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Podcast. 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 marginal in your school living in south. Spanish is very asi-hasty right now but it's like sufficient. There's no real career path other than figuring it out from there. That's intriguing.
I'm cracking up because I have so many different ways to go with this. This gig at school was corporate finance at UPS which you described as mostly moving a mouse around the screen and trying to look busy. Tell us about your experience in corporate finance. Yeah, I mean to set the stage a little bit I graduated in December 2019 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 2020. 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 have the same experience where a year and a half later you're still remote.
I don't think it's great to be a 22 year old who's never had a real job who's then told you're going to work from home while you have your Xbox and all of your friends doing the same thing. It was actually a terrible environment to start learning how to be a worker. Yeah it was just Zoom calls, Excel sheets, modeling out fuel cost projections and forecasts for UPS for like 2022. Yeah, I was honestly bored the whole time and to build on top of that I got into business school out of undergrad.
So 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. And then you 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 18 months. So having that window where hey I know where I'm going to be 18 months from now in September of 2020 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. So like when I was a kid I always loved to travel and my grandparents would take me everywhere. So grandma took you on a crazy trip you described in the book to Savannah in Africa. Yeah when I was 11 my grandma and my mom are she I'm always grand 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 meant anywhere. I wanted to go somewhere crazy like Africa or Asia and we live in South Georgia. Initially I pitched Costa Rica and she said that's like a three hour flight. I was like okay.
Tanzania I like I thought the like I had a big map of my rooms and I thought it'd be cool to go to the Angora Gora Crater and see not kill him and Jaro 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'd 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 18 months and you're bored and then I for better wear a set of fortuitous run trading specs and spax warrants for the pandemic which gave me an up it gave me more money than I expected to have at 23 or 24. I mean I wouldn't call it that much you just go hostile hop Europe and Latin America for a year.
Yeah I'm glad you brought that up you're not trust fun but it but baby in any stretch of the imagination. No you scrape together some money fly coach you're staying in hostels you have 10 roommates and in these. Eating like McDonald's or euros or whatever every day it was the best. I mean I got food poisoning one side it was fun.
More recently you wrote a story about going to someone's wedding and I think it was India and a bunch of people got food poisoning and it was hilarious. It feels a little bit like India right now and it's like the air quality today as a recording is pretty similar to you. It's like a bar that's like a yellow. It's like for micro dosing New Delhi air right now it's great.
It's good stuff. Only without the the E. coli that you described. But let's 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 you make that transition? Yeah it was it was interesting like I the back of my head I kind of knew I had this start date moving to New York in August 2022. So I eventually quit my previous job first shot at college in August 21.
I 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 going to go to grad school then we'll do our career in New York and yada yada yada. It was it was funny because it was it first weird like be 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 I love I love Columbia.
Honestly I love New York in general best city of the world particularly in your twenties and it took a couple of months to really get 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 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. I mean the 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 it's pretty easy to conceptualize money like when you're taught from like in high school how money compounds every time if you invested and it's you know you should be frugal and save up money but what you miss is like what's the ultimate time to spend that money on different things and the example that I give a lot is like I was 24 and like sleeping in a bunk bed in a hospital with 12 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 coed and it's like it's like summer camp for like young adults.
But then occasionally you meet somebody and they're like early 30s staying in the same hospital and it's like you can almost tell that they notice they're like probably six or seven years too late to have done that type of trip. And the biggest takeaway from traveling was like if I really wanted to do this trip this was the right window to do this. I optimized that phase of my life correctly for somebody who wanted to do that type of thing and that's kind of what's talking to me the most after is not just being aware of what you want to get out of life but what things have deadlines where if that window of opportunity closes you're just not going to be able to maximize your fulfillment or enjoyment or like utility from that experience. Basically everything you do in life has an expiration date from when you would enjoy the most.
You can go cheap and cheerful in your 20s maybe even early 30s but not much faster. 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 your writing and why you thought that might be a career path. So like hilariously when I was doing the whole SPAC trading thing in 2020 and 2021 I had a burner Reddit account called Barmelo's Anthony.
It's a play on words on Carmelo Anthony and Xanax bars. It was my name in 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 SPAC and then they announced a deal with Fiskar Automotive three weeks later. It was like borderline conspiracy theory stuff but it worked. A lot of it worked. Yeah so I always like just writing about like stuff I was seeing going on 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 issue media companies nobody would hire me for lack of like professional writing experience. So I just started writing like I just watched 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 exercise for anybody to really distill what you think about a thing and try to sit down and put pen on paper.
Daniel Borsden the librarian of congress is famous quote I write to figure out what I think and besides at that hour the bars were all closed. You know until you put it down until you put a paper or fingers to keyboard it's sort of nebulous and not distinct once you write it there it isn't black and white. Yeah so for sure. So you come out of Columbia what's the first gig you're doing while you're a new grad?
So to set back a little bit when I was still in business school I kind of had this like I think investing in financial markets interesting I really like writing I 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 Redpoint 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 an investing seat somewhere not split the middle and do like the marketing arm of investment group. So going into my second year Sam Rowe you know friend of the show he was like contracted by Robin Hood to help them with the hiring for their building on a media subsidiary called Sherwood News we grab coffee and he was like I don't know what you're playing as after business school I think it'd be good to 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 like there's a lot more stability there from like financial backing. Tell me about having a media outlet attached to a large FinTech or data services company.
The entire pitch was just trying to like basically make a new age Bloomberg. Did you guys get any hood stock? Yeah. Yeah.
So not terrible. Not terrible. I mean the issue was only working for a year since I got that much but like it yeah like 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 I ended up joining them during my second year I signed the book deal for that book the summer after I graduated so about two years ago now and 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 writing a blog I like kind of free range points on the internet but I didn't like the actual like call it nine to five employed version of like financial media and my like I 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 potential but the momentum and this and that that's what the other one and I have like a total career panic like to almost two years ago like fall 24. And there is something to be said about the daily piece that must be fed when you're on a regular deadline like that stuff 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 fascinated about an essay you did how I lost $150,000 in a day trading specs way back in 21 tell us about your ramp up in the spec world and then the blow up oh it was I mean it was awesome like I like I was I don't know if you would have checked my like pollsters stress levels at that point they were through the roof but like it was crazy so it's like right with a pandemic hit I thought I was like the next Michael Burry I had like $10,000 my checking account threw it all in spy puts they tripled because obviously the market was gonna take and I was like yeah I'm him and then you know Bill Ackman a week later was like crying on CNBC said the world's going to hell and I was like S&P's going to like 1,000 let's do it again let's buy more puts you know I actually having not really been an adult during OA.
I completely underestimated like the fed and quantitative using how that could work and how fast that turn it like I my face got melted on I was shorted the actual bottom and then I basically round for up to $10,000 to 30 back to 10 I might tell it's when my legs I was like I'm never trading a stock did you ever feel the need to reach over the waste paper best get in throw up no but like if it had been bigger numbers maybe so I'm like I'm never gonna trade stocks again I put $6,000 and I open like a Roth IRA do my one contribution first year as 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 evil spack it'll turn into drafting stock in like two months I was like like an IPO and he's like I don't know dude I just saw him I buy this you own drafting so I was like okay I went on the rabbit hole I was looking at it's like and it's a par it's before it comes out it was a trading it was trading it was trading so the par on those spacks is like $10 it was trading at like 12 or 13 oh really maybe 15 but the warrants have doubled or tripled right because all the warrants have a strike price of 1150 so then I like traded options enough I understood like strike prices expiration dates whatever and the thing that jumped out was that warrants don't expire for five years and they have an 1150 strike price so I was doing the math and I watched draft Kings after the merger happened it ran out to 20th the warrants ran out to eight or nine dollars you would double on the stock you would have made like nine X on the warrants if you bought them at a dollar like a peak pandemic collapse so I was like okay this is easy well I was just like spacks obviously kind of seem like a bubble right now because there'd been like nickel I motors that announced 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 but I can just pick the spack warrants early I can make money so nickel I want to trade it $3 I bought $6,000 worth I made like 12 grand a couple weeks later and then I just kept rinsing repeating spack warrants and like six months later I got from six grand to 150 grand and I was like this is so easy so then I by the way that that should immediately set bells off I doubled down though it didn't sell any bells because then I was like okay it did sell one bell I was like warrants are risky if any of these deals collapses the warrants go to zero I should start buying the shares as close to now as possible so I was in like an online discord chat with a lot of other novice people we built some web scrapers that would pull every spack SEC filing so as soon as a filing hit the press like trading halt some news comes out for spack I would get a push notification open up the deck skim it if it was electric vehicles marijuana outer space sports batting or renewable energy I would go all in unless the unless the like valuation the deal was just egregious I would go all in and I knew that the stock would probably pop like at least 30 or 40 percent because they just did every time so you get an 11 your max loss is probably like 5% on any trade and you sell at 14 or 15 so you're basically risking 5% to make 40 percent a symmetrical risk reward that's what you want and I did that like seven times in a row and then I went from 150 to 400 and like I'd only risk on any given trade like 5% of my portfolio and they didn't all hit but like enough did it didn't matter and my dad obviously I kept telling what I was doing and I hit like it was February 2021 and he called me and he was like you should probably just sell and just put it in like an index fund I was like I knew this two more times I'll have a million dollars at 24 pretty sure I can get there that that should have been the screaming is the battle ringing that and then when he and his brother were talking about potentially managing some of our family's money you should have your 24 year old kid he just made 6,000 centering specs 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 that would have been a bad idea so getting to how I lose the money at this point way too many specs Shaquille Neil has a spec Paul Ryan has a spec like everybody in their mother has a spec and the bubble didn't pop it just stopped bubbling because there was kind of this pool of money that was chasing every hot spec and then there's like a hundred of them on the market somebody now it's a deal the terms are getting worse and worse and you're watching this decay in real time yeah and it was like by April May of that year it's getting tougher and like a deal you're gonna out some might jump 10% you're just I was like I was addicted to the rush so there's a buy now pay later company called catapult 80% of the revenue came from Wayfair obviously a pandemic darling and this is at the time when square bought after pay for like $30 billion crazy price firm went public at like $30 billion 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 is gonna have earnings in August they've had no sell side coverage I just need like one analyst from like Morgan Stanley whatever to initiate like a buy the stocks gonna double I'm gonna buy a bunch of warrants like a dollar 50 they're gonna rip and then this thing I'm gonna make a million dollars on the straight this thing had already gone public through a spec like there was no floor that deal was closed just a normal company so not your traditional spec trades that you've been doing before it had gone public through a spec that's just like a normal company at this point and I just ate into it with like 300 I think I had like $330,000 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 10% loss and I was just like I was just pot committed to like this is gonna be the millionaire trade they missed earnings so badly the stock fell I think the stock fell 20% before market opened on like August 11th and the warrants immediately got cut in half by like 50% and that's 150 grand 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 a hundred thousand warrants and a dollar or whatever and then there's the four 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 is rug pulled which was the right move because I basically liquidated my position pre-market went from like $300,000 like 150 or whatever and I was just like man that sucks put in the S&P and then just went to the gym and worked out for like real self-loathing workout for three hours 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 swinging for the fences am I really putting 50 or 100% 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 the issue for me was like the the plan I had initially of like buy SPACs near NAVSEL when they pop was like a good strategy and if I'd stuck with that even if it stopped working it's like okay the downside is the minimus we made a bunch of money this trade doesn't work just like park an index one until like you know 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 that hit a million I would have walked away but that was like a benchmark number oh you should know that when you hit a million I would not have walked away junkies don't say one more hit and gamblers don't say I just need this parlay to come in right and then I'm good because you're always looking for the dopamine hit for the adrenaline I would found something else to speculate on but I think I would have stopped trading SPACs how that happened coming up we continue our conversation with Jack Raines discussing slow ventures and investing in creators I'm Barry Ritalts you're listening to Masters in Business on Bloomberg radio 30 seconds in that time you can check your phone reheat a cup of coffee or decide to skip songs in 30 seconds we can confirm an unknown identity lock onto a distress signal and switch course to respond when every second counts the Canadian Armed Forces is ready it's every time it's all the time it's our time learn more at forces.ca slash our time a message from the government of Canada as markets move and headlines break what matters most is context a Bloomberg subscription gives you unmatched reporting sharp analysis and powerful tools that help you connect the dots visit Bloomberg.com slash podcast offer to learn more I'm Barry Ritalts you're listening to Masters in Business on Bloomberg radio my somewhat special guest is that how you want to be that how you describe this is a marginally special special guest Jack Raines 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 join Slow Ventures in San Francisco from New York did you really locate the San Francisco and then come back to New York so I kind of get this venture by Coastal. 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 fly for the New York job and that was the part in New York first and then one of the GPs in San Francisco San 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 jump super sweaty and like shovel looking and five minutes in five minutes I think you would agree with it five minutes in the call he said what do you think of San Francisco and I said no at homeless people and he was like it's a crazy ass for somebody applying to 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 SFC and I was just like he told me like take a beat and like think about it and I I can't remember if I told him on the college 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 but I've been to 25 other countries in 50 other cities I'm sure I can figure it out yeah the only difference in San Francisco has so many more AI startup advertisements on the billboards and the waymose which are awesome but yeah like I mean I and they are everywhere we're just there so they're so sick they they're like yellow cabs in New York yeah yeah they're there they're in crime I mean the worst thing about New York is that we keep trying to like block waymose let it happen I'm so pro waymose waymose biggest fan boy um but yeah I go back to fall 2024 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 setback 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 can still have like bandwidth and flexibility to do so which like eliminates a lot of investing stuff or those compliance issues no investment banking no no trading on a desk and no portfolio management or even um cfa analyst where whatever you do is discloseable and requires approval and it's complex 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 background VCs 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 writing and all this stuff so I just kind of started pounding pavement like reaching out of VCs I knew my network that may or may not be hiring and slow happened to be hiring and I messaged hilarious I messaged yoni the partner New York I'm blue sky I was back when everybody thought twitter was gonna die in blue sky well blue sky didn't take off but it does feel like twitter is kind of ground to a shell of what it used to be I think it started 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 are literally last week Nikita beer tweeted they tweet the algorithm so like you're seeing your mutual followers and I was like dude that's what it should have been the whole time right but anyway basically I hired from a twitter DM and then the last second flight to San Francisco six weeks from application to starting in SF basically like I didn't know where to live I want to face but marketplace found some dude with an open room and just hop on a facetime with them and I was just like yeah like I guess I'll just take the other path of your apartment and then I moved there that was I just put myself in a suitcase and just flew out so are you New York based today I live in New York now I moved back here a few months ago right and and how do you how do you work that out if your core office is San Francisco so we have an office in New York to flat iron so twenty fifth it was one of those things where we were pretty ac 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 suburbs a little bit he would come up sometimes but I would like take the Caltrain down to like Hillsborough area and like go to his place like work from his pool house with him it was a funny setup but it was like we were acing enough and I also knew that like long term I was gonna live in New York I just pitched them on moving back and then flying out San Francisco like every three weeks or so and that's the setup I've met New York has a pretty robust technology sector I mean we all think of San Francisco for AI computer mobile tech in Boston for healthcare tech we're just New York landing that in that list it's it's it's it's I would put New York is the like pretty fast rising right on for like consumer tech I would argue it's like number one close to it and then you got a big Google office here you got a big Microsoft office here you got a giant Amazon office here well and like anthropics opening like a sixteen thousand square foot like they're opening a massive office in Hudson Square like you're in some space there a lot of like 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 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's more insular and it's like there's just engineering talent from like Stanford Berkeley whatever that aggregates around the base so it's it's honestly a big part of like engineers and up on the West Coast and then a lot of the sales people in the East Coast a lot of customers are also on the East Coast 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 megaphones are really just cold calling yeah I don't think of VC in those terms explain are you really just smiling and dialing like a little bit it's funny um like I don't know if you read Bill Gurley's new book run it out of dreams or he said something similar adventure capital is 90% sales and it really is like but that's true about everything in finance yeah and I don't know about outside but everything the space is you're ultimately asking someone to trust you and give you their business yeah yeah yeah VC especially at the big it's like what slows a fairly small fund right like we have like total teams like 15 or 16 people investment teams like nine or 10 people um but like some of the bigger funds like I have some buddies that have worked at the like call it some combination of like the general catalyst type a 16z 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 um I was a little tongue in she said it's like cold calling but it's 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 they really do try and quantify it and turn it into 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 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 so it's funny we actually we actually just announced one that's like robot e doing like uh like uh warehouses and fulfillment for e-commerce companies called Suttronic so we do occasionally touch they don't make a robot you're not doing the human form right right we're not doing any of the stuff that gets clowned on twitter because you can't fold clothes or do dishes right um i mean it's we're like broadly generalist we've done everything from like we've done just to name some companies over the last 10 or 12 years like Robin Hood slack um all birds before they pivoted to being an AI GPU company back when they sold footwear um i mean we have like a hilarious one meme lords technology where it's basically software platform it's like a basically marketing tool platform but for creating memes um i mean well 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 and when 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 multibillion valuations and made a lot of money so like you can argue we should have played that trading game the bet that we're making is like go for the stuff it's going to compound long-term value that could be like a standalone value-density how does the sort of girth of IPOs although we're in the middle of a period where there are suddenly a spate of them coming out um and more and more companies choosing to stay private for longer how does that figure into the VC calculus of hey we eventually want to exit and we can't rely on someone else either from a bigger firm taking this over or some emanator to give it's interesting i almost think you have to put VC 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 stakes to like a later stage bigger growth like a bigger growth investor what's there in the unicorn status or you get the acquisition or IPO if you're getting at a company that's worth 20 or 30 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 50 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 10 billion or 100 billion we think it can be worth 100 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 you're primarily seed in eight rounds but you're not doing be rounds or we occasionally will with follow-on capital but it's like 95 percent cna 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 on coming at like a five billion dollar valuation from portfolio construction maybe you should with the megafunds it's like okay if you're gonna 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 entropic those are gonna go out at potentially trillion dollar valuations like the math works if you invest 40 billion dollars across a few big funds and something at like a 200 billion dollar valuation and you get a 4x or 5x you're returning like tens of billions of dollars right so it's like at the early stage should probably be looking to sell in 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 entropic that could go out a multi-hundred billion dollar valuation you have to be concentrated in those otherwise the math is gonna work if you get those right you can like 2x3x if you don't you want really kind of interesting you come out of the creator economy so ventures has been a player in that space how does how does your experience help you as a VC and and what is slow ventures see in that space that you know the traditional venture capitalists overlook 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 64 million dollars we invest directly in creators meaning like youtubers podcasters 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 we have this in like Sam my boss was kind of came up with this idea a few years ago that like he calls it most investing in cults but people who have a true like cults 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 the 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 all this stuff these are 360 deals covers everything that person does yeah yeah we basically podcast could be sub stack could be all of those 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 Katzimoses and he has a like he has a massive YouTube channel especially I know that should show it is shockingly intriguing yeah watching this guy build stuff from scratch yeah he's like relaxing too 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 of revenue so he builds various things and sells them so he also generates revenue from the YouTube right and it's like a specifically has like a tool line called KM tools and like we invested money in 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 putting out YouTube videos also like more people to help rolling out new products and wider products we have tools so the bet is that like you put money in that and maybe like the tool business really blows up and then 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 like a woodworking festival in Texas people come out like to come like get him to like sign their autographs like 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 just 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 Mr. Beast has a bunch of different businesses if you back Beast Burgers didn't really work that well if you were backing Mr. Beast as a whole like Jim's entire empire was worth like a billion dollars or whatever so you want to be like aligned where if they want to change their focus like our capital still aligned with that like you don't think this this experiment's working move 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 to 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 Raines discussing his new book Young Money a Field Guide to Wealth and Purpose in your 20s I'm Barry Ritalts you're listening to Master's in Business on Bloomberg Radio 30 seconds in that time you can check your phone reheat a cup of coffee or decide to skip songs in 30 seconds we can confirm an unknown identity lock onto a distress signal and switch course to respond when every second counts the Canadian Armed Forces is ready it's every time it's all the time it's our time learn more at forces.ca slash our time a message from the government of Canada now Bloomberg.com subscribers can shake the conversation on Bloomberg Radio we got a we can smart question can we find the conversation some big questions for experts and guests do you here on air visit Bloomberg.com slash ask radio to send questions to our hosts we may just hear them asked on the air exclusively for Bloomberg.com subscribers get answers on today's headline breaking earnings news at Big Market Moves visit Bloomberg.com slash ask radio to join the conversation right here on Bloomberg Radio I'm Barry Ritalts you're listening to Master's in Business on Bloomberg Radio my pretty special guest my kind of special somewhat special somewhat special guest I'm going to write that down my somewhat special guest is Jack Raines he is a associate at Adventure Capital Farm and a author I've been subscribed to his substack Young Money for I don't have any years has been around four or five years let me know when you get to 30 and you'll be on to something yeah but his new book Young Money a Field Guide to Wealth and Purpose in your 20s 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 2627 when he wrote it 2728 2728 last year of your 20s yeah so I really found it a fun enjoyable read about a space that I normally don't plan 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 13 yeah 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 to mid 20s yeah so I mean we talked about the spacked trading thing earlier but like when I was 23 mainly 23 and a little bit 24 my life basically looks like this it was you roll out of bed throw out some sweatpants grab check for late for breakfast and then you're just like kind of responding to like slack messages your own zoom calls spreadsheets power points and you're doing all of your bedroom and it'd been like that for well over a year and then on the side like you were over like you know trading options before we jump on this I had like my work laptop here and then I'm a personal laptop here it's like huh interesting like this that just got announced 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 spec and you're you can't even sleepstrings your future's taking my lose $100,000 and so I was almost in this like self-unuous holding cell 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 24 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 house spending my time at all I was kind of like a prisoner to like work and covid and stock market 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 100 so nobody's looking over your shoulder at what you're doing you could come and go as long as you got your work done whenever however everybody was fine yeah 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 but what was fascinating as I was reading this because I started out trading is 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 position for you hey I got to go leave for 10 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 have no other bandwidth for anything else 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 and exhausting yeah and like 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 gonna leave it in a year and it was just like all of these things came to a head and I was like okay like let's be really intentional here about like how do I want to spend like if I know I'm gonna 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 gonna leave to go do something else is it like keep like try to like trade back the money I just lost on that trade gone wrong I think I kind of want 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 head 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'm gonna bar Salota you hit the eject button you the concept of time comes up over and over throughout the book both generally and specifically one of the things you you write about is defining decades differently and about the opportunity cost of your 20s a lot of people who just buckle down and grind it out through their 20s you say that for many people that's a trap smart 20 something's falling to discuss that so I and I think this is especially true in the like call it hyper competitive at 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 early 20 something high paying job but you're also objectively pretty stupid you don't know anything you like don't like no 22 especially guys we're all pretty stupid yeah and and tell me when I get to grow out of that I don't know I mean you tell me um you're sitting there it's like okay like what am I supposed 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 a 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 bum 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 do this you almost become instead of being like the protagonist of your own life you're just kind of like filling a pre-ordained role like you're almost like an actor right that's how I think about it and in someone else's play right and I think the thing like I think the implicit bet people make when they do that is I will like earn enough money and have a level of stability where I can hit a jacks which you can do but you can't buy back the opportunities that you would have had in your 20s when you're in your like mid 30s 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 50s 60s 70s not in their 20s so kudos to you for getting there to tell us what what led you to that conclusion and and how much did the pandemic lockdown accidentally lead to these insights 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 on a normal day to day and I got 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 whole just being like kind of 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 like I mentioned like the second chapter of the book I used to be terrified of flying and like where 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 into the pandemic for ski trip.
The plane 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 Kansas City and I was just sitting there thinking the whole time we're totally going down we're going to die like I'm 23 it's over I'm dead and we obviously landed I didn't die but like again totally random but just something about that put that thought back my mind like well like at some point you are going to die it's not like up until that I just thought I was going to live forever like that's not stupid but um you don't really think about that in your 20s when most people in their 20s they're immortal you're not thinking about well one day I'm going to die 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 I want to do with it and so it's like a complete flute 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 a nurse you kind of do its thing and it was that like call it like awareness and 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 be a don't be like a passive participant in your own life. The difference between money and time is that money is both infinite and fungible time is neither. This is a philosophical concept. I consider myself a bit of a philosopher.
Okay I'm with you I'm there with you. What's your conclusion when you realize that money is both infinite and fungible? 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. So your point earlier you can kind of scrape behind your 20s maybe early 30s 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 financial advice 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 25 and not be rich if it means like spending money on fun stuff with your friends right. So you're not a fan of the fire movement the early retirement movement.
Not when it's taken to be extreme. I think that the core idea of like having enough money saved up or 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 yeah that when you're like over optimized for fire and your whole thing is like I want to opt out of work you're probably gonna hit that and your like early 40s when all of your peers are peak work you're not gonna be able to relate anybody after every year. So there's a lot of I think when you take the fire movement too far there's like social cost to that that are harder to see when you're looking at a spreadsheet but it's just like and you have to forego so many things you would probably prefer to spend money on in your 20s and 30s to hit that.
It's just not I don't think you should like go into crazy debt and you should max out your 401k 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. No that makes a lot of sense. I love this quote many of life's adventures are adventures only because you're 22 and broke and stupid and you're surrounded by other broke stupid 22 year olds. This is a feature not a flaw of being young lean into it.
Yep. Tell us about how you you saw that. What is it about being 22 and broken stupid that has to be embraced. So like I mean I spent that whole year of being I guess I was technically 24 but I was with a lot of 22 year olds who were like this whole like hostile hopping thing is 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 23 to 26 year olds who worked for a couple years and took a break and you're all just like in Buckbeds 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 like want to go from Seville Spand to Paris and they're trying to game out like it's $200 to fly but if we take a train ticket and sleep at a train station for six hours we can get there for $12 and or avoid a hotel room.
Right and if one of them would tell them to extend our European trip like eight more days right so or you have like and you did that right you went from Barcelona to where in Europe. I mean I I covered I was there from August to December and then I went to Latin America a month later for a few months and back to Europe and then August to December thing I think I went to like 19 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 Prague next you want to come and I was like sure sure I mean this guy Prague he's like yo I heard Budapest is great I'm like all right and then somebody's like we're gonna crack Al Polin next I've had a kid at a hostile crack Al who pitched me on his startup in San Francisco a year ago like talk about small world stuff but it was just like I went like pure optionality for a year and it was just like anybody I'm interesting was doing something cool I'm gonna go with them like oh I heard trons of Norway you can see the northern lights let's go dog sledding up there and like to do that so the ability to just like cast a really wide net because when like cheap thrills are like having to sleep on a train or like have a buck that 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 on 20s now but that would just not awful like I don't want to be on a roof like 12 strangers and worry about my stuff getting stolen that sounds terrible 24 you got nothing to get stolen anyway I got one they got to take my backpack I had a couple of exartes shirts and flip-flops sick like I'll go play poker and win 20 bucks I can buy another one it's fine so and there's versions of that play out everything right like I don't think everybody has to go backpack Europe but like you got a San Francisco there's like 24 year old startup founders that are sleeping in the office with a bunch of their bodies and they're having a blast like they're in objectively like horrid living conditions they don't even notice because they're like 23 or 22 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 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 so my my like more specific take on that is you shouldn't bank your income on a finger passion or about the example that I give is like I love writing it's a it's a thing like I've enjoyed I'll do the rest of my life whether it's books blogs like it's something I'll always incorporate um my like initial job out of business school was columnist podcast or media guy like a effectively media startup and I actually found it stressful where like every single day I like put something out and then I also was sitting there thinking this is draining the thought of like writing I wasn't monetizing my blog it was just the 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 like chasing your passion is one a lot of passions aren't that lucrative too the second your paycheck is dependent on you're doing that thing over and over again it can start feeling more like it's sure they're like fun so the the actual advice I have is like pursue stuff that you're pretty interested in that can pay you whether or not your 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 like having inclination for have some skills at go do that for a career and then use that like subsidize your ability to work on the fun stuff like I you know like writing books and blogs like I think I want to do independent of the financial outcomes from it I 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. Last question before we get to our favorite questions that we ask all of our somewhat special guests. How do I know I'm making the most of my time?
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's different stages where when I was like 23 or 24 it was just doing dumb hospital hopping stuff and like getting drunk all the time or whatever and it was great now I get drunk a lot less at the time 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 making strides is like a source of like joy and personal achievement when I was in college and playing football like objectively sucks but like I like playing college football really sucks and anybody just played it will tell you that but it's like by the description of the workout routines and the six a.m. Win sprints and but but when you know deep into the season the coach tap rains we get in there yeah it's like it's like incredibly like fulfilled like it's like your walk on to be putting on scholarship and then like getting made to 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 so and a real sense of achievement yeah like it was a it was a hard thing and I'd like executed on it so 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 hung over like on a park mentioned Spain but you feel like you're living out in 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 further 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 use 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 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 I think just having a very very strong sense of like one of the most important things right now that bring me fulfillment and then going after those is the recipe to a good life and the sequel to this fine joy in the suck is a great could be I just calling middle age money once I get my 30s well you could do something every decade you have a built-in model your money slightly older money right middle age money you got a whole run of things yeah all right let's jump to our favorite questions that I ask even my somewhat special guests starting with um you're you're still young tell us about your mentors did anybody really help shape your career 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 going to push 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 a small private high school and thought I was d*** and then I got college and just got wrecked for a good year and I was like really faster stronger or you just didn't know the game as well and didn't have the skills or some combination like it was like I I I just had to get better it was like better shape better skill I needed to get stronger and just be able to like react to the game on the field way faster and I just wasn't the processing speed and the size one area people don't realize that the quality of play at the college level it's astounding we played so we played alabama in a little mercy we played alabama in Auburn in the same year my junior team I like you want to talk about seeing like like monsters 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 for a receiver who briefly a gambling problem he's back as a punt returner just we started on the punt team was getting duped out of his shoes 20 times because we punted so much me um but defense 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 workout like you will develop like you will catch up to the point like if you keep that workout that 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 gonna be an all-american but I was like a starter and was like a very solid player but I could have 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 um so football coach was 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 and published and then a year after that like I remember when he followed me back on Twitter I was flying from Seville Spain to Manchester England and I looked at my phone I was like oh this is really cool this is really cool and then uh when I moved to New York we like hung out in person at Cloud funds office and like like great guy um but I would say like as a somewhat career slash just aspirational him and uh Tim Urban were like my two favorite bloggers from the kind of like you referenced Tim Urban in the book but I think you referenced a piece of his and I was surprised you didn't reference the piece on optionality the sort of chart with the black lines yeah everybody steals it on Twitter 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 25 year project do I really have 25 years like what am I gonna be doing at age 90 all right maybe a 25 year project isn't the best thing for me or age 80 best thing for me to start um but I laughed at a lot of your references because I'm familiar with with many of them they're really really good so so you mentioned Morgan any other post college mentors you want to bring up yeah I mean I'd say my current boss Sam Lesson great guy I mean he's had a very cool career right like he like started a company in his 20s in Brooklyn ends up getting acquired by Facebook like had a successful career at Facebook um and then like co-founder of the Venture Fund I work at 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 20s 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 things go right like financial success um but like it's I don't know he he's done like a few different things and now like has like a objectively like if my lifestyle like life is set up kind of like his in my 40s I'll be very cool with that like he crushes so you mentioned Morgan's books um tell us what you're reading now what are some of your favorites so I just started reading this book called 1873 Yes um who won the Pulitzer for um 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 go it's how you like it's it's I'm about halfway through and it's it's like very good and interesting I mean the thing I've done this from time to time like I hadn't read much over the last year while I was working on that yeah it's a killer writing is a killer as someone who's read books I had so underestimated like I have much more respect for other authors after going through that exactly how you read books you can't blog you can't it just sucks up so much yeah yeah it's like all your free time goes to that um 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 300 pages of a thing so fascinating and with like 1873 like reading about the stock market speculation in the like Vienna Austria stock market in the 1870s and then you're just pattern matching that against like what I saw with retail investing in 2021 it's you just see like human behavior playing out cyclically 150 years ago is just really really interesting and like a you know totally different time and market and paradigm but it's the exact same thing Lord's Defineance was his first book that won the Pulitzer um I'm excited about that book any of the books you want to mention um the infinity machine the one about the Deep Mind Founders it was by Sebastian Sebastian Malaby I think anyway it's like as far as AIs another 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 a group of like British researchers who've been hold up and London the whole time kind of kickstart 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 together and how there was like a bit of a coup with an open AI and then Elon leaves it's just a really good job of framing like the current moment in time and how we got here um but those were like I read both of those or been reading both of those in the last month and a half they're great interesting what about streaming what are you watching or listening to give us your favorite hilariously on the like 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 friends or um like Tim Ferriss a 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 talk to but occasionally they'll have someone where I really want to hear that because I think they'll pull out good questions um like I don't like Michael Lewis on Tim Ferriss really good episode where it's there's nothing I listen to specifically streaming I did like that movie obsession I thought it was phenomenal it was the one that like what Megaviral out of indie film that would Megaviral out of nowhere um who directed it it's what it's the I can't 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 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 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 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 50 people reading it I think that especially with AI becoming more and more of a thing it's easy to like resume is becoming increasingly 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 100 different resumes with LLMs 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 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 assistants are really good like anybody can access them to build stuff so you're 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 undergrad it's still probably the right move just from like getting trained on how to work hard people who work in gold from 22 to 24 they're typically more competent than other people and for all my stuff about like you should go take risk in your 20s the caveat on that is like you should have a couple of prestige snaps first like Columbia Business School was a prestige snap 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 in 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 snaps before you go jump off and do your own thing 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 challenging so my the status thing so nuanced I think that if you treat status as an end to itself you're gonna be incredibly disappointed I think if you treat status as a thing that like you can acquire and leverage to actually do it all yes like if the trade is I'm gonna go to an incredibly competitive school and spend two to four years working in some version of like Goldman Blackstone, McKinsey, 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 10 or 15 years into their career never really figured out their things or kept chasing status as like a vanity project makes 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 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 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 or like more and more of a thing passive investing is more and more of a thing you could argue that true like 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 quarter by 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 GameStop I thought was a one-off loop it wasn't like open door short-sweez out of nowhere you're seeing like random companies will just pop off like 500 percent which makes it a Dan Sondheim was on a podcast with the call of some brothers the strike founders a couple months ago he was talking about how they changed like how they position their shorts now do you want capital because you just you can be fundamentally right but guess what fundamentals don't matter if the borrower hits through the roof and the stock like 8x is and you get blown up right like like ask the game the Melvin Capital guy about fundamentals when it's fun got blown up right like at the end of the day the only thing that matters is making money and I I really thought a lot of that was a 2020-2021 thing and it was covid and people were at home we're seeing so much stuff with like random speculative like nuclear company ochre went public through a spack like a Sam Altman backed company it was worth like 40 billion dollars I don't think they have a functional reactor yet like are you suggesting that sites like Reddit Wall Street bets still carry the influence they used to or has that attenuated and it spread out to 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 look at as a data source where I think if something spikes in 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 derivatives like retail investors getting in the market and then yapping about stuff online that's just never gonna stop right and it's so funny because everything old is new again back in the day of the Yahoo message boys like the way 90s yeah like iomega and and that sort of stuff nothing has changed it's just how much faster and it's like zero commissions now it's like them there's and it's in your pocket you know how let me go home and call my broker does it and now there's like oh yeah prediction markets and sports betting on your phone we have removed all friction from people putting money at risk to do stuff and we may regardless of how dumb or speculative in my bank and the speed of which you can communicate what you're doing is now also instantaneous and free so you just have people constantly going risk on whatever for whatever reason and everybody else knows it that's just that's only gonna keep accelerating except it kind of sounds like a very late stage bull market because of that 21 and we're right 22 is kind of a bear market then AI happens 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 can blow it up and somebody starts running another thing i just think it's gonna get more and more violent i have a pet thesis at the giant reset the giant fiscal stimulus and crash and recovery in 2020 was like a reset and extend to the bull market another five ten years it's but anyway um jack you were more than a somewhat special guest this was really great thank you for being so generous with your time we have been speaking with jack reince he is the author of young money a field guide to wealth and purpose in your 20s if you enjoyed this conversation well check out any of the 653 we've done over the previous 12 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 and Aluca is my podcast producer i'm Barry Brittoldt's you've been listening to masters in business on Bloomberg radio