Latest / Masters in Business / Optimizing Life and Finances with Jack Raines
Transcript
- 0:02Speaker 1: Bloomberg Audio Studios, Podcasts, radio News. This week on the
- 0:08Speaker 1: podcast My Somewhat Special Guest, Jack Rains is a venture
- 0:12Speaker 1: capitalist and author. I've been reading a substack for a
- 0:16Speaker 1: couple of years and always found it quite entertaining and interesting.
- 0:21Speaker 1: His new book Young Money, A field Guide to Wealth
- 0:24Speaker 1: and Purpose in your twenties, is really interesting and wise
- 0:28Speaker 1: beyond its years. I wish I had access to a
- 0:31Speaker 1: book like this one hundred years ago when I was
- 0:33Speaker 1: in my twenties. I thought this conversation was fascinating. I
- 0:37Speaker 1: think you will also, with no further ado, my interview
- 0:40Speaker 1: of Jack Rains. Jack Rains, Welcome to Bloomberg.
- 0:52Speaker 2: I mean, the extra special guest is way too kind,
- 0:54Speaker 2: but so my special guest, my normally special guest.
- 0:58Speaker 1: I wouldn't want to call him like my young guest.
- 1:01Speaker 1: My you know, I painted myself into the corner with
- 1:04Speaker 1: extra special guests. Why once you go that way, you
- 1:07Speaker 1: can never go back.
- 1:08Speaker 2: I'll take it.
- 1:09Speaker 1: Here's my special guest. Really, what's wrong with Jack? He's
- 1:12Speaker 1: a special were a cowboy hat? That's right. Well we'll
- 1:15Speaker 1: get into that a little bit. So let's roll back
- 1:19Speaker 1: so many years ago to when you're undergraduate studying finance
- 1:23Speaker 1: in Spanish while playing football and mercer. That was before
- 1:27Speaker 1: you got your MBA from Columbia. Was there ever a
- 1:30Speaker 1: career plan?
- 1:32Speaker 2: Like, not really, it was just I don't know. I
- 1:35Speaker 2: feel like basically every white dude ends up studying finance
- 1:38Speaker 2: unless they're dead set on going to like med school,
- 1:40Speaker 2: law school, or like computer science. So it was study finance,
- 1:44Speaker 2: and then I was set to graduate in two and
- 1:48Speaker 2: a half years because we had to take summer classes
- 1:50Speaker 2: with football, and I was like, I should double major
- 1:53Speaker 2: finance and marketing is stupid. I don't like computer science.
- 1:57Speaker 2: Let's pick up Spanish because it feels like that could
- 1:59Speaker 2: be marginally used living in the South. Spanish is very
- 2:03Speaker 2: assiassi right now, but it's like sufficient. There was no
- 2:06Speaker 2: real career path other than figure it out from there.
- 2:11Speaker 1: That's intriguing. I'm cracking up because they have so many
- 2:15Speaker 1: different ways to go with this. First gig out of
- 2:19Speaker 1: school was a corporate finance at UPS, which you described
- 2:25Speaker 1: as mostly moving a mouse around the screen and trying
- 2:27Speaker 1: to look busy. Correct tell us about your experience in
- 2:32Speaker 1: corporate finance.
- 2:33Speaker 2: Yeah, I mean to set the stage a little bit.
- 2:35Speaker 2: I graduated in December twenty nineteen, which was probably the
- 2:39Speaker 2: worst possible date to graduate, given that COVID started like
- 2:43Speaker 2: three weeks after that. So I moved to Atlanta in
- 2:47Speaker 2: January or February of twenty twenty start working for UPS.
- 2:51Speaker 2: I'm in the office for three days, my computer isn't
- 2:53Speaker 2: even fully online yet, and then we're told that we're
- 2:55Speaker 2: going remote for one week and then one month, and
- 2:57Speaker 2: then everybody had the same experience where a year and
- 3:00Speaker 2: a half later you're still remote. So I don't think
- 3:03Speaker 2: it's great to be a twenty two year old who's
- 3:05Speaker 2: never had a real job who's then told you're going
- 3:07Speaker 2: to work from home while you have like your Xbox
- 3:10Speaker 2: and all of your friends like doing the same thing.
- 3:11Speaker 2: And it was actually like a terrible environment to like
- 3:15Speaker 2: start learning how to be a worker. And yeah, it
- 3:17Speaker 2: was just zoom calls, Excel sheets like modeling out fuel
- 3:22Speaker 2: cost projections and forecast for UPS for like twenty twenty two. Yeah,
- 3:27Speaker 2: I was honestly bored the whole time. And to build
- 3:31Speaker 2: on top of that, I had gotten to business school
- 3:33Speaker 2: out of undergrad so like Columbia, I went to business
- 3:36Speaker 2: school at Columbia, and they have a deferred enrollment program
- 3:39Speaker 2: where when you're a senior in college, you apply and
- 3:42Speaker 2: then you work a few years and go to business school.
- 3:44Speaker 2: So I knew that I was going to go to
- 3:45Speaker 2: grad school in like three years. Covid hit. I was
- 3:49Speaker 2: super bored working remote, just doing basically nothing, and it
- 3:53Speaker 2: just kind of felt like I was in a work
- 3:55Speaker 2: from home purgatory for about eighteen months.
- 3:57Speaker 1: So having that window where, hey, I know where I'm
- 4:01Speaker 1: going to be eighteen months from now in September of
- 4:06Speaker 1: twenty twenty blank, what led you to say, I think
- 4:10Speaker 1: I'm going to quit and just buy a one way
- 4:12Speaker 1: ticket to Barcelona and travel the world. Like that's a
- 4:17Speaker 1: giant leap, which not a lot of people have the
- 4:21Speaker 1: nerve to make. What led to that decision?
- 4:23Speaker 2: So, Like, when I was a kid, I always loved
- 4:26Speaker 2: to travel, and my grandparents would take me everywhere.
- 4:29Speaker 1: Your grandma took you on a crazy trip you described
- 4:32Speaker 1: in the book to Savannah in Africa.
- 4:34Speaker 2: Yeah. Yeah, when I was eleven, my grandma Mama roof,
- 4:38Speaker 2: she I'm the oldest grandkid in the family, and she
- 4:40Speaker 2: hit me with the idea that she wanted to take
- 4:42Speaker 2: me on a trip like anywhere in the world I
- 4:44Speaker 2: wanted to go. I actually didn't know if she literally
- 4:47Speaker 2: met anywhere. I wanted to go, somewhere crazy, like Africa
- 4:49Speaker 2: or Asia. And we lived in South Georgia. Initially I
- 4:52Speaker 2: pitched Costa Rica and she said, too, you can. Yeah,
- 4:55Speaker 2: she said, like, that's like a three hour flight. I
- 4:58Speaker 2: was like, okay, Like I thought the like I had
- 5:02Speaker 2: a big map in my room as a kid, I
- 5:03Speaker 2: thought it'd be cool to go to the Ngoragora Crater
- 5:06Speaker 2: and see Mount Kilimanjarro and all this stuff. So she
- 5:09Speaker 2: took me and we went, and we went on a
- 5:11Speaker 2: two week safari and it was awesome. And then in
- 5:13Speaker 2: college I studied abroad in Spain. One summer, I went
- 5:16Speaker 2: to France. One summer with my best friend from college,
- 5:19Speaker 2: I did a service trip to Ecuador. Like I always
- 5:22Speaker 2: loved leaving the US, and it was kind of a
- 5:25Speaker 2: thing in the back of my head where I knew,
- 5:27Speaker 2: at some point in my twenties it would be really
- 5:29Speaker 2: fun to do like a multi month trip abroad with
- 5:31Speaker 2: like no itinerary other than just see other stuff. And
- 5:36Speaker 2: I was sitting there, It's like you have this, You're
- 5:38Speaker 2: working remote for eighteen months on your board, and then I,
- 5:42Speaker 2: for better or worse, had a fortuitous run trading spacks
- 5:45Speaker 2: and spack warrants during the pandemic, which gave me enough.
- 5:49Speaker 2: It gave me more money than I expected to have
- 5:51Speaker 2: at twenty three or twenty four, where I was like,
- 5:53Speaker 2: I mean, I I don't it wouldn't cost that much
- 5:56Speaker 2: to just go hostile hop Europe in Latin America for
- 5:58Speaker 2: a year.
- 5:58Speaker 1: Yeah, I'm glad you were up. You're not a trust
- 6:01Speaker 1: fund budd it, but baby, in any stretch of the imagination, no,
- 6:04Speaker 1: you scrape together some money, you fly coach, you staying
- 6:08Speaker 1: in hostels. You have ten roommates in these.
- 6:11Speaker 2: Places, eating like McDonald's or Euros or whatever. Every day.
- 6:14Speaker 2: It was the best. I mean, I got food poisoning oneside,
- 6:16Speaker 2: It was fun. It was fun.
- 6:19Speaker 1: The more recently, you wrote a story about going to
- 6:22Speaker 1: someone's winning and I think it was India and a
- 6:25Speaker 1: bunch of people got food poisoning and it was hilarious.
- 6:29Speaker 2: It feels a little bit like India right now in
- 6:30Speaker 2: New York. It's like the air quality today as of
- 6:33Speaker 2: recording is pretty similar.
- 6:34Speaker 1: To those Canadian fires. Are you walk out, it smells
- 6:38Speaker 1: like a bar because it's yellow.
- 6:40Speaker 2: It's like for microdosing New Deli era. Right now, it's great,
- 6:43Speaker 2: it's good stuff.
- 6:44Speaker 1: Only without the e coli that you described. But let's
- 6:50Speaker 1: bring it back to your career. So, so you do
- 6:52Speaker 1: this trip, you go through a couple of dozen countries,
- 6:56Speaker 1: you meet people that you're still friendly with. It was
- 6:59Speaker 1: really fascinating, and you get to business school. How do
- 7:03Speaker 1: you adjust? How do you make that transition?
- 7:06Speaker 2: Yeah? It was. It was interesting. Like I in the
- 7:08Speaker 2: back of my head, I kind of knew I had
- 7:10Speaker 2: this start date moving to New York in August twenty
- 7:13Speaker 2: twenty two. So I eventually quit my previous job, first
- 7:17Speaker 2: job out of college in August twenty one. It was
- 7:19Speaker 2: kind of like, all right, let's spend a year and
- 7:22Speaker 2: just have as much fun as physically possible, knowing that
- 7:25Speaker 2: then we're gonna go to grad school. Then we'll do
- 7:27Speaker 2: our career in New York and YadA, YadA, YadA. It
- 7:30Speaker 2: was funny because it was at first weird, like being
- 7:33Speaker 2: like I spent basically a full year out of the country,
- 7:35Speaker 2: jumping around a lot, and then you're in New York
- 7:37Speaker 2: and you have like a home base and you have
- 7:40Speaker 2: a business school. Is not a particularly strenuous thing, but
- 7:43Speaker 2: you do have a set schedule where you have classes
- 7:45Speaker 2: and stuff. I loved it though, I mean, I love Columbia, honestly,
- 7:50Speaker 2: I love New York in general, best city in the world,
- 7:53Speaker 2: particularly in your twenties. And it took a couple of
- 7:57Speaker 2: months to really get in the flow of like living
- 7:59Speaker 2: here and then also like you're meeting hundreds of new
- 8:01Speaker 2: people like that, but actually getting integrated not hard. It
- 8:06Speaker 2: felt like a perfect.
- 8:06Speaker 1: Fit, really really interesting. So I'm curious. You learn a
- 8:11Speaker 1: lot of things in both your office career or remote
- 8:16Speaker 1: work from home career and business school. What did you
- 8:20Speaker 1: learn about finance, money time while you were traveling.
- 8:25Speaker 2: I mean, the biggest thing that really jumped out was
- 8:29Speaker 2: It's something I write about a lot in the book,
- 8:30Speaker 2: like the I call it the stage specificity of life.
- 8:34Speaker 2: But by that I mean that it's pretty easy to
- 8:38Speaker 2: conceptualize money, like what you're taught from like in high school,
- 8:42Speaker 2: how money compounds over time if you invest in and
- 8:44Speaker 2: it's you know, you should be frugal and save up money,
- 8:47Speaker 2: but what you miss is like what's the optimal time
- 8:50Speaker 2: to spend that money on different things? And the example
- 8:52Speaker 2: that I give a lot is like I was twenty
- 8:55Speaker 2: four and like sleeping in a bunk bed in the
- 8:56Speaker 2: hostel with twelve roommates or whatever, and it was actually
- 9:00Speaker 2: just a hilarious setup. Like it's just a bunch of nonsense.
- 9:03Speaker 2: You have a French guy here and then like a
- 9:05Speaker 2: Mexican girl here, and it's like half the a lot
- 9:07Speaker 2: of the dorms are co ed, and it's like it's
- 9:09Speaker 2: like summer camp for like young adults. But then occasionally
- 9:12Speaker 2: you meet somebody in their like early thirties staying in
- 9:14Speaker 2: the same hostel and it's like you can almost tell
- 9:18Speaker 2: that they noticed they're like probably six or seven years
- 9:22Speaker 2: too late to have done that type of trip. And
- 9:24Speaker 2: like the biggest takeaway from traveling was like if I
- 9:27Speaker 2: really wanted to do this trip, this was the like
- 9:30Speaker 2: this was the right window to do this. Like I
- 9:31Speaker 2: optimized like that phase of my life correctly for somebody
- 9:34Speaker 2: who wanted to do that type of thing. And that's
- 9:37Speaker 2: kind of what stuck with me the most after is
- 9:40Speaker 2: not just being aware of what you want to get
- 9:42Speaker 2: out of life, but like what things have deadlines, where
- 9:46Speaker 2: like if that window of opportunity closes, you're just not
- 9:49Speaker 2: gonna be able to maximize your like fulfillment or enjoyment
- 9:52Speaker 2: or utility from that experience. Like every basically everything you
- 9:55Speaker 2: do in life has an expiration date for when you
- 9:58Speaker 2: would enjoy the most you can.
- 10:00Speaker 1: You can go cheap and cheerful in your twenties, maybe
- 10:03Speaker 1: even early thirties, but not much past. Correct, So you
- 10:07Speaker 1: were also writing before the trip and during the trip.
- 10:10Speaker 1: Tell us a little bit about your experience, what you
- 10:13Speaker 1: discovered about yourself as you're writing, and why you thought
- 10:17Speaker 1: that might be a career path.
- 10:18Speaker 2: So like, Hilariously, when I was doing the whole spac
- 10:21Speaker 2: trading thing in twenty twenty and twenty twenty one, I
- 10:23Speaker 2: had a burner Reddit account called Barmelo's Anthony. It's a
- 10:28Speaker 2: play on words on Barmelo, Carmelo, Anthony, and xanax bars.
- 10:32Speaker 2: It was my name of my college group me. We
- 10:33Speaker 2: all had edgy like drug related famous person combination names.
- 10:38Speaker 2: I was writing so much stuff about, Like, oh, like
- 10:43Speaker 2: Apollo changed the background header of their website from oil
- 10:46Speaker 2: rigs to windmills. I think they're going to take an
- 10:48Speaker 2: ev company public through a spack And then they announced
- 10:50Speaker 2: a deal with Fiscarado motive. Three weeks later it was
- 10:53Speaker 2: like borderline conspiracy theory stuff, but it worked a lot
- 10:56Speaker 2: of it worked. Yeah, So I like always liked just
- 10:59Speaker 2: writing about like stuff I was seeing going on in markets.
- 11:02Speaker 2: And then when I was when I was traveling, I
- 11:05Speaker 2: tried to get hired by The Morning Brew, the Hustle,
- 11:09Speaker 2: a few different like kind of upstart ish media companies.
- 11:12Speaker 2: Nobody would hire me for lack of like professional writing experience.
- 11:16Speaker 2: So I just started writing, like I just launched a
- 11:18Speaker 2: sub stack and started writing a newsletter. And it was
- 11:20Speaker 2: like half investing in finance and half travel blog, like
- 11:25Speaker 2: detailing everything I was doing day to day, who I
- 11:27Speaker 2: was meeting, and I just enjoyed it, Like it's writing
- 11:30Speaker 2: something I've always found fun. I've always found it a
- 11:32Speaker 2: bit cathartic, like putting your thoughts on paper, and it's
- 11:35Speaker 2: a good I don't know, I think it's like a
- 11:37Speaker 2: good exercise for anybody to really like distill what you
- 11:41Speaker 2: think about a thing is try to sit down and
- 11:43Speaker 2: put pin on paper.
- 11:44Speaker 1: So Daniel Borston, the Librarian to Congress is famous quote,
- 11:49Speaker 1: I write to figure out what I think.
- 11:51Speaker 2: Yep.
- 11:51Speaker 1: And besides, at that hour, the bars were all closed.
- 11:54Speaker 2: Yep.
- 11:55Speaker 1: So you know, until you put it down, until you
- 11:58Speaker 1: put pen to paper, a finger to keyboard, it's sort
- 12:02Speaker 1: of nebulous and not distinct. Once you write it there
- 12:06Speaker 1: it is black and white. Yeah. Yeah, so for sure.
- 12:09Speaker 1: So you come out of Columbia, what's the first gig
- 12:13Speaker 1: you're doing while you're while you're a new grad.
- 12:16Speaker 2: So, so to step back a little bit, when I
- 12:18Speaker 2: was still in business school, I kind of had this like,
- 12:21Speaker 2: I think investing in financial markets are interesting. I really
- 12:25Speaker 2: like writing. I had like monetize my newsletter fairly well
- 12:29Speaker 2: selling ads, and I was kind of trying to figure
- 12:31Speaker 2: out which way I wanted to lean with it. And
- 12:33Speaker 2: then I had some publishers who were like loosely interested
- 12:35Speaker 2: in me maybe writing a book. So I wanted to
- 12:37Speaker 2: leave the book writing door open. And I interned for
- 12:41Speaker 2: a venture capital fund called Red Point Ventures my first year,
- 12:45Speaker 2: helping them with like building up a newsletter and like
- 12:48Speaker 2: editorial strategy and all that stuff. It was like love
- 12:52Speaker 2: the team there, it was great. My takeaway from that
- 12:54Speaker 2: was I should either like go do media or I
- 12:58Speaker 2: should like push you get in like investing seat somewhere,
- 13:01Speaker 2: not split the middle and do like the marketing arm
- 13:04Speaker 2: of an investment group. So going into my second year,
- 13:08Speaker 2: Sam Row, you know, Front of the Show. He was
- 13:11Speaker 2: like contracted by Robin Hood to help them with the
- 13:14Speaker 2: hiring for they were building out a media subsidiary called
- 13:17Speaker 2: Sherwood News. We grabbed coffee and he was like, I
- 13:21Speaker 2: don't know what your plan is after business school. I
- 13:23Speaker 2: think you'd be a good fit with what they're building here.
- 13:25Speaker 2: And he started telling me about it, and it checked
- 13:27Speaker 2: a lot of boxes of like, on one hand, it
- 13:30Speaker 2: was kind of an upstart new media thing with like
- 13:33Speaker 2: I would have a lot of autonomy. On the other hand,
- 13:35Speaker 2: we were surrounded by the structure of like a big
- 13:37Speaker 2: fintech company, so, like media is a tough business these days,
- 13:40Speaker 2: and there was a lot more stability there from like
- 13:42Speaker 2: financial backing.
- 13:43Speaker 1: Tell me about having a media outlet attached to a
- 13:47Speaker 1: large fintech or data services company.
- 13:50Speaker 2: The entire pitch was just trying to like basically make
- 13:52Speaker 2: a new Age Bloomberg tell you the truth.
- 13:54Speaker 1: Did you guys get any hood stock?
- 13:57Speaker 2: Yeah? Yeah, yeah, so not.
- 13:59Speaker 1: Terrible, not terrible.
- 14:00Speaker 2: I mean the issue was I only worked there for
- 14:02Speaker 2: a year, so it's not like I got that much
- 14:03Speaker 2: but like it. Yeah, like I wish I would have
- 14:06Speaker 2: I wish I would have gotten more, and I wish
- 14:08Speaker 2: I would have stayed longer had I gotten more, is
- 14:11Speaker 2: the takeaway from that. But yeah, I ended up ended
- 14:13Speaker 2: up joining them during my second year. I signed the
- 14:15Speaker 2: book deal for that book the summer after I graduated.
- 14:18Speaker 2: It's about two years ago now, and then I was
- 14:20Speaker 2: sitting there and I just like everything was fine. But
- 14:24Speaker 2: I realized after working in a like more structured media environment,
- 14:29Speaker 2: I actually like like I like writing a blog. I
- 14:31Speaker 2: like kind of free range putting stuff on the internet,
- 14:34Speaker 2: but like I didn't like the actual like like call
- 14:36Speaker 2: it nine to five employed version of like financial media,
- 14:40Speaker 2: and my like it kind of clicked to my head
- 14:43Speaker 2: that when I was at that point of investing thing
- 14:45Speaker 2: versus like media, I actually probably should have gone investing track,
- 14:49Speaker 2: but I was so hyper focused on like I don't
- 14:52Speaker 2: want to kill a potential book deal momentum and this
- 14:54Speaker 2: and that that I took the other one and I
- 14:56Speaker 2: had like a total career panic, like to almost too
- 15:00Speaker 2: most two years ago, like fall twenty four.
- 15:02Speaker 1: And there is something to be said about the daily
- 15:04Speaker 1: beast that must be fed when you're on a regular deadline,
- 15:08Speaker 1: Like that's tough. Yeah, no, it's brutal. And it's why
- 15:11Speaker 1: there's so much content that's so useless, because hey, there
- 15:15Speaker 1: are minutes and hours to fill in column inches and
- 15:21Speaker 1: the infinite more of the Internet. I mean, it just
- 15:23Speaker 1: never stops. So that's why we have this fire hose. So,
- 15:28Speaker 1: so you had done Young Money as a sub stack,
- 15:33Speaker 1: you had done Sherwood for Robinhood. I'm kind of fast
- 15:37Speaker 1: anybody in an essay you did how I lost one
- 15:39Speaker 1: hundred and fifty thousand dollars in a day trading SPACs
- 15:43Speaker 1: yep way back in twenty one. Tell us about your
- 15:47Speaker 1: ramp up in the spac world and then the blow up.
- 15:50Speaker 2: Oh it was, I mean it was awesome, like like
- 15:52Speaker 2: I like I was. I don't know if you would
- 15:55Speaker 2: have checked my pulse or stress levels at that point
- 15:58Speaker 2: they were through the roof, but like it was crazy.
- 16:00Speaker 2: So it's like, right when the pandemic hit, I thought
- 16:04Speaker 2: I was like the next Michael Burry. I had like
- 16:06Speaker 2: ten thousand dollars in my checking account, threw it all
- 16:09Speaker 2: in spy puts. They tripled because obviously the market was
- 16:12Speaker 2: going to take and I was like, yeah, I'm him,
- 16:15Speaker 2: and then you know Bill Ackman. A week later, it
- 16:17Speaker 2: was like crying on CNBC say the world's going to hell,
- 16:20Speaker 2: and I was like, SMP's going to like a thousand,
- 16:22Speaker 2: let's do it again, let's buy more puts. You know,
- 16:25Speaker 2: I actually, having not really been an adult during eight
- 16:29Speaker 2: I completely underestimated like the FED and quantitative easy.
- 16:32Speaker 1: And how that could work and how fast that turn is.
- 16:35Speaker 2: Like I my face got melted off. I shortened the
- 16:38Speaker 2: actual bottom and then I basically round tripped ten thousand
- 16:41Speaker 2: dollars to thirty back to ten. I have my tailtop
- 16:43Speaker 2: between my legs and I was like, I'm never trading
- 16:45Speaker 2: a stock.
- 16:45Speaker 1: Did you ever feel the need to reach over to
- 16:47Speaker 1: the waste paper basket and throw up? No?
- 16:50Speaker 2: But like if it had been bigger numbers, maybe, so
- 16:53Speaker 2: I'm like, I'm never going to trade stocks again. I
- 16:55Speaker 2: put six thousand dollars in. I opened like a roth
- 16:57Speaker 2: Ira do my one contribution first years a you know,
- 17:00Speaker 2: adult working, and I don't look at it for a month.
- 17:04Speaker 2: And then in May my friend Jake Buddy from undergrad
- 17:07Speaker 2: was like, do you know what a spack is? I
- 17:10Speaker 2: say no, and he's like, well, if you buy this
- 17:12Speaker 2: Desert Eagle spack, It'll turn into DraftKings stock in like
- 17:16Speaker 2: two months. And I was like, it's like like an ipo,
- 17:19Speaker 2: and he's like, I don't know, dude, I just saw
- 17:20Speaker 2: on the internet. If I buy this, you owned Draft Kings.
- 17:22Speaker 2: And I was like, okay, I went now the rabbit
- 17:25Speaker 2: hole was looking at it, and it's like.
- 17:26Speaker 1: And it's a pars. It's before it comes out. It
- 17:29Speaker 1: was it trading? It was it did trade up.
- 17:32Speaker 2: It was trading because so the par on most spacks
- 17:35Speaker 2: is like ten dollars, and it was trading at like
- 17:37Speaker 2: twelve or thirteen. Oh really maybe fifteen. But the warrants
- 17:40Speaker 2: had like doubled or tripled, right, because all the warrants
- 17:42Speaker 2: have a strike price of eleven fifty. So then I
- 17:45Speaker 2: had like traded options enough. I understood like strike prices,
- 17:49Speaker 2: expiration dates, whatever. And the thing that jumps out was
- 17:52Speaker 2: that warrants don't expire for five years and they have
- 17:54Speaker 2: an eleven fifty strike price. So I was doing the
- 17:56Speaker 2: math and I watched DraftKings. After the merger happened, it
- 17:59Speaker 2: ran out to the warrants ran up to eight or
- 18:01Speaker 2: nine dollars. You would have doubled on the stock. We
- 18:04Speaker 2: would have made like nine x on the warrants if
- 18:06Speaker 2: you bought them at a dollar, like at peak pandemic collapse.
- 18:09Speaker 1: So I was like, okay, if like this is easy, well,
- 18:12Speaker 1: I was.
- 18:13Speaker 2: Just like spacks obviously kind of seemed like a bubble
- 18:15Speaker 2: right now, because there'd been like Nikolai Motors had announce
- 18:18Speaker 2: a Spack and there were a couple of others, and
- 18:19Speaker 2: I was just like, I bet that this thing is
- 18:22Speaker 2: gonna like this is just gonna be a game for
- 18:24Speaker 2: a little while. And if I can just pick the
- 18:26Speaker 2: spack warrants early, I bet I can make money. So
- 18:28Speaker 2: Nicola warrants to trade at three dollars, I bought six
- 18:31Speaker 2: thousand dollars worth. I made like twelve grand a couple
- 18:33Speaker 2: weeks later, and then I just kept rinting and repeating
- 18:36Speaker 2: spack warrants, and like six months later, I got from
- 18:39Speaker 2: six grand to one hundred and fifty grand, and I
- 18:41Speaker 2: was like, this is so easy.
- 18:42Speaker 1: So then I, by the way, oh that that should
- 18:46Speaker 1: immediately set bells off.
- 18:48Speaker 2: I doubled down, though it didn't set off any bells,
- 18:50Speaker 2: because then I was like, okay, it did set off
- 18:53Speaker 2: one bell. I was like, warrants are risky, and if
- 18:55Speaker 2: any of these deals collapses, the warrants go to zero,
- 18:58Speaker 2: I should start buying the shares close to NAV as possible.
- 19:01Speaker 2: So I was in like an online discord chat with
- 19:04Speaker 2: a lot of other anonymous people. We built some web
- 19:06Speaker 2: scrapers that will pull every spac SEC filing, so as
- 19:10Speaker 2: soon as the filing hit the press, like trading halts,
- 19:13Speaker 2: when news comes out for a spec, I would get
- 19:15Speaker 2: a push notification, open up the deck, skim it. If
- 19:18Speaker 2: it was electric vehicles, marijuana, outer space, sports, betting, or
- 19:23Speaker 2: renewable energy, I would go all in unless the unless
- 19:27Speaker 2: the like valuation of the deal was just egregious, I
- 19:29Speaker 2: would go all in. And I knew that the stock
- 19:32Speaker 2: would probably pop like at least thirty or forty percent,
- 19:34Speaker 2: because they just did every time. So you get in
- 19:38Speaker 2: an eleven, your max loss is probably like five percent
- 19:41Speaker 2: on any trade, and you sell it fourteen or fifteen,
- 19:44Speaker 2: so you're basically risking five percent to make forty percent.
- 19:47Speaker 1: Of asymmetrical risk reward. That's what you want.
- 19:49Speaker 2: And I did that like seven times in a row,
- 19:51Speaker 2: and then I went from one fifty to four hundred
- 19:53Speaker 2: and like I'd only risked on any given trade, like
- 19:55Speaker 2: five percent of my portfolio, and they didn't all hit,
- 19:58Speaker 2: but like enough did that it didn't matter. And my dad, obviously,
- 20:01Speaker 2: I kept telling him what I was doing, and I
- 20:03Speaker 2: hit like it was February twenty twenty one, and he
- 20:06Speaker 2: called me and he was like, you should probably just
- 20:08Speaker 2: sell and just put it in like an index fund.
- 20:10Speaker 2: And I was like, I knew this two more times,
- 20:12Speaker 2: I'll have a million dollars at twenty four. I'm pretty
- 20:14Speaker 2: sure I can get there. That should have been the.
- 20:17Speaker 1: Screen is the bell ringing that?
- 20:19Speaker 2: And then when he and his brother were talking to
- 20:21Speaker 2: me about potentially managing some of our family's money. You
- 20:24Speaker 2: shouldn't have your twenty four year old kid, he just
- 20:26Speaker 2: made six thousand percent trading spacks, touching your grandparents like
- 20:28Speaker 2: retirement money. I did not, thankfully. I said, I don't
- 20:31Speaker 2: feel comfortable doing that. I'm okay. I was self aware
- 20:33Speaker 2: enough to know that would have been a bad idea.
- 20:36Speaker 2: So getting to how I lose the money at this point,
- 20:39Speaker 2: way too many spacks. Shaquille O'Neil has a spack, Paul
- 20:42Speaker 2: Ryan has a spack. Like everybody and their mother has
- 20:44Speaker 2: a spack and the bubble didn't pop. It just stopped
- 20:48Speaker 2: bubbling because there there was kind of this pool of
- 20:50Speaker 2: money that was chasing every hot spack and then there's
- 20:53Speaker 2: like one hundred of them on the market. Somebody announce
- 20:55Speaker 2: is a deal, the terms are getting worse and worse,
- 20:57Speaker 2: and the value.
- 20:58Speaker 1: You're watching this to k in real time.
- 21:00Speaker 2: Yeah, And it was like by April May of that year,
- 21:03Speaker 2: it's getting tougher and like a deal would get announced
- 21:06Speaker 2: might jump ten percent. You're just I was like I
- 21:08Speaker 2: was addicted to the rush. So there was a buy now,
- 21:12Speaker 2: pay later company called Catapult. Eighty percent of the revenue
- 21:15Speaker 2: came from Wayfair, obviously a pandemic darling. And this is
- 21:19Speaker 2: at the time when Square bought After Pay for like
- 21:22Speaker 2: thirty billion dollars crazy price. A firm went public at
- 21:25Speaker 2: like a thirty billion dollar valuation, and like these companies
- 21:28Speaker 2: were growing slower than Catapult because Catapult was just a
- 21:31Speaker 2: derivative of Wayfair, which is a pandemic darling. They were
- 21:34Speaker 2: less profitable and I was just like, Catapult's gonna have
- 21:37Speaker 2: their earnings in August. They've had no cell side coverage.
- 21:40Speaker 2: I just need like one analyst from like Morgan Stanley
- 21:44Speaker 2: or whatever to initiate like a buy the stock's gonna double,
- 21:47Speaker 2: I'm gonna buy a bunch of warrants at like a
- 21:48Speaker 2: dollar fifty they're gonna rip. And then this thing, like
- 21:51Speaker 2: I'm gonna make a million dollars on this trade. This
- 21:53Speaker 2: thing had already gone public through a spac, Like there
- 21:55Speaker 2: was no floor, that deal was closed. It's just a
- 21:57Speaker 2: normal company.
- 21:57Speaker 1: So not your traditional spac trades that you've been doing.
- 22:01Speaker 2: It had gone public through a spack and it's just
- 22:03Speaker 2: like a normal company at this point. And I I
- 22:06Speaker 2: just aped into it with like three hundred I think
- 22:08Speaker 2: I had like three hundred and thirty thousand dollars at
- 22:10Speaker 2: that point. Just went all in and it started like
- 22:13Speaker 2: inching down and spike back up leading up to earnings,
- 22:15Speaker 2: like I had four different times I could have gone
- 22:17Speaker 2: out with like a ten percent loss, and I was
- 22:19Speaker 2: just like I was just pot committed to, like this
- 22:21Speaker 2: is gonna be the millionaire trade. They missed earning so
- 22:24Speaker 2: badly that the stock fell. I think the stock fell
- 22:27Speaker 2: twenty percent before market opened on like August eleventh, and
- 22:30Speaker 2: the warrants immediately got cut in half by like fifty.
- 22:33Speaker 1: Percent and that's one hundred and fifty grand.
- 22:35Speaker 2: Yeah, and I'm just I'm looking at it. I'm looking
- 22:37Speaker 2: at the like level two trading data, and there's there's
- 22:39Speaker 2: a big buy for like like one hundred thousand warrants
- 22:44Speaker 2: at a dollar or whatever, and then there's the floor
- 22:46Speaker 2: collapses under and I was like, huh, I'm just gonna like,
- 22:49Speaker 2: I'm just gonna sell to that entire bit and just
- 22:51Speaker 2: eat it, and like I'm getting out before like the
- 22:53Speaker 2: whole thing that's rug pulled, which was the right move
- 22:56Speaker 2: because I basically liquidated my position pre market from like
- 23:00Speaker 2: three hundred thousand dollars like one hundred and fifty or whatever.
- 23:02Speaker 2: And I was just like, man, that sucks, put in
- 23:06Speaker 2: the SMP, and then just went to the gym and
- 23:08Speaker 2: worked out for like real self loathing workout for three hours.
- 23:12Speaker 1: You know that that sort of big wackage is a
- 23:15Speaker 1: rite of passage of anybody that's ever worked on a
- 23:19Speaker 1: trading desk. I don't care if you're at you're at
- 23:21Speaker 1: Jane Street or if you're day trading from home. Those
- 23:24Speaker 1: losses are just so seminal and so instructive and focus
- 23:29Speaker 1: you on, Hey, what's my risk management. What's my edge here?
- 23:32Speaker 1: What am I really doing? Swing for the fences? Am
- 23:36Speaker 1: I really putting fifty or one hundred percent of my
- 23:38Speaker 1: portfolio into one trade? That seems kind of like you
- 23:42Speaker 1: you you could read that in a book, but until
- 23:44Speaker 1: you've lived it, it's really challenging.
- 23:47Speaker 2: The issue for me was like the plan I had
- 23:49Speaker 2: initially of like buy spacks near navs, sell when they pomp,
- 23:53Speaker 2: was like a good strategy. And if I'd stuck with that,
- 23:56Speaker 2: even if it stopped working, it's like, Okay.
- 23:58Speaker 1: The down side is the minimus, we made.
- 24:00Speaker 2: A bunch of money, this trade doesn't work, just like
- 24:02Speaker 2: parking index fund until any right, yeah, and then like
- 24:05Speaker 2: either come up with something new or just stop. The
- 24:07Speaker 2: issue was I was so used to number going up.
- 24:10Speaker 2: I was kind of willing to bet the house I'm
- 24:11Speaker 2: doing it one more time, then I'm confident I hit
- 24:14Speaker 2: a million. I would have walked away like that was
- 24:16Speaker 2: just like a benchmark numbers.
- 24:17Speaker 1: Oh you should know that when you hit, you would
- 24:20Speaker 1: not have whiked away. Junkies don't say one more hit,
- 24:24Speaker 1: and gamblers don't say, I just need this parlay to
- 24:27Speaker 1: come in and then I'm good because you're always looking
- 24:30Speaker 1: for the for the dopamine, hit for the adrenaline.
- 24:33Speaker 2: I would have found something else to speculate on. But
- 24:35Speaker 2: I think I would have stopped trading SPACs had that happened.
- 24:38Speaker 1: Coming up, we continue our conversation with Jack Rains, discussing
- 24:43Speaker 1: Slow Ventures and investing in creators. I'm Barry rid Halts.
- 24:47Speaker 1: You're listening to Masters in Business on Bloomberg Radio. I'm
- 24:52Speaker 1: Barry Ridults. You're listening to Masters in Business on Bloomberg Radio.
- 24:57Speaker 1: My uh, somewhat special guests. Is that how you want
- 25:00Speaker 1: to be? Is that how you described it? Said?
- 25:02Speaker 2: Marginally special?
- 25:03Speaker 1: My marginally special guest, Jack Rains is here. He is
- 25:08Speaker 1: an associate at the venture capital firm Slow Ventures and
- 25:12Speaker 1: the author of the book Young Money, which we'll get
- 25:15Speaker 1: to in a few minutes. So I'm kind of fascinated
- 25:18Speaker 1: how you pivoted into VC work. You joined Slow Ventures
- 25:23Speaker 1: in San Francisco from New York. Did you relocate to
- 25:27Speaker 1: San Francisco and then come back to New York? So
- 25:30Speaker 1: I kind of get this venture by coastal.
- 25:33Speaker 2: I try to. I try to. I try to make
- 25:36Speaker 2: it look by coastal occasionally on Twitter. No, I mean
- 25:38Speaker 2: The funny thing was they were hiring in New York
- 25:40Speaker 2: and San Francisco, and I applied for the New York job,
- 25:43Speaker 2: and met was the partner in New York first, and
- 25:46Speaker 2: then the one of the gps in San Francisco, Sam Lesson.
- 25:50Speaker 2: I get introduced to him by the guy in New
- 25:52Speaker 2: York and we're on a zoom call. He'd like, just
- 25:54Speaker 2: come from the gym, super sweaty and like shoveled looking,
- 25:57Speaker 2: and five minutes you all to say that.
- 26:00Speaker 1: I'm okay with that.
- 26:00Speaker 2: I think he would agree with it. Five minutes, five
- 26:03Speaker 2: minutes out of the call, he's like, what do you
- 26:04Speaker 2: think of San Francisco? And I said fentannel and homeless people,
- 26:07Speaker 2: and he was like, it's a crazy ass for somebody
- 26:10Speaker 2: applying to a job in San Francisco. And I was
- 26:12Speaker 2: just like, I didn't like I applied for the job
- 26:16Speaker 2: in New York and he was just kind of like, well,
- 26:19Speaker 2: I thought I was interviewing you for an SF seat,
- 26:21Speaker 2: and I was just like he told me to like
- 26:23Speaker 2: take a beat and like think about it. And I
- 26:25Speaker 2: can't rememer if I told him on the collar. Just
- 26:27Speaker 2: texted him right after, but I was like honestly, dude,
- 26:29Speaker 2: I mean, I want the job, so I didn't know
- 26:31Speaker 2: this is what I was applying for. But if you
- 26:33Speaker 2: hire me, I'll move to San Francisco. And he was like,
- 26:35Speaker 2: have you ever visited? And I said no, so.
- 26:38Speaker 1: But I've been to twenty five other countries in fifty
- 26:41Speaker 1: other cities. I'm sure I can figure it out.
- 26:43Speaker 2: Yeah. The only difference to San Francisco has so many
- 26:46Speaker 2: more AI startup advertisements on the billboards and the way mos,
- 26:49Speaker 2: which are awesome. But yeah, like I I mean I.
- 26:52Speaker 1: And they are everywhere. We were just San Francisco a
- 26:55Speaker 1: few months ago.
- 26:56Speaker 2: They're so sick.
- 26:57Speaker 1: They they're like yellow cabs in New York.
- 26:59Speaker 2: Yeah, yeah, they're They're incredible. I mean the worst thing
- 27:01Speaker 2: about New York is that we keep trying to like
- 27:03Speaker 2: block way Moos. Let it happen. I'm I'm so pro Weemo.
- 27:06Speaker 2: I'm like Waymo's biggest fanboy. But yeah, like, going back
- 27:10Speaker 2: to Fall twenty twenty four, I was in this real
- 27:13Speaker 2: like kind of career panic. I want to get out
- 27:15Speaker 2: of media, and like I was like I should have
- 27:17Speaker 2: gone down the investing route, and then you know it's
- 27:20Speaker 2: like a step back and I had like signed that
- 27:22Speaker 2: book deal. I was like, Okay, I'm gonna have to
- 27:24Speaker 2: write a book. I'm gonna have to be able to
- 27:25Speaker 2: market it. So that means I need to look at
- 27:27Speaker 2: jobs where I could still have like bandwidth and flexibility
- 27:30Speaker 2: to do so, which like eliminates a lot of investing
- 27:33Speaker 2: ease stuff where there's compliance issues.
- 27:35Speaker 1: No investment banking, no no trading on a desk, and
- 27:39Speaker 1: no portfolio management or even CFA analysts where whatever you
- 27:45Speaker 1: do is disclosable and requires approval and it's complex.
- 27:50Speaker 2: But venture capital is like the biggest, like build your
- 27:54Speaker 2: personal brand, like content helps you source deals. So I
- 27:57Speaker 2: kind of honed in on and I didn't have like
- 27:59Speaker 2: an investment banking back ground. VC is more open to
- 28:01Speaker 2: non traditional investing backgrounds. It just kind of made sense.
- 28:05Speaker 2: And I had a decent network in that space from
- 28:06Speaker 2: like Twitter and riding and all this stuff. So I
- 28:09Speaker 2: just kind of started pounding the pavement, like reaching out
- 28:11Speaker 2: to vcs. I knew of my network that may or
- 28:12Speaker 2: may not be hiring, and Slow happened to be hiring,
- 28:16Speaker 2: and I messaged hilariously. I messaged Yoni, the partner of
- 28:19Speaker 2: New York on Blue Sky, that was back when everybody
- 28:21Speaker 2: I thought Twitter was going to die and blue Sky
- 28:22Speaker 2: was Blue.
- 28:24Speaker 1: Sky didn't take off. But it does feel like Twitter
- 28:26Speaker 1: is kind of ground to a shell.
- 28:29Speaker 2: Of what it. I think it's starting to come back
- 28:31Speaker 2: as of like a month ago. Oh really, it feels
- 28:33Speaker 2: like they changed the algorithm where you can like see
- 28:35Speaker 2: your mutuals again, so people literally last week Nikita Beer tweeted,
- 28:40Speaker 2: they tweet the algo so like you're seeing your mutual
- 28:43Speaker 2: followers and I was like, dude, that's what it should
- 28:44Speaker 2: have been the whole time. But anyway, I basically got
- 28:48Speaker 2: hired from a Twitter DM and then a last second
- 28:50Speaker 2: flight to San Francisco six weeks.
- 28:53Speaker 1: From application to starting in SF.
- 28:56Speaker 2: Basically like I didn't know where to live. Facebook Marketplace,
- 29:01Speaker 2: found some dude with an open room and just hopped
- 29:02Speaker 2: on a FaceTime with him, and I was just like, yeah, like,
- 29:05Speaker 2: I guess I'll just take the other half of your apartment.
- 29:08Speaker 2: And then I moved there. That was I just put
- 29:10Speaker 2: my stuff in a in a suitcase and just flew out.
- 29:12Speaker 1: So are you New York based?
- 29:13Speaker 2: I live in New York now. I moved back here
- 29:15Speaker 2: a few months ago, all.
- 29:16Speaker 1: Right, And and how do you how do you work
- 29:18Speaker 1: that out if your core office is San Francisco.
- 29:22Speaker 2: So we have an office in New York too, Flat Iron,
- 29:25Speaker 2: so twentieth and fifth. It was one of those things
- 29:28Speaker 2: where we were pretty a sync in San Francisco, like
- 29:30Speaker 2: we have an office in downtown SF. I was going
- 29:34Speaker 2: in probably four days a week, so like some people
- 29:36Speaker 2: were going in a lot. My boss lived in the
- 29:38Speaker 2: suburbs a little bit. He would come up sometimes, but
- 29:40Speaker 2: I would like take the cowtrain down to like the
- 29:43Speaker 2: Hillsbo area and like go to his place. So I
- 29:45Speaker 2: work from his poolhouse with him. It was a funny setup,
- 29:49Speaker 2: but it was like we were a sync enough. And
- 29:51Speaker 2: I also knew that like long term, I was gonna
- 29:53Speaker 2: want to live in New York. I just pitched them
- 29:55Speaker 2: on moving back and then flying out to San Francisco
- 29:58Speaker 2: like every three weeks or so, and that it's the
- 30:00Speaker 2: setup I have now.
- 30:01Speaker 1: That New York has a pretty robust technology sets there.
- 30:06Speaker 1: I mean, we all think of San Francisco for AI
- 30:10Speaker 1: computer mobile tech and Boston for healthcare teche. Where does
- 30:15Speaker 1: New York land in that in that list?
- 30:17Speaker 2: It's it's increasing I would I would put in New
- 30:19Speaker 2: York is the.
- 30:20Speaker 1: Like pretty fast rising right on for.
- 30:22Speaker 2: Like consumer tech. I would argue it's like number one
- 30:25Speaker 2: or close to it.
- 30:26Speaker 1: And then you've got a big Google office here, You've
- 30:28Speaker 1: got a big Microsoft office here. You've got a giant
- 30:30Speaker 1: Amazon office here.
- 30:31Speaker 2: Well, and like Anthropics opening like a sixteen thousand square
- 30:34Speaker 2: foot like they're opening a massive office in Hudson Square.
- 30:38Speaker 1: Like you there's some space there.
- 30:39Speaker 2: A lot of like a lot of a lot of
- 30:42Speaker 2: what keeps happening is like all these AI companies start
- 30:44Speaker 2: there and then as they move into like bigger and bigger,
- 30:46Speaker 2: like enterprise commercial business, they expand to the East coast,
- 30:50Speaker 2: and like there's a lot of like sales teams on
- 30:51Speaker 2: the East coast and engineering town on the west coast.
- 30:54Speaker 2: New York's also like a more social, outgoing city where
- 30:57Speaker 2: a lot of the like like sales and go to
- 30:59Speaker 2: market people would prefer to live here. San Francisco is
- 31:02Speaker 2: more insular, and it's like, uh, there's just engineering talent
- 31:05Speaker 2: from like Stanford, Berkeley, whatever. It aggregates around the Bay.
- 31:09Speaker 2: So it's it's honestly a big part of like engineers
- 31:12Speaker 2: end up on the West coast, and then a lot
- 31:13Speaker 2: of the sales people end up on the East coast.
- 31:15Speaker 2: A lot of the customers are also on the East coast.
- 31:17Speaker 1: So really interesting. All right, So I got to start
- 31:21Speaker 1: with a few quotes of yours and we'll plow through
- 31:25Speaker 1: a lot of that. One of the things though, that
- 31:29Speaker 1: that you said a quote of yours, junior investing jobs
- 31:33Speaker 1: at VC megafunds are really just cold calling. Yeah, I
- 31:37Speaker 1: don't think of VC in those terms. Explain are you
- 31:41Speaker 1: really just smiling and dialing.
- 31:43Speaker 2: Like a little bit. It's funny, Like I don't know
- 31:45Speaker 2: if you read Bill Gurley's new book, Run It Out
- 31:47Speaker 2: of Dream, so he said something similar with a venture
- 31:49Speaker 2: capital is ninety percent sales, and it really is.
- 31:52Speaker 1: Like, but that's true about everything in fine Yeah, it's
- 31:54Speaker 1: really and I don't know about outside, but everything in
- 31:58Speaker 1: this space is you're ultimately asking someone to trust you
- 32:02Speaker 1: and give you their business.
- 32:03Speaker 2: Yep, yep, yep. VC, especially at the big like it's
- 32:07Speaker 2: like Slow is a fairly small fund, right, Like we
- 32:10Speaker 2: have like total teams like fifteen or sixteen people, investment
- 32:13Speaker 2: teams like nine or ten people. But like some of
- 32:16Speaker 2: the bigger funds, like I have some bodies that have
- 32:18Speaker 2: worked at the like call it some combination of like
- 32:21Speaker 2: the general catalyst type A sixteen Z type whatever. It's
- 32:25Speaker 2: just a machine or like inside is like this too,
- 32:28Speaker 2: or like you are managing just like tens of billions
- 32:31Speaker 2: of dollars or whatever, and there's so much coverage that
- 32:34Speaker 2: it's I was a little tongue in cheek saying that
- 32:37Speaker 2: it's like cold calling, but it is very much like
- 32:40Speaker 2: you need to be talking to like X number of people,
- 32:42Speaker 2: and there's like metric hurdles on like touch points and stuff.
- 32:45Speaker 2: It's like it's not that there's no discernment or anything
- 32:49Speaker 2: like that, but it's a volume game and.
- 32:51Speaker 1: They try and quantify it and turn it into.
- 32:55Speaker 2: Yeah, it's like you the name of the game is
- 32:58Speaker 2: you don't want to miss anything that could be something. Therefore,
- 33:01Speaker 2: like people should be pounding the pavement making touch points
- 33:04Speaker 2: with anybody who could be starting an early stage tech company.
- 33:06Speaker 1: Now, Slow Ventures kind of famously avoids the trendy hot stuff.
- 33:12Speaker 1: No robots, no AI foundation models, What are you looking
- 33:17Speaker 1: at at work? That's kind of interesting. What do you
- 33:20Speaker 1: guys get to see that most people are overlooking?
- 33:23Speaker 2: So it's funny. We actually we actually just announced one
- 33:26Speaker 2: that's like robot e doing like like warehouses and fulfillment
- 33:30Speaker 2: for e commerce companies called Sutronic, So we do occasionally
- 33:33Speaker 2: touch they don't make You'm right right, We're not doing
- 33:38Speaker 2: any of the stuff that it's cloud on Twitter because
- 33:40Speaker 2: we can't fold, close or do dishes, right. I mean
- 33:44Speaker 2: it's we're like broadly generalists. We've done everything from like
- 33:48Speaker 2: we've done just to name some companies over the last
- 33:50Speaker 2: ten or twelve years, like Robinhood, Slack, all Birds before
- 33:55Speaker 2: they pivoted to being an AI GPU company back when
- 33:58Speaker 2: they sold footwear. I mean, we have like a hilarious
- 34:02Speaker 2: one meme, Lord's Technology where it's basically a software platform.
- 34:05Speaker 2: It's like a basically marketing tool platform, but for creating memes.
- 34:10Speaker 2: I mean, we'll do a little bit of everything we've done.
- 34:12Speaker 2: Crypto stuff we've done. We have done some like vertical
- 34:14Speaker 2: AI stuff. We just like making our calling card. We're
- 34:17Speaker 2: not chasing the AI hype. The way that we broadly
- 34:20Speaker 2: think about it is there's a lot of VC deals
- 34:24Speaker 2: that are trades that are now marked up a lot,
- 34:27Speaker 2: but like do they have terminal value in what they
- 34:29Speaker 2: get supported in public markets? You don't know? And a
- 34:32Speaker 2: lot of early stage investors that have played those and
- 34:34Speaker 2: then sold when bigger funds come in at the multi
- 34:37Speaker 2: billion dollar evaluations. It made a lot of money. So
- 34:39Speaker 2: like you could argue we should have played that trading game.
- 34:42Speaker 2: The bet that we're making is like, go for the
- 34:45Speaker 2: stuff that's going to compound long term value, that could
- 34:47Speaker 2: be like a standalone valuable entity.
- 34:50Speaker 1: How does the sort of dearth of IPOs, although we're
- 34:54Speaker 1: in the middle of a period where there are suddenly
- 34:57Speaker 1: a spate of them coming out and more more companies
- 35:00Speaker 1: choosing to stay private for longer, how does that figure
- 35:05Speaker 1: into the VC calculus of Hey, we eventually want an
- 35:08Speaker 1: exit and we can't rely on someone else, either from
- 35:11Speaker 1: a big affirm taking this over or some M and
- 35:15Speaker 1: A to give us an exit.
- 35:16Speaker 2: It's interesting. I almost think you have to put VC
- 35:19Speaker 2: in two buckets at this point, where you have like
- 35:21Speaker 2: we play at the really early stage, which also gives
- 35:23Speaker 2: you like a lot more opportunities for exits, whether you
- 35:26Speaker 2: sell steakes to like a later stage bigger growth like
- 35:29Speaker 2: a bigger growth investor once they're in the unicorn status,
- 35:33Speaker 2: or you get the acquisition or IPO if you're getting
- 35:35Speaker 2: at a company that's worth twenty or thirty million dollars.
- 35:38Speaker 2: There's just like a lot of ways you can get
- 35:39Speaker 2: paid on that. Versus you have companies like like Thrive
- 35:43Speaker 2: is probably the most famous one where they manage like
- 35:44Speaker 2: fifty billion dollars now they own a massive slug of
- 35:47Speaker 2: open ai, Like they take really big bets in companies
- 35:51Speaker 2: that are like it's worth ten billion or one hundred billion,
- 35:54Speaker 2: we think it can be worth a hundred billion or
- 35:56Speaker 2: a trillion. So for us, we have a lot more
- 35:59Speaker 2: flexibility on exits, which is like good because we can
- 36:02Speaker 2: be more nimble.
- 36:02Speaker 1: You're primarily seed in A rounds, but you're not doing
- 36:06Speaker 1: B rounds, or.
- 36:07Speaker 2: We occasionally will with follow on capital, but it's like
- 36:10Speaker 2: ninety five percent seed in A So that's like that's
- 36:12Speaker 2: our sweet spot. And then so I think for funds
- 36:15Speaker 2: like that, I think people like a lot of early
- 36:19Speaker 2: stage funds should get more creative. Where can you exit
- 36:22Speaker 2: into a big growth fund coming in at like a
- 36:24Speaker 2: five billion dollar valuation from portfolio construction? Maybe you should
- 36:28Speaker 2: With the megafunds, it's like, okay, if you're going to
- 36:31Speaker 2: do that, you can't really index all of the like
- 36:34Speaker 2: five or ten billion dollar unicorns because a lot of
- 36:36Speaker 2: those those paper marks would never get support in the
- 36:38Speaker 2: public markets. But like Thrive going really deep on open
- 36:44Speaker 2: Ai or Spark Capital going really deep on Anthropic, those
- 36:48Speaker 2: are going to go out at potentially trillion dollar valuations.
- 36:51Speaker 2: Like the math works. If you invest forty billion dollars
- 36:55Speaker 2: across a few big funds and something at like a
- 36:57Speaker 2: two hundred billion dollars valuation and you get four x
- 37:00Speaker 2: or five x, you're returning like tens of billions of dollars. Right,
- 37:04Speaker 2: So it's like in the early stage should probably be
- 37:07Speaker 2: looking to sell, and some some of those later stage
- 37:10Speaker 2: companies coming in at the later stage, it's like stock picking.
- 37:13Speaker 2: You're basically running. You have to run a concentrated book
- 37:15Speaker 2: of like there might be three or four private companies
- 37:17Speaker 2: at any time, like a SpaceX, Open Ai and Thropic
- 37:20Speaker 2: that could go out at a multi hundred billion dollar valuation.
- 37:24Speaker 2: You have to be concentrated in those otherwise the math
- 37:27Speaker 2: is going to work. If you get those right, you
- 37:29Speaker 2: can like two x three x a fund. If you don't,
- 37:31Speaker 2: you want.
- 37:32Speaker 1: Really kind of interesting you come out of the creator economy.
- 37:37Speaker 1: Slow Ventures has been a player in that space. How
- 37:42Speaker 1: does how does your experience help you as a VC
- 37:47Speaker 1: and what does slow venture see in that space that
- 37:50Speaker 1: you know the traditional venture capitalists overlook.
- 37:53Speaker 2: So to give like a little more color on that
- 37:55Speaker 2: we have we have a separate fund we raised a
- 37:57Speaker 2: year ago called our Creator Fund, where sixty four million
- 38:00Speaker 2: dollars we invest directly in creators, meaning like YouTubers, podcasters,
- 38:05Speaker 2: could be newsletter writers. Our bet on that is that
- 38:09Speaker 2: like distribution compared to like technical abilities is getting increasingly valuable.
- 38:14Speaker 2: Where two things One, it's easier to build stuff like
- 38:17Speaker 2: software because of AI coding assistance. Too, the Internet is
- 38:21Speaker 2: so loud now that having like a cylinder of trust
- 38:24Speaker 2: from your audience gives you a massive selling advantage because
- 38:27Speaker 2: it's so much harder to get attention with like paid
- 38:29Speaker 2: ads and growth hacks and all this. That we have
- 38:33Speaker 2: this and like sam My Boss was kind of came
- 38:35Speaker 2: up with this idea a few years ago that like
- 38:37Speaker 2: he calls it almost investing in cults. But people who
- 38:40Speaker 2: have a true like cult of personality and are a
- 38:42Speaker 2: subject matter expert in a particular theme or vertical have
- 38:46Speaker 2: a massive advantage on like marketing and selling. So we
- 38:50Speaker 2: raised a fund where we literally invest in creators like
- 38:54Speaker 2: holding companies where any businesses they build like off their platform,
- 38:58Speaker 2: that leverage their brand and platform and all this stuff.
- 39:00Speaker 1: These are three sixty deals covers everything that person does.
- 39:03Speaker 2: Yeah.
- 39:04Speaker 1: Yeah, we basically be a podcast, could be substack, could
- 39:06Speaker 1: be all of those.
- 39:07Speaker 2: Yeah, and like we aren't really that interested in like
- 39:09Speaker 2: how money they make from like ad revenue or like
- 39:12Speaker 2: platform revenue or whatever. It's more so. For example, the
- 39:15Speaker 2: first deal we did was with this woodworking creator named
- 39:18Speaker 2: Jonathan Katz Moses, and he has a like he has
- 39:21Speaker 2: a massive YouTube channel.
- 39:22Speaker 1: He's basically I know that just show it is shockingly
- 39:26Speaker 1: intriguing watching this guy build stuff from scratch. Yeah, he's
- 39:30Speaker 1: like relaxing too.
- 39:32Speaker 2: Yeah, he's a super compelling guy, incredibly talented, and he's
- 39:36Speaker 2: equally good as both a content creator and as an entrepreneur.
- 39:39Speaker 2: Like he has a business it's like making like millions
- 39:41Speaker 2: of dollars in revenue, and.
- 39:43Speaker 1: He builds various things and sells them, so he also
- 39:47Speaker 1: generates revenue from the YouTube.
- 39:49Speaker 2: Right, And it's like a specifically has like a tool
- 39:51Speaker 2: line called km Tools, and like we invested money into
- 39:55Speaker 2: like his holding company, and that can go toward like
- 39:57Speaker 2: hiring people to help with like the content development, editing,
- 40:01Speaker 2: content creation, so we can like increase velocity of putting
- 40:04Speaker 2: out YouTube videos. Also like more people to help rolling
- 40:07Speaker 2: out new products and a wider product suite of tools.
- 40:09Speaker 2: So the bet is that like you put money in
- 40:12Speaker 2: that and maybe like the tool business really blows up
- 40:14Speaker 2: and then a like Black and Decker type of company
- 40:17Speaker 2: acquires it, or maybe he launches like another business vertical
- 40:20Speaker 2: office platform that we have exposure to. So it's but
- 40:23Speaker 2: his whole thing is like woodworking, woodworkers. He'll go to
- 40:26Speaker 2: like a woodworking festival in Texas, people will come out,
- 40:29Speaker 2: like to come like get him to like sign their autographs.
- 40:32Speaker 2: Like he he just has a lot of clout in
- 40:34Speaker 2: that space. So finding people like that in different verticals
- 40:38Speaker 2: that we think have like really compelling opportunities to scale
- 40:41Speaker 2: big businesses through that vertical in that audience is like interesting.
- 40:46Speaker 2: And historically people have been very hesitant to back creators
- 40:50Speaker 2: or they back like one business like mister Beast has
- 40:52Speaker 2: a bunch of different businesses. If you back Beast Burgers
- 40:55Speaker 2: didn't really work that well. If you were backing mister
- 40:58Speaker 2: Beasts as a whole, Like the entire empire is worth
- 41:01Speaker 2: like a billion dollars or whatever. So you want to
- 41:03Speaker 2: be like a line where if they want to change
- 41:06Speaker 2: their focus, like are capital is still aligned with that?
- 41:09Speaker 2: Like you don't think this this experiment's working.
- 41:11Speaker 1: Moved to this one and I think it's called CDC.
- 41:14Speaker 1: If you haven't seen these computer controlled woodworking lathes and carves,
- 41:20Speaker 1: and they're just astonishing with people Like you think of
- 41:24Speaker 1: carpentry as kind of old school, it is not. It's
- 41:28Speaker 1: really fascinating. Coming up, we continue our conversation with Jack
- 41:32Speaker 1: Rains discussing his new book Young Money, a field guide
- 41:37Speaker 1: to wealth and purpose in your twenties. I'm Bury Ridults.
- 41:41Speaker 1: You're listening to Masters in Business on Bloomberg Radio. I'm
- 41:46Speaker 1: Barry Ridults. You're listening to Masters in Business on Bloomberg Radio.
- 41:51Speaker 1: My pretty special guest, my kind of.
- 41:54Speaker 2: Special, somewhat special.
- 41:56Speaker 1: Somewhat special guests. I'm want to write that down. My
- 41:59Speaker 1: somewhat special guest is Jack Reins. He is a associate
- 42:02Speaker 1: at a venture capital firm and a author. I've been
- 42:07Speaker 1: subscribed to his sub stack Young Money for I don't
- 42:10Speaker 1: know how many years.
- 42:11Speaker 2: Has that been, around four or five years?
- 42:13Speaker 1: Let me know when you get to thirty and you'll
- 42:15Speaker 1: be onto something. But his new book Young Money, A
- 42:20Speaker 1: Field Guide to Wealth and Purpose in your twenties, I
- 42:25Speaker 1: was really taken by it. Not only was it a
- 42:27Speaker 1: fun read, but I just I not only laughed throughout
- 42:33Speaker 1: because I just recognized, oh, I did that dumb thing,
- 42:37Speaker 1: but it also is so wise beyond its years. It's
- 42:41Speaker 1: hard to imagine that the guy who wrote this was
- 42:44Speaker 1: twenty six twenty seven when he wrote it twenty seven,
- 42:47Speaker 1: twenty seven, eight last year of your twenties. So I
- 42:53Speaker 1: really found it a fun, enjoyable read about a space
- 42:57Speaker 1: that I normally don't play in Young Money. And there's
- 43:01Speaker 1: so many things to talk about with this, starting with
- 43:07Speaker 1: quote I had considered the opportunity cost of how I
- 43:11Speaker 1: was spending my time, and I adjusted my life accordingly.
- 43:16Speaker 1: So you're giving the whole game away on page thirteen. Yep,
- 43:20Speaker 1: you basically say, hey, time is finite, and how and
- 43:25Speaker 1: when you spend it is really important. Tell us a
- 43:28Speaker 1: little bit about how you reach that insight back when
- 43:32Speaker 1: you were in your early in the mid twenties.
- 43:34Speaker 2: Yes, so, I mean we talked about the spactrading thing earlier,
- 43:38Speaker 2: but like when I was twenty three, mainly twenty three,
- 43:42Speaker 2: in a little bit twenty four, my life basically looked
- 43:44Speaker 2: like this. It was you roll out of bed, throw
- 43:46Speaker 2: on some sweatpats, grab Chick fil A for breakfast, and
- 43:50Speaker 2: then you're just like kind of responding to like slack messages.
- 43:53Speaker 2: You're on zoom calls, spreadsheets, powerpoints, and you're doing all
- 43:56Speaker 2: of your bedroom. And it had been like that for
- 43:58Speaker 2: well over a year. And then on the side, like
- 44:01Speaker 2: you were over here, like you know, training options before
- 44:03Speaker 2: we jump on this, I had like my work laptop here,
- 44:05Speaker 2: and then I'm my personal laptop here, and it's like,
- 44:08Speaker 2: huh interesting, like this spat just got an ounce. So
- 44:10Speaker 2: I was I was spending like I was like basically
- 44:13Speaker 2: fake working while just trading stocks all day. And then
- 44:15Speaker 2: like in the evenings, I you know, you have like
- 44:17Speaker 2: your entire net worth and some speculative spack and you're
- 44:20Speaker 2: you can't even sleep straights if futures take you think
- 44:23Speaker 2: you might lose one hundred thousand dollars. And so I
- 44:26Speaker 2: was almost in this like self a news holding cell
- 44:28Speaker 2: of like I couldn't go anywhere really because of COVID,
- 44:30Speaker 2: and I was stuck at home, and then I was
- 44:32Speaker 2: just watching screens all day, and thankfully I made some
- 44:35Speaker 2: money from it. But I just became really aware around
- 44:40Speaker 2: the time I was about to turn twenty four that
- 44:42Speaker 2: I had just spent the whole last year of my
- 44:44Speaker 2: life not really doing anything, especially like call it like
- 44:49Speaker 2: personal relationships whatever. I was probably a pretty terrible like boyfriend, friend,
- 44:54Speaker 2: checked out, son, grandson, like I just wasn't like I
- 44:58Speaker 2: was not in control of ho I was spending my
- 44:59Speaker 2: time at all. I was kind of like a prisoner
- 45:01Speaker 2: to like work and COVID and stock market.
- 45:06Speaker 1: Which is kind of crazy because during the pandemic, you're
- 45:09Speaker 1: no longer commuting, you're no longer on the same schedule.
- 45:13Speaker 1: If any of us had a little more prescience, we
- 45:17Speaker 1: really could have taken full control of our day. Nobody's
- 45:21Speaker 1: looking over your shoulder at what you're doing. You could
- 45:23Speaker 1: come and go as you want as long as you
- 45:25Speaker 1: got your work done whenever. However, everybody was.
- 45:28Speaker 2: Fine, which is so I mean to the stock trading
- 45:32Speaker 2: thing I did, like that would not have been happening
- 45:33Speaker 2: if I was in the office, probably at least not
- 45:36Speaker 2: as much.
- 45:36Speaker 1: But what was fascinating as I was reading this because
- 45:39Speaker 1: I started out trading is you. You nailed the phrase
- 45:45Speaker 1: you're a prisoner to the screen. You really can't leave
- 45:49Speaker 1: your desktop. If you're on a desk, at least someone
- 45:52Speaker 1: could watch a position for you. Hey, I gotta go
- 45:55Speaker 1: leave for ten minutes. Can you make sure this doesn't
- 45:57Speaker 1: blow up on me? If it hits this, get me out?
- 46:00Speaker 1: You could do that. But if you're doing this from
- 46:02Speaker 1: your bedroom and you have a lot of positions on you,
- 46:05Speaker 1: you're you have no other bandwidth for anything else.
- 46:08Speaker 2: It's just push notifications on for everything. You go to
- 46:11Speaker 2: the gym, you're checking your phone every two minutes. It
- 46:13Speaker 2: was just like a little bit nauseating, right, and.
- 46:15Speaker 1: Uh and exhausting.
- 46:16Speaker 2: Yeah, And like I I honestly just felt pretty like
- 46:19Speaker 2: mentally exhausted from the like always being on and I
- 46:23Speaker 2: just kind of had enough. And I also found my
- 46:26Speaker 2: job pretty unfulfilling, and I knew I was going to
- 46:28Speaker 2: leave it in a year, And it was just like
- 46:30Speaker 2: all of these things came to a head and I
- 46:32Speaker 2: was like, Okay, let's be really intentional here about like
- 46:35Speaker 2: how do I want to spend Like if I know
- 46:38Speaker 2: I'm going to grad school in a year, like, how
- 46:39Speaker 2: do I actually want to spend the next year? Is
- 46:41Speaker 2: it keep going in the motions of the job that
- 46:43Speaker 2: I know I'm going to leave to go do something else?
- 46:45Speaker 2: Is that like like try to like trade back the
- 46:48Speaker 2: money I just lost lost on that trade gone wrong?
- 46:51Speaker 2: The thing I kind of wanted to do is like, honestly,
- 46:53Speaker 2: just go have an adventure having just been cooped up
- 46:55Speaker 2: for a year and a half. And yeah, so that
- 46:58Speaker 2: like it was just like all of that came to
- 47:00Speaker 2: ahead and I was like I should just I mean,
- 47:03Speaker 2: it's like the opening line of the book, just blow
- 47:05Speaker 2: up my life and go do something crazy. And that's
- 47:07Speaker 2: kind of what I did, and I went to Barcelona.
- 47:09Speaker 1: You hit the eject button. The concept of time comes
- 47:15Speaker 1: up over and over throughout the book, both generally and specifically.
- 47:20Speaker 1: One of the things you write about is defining decades differently,
- 47:24Speaker 1: and about the opportunity cost of your twenties. A lot
- 47:28Speaker 1: of people who just buckle down and grind it out
- 47:32Speaker 1: through their twenties. You say that for many people that's
- 47:36Speaker 1: a trap. Smart twenty something's fall into to discuss that.
- 47:40Speaker 2: So I and I think this is especially true in
- 47:42Speaker 2: the like call it hyper competitive, like New York, San Francisco,
- 47:47Speaker 2: maybe like Chicago, DC areas where you're surrounded by very
- 47:51Speaker 2: smart people who went to really good schools and they
- 47:54Speaker 2: go into like at least for like an early twenty
- 47:56Speaker 2: something high paying job, but you're also objectively pretty, but
- 48:00Speaker 2: you don't know anything you like, don't like No twenty
- 48:02Speaker 2: two especially guys like yeah.
- 48:05Speaker 1: And tell me when I get to grow out of that.
- 48:09Speaker 2: I don't know. I mean you tell me. You're sitting
- 48:12Speaker 2: there and it's like, okay, like what do I optimize for?
- 48:15Speaker 2: And the obvious thing is money, and the like derivative
- 48:19Speaker 2: of that is status, right where high paying jobs are
- 48:23Speaker 2: typically higher status jobs. And I think it's when you
- 48:28Speaker 2: don't have anything else. It's like like a north Star.
- 48:30Speaker 2: You kind of go for like the like ambitious thing
- 48:33Speaker 2: that will pay you well, that sounds impressive over and
- 48:36Speaker 2: over again, and like, to be totally clear, there's nothing
- 48:39Speaker 2: wrong with that, and that's also much better than like
- 48:42Speaker 2: being a bomb and not doing anything. But you almost
- 48:46Speaker 2: if you fall into that trap of like having some
- 48:49Speaker 2: expectation of what you should do without it actually being
- 48:51Speaker 2: like your own original thought like oh I want to
- 48:53Speaker 2: go do this, you almost become instead of being like
- 48:56Speaker 2: the protagonist of your own life, you're just kind of
- 48:58Speaker 2: like filling a preordain role, Like you're almost like an actor, right,
- 49:02Speaker 2: is how I think about.
- 49:02Speaker 1: It, and in someone else's play, right.
- 49:05Speaker 2: And I think the thing like I think the implicit
- 49:10Speaker 2: bat people are making when they do that is I
- 49:12Speaker 2: will like earn enough money and hit a level of
- 49:14Speaker 2: stability where I can head eject, which you can do,
- 49:18Speaker 2: but you can't buy back the opportunities that you would
- 49:23Speaker 2: have had in your twenties when you're in your like
- 49:24Speaker 2: mid thirties.
- 49:25Speaker 1: So another quote, there's no saving time, there's no investing time.
- 49:31Speaker 1: There is only spending time. And sentences like that is
- 49:35Speaker 1: why I say this book is wise beyond its years,
- 49:39Speaker 1: because I know people who figure that out in their fifties, sixties, seventies,
- 49:44Speaker 1: not in their twenties. So kudos to you forgetting there
- 49:49Speaker 1: to tell us what led you to that conclusion and
- 49:55Speaker 1: how much did the pandemic lockdown accidentally lead to these insights.
- 50:01Speaker 2: I think I became much more introspective much younger, because,
- 50:08Speaker 2: like you just, I mean, I had roommates them, like
- 50:10Speaker 2: I just wasn't spending like that much time in a
- 50:12Speaker 2: normal day to day and I'm a very like sociable
- 50:15Speaker 2: guy who like likes to hang out with people during
- 50:18Speaker 2: the day. That gets removed and you're just in your
- 50:20Speaker 2: head a lot, and you become really reflective of like
- 50:22Speaker 2: how you're spending your time, what you're motivated by. So
- 50:25Speaker 2: it was just like this again, I don't like this
- 50:28Speaker 2: book probably wouldn't have happened if COVID didn't happen, because
- 50:30Speaker 2: most of these like reflections were downstream of this hole
- 50:34Speaker 2: just being like kind of in like an isolated stage
- 50:38Speaker 2: of life at a point where like you should really
- 50:40Speaker 2: just be like in an office grinding. So I think
- 50:44Speaker 2: that was a big part of it. Hilariously, I like
- 50:46Speaker 2: I mentioned, like the second chapter of the book, I
- 50:48Speaker 2: used to be terrified of flying, and U like, like
- 50:51Speaker 2: I'd fly all the time down I don't care. But
- 50:53Speaker 2: for some reason, turbulence just like kicked my When I
- 50:56Speaker 2: was younger and I was on a flight to Colorado
- 50:59Speaker 2: about a year and a pandemic for ski trip, plame
- 51:02Speaker 2: was basically empty. It was awesome. We had a super
- 51:05Speaker 2: super turbulent takeoff and it was just bumpy from Atlanta
- 51:08Speaker 2: basically all the way to like Kansas City, and I
- 51:11Speaker 2: was just sitting there thinking the whole time, we're tolling
- 51:13Speaker 2: to do die. Those thing's going now we're gonna die.
- 51:15Speaker 2: Like it's I'm twenty three, it's over, I'm dead. And
- 51:18Speaker 2: we obviously landed. I didn't die, but like some again
- 51:23Speaker 2: totally random, but just something about that put that thought
- 51:27Speaker 2: back my mind, like like at some point you are
- 51:29Speaker 2: going to die, and it's not like up until that,
- 51:32Speaker 2: I just thought I was gonna live forever, Like that's
- 51:34Speaker 2: a not stupid, but.
- 51:37Speaker 1: You don't really think about that in your twenties. When
- 51:40Speaker 1: most people are in their twenties, they're immortal. You're not
- 51:43Speaker 1: thinking about, well, one day I'm gonna die.
- 51:46Speaker 2: Yeah, And that became like a forcing function for like, okay,
- 51:48Speaker 2: let's work backwards from I finally got over the fear
- 51:52Speaker 2: of flying. But it's like, all right, like we are,
- 51:53Speaker 2: you know, we're on the clock, and what do I
- 51:56Speaker 2: want to do with it? And so it was like
- 51:58Speaker 2: a complete fluke from a turbulent flight kind of forced
- 52:01Speaker 2: a lot of introspection that have been bubbling under the
- 52:03Speaker 2: surface for probably the prior year. I was like, all right,
- 52:06Speaker 2: like I should be doing what I want with my
- 52:08Speaker 2: time rather than just letting inertia kind of do its thing.
- 52:11Speaker 2: And it was that like call it like awareness of
- 52:15Speaker 2: mortality that became like a forcing function for basically what
- 52:18Speaker 2: I've done in the last four and a half years
- 52:21Speaker 2: since then, like, be in control of your time. Don't
- 52:25Speaker 2: don't be a don't be like a passive participant in
- 52:27Speaker 2: your own life.
- 52:29Speaker 1: The difference between money and time is that money is
- 52:32Speaker 1: both infinite and fungible. Time is neither. This this is
- 52:40Speaker 1: a philosophical concept.
- 52:41Speaker 2: I consider myself a bit of a philosopher.
- 52:43Speaker 1: Okay, I'm with you, I'm there with you. What's your
- 52:48Speaker 1: conclusion when you realize that money is both infinite and fungible.
- 52:53Speaker 2: I think you like need to be really aware of
- 52:59Speaker 2: how much money it takes to get what you want
- 53:01Speaker 2: out of life at various life stages. To your point, earlier,
- 53:04Speaker 2: you can kind of scrape by in your twenties maybe
- 53:05Speaker 2: early thirties and like still enjoy yourself. And the older
- 53:09Speaker 2: you get, the more expensive it gets. Ideally you're making
- 53:12Speaker 2: more and more money over the course of your life
- 53:13Speaker 2: as well. So like my conclusion on that is it's
- 53:16Speaker 2: like counter to a financial device. But like young people
- 53:19Speaker 2: shouldn't penny pinch so much if they have like fun,
- 53:21Speaker 2: interesting stuff they want to spend the money on. The
- 53:24Speaker 2: caveat to that is like you should put yourself in
- 53:27Speaker 2: a position where there are like high income outcomes from
- 53:30Speaker 2: that over time. But like it's okay to be twenty
- 53:33Speaker 2: five and not be rich if it means like spending
- 53:35Speaker 2: money on fun stuff with your friends. Right.
- 53:37Speaker 1: So, you're not a fan of the fire movement, the
- 53:40Speaker 1: early retirement movement.
- 53:43Speaker 2: Not when it's taken to the extreme. I think that
- 53:45Speaker 2: the core idea of like having enough money saved up
- 53:49Speaker 2: where like you control your own destiny is healthy and
- 53:52Speaker 2: good and admirable. I think when you make the accumulation
- 53:55Speaker 2: of capital to like escape the labor force as like
- 53:58Speaker 2: an end goal, you just set yourself up to be
- 54:00Speaker 2: bored and almost beyond that, when you're like overoptimize for
- 54:05Speaker 2: fire and your whole thing is like I want to
- 54:07Speaker 2: opt out of work, you're probably gonna hit that in
- 54:09Speaker 2: your like early forties, when all of your peers are
- 54:12Speaker 2: peak work. You're not gonna be able to relate to
- 54:14Speaker 2: anybody after everal years. Against there's a lot of I
- 54:17Speaker 2: think when you take the fire movement too far. There's
- 54:20Speaker 2: like social costs to that that are harder to see
- 54:22Speaker 2: when you're looking at a spreadsheet. But it's just like,
- 54:25Speaker 2: and you have to forgo so many things you would
- 54:27Speaker 2: probably prefer to spend money on in your twenties and
- 54:30Speaker 2: thirties to hit that. It's just not I don't think
- 54:32Speaker 2: you should like go into crazy debt and you should
- 54:34Speaker 2: max out your four one K if you can and
- 54:36Speaker 2: all this stuff, But like you just you shouldn't pass
- 54:39Speaker 2: up on life to accumulate cash to be able to
- 54:42Speaker 2: opt out of another part of life being work. Is
- 54:44Speaker 2: kind of my take on it.
- 54:46Speaker 1: No, that makes a lot of sense. I love this quote.
- 54:49Speaker 1: Many of life's adventures are adventures only because you're twenty
- 54:53Speaker 1: two and broken stupid and you're surrounded by other broke,
- 54:58Speaker 1: stupid twenty two year olds. This is a feature, not
- 55:01Speaker 1: a flaw of being young. Lean into it, yep, tell
- 55:06Speaker 1: us about how you saw that. What is it about
- 55:10Speaker 1: being twenty two and broken stupid that has to be embraced?
- 55:14Speaker 2: So like I, I mean, I spent that whole year
- 55:17Speaker 2: of being I guess I was technically twenty four, but
- 55:20Speaker 2: I was with a lot of twenty two year olds
- 55:21Speaker 2: who are like this whole like hostel hopping things hilarious, right,
- 55:24Speaker 2: because it's basically a bunch of kids, like studying abroad.
- 55:27Speaker 2: It's a bunch of people fresh out of college. It's
- 55:30Speaker 2: a bunch of Europeans taking a gap year, a bunch
- 55:32Speaker 2: of Americans fresh out of college, and then a bunch
- 55:34Speaker 2: of like call twenty three to twenty six year olds
- 55:36Speaker 2: who worked for a couple of years and took a break,
- 55:39Speaker 2: and you're all just like in bunk beds. Everybody has
- 55:42Speaker 2: a shared goal of like, I'm just trying to have
- 55:44Speaker 2: cheap fun for a little while, and it makes every
- 55:47Speaker 2: situation really really funny. Like some guys want to go
- 55:51Speaker 2: from Sevilla, Spain to Paris and they're trying to game
- 55:53Speaker 2: out like it's two hundred dollars to fly, but if
- 55:56Speaker 2: we take a train ticket and then sleep in a
- 55:57Speaker 2: train station for six hours, we can there for twelve dollars.
- 56:01Speaker 1: And or and avoid a hotel room, right, and.
- 56:04Speaker 2: Avoid a hotel room and extend our European trip like
- 56:06Speaker 2: eight more days. Right, So or you have life?
- 56:10Speaker 1: Did that right? You went from Barcelona to where in Europe?
- 56:13Speaker 2: I mean I I covered I was there from August
- 56:18Speaker 2: cit December, and then I went to Latin America a
- 56:21Speaker 2: month later for a few months, and back to Europe
- 56:22Speaker 2: and that August Citycember thing. I think I went to
- 56:26Speaker 2: like nineteen different countries in four months, and it was
- 56:29Speaker 2: just there was no itinerary. I would just go somewhere
- 56:32Speaker 2: and then I would meet some people and they would say, hey, dude,
- 56:34Speaker 2: we're going to Prog next. Do you want to come?
- 56:36Speaker 2: And I was like sure, sure, And I meet this
- 56:38Speaker 2: guy in Prague He's like, yo, I heard Budapest is great.
- 56:40Speaker 2: I'm like all right, And then I was like, we're
- 56:42Speaker 2: going to crack al Poland next I met a kid
- 56:44Speaker 2: at a hostel in Crackowl who pitched me on his
- 56:46Speaker 2: startup in San Francisco a year ago, like talking about
- 56:48Speaker 2: weird yeah, small world stuff. But it was just like
- 56:52Speaker 2: I went like pure optionality for a year and it
- 56:56Speaker 2: was just like anybody I meet interesting was doing something cool.
- 56:58Speaker 2: I'm going to go with them, like oh I heard
- 57:00Speaker 2: Tromso Norway. You can see the northern lights. Let's go
- 57:03Speaker 2: dog sledding up there, and like you do that. So
- 57:07Speaker 2: the ability to just like cast a really wide net
- 57:10Speaker 2: because when like cheap thrills are fighting, like having to
- 57:13Speaker 2: sleep on a train or I have a buck bed
- 57:15Speaker 2: with a stranger. It's just like it's fine, like when
- 57:18Speaker 2: you're when you're a kid, you just don't care. I like,
- 57:21Speaker 2: I'm still in my twenties now, but that would just
- 57:23Speaker 2: sound awful, Like I don't want to be in a
- 57:25Speaker 2: room with like twelve strangers and worry about my stuff
- 57:27Speaker 2: getting stolen.
- 57:27Speaker 1: That sounds terrible, but like twenty four, you got nothing
- 57:30Speaker 1: to get stolen anyway.
- 57:31Speaker 2: Yeah, it's like where they gonna take my backpack? We
- 57:33Speaker 2: had a couple of like Czara T shirts and flip flops,
- 57:35Speaker 2: sick Like I'll go play poker and win twenty bucks
- 57:37Speaker 2: and go buy another one. It's fine. So and there's
- 57:40Speaker 2: versions of that to play out and everything, right, Like
- 57:42Speaker 2: I'm I don't think everybody has to go backpack Europe.
- 57:45Speaker 2: But like you got to San Francisco and there's like
- 57:47Speaker 2: twenty four year old startup founders that are sleeping in
- 57:49Speaker 2: the office with a bunch of their buddies and they
- 57:51Speaker 2: are having a blast. Like they're in objectively like horrid
- 57:55Speaker 2: living conditions. They don't even notice because they're like twenty
- 57:57Speaker 2: three or twenty two or whatever, like you can you
- 58:00Speaker 2: can just really lean into like adverse living conditions and
- 58:03Speaker 2: find them enjoyable rather than like they don't like take
- 58:06Speaker 2: away from your life. They create really funny stories.
- 58:10Speaker 1: I'm always fascinated by the pursue your passion recommendation that
- 58:15Speaker 1: so many people make. You say, pursue your passion is
- 58:19Speaker 1: terrible career advice. Yeah, give us some color on that. So, like,
- 58:23Speaker 1: and you're giving this from someone who is pursuing their passion.
- 58:27Speaker 2: So my my like more specific take on that is
- 58:31Speaker 2: you shouldn't bank your income on a thing you're passionate about.
- 58:34Speaker 2: The example that I give is, like, I love writing.
- 58:36Speaker 2: It's a it's a thing that like I've enjoyed, I'll
- 58:38Speaker 2: do the rest of my life, whether it's books, blogs,
- 58:41Speaker 2: it's something I'll always incorporate. My initial job out of
- 58:44Speaker 2: business school was columnist, podcast or media guy like effectively
- 58:49Speaker 2: a media startup, and I actually found it stressful, where
- 58:52Speaker 2: like every single day I had to like put something
- 58:54Speaker 2: out and then I also was sitting there thinking this
- 58:57Speaker 2: is draining the fun of like writing. Like I wasn't
- 58:59Speaker 2: monetized as in my blog. It was just a thing
- 59:01Speaker 2: that I like doing, and all of a sudden, now
- 59:03Speaker 2: I don't have energy to work on that fun thing
- 59:05Speaker 2: because I spend all that energy on the thing I'm
- 59:07Speaker 2: paid to do. So the issue with like chasing your
- 59:11Speaker 2: passion is one, a lot of passions aren't that lucrative.
- 59:14Speaker 2: Two the second that your paycheck is dependent on you
- 59:16Speaker 2: doing that thing over and over and over again, it
- 59:19Speaker 2: can start feeling more like a chore than like fun.
- 59:21Speaker 2: So the actual advice I have is, like, pursue stuff
- 59:25Speaker 2: that you're pretty interested in that can pay you, whether
- 59:28Speaker 2: or not you're like most jobs are boring for a
- 59:30Speaker 2: lot of the time, so whether or not you're passionate
- 59:31Speaker 2: about it, a thing that you're like interested in and
- 59:34Speaker 2: like have an inclination for and have some skills at,
- 59:37Speaker 2: go do that for a career, and then use that
- 59:40Speaker 2: to like subsidize your ability to work on the fun stuff.
- 59:43Speaker 2: Like I, you know, like writing writing books and blogs
- 59:46Speaker 2: is like a thing I want to do independent of
- 59:48Speaker 2: the financial outcomes from it. I'm pivoted from media to
- 59:51Speaker 2: venture capital because, like, I like the offshoot opportunities of
- 59:55Speaker 2: investing in tech companies, and that's just like a better
- 59:59Speaker 2: world to be in for a career path.
- 1:00:01Speaker 1: Last question before we get to our favorite questions that
- 1:00:05Speaker 1: we ask all of our somewhat special guests.
- 1:00:08Speaker 2: What special guests?
- 1:00:09Speaker 1: How do I know I'm making the most of my time?
- 1:00:12Speaker 2: So the last chapter of the book is called are
- 1:00:15Speaker 2: You having Fun Yet? Which I think is like, I
- 1:00:18Speaker 2: think fun is an underrated barometer that you're actually doing
- 1:00:21Speaker 2: the right stuff with your life. And it sounds silly
- 1:00:24Speaker 2: at like first glance, but my take on it is,
- 1:00:27Speaker 2: I think the definition of fun and what you find
- 1:00:29Speaker 2: to be fun changes as you go through life different stages.
- 1:00:33Speaker 2: Where when I was like twenty three or twenty four,
- 1:00:35Speaker 2: it was just doing dumb, hostile hopping stuff and like
- 1:00:39Speaker 2: getting drunk all the time or whatever, and it was great.
- 1:00:41Speaker 2: Now I get drunk a lot less of the time.
- 1:00:43Speaker 2: It's still slightly a little bit more refined though, but
- 1:00:46Speaker 2: like you know, once you get a little further in
- 1:00:49Speaker 2: your career, like having real career success and making strides
- 1:00:52Speaker 2: is like a source of like joy and personal achievement.
- 1:00:56Speaker 2: When I was in college and playing football, like football
- 1:00:59Speaker 2: objectively sucked, but like I like, playing college football really sucks,
- 1:01:03Speaker 2: and anybody who's played it will tell you that.
- 1:01:05Speaker 1: But it's like a by the way, the description of
- 1:01:07Speaker 1: the work at routines in the six am wind sprints
- 1:01:09Speaker 1: and but but when you know deep into the season
- 1:01:13Speaker 1: the coach tap rains we get in there.
- 1:01:16Speaker 2: Yeah, it's like it's like an incredibly like fulfilled Like
- 1:01:19Speaker 2: it's like going from a walk on to be putting
- 1:01:21Speaker 2: on scholarship and then like getting made team captain my
- 1:01:23Speaker 2: senior year, Like that was a much cooler fulfilling moment
- 1:01:27Speaker 2: than like anything I did before or after it. Like
- 1:01:30Speaker 2: I think it was because it was really really hard, right.
- 1:01:32Speaker 1: So in a real sense of achievement.
- 1:01:34Speaker 2: Yeah, like it was a it was a hard thing
- 1:01:36Speaker 2: and I'd like executed on it, so but it was fun.
- 1:01:40Speaker 2: So my kind of definition of fun is if you
- 1:01:41Speaker 2: like find joy in the suck, then you're probably doing
- 1:01:44Speaker 2: the right thing. And like that could be being like
- 1:01:46Speaker 2: groggy and hungover like on a park mentioned Spain, but
- 1:01:50Speaker 2: you feel like you're living out an adventure, or it
- 1:01:52Speaker 2: could be like going after like a really ambitious career
- 1:01:55Speaker 2: and like excelling in it. And it's you know, I
- 1:01:58Speaker 2: think a lot of people as they get firs they're
- 1:02:00Speaker 2: in their careers, they keep chasing that ambition high off
- 1:02:03Speaker 2: of that to the detriment of like their family or
- 1:02:05Speaker 2: other parts of their life. I think a lot of
- 1:02:07Speaker 2: young people like just start like I think the biggest
- 1:02:11Speaker 2: mistake you can make is like keeping a prior version
- 1:02:15Speaker 2: of u's like benchmark or idea of what they should
- 1:02:18Speaker 2: be doing with their time and trying to like force
- 1:02:20Speaker 2: apply that to a future version, or trying to pull
- 1:02:24Speaker 2: forward a future version too early in your life at
- 1:02:26Speaker 2: the expense of the fun stuff you want to do now.
- 1:02:28Speaker 2: And I think just having a very very strong sense of, like,
- 1:02:33Speaker 2: what are the most important things right now that bring
- 1:02:35Speaker 2: me fulfillment and then going after those is the recipe
- 1:02:38Speaker 2: to a good life.
- 1:02:40Speaker 1: And the sequel to this fine joy in the suck
- 1:02:43Speaker 1: is a great.
- 1:02:44Speaker 2: Could be title. I just call it like middle aged money.
- 1:02:46Speaker 2: Once I get my thirties.
- 1:02:48Speaker 1: Well, you can do something every decade. You have a
- 1:02:50Speaker 1: built in model your money, slightly older money and money.
- 1:02:56Speaker 1: You got a whole run of things. All right, Let's
- 1:02:58Speaker 1: jump to our favorite questions that I ask even my
- 1:03:02Speaker 1: somewhat special guests, starting with you're still young, tell us
- 1:03:08Speaker 1: about your mentors? Did anybody really help shape your career?
- 1:03:12Speaker 2: Yeah? I mean the early mentors would have been football
- 1:03:15Speaker 2: coaches in high school and college defensive line coach Harold Brantley,
- 1:03:19Speaker 2: he was the man like he was. He was actually
- 1:03:21Speaker 2: whe who pushed me to the point that I could
- 1:03:23Speaker 2: play in college in the first place. And then my
- 1:03:25Speaker 2: college defensive line coach Kenny Baker was like I was.
- 1:03:29Speaker 2: I came into college playing in a small private high
- 1:03:32Speaker 2: school and thought I was And then I got to
- 1:03:34Speaker 2: college and just got wrecked for like a good year
- 1:03:37Speaker 2: and I was like really.
- 1:03:37Speaker 1: Good, faster, stronger, or you just didn't know the game
- 1:03:41Speaker 1: as well and didn't have the skills or some combination.
- 1:03:43Speaker 2: Like it was like I just had to get better.
- 1:03:46Speaker 1: It was like better shape, better skills.
- 1:03:48Speaker 2: I needed to get stronger and just be able to
- 1:03:50Speaker 2: react to the game on the field way faster. And
- 1:03:52Speaker 2: I just wasn't The processing speed and the just size
- 1:03:56Speaker 2: weren't there.
- 1:03:56Speaker 1: People don't realize that the quality of play at the
- 1:04:00Speaker 1: college level, it's astounding.
- 1:04:02Speaker 2: We played so we played Alabama, Little Mercy University. We
- 1:04:05Speaker 2: played Alabama and Auburn in the same year. I like
- 1:04:09Speaker 2: you want to talk about seeing like like like us.
- 1:04:13Speaker 2: We almost beat Auburn. We were down seven in the
- 1:04:15Speaker 2: fourth quarter, but Alabama Jalen Hurts to uh Mac Jones
- 1:04:20Speaker 2: smoked us. They had Calvin Ridley, all Pro receiver who
- 1:04:24Speaker 2: briefly had a gambling problem, but he's back as their
- 1:04:26Speaker 2: punt returner. Guess who started on the punt team was
- 1:04:28Speaker 2: getting juked out of his shoes like twenty times because
- 1:04:31Speaker 2: we punted so much. Me But defensive line coach Kenny
- 1:04:35Speaker 2: Baker was like, he I worked really hard, and he
- 1:04:38Speaker 2: could tell I did, and he was very encouraging and
- 1:04:40Speaker 2: that like keep the work ethic up and like you
- 1:04:44Speaker 2: will develop, like you will catch up to the point
- 1:04:46Speaker 2: that like, if you keep that work ethic, you'll be
- 1:04:48Speaker 2: able to play. And he was right. By my third season,
- 1:04:50Speaker 2: I was decent, and by my last season, I was
- 1:04:52Speaker 2: objectively good. Like I was never going to be an
- 1:04:54Speaker 2: All American, but I was like a starter and was
- 1:04:57Speaker 2: like a very solid player. But I could easily quit
- 1:05:00Speaker 2: and transferred to Georgia and like, you know, done the
- 1:05:03Speaker 2: fraternity thing at SEC school, which would have been short
- 1:05:05Speaker 2: term more fun, but long term less fulfilling. So football
- 1:05:09Speaker 2: coaches post post school, it's funny, like especially with COVID,
- 1:05:13Speaker 2: my early mentors were like kind of people I found
- 1:05:15Speaker 2: through Twitter. Like I remember when I read The Psychology
- 1:05:17Speaker 2: of Money. I thought it was like a very profound
- 1:05:19Speaker 2: book and I just like digested everything Morgan house Will published.
- 1:05:23Speaker 2: And then a year after that, like I remember when
- 1:05:26Speaker 2: he followed me back on Twitter. I was flying from Sevilla,
- 1:05:28Speaker 2: Spain to Manchester, England, and I looked at my phone.
- 1:05:31Speaker 2: I was like, Oh, this is really cool. This is
- 1:05:33Speaker 2: really cool. And then when I moved to New York,
- 1:05:35Speaker 2: we like hung out in person at Collob Fund's office
- 1:05:38Speaker 2: and like, like great guy, but I would say like
- 1:05:42Speaker 2: as a somewhat career slash just aspirational. Him and Tim
- 1:05:48Speaker 2: Urban were like my two favorite bloggers from the kind of.
- 1:05:51Speaker 1: Like you referenced Tim Urban in the book, but I
- 1:05:56Speaker 1: think you referenced a piece of his and I was
- 1:05:59Speaker 1: pro you didn't reference the piece on optionality, the so
- 1:06:04Speaker 1: to chart with the black lines.
- 1:06:05Speaker 2: Yeah, everybody steals it on Twitter.
- 1:06:08Speaker 1: I find that piece to be so interesting because you know,
- 1:06:12Speaker 1: one of the things about getting old is some of
- 1:06:15Speaker 1: your optionality goes away because you don't have Hey, this
- 1:06:19Speaker 1: is a twenty five year project. Do I really have
- 1:06:21Speaker 1: twenty five years?
- 1:06:22Speaker 2: Like?
- 1:06:23Speaker 1: What am I going to be doing at age? Ninety.
- 1:06:25Speaker 1: All right, maybe a twenty five year project isn't the
- 1:06:28Speaker 1: best thing for me or at age eighty best thing
- 1:06:31Speaker 1: for me to start. But I laughed at a lot
- 1:06:35Speaker 1: of your references because I'm familiar with many of them.
- 1:06:40Speaker 1: They were really really good. So so you mentioned Morgan,
- 1:06:43Speaker 1: any other post college mentors you want to bring up?
- 1:06:46Speaker 2: Yeah, I mean, like i'd say my current boss, Sam Lesson,
- 1:06:49Speaker 2: great guy. I mean he's a He's had a very
- 1:06:51Speaker 2: cool career, right, Like he like started a company in
- 1:06:54Speaker 2: his twenties in Brooklyn, ends up getting acquired by Facebook,
- 1:06:57Speaker 2: like had a successful career at Facebook, and then like
- 1:07:01Speaker 2: co founded the venture fund I work out now, right,
- 1:07:03Speaker 2: and like he's like, it's it's funny. I feel like
- 1:07:06Speaker 2: a lot of people in my bubble of like the
- 1:07:08Speaker 2: late twenties have this like is this what I want
- 1:07:11Speaker 2: to do with my career? You kind of hit this
- 1:07:12Speaker 2: inflection point of like you should pick a thing that
- 1:07:14Speaker 2: starts compounding, and like his take has always been like
- 1:07:18Speaker 2: you should just want to work with like really interesting,
- 1:07:20Speaker 2: smart people you respect and like work on interesting problems.
- 1:07:23Speaker 2: And that's a pretty good recipe for finding career fulfillment.
- 1:07:27Speaker 2: And you know, if a couple of things go right,
- 1:07:29Speaker 2: like financial success, but like it's I don't know. He
- 1:07:33Speaker 2: he's done like a few different things and now like
- 1:07:36Speaker 2: has like an objectively like I like if my lifestyle
- 1:07:39Speaker 2: and like life is set up kind of like his
- 1:07:40Speaker 2: in my forties, I'll be very cool with that. Like
- 1:07:42Speaker 2: so he crushes.
- 1:07:43Speaker 1: So you mentioned Morgan's books. Tell us what you're reading now?
- 1:07:48Speaker 1: What are some of your favorites.
- 1:07:49Speaker 2: So, I I just started reading this book called eighteen
- 1:07:52Speaker 2: seventy three. It's I think it came out pretty Yes.
- 1:07:55Speaker 1: Who won the Pulitzer for I forgot the name of
- 1:08:01Speaker 1: the four central bankers that his first book was about.
- 1:08:06Speaker 1: That is literally at the top of my queue, ready
- 1:08:08Speaker 1: to get.
- 1:08:08Speaker 2: It's how it's I'm about halfway through, and it's it's
- 1:08:12Speaker 2: like very good and interesting. I mean the thing I've
- 1:08:15Speaker 2: I've done this from time to time, Like I hadn't
- 1:08:16Speaker 2: read much over the last year while I was working
- 1:08:18Speaker 2: on that.
- 1:08:19Speaker 1: Yeah, now I'm writing is a kill you.
- 1:08:21Speaker 2: As someone who's written books, I had so underestimated, Like
- 1:08:25Speaker 2: I have much more respect for other authors after going
- 1:08:28Speaker 2: through that.
- 1:08:28Speaker 1: Exactly, can't you read books? You can't blog? You can't
- 1:08:31Speaker 1: It just sucks up so much.
- 1:08:33Speaker 2: Time with Yeah, it's like all your free time goes
- 1:08:35Speaker 2: to that. But something I've always liked is I've always
- 1:08:38Speaker 2: been a big biography guy or like certain moments or
- 1:08:41Speaker 2: events in history because you can get the chat, GPT whatever.
- 1:08:45Speaker 2: People can pull a story together in three hundred pages
- 1:08:48Speaker 2: of a thing is so fascinating, and with like eighteen
- 1:08:50Speaker 2: seventy three, like reading about the stock market speculation in
- 1:08:55Speaker 2: the like Vienna, Austria stock market in the eighteen seventies,
- 1:08:58Speaker 2: and then you're just pattern matching that again, it's like
- 1:09:00Speaker 2: what I saw with retail investing in twenty twenty, twenty
- 1:09:02Speaker 2: twenty one. It's you just see like human behavior playing
- 1:09:06Speaker 2: out cyclically one hundred and fifty years ago. Is just
- 1:09:09Speaker 2: really really interesting in like a you know, totally different
- 1:09:14Speaker 2: time and market and paradigm, but it's the exact same thing.
- 1:09:16Speaker 1: Lords of Finance was his first book that won the Pulitzer.
- 1:09:21Speaker 1: I'm excited about that book. Any of the books you
- 1:09:22Speaker 1: want to mention.
- 1:09:24Speaker 2: The Infinity Machine, the one about the DeepMind founders, it
- 1:09:28Speaker 2: was by Sebastian Mallaby. I think anyway, it's like as
- 1:09:32Speaker 2: far as Ai is now the thing everybody cares about.
- 1:09:34Speaker 2: He did a really good job of like like how
- 1:09:37Speaker 2: llms even became a thing in the first place, and
- 1:09:39Speaker 2: how like this is just group of like British researchers
- 1:09:43Speaker 2: who've been holed up in London the whole time kind
- 1:09:45Speaker 2: of kickstarted this whole AI boom. And even though Sam
- 1:09:48Speaker 2: Altman Elon Musk they aren't like main characters at all,
- 1:09:51Speaker 2: You're getting these interesting anecdotes of how like open AI
- 1:09:54Speaker 2: came to gather and how there was like a bit
- 1:09:55Speaker 2: of a coup with an open AI and then Elon leaves.
- 1:09:59Speaker 2: It just did a really good job of framing like
- 1:10:01Speaker 2: the current moment in time and how we got here.
- 1:10:04Speaker 2: But those are like I read both of those, who
- 1:10:05Speaker 2: have been reading both of those in the last month
- 1:10:07Speaker 2: and a half.
- 1:10:08Speaker 1: They're great interesting. What about streaming? What are you watching
- 1:10:12Speaker 1: or listening to give us your.
- 1:10:14Speaker 2: Favorite hilariously on the like on the On the podcast front,
- 1:10:18Speaker 2: I don't have any shows I listen to regularly, but
- 1:10:20Speaker 2: I will selectively if there's like a guest that I
- 1:10:23Speaker 2: find interesting for whatever reason. I've like it's everything from
- 1:10:26Speaker 2: tuning into like like Josh and Michael on the Compound
- 1:10:29Speaker 2: and Friends or like Tim Ferris's show or some Scott
- 1:10:34Speaker 2: Galloway stuff. It's I'm so much of a I have
- 1:10:38Speaker 2: people who I think are good interviewers. I don't care
- 1:10:40Speaker 2: about half the people they talked to, But occasionally they'll
- 1:10:43Speaker 2: have someone where I really want to hear that because
- 1:10:44Speaker 2: I think they'll pull out good questions, like I don't know,
- 1:10:48Speaker 2: Michael Lewis on Tim Ferris really good episode, or it's
- 1:10:52Speaker 2: there's nothing I listened to specifically streaming. I did like
- 1:10:55Speaker 2: that movie Obsession. I thought it was phenomenal. It was
- 1:10:58Speaker 2: the one that like when Megavi out of indie film
- 1:11:01Speaker 2: that when Mega viral out of nowhere in it? Who
- 1:11:04Speaker 2: directed it? It's the I can't even think of the
- 1:11:07Speaker 2: guy's name. He was got to start on YouTube. He
- 1:11:09Speaker 2: does a lot of short form comedy. But it like
- 1:11:11Speaker 2: blew up and it was the one about the guy
- 1:11:15Speaker 2: who like breaks the stick to make the girl like
- 1:11:17Speaker 2: he makes a wish that the girl falls in love
- 1:11:19Speaker 2: with him and then she goes full psycho. Anyway, it
- 1:11:22Speaker 2: went like nuclear on Twitter, Instagram, TikTok whatever, pretty good
- 1:11:26Speaker 2: horror film thriller. I liked it.
- 1:11:29Speaker 1: Final two questions, what sort of advice would you give
- 1:11:31Speaker 1: to a recent college grad interest in the career in
- 1:11:35Speaker 1: either writing, content creation or venture capital.
- 1:11:40Speaker 2: So my my take on all the career stuff for
- 1:11:44Speaker 2: that is, like, I think it's really I think that
- 1:11:46Speaker 2: one of the higher leverage things you can do is
- 1:11:48Speaker 2: just start a blog and put your thoughts out there,
- 1:11:50Speaker 2: even if you have five people reading it, fifty people
- 1:11:52Speaker 2: reading it. I think that especially with AI becoming more
- 1:11:57Speaker 2: and more of a thing, it's easy to like, like,
- 1:11:58Speaker 2: resumes are becoming incre something meaningless, both from like the
- 1:12:03Speaker 2: odds of somebody actually looking at your job application when
- 1:12:05Speaker 2: you send it in cold or very low, and the
- 1:12:07Speaker 2: ability to like lie, like you can make one hundred
- 1:12:11Speaker 2: different resumes with LMS based on the job you're applying
- 1:12:13Speaker 2: to now versus when I was, Like when I was
- 1:12:15Speaker 2: in college, you always tweak your cover letter or resume
- 1:12:18Speaker 2: per job, and it's pretty tedious to do that when
- 1:12:20Speaker 2: you're doing it by hand. You can make a million once, right,
- 1:12:23Speaker 2: So having some like like proof of your thoughts on thing,
- 1:12:30Speaker 2: or you've articulated ideas online that show how you think,
- 1:12:32Speaker 2: I think, carry a lot more. They've always been important,
- 1:12:35Speaker 2: but like stand out a lot more now with AI
- 1:12:37Speaker 2: or if you like AI coding assystems are really good,
- 1:12:41Speaker 2: like anybody can access them to build stuff. So just
- 1:12:43Speaker 2: having a portfolio of like written work or stuff you've
- 1:12:46Speaker 2: built online that shows that you took interest and initiative
- 1:12:50Speaker 2: and a thing and like put yourself out there super useful.
- 1:12:53Speaker 2: I mean. My my take on career stuff in general
- 1:12:56Speaker 2: is like if you can go into investment banking or
- 1:12:58Speaker 2: consulting right out of on you, it's still probably the
- 1:13:01Speaker 2: right move, just from like getting trained on how to
- 1:13:03Speaker 2: work hard. People who work at Goldman from twenty two
- 1:13:05Speaker 2: to twenty four are typically more competent than other people.
- 1:13:09Speaker 2: And for all my stuff about like you should go
- 1:13:12Speaker 2: take risk in your twenties, the caveat on that is
- 1:13:15Speaker 2: like you should have a couple of prestige STAPs first,
- 1:13:17Speaker 2: Like Columbia Business School was a prestige stap for me.
- 1:13:20Speaker 2: I enjoyed it, I learned a lot. The main reason
- 1:13:22Speaker 2: I went was like I went to a somewhat no
- 1:13:24Speaker 2: name undergrad. It's not like I worked at a marquee
- 1:13:27Speaker 2: firm out of undergrad. Like you want to get a
- 1:13:29Speaker 2: couple of like I have, like somebody's de risked me
- 1:13:33Speaker 2: as an individual. Then you go take the shots that
- 1:13:36Speaker 2: you want to, so like I it's like have a
- 1:13:40Speaker 2: collection of like independent work and thoughts like you can
- 1:13:42Speaker 2: share like in real time. And then I think it's
- 1:13:46Speaker 2: important to get one or two prestige STAPs before you
- 1:13:48Speaker 2: go jump off and do your own thing.
- 1:13:50Speaker 1: And yet in the book you talk about what a
- 1:13:53Speaker 1: what a misfocus it is hyping on status and why
- 1:13:58Speaker 1: that whole game is so cheah.
- 1:14:00Speaker 2: So the status thing's so nuanced. I think that if
- 1:14:04Speaker 2: you treat status as an ends to itself, you're going
- 1:14:07Speaker 2: to be incredibly disappointed. I think if you treat status
- 1:14:09Speaker 2: as a thing that you can acquire and leverage to
- 1:14:11Speaker 2: actually do ease to an end. Yes, like if the
- 1:14:14Speaker 2: trade is I'm going to go to an incredibly competitive
- 1:14:17Speaker 2: school and spend two to four years working in some
- 1:14:19Speaker 2: version of like Goldman, Blackstone, McKenzie, whatever, and I can
- 1:14:23Speaker 2: come out of that and do anything that's very much
- 1:14:26Speaker 2: worth it. But you don't want to be the person who,
- 1:14:29Speaker 2: like ten or fifteen years into their career never really
- 1:14:32Speaker 2: figured out their things. So kept chasing status is like
- 1:14:34Speaker 2: a vanity projects. It's like I say, status as diminishing
- 1:14:39Speaker 2: returns or like once you have enough of it, it
- 1:14:42Speaker 2: gets marginal. After that, you're good.
- 1:14:44Speaker 1: And our final question, what do you know about the
- 1:14:46Speaker 1: world of investing today? Might have been useful back when
- 1:14:51Speaker 1: you were locked in your bedroom trading specs.
- 1:14:54Speaker 2: I underestimated how much retail investing is like a permanent
- 1:14:58Speaker 2: fixture in the market today. I think it compounds from
- 1:15:01Speaker 2: like and this is all like public market stuff, but
- 1:15:04Speaker 2: like pod shops, trading, quarterback, quarter are like more and
- 1:15:07Speaker 2: more of a thing. Passive investing is more and more
- 1:15:09Speaker 2: of a thing. You could argue that true, like price
- 1:15:13Speaker 2: setters being like fundamental long short funds or and like
- 1:15:16Speaker 2: long only mutual funds are less of a thing. So
- 1:15:20Speaker 2: it's created this thing where you have like a lot
- 1:15:21Speaker 2: of like very short term trading on like whatever, alternative data,
- 1:15:25Speaker 2: quarterback quarter data, and then you have a lot of
- 1:15:27Speaker 2: passive stuff and then a really big active group is
- 1:15:30Speaker 2: like retail investing is a thing like game stop. I
- 1:15:33Speaker 2: thought was a one off fluke. It wasn't like open
- 1:15:35Speaker 2: door short squeeze out of nowhere. You're seeing like random
- 1:15:40Speaker 2: companies will just pop off like five percent, which makes
- 1:15:43Speaker 2: it like Dan Sundheim was on a podcast with the
- 1:15:45Speaker 2: Collison Brothers, the Stripe founders. A couple months ago, he
- 1:15:48Speaker 2: was talking about how they changed, like how they position
- 1:15:51Speaker 2: their shorts now d one capitals, because you just you
- 1:15:54Speaker 2: could be fundamentally right, but guess what, fundamentals don't matter
- 1:15:57Speaker 2: if the borrow rates through the roof and the stock
- 1:15:59Speaker 2: like eight and you get blown up right, like like
- 1:16:02Speaker 2: ask the game the Melvin Capitol guy about fundamentals when
- 1:16:05Speaker 2: his fun got blown up right like it. At the
- 1:16:08Speaker 2: end of the day, the only thing that matters is
- 1:16:09Speaker 2: making money. And I really thought a lot of that
- 1:16:13Speaker 2: was a twenty twenty twenty twenty one thing and it
- 1:16:15Speaker 2: was COVID and people were at home. We're seeing so
- 1:16:17Speaker 2: much stuff with like random speculative like nuclear reactor. Like
- 1:16:21Speaker 2: a company Akalo went public through a spack. It was
- 1:16:24Speaker 2: like a Sam Altman backed company. It was worth like
- 1:16:26Speaker 2: forty billion dollars. I don't think they have a functional reactor.
- 1:16:28Speaker 1: Yet, Like, are you suggesting that sites like Reddit, Wall
- 1:16:33Speaker 1: Street debts still carry the influence they used to or
- 1:16:37Speaker 1: has that attenuated and then it's spread out to die?
- 1:16:39Speaker 2: I would argue that they almost carry more weight because
- 1:16:42Speaker 2: I think that, like really, I think there's this is
- 1:16:44Speaker 2: pure speculation, but I think that they're now increasingly a
- 1:16:47Speaker 2: thing that like call it like institutional traders, quant funds, whatever,
- 1:16:51Speaker 2: we'll like look at as a data source where if
- 1:16:53Speaker 2: something spikes on one of these sites, they'll play the
- 1:16:56Speaker 2: momentum and like it makes these bubbles go even further
- 1:16:58Speaker 2: than they used to. And everything happens so fast now
- 1:17:01Speaker 2: because like the speed that information moves on the Internet
- 1:17:04Speaker 2: is just instantaneous. That like a bubble that might take
- 1:17:07Speaker 2: like months to build up and then collapse could happen
- 1:17:10Speaker 2: within a week both ways. So it's just like the
- 1:17:13Speaker 2: whole like internet spread of information faster and faster. It's
- 1:17:18Speaker 2: all all derivatives, like retail investors getting in the market
- 1:17:21Speaker 2: and then yapping about stuff online. That's just never gonna stop, right.
- 1:17:24Speaker 1: And it's so funny because everything old is new again.
- 1:17:28Speaker 1: Back in the day of the Yahoo message boards, like yeah,
- 1:17:32Speaker 1: like iomega and and that sort of stuff, nothing has changed.
- 1:17:36Speaker 1: It's just how much faster were.
- 1:17:39Speaker 2: And it's like zero commissions. Now it's like the there's.
- 1:17:42Speaker 1: And it's in your pocket, you know how let me
- 1:17:44Speaker 1: go home and call my broker does it?
- 1:17:46Speaker 2: And now there's like, oh we have prediction markets and
- 1:17:48Speaker 2: sports batting on your phone. We have removed all friction
- 1:17:51Speaker 2: from people putting money at risk to do stuff, and
- 1:17:54Speaker 2: we've made.
- 1:17:54Speaker 1: Regardless of how dumb or speculative it might.
- 1:17:56Speaker 2: Be, and the speed of which you can communicate what
- 1:17:58Speaker 2: you're doing is now all so instantaneous and free. So
- 1:18:01Speaker 2: you just have people constantly going risk on on whatever
- 1:18:05Speaker 2: for whatever reason, and then everybody else knows it. That's
- 1:18:08Speaker 2: just that's only going to keep accelerating.
- 1:18:10Speaker 1: Under except it kind of sounds like a very late
- 1:18:14Speaker 1: stage bullmarket.
- 1:18:16Speaker 2: Could have said that in twenty one and we were right,
- 1:18:17Speaker 2: twenty two is kind of a bear market. Then AI happened,
- 1:18:20Speaker 2: So it's like I think that. I just think market
- 1:18:23Speaker 2: cycles in general will keep happening faster and faster because
- 1:18:26Speaker 2: it'll collapse, people get blown up, and then somebody starts
- 1:18:29Speaker 2: running another thing. I just think it's going to get
- 1:18:31Speaker 2: more and more violent.
- 1:18:32Speaker 1: I have a pet thesis that the giant reset, the
- 1:18:36Speaker 1: giant fiscal stimulus and crash and recovery in twenty twenty
- 1:18:41Speaker 1: was like a reset and extent of the bullmark, and
- 1:18:43Speaker 1: another I agree with that ten years it's but anyway, Jack,
- 1:18:48Speaker 1: you you were more than a somewhat special guest.
- 1:18:52Speaker 2: Thanks.
- 1:18:52Speaker 1: This was really great. Thank you for being so generous
- 1:18:56Speaker 1: with your time. We have been speaking with Jack Rain's.
- 1:19:00Speaker 1: He is the author of Young Money, a field guide
- 1:19:03Speaker 1: to wealth and purpose in your twenties. If you enjoy
- 1:19:07Speaker 1: this conversation, well check out any of the six hundred
- 1:19:10Speaker 1: and fifty three we've done over the previous twelve years.
- 1:19:14Speaker 1: You can find those at iTunes, Spotify, YouTube, Bloomberg, or
- 1:19:19Speaker 1: wherever you find your favorite podcast. I would be remiss
- 1:19:23Speaker 1: if I didn't thank the crack team that helps us
- 1:19:25Speaker 1: put these conversations together each week. Alexis Noriega is my
- 1:19:30Speaker 1: video producer. Sean Russo is my researcher. Anna Luke is
- 1:19:35Speaker 1: my podcast producer. I'm Barry Rutoults. You've been listening to
- 1:19:40Speaker 1: Masters in Business on Bloomberg Radio.