay later company called Catapult. Eighty percent of the revenue came from Wayfair, obviously a pandemic darling. And this is at the time when Square bought After Pay for like thirty billion dollars crazy price. A firm went public at like a thirty billion dollar valuation, and like these companies were growing slower than Catapult because Catapult was just a derivative of Wayfair, which is a pandemic darling. They were less profitable and I was just like, Catapult's gonna have their earnings in August. They've had no cell side coverage. I just need like one analyst from like Morgan Stanley or whatever to initiate like a buy the stock's gonna double, I'm gonna buy a bunch of warrants at like a dollar fifty they're gonna rip. And then this thing, like I'm gonna make a million dollars on this trade. This thing had already gone public through a spac, Like there was no floor, that deal was closed. It's just a normal company. 00:21:57 Speaker 1: So not your traditional spac trades that you've been doing. 00:22:01 Speaker 2: It had gone public through a spack and it's just like a normal company at this point. And I I just aped into it with like three hundred I think I had like three hundred and thirty thousand dollars at that point. Just went all in and it started like inching down and spike back up leading up to earnings, like I had four different times I could have gone out with like a ten percent loss, and I was just like I was just pot committed to, like this is gonna be the millionaire trade. They missed earning so badly that the stock fell. I think the stock fell twenty percent before market opened on like August eleventh, and the warrants immediately got cut in half by like fifty. 00:22:33 Speaker 1: Percent and that's one hundred and fifty grand. 00:22:35 Speaker 2: Yeah, and I'm just I'm looking at it. I'm looking at the like level two trading data, and there's there's a big buy for like like one hundred thousand warrants at a dollar or whatever, and then there's the floor collapses under and I was like, huh, I'm just gonna like, I'm just gonna sell to that entire bit and just eat it, and like I'm getting out before like the whole thing that's rug pulled, which was the right move because I basically liquidated my position pre market from like three hundred thousand dollars like one hundred and fifty or whatever. And I was just like, man, that sucks, put in the SMP, and then just went to the gym and worked out for like real self loathing workout for three hours. 00:23:12 Speaker 1: You know that that sort of big wackage is a rite of passage of anybody that's ever worked on a trading desk. I don't care if you're at you're at Jane Street or if you're day trading from home. Those losses are just so seminal and so instructive and focus you on, Hey, what's my risk management. What's my edge here? What am I really doing? Swing for the fences? Am I really putting fifty or one hundred percent of my portfolio into one trade? That seems kind of like you you you could read that in a book, but until you've lived it, it's really challenging. 00:23:47 Speaker 2: The issue for me was like the plan I had initially of like buy spacks near navs, sell when they pomp, was like a good strategy. And if I'd stuck with that, even if it stopped working, it's like, Okay. 00:23:58 Speaker 1: The down side is the minimus, we made. 00:24:00 Speaker 2: A bunch of money, this trade doesn't work, just like parking index fund until any right, yeah, and then like either come up with something new or just stop. The issue was I was so used to number going up. I was kind of willing to bet the house I'm doing it one more time, then I'm confident I hit a million. I would have walked away like that was just like a benchmark numbers. 00:24:17 Speaker 1: Oh you should know that when you hit, you would not have whiked away. Junkies don't say one more hit, and gamblers don't say, I just need this parlay to come in and then I'm good because you're always looking for the for the dopamine, hit for the adrenaline. 00:24:33 Speaker 2: I would have found something else to speculate on. But I think I would have stopped trading SPACs had that happened. 00:24:38 Speaker 1: Coming up, we continue our conversation with Jack Rains, discussing Slow Ventures and investing in creators. I'm Barry rid Halts. You're listening to Masters in Business on Bloomberg Radio. I'm Barry Ridults. You're listening to Masters in Business on Bloomberg Radio. My uh, somewhat special guests. Is that how you want to be? Is that how you described it? Said? 00:25:02 Speaker 2: Marginally special? 00:25:03 Speaker 1: My marginally special guest, Jack Rains is here. He is an associate at the venture capital firm Slow Ventures and the author of the book Young Money, which we'll get to in a few minutes. So I'm kind of fascinated how you pivoted into VC work. You joined Slow Ventures in San Francisco from New York. Did you relocate to San Francisco and then come back to New York? So I kind of get this venture by coastal. 00:25:33 Speaker 2: I try to. I try to. I try to make it look by coastal occasionally on Twitter. No, I mean The funny thing was they were hiring in New York and San Francisco, and I applied for the New York job, and met was the partner in New York first, and then the one of the gps in San Francisco, Sam Lesson. I get introduced to him by the guy in New York and we're on a zoom call. He'd like, just come from the gym, super sweaty and like shoveled looking, and five minutes you all to say that. 00:26:00 Speaker 1: I'm okay with that. 00:26:00 Speaker 2: I think he would agree with it. Five minutes, five minutes out of the call, he's like, what do you think of San Francisco? And I said fentannel and homeless people, and he was like, it's a crazy ass for somebody applying to a job in San Francisco. And I was just like, I didn't like I applied for the job in New York and he was just kind of like, well, I thought I was interviewing you for an SF seat, and I was just like he told me to like take a beat and like think about it. And I can't rememer if I told him on the collar. Just texted him right after, but I was like honestly, dude, I mean, I want the job, so I didn't know this is what I was applying for. But if you hire me, I'll move to San Francisco. And he was like, have you ever visited? And I said no, so. 00:26:38 Speaker 1: But I've been to twenty five other countries in fifty other cities. I'm sure I can figure it out. 00:26:43 Speaker 2: Yeah. The only difference to San Francisco has so many more AI startup advertisements on the billboards and the way mos, which are awesome. But yeah, like I I mean I. 00:26:52 Speaker 1: And they are everywhere. We were just San Francisco a few months ago. 00:26:56 Speaker 2: They're so sick. 00:26:57 Speaker 1: They they're like yellow cabs in New York. 00:26:59 Speaker 2: Yeah, yeah, they're They're incredible. I mean the worst thing about New York is that we keep trying to like block way Moos. Let it happen. I'm I'm so pro Weemo. I'm like Waymo's biggest fanboy. But yeah, like, going back to Fall twenty twenty four, I was in this real like kind of career panic. I want to get out of media, and like I was like I should have gone down the investing route, and then you know it's like a step back and I had like signed that book deal. I was like, Okay, I'm gonna have to write a book. I'm gonna have to be able to market it. So that means I need to look at jobs where I could still have like bandwidth and flexibility to do so, which like eliminates a lot of investing ease stuff where there's compliance issues. 00:27:35 Speaker 1: No investment banking, no no trading on a desk, and no portfolio management or even CFA analysts where whatever you do is disclosable and requires approval and it's complex. 00:27:50 Speaker 2: But venture capital is like the biggest, like build your personal brand, like content helps you source deals. So I kind of honed in on and I didn't have like an investment banking back ground. VC is more open to non traditional investing backgrounds. It just kind of made sense. And I had a decent network in that space from like Twitter and riding and all this stuff. So I just kind of started pounding the pavement, like reaching out to vcs. I knew of my network that may or may not be hiring, and Slow happened to be hiring, and I messaged hilariously. I messaged Yoni, the partner of New York on Blue Sky, that was back when everybody I thought Twitter was going to die and blue Sky was Blue. 00:28:24 Speaker 1: Sky didn't take off. But it does feel like Twitter is kind of ground to a shell. 00:28:29 Speaker 2: Of what it. I think it's starting to come back as of like a month ago. Oh really, it feels like they changed the algorithm where you can like see your mutuals again, so people literally last week Nikita Beer tweeted, they tweet the algo so like you're seeing your mutual followers and I was like, dude, that's what it should have been the whole time. But anyway, I basically got hired from a Twitter DM and then a last second flight to San Francisco six weeks. 00:28:53 Speaker 1: From application to starting in SF. 00:28:56 Speaker 2: Basically like I didn't know where to live. Facebook Marketplace, found some dude with an open room and just hopped on a FaceTime with him, and I was just like, yeah, like, I guess I'll just take the other half of your apartment. And then I moved there. That was I just put my stuff in a in a suitcase and just flew out. 00:29:12 Speaker 1: So are you New York based? 00:29:13 Speaker 2: I live in New York now. I moved back here a few months ago, all. 00:29:16 Speaker 1: Right, And and how do you how do you work that out if your core office is San Francisco. 00:29:22 Speaker 2: So we have an office in New York too, Flat Iron, so twentieth and fifth. It was one of those things where we were pretty a sync in San Francisco, like we have an office in downtown SF. I was going in probably four days a week, so like some people were going in a lot. My boss lived in the suburbs a little bit. He would come up sometimes, but I would like take the cowtrain down to like the Hillsbo area and like go to his place. So I work from his poolhouse with him. It was a funny setup, but it was like we were a sync enough. And I also knew that like long term, I was gonna want to live in New York. I just pitched them on moving back and then flying out to San Francisco like every three weeks or so, and that it's the setup I have now. 00:30:01 Speaker 1: That New York has a pretty robust technology sets there. I mean, we all think of San Francisco for AI computer mobile tech and Boston for healthcare teche. Where does New York land in that in that list? 00:30:17 Speaker 2: It's it's increasing I would I would put in New York is the. 00:30:20 Speaker 1: Like pretty fast rising right on for. 00:30:22 Speaker 2: Like consumer tech. I would argue it's like number one or close to it. 00:30:26 Speaker 1: And then you've got a big Google office here, You've got a big Microsoft office here. You've got a giant Amazon office here. 00:30:31 Speaker 2: Well, and like Anthropics opening like a sixteen thousand square foot like they're opening a massive office in Hudson Square. 00:30:38 Speaker 1: Like you there's some space there. 00:30:39 Speaker 2: A lot of like a lot of a lot of what keeps happening is like all these AI companies start there and then as they move into like bigger and bigger, like enterprise commercial business, they expand to the East coast, and like there's a lot of like sales teams on the East coast and engineering town on the west coast. New York's also like a more social, outgoing city where a lot of the like like sales and go to market people would prefer to live here. San Francisco is more insular, and it's like, uh, there's just engineering talent from like Stanford, Berkeley, whatever. It aggregates around the Bay. So it's it's honestly a big part of like engineers end up on the West coast, and then a lot of the sales people end up on the East coast. A lot of the customers are also on the East coast. 00:31:17 Speaker 1: So really interesting. All right, So I got to start with a few quotes of yours and we'll plow through a lot of that. One of the things though, that that you said a quote of yours, junior investing jobs at VC megafunds are really just cold calling. Yeah, I don't think of VC in those terms. Explain are you really just smiling and dialing. 00:31:43 Speaker 2: Like a little bit. It's funny, Like I don't know if you read Bill Gurley's new book, Run It Out of Dream, so he said something similar with a venture capital is ninety percent sales, and it really is. 00:31:52 Speaker 1: Like, but that's true about everything in fine Yeah, it's really and I don't know about outside, but everything in this space is you're ultimately asking someone to trust you and give you their business. 00:32:03 Speaker 2: Yep, yep, yep. VC, especially at the big like it's like Slow is a fairly small fund, right, Like we have like total teams like fifteen or sixteen people, investment teams like nine or ten people. But like some of the bigger funds, like I have some bodies that have worked at the like call it some combination of like the general catalyst type A sixteen Z type whatever. It's just a machine or like inside is like this too, or like you are managing just like tens of billions of dollars or whatever, and there's so much coverage that it's I was a little tongue in cheek saying that it's like cold calling, but it is very much like you need to be talking to like X number of people, and there's like metric hurdles on like touch points and stuff. It's like it's not that there's no discernment or anything like that, but it's a volume game and. 00:32:51 Speaker 1: They try and quantify it and turn it into. 00:32:55 Speaker 2: Yeah, it's like you the name of the game is you don't want to miss anything that could be something. Therefore, like people should be pounding the pavement making touch points with anybody who could be starting an early stage tech company. 00:33:06 Speaker 1: Now, Slow Ventures kind of famously avoids the trendy hot stuff. No robots, no AI foundation models, What are you looking at at work? That's kind of interesting. What do you guys get to see that most people are overlooking? 00:33:23 Speaker 2: So it's funny. We actually we actually just announced one that's like robot e doing like like warehouses and fulfillment for e commerce companies called Sutronic, So we do occasionally touch they don't make You'm right right, We're not doing any of the stuff that it's cloud on Twitter because we can't fold, close or do dishes, right. I mean it's we're like broadly generalists. We've done everything from like we've done just to name some companies over the last ten or twelve years, like Robinhood, Slack, all Birds before they pivoted to being an AI GPU company back when they sold footwear. I mean, we have like a hilarious one meme, Lord's Technology where it's basically a software platform. It's like a basically marketing tool platform, but for creating memes. I mean, we'll do a little bit of everything we've done. Crypto stuff we've done. We have done some like vertical AI stuff. We just like making our calling card. We're not chasing the AI hype. The way that we broadly think about it is there's a lot of VC deals that are trades that are now marked up a lot, but like do they have terminal value in what they get supported in public markets? You don't know? And a lot of early stage investors that have played those and then sold when bigger funds come in at the multi billion dollar evaluations. It made a lot of money. So like you could argue we should have played that trading game. The bet that we're making is like, go for the stuff that's going to compound long term value, that could be like a standalone valuable entity. 00:34:50 Speaker 1: How does the sort of dearth of IPOs, although we're in the middle of a period where there are suddenly a spate of them coming out and more more companies choosing to stay private for longer, how does that figure into the VC calculus of Hey, we eventually want an exit and we can't rely on someone else, either from a big affirm taking this over or some M and A to give us an exit. 00:35:16 Speaker 2: It's interesting. I almost think you have to put VC in two buckets at this point, where you have like we play at the really early stage, which also gives you like a lot more opportunities for exits, whether you sell steakes to like a later stage bigger growth like a bigger growth investor once they're in the unicorn status, or you get the acquisition or IPO if you're getting at a company that's worth twenty or thirty million dollars. There's just like a lot of ways you can get paid on that. Versus you have companies like like Thrive is probably the most famous one where they manage like fifty billion dollars now they own a massive slug of open ai, Like they take really big bets in companies that are like it's worth ten billion or one hundred billion, we think it can be worth a hundred billion or a trillion. So for us, we have a lot more flexibility on exits, which is like good because we can be more nimble. 00:36:02 Speaker 1: You're primarily seed in A rounds, but you're not doing B rounds, or. 00:36:07 Speaker 2: We occasionally will with follow on capital, but it's like ninety five percent seed in A So that's like that's our sweet spot. And then so I think for funds like that, I think people like a lot of early stage funds should get more creative. Where can you exit into a big growth fund coming in at like a five billion dollar valuation from portfolio construction? Maybe you should With the megafunds, it's like, okay, if you're going to do that, you can't really index all of the like five or ten billion dollar unicorns because a lot of those those paper marks would never get support in the public markets. But like Thrive going really deep on open Ai or Spark Capital going really deep on Anthropic, those are going to go out at potentially trillion dollar valuations. Like the math works. If you invest forty billion dollars across a few big funds and something at like a two hundred billion dollars valuation and you get four x or five x, you're returning like tens of billions of dollars. Right, So it's like in the early stage should probably be looking to sell, and some some of those later stage companies coming in at the later stage, it's like stock picking. You're basically running. You have to run a concentrated book of like there might be three or four private companies at any time, like a SpaceX, Open Ai and Thropic that could go out at a multi hundred billion dollar valuation. You have to be concentrated in those otherwise the math is going to work. If you get those right, you can like two x three x a fund. If you don't, you want. 00:37:32 Speaker 1: Really kind of interesting you come out of the creator economy. Slow Ventures has been a player in that space. How does how does your experience help you as a VC and what does slow venture see in that space that you know the traditional venture capitalists overlook. 00:37:53 Speaker 2: So to give like a little more color on that we have we have a separate fund we raised a year ago called our Creator Fund, where sixty four million dollars we invest directly in creators, meaning like YouTubers, podcasters, could be newsletter writers. Our bet on that is that like distribution compared to like technical abilities is getting increasingly valuable. Where two things One, it's easier to build stuff like software because of AI coding assistance. Too, the Internet is so loud now that having like a cylinder of trust from your audience gives you a massive selling advantage because it's so much harder to get attention with like paid ads and growth hacks and all this. That we have this and like sam My Boss was kind of came up with this idea a few years ago that like he calls it almost investing in cults. But people who have a true like cult of personality and are a subject matter expert in a particular theme or vertical have a massive advantage on like marketing and selling. So we raised a fund where we literally invest in creators like holding companies where any businesses they build like off their platform, that leverage their brand and platform and all this stuff. 00:39:00 Speaker 1: These are three sixty deals covers everything that person does. 00:39:03 Speaker 2: Yeah. 00:39:04 Speaker 1: Yeah, we basically be a podcast, could be substack, could be all of those. 00:39:07 Speaker 2: Yeah, and like we aren't really that interested in like how money they make from like ad revenue or like platform revenue or whatever. It's more so. For example, the first deal we did was with this woodworking creator named Jonathan Katz Moses, and he has a like he has a massive YouTube channel. 00:39:22 Speaker 1: He's basically I know that just show it is shockingly intriguing watching this guy build stuff from scratch. Yeah, he's like relaxing too. 00:39:32 Speaker 2: Yeah, he's a super compelling guy, incredibly talented, and he's equally good as both a content creator and as an entrepreneur. Like he has a business it's like making like millions of dollars in revenue, and. 00:39:43 Speaker 1: He builds various things and sells them, so he also generates revenue from the YouTube. 00:39:49 Speaker 2: Right, And it's like a specifically has like a tool line called km Tools, and like we invested money into like his holding company, and that can go toward like hiring people to help with like the content development, editing, content creation, so we can like increase velocity of putting out YouTube videos. Also like more people to help rolling out new products and a wider product suite of tools. So the bet is that like you put money in that and maybe like the tool business really blows up and then a like Black and Decker type of company acquires it, or maybe he launches like another business vertical office platform that we have exposure to. So it's but his whole thing is like woodworking, woodworkers. He'll go to like a woodworking festival in Texas, people will come out, like to come like get him to like sign their autographs. Like he he just has a lot of clout in that space. So finding people like that in different verticals that we think have like really compelling opportunities to scale big businesses through that vertical in that audience is like interesting. And historically people have been very hesitant to back creators or they back like one business like mister Beast has a bunch of different businesses. If you back Beast Burgers didn't really work that well. If you were backing mister Beasts as a whole, Like the entire empire is worth like a billion dollars or whatever. So you want to be like a line where if they want to change their focus, like are capital is still aligned with that? Like you don't think this this experiment's working. 00:41:11 Speaker 1: Moved to this one and I think it's called CDC. If you haven't seen these computer controlled woodworking lathes and carves, and they're just astonishing with people Like you think of carpentry as kind of old school, it is not. It's really fascinating. Coming up, we continue our conversation with Jack Rains discussing his new book Young Money, a field guide to wealth and purpose in your twenties. I'm Bury Ridults. You're listening to Masters in Business on Bloomberg Radio. I'm Barry Ridults. You're listening to Masters in Business on Bloomberg Radio. My pretty special guest, my kind of. 00:41:54 Speaker 2: Special, somewhat special. 00:41:56 Speaker 1: Somewhat special guests. I'm want to write that down. My somewhat special guest is Jack Reins. He is a associate at a venture capital firm and a author. I've been subscribed to his sub stack Young Money for I don't know how many years. 00:42:11 Speaker 2: Has that been, around four or five years? 00:42:13 Speaker 1: Let me know when you get to thirty and you'll be onto something. But his new book Young Money, A Field Guide to Wealth and Purpose in your twenties, I was really taken by it. Not only was it a fun read, but I just I not only laughed throughout because I just recognized, oh, I did that dumb thing, but it also is so wise beyond its years. It's hard to imagine that the guy who wrote this was twenty six twenty seven when he wrote it twenty seven, twenty seven, eight last year of your twenties. So I really found it a fun, enjoyable read about a space that I normally don't play in Young Money. And there's so many things to talk about with this, starting with quote I had considered the opportunity cost of how I was spending my time, and I adjusted my life accordingly. So you're giving the whole game away on page thirteen. Yep, you basically say, hey, time is finite, and how and when you spend it is really important. Tell us a little bit about how you reach that insight back when you were in your early in the mid twenties. 00:43:34 Speaker 2: Yes, so, I mean we talked about the spactrading thing earlier, but like when I was twenty three, mainly twenty three, in a little bit twenty four, my life basically looked like this. It was you roll out of bed, throw on some sweatpats, grab Chick fil A for breakfast, and then you're just like kind of responding to like slack messages. You're on zoom calls, spreadsheets, powerpoints, and you're doing all of your bedroom. And it had been like that for well over a year. And then on the side, like you were over here, like you know, training options before we jump on this, I had like my work laptop here, and then I'm my personal laptop here, and it's like, huh interesting, like this spat just got an ounce. So I was I was spending like I was like basically fake working while just trading stocks all day. And then like in the evenings, I you know, you have like your entire net worth and some speculative spack and you're you can't even sleep straights if futures take you think you might lose one hundred thousand dollars. And so I was almost in this like self a news holding cell of like I couldn't go anywhere really because of COVID, and I was stuck at home, and then I was just watching screens all day, and thankfully I made some money from it. But I just became really aware around the time I was about to turn twenty four that I had just spent the whole last year of my life not really doing anything, especially like call it like personal relationships whatever. I was probably a pretty terrible like boyfriend, friend, checked out, son, grandson, like I just wasn't like I was not in control of ho I was spending my time at all. I was kind of like a prisoner to like work and COVID and stock market. 00:45:06 Speaker 1: Which is kind of crazy because during the pandemic, you're no longer commuting, you're no longer on the same schedule. If any of us had a little more prescience, we really could have taken full control of our day. Nobody's looking over your shoulder at what you're doing. You could come and go as you want as long as you got your work done whenever. However, everybody was. 00:45:28 Speaker 2: Fine, which is so I mean to the stock trading thing I did, like that would not have been happening if I was in the office, probably at least not as much. 00:45:36 Speaker 1: But what was fascinating as I was reading this because I started out trading is you. You nailed the phrase you're a prisoner to the screen. You really can't leave your desktop. If you're on a desk, at least someone could watch a position for you. Hey, I gotta go leave for ten minutes. Can you make sure this doesn't blow up on me? If it hits this, get me out? You could do that. But if you're doing this from your bedroom and you have a lot of positions on you, you're you have no other bandwidth for anything else. 00:46:08 Speaker 2: It's just push notifications on for everything. You go to the gym, you're checking your phone every two minutes. It was just like a little bit nauseating, right, and. 00:46:15 Speaker 1: Uh and exhausting. 00:46:16 Speaker 2: Yeah, And like I I honestly just felt pretty like mentally exhausted from the like always being on and I just kind of had enough. And I also found my job pretty unfulfilling, and I knew I was going to leave it in a year, And it was just like all of these things came to a head and I was like, Okay, let's be really intentional here about like how do I want to spend Like if I know I'm going to grad school in a year, like, how do I actually want to spend the next year? Is it keep going in the motions of the job that I know I'm going to leave to go do something else? Is that like like try to like trade back the money I just lost lost on that trade gone wrong? The thing I kind of wanted to do is like, honestly, just go have an adventure having just been cooped up for a year and a half. And yeah, so that like it was just like all of that came to ahead and I was like I should just I mean, it's like the opening line of the book, just blow up my life and go do something crazy. And that's kind of what I did, and I went to Barcelona. 00:47:09 Speaker 1: You hit the eject button. The concept of time comes up over and over throughout the book, both generally and specifically. One of the things you write about is defining decades differently, and about the opportunity cost of your twenties. A lot of people who just buckle down and grind it out through their twenties. You say that for many people that's a trap. Smart twenty something's fall into to discuss that. 00:47:40 Speaker 2: So I and I think this is especially true in the like call it hyper competitive, like New York, San Francisco, maybe like Chicago, DC areas where you're surrounded by very smart people who went to really good schools and they go into like at least for like an early twenty something high paying job, but you're also objectively pretty, but you don't know anything you like, don't like No twenty two especially guys like yeah. 00:48:05 Speaker 1: And tell me when I get to grow out of that. 00:48:09 Speaker 2: I don't know. I mean you tell me. You're sitting there and it's like, okay, like what do I optimize for? And the obvious thing is money, and the like derivative of that is status, right where high paying jobs are typically higher status jobs. And I think it's when you don't have anything else. It's like like a north Star. You kind of go for like the like ambitious thing that will pay you well, that sounds impressive over and over again, and like, to be totally clear, there's nothing wrong with that, and that's also much better than like being a bomb and not doing anything. But you almost if you fall into that trap of like having some expectation of what you should do without it actually being like your own original thought like oh I want to go do this, you almost become instead of being like the protagonist of your own life, you're just kind of like filling a preordain role, Like you're almost like an actor, right, is how I think about. 00:49:02 Speaker 1: It, and in someone else's play, right. 00:49:05 Speaker 2: And I think the thing like I think the implicit bat people are making when they do that is I will like earn enough money and hit a level of stability where I can head eject, which you can do, but you can't buy back the opportunities that you would have had in your twenties when you're in your like mid thirties. 00:49:25 Speaker 1: So another quote, there's no saving time, there's no investing time. There is only spending time. And sentences like that is why I say this book is wise beyond its years, because I know people who figure that out in their fifties, sixties, seventies, not in their twenties. So kudos to you forgetting there to tell us what led you to that conclusion and how much did the pandemic lockdown accidentally lead to these insights. 00:50:01 Speaker 2: I think I became much more introspective much younger, because, like you just, I mean, I had roommates them, like I just wasn't spending like that much time in a normal day to day and I'm a very like sociable guy who like likes to hang out with people during the day. That gets removed and you're just in your head a lot, and you become really reflective of like how you're spending your time, what you're motivated by. So it was just like this again, I don't like this book probably wouldn't have happened if COVID didn't happen, because most of these like reflections were downstream of this hole just being like kind of in like an isolated stage of life at a point where like you should really just be like in an office grinding. So I think that was a big part of it. Hilariously, I like I mentioned, like the second chapter of the book, I used to be terrified of flying, and U like, like I'd fly all the time down I don't care. But for some reason, turbulence just like kicked my When I was younger and I was on a flight to Colorado about a year and a pandemic for ski trip, plame was basically empty. It was awesome. We had a super super turbulent takeoff and it was just bumpy from Atlanta basically all the way to like Kansas City, and I was just sitting there thinking the whole time, we're tolling to do die. Those thing's going now we're gonna die. Like it's I'm twenty three, it's over, I'm dead. And we obviously landed. I didn't die, but like some again totally random, but just something about that put that thought back my mind, like like at some point you are going to die, and it's not like up until that, I just thought I was gonna live forever, Like that's a not stupid, but. 00:51:37 Speaker 1: You don't really think about that in your twenties. When most people are in their twenties, they're immortal. You're not thinking about, well, one day I'm gonna die. 00:51:46 Speaker 2: Yeah, And that became like a forcing function for like, okay, let's work backwards from I finally got over the fear of flying. But it's like, all right, like we are, you know, we're on the clock, and what do I want to do with it? And so it was like a complete fluke from a turbulent flight kind of forced a lot of introspection that have been bubbling under the surface for probably the prior year. I was like, all right, like I should be doing what I want with my time rather than just letting inertia kind of do its thing. And it was that like call it like awareness of mortality that became like a forcing function for basically what I've done in the last four and a half years since then, like, be in control of your time. Don't don't be a don't be like a passive participant in your own life. 00:52:29 Speaker 1: The difference between money and time is that money is both infinite and fungible. Time is neither. This this is a philosophical concept. 00:52:41 Speaker 2: I consider myself a bit of a philosopher. 00:52:43 Speaker 1: Okay, I'm with you, I'm there with you. What's your conclusion when you realize that money is both infinite and fungible. 00:52:53 Speaker 2: I think you like need to be really aware of how much money it takes to get what you want out of life at various life stages. To your point, earlier, you can kind of scrape by in your twenties maybe early thirties and like still enjoy yourself. And the older you get, the more expensive it gets. Ideally you're making more and more money over the course of your life as well. So like my conclusion on that is it's like counter to a financial device. But like young people shouldn't penny pinch so much if they have like fun, interesting stuff they want to spend the money on. The caveat to that is like you should put yourself in a position where there are like high income outcomes from that over time. But like it's okay to be twenty five and not be rich if it means like spending money on fun stuff with your friends. Right. 00:53:37 Speaker 1: So, you're not a fan of the fire movement, the early retirement movement. 00:53:43 Speaker 2: Not when it's taken to the extreme. I think that the core idea of like having enough money saved up where like you control your own destiny is healthy and good and admirable. I think when you make the accumulation of capital to like escape the labor force as like an end goal, you just set yourself up to be bored and almost beyond that, when you're like overoptimize for fire and your whole thing is like I want to opt out of work, you're probably gonna hit that in your like early forties, when all of your peers are peak work. You're not gonna be able to relate to anybody after everal years. Against there's a lot of I think when you take the fire movement too far. There's like social costs to that that are harder to see when you're looking at a spreadsheet. But it's just like, and you have to forgo so many things you would probably prefer to spend money on in your twenties and thirties to hit that. It's just not I don't think you should like go into crazy debt and you should max out your four one K if you can and all this stuff, But like you just you shouldn't pass up on life to accumulate cash to be able to opt out of another part of life being work. Is kind of my take on it. 00:54:46 Speaker 1: No, that makes a lot of sense. I love this quote. Many of life's adventures are adventures only because you're twenty two and broken stupid and you're surrounded by other broke, stupid twenty two year olds. This is a feature, not a flaw of being young. Lean into it, yep, tell us about how you saw that. What is it about being twenty two and broken stupid that has to be embraced? 00:55:14 Speaker 2: So like I, I mean, I spent that whole year of being I guess I was technically twenty four, but I was with a lot of twenty two year olds who are like this whole like hostel hopping things hilarious, right, because it's basically a bunch of kids, like studying abroad. It's a bunch of people fresh out of college. It's a bunch of Europeans taking a gap year, a bunch of Americans fresh out of college, and then a bunch of like call twenty three to twenty six year olds who worked for a couple of years and took a break, and you're all just like in bunk beds. Everybody has a shared goal of like, I'm just trying to have cheap fun for a little while, and it makes every situation really really funny. Like some guys want to go from Sevilla, Spain to Paris and they're trying to game out like it's two hundred dollars to fly, but if we take a train ticket and then sleep in a train station for six hours, we can there for twelve dollars. 00:56:01 Speaker 1: And or and avoid a hotel room, right, and. 00:56:04 Speaker 2: Avoid a hotel room and extend our European trip like eight more days. Right, So or you have life? 00:56:10 Speaker 1: Did that right? You went from Barcelona to where in Europe? 00:56:13 Speaker 2: I mean I I covered I was there from August cit December, and then I went to Latin America a month later for a few months, and back to Europe and that August Citycember thing. I think I went to like nineteen different countries in four months, and it was just there was no itinerary. I would just go somewhere and then I would meet some people and they would say, hey, dude, we're going to Prog next. Do you want to come? And I was like sure, sure, And I meet this guy in Prague He's like, yo, I heard Budapest is great. I'm like all right, And then I was like, we're going to crack al Poland next I met a kid at a hostel in Crackowl who pitched me on his startup in San Francisco a year ago, like talking about weird yeah, small world stuff. But it was just like I went like pure optionality for a year and it was just like anybody I meet interesting was doing something cool. I'm going to go with them, like oh I heard Tromso Norway. You can see the northern lights. Let's go dog sledding up there, and like you do that. So the ability to just like cast a really wide net because when like cheap thrills are fighting, like having to sleep on a train or I have a buck bed with a stranger. It's just like it's fine, like when you're when you're a kid, you just don't care. I like, I'm still in my twenties now, but that would just sound awful, Like I don't want to be in a room with like twelve strangers and worry about my stuff getting stolen. 00:57:27 Speaker 1: That sounds terrible, but like twenty four, you got nothing to get stolen anyway. 00:57:31 Speaker 2: Yeah, it's like where they gonna take my backpack? We had a couple of like Czara T shirts and flip flops, sick Like I'll go play poker and win twenty bucks and go buy another one. It's fine. So and there's versions of that to play out and everything, right, Like I'm I don't think everybody has to go backpack Europe. But like you got to San Francisco and there's like twenty four year old startup founders that are sleeping in the office with a bunch of their buddies and they are having a blast. Like they're in objectively like horrid living conditions. They don't even notice because they're like twenty three or twenty two or whatever, like you can you can just really lean into like adverse living conditions and find them enjoyable rather than like they don't like take away from your life. They create really funny stories. 00:58:10 Speaker 1: I'm always fascinated by the pursue your passion recommendation that so many people make. You say, pursue your passion is terrible career advice. Yeah, give us some color on that. So, like, and you're giving this from someone who is pursuing their passion. 00:58:27 Speaker 2: So my my like more specific take on that is you shouldn't bank your income on a thing you're passionate about. The example that I give is, like, I love writing. It's a it's a thing that like I've enjoyed, I'll do the rest of my life, whether it's books, blogs, it's something I'll always incorporate. My initial job out of business school was columnist, podcast or media guy like effectively a media startup, and I actually found it stressful, where like every single day I had to like put something out and then I also was sitting there thinking this is draining the fun of like writing. Like I wasn't monetized as in my blog. It was just a thing that I like doing, and all of a sudden, now I don't have energy to work on that fun thing because I spend all that energy on the thing I'm paid to do. So the issue with like chasing your passion is one, a lot of passions aren't that lucrative. Two the second that your paycheck is dependent on you doing that thing over and over and over again, it can start feeling more like a chore than like fun. So the actual advice I have is, like, pursue stuff that you're pretty interested in that can pay you, whether or not you're like most jobs are boring for a lot of the time, so whether or not you're passionate about it, a thing that you're like interested in and like have an inclination for and have some skills at, go do that for a career, and then use that to like subsidize your ability to work on the fun stuff. Like I, you know, like writing writing books and blogs is like a thing I want to do independent of the financial outcomes from it. I'm pivoted from media to venture capital because, like, I like the offshoot opportunities of investing in tech companies, and that's just like a better world to be in for a career path. 01:00:01 Speaker 1: Last question before we get to our favorite questions that we ask all of our somewhat special guests. 01:00:08 Speaker 2: What special guests? 01:00:09 Speaker 1: How do I know I'm making the most of my time? 01:00:12 Speaker 2: So the last chapter of the book is called are You having Fun Yet? Which I think is like, I think fun is an underrated barometer that you're actually doing the right stuff with your life. And it sounds silly at like first glance, but my take on it is, I think the definition of fun and what you find to be fun changes as you go through life different stages. Where when I was like twenty three or twenty four, it was just doing dumb, hostile hopping stuff and like getting drunk all the time or whatever, and it was great. Now I get drunk a lot less of the time. It's still slightly a little bit more refined though, but like you know, once you get a little further in your career, like having real career success and making strides is like a source of like joy and personal achievement. When I was in college and playing football, like football objectively sucked, but like I like, playing college football really sucks, and anybody who's played it will tell you that. 01:01:05 Speaker 1: But it's like a by the way, the description of the work at routines in the six am wind sprints and but but when you know deep into the season the coach tap rains we get in there. 01:01:16 Speaker 2: Yeah, it's like it's like an incredibly like fulfilled Like it's like going from a walk on to be putting on scholarship and then like getting made team captain my senior year, Like that was a much cooler fulfilling moment than like anything I did before or after it. Like I think it was because it was really really hard, right. 01:01:32 Speaker 1: So in a real sense of achievement. 01:01:34 Speaker 2: Yeah, like it was a it was a hard thing and I'd like executed on it, so but it was fun. So my kind of definition of fun is if you like find joy in the suck, then you're probably doing the right thing. And like that could be being like groggy and hungover like on a park mentioned Spain, but you feel like you're living out an adventure, or it could be like going after like a really ambitious career and like excelling in it. And it's you know, I think a lot of people as they get firs they're in their careers, they keep chasing that ambition high off of that to the detriment of like their family or other parts of their life. I think a lot of young people like just start like I think the biggest mistake you can make is like keeping a prior version of u's like benchmark or idea of what they should be doing with their time and trying to like force apply that to a future version, or trying to pull forward a future version too early in your life at the expense of the fun stuff you want to do now. And I think just having a very very strong sense of, like, what are the most important things right now that bring me fulfillment and then going after those is the recipe to a good life. 01:02:40 Speaker 1: And the sequel to this fine joy in the suck is a great. 01:02:44 Speaker 2: Could be title. I just call it like middle aged money. Once I get my thirties. 01:02:48 Speaker 1: Well, you can do something every decade. You have a built in model your money, slightly older money and money. You got a whole run of things. All right, Let's jump to our favorite questions that I ask even my somewhat special guests, starting with you're still young, tell us about your mentors? Did anybody really help shape your career? 01:03:12 Speaker 2: Yeah? I mean the early mentors would have been football coaches in high school and college defensive line coach Harold Brantley, he was the man like he was. He was actually whe who pushed me to the point that I could play in college in the first place. And then my college defensive line coach Kenny Baker was like I was. I came into college playing in a small private high school and thought I was And then I got to college and just got wrecked for like a good year and I was like really. 01:03:37 Speaker 1: Good, faster, stronger, or you just didn't know the game as well and didn't have the skills or some combination. 01:03:43 Speaker 2: Like it was like I just had to get better. 01:03:46 Speaker 1: It was like better shape, better skills. 01:03:48 Speaker 2: I needed to get stronger and just be able to react to the game on the field way faster. And I just wasn't The processing speed and the just size weren't there. 01:03:56 Speaker 1: People don't realize that the quality of play at the college level, it's astounding. 01:04:02 Speaker 2: We played so we played Alabama, Little Mercy University. We played Alabama and Auburn in the same year. I like you want to talk about seeing like like like us. We almost beat Auburn. We were down seven in the fourth quarter, but Alabama Jalen Hurts to uh Mac Jones smoked us. They had Calvin Ridley, all Pro receiver who briefly had a gambling problem, but he's back as their punt returner. Guess who started on the punt team was getting juked out of his shoes like twenty times because we punted so much. Me But defensive line coach Kenny Baker was like, he I worked really hard, and he could tell I did, and he was very encouraging and that like keep the work ethic up and like you will develop, like you will catch up to the point that like, if you keep that work ethic, you'll be able to play. And he was right. By my third season, I was decent, and by my last season, I was objectively good. Like I was never going to be an All American, but I was like a starter and was like a very solid player. But I could easily quit and transferred to Georgia and like, you know, done the fraternity thing at SEC school, which would have been short term more fun, but long term less fulfilling. So football coaches post post school, it's funny, like especially with COVID, my early mentors were like kind of people I found through Twitter. Like I remember when I read The Psychology of Money. I thought it was like a very profound book and I just like digested everything Morgan house Will published. And then a year after that, like I remember when he followed me back on Twitter. I was flying from Sevilla, Spain to Manchester, England, and I looked at my phone. I was like, Oh, this is really cool. This is really cool. And then when I moved to New York, we like hung out in person at Collob Fund's office and like, like great guy, but I would say like as a somewhat career slash just aspirational. Him and Tim Urban were like my two favorite bloggers from the kind of. 01:05:51 Speaker 1: Like you referenced Tim Urban in the book, but I think you referenced a piece of his and I was pro you didn't reference the piece on optionality, the so to chart with the black lines. 01:06:05 Speaker 2: Yeah, everybody steals it on Twitter. 01:06:08 Speaker 1: I find that piece to be so interesting because you know, one of the things about getting old is some of your optionality goes away because you don't have Hey, this is a twenty five year project. Do I really have twenty five years? 01:06:22 Speaker 2: Like? 01:06:23 Speaker 1: What am I going to be doing at age? Ninety. All right, maybe a twenty five year project isn't the best thing for me or at age eighty best thing for me to start. But I laughed at a lot of your references because I'm familiar with many of them. They were really really good. So so you mentioned Morgan, any other post college mentors you want to bring up? 01:06:46 Speaker 2: Yeah, I mean, like i'd say my current boss, Sam Lesson, great guy. I mean he's a He's had a very cool career, right, Like he like started a company in his twenties in Brooklyn, ends up getting acquired by Facebook, like had a successful career at Facebook, and then like co founded the venture fund I work out now, right, and like he's like, it's it's funny. I feel like a lot of people in my bubble of like the late twenties have this like is this what I want to do with my career? You kind of hit this inflection point of like you should pick a thing that starts compounding, and like his take has always been like you should just want to work with like really interesting, smart people you respect and like work on interesting problems. And that's a pretty good recipe for finding career fulfillment. And you know, if a couple of things go right, like financial success, but like it's I don't know. He he's done like a few different things and now like has like an objectively like I like if my lifestyle and like life is set up kind of like his in my forties, I'll be very cool with that. Like so he crushes. 01:07:43 Speaker 1: So you mentioned Morgan's books. Tell us what you're reading now? What are some of your favorites. 01:07:49 Speaker 2: So, I I just started reading this book called eighteen seventy three. It's I think it came out pretty Yes. 01:07:55 Speaker 1: Who won the Pulitzer for I forgot the name of the four central bankers that his first book was about. That is literally at the top of my queue, ready to get. 01:08:08 Speaker 2: It's how it's I'm about halfway through, and it's it's like very good and interesting. I mean the thing I've I've done this from time to time, Like I hadn't read much over the last year while I was working on that. 01:08:19 Speaker 1: Yeah, now I'm writing is a kill you. 01:08:21 Speaker 2: As someone who's written books, I had so underestimated, Like I have much more respect for other authors after going through that. 01:08:28 Speaker 1: Exactly, can't you read books? You can't blog? You can't It just sucks up so much. 01:08:33 Speaker 2: Time with Yeah, it's like all your free time goes to that. But something I've always liked is I've always been a big biography guy or like certain moments or events in history because you can get the chat, GPT whatever. People can pull a story together in three hundred pages of a thing is so fascinating, and with like eighteen seventy three, like reading about the stock market speculation in the like Vienna, Austria stock market in the eighteen seventies, and then you're just pattern matching that again, it's like what I saw with retail investing in twenty twenty, twenty twenty one. It's you just see like human behavior playing out cyclically one hundred and fifty years ago. Is just really really interesting in like a you know, totally different time and market and paradigm, but it's the exact same thing. 01:09:16 Speaker 1: Lords of Finance was his first book that won the Pulitzer. I'm excited about that book. Any of the books you want to mention. 01:09:24 Speaker 2: The Infinity Machine, the one about the DeepMind founders, it was by Sebastian Mallaby. I think anyway, it's like as far as Ai is now the thing everybody cares about. He did a really good job of like like how llms even became a thing in the first place, and how like this is just group of like British researchers who've been holed up in London the whole time kind of kickstarted this whole AI boom. And even though Sam Altman Elon Musk they aren't like main characters at all, You're getting these interesting anecdotes of how like open AI came to gather and how there was like a bit of a coup with an open AI and then Elon leaves. It just did a really good job of framing like the current moment in time and how we got here. But those are like I read both of those, who have been reading both of those in the last month and a half. 01:10:08 Speaker 1: They're great interesting. What about streaming? What are you watching or listening to give us your. 01:10:14 Speaker 2: Favorite hilariously on the like on the On the podcast front, I don't have any shows I listen to regularly, but I will selectively if there's like a guest that I find interesting for whatever reason. I've like it's everything from tuning into like like Josh and Michael on the Compound and Friends or like Tim Ferris's show or some Scott Galloway stuff. It's I'm so much of a I have people who I think are good interviewers. I don't care about half the people they talked to, But occasionally they'll have someone where I really want to hear that because I think they'll pull out good questions, like I don't know, Michael Lewis on Tim Ferris really good episode, or it's there's nothing I listened to specifically streaming. I did like that movie Obsession. I thought it was phenomenal. It was the one that like when Megavi out of indie film that when Mega viral out of nowhere in it? Who directed it? It's the I can't even think of the guy's name. He was got to start on YouTube. He does a lot of short form comedy. But it like blew up and it was the one about the guy who like breaks the stick to make the girl like he makes a wish that the girl falls in love with him and then she goes full psycho. Anyway, it went like nuclear on Twitter, Instagram, TikTok whatever, pretty good horror film thriller. I liked it. 01:11:29 Speaker 1: Final two questions, what sort of advice would you give to a recent college grad interest in the career in either writing, content creation or venture capital. 01:11:40 Speaker 2: So my my take on all the career stuff for that is, like, I think it's really I think that one of the higher leverage things you can do is just start a blog and put your thoughts out there, even if you have five people reading it, fifty people reading it. I think that especially with AI becoming more and more of a thing, it's easy to like, like, resumes are becoming incre something meaningless, both from like the odds of somebody actually looking at your job application when you send it in cold or very low, and the ability to like lie, like you can make one hundred different resumes with LMS based on the job you're applying to now versus when I was, Like when I was in college, you always tweak your cover letter or resume per job, and it's pretty tedious to do that when you're doing it by hand. You can make a million once, right, So having some like like proof of your thoughts on thing, or you've articulated ideas online that show how you think, I think, carry a lot more. They've always been important, but like stand out a lot more now with AI or if you like AI coding assystems are really good, like anybody can access them to build stuff. So just having a portfolio of like written work or stuff you've built online that shows that you took interest and initiative and a thing and like put yourself out there super useful. I mean. My my take on career stuff in general is like if you can go into investment banking or consulting right out of on you, it's still probably the right move, just from like getting trained on how to work hard. People who work at Goldman from twenty two to twenty four are typically more competent than other people. And for all my stuff about like you should go take risk in your twenties, the caveat on that is like you should have a couple of prestige STAPs first, Like Columbia Business School was a prestige stap for me. I enjoyed it, I learned a lot. The main reason I went was like I went to a somewhat no name undergrad. It's not like I worked at a marquee firm out of undergrad. Like you want to get a couple of like I have, like somebody's de risked me as an individual. Then you go take the shots that you want to, so like I it's like have a collection of like independent work and thoughts like you can share like in real time. And then I think it's important to get one or two prestige STAPs before you go jump off and do your own thing. 01:13:50 Speaker 1: And yet in the book you talk about what a what a misfocus it is hyping on status and why that whole game is so cheah. 01:14:00 Speaker 2: So the status thing's so nuanced. I think that if you treat status as an ends to itself, you're going to be incredibly disappointed. I think if you treat status as a thing that you can acquire and leverage to actually do ease to an end. Yes, like if the trade is I'm going to go to an incredibly competitive school and spend two to four years working in some version of like Goldman, Blackstone, McKenzie, whatever, and I can come out of that and do anything that's very much worth it. But you don't want to be the person who, like ten or fifteen years into their career never really figured out their things. So kept chasing status is like a vanity projects. It's like I say, status as diminishing returns or like once you have enough of it, it gets marginal. After that, you're good. 01:14:44 Speaker 1: And our final question, what do you know about the world of investing today? Might have been useful back when you were locked in your bedroom trading specs. 01:14:54 Speaker 2: I underestimated how much retail investing is like a permanent fixture in the market today. I think it compounds from like and this is all like public market stuff, but like pod shops, trading, quarterback, quarter are like more and more of a thing. Passive investing is more and more of a thing. You could argue that true, like price setters being like fundamental long short funds or and like long only mutual funds are less of a thing. So it's created this thing where you have like a lot of like very short term trading on like whatever, alternative data, quarterback quarter data, and then you have a lot of passive stuff and then a really big active group is like retail investing is a thing like game stop. I thought was a one off fluke. It wasn't like open door short squeeze out of nowhere. You're seeing like random companies will just pop off like five percent, which makes it like Dan Sundheim was on a podcast with the Collison Brothers, the Stripe founders. A couple months ago, he was talking about how they changed, like how they position their shorts now d one capitals, because you just you could be fundamentally right, but guess what, fundamentals don't matter if the borrow rates through the roof and the stock like eight and you get blown up right, like like ask the game the Melvin Capitol guy about fundamentals when his fun got blown up right like it. At the end of the day, the only thing that matters is making money. And I really thought a lot of that was a twenty twenty twenty twenty one thing and it was COVID and people were at home. We're seeing so much stuff with like random speculative like nuclear reactor. Like a company Akalo went public through a spack. It was like a Sam Altman backed company. It was worth like forty billion dollars. I don't think they have a functional reactor. 01:16:28 Speaker 1: Yet, Like, are you suggesting that sites like Reddit, Wall Street debts still carry the influence they used to or has that attenuated and then it's spread out to die? 01:16:39 Speaker 2: I would argue that they almost carry more weight because I think that, like really, I think there's this is pure speculation, but I think that they're now increasingly a thing that like call it like institutional traders, quant funds, whatever, we'll like look at as a data source where if something spikes on one of these sites, they'll play the momentum and like it makes these bubbles go even further than they used to. And everything happens so fast now because like the speed that information moves on the Internet is just instantaneous. That like a bubble that might take like months to build up and then collapse could happen within a week both ways. So it's just like the whole like internet spread of information faster and faster. It's all all derivatives, like retail investors getting in the market and then yapping about stuff online. That's just never gonna stop, right. 01:17:24 Speaker 1: And it's so funny because everything old is new again. Back in the day of the Yahoo message boards, like yeah, like iomega and and that sort of stuff, nothing has changed. It's just how much faster were. 01:17:39 Speaker 2: And it's like zero commissions. Now it's like the there's. 01:17:42 Speaker 1: And it's in your pocket, you know how let me go home and call my broker does it? 01:17:46 Speaker 2: And now there's like, oh we have prediction markets and sports batting on your phone. We have removed all friction from people putting money at risk to do stuff, and we've made. 01:17:54 Speaker 1: Regardless of how dumb or speculative it might. 01:17:56 Speaker 2: Be, and the speed of which you can communicate what you're doing is now all so instantaneous and free. So you just have people constantly going risk on on whatever for whatever reason, and then everybody else knows it. That's just that's only going to keep accelerating. 01:18:10 Speaker 1: Under except it kind of sounds like a very late stage bullmarket. 01:18:16 Speaker 2: Could have said that in twenty one and we were right, twenty two is kind of a bear market. Then AI happened, So it's like I think that. I just think market cycles in general will keep happening faster and faster because it'll collapse, people get blown up, and then somebody starts running another thing. I just think it's going to get more and more violent. 01:18:32 Speaker 1: I have a pet thesis that the giant reset, the giant fiscal stimulus and crash and recovery in twenty twenty was like a reset and extent of the bullmark, and another I agree with that ten years it's but anyway, Jack, you you were more than a somewhat special guest. 01:18:52 Speaker 2: Thanks. 01:18:52 Speaker 1: This was really great. Thank you for being so generous with your time. We have been speaking with Jack Rain's. He is the author of Young Money, a field guide to wealth and purpose in your twenties. If you enjoy this conversation, well check out any of the six hundred and fifty three we've done over the previous twelve years. You can find those at iTunes, Spotify, YouTube, Bloomberg, or wherever you find your favorite podcast. I would be remiss if I didn't thank the crack team that helps us put these conversations together each week. Alexis Noriega is my video producer. Sean Russo is my researcher. Anna Luke is my podcast producer. I'm Barry Rutoults. You've been listening to Masters in Business on Bloomberg Radio.