WEBVTT - Optimizing Life and Finances in Your Twenties with Jack Raines

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<v Speaker 1>Bloomberg Audio Studios, Podcasts, radio News. This week on the

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<v Speaker 1>podcast My Somewhat Special Guest, Jack Rains is a venture

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<v Speaker 1>capitalist and author. I've been reading a substack for a

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<v Speaker 1>couple of years and always found it quite entertaining and interesting.

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<v Speaker 1>His new book Young Money, A field Guide to Wealth

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<v Speaker 1>and Purpose in your twenties, is really interesting and wise

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<v Speaker 1>beyond its years. I wish I had access to a

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<v Speaker 1>book like this one hundred years ago when I was

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<v Speaker 1>in my twenties. I thought this conversation was fascinating. I

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<v Speaker 1>think you will also, with no further ado, my interview

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<v Speaker 1>of Jack Rains. Jack Rains, Welcome to Bloomberg.

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<v Speaker 2>I mean, the extra special guest is way too kind,

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<v Speaker 2>but so my special guest, my normally special guest.

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<v Speaker 1>I wouldn't want to call him like my young guest.

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<v Speaker 1>My you know, I painted myself into the corner with

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<v Speaker 1>extra special guests. Why once you go that way, you

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<v Speaker 1>can never go back.

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<v Speaker 2>I'll take it.

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<v Speaker 1>Here's my special guest. Really, what's wrong with Jack? He's

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<v Speaker 1>a special were a cowboy hat? That's right. Well we'll

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<v Speaker 1>get into that a little bit. So let's roll back

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<v Speaker 1>so many years ago to when you're undergraduate studying finance

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<v Speaker 1>in Spanish while playing football and mercer. That was before

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<v Speaker 1>you got your MBA from Columbia. Was there ever a

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<v Speaker 1>career plan?

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<v Speaker 2>Like, not really, it was just I don't know. I

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<v Speaker 2>feel like basically every white dude ends up studying finance

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<v Speaker 2>unless they're dead set on going to like med school,

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<v Speaker 2>law school, or like computer science. So it was study finance,

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<v Speaker 2>and then I was set to graduate in two and

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<v Speaker 2>a half years because we had to take summer classes

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<v Speaker 2>with football, and I was like, I should double major

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<v Speaker 2>finance and marketing is stupid. I don't like computer science.

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<v Speaker 2>Let's pick up Spanish because it feels like that could

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<v Speaker 2>be marginally used living in the South. Spanish is very

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<v Speaker 2>assiassi right now, but it's like sufficient. There was no

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<v Speaker 2>real career path other than figure it out from there.

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<v Speaker 1>That's intriguing. I'm cracking up because they have so many

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<v Speaker 1>different ways to go with this. First gig out of

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<v Speaker 1>school was a corporate finance at UPS, which you described

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<v Speaker 1>as mostly moving a mouse around the screen and trying

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<v Speaker 1>to look busy. Correct tell us about your experience in

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<v Speaker 1>corporate finance.

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<v Speaker 2>Yeah, I mean to set the stage a little bit.

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<v Speaker 2>I graduated in December twenty nineteen, which was probably the

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<v Speaker 2>worst possible date to graduate, given that COVID started like

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<v Speaker 2>three weeks after that. So I moved to Atlanta in

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<v Speaker 2>January or February of twenty twenty start working for UPS.

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<v Speaker 2>I'm in the office for three days, my computer isn't

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<v Speaker 2>even fully online yet, and then we're told that we're

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<v Speaker 2>going remote for one week and then one month, and

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<v Speaker 2>then everybody had the same experience where a year and

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<v Speaker 2>a half later you're still remote. So I don't think

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<v Speaker 2>it's great to be a twenty two year old who's

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<v Speaker 2>never had a real job who's then told you're going

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<v Speaker 2>to work from home while you have like your Xbox

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<v Speaker 2>and all of your friends like doing the same thing.

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<v Speaker 2>And it was actually like a terrible environment to like

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<v Speaker 2>start learning how to be a worker. And yeah, it

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<v Speaker 2>was just zoom calls, Excel sheets like modeling out fuel

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<v Speaker 2>cost projections and forecast for UPS for like twenty twenty two. Yeah,

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<v Speaker 2>I was honestly bored the whole time. And to build

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<v Speaker 2>on top of that, I had gotten to business school

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<v Speaker 2>out of undergrad so like Columbia, I went to business

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<v Speaker 2>school at Columbia, and they have a deferred enrollment program

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<v Speaker 2>where when you're a senior in college, you apply and

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<v Speaker 2>then you work a few years and go to business school.

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<v Speaker 2>So I knew that I was going to go to

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<v Speaker 2>grad school in like three years. Covid hit. I was

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<v Speaker 2>super bored working remote, just doing basically nothing, and it

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<v Speaker 2>just kind of felt like I was in a work

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<v Speaker 2>from home purgatory for about eighteen months.

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<v Speaker 1>So having that window where, hey, I know where I'm

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<v Speaker 1>going to be eighteen months from now in September of

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<v Speaker 1>twenty twenty blank, what led you to say, I think

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<v Speaker 1>I'm going to quit and just buy a one way

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<v Speaker 1>ticket to Barcelona and travel the world. Like that's a

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<v Speaker 1>giant leap, which not a lot of people have the

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<v Speaker 1>nerve to make. What led to that decision?

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<v Speaker 2>So, Like, when I was a kid, I always loved

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<v Speaker 2>to travel, and my grandparents would take me everywhere.

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<v Speaker 1>Your grandma took you on a crazy trip you described

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<v Speaker 1>in the book to Savannah in Africa.

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<v Speaker 2>Yeah. Yeah, when I was eleven, my grandma Mama roof,

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<v Speaker 2>she I'm the oldest grandkid in the family, and she

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<v Speaker 2>hit me with the idea that she wanted to take

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<v Speaker 2>me on a trip like anywhere in the world I

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<v Speaker 2>wanted to go. I actually didn't know if she literally

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<v Speaker 2>met anywhere. I wanted to go, somewhere crazy, like Africa

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<v Speaker 2>or Asia. And we lived in South Georgia. Initially I

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<v Speaker 2>pitched Costa Rica and she said, too, you can. Yeah,

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<v Speaker 2>she said, like, that's like a three hour flight. I

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<v Speaker 2>was like, okay, Like I thought the like I had

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<v Speaker 2>a big map in my room as a kid, I

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<v Speaker 2>thought it'd be cool to go to the Ngoragora Crater

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<v Speaker 2>and see Mount Kilimanjarro and all this stuff. So she

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<v Speaker 2>took me and we went, and we went on a

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<v Speaker 2>two week safari and it was awesome. And then in

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<v Speaker 2>college I studied abroad in Spain. One summer, I went

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<v Speaker 2>to France. One summer with my best friend from college,

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<v Speaker 2>I did a service trip to Ecuador. Like I always

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<v Speaker 2>loved leaving the US, and it was kind of a

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<v Speaker 2>thing in the back of my head where I knew,

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<v Speaker 2>at some point in my twenties it would be really

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<v Speaker 2>fun to do like a multi month trip abroad with

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<v Speaker 2>like no itinerary other than just see other stuff. And

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<v Speaker 2>I was sitting there, It's like you have this, You're

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<v Speaker 2>working remote for eighteen months on your board, and then I,

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<v Speaker 2>for better or worse, had a fortuitous run trading spacks

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<v Speaker 2>and spack warrants during the pandemic, which gave me enough.

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<v Speaker 2>It gave me more money than I expected to have

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<v Speaker 2>at twenty three or twenty four, where I was like,

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<v Speaker 2>I mean, I I don't it wouldn't cost that much

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<v Speaker 2>to just go hostile hop Europe in Latin America for

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<v Speaker 2>a year.

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<v Speaker 1>Yeah, I'm glad you were up. You're not a trust

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<v Speaker 1>fund budd it, but baby, in any stretch of the imagination, no,

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<v Speaker 1>you scrape together some money, you fly coach, you staying

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<v Speaker 1>in hostels. You have ten roommates in these.

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<v Speaker 2>Places, eating like McDonald's or Euros or whatever. Every day.

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<v Speaker 2>It was the best. I mean, I got food poisoning oneside,

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<v Speaker 2>It was fun. It was fun.

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<v Speaker 1>The more recently, you wrote a story about going to

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<v Speaker 1>someone's winning and I think it was India and a

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<v Speaker 1>bunch of people got food poisoning and it was hilarious.

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<v Speaker 2>It feels a little bit like India right now in

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<v Speaker 2>New York. It's like the air quality today as of

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<v Speaker 2>recording is pretty similar.

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<v Speaker 1>To those Canadian fires. Are you walk out, it smells

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<v Speaker 1>like a bar because it's yellow.

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<v Speaker 2>It's like for microdosing New Deli era. Right now, it's great,

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<v Speaker 2>it's good stuff.

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<v Speaker 1>Only without the e coli that you described. But let's

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<v Speaker 1>bring it back to your career. So, so you do

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<v Speaker 1>this trip, you go through a couple of dozen countries,

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<v Speaker 1>you meet people that you're still friendly with. It was

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<v Speaker 1>really fascinating, and you get to business school. How do

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<v Speaker 1>you adjust? How do you make that transition?

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<v Speaker 2>Yeah? It was. It was interesting. Like I in the

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<v Speaker 2>back of my head, I kind of knew I had

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<v Speaker 2>this start date moving to New York in August twenty

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<v Speaker 2>twenty two. So I eventually quit my previous job, first

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<v Speaker 2>job out of college in August twenty one. It was

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<v Speaker 2>kind of like, all right, let's spend a year and

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<v Speaker 2>just have as much fun as physically possible, knowing that

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<v Speaker 2>then we're gonna go to grad school. Then we'll do

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<v Speaker 2>our career in New York and YadA, YadA, YadA. It

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<v Speaker 2>was funny because it was at first weird, like being

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<v Speaker 2>like I spent basically a full year out of the country,

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<v Speaker 2>jumping around a lot, and then you're in New York

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<v Speaker 2>and you have like a home base and you have

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<v Speaker 2>a business school. Is not a particularly strenuous thing, but

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<v Speaker 2>you do have a set schedule where you have classes

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<v Speaker 2>and stuff. I loved it though, I mean, I love Columbia, honestly,

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<v Speaker 2>I love New York in general, best city in the world,

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<v Speaker 2>particularly in your twenties. And it took a couple of

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<v Speaker 2>months to really get in the flow of like living

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<v Speaker 2>here and then also like you're meeting hundreds of new

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<v Speaker 2>people like that, but actually getting integrated not hard. It

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<v Speaker 2>felt like a perfect.

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<v Speaker 1>Fit, really really interesting. So I'm curious. You learn a

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<v Speaker 1>lot of things in both your office career or remote

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<v Speaker 1>work from home career and business school. What did you

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<v Speaker 1>learn about finance, money time while you were traveling.

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<v Speaker 2>I mean, the biggest thing that really jumped out was

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<v Speaker 2>It's something I write about a lot in the book,

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<v Speaker 2>like the I call it the stage specificity of life.

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<v Speaker 2>But by that I mean that it's pretty easy to

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<v Speaker 2>conceptualize money, like what you're taught from like in high school,

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<v Speaker 2>how money compounds over time if you invest in and

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<v Speaker 2>it's you know, you should be frugal and save up money,

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<v Speaker 2>but what you miss is like what's the optimal time

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<v Speaker 2>to spend that money on different things? And the example

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<v Speaker 2>that I give a lot is like I was twenty

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<v Speaker 2>four and like sleeping in a bunk bed in the

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<v Speaker 2>hostel with twelve roommates or whatever, and it was actually

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<v Speaker 2>just a hilarious setup. Like it's just a bunch of nonsense.

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<v Speaker 2>You have a French guy here and then like a

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<v Speaker 2>Mexican girl here, and it's like half the a lot

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<v Speaker 2>of the dorms are co ed, and it's like it's

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<v Speaker 2>like summer camp for like young adults. But then occasionally

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<v Speaker 2>you meet somebody in their like early thirties staying in

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<v Speaker 2>the same hostel and it's like you can almost tell

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<v Speaker 2>that they noticed they're like probably six or seven years

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<v Speaker 2>too late to have done that type of trip. And

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<v Speaker 2>like the biggest takeaway from traveling was like if I

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<v Speaker 2>really wanted to do this trip, this was the like

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<v Speaker 2>this was the right window to do this. Like I

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<v Speaker 2>optimized like that phase of my life correctly for somebody

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<v Speaker 2>who wanted to do that type of thing. And that's

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<v Speaker 2>kind of what stuck with me the most after is

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<v Speaker 2>not just being aware of what you want to get

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<v Speaker 2>out of life, but like what things have deadlines, where

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<v Speaker 2>like if that window of opportunity closes, you're just not

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<v Speaker 2>gonna be able to maximize your like fulfillment or enjoyment

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<v Speaker 2>or utility from that experience. Like every basically everything you

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<v Speaker 2>do in life has an expiration date for when you

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<v Speaker 2>would enjoy the most you can.

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<v Speaker 1>You can go cheap and cheerful in your twenties, maybe

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<v Speaker 1>even early thirties, but not much past. Correct, So you

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<v Speaker 1>were also writing before the trip and during the trip.

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<v Speaker 1>Tell us a little bit about your experience, what you

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<v Speaker 1>discovered about yourself as you're writing, and why you thought

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<v Speaker 1>that might be a career path.

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<v Speaker 2>So like, Hilariously, when I was doing the whole spac

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<v Speaker 2>trading thing in twenty twenty and twenty twenty one, I

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<v Speaker 2>had a burner Reddit account called Barmelo's Anthony. It's a

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<v Speaker 2>play on words on Barmelo, Carmelo, Anthony, and xanax bars.

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<v Speaker 2>It was my name of my college group me. We

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<v Speaker 2>all had edgy like drug related famous person combination names.

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<v Speaker 2>I was writing so much stuff about, Like, oh, like

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<v Speaker 2>Apollo changed the background header of their website from oil

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<v Speaker 2>rigs to windmills. I think they're going to take an

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<v Speaker 2>ev company public through a spack And then they announced

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<v Speaker 2>a deal with Fiscarado motive. Three weeks later it was

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<v Speaker 2>like borderline conspiracy theory stuff, but it worked a lot

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<v Speaker 2>of it worked. Yeah, So I like always liked just

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<v Speaker 2>writing about like stuff I was seeing going on in markets.

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<v Speaker 2>And then when I was when I was traveling, I

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<v Speaker 2>tried to get hired by The Morning Brew, the Hustle,

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<v Speaker 2>a few different like kind of upstart ish media companies.

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<v Speaker 2>Nobody would hire me for lack of like professional writing experience.

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<v Speaker 2>So I just started writing, like I just launched a

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<v Speaker 2>sub stack and started writing a newsletter. And it was

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<v Speaker 2>like half investing in finance and half travel blog, like

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<v Speaker 2>detailing everything I was doing day to day, who I

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<v Speaker 2>was meeting, and I just enjoyed it, Like it's writing

0:11:30.320 --> 0:11:32.520
<v Speaker 2>something I've always found fun. I've always found it a

0:11:32.520 --> 0:11:35.040
<v Speaker 2>bit cathartic, like putting your thoughts on paper, and it's

0:11:35.080 --> 0:11:37.520
<v Speaker 2>a good I don't know, I think it's like a

0:11:37.559 --> 0:11:41.480
<v Speaker 2>good exercise for anybody to really like distill what you

0:11:41.559 --> 0:11:43.319
<v Speaker 2>think about a thing is try to sit down and

0:11:43.320 --> 0:11:44.200
<v Speaker 2>put pin on paper.

0:11:44.640 --> 0:11:49.320
<v Speaker 1>So Daniel Borston, the Librarian to Congress is famous quote,

0:11:49.360 --> 0:11:51.080
<v Speaker 1>I write to figure out what I think.

0:11:51.240 --> 0:11:51.440
<v Speaker 2>Yep.

0:11:51.600 --> 0:11:54.840
<v Speaker 1>And besides, at that hour, the bars were all closed.

0:11:54.960 --> 0:11:55.160
<v Speaker 2>Yep.

0:11:55.360 --> 0:11:58.200
<v Speaker 1>So you know, until you put it down, until you

0:11:58.240 --> 0:12:01.960
<v Speaker 1>put pen to paper, a finger to keyboard, it's sort

0:12:02.000 --> 0:12:06.320
<v Speaker 1>of nebulous and not distinct. Once you write it there

0:12:06.360 --> 0:12:09.120
<v Speaker 1>it is black and white. Yeah. Yeah, so for sure.

0:12:09.960 --> 0:12:13.280
<v Speaker 1>So you come out of Columbia, what's the first gig

0:12:13.360 --> 0:12:16.440
<v Speaker 1>you're doing while you're while you're a new grad.

0:12:16.559 --> 0:12:18.680
<v Speaker 2>So, so to step back a little bit, when I

0:12:18.720 --> 0:12:20.880
<v Speaker 2>was still in business school, I kind of had this like,

0:12:21.520 --> 0:12:25.040
<v Speaker 2>I think investing in financial markets are interesting. I really

0:12:25.080 --> 0:12:29.360
<v Speaker 2>like writing. I had like monetize my newsletter fairly well

0:12:29.400 --> 0:12:31.280
<v Speaker 2>selling ads, and I was kind of trying to figure

0:12:31.280 --> 0:12:33.120
<v Speaker 2>out which way I wanted to lean with it. And

0:12:33.120 --> 0:12:35.440
<v Speaker 2>then I had some publishers who were like loosely interested

0:12:35.480 --> 0:12:37.800
<v Speaker 2>in me maybe writing a book. So I wanted to

0:12:37.880 --> 0:12:41.520
<v Speaker 2>leave the book writing door open. And I interned for

0:12:41.559 --> 0:12:45.200
<v Speaker 2>a venture capital fund called Red Point Ventures my first year,

0:12:45.320 --> 0:12:47.760
<v Speaker 2>helping them with like building up a newsletter and like

0:12:48.120 --> 0:12:52.160
<v Speaker 2>editorial strategy and all that stuff. It was like love

0:12:52.200 --> 0:12:54.320
<v Speaker 2>the team there, it was great. My takeaway from that

0:12:54.600 --> 0:12:58.480
<v Speaker 2>was I should either like go do media or I

0:12:58.520 --> 0:13:01.200
<v Speaker 2>should like push you get in like investing seat somewhere,

0:13:01.920 --> 0:13:04.319
<v Speaker 2>not split the middle and do like the marketing arm

0:13:04.400 --> 0:13:07.720
<v Speaker 2>of an investment group. So going into my second year,

0:13:08.600 --> 0:13:11.840
<v Speaker 2>Sam Row, you know, Front of the Show. He was

0:13:11.920 --> 0:13:14.240
<v Speaker 2>like contracted by Robin Hood to help them with the

0:13:14.360 --> 0:13:17.280
<v Speaker 2>hiring for they were building out a media subsidiary called

0:13:17.280 --> 0:13:21.000
<v Speaker 2>Sherwood News. We grabbed coffee and he was like, I

0:13:21.040 --> 0:13:23.959
<v Speaker 2>don't know what your plan is after business school. I

0:13:23.960 --> 0:13:25.640
<v Speaker 2>think you'd be a good fit with what they're building here.

0:13:25.640 --> 0:13:27.720
<v Speaker 2>And he started telling me about it, and it checked

0:13:27.720 --> 0:13:30.520
<v Speaker 2>a lot of boxes of like, on one hand, it

0:13:30.600 --> 0:13:32.960
<v Speaker 2>was kind of an upstart new media thing with like

0:13:33.040 --> 0:13:35.040
<v Speaker 2>I would have a lot of autonomy. On the other hand,

0:13:35.400 --> 0:13:37.319
<v Speaker 2>we were surrounded by the structure of like a big

0:13:37.360 --> 0:13:40.440
<v Speaker 2>fintech company, so, like media is a tough business these days,

0:13:40.440 --> 0:13:42.360
<v Speaker 2>and there was a lot more stability there from like

0:13:42.400 --> 0:13:43.240
<v Speaker 2>financial backing.

0:13:43.640 --> 0:13:47.280
<v Speaker 1>Tell me about having a media outlet attached to a

0:13:47.360 --> 0:13:49.679
<v Speaker 1>large fintech or data services company.

0:13:50.040 --> 0:13:52.400
<v Speaker 2>The entire pitch was just trying to like basically make

0:13:52.440 --> 0:13:54.240
<v Speaker 2>a new Age Bloomberg tell you the truth.

0:13:54.640 --> 0:13:57.240
<v Speaker 1>Did you guys get any hood stock?

0:13:57.720 --> 0:13:59.559
<v Speaker 2>Yeah? Yeah, yeah, so not.

0:13:59.600 --> 0:14:00.800
<v Speaker 1>Terrible, not terrible.

0:14:00.840 --> 0:14:02.280
<v Speaker 2>I mean the issue was I only worked there for

0:14:02.280 --> 0:14:03.800
<v Speaker 2>a year, so it's not like I got that much

0:14:03.840 --> 0:14:06.560
<v Speaker 2>but like it. Yeah, like I wish I would have

0:14:06.800 --> 0:14:08.440
<v Speaker 2>I wish I would have gotten more, and I wish

0:14:08.440 --> 0:14:10.520
<v Speaker 2>I would have stayed longer had I gotten more, is

0:14:11.160 --> 0:14:13.080
<v Speaker 2>the takeaway from that. But yeah, I ended up ended

0:14:13.120 --> 0:14:15.920
<v Speaker 2>up joining them during my second year. I signed the

0:14:15.920 --> 0:14:18.680
<v Speaker 2>book deal for that book the summer after I graduated.

0:14:18.720 --> 0:14:20.840
<v Speaker 2>It's about two years ago now, and then I was

0:14:20.880 --> 0:14:24.560
<v Speaker 2>sitting there and I just like everything was fine. But

0:14:24.680 --> 0:14:29.040
<v Speaker 2>I realized after working in a like more structured media environment,

0:14:29.080 --> 0:14:31.240
<v Speaker 2>I actually like like I like writing a blog. I

0:14:31.320 --> 0:14:34.120
<v Speaker 2>like kind of free range putting stuff on the internet,

0:14:34.160 --> 0:14:36.680
<v Speaker 2>but like I didn't like the actual like like call

0:14:36.680 --> 0:14:39.880
<v Speaker 2>it nine to five employed version of like financial media,

0:14:40.440 --> 0:14:43.160
<v Speaker 2>and my like it kind of clicked to my head

0:14:43.200 --> 0:14:45.560
<v Speaker 2>that when I was at that point of investing thing

0:14:45.720 --> 0:14:49.520
<v Speaker 2>versus like media, I actually probably should have gone investing track,

0:14:49.680 --> 0:14:52.200
<v Speaker 2>but I was so hyper focused on like I don't

0:14:52.200 --> 0:14:54.080
<v Speaker 2>want to kill a potential book deal momentum and this

0:14:54.160 --> 0:14:56.040
<v Speaker 2>and that that I took the other one and I

0:14:56.080 --> 0:14:59.680
<v Speaker 2>had like a total career panic, like to almost too

0:15:00.040 --> 0:15:01.640
<v Speaker 2>most two years ago, like fall twenty four.

0:15:02.000 --> 0:15:04.640
<v Speaker 1>And there is something to be said about the daily

0:15:04.720 --> 0:15:08.520
<v Speaker 1>beast that must be fed when you're on a regular deadline,

0:15:08.640 --> 0:15:11.840
<v Speaker 1>Like that's tough. Yeah, no, it's brutal. And it's why

0:15:11.880 --> 0:15:15.520
<v Speaker 1>there's so much content that's so useless, because hey, there

0:15:15.560 --> 0:15:20.960
<v Speaker 1>are minutes and hours to fill in column inches and

0:15:21.000 --> 0:15:23.680
<v Speaker 1>the infinite more of the Internet. I mean, it just

0:15:23.720 --> 0:15:27.960
<v Speaker 1>never stops. So that's why we have this fire hose. So,

0:15:28.480 --> 0:15:33.720
<v Speaker 1>so you had done Young Money as a sub stack,

0:15:33.840 --> 0:15:37.240
<v Speaker 1>you had done Sherwood for Robinhood. I'm kind of fast

0:15:37.240 --> 0:15:39.640
<v Speaker 1>anybody in an essay you did how I lost one

0:15:39.680 --> 0:15:43.040
<v Speaker 1>hundred and fifty thousand dollars in a day trading SPACs

0:15:43.200 --> 0:15:46.960
<v Speaker 1>yep way back in twenty one. Tell us about your

0:15:47.120 --> 0:15:50.240
<v Speaker 1>ramp up in the spac world and then the blow up.

0:15:50.360 --> 0:15:52.600
<v Speaker 2>Oh it was, I mean it was awesome, like like

0:15:52.960 --> 0:15:55.600
<v Speaker 2>I like I was. I don't know if you would

0:15:55.600 --> 0:15:58.160
<v Speaker 2>have checked my pulse or stress levels at that point

0:15:58.240 --> 0:16:00.400
<v Speaker 2>they were through the roof, but like it was crazy.

0:16:00.520 --> 0:16:04.160
<v Speaker 2>So it's like, right when the pandemic hit, I thought

0:16:04.200 --> 0:16:06.200
<v Speaker 2>I was like the next Michael Burry. I had like

0:16:06.280 --> 0:16:09.320
<v Speaker 2>ten thousand dollars in my checking account, threw it all

0:16:09.320 --> 0:16:12.720
<v Speaker 2>in spy puts. They tripled because obviously the market was

0:16:12.760 --> 0:16:14.920
<v Speaker 2>going to take and I was like, yeah, I'm him,

0:16:15.320 --> 0:16:17.800
<v Speaker 2>and then you know Bill Ackman. A week later, it

0:16:17.840 --> 0:16:20.160
<v Speaker 2>was like crying on CNBC say the world's going to hell,

0:16:20.200 --> 0:16:22.760
<v Speaker 2>and I was like, SMP's going to like a thousand,

0:16:22.880 --> 0:16:25.880
<v Speaker 2>let's do it again, let's buy more puts. You know,

0:16:25.960 --> 0:16:29.400
<v Speaker 2>I actually, having not really been an adult during eight

0:16:29.440 --> 0:16:32.760
<v Speaker 2>I completely underestimated like the FED and quantitative easy.

0:16:32.640 --> 0:16:35.120
<v Speaker 1>And how that could work and how fast that turn is.

0:16:35.440 --> 0:16:38.200
<v Speaker 2>Like I my face got melted off. I shortened the

0:16:38.240 --> 0:16:41.080
<v Speaker 2>actual bottom and then I basically round tripped ten thousand

0:16:41.120 --> 0:16:43.240
<v Speaker 2>dollars to thirty back to ten. I have my tailtop

0:16:43.280 --> 0:16:45.040
<v Speaker 2>between my legs and I was like, I'm never trading

0:16:45.080 --> 0:16:45.400
<v Speaker 2>a stock.

0:16:45.640 --> 0:16:47.960
<v Speaker 1>Did you ever feel the need to reach over to

0:16:47.960 --> 0:16:50.080
<v Speaker 1>the waste paper basket and throw up? No?

0:16:50.360 --> 0:16:52.880
<v Speaker 2>But like if it had been bigger numbers, maybe, so

0:16:53.080 --> 0:16:55.080
<v Speaker 2>I'm like, I'm never going to trade stocks again. I

0:16:55.160 --> 0:16:57.560
<v Speaker 2>put six thousand dollars in. I opened like a roth

0:16:57.600 --> 0:17:00.560
<v Speaker 2>Ira do my one contribution first years a you know,

0:17:00.800 --> 0:17:03.840
<v Speaker 2>adult working, and I don't look at it for a month.

0:17:04.040 --> 0:17:07.600
<v Speaker 2>And then in May my friend Jake Buddy from undergrad

0:17:07.760 --> 0:17:10.239
<v Speaker 2>was like, do you know what a spack is? I

0:17:10.280 --> 0:17:12.760
<v Speaker 2>say no, and he's like, well, if you buy this

0:17:12.840 --> 0:17:16.239
<v Speaker 2>Desert Eagle spack, It'll turn into DraftKings stock in like

0:17:16.320 --> 0:17:19.040
<v Speaker 2>two months. And I was like, it's like like an ipo,

0:17:19.119 --> 0:17:20.880
<v Speaker 2>and he's like, I don't know, dude, I just saw

0:17:20.920 --> 0:17:22.760
<v Speaker 2>on the internet. If I buy this, you owned Draft Kings.

0:17:22.800 --> 0:17:25.040
<v Speaker 2>And I was like, okay, I went now the rabbit

0:17:25.040 --> 0:17:26.320
<v Speaker 2>hole was looking at it, and it's like.

0:17:26.880 --> 0:17:29.840
<v Speaker 1>And it's a pars. It's before it comes out. It

0:17:29.920 --> 0:17:32.320
<v Speaker 1>was it trading? It was it did trade up.

0:17:32.400 --> 0:17:35.680
<v Speaker 2>It was trading because so the par on most spacks

0:17:35.760 --> 0:17:37.600
<v Speaker 2>is like ten dollars, and it was trading at like

0:17:37.640 --> 0:17:40.879
<v Speaker 2>twelve or thirteen. Oh really maybe fifteen. But the warrants

0:17:40.920 --> 0:17:42.760
<v Speaker 2>had like doubled or tripled, right, because all the warrants

0:17:42.800 --> 0:17:45.520
<v Speaker 2>have a strike price of eleven fifty. So then I

0:17:45.560 --> 0:17:49.040
<v Speaker 2>had like traded options enough. I understood like strike prices,

0:17:49.080 --> 0:17:52.080
<v Speaker 2>expiration dates, whatever. And the thing that jumps out was

0:17:52.119 --> 0:17:54.119
<v Speaker 2>that warrants don't expire for five years and they have

0:17:54.119 --> 0:17:56.600
<v Speaker 2>an eleven fifty strike price. So I was doing the

0:17:56.640 --> 0:17:59.440
<v Speaker 2>math and I watched DraftKings. After the merger happened, it

0:17:59.520 --> 0:18:01.680
<v Speaker 2>ran out to the warrants ran up to eight or

0:18:01.760 --> 0:18:04.320
<v Speaker 2>nine dollars. You would have doubled on the stock. We

0:18:04.359 --> 0:18:06.080
<v Speaker 2>would have made like nine x on the warrants if

0:18:06.080 --> 0:18:09.600
<v Speaker 2>you bought them at a dollar, like at peak pandemic collapse.

0:18:09.760 --> 0:18:12.840
<v Speaker 1>So I was like, okay, if like this is easy, well,

0:18:12.880 --> 0:18:13.160
<v Speaker 1>I was.

0:18:13.119 --> 0:18:15.800
<v Speaker 2>Just like spacks obviously kind of seemed like a bubble

0:18:15.880 --> 0:18:18.080
<v Speaker 2>right now, because there'd been like Nikolai Motors had announce

0:18:18.080 --> 0:18:19.639
<v Speaker 2>a Spack and there were a couple of others, and

0:18:19.680 --> 0:18:22.320
<v Speaker 2>I was just like, I bet that this thing is

0:18:22.359 --> 0:18:24.760
<v Speaker 2>gonna like this is just gonna be a game for

0:18:24.800 --> 0:18:26.199
<v Speaker 2>a little while. And if I can just pick the

0:18:26.240 --> 0:18:28.200
<v Speaker 2>spack warrants early, I bet I can make money. So

0:18:28.520 --> 0:18:31.080
<v Speaker 2>Nicola warrants to trade at three dollars, I bought six

0:18:31.119 --> 0:18:33.720
<v Speaker 2>thousand dollars worth. I made like twelve grand a couple

0:18:33.800 --> 0:18:36.240
<v Speaker 2>weeks later, and then I just kept rinting and repeating

0:18:36.280 --> 0:18:39.680
<v Speaker 2>spack warrants, and like six months later, I got from

0:18:39.720 --> 0:18:41.600
<v Speaker 2>six grand to one hundred and fifty grand, and I

0:18:41.680 --> 0:18:42.679
<v Speaker 2>was like, this is so easy.

0:18:42.800 --> 0:18:46.520
<v Speaker 1>So then I, by the way, oh that that should

0:18:46.560 --> 0:18:48.360
<v Speaker 1>immediately set bells off.

0:18:48.480 --> 0:18:50.760
<v Speaker 2>I doubled down, though it didn't set off any bells,

0:18:50.800 --> 0:18:53.159
<v Speaker 2>because then I was like, okay, it did set off

0:18:53.160 --> 0:18:55.359
<v Speaker 2>one bell. I was like, warrants are risky, and if

0:18:55.359 --> 0:18:57.800
<v Speaker 2>any of these deals collapses, the warrants go to zero,

0:18:58.320 --> 0:19:01.400
<v Speaker 2>I should start buying the shares close to NAV as possible.

0:19:01.600 --> 0:19:04.399
<v Speaker 2>So I was in like an online discord chat with

0:19:04.480 --> 0:19:06.640
<v Speaker 2>a lot of other anonymous people. We built some web

0:19:06.680 --> 0:19:10.560
<v Speaker 2>scrapers that will pull every spac SEC filing, so as

0:19:10.600 --> 0:19:13.240
<v Speaker 2>soon as the filing hit the press, like trading halts,

0:19:13.280 --> 0:19:15.720
<v Speaker 2>when news comes out for a spec, I would get

0:19:15.720 --> 0:19:18.879
<v Speaker 2>a push notification, open up the deck, skim it. If

0:19:18.960 --> 0:19:23.760
<v Speaker 2>it was electric vehicles, marijuana, outer space, sports, betting, or

0:19:23.800 --> 0:19:27.240
<v Speaker 2>renewable energy, I would go all in unless the unless

0:19:27.320 --> 0:19:29.920
<v Speaker 2>the like valuation of the deal was just egregious, I

0:19:29.920 --> 0:19:32.600
<v Speaker 2>would go all in. And I knew that the stock

0:19:32.600 --> 0:19:34.879
<v Speaker 2>would probably pop like at least thirty or forty percent,

0:19:34.960 --> 0:19:38.240
<v Speaker 2>because they just did every time. So you get in

0:19:38.280 --> 0:19:41.560
<v Speaker 2>an eleven, your max loss is probably like five percent

0:19:41.600 --> 0:19:44.040
<v Speaker 2>on any trade, and you sell it fourteen or fifteen,

0:19:44.080 --> 0:19:47.320
<v Speaker 2>so you're basically risking five percent to make forty percent.

0:19:47.040 --> 0:19:49.240
<v Speaker 1>Of asymmetrical risk reward. That's what you want.

0:19:49.320 --> 0:19:51.320
<v Speaker 2>And I did that like seven times in a row,

0:19:51.320 --> 0:19:53.160
<v Speaker 2>and then I went from one fifty to four hundred

0:19:53.240 --> 0:19:55.560
<v Speaker 2>and like I'd only risked on any given trade, like

0:19:55.600 --> 0:19:58.040
<v Speaker 2>five percent of my portfolio, and they didn't all hit,

0:19:58.119 --> 0:20:01.560
<v Speaker 2>but like enough did that it didn't matter. And my dad, obviously,

0:20:01.640 --> 0:20:03.240
<v Speaker 2>I kept telling him what I was doing, and I

0:20:03.320 --> 0:20:06.080
<v Speaker 2>hit like it was February twenty twenty one, and he

0:20:06.160 --> 0:20:08.119
<v Speaker 2>called me and he was like, you should probably just

0:20:08.240 --> 0:20:10.399
<v Speaker 2>sell and just put it in like an index fund.

0:20:10.400 --> 0:20:12.440
<v Speaker 2>And I was like, I knew this two more times,

0:20:12.440 --> 0:20:14.320
<v Speaker 2>I'll have a million dollars at twenty four. I'm pretty

0:20:14.320 --> 0:20:17.159
<v Speaker 2>sure I can get there. That should have been the.

0:20:17.160 --> 0:20:19.320
<v Speaker 1>Screen is the bell ringing that?

0:20:19.440 --> 0:20:21.399
<v Speaker 2>And then when he and his brother were talking to

0:20:21.400 --> 0:20:24.280
<v Speaker 2>me about potentially managing some of our family's money. You

0:20:24.280 --> 0:20:26.040
<v Speaker 2>shouldn't have your twenty four year old kid, he just

0:20:26.080 --> 0:20:28.840
<v Speaker 2>made six thousand percent trading spacks, touching your grandparents like

0:20:28.880 --> 0:20:31.360
<v Speaker 2>retirement money. I did not, thankfully. I said, I don't

0:20:31.400 --> 0:20:33.840
<v Speaker 2>feel comfortable doing that. I'm okay. I was self aware

0:20:33.920 --> 0:20:36.600
<v Speaker 2>enough to know that would have been a bad idea.

0:20:36.760 --> 0:20:39.359
<v Speaker 2>So getting to how I lose the money at this point,

0:20:39.440 --> 0:20:42.280
<v Speaker 2>way too many spacks. Shaquille O'Neil has a spack, Paul

0:20:42.359 --> 0:20:44.800
<v Speaker 2>Ryan has a spack. Like everybody and their mother has

0:20:44.840 --> 0:20:48.520
<v Speaker 2>a spack and the bubble didn't pop. It just stopped

0:20:48.560 --> 0:20:50.720
<v Speaker 2>bubbling because there there was kind of this pool of

0:20:50.800 --> 0:20:53.320
<v Speaker 2>money that was chasing every hot spack and then there's

0:20:53.359 --> 0:20:55.280
<v Speaker 2>like one hundred of them on the market. Somebody announce

0:20:55.359 --> 0:20:57.440
<v Speaker 2>is a deal, the terms are getting worse and worse,

0:20:57.920 --> 0:20:59.159
<v Speaker 2>and the value.

0:20:58.960 --> 0:21:00.640
<v Speaker 1>You're watching this to k in real time.

0:21:00.720 --> 0:21:03.160
<v Speaker 2>Yeah, And it was like by April May of that year,

0:21:03.200 --> 0:21:06.160
<v Speaker 2>it's getting tougher and like a deal would get announced

0:21:06.200 --> 0:21:08.479
<v Speaker 2>might jump ten percent. You're just I was like I

0:21:08.520 --> 0:21:12.080
<v Speaker 2>was addicted to the rush. So there was a buy now,

0:21:12.160 --> 0:21:15.280
<v Speaker 2>pay later company called Catapult. Eighty percent of the revenue

0:21:15.320 --> 0:21:19.040
<v Speaker 2>came from Wayfair, obviously a pandemic darling. And this is

0:21:19.080 --> 0:21:22.320
<v Speaker 2>at the time when Square bought After Pay for like

0:21:22.359 --> 0:21:25.320
<v Speaker 2>thirty billion dollars crazy price. A firm went public at

0:21:25.320 --> 0:21:28.040
<v Speaker 2>like a thirty billion dollar valuation, and like these companies

0:21:28.400 --> 0:21:31.600
<v Speaker 2>were growing slower than Catapult because Catapult was just a

0:21:31.600 --> 0:21:34.080
<v Speaker 2>derivative of Wayfair, which is a pandemic darling. They were

0:21:34.240 --> 0:21:36.960
<v Speaker 2>less profitable and I was just like, Catapult's gonna have

0:21:37.000 --> 0:21:40.119
<v Speaker 2>their earnings in August. They've had no cell side coverage.

0:21:40.280 --> 0:21:44.199
<v Speaker 2>I just need like one analyst from like Morgan Stanley

0:21:44.280 --> 0:21:47.160
<v Speaker 2>or whatever to initiate like a buy the stock's gonna double,

0:21:47.200 --> 0:21:48.600
<v Speaker 2>I'm gonna buy a bunch of warrants at like a

0:21:48.640 --> 0:21:51.320
<v Speaker 2>dollar fifty they're gonna rip. And then this thing, like

0:21:51.359 --> 0:21:53.480
<v Speaker 2>I'm gonna make a million dollars on this trade. This

0:21:53.520 --> 0:21:55.280
<v Speaker 2>thing had already gone public through a spac, Like there

0:21:55.320 --> 0:21:57.000
<v Speaker 2>was no floor, that deal was closed. It's just a

0:21:57.080 --> 0:21:58.000
<v Speaker 2>normal company.

0:21:57.800 --> 0:22:00.199
<v Speaker 1>So not your traditional spac trades that you've been doing.

0:22:01.119 --> 0:22:03.080
<v Speaker 2>It had gone public through a spack and it's just

0:22:03.080 --> 0:22:06.160
<v Speaker 2>like a normal company at this point. And I I

0:22:06.320 --> 0:22:08.879
<v Speaker 2>just aped into it with like three hundred I think

0:22:08.880 --> 0:22:10.359
<v Speaker 2>I had like three hundred and thirty thousand dollars at

0:22:10.400 --> 0:22:13.000
<v Speaker 2>that point. Just went all in and it started like

0:22:13.080 --> 0:22:15.439
<v Speaker 2>inching down and spike back up leading up to earnings,

0:22:15.480 --> 0:22:17.240
<v Speaker 2>like I had four different times I could have gone

0:22:17.240 --> 0:22:19.280
<v Speaker 2>out with like a ten percent loss, and I was

0:22:19.359 --> 0:22:21.840
<v Speaker 2>just like I was just pot committed to, like this

0:22:21.880 --> 0:22:24.760
<v Speaker 2>is gonna be the millionaire trade. They missed earning so

0:22:24.880 --> 0:22:27.240
<v Speaker 2>badly that the stock fell. I think the stock fell

0:22:27.359 --> 0:22:30.800
<v Speaker 2>twenty percent before market opened on like August eleventh, and

0:22:30.800 --> 0:22:33.320
<v Speaker 2>the warrants immediately got cut in half by like fifty.

0:22:33.040 --> 0:22:35.000
<v Speaker 1>Percent and that's one hundred and fifty grand.

0:22:35.040 --> 0:22:37.040
<v Speaker 2>Yeah, and I'm just I'm looking at it. I'm looking

0:22:37.080 --> 0:22:39.600
<v Speaker 2>at the like level two trading data, and there's there's

0:22:39.680 --> 0:22:44.320
<v Speaker 2>a big buy for like like one hundred thousand warrants

0:22:44.320 --> 0:22:46.680
<v Speaker 2>at a dollar or whatever, and then there's the floor

0:22:46.720 --> 0:22:49.800
<v Speaker 2>collapses under and I was like, huh, I'm just gonna like,

0:22:49.880 --> 0:22:51.919
<v Speaker 2>I'm just gonna sell to that entire bit and just

0:22:51.960 --> 0:22:53.920
<v Speaker 2>eat it, and like I'm getting out before like the

0:22:53.960 --> 0:22:56.200
<v Speaker 2>whole thing that's rug pulled, which was the right move

0:22:56.240 --> 0:23:00.399
<v Speaker 2>because I basically liquidated my position pre market from like

0:23:00.480 --> 0:23:02.760
<v Speaker 2>three hundred thousand dollars like one hundred and fifty or whatever.

0:23:02.760 --> 0:23:06.639
<v Speaker 2>And I was just like, man, that sucks, put in

0:23:06.640 --> 0:23:08.399
<v Speaker 2>the SMP, and then just went to the gym and

0:23:08.440 --> 0:23:12.040
<v Speaker 2>worked out for like real self loathing workout for three hours.

0:23:12.240 --> 0:23:15.320
<v Speaker 1>You know that that sort of big wackage is a

0:23:15.480 --> 0:23:18.959
<v Speaker 1>rite of passage of anybody that's ever worked on a

0:23:19.000 --> 0:23:21.399
<v Speaker 1>trading desk. I don't care if you're at you're at

0:23:21.480 --> 0:23:24.720
<v Speaker 1>Jane Street or if you're day trading from home. Those

0:23:24.880 --> 0:23:29.440
<v Speaker 1>losses are just so seminal and so instructive and focus

0:23:29.520 --> 0:23:32.840
<v Speaker 1>you on, Hey, what's my risk management. What's my edge here?

0:23:32.960 --> 0:23:35.959
<v Speaker 1>What am I really doing? Swing for the fences? Am

0:23:36.000 --> 0:23:38.280
<v Speaker 1>I really putting fifty or one hundred percent of my

0:23:38.359 --> 0:23:42.280
<v Speaker 1>portfolio into one trade? That seems kind of like you

0:23:42.280 --> 0:23:44.920
<v Speaker 1>you you could read that in a book, but until

0:23:44.960 --> 0:23:47.439
<v Speaker 1>you've lived it, it's really challenging.

0:23:47.480 --> 0:23:49.800
<v Speaker 2>The issue for me was like the plan I had

0:23:49.840 --> 0:23:53.160
<v Speaker 2>initially of like buy spacks near navs, sell when they pomp,

0:23:53.520 --> 0:23:56.119
<v Speaker 2>was like a good strategy. And if I'd stuck with that,

0:23:56.280 --> 0:23:58.200
<v Speaker 2>even if it stopped working, it's like, Okay.

0:23:58.440 --> 0:24:00.960
<v Speaker 1>The down side is the minimus, we made.

0:24:00.760 --> 0:24:02.840
<v Speaker 2>A bunch of money, this trade doesn't work, just like

0:24:02.920 --> 0:24:05.439
<v Speaker 2>parking index fund until any right, yeah, and then like

0:24:05.480 --> 0:24:07.720
<v Speaker 2>either come up with something new or just stop. The

0:24:07.800 --> 0:24:09.880
<v Speaker 2>issue was I was so used to number going up.

0:24:10.280 --> 0:24:11.880
<v Speaker 2>I was kind of willing to bet the house I'm

0:24:11.920 --> 0:24:14.679
<v Speaker 2>doing it one more time, then I'm confident I hit

0:24:14.680 --> 0:24:16.280
<v Speaker 2>a million. I would have walked away like that was

0:24:16.320 --> 0:24:17.399
<v Speaker 2>just like a benchmark numbers.

0:24:17.480 --> 0:24:20.520
<v Speaker 1>Oh you should know that when you hit, you would

0:24:20.600 --> 0:24:24.000
<v Speaker 1>not have whiked away. Junkies don't say one more hit,

0:24:24.119 --> 0:24:27.320
<v Speaker 1>and gamblers don't say, I just need this parlay to

0:24:27.320 --> 0:24:30.600
<v Speaker 1>come in and then I'm good because you're always looking

0:24:30.640 --> 0:24:33.359
<v Speaker 1>for the for the dopamine, hit for the adrenaline.

0:24:33.359 --> 0:24:35.919
<v Speaker 2>I would have found something else to speculate on. But

0:24:35.960 --> 0:24:38.560
<v Speaker 2>I think I would have stopped trading SPACs had that happened.

0:24:38.800 --> 0:24:42.400
<v Speaker 1>Coming up, we continue our conversation with Jack Rains, discussing

0:24:43.200 --> 0:24:47.879
<v Speaker 1>Slow Ventures and investing in creators. I'm Barry rid Halts.

0:24:47.880 --> 0:24:52.680
<v Speaker 1>You're listening to Masters in Business on Bloomberg Radio. I'm

0:24:52.680 --> 0:24:57.280
<v Speaker 1>Barry Ridults. You're listening to Masters in Business on Bloomberg Radio.

0:24:57.680 --> 0:25:00.720
<v Speaker 1>My uh, somewhat special guests. Is that how you want

0:25:00.760 --> 0:25:02.760
<v Speaker 1>to be? Is that how you described it? Said?

0:25:02.840 --> 0:25:03.679
<v Speaker 2>Marginally special?

0:25:03.760 --> 0:25:07.760
<v Speaker 1>My marginally special guest, Jack Rains is here. He is

0:25:08.480 --> 0:25:12.280
<v Speaker 1>an associate at the venture capital firm Slow Ventures and

0:25:12.320 --> 0:25:15.120
<v Speaker 1>the author of the book Young Money, which we'll get

0:25:15.119 --> 0:25:18.280
<v Speaker 1>to in a few minutes. So I'm kind of fascinated

0:25:18.320 --> 0:25:23.080
<v Speaker 1>how you pivoted into VC work. You joined Slow Ventures

0:25:23.080 --> 0:25:27.480
<v Speaker 1>in San Francisco from New York. Did you relocate to

0:25:27.520 --> 0:25:30.639
<v Speaker 1>San Francisco and then come back to New York? So

0:25:30.720 --> 0:25:32.760
<v Speaker 1>I kind of get this venture by coastal.

0:25:33.480 --> 0:25:36.240
<v Speaker 2>I try to. I try to. I try to make

0:25:36.240 --> 0:25:38.679
<v Speaker 2>it look by coastal occasionally on Twitter. No, I mean

0:25:38.720 --> 0:25:40.720
<v Speaker 2>The funny thing was they were hiring in New York

0:25:40.760 --> 0:25:43.160
<v Speaker 2>and San Francisco, and I applied for the New York job,

0:25:43.440 --> 0:25:46.399
<v Speaker 2>and met was the partner in New York first, and

0:25:46.440 --> 0:25:50.280
<v Speaker 2>then the one of the gps in San Francisco, Sam Lesson.

0:25:50.440 --> 0:25:52.040
<v Speaker 2>I get introduced to him by the guy in New

0:25:52.119 --> 0:25:54.720
<v Speaker 2>York and we're on a zoom call. He'd like, just

0:25:54.720 --> 0:25:57.399
<v Speaker 2>come from the gym, super sweaty and like shoveled looking,

0:25:57.520 --> 0:25:59.480
<v Speaker 2>and five minutes you all to say that.

0:26:00.040 --> 0:26:00.720
<v Speaker 1>I'm okay with that.

0:26:00.760 --> 0:26:03.160
<v Speaker 2>I think he would agree with it. Five minutes, five

0:26:03.160 --> 0:26:04.280
<v Speaker 2>minutes out of the call, he's like, what do you

0:26:04.320 --> 0:26:07.399
<v Speaker 2>think of San Francisco? And I said fentannel and homeless people,

0:26:07.800 --> 0:26:10.760
<v Speaker 2>and he was like, it's a crazy ass for somebody

0:26:10.800 --> 0:26:12.560
<v Speaker 2>applying to a job in San Francisco. And I was

0:26:12.600 --> 0:26:16.040
<v Speaker 2>just like, I didn't like I applied for the job

0:26:16.080 --> 0:26:18.880
<v Speaker 2>in New York and he was just kind of like, well,

0:26:19.119 --> 0:26:21.000
<v Speaker 2>I thought I was interviewing you for an SF seat,

0:26:21.040 --> 0:26:23.240
<v Speaker 2>and I was just like he told me to like

0:26:23.280 --> 0:26:25.040
<v Speaker 2>take a beat and like think about it. And I

0:26:25.600 --> 0:26:27.080
<v Speaker 2>can't rememer if I told him on the collar. Just

0:26:27.080 --> 0:26:29.600
<v Speaker 2>texted him right after, but I was like honestly, dude,

0:26:29.600 --> 0:26:31.280
<v Speaker 2>I mean, I want the job, so I didn't know

0:26:31.320 --> 0:26:33.600
<v Speaker 2>this is what I was applying for. But if you

0:26:33.680 --> 0:26:35.639
<v Speaker 2>hire me, I'll move to San Francisco. And he was like,

0:26:35.640 --> 0:26:38.280
<v Speaker 2>have you ever visited? And I said no, so.

0:26:38.359 --> 0:26:41.000
<v Speaker 1>But I've been to twenty five other countries in fifty

0:26:41.040 --> 0:26:43.120
<v Speaker 1>other cities. I'm sure I can figure it out.

0:26:43.240 --> 0:26:46.000
<v Speaker 2>Yeah. The only difference to San Francisco has so many

0:26:46.040 --> 0:26:49.440
<v Speaker 2>more AI startup advertisements on the billboards and the way mos,

0:26:49.480 --> 0:26:52.600
<v Speaker 2>which are awesome. But yeah, like I I mean I.

0:26:52.920 --> 0:26:55.399
<v Speaker 1>And they are everywhere. We were just San Francisco a

0:26:55.400 --> 0:26:55.920
<v Speaker 1>few months ago.

0:26:56.000 --> 0:26:56.720
<v Speaker 2>They're so sick.

0:26:57.280 --> 0:26:59.480
<v Speaker 1>They they're like yellow cabs in New York.

0:26:59.800 --> 0:27:01.919
<v Speaker 2>Yeah, yeah, they're They're incredible. I mean the worst thing

0:27:01.920 --> 0:27:03.480
<v Speaker 2>about New York is that we keep trying to like

0:27:03.520 --> 0:27:06.480
<v Speaker 2>block way Moos. Let it happen. I'm I'm so pro Weemo.

0:27:06.560 --> 0:27:09.960
<v Speaker 2>I'm like Waymo's biggest fanboy. But yeah, like, going back

0:27:10.000 --> 0:27:13.840
<v Speaker 2>to Fall twenty twenty four, I was in this real

0:27:13.960 --> 0:27:15.880
<v Speaker 2>like kind of career panic. I want to get out

0:27:15.880 --> 0:27:17.720
<v Speaker 2>of media, and like I was like I should have

0:27:17.760 --> 0:27:20.200
<v Speaker 2>gone down the investing route, and then you know it's

0:27:20.200 --> 0:27:22.080
<v Speaker 2>like a step back and I had like signed that

0:27:22.080 --> 0:27:24.119
<v Speaker 2>book deal. I was like, Okay, I'm gonna have to

0:27:24.119 --> 0:27:25.359
<v Speaker 2>write a book. I'm gonna have to be able to

0:27:25.359 --> 0:27:27.240
<v Speaker 2>market it. So that means I need to look at

0:27:27.320 --> 0:27:30.240
<v Speaker 2>jobs where I could still have like bandwidth and flexibility

0:27:30.240 --> 0:27:33.360
<v Speaker 2>to do so, which like eliminates a lot of investing

0:27:33.400 --> 0:27:35.560
<v Speaker 2>ease stuff where there's compliance issues.

0:27:35.280 --> 0:27:39.280
<v Speaker 1>No investment banking, no no trading on a desk, and

0:27:39.320 --> 0:27:44.919
<v Speaker 1>no portfolio management or even CFA analysts where whatever you

0:27:45.000 --> 0:27:50.600
<v Speaker 1>do is disclosable and requires approval and it's complex.

0:27:50.920 --> 0:27:54.640
<v Speaker 2>But venture capital is like the biggest, like build your

0:27:54.640 --> 0:27:57.480
<v Speaker 2>personal brand, like content helps you source deals. So I

0:27:57.560 --> 0:27:59.000
<v Speaker 2>kind of honed in on and I didn't have like

0:27:59.000 --> 0:28:01.440
<v Speaker 2>an investment banking back ground. VC is more open to

0:28:01.720 --> 0:28:04.879
<v Speaker 2>non traditional investing backgrounds. It just kind of made sense.

0:28:05.000 --> 0:28:06.960
<v Speaker 2>And I had a decent network in that space from

0:28:06.960 --> 0:28:09.119
<v Speaker 2>like Twitter and riding and all this stuff. So I

0:28:09.160 --> 0:28:11.160
<v Speaker 2>just kind of started pounding the pavement, like reaching out

0:28:11.160 --> 0:28:12.720
<v Speaker 2>to vcs. I knew of my network that may or

0:28:12.760 --> 0:28:16.359
<v Speaker 2>may not be hiring, and Slow happened to be hiring,

0:28:16.400 --> 0:28:19.159
<v Speaker 2>and I messaged hilariously. I messaged Yoni, the partner of

0:28:19.200 --> 0:28:21.119
<v Speaker 2>New York on Blue Sky, that was back when everybody

0:28:21.119 --> 0:28:22.680
<v Speaker 2>I thought Twitter was going to die and blue Sky

0:28:22.760 --> 0:28:24.480
<v Speaker 2>was Blue.

0:28:24.240 --> 0:28:26.359
<v Speaker 1>Sky didn't take off. But it does feel like Twitter

0:28:26.440 --> 0:28:29.440
<v Speaker 1>is kind of ground to a shell.

0:28:29.240 --> 0:28:31.240
<v Speaker 2>Of what it. I think it's starting to come back

0:28:31.320 --> 0:28:33.280
<v Speaker 2>as of like a month ago. Oh really, it feels

0:28:33.280 --> 0:28:35.280
<v Speaker 2>like they changed the algorithm where you can like see

0:28:35.320 --> 0:28:40.400
<v Speaker 2>your mutuals again, so people literally last week Nikita Beer tweeted,

0:28:40.440 --> 0:28:43.240
<v Speaker 2>they tweet the algo so like you're seeing your mutual

0:28:43.280 --> 0:28:44.920
<v Speaker 2>followers and I was like, dude, that's what it should

0:28:44.920 --> 0:28:48.239
<v Speaker 2>have been the whole time. But anyway, I basically got

0:28:48.280 --> 0:28:50.880
<v Speaker 2>hired from a Twitter DM and then a last second

0:28:50.880 --> 0:28:53.560
<v Speaker 2>flight to San Francisco six weeks.

0:28:53.320 --> 0:28:56.600
<v Speaker 1>From application to starting in SF.

0:28:56.880 --> 0:29:00.960
<v Speaker 2>Basically like I didn't know where to live. Facebook Marketplace,

0:29:01.080 --> 0:29:02.920
<v Speaker 2>found some dude with an open room and just hopped

0:29:02.920 --> 0:29:05.320
<v Speaker 2>on a FaceTime with him, and I was just like, yeah, like,

0:29:05.360 --> 0:29:07.920
<v Speaker 2>I guess I'll just take the other half of your apartment.

0:29:08.560 --> 0:29:10.120
<v Speaker 2>And then I moved there. That was I just put

0:29:10.160 --> 0:29:12.000
<v Speaker 2>my stuff in a in a suitcase and just flew out.

0:29:12.440 --> 0:29:13.720
<v Speaker 1>So are you New York based?

0:29:13.960 --> 0:29:15.480
<v Speaker 2>I live in New York now. I moved back here

0:29:15.520 --> 0:29:16.480
<v Speaker 2>a few months ago, all.

0:29:16.480 --> 0:29:18.760
<v Speaker 1>Right, And and how do you how do you work

0:29:18.840 --> 0:29:21.959
<v Speaker 1>that out if your core office is San Francisco.

0:29:22.200 --> 0:29:25.360
<v Speaker 2>So we have an office in New York too, Flat Iron,

0:29:25.520 --> 0:29:28.240
<v Speaker 2>so twentieth and fifth. It was one of those things

0:29:28.280 --> 0:29:30.760
<v Speaker 2>where we were pretty a sync in San Francisco, like

0:29:30.800 --> 0:29:34.200
<v Speaker 2>we have an office in downtown SF. I was going

0:29:34.240 --> 0:29:36.640
<v Speaker 2>in probably four days a week, so like some people

0:29:36.680 --> 0:29:38.600
<v Speaker 2>were going in a lot. My boss lived in the

0:29:38.640 --> 0:29:40.600
<v Speaker 2>suburbs a little bit. He would come up sometimes, but

0:29:40.640 --> 0:29:43.720
<v Speaker 2>I would like take the cowtrain down to like the

0:29:43.760 --> 0:29:45.840
<v Speaker 2>Hillsbo area and like go to his place. So I

0:29:45.880 --> 0:29:48.240
<v Speaker 2>work from his poolhouse with him. It was a funny setup,

0:29:49.160 --> 0:29:51.400
<v Speaker 2>but it was like we were a sync enough. And

0:29:51.440 --> 0:29:53.360
<v Speaker 2>I also knew that like long term, I was gonna

0:29:53.360 --> 0:29:55.360
<v Speaker 2>want to live in New York. I just pitched them

0:29:55.400 --> 0:29:57.840
<v Speaker 2>on moving back and then flying out to San Francisco

0:29:58.200 --> 0:30:00.240
<v Speaker 2>like every three weeks or so, and that it's the

0:30:00.320 --> 0:30:01.160
<v Speaker 2>setup I have now.

0:30:01.120 --> 0:30:05.000
<v Speaker 1>That New York has a pretty robust technology sets there.

0:30:06.000 --> 0:30:10.280
<v Speaker 1>I mean, we all think of San Francisco for AI

0:30:10.520 --> 0:30:15.080
<v Speaker 1>computer mobile tech and Boston for healthcare teche. Where does

0:30:15.120 --> 0:30:17.000
<v Speaker 1>New York land in that in that list?

0:30:17.240 --> 0:30:19.160
<v Speaker 2>It's it's increasing I would I would put in New

0:30:19.240 --> 0:30:19.920
<v Speaker 2>York is the.

0:30:20.040 --> 0:30:22.920
<v Speaker 1>Like pretty fast rising right on for.

0:30:22.920 --> 0:30:25.520
<v Speaker 2>Like consumer tech. I would argue it's like number one

0:30:25.600 --> 0:30:26.280
<v Speaker 2>or close to it.

0:30:26.360 --> 0:30:28.520
<v Speaker 1>And then you've got a big Google office here, You've

0:30:28.520 --> 0:30:30.600
<v Speaker 1>got a big Microsoft office here. You've got a giant

0:30:30.640 --> 0:30:31.640
<v Speaker 1>Amazon office here.

0:30:31.720 --> 0:30:34.800
<v Speaker 2>Well, and like Anthropics opening like a sixteen thousand square

0:30:34.800 --> 0:30:38.040
<v Speaker 2>foot like they're opening a massive office in Hudson Square.

0:30:38.160 --> 0:30:39.680
<v Speaker 1>Like you there's some space there.

0:30:39.720 --> 0:30:42.360
<v Speaker 2>A lot of like a lot of a lot of

0:30:42.360 --> 0:30:44.840
<v Speaker 2>what keeps happening is like all these AI companies start

0:30:44.880 --> 0:30:46.880
<v Speaker 2>there and then as they move into like bigger and bigger,

0:30:46.920 --> 0:30:49.960
<v Speaker 2>like enterprise commercial business, they expand to the East coast,

0:30:50.080 --> 0:30:51.880
<v Speaker 2>and like there's a lot of like sales teams on

0:30:51.920 --> 0:30:54.080
<v Speaker 2>the East coast and engineering town on the west coast.

0:30:54.640 --> 0:30:57.120
<v Speaker 2>New York's also like a more social, outgoing city where

0:30:57.120 --> 0:30:59.239
<v Speaker 2>a lot of the like like sales and go to

0:30:59.240 --> 0:31:02.160
<v Speaker 2>market people would prefer to live here. San Francisco is

0:31:02.160 --> 0:31:05.440
<v Speaker 2>more insular, and it's like, uh, there's just engineering talent

0:31:05.480 --> 0:31:09.320
<v Speaker 2>from like Stanford, Berkeley, whatever. It aggregates around the Bay.

0:31:09.360 --> 0:31:12.080
<v Speaker 2>So it's it's honestly a big part of like engineers

0:31:12.120 --> 0:31:13.480
<v Speaker 2>end up on the West coast, and then a lot

0:31:13.480 --> 0:31:15.120
<v Speaker 2>of the sales people end up on the East coast.

0:31:15.600 --> 0:31:17.760
<v Speaker 2>A lot of the customers are also on the East coast.

0:31:17.680 --> 0:31:21.120
<v Speaker 1>So really interesting. All right, So I got to start

0:31:21.160 --> 0:31:25.360
<v Speaker 1>with a few quotes of yours and we'll plow through

0:31:25.400 --> 0:31:29.280
<v Speaker 1>a lot of that. One of the things though, that

0:31:29.640 --> 0:31:33.360
<v Speaker 1>that you said a quote of yours, junior investing jobs

0:31:33.400 --> 0:31:37.360
<v Speaker 1>at VC megafunds are really just cold calling. Yeah, I

0:31:37.880 --> 0:31:41.280
<v Speaker 1>don't think of VC in those terms. Explain are you

0:31:41.360 --> 0:31:43.280
<v Speaker 1>really just smiling and dialing.

0:31:43.440 --> 0:31:45.520
<v Speaker 2>Like a little bit. It's funny, Like I don't know

0:31:45.520 --> 0:31:47.800
<v Speaker 2>if you read Bill Gurley's new book, Run It Out

0:31:47.800 --> 0:31:49.960
<v Speaker 2>of Dream, so he said something similar with a venture

0:31:49.960 --> 0:31:52.200
<v Speaker 2>capital is ninety percent sales, and it really is.

0:31:52.160 --> 0:31:54.840
<v Speaker 1>Like, but that's true about everything in fine Yeah, it's

0:31:54.880 --> 0:31:58.240
<v Speaker 1>really and I don't know about outside, but everything in

0:31:58.280 --> 0:32:02.560
<v Speaker 1>this space is you're ultimately asking someone to trust you

0:32:02.600 --> 0:32:03.680
<v Speaker 1>and give you their business.

0:32:03.760 --> 0:32:07.520
<v Speaker 2>Yep, yep, yep. VC, especially at the big like it's

0:32:07.600 --> 0:32:10.120
<v Speaker 2>like Slow is a fairly small fund, right, Like we

0:32:10.200 --> 0:32:13.640
<v Speaker 2>have like total teams like fifteen or sixteen people, investment

0:32:13.680 --> 0:32:16.720
<v Speaker 2>teams like nine or ten people. But like some of

0:32:16.720 --> 0:32:18.680
<v Speaker 2>the bigger funds, like I have some bodies that have

0:32:18.760 --> 0:32:21.360
<v Speaker 2>worked at the like call it some combination of like

0:32:21.480 --> 0:32:25.120
<v Speaker 2>the general catalyst type A sixteen Z type whatever. It's

0:32:25.160 --> 0:32:27.920
<v Speaker 2>just a machine or like inside is like this too,

0:32:28.080 --> 0:32:31.760
<v Speaker 2>or like you are managing just like tens of billions

0:32:31.800 --> 0:32:34.600
<v Speaker 2>of dollars or whatever, and there's so much coverage that

0:32:34.680 --> 0:32:37.920
<v Speaker 2>it's I was a little tongue in cheek saying that

0:32:37.960 --> 0:32:39.800
<v Speaker 2>it's like cold calling, but it is very much like

0:32:40.120 --> 0:32:42.560
<v Speaker 2>you need to be talking to like X number of people,

0:32:42.560 --> 0:32:45.440
<v Speaker 2>and there's like metric hurdles on like touch points and stuff.

0:32:45.680 --> 0:32:49.920
<v Speaker 2>It's like it's not that there's no discernment or anything

0:32:49.960 --> 0:32:51.400
<v Speaker 2>like that, but it's a volume game and.

0:32:51.800 --> 0:32:56.080
<v Speaker 1>They try and quantify it and turn it into.

0:32:55.880 --> 0:32:58.040
<v Speaker 2>Yeah, it's like you the name of the game is

0:32:58.040 --> 0:33:01.360
<v Speaker 2>you don't want to miss anything that could be something. Therefore,

0:33:01.400 --> 0:33:04.000
<v Speaker 2>like people should be pounding the pavement making touch points

0:33:04.040 --> 0:33:06.719
<v Speaker 2>with anybody who could be starting an early stage tech company.

0:33:06.800 --> 0:33:11.800
<v Speaker 1>Now, Slow Ventures kind of famously avoids the trendy hot stuff.

0:33:12.720 --> 0:33:17.160
<v Speaker 1>No robots, no AI foundation models, What are you looking

0:33:17.200 --> 0:33:20.719
<v Speaker 1>at at work? That's kind of interesting. What do you

0:33:20.760 --> 0:33:23.000
<v Speaker 1>guys get to see that most people are overlooking?

0:33:23.400 --> 0:33:26.360
<v Speaker 2>So it's funny. We actually we actually just announced one

0:33:26.400 --> 0:33:30.640
<v Speaker 2>that's like robot e doing like like warehouses and fulfillment

0:33:30.720 --> 0:33:33.719
<v Speaker 2>for e commerce companies called Sutronic, So we do occasionally

0:33:33.760 --> 0:33:38.240
<v Speaker 2>touch they don't make You'm right right, We're not doing

0:33:38.240 --> 0:33:40.040
<v Speaker 2>any of the stuff that it's cloud on Twitter because

0:33:40.080 --> 0:33:44.120
<v Speaker 2>we can't fold, close or do dishes, right. I mean

0:33:44.160 --> 0:33:47.640
<v Speaker 2>it's we're like broadly generalists. We've done everything from like

0:33:48.120 --> 0:33:50.880
<v Speaker 2>we've done just to name some companies over the last

0:33:50.880 --> 0:33:55.880
<v Speaker 2>ten or twelve years, like Robinhood, Slack, all Birds before

0:33:55.880 --> 0:33:58.520
<v Speaker 2>they pivoted to being an AI GPU company back when

0:33:58.520 --> 0:34:02.280
<v Speaker 2>they sold footwear. I mean, we have like a hilarious

0:34:02.280 --> 0:34:05.640
<v Speaker 2>one meme, Lord's Technology where it's basically a software platform.

0:34:05.800 --> 0:34:09.240
<v Speaker 2>It's like a basically marketing tool platform, but for creating memes.

0:34:10.239 --> 0:34:12.080
<v Speaker 2>I mean, we'll do a little bit of everything we've done.

0:34:12.080 --> 0:34:14.720
<v Speaker 2>Crypto stuff we've done. We have done some like vertical

0:34:14.760 --> 0:34:17.359
<v Speaker 2>AI stuff. We just like making our calling card. We're

0:34:17.360 --> 0:34:20.200
<v Speaker 2>not chasing the AI hype. The way that we broadly

0:34:20.239 --> 0:34:23.960
<v Speaker 2>think about it is there's a lot of VC deals

0:34:24.000 --> 0:34:26.920
<v Speaker 2>that are trades that are now marked up a lot,

0:34:27.000 --> 0:34:29.520
<v Speaker 2>but like do they have terminal value in what they

0:34:29.520 --> 0:34:32.680
<v Speaker 2>get supported in public markets? You don't know? And a

0:34:32.680 --> 0:34:34.640
<v Speaker 2>lot of early stage investors that have played those and

0:34:34.719 --> 0:34:37.399
<v Speaker 2>then sold when bigger funds come in at the multi

0:34:37.400 --> 0:34:39.319
<v Speaker 2>billion dollar evaluations. It made a lot of money. So

0:34:39.360 --> 0:34:42.120
<v Speaker 2>like you could argue we should have played that trading game.

0:34:42.280 --> 0:34:45.040
<v Speaker 2>The bet that we're making is like, go for the

0:34:45.080 --> 0:34:47.279
<v Speaker 2>stuff that's going to compound long term value, that could

0:34:47.320 --> 0:34:49.280
<v Speaker 2>be like a standalone valuable entity.

0:34:50.200 --> 0:34:54.920
<v Speaker 1>How does the sort of dearth of IPOs, although we're

0:34:54.920 --> 0:34:57.200
<v Speaker 1>in the middle of a period where there are suddenly

0:34:57.200 --> 0:35:00.720
<v Speaker 1>a spate of them coming out and more more companies

0:35:00.800 --> 0:35:04.960
<v Speaker 1>choosing to stay private for longer, how does that figure

0:35:05.000 --> 0:35:08.680
<v Speaker 1>into the VC calculus of Hey, we eventually want an

0:35:08.719 --> 0:35:11.959
<v Speaker 1>exit and we can't rely on someone else, either from

0:35:11.960 --> 0:35:15.160
<v Speaker 1>a big affirm taking this over or some M and

0:35:15.200 --> 0:35:16.480
<v Speaker 1>A to give us an exit.

0:35:16.680 --> 0:35:18.879
<v Speaker 2>It's interesting. I almost think you have to put VC

0:35:19.000 --> 0:35:20.960
<v Speaker 2>in two buckets at this point, where you have like

0:35:21.120 --> 0:35:23.319
<v Speaker 2>we play at the really early stage, which also gives

0:35:23.400 --> 0:35:26.759
<v Speaker 2>you like a lot more opportunities for exits, whether you

0:35:26.920 --> 0:35:29.799
<v Speaker 2>sell steakes to like a later stage bigger growth like

0:35:29.840 --> 0:35:32.880
<v Speaker 2>a bigger growth investor once they're in the unicorn status,

0:35:33.160 --> 0:35:35.560
<v Speaker 2>or you get the acquisition or IPO if you're getting

0:35:35.600 --> 0:35:37.760
<v Speaker 2>at a company that's worth twenty or thirty million dollars.

0:35:38.280 --> 0:35:39.879
<v Speaker 2>There's just like a lot of ways you can get

0:35:39.880 --> 0:35:42.960
<v Speaker 2>paid on that. Versus you have companies like like Thrive

0:35:43.040 --> 0:35:44.840
<v Speaker 2>is probably the most famous one where they manage like

0:35:44.880 --> 0:35:47.680
<v Speaker 2>fifty billion dollars now they own a massive slug of

0:35:47.719 --> 0:35:51.800
<v Speaker 2>open ai, Like they take really big bets in companies

0:35:51.840 --> 0:35:54.720
<v Speaker 2>that are like it's worth ten billion or one hundred billion,

0:35:54.800 --> 0:35:56.400
<v Speaker 2>we think it can be worth a hundred billion or

0:35:56.400 --> 0:35:59.360
<v Speaker 2>a trillion. So for us, we have a lot more

0:35:59.440 --> 0:36:02.040
<v Speaker 2>flexibility on exits, which is like good because we can

0:36:02.080 --> 0:36:02.640
<v Speaker 2>be more nimble.

0:36:02.800 --> 0:36:05.840
<v Speaker 1>You're primarily seed in A rounds, but you're not doing

0:36:06.000 --> 0:36:06.799
<v Speaker 1>B rounds, or.

0:36:07.160 --> 0:36:09.920
<v Speaker 2>We occasionally will with follow on capital, but it's like

0:36:10.000 --> 0:36:12.560
<v Speaker 2>ninety five percent seed in A So that's like that's

0:36:12.600 --> 0:36:15.240
<v Speaker 2>our sweet spot. And then so I think for funds

0:36:15.280 --> 0:36:19.239
<v Speaker 2>like that, I think people like a lot of early

0:36:19.239 --> 0:36:22.200
<v Speaker 2>stage funds should get more creative. Where can you exit

0:36:22.280 --> 0:36:24.319
<v Speaker 2>into a big growth fund coming in at like a

0:36:24.360 --> 0:36:28.239
<v Speaker 2>five billion dollar valuation from portfolio construction? Maybe you should

0:36:28.480 --> 0:36:31.040
<v Speaker 2>With the megafunds, it's like, okay, if you're going to

0:36:31.120 --> 0:36:34.120
<v Speaker 2>do that, you can't really index all of the like

0:36:34.239 --> 0:36:36.520
<v Speaker 2>five or ten billion dollar unicorns because a lot of

0:36:36.560 --> 0:36:38.920
<v Speaker 2>those those paper marks would never get support in the

0:36:38.960 --> 0:36:44.280
<v Speaker 2>public markets. But like Thrive going really deep on open

0:36:44.320 --> 0:36:48.560
<v Speaker 2>Ai or Spark Capital going really deep on Anthropic, those

0:36:48.600 --> 0:36:51.160
<v Speaker 2>are going to go out at potentially trillion dollar valuations.

0:36:51.239 --> 0:36:55.480
<v Speaker 2>Like the math works. If you invest forty billion dollars

0:36:55.560 --> 0:36:57.960
<v Speaker 2>across a few big funds and something at like a

0:36:57.960 --> 0:37:00.560
<v Speaker 2>two hundred billion dollars valuation and you get four x

0:37:00.640 --> 0:37:04.080
<v Speaker 2>or five x, you're returning like tens of billions of dollars. Right,

0:37:04.320 --> 0:37:07.640
<v Speaker 2>So it's like in the early stage should probably be

0:37:07.760 --> 0:37:10.040
<v Speaker 2>looking to sell, and some some of those later stage

0:37:10.080 --> 0:37:13.680
<v Speaker 2>companies coming in at the later stage, it's like stock picking.

0:37:13.719 --> 0:37:15.759
<v Speaker 2>You're basically running. You have to run a concentrated book

0:37:15.800 --> 0:37:17.920
<v Speaker 2>of like there might be three or four private companies

0:37:17.960 --> 0:37:20.640
<v Speaker 2>at any time, like a SpaceX, Open Ai and Thropic

0:37:20.960 --> 0:37:23.720
<v Speaker 2>that could go out at a multi hundred billion dollar valuation.

0:37:24.719 --> 0:37:27.399
<v Speaker 2>You have to be concentrated in those otherwise the math

0:37:27.480 --> 0:37:29.319
<v Speaker 2>is going to work. If you get those right, you

0:37:29.320 --> 0:37:31.160
<v Speaker 2>can like two x three x a fund. If you don't,

0:37:31.200 --> 0:37:31.880
<v Speaker 2>you want.

0:37:32.840 --> 0:37:36.880
<v Speaker 1>Really kind of interesting you come out of the creator economy.

0:37:37.080 --> 0:37:42.400
<v Speaker 1>Slow Ventures has been a player in that space. How

0:37:42.440 --> 0:37:46.400
<v Speaker 1>does how does your experience help you as a VC

0:37:47.160 --> 0:37:50.040
<v Speaker 1>and what does slow venture see in that space that

0:37:50.400 --> 0:37:53.120
<v Speaker 1>you know the traditional venture capitalists overlook.

0:37:53.280 --> 0:37:54.960
<v Speaker 2>So to give like a little more color on that

0:37:55.000 --> 0:37:57.040
<v Speaker 2>we have we have a separate fund we raised a

0:37:57.080 --> 0:38:00.880
<v Speaker 2>year ago called our Creator Fund, where sixty four million

0:38:00.880 --> 0:38:05.600
<v Speaker 2>dollars we invest directly in creators, meaning like YouTubers, podcasters,

0:38:05.760 --> 0:38:09.080
<v Speaker 2>could be newsletter writers. Our bet on that is that

0:38:09.200 --> 0:38:14.719
<v Speaker 2>like distribution compared to like technical abilities is getting increasingly valuable.

0:38:14.760 --> 0:38:17.799
<v Speaker 2>Where two things One, it's easier to build stuff like

0:38:17.880 --> 0:38:21.200
<v Speaker 2>software because of AI coding assistance. Too, the Internet is

0:38:21.200 --> 0:38:24.040
<v Speaker 2>so loud now that having like a cylinder of trust

0:38:24.160 --> 0:38:27.279
<v Speaker 2>from your audience gives you a massive selling advantage because

0:38:27.280 --> 0:38:29.560
<v Speaker 2>it's so much harder to get attention with like paid

0:38:29.560 --> 0:38:33.200
<v Speaker 2>ads and growth hacks and all this. That we have

0:38:33.280 --> 0:38:35.680
<v Speaker 2>this and like sam My Boss was kind of came

0:38:35.760 --> 0:38:37.480
<v Speaker 2>up with this idea a few years ago that like

0:38:37.560 --> 0:38:40.560
<v Speaker 2>he calls it almost investing in cults. But people who

0:38:40.600 --> 0:38:42.799
<v Speaker 2>have a true like cult of personality and are a

0:38:42.920 --> 0:38:46.680
<v Speaker 2>subject matter expert in a particular theme or vertical have

0:38:46.800 --> 0:38:50.560
<v Speaker 2>a massive advantage on like marketing and selling. So we

0:38:50.680 --> 0:38:54.200
<v Speaker 2>raised a fund where we literally invest in creators like

0:38:54.239 --> 0:38:58.160
<v Speaker 2>holding companies where any businesses they build like off their platform,

0:38:58.200 --> 0:39:00.760
<v Speaker 2>that leverage their brand and platform and all this stuff.

0:39:00.760 --> 0:39:03.640
<v Speaker 1>These are three sixty deals covers everything that person does.

0:39:03.760 --> 0:39:03.960
<v Speaker 2>Yeah.

0:39:04.120 --> 0:39:06.759
<v Speaker 1>Yeah, we basically be a podcast, could be substack, could

0:39:06.800 --> 0:39:07.520
<v Speaker 1>be all of those.

0:39:07.680 --> 0:39:09.640
<v Speaker 2>Yeah, and like we aren't really that interested in like

0:39:09.719 --> 0:39:12.040
<v Speaker 2>how money they make from like ad revenue or like

0:39:12.080 --> 0:39:15.279
<v Speaker 2>platform revenue or whatever. It's more so. For example, the

0:39:15.280 --> 0:39:18.120
<v Speaker 2>first deal we did was with this woodworking creator named

0:39:18.200 --> 0:39:21.239
<v Speaker 2>Jonathan Katz Moses, and he has a like he has

0:39:21.280 --> 0:39:22.239
<v Speaker 2>a massive YouTube channel.

0:39:22.280 --> 0:39:25.919
<v Speaker 1>He's basically I know that just show it is shockingly

0:39:26.440 --> 0:39:30.799
<v Speaker 1>intriguing watching this guy build stuff from scratch. Yeah, he's

0:39:30.840 --> 0:39:31.919
<v Speaker 1>like relaxing too.

0:39:32.080 --> 0:39:36.160
<v Speaker 2>Yeah, he's a super compelling guy, incredibly talented, and he's

0:39:36.280 --> 0:39:39.200
<v Speaker 2>equally good as both a content creator and as an entrepreneur.

0:39:39.239 --> 0:39:41.480
<v Speaker 2>Like he has a business it's like making like millions

0:39:41.520 --> 0:39:42.839
<v Speaker 2>of dollars in revenue, and.

0:39:43.160 --> 0:39:47.000
<v Speaker 1>He builds various things and sells them, so he also

0:39:47.080 --> 0:39:49.280
<v Speaker 1>generates revenue from the YouTube.

0:39:49.040 --> 0:39:51.439
<v Speaker 2>Right, And it's like a specifically has like a tool

0:39:51.480 --> 0:39:55.040
<v Speaker 2>line called km Tools, and like we invested money into

0:39:55.040 --> 0:39:57.400
<v Speaker 2>like his holding company, and that can go toward like

0:39:57.680 --> 0:40:01.000
<v Speaker 2>hiring people to help with like the content development, editing,

0:40:01.040 --> 0:40:04.040
<v Speaker 2>content creation, so we can like increase velocity of putting

0:40:04.080 --> 0:40:07.120
<v Speaker 2>out YouTube videos. Also like more people to help rolling

0:40:07.120 --> 0:40:09.560
<v Speaker 2>out new products and a wider product suite of tools.

0:40:09.920 --> 0:40:12.160
<v Speaker 2>So the bet is that like you put money in

0:40:12.200 --> 0:40:14.799
<v Speaker 2>that and maybe like the tool business really blows up

0:40:14.880 --> 0:40:17.360
<v Speaker 2>and then a like Black and Decker type of company

0:40:17.360 --> 0:40:20.800
<v Speaker 2>acquires it, or maybe he launches like another business vertical

0:40:20.840 --> 0:40:23.600
<v Speaker 2>office platform that we have exposure to. So it's but

0:40:23.680 --> 0:40:26.719
<v Speaker 2>his whole thing is like woodworking, woodworkers. He'll go to

0:40:26.719 --> 0:40:29.200
<v Speaker 2>like a woodworking festival in Texas, people will come out,

0:40:29.239 --> 0:40:32.000
<v Speaker 2>like to come like get him to like sign their autographs.

0:40:32.040 --> 0:40:34.040
<v Speaker 2>Like he he just has a lot of clout in

0:40:34.040 --> 0:40:38.120
<v Speaker 2>that space. So finding people like that in different verticals

0:40:38.200 --> 0:40:41.760
<v Speaker 2>that we think have like really compelling opportunities to scale

0:40:41.800 --> 0:40:45.880
<v Speaker 2>big businesses through that vertical in that audience is like interesting.

0:40:46.080 --> 0:40:49.839
<v Speaker 2>And historically people have been very hesitant to back creators

0:40:50.040 --> 0:40:52.759
<v Speaker 2>or they back like one business like mister Beast has

0:40:52.760 --> 0:40:55.480
<v Speaker 2>a bunch of different businesses. If you back Beast Burgers

0:40:55.960 --> 0:40:58.520
<v Speaker 2>didn't really work that well. If you were backing mister

0:40:58.560 --> 0:41:01.080
<v Speaker 2>Beasts as a whole, Like the entire empire is worth

0:41:01.120 --> 0:41:03.640
<v Speaker 2>like a billion dollars or whatever. So you want to

0:41:03.680 --> 0:41:06.200
<v Speaker 2>be like a line where if they want to change

0:41:06.239 --> 0:41:09.279
<v Speaker 2>their focus, like are capital is still aligned with that?

0:41:09.360 --> 0:41:11.400
<v Speaker 2>Like you don't think this this experiment's working.

0:41:11.440 --> 0:41:14.480
<v Speaker 1>Moved to this one and I think it's called CDC.

0:41:14.680 --> 0:41:20.239
<v Speaker 1>If you haven't seen these computer controlled woodworking lathes and carves,

0:41:20.280 --> 0:41:23.880
<v Speaker 1>and they're just astonishing with people Like you think of

0:41:24.000 --> 0:41:28.040
<v Speaker 1>carpentry as kind of old school, it is not. It's

0:41:28.080 --> 0:41:32.319
<v Speaker 1>really fascinating. Coming up, we continue our conversation with Jack

0:41:32.400 --> 0:41:37.200
<v Speaker 1>Rains discussing his new book Young Money, a field guide

0:41:37.239 --> 0:41:41.480
<v Speaker 1>to wealth and purpose in your twenties. I'm Bury Ridults.

0:41:41.480 --> 0:41:46.279
<v Speaker 1>You're listening to Masters in Business on Bloomberg Radio. I'm

0:41:46.320 --> 0:41:50.280
<v Speaker 1>Barry Ridults. You're listening to Masters in Business on Bloomberg Radio.

0:41:51.000 --> 0:41:54.920
<v Speaker 1>My pretty special guest, my kind of.

0:41:54.880 --> 0:41:56.480
<v Speaker 2>Special, somewhat special.

0:41:56.200 --> 0:41:58.880
<v Speaker 1>Somewhat special guests. I'm want to write that down. My

0:41:59.000 --> 0:42:02.759
<v Speaker 1>somewhat special guest is Jack Reins. He is a associate

0:42:02.800 --> 0:42:07.879
<v Speaker 1>at a venture capital firm and a author. I've been

0:42:07.960 --> 0:42:10.839
<v Speaker 1>subscribed to his sub stack Young Money for I don't

0:42:10.840 --> 0:42:11.600
<v Speaker 1>know how many years.

0:42:11.480 --> 0:42:13.120
<v Speaker 2>Has that been, around four or five years?

0:42:13.560 --> 0:42:15.319
<v Speaker 1>Let me know when you get to thirty and you'll

0:42:15.320 --> 0:42:20.440
<v Speaker 1>be onto something. But his new book Young Money, A

0:42:20.480 --> 0:42:25.160
<v Speaker 1>Field Guide to Wealth and Purpose in your twenties, I

0:42:25.320 --> 0:42:27.759
<v Speaker 1>was really taken by it. Not only was it a

0:42:27.840 --> 0:42:33.720
<v Speaker 1>fun read, but I just I not only laughed throughout

0:42:33.760 --> 0:42:36.719
<v Speaker 1>because I just recognized, oh, I did that dumb thing,

0:42:37.800 --> 0:42:41.839
<v Speaker 1>but it also is so wise beyond its years. It's

0:42:41.840 --> 0:42:44.400
<v Speaker 1>hard to imagine that the guy who wrote this was

0:42:44.480 --> 0:42:46.680
<v Speaker 1>twenty six twenty seven when he wrote it twenty seven,

0:42:47.280 --> 0:42:53.080
<v Speaker 1>twenty seven, eight last year of your twenties. So I

0:42:53.239 --> 0:42:57.400
<v Speaker 1>really found it a fun, enjoyable read about a space

0:42:57.440 --> 0:43:01.560
<v Speaker 1>that I normally don't play in Young Money. And there's

0:43:01.600 --> 0:43:05.480
<v Speaker 1>so many things to talk about with this, starting with

0:43:07.000 --> 0:43:11.160
<v Speaker 1>quote I had considered the opportunity cost of how I

0:43:11.320 --> 0:43:16.239
<v Speaker 1>was spending my time, and I adjusted my life accordingly.

0:43:16.680 --> 0:43:20.319
<v Speaker 1>So you're giving the whole game away on page thirteen. Yep,

0:43:20.360 --> 0:43:25.200
<v Speaker 1>you basically say, hey, time is finite, and how and

0:43:25.239 --> 0:43:28.920
<v Speaker 1>when you spend it is really important. Tell us a

0:43:28.920 --> 0:43:32.640
<v Speaker 1>little bit about how you reach that insight back when

0:43:32.640 --> 0:43:34.720
<v Speaker 1>you were in your early in the mid twenties.

0:43:34.760 --> 0:43:38.720
<v Speaker 2>Yes, so, I mean we talked about the spactrading thing earlier,

0:43:38.760 --> 0:43:42.160
<v Speaker 2>but like when I was twenty three, mainly twenty three,

0:43:42.239 --> 0:43:44.440
<v Speaker 2>in a little bit twenty four, my life basically looked

0:43:44.480 --> 0:43:46.839
<v Speaker 2>like this. It was you roll out of bed, throw

0:43:46.840 --> 0:43:50.200
<v Speaker 2>on some sweatpats, grab Chick fil A for breakfast, and

0:43:50.239 --> 0:43:53.280
<v Speaker 2>then you're just like kind of responding to like slack messages.

0:43:53.320 --> 0:43:56.600
<v Speaker 2>You're on zoom calls, spreadsheets, powerpoints, and you're doing all

0:43:56.640 --> 0:43:58.480
<v Speaker 2>of your bedroom. And it had been like that for

0:43:58.520 --> 0:44:00.839
<v Speaker 2>well over a year. And then on the side, like

0:44:01.040 --> 0:44:03.040
<v Speaker 2>you were over here, like you know, training options before

0:44:03.080 --> 0:44:05.640
<v Speaker 2>we jump on this, I had like my work laptop here,

0:44:05.640 --> 0:44:07.880
<v Speaker 2>and then I'm my personal laptop here, and it's like,

0:44:08.120 --> 0:44:10.319
<v Speaker 2>huh interesting, like this spat just got an ounce. So

0:44:10.360 --> 0:44:12.920
<v Speaker 2>I was I was spending like I was like basically

0:44:13.000 --> 0:44:15.520
<v Speaker 2>fake working while just trading stocks all day. And then

0:44:15.600 --> 0:44:17.920
<v Speaker 2>like in the evenings, I you know, you have like

0:44:17.960 --> 0:44:20.640
<v Speaker 2>your entire net worth and some speculative spack and you're

0:44:20.719 --> 0:44:23.080
<v Speaker 2>you can't even sleep straights if futures take you think

0:44:23.080 --> 0:44:26.400
<v Speaker 2>you might lose one hundred thousand dollars. And so I

0:44:26.440 --> 0:44:28.600
<v Speaker 2>was almost in this like self a news holding cell

0:44:28.640 --> 0:44:30.880
<v Speaker 2>of like I couldn't go anywhere really because of COVID,

0:44:30.880 --> 0:44:32.239
<v Speaker 2>and I was stuck at home, and then I was

0:44:32.280 --> 0:44:35.719
<v Speaker 2>just watching screens all day, and thankfully I made some

0:44:35.760 --> 0:44:40.280
<v Speaker 2>money from it. But I just became really aware around

0:44:40.320 --> 0:44:42.239
<v Speaker 2>the time I was about to turn twenty four that

0:44:42.480 --> 0:44:44.560
<v Speaker 2>I had just spent the whole last year of my

0:44:44.680 --> 0:44:49.640
<v Speaker 2>life not really doing anything, especially like call it like

0:44:49.719 --> 0:44:54.560
<v Speaker 2>personal relationships whatever. I was probably a pretty terrible like boyfriend, friend,

0:44:54.760 --> 0:44:57.880
<v Speaker 2>checked out, son, grandson, like I just wasn't like I

0:44:58.200 --> 0:44:59.520
<v Speaker 2>was not in control of ho I was spending my

0:44:59.560 --> 0:45:01.800
<v Speaker 2>time at all. I was kind of like a prisoner

0:45:01.840 --> 0:45:06.320
<v Speaker 2>to like work and COVID and stock market.

0:45:06.239 --> 0:45:09.640
<v Speaker 1>Which is kind of crazy because during the pandemic, you're

0:45:09.680 --> 0:45:12.520
<v Speaker 1>no longer commuting, you're no longer on the same schedule.

0:45:13.160 --> 0:45:17.279
<v Speaker 1>If any of us had a little more prescience, we

0:45:17.400 --> 0:45:21.800
<v Speaker 1>really could have taken full control of our day. Nobody's

0:45:21.880 --> 0:45:23.799
<v Speaker 1>looking over your shoulder at what you're doing. You could

0:45:23.840 --> 0:45:25.000
<v Speaker 1>come and go as you want as long as you

0:45:25.040 --> 0:45:28.319
<v Speaker 1>got your work done whenever. However, everybody was.

0:45:28.320 --> 0:45:32.040
<v Speaker 2>Fine, which is so I mean to the stock trading

0:45:32.040 --> 0:45:33.640
<v Speaker 2>thing I did, like that would not have been happening

0:45:33.680 --> 0:45:36.040
<v Speaker 2>if I was in the office, probably at least not

0:45:36.200 --> 0:45:36.640
<v Speaker 2>as much.

0:45:36.719 --> 0:45:39.720
<v Speaker 1>But what was fascinating as I was reading this because

0:45:39.800 --> 0:45:45.160
<v Speaker 1>I started out trading is you. You nailed the phrase

0:45:45.239 --> 0:45:49.319
<v Speaker 1>you're a prisoner to the screen. You really can't leave

0:45:49.360 --> 0:45:52.319
<v Speaker 1>your desktop. If you're on a desk, at least someone

0:45:52.320 --> 0:45:54.600
<v Speaker 1>could watch a position for you. Hey, I gotta go

0:45:55.080 --> 0:45:57.080
<v Speaker 1>leave for ten minutes. Can you make sure this doesn't

0:45:57.080 --> 0:45:59.520
<v Speaker 1>blow up on me? If it hits this, get me out?

0:46:00.280 --> 0:46:02.279
<v Speaker 1>You could do that. But if you're doing this from

0:46:02.360 --> 0:46:05.600
<v Speaker 1>your bedroom and you have a lot of positions on you,

0:46:05.600 --> 0:46:07.919
<v Speaker 1>you're you have no other bandwidth for anything else.

0:46:08.000 --> 0:46:10.960
<v Speaker 2>It's just push notifications on for everything. You go to

0:46:11.000 --> 0:46:13.239
<v Speaker 2>the gym, you're checking your phone every two minutes. It

0:46:13.320 --> 0:46:15.720
<v Speaker 2>was just like a little bit nauseating, right, and.

0:46:15.680 --> 0:46:16.719
<v Speaker 1>Uh and exhausting.

0:46:16.840 --> 0:46:19.480
<v Speaker 2>Yeah, And like I I honestly just felt pretty like

0:46:19.520 --> 0:46:23.640
<v Speaker 2>mentally exhausted from the like always being on and I

0:46:23.800 --> 0:46:26.120
<v Speaker 2>just kind of had enough. And I also found my

0:46:26.280 --> 0:46:28.320
<v Speaker 2>job pretty unfulfilling, and I knew I was going to

0:46:28.400 --> 0:46:29.839
<v Speaker 2>leave it in a year, And it was just like

0:46:30.760 --> 0:46:32.680
<v Speaker 2>all of these things came to a head and I

0:46:32.760 --> 0:46:35.719
<v Speaker 2>was like, Okay, let's be really intentional here about like

0:46:35.800 --> 0:46:38.120
<v Speaker 2>how do I want to spend Like if I know

0:46:38.160 --> 0:46:39.840
<v Speaker 2>I'm going to grad school in a year, like, how

0:46:39.880 --> 0:46:41.520
<v Speaker 2>do I actually want to spend the next year? Is

0:46:41.520 --> 0:46:43.360
<v Speaker 2>it keep going in the motions of the job that

0:46:43.400 --> 0:46:45.319
<v Speaker 2>I know I'm going to leave to go do something else?

0:46:45.800 --> 0:46:48.440
<v Speaker 2>Is that like like try to like trade back the

0:46:48.480 --> 0:46:50.680
<v Speaker 2>money I just lost lost on that trade gone wrong?

0:46:51.440 --> 0:46:53.280
<v Speaker 2>The thing I kind of wanted to do is like, honestly,

0:46:53.360 --> 0:46:55.759
<v Speaker 2>just go have an adventure having just been cooped up

0:46:55.800 --> 0:46:58.799
<v Speaker 2>for a year and a half. And yeah, so that

0:46:58.960 --> 0:47:00.480
<v Speaker 2>like it was just like all of that came to

0:47:00.560 --> 0:47:03.200
<v Speaker 2>ahead and I was like I should just I mean,

0:47:03.239 --> 0:47:05.040
<v Speaker 2>it's like the opening line of the book, just blow

0:47:05.120 --> 0:47:07.560
<v Speaker 2>up my life and go do something crazy. And that's

0:47:07.760 --> 0:47:09.600
<v Speaker 2>kind of what I did, and I went to Barcelona.

0:47:09.960 --> 0:47:15.000
<v Speaker 1>You hit the eject button. The concept of time comes

0:47:15.080 --> 0:47:19.240
<v Speaker 1>up over and over throughout the book, both generally and specifically.

0:47:20.640 --> 0:47:24.800
<v Speaker 1>One of the things you write about is defining decades differently,

0:47:24.840 --> 0:47:28.319
<v Speaker 1>and about the opportunity cost of your twenties. A lot

0:47:28.320 --> 0:47:32.000
<v Speaker 1>of people who just buckle down and grind it out

0:47:32.040 --> 0:47:36.240
<v Speaker 1>through their twenties. You say that for many people that's

0:47:36.280 --> 0:47:39.719
<v Speaker 1>a trap. Smart twenty something's fall into to discuss that.

0:47:40.120 --> 0:47:42.560
<v Speaker 2>So I and I think this is especially true in

0:47:42.640 --> 0:47:46.960
<v Speaker 2>the like call it hyper competitive, like New York, San Francisco,

0:47:47.160 --> 0:47:51.879
<v Speaker 2>maybe like Chicago, DC areas where you're surrounded by very

0:47:51.920 --> 0:47:54.160
<v Speaker 2>smart people who went to really good schools and they

0:47:54.200 --> 0:47:56.560
<v Speaker 2>go into like at least for like an early twenty

0:47:56.560 --> 0:48:00.239
<v Speaker 2>something high paying job, but you're also objectively pretty, but

0:48:00.280 --> 0:48:02.359
<v Speaker 2>you don't know anything you like, don't like No twenty

0:48:02.400 --> 0:48:05.640
<v Speaker 2>two especially guys like yeah.

0:48:05.640 --> 0:48:09.000
<v Speaker 1>And tell me when I get to grow out of that.

0:48:09.120 --> 0:48:12.760
<v Speaker 2>I don't know. I mean you tell me. You're sitting

0:48:12.760 --> 0:48:14.759
<v Speaker 2>there and it's like, okay, like what do I optimize for?

0:48:15.000 --> 0:48:19.360
<v Speaker 2>And the obvious thing is money, and the like derivative

0:48:19.400 --> 0:48:23.040
<v Speaker 2>of that is status, right where high paying jobs are

0:48:23.160 --> 0:48:27.960
<v Speaker 2>typically higher status jobs. And I think it's when you

0:48:28.040 --> 0:48:30.640
<v Speaker 2>don't have anything else. It's like like a north Star.

0:48:30.880 --> 0:48:33.879
<v Speaker 2>You kind of go for like the like ambitious thing

0:48:33.920 --> 0:48:36.200
<v Speaker 2>that will pay you well, that sounds impressive over and

0:48:36.239 --> 0:48:39.279
<v Speaker 2>over again, and like, to be totally clear, there's nothing

0:48:39.320 --> 0:48:41.200
<v Speaker 2>wrong with that, and that's also much better than like

0:48:42.120 --> 0:48:45.120
<v Speaker 2>being a bomb and not doing anything. But you almost

0:48:46.080 --> 0:48:49.200
<v Speaker 2>if you fall into that trap of like having some

0:48:49.280 --> 0:48:51.520
<v Speaker 2>expectation of what you should do without it actually being

0:48:51.560 --> 0:48:53.640
<v Speaker 2>like your own original thought like oh I want to

0:48:53.640 --> 0:48:56.080
<v Speaker 2>go do this, you almost become instead of being like

0:48:56.120 --> 0:48:58.360
<v Speaker 2>the protagonist of your own life, you're just kind of

0:48:58.400 --> 0:49:02.000
<v Speaker 2>like filling a preordain role, Like you're almost like an actor, right,

0:49:02.120 --> 0:49:03.080
<v Speaker 2>is how I think about.

0:49:02.840 --> 0:49:05.480
<v Speaker 1>It, and in someone else's play, right.

0:49:05.520 --> 0:49:10.520
<v Speaker 2>And I think the thing like I think the implicit

0:49:10.560 --> 0:49:12.560
<v Speaker 2>bat people are making when they do that is I

0:49:12.600 --> 0:49:14.400
<v Speaker 2>will like earn enough money and hit a level of

0:49:14.480 --> 0:49:17.799
<v Speaker 2>stability where I can head eject, which you can do,

0:49:18.120 --> 0:49:22.960
<v Speaker 2>but you can't buy back the opportunities that you would

0:49:23.000 --> 0:49:24.680
<v Speaker 2>have had in your twenties when you're in your like

0:49:24.719 --> 0:49:25.400
<v Speaker 2>mid thirties.

0:49:25.800 --> 0:49:30.520
<v Speaker 1>So another quote, there's no saving time, there's no investing time.

0:49:31.040 --> 0:49:35.440
<v Speaker 1>There is only spending time. And sentences like that is

0:49:35.440 --> 0:49:39.000
<v Speaker 1>why I say this book is wise beyond its years,

0:49:39.000 --> 0:49:44.759
<v Speaker 1>because I know people who figure that out in their fifties, sixties, seventies,

0:49:44.880 --> 0:49:49.080
<v Speaker 1>not in their twenties. So kudos to you forgetting there

0:49:49.760 --> 0:49:54.800
<v Speaker 1>to tell us what led you to that conclusion and

0:49:55.200 --> 0:50:01.040
<v Speaker 1>how much did the pandemic lockdown accidentally lead to these insights.

0:50:01.440 --> 0:50:07.360
<v Speaker 2>I think I became much more introspective much younger, because,

0:50:08.080 --> 0:50:10.360
<v Speaker 2>like you just, I mean, I had roommates them, like

0:50:10.400 --> 0:50:12.880
<v Speaker 2>I just wasn't spending like that much time in a

0:50:12.880 --> 0:50:15.520
<v Speaker 2>normal day to day and I'm a very like sociable

0:50:15.560 --> 0:50:18.080
<v Speaker 2>guy who like likes to hang out with people during

0:50:18.080 --> 0:50:20.160
<v Speaker 2>the day. That gets removed and you're just in your

0:50:20.160 --> 0:50:22.319
<v Speaker 2>head a lot, and you become really reflective of like

0:50:22.719 --> 0:50:25.360
<v Speaker 2>how you're spending your time, what you're motivated by. So

0:50:25.640 --> 0:50:28.440
<v Speaker 2>it was just like this again, I don't like this

0:50:28.480 --> 0:50:30.840
<v Speaker 2>book probably wouldn't have happened if COVID didn't happen, because

0:50:30.880 --> 0:50:34.040
<v Speaker 2>most of these like reflections were downstream of this hole

0:50:34.239 --> 0:50:38.000
<v Speaker 2>just being like kind of in like an isolated stage

0:50:38.000 --> 0:50:40.279
<v Speaker 2>of life at a point where like you should really

0:50:40.320 --> 0:50:44.440
<v Speaker 2>just be like in an office grinding. So I think

0:50:44.480 --> 0:50:46.640
<v Speaker 2>that was a big part of it. Hilariously, I like

0:50:46.800 --> 0:50:48.799
<v Speaker 2>I mentioned, like the second chapter of the book, I

0:50:48.920 --> 0:50:51.880
<v Speaker 2>used to be terrified of flying, and U like, like

0:50:51.920 --> 0:50:53.759
<v Speaker 2>I'd fly all the time down I don't care. But

0:50:53.840 --> 0:50:56.279
<v Speaker 2>for some reason, turbulence just like kicked my When I

0:50:56.280 --> 0:50:59.120
<v Speaker 2>was younger and I was on a flight to Colorado

0:50:59.280 --> 0:51:02.080
<v Speaker 2>about a year and a pandemic for ski trip, plame

0:51:02.200 --> 0:51:05.440
<v Speaker 2>was basically empty. It was awesome. We had a super

0:51:05.640 --> 0:51:08.680
<v Speaker 2>super turbulent takeoff and it was just bumpy from Atlanta

0:51:08.760 --> 0:51:11.279
<v Speaker 2>basically all the way to like Kansas City, and I

0:51:11.320 --> 0:51:13.839
<v Speaker 2>was just sitting there thinking the whole time, we're tolling

0:51:13.880 --> 0:51:15.680
<v Speaker 2>to do die. Those thing's going now we're gonna die.

0:51:15.719 --> 0:51:18.719
<v Speaker 2>Like it's I'm twenty three, it's over, I'm dead. And

0:51:18.719 --> 0:51:23.240
<v Speaker 2>we obviously landed. I didn't die, but like some again

0:51:23.440 --> 0:51:27.279
<v Speaker 2>totally random, but just something about that put that thought

0:51:27.440 --> 0:51:29.839
<v Speaker 2>back my mind, like like at some point you are

0:51:29.880 --> 0:51:32.200
<v Speaker 2>going to die, and it's not like up until that,

0:51:32.440 --> 0:51:34.480
<v Speaker 2>I just thought I was gonna live forever, Like that's

0:51:34.520 --> 0:51:36.440
<v Speaker 2>a not stupid, but.

0:51:37.480 --> 0:51:40.759
<v Speaker 1>You don't really think about that in your twenties. When

0:51:40.960 --> 0:51:43.719
<v Speaker 1>most people are in their twenties, they're immortal. You're not

0:51:43.840 --> 0:51:46.080
<v Speaker 1>thinking about, well, one day I'm gonna die.

0:51:46.239 --> 0:51:48.799
<v Speaker 2>Yeah, And that became like a forcing function for like, okay,

0:51:48.840 --> 0:51:52.000
<v Speaker 2>let's work backwards from I finally got over the fear

0:51:52.000 --> 0:51:53.560
<v Speaker 2>of flying. But it's like, all right, like we are,

0:51:53.800 --> 0:51:56.080
<v Speaker 2>you know, we're on the clock, and what do I

0:51:56.080 --> 0:51:57.960
<v Speaker 2>want to do with it? And so it was like

0:51:58.000 --> 0:52:01.440
<v Speaker 2>a complete fluke from a turbulent flight kind of forced

0:52:01.480 --> 0:52:03.520
<v Speaker 2>a lot of introspection that have been bubbling under the

0:52:03.560 --> 0:52:06.279
<v Speaker 2>surface for probably the prior year. I was like, all right,

0:52:06.320 --> 0:52:08.400
<v Speaker 2>like I should be doing what I want with my

0:52:08.560 --> 0:52:11.200
<v Speaker 2>time rather than just letting inertia kind of do its thing.

0:52:11.640 --> 0:52:15.279
<v Speaker 2>And it was that like call it like awareness of

0:52:15.320 --> 0:52:18.480
<v Speaker 2>mortality that became like a forcing function for basically what

0:52:18.600 --> 0:52:21.200
<v Speaker 2>I've done in the last four and a half years

0:52:21.200 --> 0:52:24.600
<v Speaker 2>since then, like, be in control of your time. Don't

0:52:25.160 --> 0:52:27.520
<v Speaker 2>don't be a don't be like a passive participant in

0:52:27.520 --> 0:52:28.120
<v Speaker 2>your own life.

0:52:29.320 --> 0:52:32.880
<v Speaker 1>The difference between money and time is that money is

0:52:32.920 --> 0:52:40.080
<v Speaker 1>both infinite and fungible. Time is neither. This this is

0:52:40.120 --> 0:52:41.560
<v Speaker 1>a philosophical concept.

0:52:41.640 --> 0:52:43.360
<v Speaker 2>I consider myself a bit of a philosopher.

0:52:43.400 --> 0:52:48.520
<v Speaker 1>Okay, I'm with you, I'm there with you. What's your

0:52:48.560 --> 0:52:53.480
<v Speaker 1>conclusion when you realize that money is both infinite and fungible.

0:52:53.480 --> 0:52:57.800
<v Speaker 2>I think you like need to be really aware of

0:52:59.680 --> 0:53:01.440
<v Speaker 2>how much money it takes to get what you want

0:53:01.440 --> 0:53:04.160
<v Speaker 2>out of life at various life stages. To your point, earlier,

0:53:04.160 --> 0:53:05.879
<v Speaker 2>you can kind of scrape by in your twenties maybe

0:53:05.960 --> 0:53:09.160
<v Speaker 2>early thirties and like still enjoy yourself. And the older

0:53:09.200 --> 0:53:12.160
<v Speaker 2>you get, the more expensive it gets. Ideally you're making

0:53:12.200 --> 0:53:13.919
<v Speaker 2>more and more money over the course of your life

0:53:13.960 --> 0:53:16.560
<v Speaker 2>as well. So like my conclusion on that is it's

0:53:16.560 --> 0:53:19.640
<v Speaker 2>like counter to a financial device. But like young people

0:53:19.640 --> 0:53:21.759
<v Speaker 2>shouldn't penny pinch so much if they have like fun,

0:53:21.800 --> 0:53:24.239
<v Speaker 2>interesting stuff they want to spend the money on. The

0:53:24.640 --> 0:53:26.960
<v Speaker 2>caveat to that is like you should put yourself in

0:53:27.000 --> 0:53:30.359
<v Speaker 2>a position where there are like high income outcomes from

0:53:30.400 --> 0:53:33.280
<v Speaker 2>that over time. But like it's okay to be twenty

0:53:33.280 --> 0:53:35.240
<v Speaker 2>five and not be rich if it means like spending

0:53:35.239 --> 0:53:36.960
<v Speaker 2>money on fun stuff with your friends. Right.

0:53:37.280 --> 0:53:40.799
<v Speaker 1>So, you're not a fan of the fire movement, the

0:53:40.960 --> 0:53:43.480
<v Speaker 1>early retirement movement.

0:53:43.360 --> 0:53:45.680
<v Speaker 2>Not when it's taken to the extreme. I think that

0:53:45.800 --> 0:53:49.440
<v Speaker 2>the core idea of like having enough money saved up

0:53:49.440 --> 0:53:52.080
<v Speaker 2>where like you control your own destiny is healthy and

0:53:52.120 --> 0:53:55.160
<v Speaker 2>good and admirable. I think when you make the accumulation

0:53:55.239 --> 0:53:58.400
<v Speaker 2>of capital to like escape the labor force as like

0:53:58.440 --> 0:54:00.360
<v Speaker 2>an end goal, you just set yourself up to be

0:54:00.400 --> 0:54:05.080
<v Speaker 2>bored and almost beyond that, when you're like overoptimize for

0:54:05.160 --> 0:54:07.160
<v Speaker 2>fire and your whole thing is like I want to

0:54:07.200 --> 0:54:09.880
<v Speaker 2>opt out of work, you're probably gonna hit that in

0:54:09.920 --> 0:54:11.960
<v Speaker 2>your like early forties, when all of your peers are

0:54:12.000 --> 0:54:14.360
<v Speaker 2>peak work. You're not gonna be able to relate to

0:54:14.360 --> 0:54:17.200
<v Speaker 2>anybody after everal years. Against there's a lot of I

0:54:17.200 --> 0:54:20.160
<v Speaker 2>think when you take the fire movement too far. There's

0:54:20.200 --> 0:54:22.120
<v Speaker 2>like social costs to that that are harder to see

0:54:22.120 --> 0:54:24.879
<v Speaker 2>when you're looking at a spreadsheet. But it's just like,

0:54:25.440 --> 0:54:27.799
<v Speaker 2>and you have to forgo so many things you would

0:54:27.800 --> 0:54:29.960
<v Speaker 2>probably prefer to spend money on in your twenties and

0:54:30.000 --> 0:54:32.839
<v Speaker 2>thirties to hit that. It's just not I don't think

0:54:32.840 --> 0:54:34.880
<v Speaker 2>you should like go into crazy debt and you should

0:54:34.880 --> 0:54:36.680
<v Speaker 2>max out your four one K if you can and

0:54:36.680 --> 0:54:39.720
<v Speaker 2>all this stuff, But like you just you shouldn't pass

0:54:39.800 --> 0:54:42.000
<v Speaker 2>up on life to accumulate cash to be able to

0:54:42.000 --> 0:54:44.840
<v Speaker 2>opt out of another part of life being work. Is

0:54:44.920 --> 0:54:46.239
<v Speaker 2>kind of my take on it.

0:54:46.320 --> 0:54:49.080
<v Speaker 1>No, that makes a lot of sense. I love this quote.

0:54:49.640 --> 0:54:53.200
<v Speaker 1>Many of life's adventures are adventures only because you're twenty

0:54:53.200 --> 0:54:57.960
<v Speaker 1>two and broken stupid and you're surrounded by other broke,

0:54:58.120 --> 0:55:01.840
<v Speaker 1>stupid twenty two year olds. This is a feature, not

0:55:01.960 --> 0:55:06.279
<v Speaker 1>a flaw of being young. Lean into it, yep, tell

0:55:06.360 --> 0:55:10.200
<v Speaker 1>us about how you saw that. What is it about

0:55:10.239 --> 0:55:13.840
<v Speaker 1>being twenty two and broken stupid that has to be embraced?

0:55:14.080 --> 0:55:17.560
<v Speaker 2>So like I, I mean, I spent that whole year

0:55:17.600 --> 0:55:20.200
<v Speaker 2>of being I guess I was technically twenty four, but

0:55:20.480 --> 0:55:21.960
<v Speaker 2>I was with a lot of twenty two year olds

0:55:21.960 --> 0:55:24.440
<v Speaker 2>who are like this whole like hostel hopping things hilarious, right,

0:55:24.480 --> 0:55:27.640
<v Speaker 2>because it's basically a bunch of kids, like studying abroad.

0:55:27.800 --> 0:55:30.239
<v Speaker 2>It's a bunch of people fresh out of college. It's

0:55:30.239 --> 0:55:32.359
<v Speaker 2>a bunch of Europeans taking a gap year, a bunch

0:55:32.360 --> 0:55:34.439
<v Speaker 2>of Americans fresh out of college, and then a bunch

0:55:34.480 --> 0:55:36.879
<v Speaker 2>of like call twenty three to twenty six year olds

0:55:36.880 --> 0:55:38.720
<v Speaker 2>who worked for a couple of years and took a break,

0:55:39.120 --> 0:55:42.719
<v Speaker 2>and you're all just like in bunk beds. Everybody has

0:55:42.760 --> 0:55:44.719
<v Speaker 2>a shared goal of like, I'm just trying to have

0:55:44.800 --> 0:55:47.399
<v Speaker 2>cheap fun for a little while, and it makes every

0:55:47.520 --> 0:55:51.200
<v Speaker 2>situation really really funny. Like some guys want to go

0:55:51.320 --> 0:55:53.919
<v Speaker 2>from Sevilla, Spain to Paris and they're trying to game

0:55:53.960 --> 0:55:56.239
<v Speaker 2>out like it's two hundred dollars to fly, but if

0:55:56.280 --> 0:55:57.920
<v Speaker 2>we take a train ticket and then sleep in a

0:55:57.960 --> 0:56:01.680
<v Speaker 2>train station for six hours, we can there for twelve dollars.

0:56:01.640 --> 0:56:04.040
<v Speaker 1>And or and avoid a hotel room, right, and.

0:56:04.000 --> 0:56:06.200
<v Speaker 2>Avoid a hotel room and extend our European trip like

0:56:06.200 --> 0:56:09.879
<v Speaker 2>eight more days. Right, So or you have life?

0:56:10.000 --> 0:56:13.280
<v Speaker 1>Did that right? You went from Barcelona to where in Europe?

0:56:13.600 --> 0:56:18.360
<v Speaker 2>I mean I I covered I was there from August

0:56:18.400 --> 0:56:20.960
<v Speaker 2>cit December, and then I went to Latin America a

0:56:21.000 --> 0:56:22.800
<v Speaker 2>month later for a few months, and back to Europe

0:56:22.800 --> 0:56:26.360
<v Speaker 2>and that August Citycember thing. I think I went to

0:56:26.440 --> 0:56:29.520
<v Speaker 2>like nineteen different countries in four months, and it was

0:56:29.600 --> 0:56:32.120
<v Speaker 2>just there was no itinerary. I would just go somewhere

0:56:32.200 --> 0:56:34.560
<v Speaker 2>and then I would meet some people and they would say, hey, dude,

0:56:34.560 --> 0:56:36.200
<v Speaker 2>we're going to Prog next. Do you want to come?

0:56:36.200 --> 0:56:37.960
<v Speaker 2>And I was like sure, sure, And I meet this

0:56:38.000 --> 0:56:40.879
<v Speaker 2>guy in Prague He's like, yo, I heard Budapest is great.

0:56:40.920 --> 0:56:42.600
<v Speaker 2>I'm like all right, And then I was like, we're

0:56:42.600 --> 0:56:44.759
<v Speaker 2>going to crack al Poland next I met a kid

0:56:44.760 --> 0:56:46.600
<v Speaker 2>at a hostel in Crackowl who pitched me on his

0:56:46.600 --> 0:56:48.879
<v Speaker 2>startup in San Francisco a year ago, like talking about

0:56:48.920 --> 0:56:51.719
<v Speaker 2>weird yeah, small world stuff. But it was just like

0:56:52.520 --> 0:56:56.279
<v Speaker 2>I went like pure optionality for a year and it

0:56:56.360 --> 0:56:58.919
<v Speaker 2>was just like anybody I meet interesting was doing something cool.

0:56:58.920 --> 0:57:00.399
<v Speaker 2>I'm going to go with them, like oh I heard

0:57:00.400 --> 0:57:03.080
<v Speaker 2>Tromso Norway. You can see the northern lights. Let's go

0:57:03.160 --> 0:57:06.040
<v Speaker 2>dog sledding up there, and like you do that. So

0:57:07.520 --> 0:57:10.399
<v Speaker 2>the ability to just like cast a really wide net

0:57:10.440 --> 0:57:13.840
<v Speaker 2>because when like cheap thrills are fighting, like having to

0:57:13.880 --> 0:57:15.600
<v Speaker 2>sleep on a train or I have a buck bed

0:57:15.640 --> 0:57:18.400
<v Speaker 2>with a stranger. It's just like it's fine, like when

0:57:18.440 --> 0:57:21.640
<v Speaker 2>you're when you're a kid, you just don't care. I like,

0:57:21.720 --> 0:57:23.320
<v Speaker 2>I'm still in my twenties now, but that would just

0:57:23.360 --> 0:57:24.880
<v Speaker 2>sound awful, Like I don't want to be in a

0:57:25.000 --> 0:57:27.040
<v Speaker 2>room with like twelve strangers and worry about my stuff

0:57:27.040 --> 0:57:27.640
<v Speaker 2>getting stolen.

0:57:27.680 --> 0:57:30.400
<v Speaker 1>That sounds terrible, but like twenty four, you got nothing

0:57:30.400 --> 0:57:31.280
<v Speaker 1>to get stolen anyway.

0:57:31.360 --> 0:57:33.360
<v Speaker 2>Yeah, it's like where they gonna take my backpack? We

0:57:33.440 --> 0:57:35.520
<v Speaker 2>had a couple of like Czara T shirts and flip flops,

0:57:35.520 --> 0:57:37.600
<v Speaker 2>sick Like I'll go play poker and win twenty bucks

0:57:37.600 --> 0:57:40.200
<v Speaker 2>and go buy another one. It's fine. So and there's

0:57:40.320 --> 0:57:42.000
<v Speaker 2>versions of that to play out and everything, right, Like

0:57:42.040 --> 0:57:45.720
<v Speaker 2>I'm I don't think everybody has to go backpack Europe.

0:57:45.720 --> 0:57:47.720
<v Speaker 2>But like you got to San Francisco and there's like

0:57:47.720 --> 0:57:49.920
<v Speaker 2>twenty four year old startup founders that are sleeping in

0:57:49.920 --> 0:57:51.440
<v Speaker 2>the office with a bunch of their buddies and they

0:57:51.440 --> 0:57:55.200
<v Speaker 2>are having a blast. Like they're in objectively like horrid

0:57:55.240 --> 0:57:57.680
<v Speaker 2>living conditions. They don't even notice because they're like twenty

0:57:57.720 --> 0:57:59.840
<v Speaker 2>three or twenty two or whatever, like you can you

0:58:00.080 --> 0:58:03.680
<v Speaker 2>can just really lean into like adverse living conditions and

0:58:03.720 --> 0:58:06.440
<v Speaker 2>find them enjoyable rather than like they don't like take

0:58:06.440 --> 0:58:08.720
<v Speaker 2>away from your life. They create really funny stories.

0:58:10.240 --> 0:58:15.080
<v Speaker 1>I'm always fascinated by the pursue your passion recommendation that

0:58:15.160 --> 0:58:19.680
<v Speaker 1>so many people make. You say, pursue your passion is

0:58:19.920 --> 0:58:23.400
<v Speaker 1>terrible career advice. Yeah, give us some color on that. So, like,

0:58:23.640 --> 0:58:27.440
<v Speaker 1>and you're giving this from someone who is pursuing their passion.

0:58:27.600 --> 0:58:31.040
<v Speaker 2>So my my like more specific take on that is

0:58:31.080 --> 0:58:34.280
<v Speaker 2>you shouldn't bank your income on a thing you're passionate about.

0:58:34.520 --> 0:58:36.480
<v Speaker 2>The example that I give is, like, I love writing.

0:58:36.560 --> 0:58:38.680
<v Speaker 2>It's a it's a thing that like I've enjoyed, I'll

0:58:38.680 --> 0:58:40.880
<v Speaker 2>do the rest of my life, whether it's books, blogs,

0:58:41.000 --> 0:58:44.960
<v Speaker 2>it's something I'll always incorporate. My initial job out of

0:58:44.960 --> 0:58:49.160
<v Speaker 2>business school was columnist, podcast or media guy like effectively

0:58:49.160 --> 0:58:52.200
<v Speaker 2>a media startup, and I actually found it stressful, where

0:58:52.200 --> 0:58:54.040
<v Speaker 2>like every single day I had to like put something

0:58:54.040 --> 0:58:57.400
<v Speaker 2>out and then I also was sitting there thinking this

0:58:57.480 --> 0:58:59.600
<v Speaker 2>is draining the fun of like writing. Like I wasn't

0:58:59.640 --> 0:59:01.320
<v Speaker 2>monetized as in my blog. It was just a thing

0:59:01.320 --> 0:59:03.200
<v Speaker 2>that I like doing, and all of a sudden, now

0:59:03.360 --> 0:59:05.280
<v Speaker 2>I don't have energy to work on that fun thing

0:59:05.400 --> 0:59:07.480
<v Speaker 2>because I spend all that energy on the thing I'm

0:59:07.520 --> 0:59:11.080
<v Speaker 2>paid to do. So the issue with like chasing your

0:59:11.080 --> 0:59:13.800
<v Speaker 2>passion is one, a lot of passions aren't that lucrative.

0:59:14.040 --> 0:59:16.880
<v Speaker 2>Two the second that your paycheck is dependent on you

0:59:16.960 --> 0:59:19.160
<v Speaker 2>doing that thing over and over and over again, it

0:59:19.200 --> 0:59:21.160
<v Speaker 2>can start feeling more like a chore than like fun.

0:59:21.520 --> 0:59:25.320
<v Speaker 2>So the actual advice I have is, like, pursue stuff

0:59:25.320 --> 0:59:28.400
<v Speaker 2>that you're pretty interested in that can pay you, whether

0:59:28.480 --> 0:59:30.280
<v Speaker 2>or not you're like most jobs are boring for a

0:59:30.320 --> 0:59:31.920
<v Speaker 2>lot of the time, so whether or not you're passionate

0:59:31.920 --> 0:59:34.800
<v Speaker 2>about it, a thing that you're like interested in and

0:59:34.840 --> 0:59:37.440
<v Speaker 2>like have an inclination for and have some skills at,

0:59:37.800 --> 0:59:40.720
<v Speaker 2>go do that for a career, and then use that

0:59:40.760 --> 0:59:43.200
<v Speaker 2>to like subsidize your ability to work on the fun stuff.

0:59:43.280 --> 0:59:46.400
<v Speaker 2>Like I, you know, like writing writing books and blogs

0:59:46.480 --> 0:59:48.320
<v Speaker 2>is like a thing I want to do independent of

0:59:48.320 --> 0:59:51.640
<v Speaker 2>the financial outcomes from it. I'm pivoted from media to

0:59:51.680 --> 0:59:54.960
<v Speaker 2>venture capital because, like, I like the offshoot opportunities of

0:59:55.360 --> 0:59:59.479
<v Speaker 2>investing in tech companies, and that's just like a better

0:59:59.520 --> 1:00:01.080
<v Speaker 2>world to be in for a career path.

1:00:01.880 --> 1:00:05.400
<v Speaker 1>Last question before we get to our favorite questions that

1:00:05.440 --> 1:00:08.240
<v Speaker 1>we ask all of our somewhat special guests.

1:00:08.200 --> 1:00:09.120
<v Speaker 2>What special guests?

1:00:09.200 --> 1:00:12.480
<v Speaker 1>How do I know I'm making the most of my time?

1:00:12.960 --> 1:00:15.400
<v Speaker 2>So the last chapter of the book is called are

1:00:15.440 --> 1:00:18.720
<v Speaker 2>You having Fun Yet? Which I think is like, I

1:00:18.760 --> 1:00:21.040
<v Speaker 2>think fun is an underrated barometer that you're actually doing

1:00:21.080 --> 1:00:24.680
<v Speaker 2>the right stuff with your life. And it sounds silly

1:00:24.960 --> 1:00:27.040
<v Speaker 2>at like first glance, but my take on it is,

1:00:27.400 --> 1:00:29.560
<v Speaker 2>I think the definition of fun and what you find

1:00:29.560 --> 1:00:33.040
<v Speaker 2>to be fun changes as you go through life different stages.

1:00:33.120 --> 1:00:35.520
<v Speaker 2>Where when I was like twenty three or twenty four,

1:00:35.680 --> 1:00:39.160
<v Speaker 2>it was just doing dumb, hostile hopping stuff and like

1:00:39.200 --> 1:00:41.680
<v Speaker 2>getting drunk all the time or whatever, and it was great.

1:00:41.760 --> 1:00:43.400
<v Speaker 2>Now I get drunk a lot less of the time.

1:00:43.400 --> 1:00:46.720
<v Speaker 2>It's still slightly a little bit more refined though, but

1:00:46.880 --> 1:00:49.680
<v Speaker 2>like you know, once you get a little further in

1:00:49.680 --> 1:00:52.640
<v Speaker 2>your career, like having real career success and making strides

1:00:52.720 --> 1:00:56.160
<v Speaker 2>is like a source of like joy and personal achievement.

1:00:56.200 --> 1:00:58.880
<v Speaker 2>When I was in college and playing football, like football

1:00:59.080 --> 1:01:03.600
<v Speaker 2>objectively sucked, but like I like, playing college football really sucks,

1:01:03.600 --> 1:01:04.960
<v Speaker 2>and anybody who's played it will tell you that.

1:01:05.000 --> 1:01:07.120
<v Speaker 1>But it's like a by the way, the description of

1:01:07.160 --> 1:01:09.760
<v Speaker 1>the work at routines in the six am wind sprints

1:01:09.800 --> 1:01:13.160
<v Speaker 1>and but but when you know deep into the season

1:01:13.200 --> 1:01:16.200
<v Speaker 1>the coach tap rains we get in there.

1:01:16.440 --> 1:01:19.120
<v Speaker 2>Yeah, it's like it's like an incredibly like fulfilled Like

1:01:19.160 --> 1:01:21.480
<v Speaker 2>it's like going from a walk on to be putting

1:01:21.480 --> 1:01:23.920
<v Speaker 2>on scholarship and then like getting made team captain my

1:01:23.960 --> 1:01:27.640
<v Speaker 2>senior year, Like that was a much cooler fulfilling moment

1:01:27.680 --> 1:01:29.920
<v Speaker 2>than like anything I did before or after it. Like

1:01:30.240 --> 1:01:32.840
<v Speaker 2>I think it was because it was really really hard, right.

1:01:32.920 --> 1:01:34.480
<v Speaker 1>So in a real sense of achievement.

1:01:34.640 --> 1:01:36.560
<v Speaker 2>Yeah, like it was a it was a hard thing

1:01:36.600 --> 1:01:40.040
<v Speaker 2>and I'd like executed on it, so but it was fun.

1:01:40.080 --> 1:01:41.880
<v Speaker 2>So my kind of definition of fun is if you

1:01:41.960 --> 1:01:44.120
<v Speaker 2>like find joy in the suck, then you're probably doing

1:01:44.160 --> 1:01:46.880
<v Speaker 2>the right thing. And like that could be being like

1:01:46.960 --> 1:01:50.080
<v Speaker 2>groggy and hungover like on a park mentioned Spain, but

1:01:50.120 --> 1:01:52.120
<v Speaker 2>you feel like you're living out an adventure, or it

1:01:52.160 --> 1:01:55.120
<v Speaker 2>could be like going after like a really ambitious career

1:01:55.240 --> 1:01:58.520
<v Speaker 2>and like excelling in it. And it's you know, I

1:01:58.560 --> 1:02:00.200
<v Speaker 2>think a lot of people as they get firs they're

1:02:00.200 --> 1:02:02.960
<v Speaker 2>in their careers, they keep chasing that ambition high off

1:02:03.000 --> 1:02:05.080
<v Speaker 2>of that to the detriment of like their family or

1:02:05.120 --> 1:02:07.000
<v Speaker 2>other parts of their life. I think a lot of

1:02:07.040 --> 1:02:11.880
<v Speaker 2>young people like just start like I think the biggest

1:02:11.880 --> 1:02:15.480
<v Speaker 2>mistake you can make is like keeping a prior version

1:02:15.680 --> 1:02:18.440
<v Speaker 2>of u's like benchmark or idea of what they should

1:02:18.440 --> 1:02:20.200
<v Speaker 2>be doing with their time and trying to like force

1:02:20.240 --> 1:02:24.120
<v Speaker 2>apply that to a future version, or trying to pull

1:02:24.200 --> 1:02:26.480
<v Speaker 2>forward a future version too early in your life at

1:02:26.480 --> 1:02:28.360
<v Speaker 2>the expense of the fun stuff you want to do now.

1:02:28.400 --> 1:02:32.960
<v Speaker 2>And I think just having a very very strong sense of, like,

1:02:33.200 --> 1:02:35.080
<v Speaker 2>what are the most important things right now that bring

1:02:35.120 --> 1:02:38.800
<v Speaker 2>me fulfillment and then going after those is the recipe

1:02:38.840 --> 1:02:39.760
<v Speaker 2>to a good life.

1:02:40.120 --> 1:02:43.000
<v Speaker 1>And the sequel to this fine joy in the suck

1:02:43.560 --> 1:02:44.320
<v Speaker 1>is a great.

1:02:44.480 --> 1:02:46.680
<v Speaker 2>Could be title. I just call it like middle aged money.

1:02:46.720 --> 1:02:48.240
<v Speaker 2>Once I get my thirties.

1:02:48.120 --> 1:02:50.800
<v Speaker 1>Well, you can do something every decade. You have a

1:02:50.840 --> 1:02:56.640
<v Speaker 1>built in model your money, slightly older money and money.

1:02:56.680 --> 1:02:58.680
<v Speaker 1>You got a whole run of things. All right, Let's

1:02:58.760 --> 1:03:02.680
<v Speaker 1>jump to our favorite questions that I ask even my

1:03:02.800 --> 1:03:08.400
<v Speaker 1>somewhat special guests, starting with you're still young, tell us

1:03:08.440 --> 1:03:12.280
<v Speaker 1>about your mentors? Did anybody really help shape your career?

1:03:12.600 --> 1:03:15.600
<v Speaker 2>Yeah? I mean the early mentors would have been football

1:03:15.640 --> 1:03:19.480
<v Speaker 2>coaches in high school and college defensive line coach Harold Brantley,

1:03:19.600 --> 1:03:21.800
<v Speaker 2>he was the man like he was. He was actually

1:03:21.800 --> 1:03:23.040
<v Speaker 2>whe who pushed me to the point that I could

1:03:23.080 --> 1:03:25.280
<v Speaker 2>play in college in the first place. And then my

1:03:25.360 --> 1:03:28.840
<v Speaker 2>college defensive line coach Kenny Baker was like I was.

1:03:29.560 --> 1:03:32.240
<v Speaker 2>I came into college playing in a small private high

1:03:32.240 --> 1:03:34.080
<v Speaker 2>school and thought I was And then I got to

1:03:34.120 --> 1:03:36.840
<v Speaker 2>college and just got wrecked for like a good year

1:03:37.160 --> 1:03:38.000
<v Speaker 2>and I was like really.

1:03:37.840 --> 1:03:41.000
<v Speaker 1>Good, faster, stronger, or you just didn't know the game

1:03:41.040 --> 1:03:43.360
<v Speaker 1>as well and didn't have the skills or some combination.

1:03:43.560 --> 1:03:46.240
<v Speaker 2>Like it was like I just had to get better.

1:03:46.320 --> 1:03:48.480
<v Speaker 1>It was like better shape, better skills.

1:03:48.520 --> 1:03:50.480
<v Speaker 2>I needed to get stronger and just be able to

1:03:50.680 --> 1:03:52.640
<v Speaker 2>react to the game on the field way faster. And

1:03:52.680 --> 1:03:56.160
<v Speaker 2>I just wasn't The processing speed and the just size

1:03:56.200 --> 1:03:56.640
<v Speaker 2>weren't there.

1:03:56.840 --> 1:04:00.680
<v Speaker 1>People don't realize that the quality of play at the

1:04:00.680 --> 1:04:02.360
<v Speaker 1>college level, it's astounding.

1:04:02.600 --> 1:04:05.560
<v Speaker 2>We played so we played Alabama, Little Mercy University. We

1:04:05.560 --> 1:04:09.280
<v Speaker 2>played Alabama and Auburn in the same year. I like

1:04:09.400 --> 1:04:12.360
<v Speaker 2>you want to talk about seeing like like like us.

1:04:13.280 --> 1:04:15.040
<v Speaker 2>We almost beat Auburn. We were down seven in the

1:04:15.080 --> 1:04:19.960
<v Speaker 2>fourth quarter, but Alabama Jalen Hurts to uh Mac Jones

1:04:20.960 --> 1:04:24.439
<v Speaker 2>smoked us. They had Calvin Ridley, all Pro receiver who

1:04:24.480 --> 1:04:26.680
<v Speaker 2>briefly had a gambling problem, but he's back as their

1:04:26.680 --> 1:04:28.920
<v Speaker 2>punt returner. Guess who started on the punt team was

1:04:28.920 --> 1:04:31.320
<v Speaker 2>getting juked out of his shoes like twenty times because

1:04:31.360 --> 1:04:35.040
<v Speaker 2>we punted so much. Me But defensive line coach Kenny

1:04:35.080 --> 1:04:38.360
<v Speaker 2>Baker was like, he I worked really hard, and he

1:04:38.360 --> 1:04:40.840
<v Speaker 2>could tell I did, and he was very encouraging and

1:04:40.960 --> 1:04:44.240
<v Speaker 2>that like keep the work ethic up and like you

1:04:44.280 --> 1:04:46.800
<v Speaker 2>will develop, like you will catch up to the point

1:04:46.800 --> 1:04:48.200
<v Speaker 2>that like, if you keep that work ethic, you'll be

1:04:48.200 --> 1:04:50.240
<v Speaker 2>able to play. And he was right. By my third season,

1:04:50.320 --> 1:04:52.520
<v Speaker 2>I was decent, and by my last season, I was

1:04:52.520 --> 1:04:54.440
<v Speaker 2>objectively good. Like I was never going to be an

1:04:54.480 --> 1:04:57.360
<v Speaker 2>All American, but I was like a starter and was

1:04:57.360 --> 1:05:00.760
<v Speaker 2>like a very solid player. But I could easily quit

1:05:00.800 --> 1:05:03.120
<v Speaker 2>and transferred to Georgia and like, you know, done the

1:05:03.120 --> 1:05:05.520
<v Speaker 2>fraternity thing at SEC school, which would have been short

1:05:05.600 --> 1:05:09.280
<v Speaker 2>term more fun, but long term less fulfilling. So football

1:05:09.320 --> 1:05:13.480
<v Speaker 2>coaches post post school, it's funny, like especially with COVID,

1:05:13.480 --> 1:05:15.280
<v Speaker 2>my early mentors were like kind of people I found

1:05:15.280 --> 1:05:17.520
<v Speaker 2>through Twitter. Like I remember when I read The Psychology

1:05:17.520 --> 1:05:19.720
<v Speaker 2>of Money. I thought it was like a very profound

1:05:19.760 --> 1:05:23.640
<v Speaker 2>book and I just like digested everything Morgan house Will published.

1:05:23.920 --> 1:05:26.040
<v Speaker 2>And then a year after that, like I remember when

1:05:26.040 --> 1:05:28.200
<v Speaker 2>he followed me back on Twitter. I was flying from Sevilla,

1:05:28.400 --> 1:05:31.680
<v Speaker 2>Spain to Manchester, England, and I looked at my phone.

1:05:31.760 --> 1:05:33.840
<v Speaker 2>I was like, Oh, this is really cool. This is

1:05:33.880 --> 1:05:35.800
<v Speaker 2>really cool. And then when I moved to New York,

1:05:35.840 --> 1:05:38.040
<v Speaker 2>we like hung out in person at Collob Fund's office

1:05:38.120 --> 1:05:42.280
<v Speaker 2>and like, like great guy, but I would say like

1:05:42.960 --> 1:05:48.360
<v Speaker 2>as a somewhat career slash just aspirational. Him and Tim

1:05:48.520 --> 1:05:51.280
<v Speaker 2>Urban were like my two favorite bloggers from the kind of.

1:05:51.280 --> 1:05:56.280
<v Speaker 1>Like you referenced Tim Urban in the book, but I

1:05:56.280 --> 1:05:59.560
<v Speaker 1>think you referenced a piece of his and I was

1:05:59.800 --> 1:06:04.160
<v Speaker 1>pro you didn't reference the piece on optionality, the so

1:06:04.320 --> 1:06:05.720
<v Speaker 1>to chart with the black lines.

1:06:05.840 --> 1:06:08.120
<v Speaker 2>Yeah, everybody steals it on Twitter.

1:06:08.240 --> 1:06:12.360
<v Speaker 1>I find that piece to be so interesting because you know,

1:06:12.440 --> 1:06:15.880
<v Speaker 1>one of the things about getting old is some of

1:06:15.920 --> 1:06:19.400
<v Speaker 1>your optionality goes away because you don't have Hey, this

1:06:19.480 --> 1:06:21.720
<v Speaker 1>is a twenty five year project. Do I really have

1:06:21.800 --> 1:06:22.680
<v Speaker 1>twenty five years?

1:06:22.720 --> 1:06:22.800
<v Speaker 2>Like?

1:06:23.280 --> 1:06:25.520
<v Speaker 1>What am I going to be doing at age? Ninety.

1:06:25.880 --> 1:06:28.440
<v Speaker 1>All right, maybe a twenty five year project isn't the

1:06:28.480 --> 1:06:31.160
<v Speaker 1>best thing for me or at age eighty best thing

1:06:31.200 --> 1:06:35.760
<v Speaker 1>for me to start. But I laughed at a lot

1:06:35.800 --> 1:06:40.320
<v Speaker 1>of your references because I'm familiar with many of them.

1:06:40.320 --> 1:06:43.480
<v Speaker 1>They were really really good. So so you mentioned Morgan,

1:06:43.520 --> 1:06:46.840
<v Speaker 1>any other post college mentors you want to bring up?

1:06:46.920 --> 1:06:49.720
<v Speaker 2>Yeah, I mean, like i'd say my current boss, Sam Lesson,

1:06:49.800 --> 1:06:51.760
<v Speaker 2>great guy. I mean he's a He's had a very

1:06:51.800 --> 1:06:54.320
<v Speaker 2>cool career, right, Like he like started a company in

1:06:54.360 --> 1:06:57.240
<v Speaker 2>his twenties in Brooklyn, ends up getting acquired by Facebook,

1:06:57.360 --> 1:07:00.880
<v Speaker 2>like had a successful career at Facebook, and then like

1:07:01.080 --> 1:07:03.280
<v Speaker 2>co founded the venture fund I work out now, right,

1:07:03.320 --> 1:07:06.520
<v Speaker 2>and like he's like, it's it's funny. I feel like

1:07:06.560 --> 1:07:08.200
<v Speaker 2>a lot of people in my bubble of like the

1:07:08.280 --> 1:07:11.240
<v Speaker 2>late twenties have this like is this what I want

1:07:11.280 --> 1:07:12.560
<v Speaker 2>to do with my career? You kind of hit this

1:07:12.560 --> 1:07:14.440
<v Speaker 2>inflection point of like you should pick a thing that

1:07:14.480 --> 1:07:18.040
<v Speaker 2>starts compounding, and like his take has always been like

1:07:18.480 --> 1:07:20.560
<v Speaker 2>you should just want to work with like really interesting,

1:07:20.600 --> 1:07:23.320
<v Speaker 2>smart people you respect and like work on interesting problems.

1:07:23.360 --> 1:07:26.960
<v Speaker 2>And that's a pretty good recipe for finding career fulfillment.

1:07:27.120 --> 1:07:28.960
<v Speaker 2>And you know, if a couple of things go right,

1:07:29.000 --> 1:07:33.040
<v Speaker 2>like financial success, but like it's I don't know. He

1:07:33.040 --> 1:07:36.040
<v Speaker 2>he's done like a few different things and now like

1:07:36.320 --> 1:07:39.120
<v Speaker 2>has like an objectively like I like if my lifestyle

1:07:39.160 --> 1:07:40.440
<v Speaker 2>and like life is set up kind of like his

1:07:40.680 --> 1:07:42.560
<v Speaker 2>in my forties, I'll be very cool with that. Like

1:07:42.640 --> 1:07:43.480
<v Speaker 2>so he crushes.

1:07:43.640 --> 1:07:48.320
<v Speaker 1>So you mentioned Morgan's books. Tell us what you're reading now?

1:07:48.320 --> 1:07:49.640
<v Speaker 1>What are some of your favorites.

1:07:49.720 --> 1:07:52.160
<v Speaker 2>So, I I just started reading this book called eighteen

1:07:52.280 --> 1:07:55.400
<v Speaker 2>seventy three. It's I think it came out pretty Yes.

1:07:55.920 --> 1:08:01.360
<v Speaker 1>Who won the Pulitzer for I forgot the name of

1:08:01.400 --> 1:08:05.720
<v Speaker 1>the four central bankers that his first book was about.

1:08:06.040 --> 1:08:08.560
<v Speaker 1>That is literally at the top of my queue, ready

1:08:08.560 --> 1:08:08.960
<v Speaker 1>to get.

1:08:08.800 --> 1:08:12.200
<v Speaker 2>It's how it's I'm about halfway through, and it's it's

1:08:12.280 --> 1:08:14.800
<v Speaker 2>like very good and interesting. I mean the thing I've

1:08:15.080 --> 1:08:16.800
<v Speaker 2>I've done this from time to time, Like I hadn't

1:08:16.840 --> 1:08:18.639
<v Speaker 2>read much over the last year while I was working

1:08:18.640 --> 1:08:18.920
<v Speaker 2>on that.

1:08:19.040 --> 1:08:22.080
<v Speaker 1>Yeah, now I'm writing is a kill you.

1:08:21.800 --> 1:08:25.400
<v Speaker 2>As someone who's written books, I had so underestimated, Like

1:08:25.720 --> 1:08:28.120
<v Speaker 2>I have much more respect for other authors after going

1:08:28.160 --> 1:08:28.479
<v Speaker 2>through that.

1:08:28.560 --> 1:08:31.719
<v Speaker 1>Exactly, can't you read books? You can't blog? You can't

1:08:31.800 --> 1:08:33.280
<v Speaker 1>It just sucks up so much.

1:08:33.120 --> 1:08:35.080
<v Speaker 2>Time with Yeah, it's like all your free time goes

1:08:35.120 --> 1:08:38.559
<v Speaker 2>to that. But something I've always liked is I've always

1:08:38.560 --> 1:08:41.760
<v Speaker 2>been a big biography guy or like certain moments or

1:08:41.760 --> 1:08:45.240
<v Speaker 2>events in history because you can get the chat, GPT whatever.

1:08:45.680 --> 1:08:48.080
<v Speaker 2>People can pull a story together in three hundred pages

1:08:48.120 --> 1:08:50.479
<v Speaker 2>of a thing is so fascinating, and with like eighteen

1:08:50.560 --> 1:08:55.559
<v Speaker 2>seventy three, like reading about the stock market speculation in

1:08:55.600 --> 1:08:58.560
<v Speaker 2>the like Vienna, Austria stock market in the eighteen seventies,

1:08:58.560 --> 1:09:00.280
<v Speaker 2>and then you're just pattern matching that again, it's like

1:09:00.320 --> 1:09:02.840
<v Speaker 2>what I saw with retail investing in twenty twenty, twenty

1:09:02.840 --> 1:09:06.759
<v Speaker 2>twenty one. It's you just see like human behavior playing

1:09:06.760 --> 1:09:09.680
<v Speaker 2>out cyclically one hundred and fifty years ago. Is just

1:09:09.840 --> 1:09:14.200
<v Speaker 2>really really interesting in like a you know, totally different

1:09:14.200 --> 1:09:16.599
<v Speaker 2>time and market and paradigm, but it's the exact same thing.

1:09:16.920 --> 1:09:20.120
<v Speaker 1>Lords of Finance was his first book that won the Pulitzer.

1:09:21.000 --> 1:09:22.880
<v Speaker 1>I'm excited about that book. Any of the books you

1:09:22.920 --> 1:09:23.599
<v Speaker 1>want to mention.

1:09:24.120 --> 1:09:28.080
<v Speaker 2>The Infinity Machine, the one about the DeepMind founders, it

1:09:28.160 --> 1:09:32.320
<v Speaker 2>was by Sebastian Mallaby. I think anyway, it's like as

1:09:32.400 --> 1:09:34.840
<v Speaker 2>far as Ai is now the thing everybody cares about.

1:09:34.880 --> 1:09:37.280
<v Speaker 2>He did a really good job of like like how

1:09:37.680 --> 1:09:39.880
<v Speaker 2>llms even became a thing in the first place, and

1:09:39.920 --> 1:09:43.160
<v Speaker 2>how like this is just group of like British researchers

1:09:43.160 --> 1:09:44.960
<v Speaker 2>who've been holed up in London the whole time kind

1:09:45.000 --> 1:09:48.519
<v Speaker 2>of kickstarted this whole AI boom. And even though Sam

1:09:48.520 --> 1:09:51.519
<v Speaker 2>Altman Elon Musk they aren't like main characters at all,

1:09:51.720 --> 1:09:54.120
<v Speaker 2>You're getting these interesting anecdotes of how like open AI

1:09:54.280 --> 1:09:55.880
<v Speaker 2>came to gather and how there was like a bit

1:09:55.920 --> 1:09:58.879
<v Speaker 2>of a coup with an open AI and then Elon leaves.

1:09:59.320 --> 1:10:01.320
<v Speaker 2>It just did a really good job of framing like

1:10:01.360 --> 1:10:03.280
<v Speaker 2>the current moment in time and how we got here.

1:10:04.160 --> 1:10:05.920
<v Speaker 2>But those are like I read both of those, who

1:10:05.920 --> 1:10:07.880
<v Speaker 2>have been reading both of those in the last month

1:10:07.920 --> 1:10:08.400
<v Speaker 2>and a half.

1:10:08.479 --> 1:10:12.040
<v Speaker 1>They're great interesting. What about streaming? What are you watching

1:10:12.720 --> 1:10:14.479
<v Speaker 1>or listening to give us your.

1:10:14.320 --> 1:10:18.040
<v Speaker 2>Favorite hilariously on the like on the On the podcast front,

1:10:18.120 --> 1:10:20.720
<v Speaker 2>I don't have any shows I listen to regularly, but

1:10:20.760 --> 1:10:23.559
<v Speaker 2>I will selectively if there's like a guest that I

1:10:23.600 --> 1:10:26.599
<v Speaker 2>find interesting for whatever reason. I've like it's everything from

1:10:26.640 --> 1:10:29.400
<v Speaker 2>tuning into like like Josh and Michael on the Compound

1:10:29.439 --> 1:10:34.639
<v Speaker 2>and Friends or like Tim Ferris's show or some Scott

1:10:34.680 --> 1:10:38.160
<v Speaker 2>Galloway stuff. It's I'm so much of a I have

1:10:38.200 --> 1:10:40.720
<v Speaker 2>people who I think are good interviewers. I don't care

1:10:40.760 --> 1:10:43.000
<v Speaker 2>about half the people they talked to, But occasionally they'll

1:10:43.040 --> 1:10:44.880
<v Speaker 2>have someone where I really want to hear that because

1:10:44.880 --> 1:10:48.200
<v Speaker 2>I think they'll pull out good questions, like I don't know,

1:10:48.320 --> 1:10:52.040
<v Speaker 2>Michael Lewis on Tim Ferris really good episode, or it's

1:10:52.280 --> 1:10:55.680
<v Speaker 2>there's nothing I listened to specifically streaming. I did like

1:10:55.720 --> 1:10:58.800
<v Speaker 2>that movie Obsession. I thought it was phenomenal. It was

1:10:58.840 --> 1:11:01.280
<v Speaker 2>the one that like when Megavi out of indie film

1:11:01.280 --> 1:11:04.639
<v Speaker 2>that when Mega viral out of nowhere in it? Who

1:11:04.680 --> 1:11:07.080
<v Speaker 2>directed it? It's the I can't even think of the

1:11:07.080 --> 1:11:09.040
<v Speaker 2>guy's name. He was got to start on YouTube. He

1:11:09.080 --> 1:11:11.479
<v Speaker 2>does a lot of short form comedy. But it like

1:11:11.960 --> 1:11:15.760
<v Speaker 2>blew up and it was the one about the guy

1:11:15.760 --> 1:11:17.800
<v Speaker 2>who like breaks the stick to make the girl like

1:11:17.840 --> 1:11:19.439
<v Speaker 2>he makes a wish that the girl falls in love

1:11:19.479 --> 1:11:22.599
<v Speaker 2>with him and then she goes full psycho. Anyway, it

1:11:22.680 --> 1:11:26.639
<v Speaker 2>went like nuclear on Twitter, Instagram, TikTok whatever, pretty good

1:11:26.880 --> 1:11:29.200
<v Speaker 2>horror film thriller. I liked it.

1:11:29.320 --> 1:11:31.920
<v Speaker 1>Final two questions, what sort of advice would you give

1:11:31.960 --> 1:11:35.400
<v Speaker 1>to a recent college grad interest in the career in

1:11:35.560 --> 1:11:40.040
<v Speaker 1>either writing, content creation or venture capital.

1:11:40.479 --> 1:11:44.040
<v Speaker 2>So my my take on all the career stuff for

1:11:44.120 --> 1:11:46.360
<v Speaker 2>that is, like, I think it's really I think that

1:11:46.439 --> 1:11:48.080
<v Speaker 2>one of the higher leverage things you can do is

1:11:48.160 --> 1:11:49.960
<v Speaker 2>just start a blog and put your thoughts out there,

1:11:50.040 --> 1:11:52.719
<v Speaker 2>even if you have five people reading it, fifty people

1:11:52.760 --> 1:11:57.040
<v Speaker 2>reading it. I think that especially with AI becoming more

1:11:57.040 --> 1:11:58.840
<v Speaker 2>and more of a thing, it's easy to like, like,

1:11:58.920 --> 1:12:03.040
<v Speaker 2>resumes are becoming incre something meaningless, both from like the

1:12:03.040 --> 1:12:05.400
<v Speaker 2>odds of somebody actually looking at your job application when

1:12:05.400 --> 1:12:07.559
<v Speaker 2>you send it in cold or very low, and the

1:12:07.600 --> 1:12:11.200
<v Speaker 2>ability to like lie, like you can make one hundred

1:12:11.200 --> 1:12:13.920
<v Speaker 2>different resumes with LMS based on the job you're applying

1:12:13.920 --> 1:12:15.640
<v Speaker 2>to now versus when I was, Like when I was

1:12:15.680 --> 1:12:18.360
<v Speaker 2>in college, you always tweak your cover letter or resume

1:12:18.439 --> 1:12:20.639
<v Speaker 2>per job, and it's pretty tedious to do that when

1:12:20.640 --> 1:12:23.360
<v Speaker 2>you're doing it by hand. You can make a million once, right,

1:12:23.520 --> 1:12:29.880
<v Speaker 2>So having some like like proof of your thoughts on thing,

1:12:30.000 --> 1:12:32.679
<v Speaker 2>or you've articulated ideas online that show how you think,

1:12:32.800 --> 1:12:35.040
<v Speaker 2>I think, carry a lot more. They've always been important,

1:12:35.080 --> 1:12:36.880
<v Speaker 2>but like stand out a lot more now with AI

1:12:37.560 --> 1:12:41.639
<v Speaker 2>or if you like AI coding assystems are really good,

1:12:41.720 --> 1:12:43.560
<v Speaker 2>like anybody can access them to build stuff. So just

1:12:43.640 --> 1:12:46.840
<v Speaker 2>having a portfolio of like written work or stuff you've

1:12:46.840 --> 1:12:50.360
<v Speaker 2>built online that shows that you took interest and initiative

1:12:50.400 --> 1:12:53.559
<v Speaker 2>and a thing and like put yourself out there super useful.

1:12:53.640 --> 1:12:56.160
<v Speaker 2>I mean. My my take on career stuff in general

1:12:56.280 --> 1:12:58.920
<v Speaker 2>is like if you can go into investment banking or

1:12:58.960 --> 1:13:00.960
<v Speaker 2>consulting right out of on you, it's still probably the

1:13:01.080 --> 1:13:03.240
<v Speaker 2>right move, just from like getting trained on how to

1:13:03.280 --> 1:13:05.800
<v Speaker 2>work hard. People who work at Goldman from twenty two

1:13:05.840 --> 1:13:08.519
<v Speaker 2>to twenty four are typically more competent than other people.

1:13:09.160 --> 1:13:12.160
<v Speaker 2>And for all my stuff about like you should go

1:13:12.200 --> 1:13:15.360
<v Speaker 2>take risk in your twenties, the caveat on that is

1:13:15.360 --> 1:13:17.599
<v Speaker 2>like you should have a couple of prestige STAPs first,

1:13:17.840 --> 1:13:20.240
<v Speaker 2>Like Columbia Business School was a prestige stap for me.

1:13:20.439 --> 1:13:22.599
<v Speaker 2>I enjoyed it, I learned a lot. The main reason

1:13:22.640 --> 1:13:24.439
<v Speaker 2>I went was like I went to a somewhat no

1:13:24.520 --> 1:13:27.000
<v Speaker 2>name undergrad. It's not like I worked at a marquee

1:13:27.000 --> 1:13:29.040
<v Speaker 2>firm out of undergrad. Like you want to get a

1:13:29.080 --> 1:13:33.680
<v Speaker 2>couple of like I have, like somebody's de risked me

1:13:33.760 --> 1:13:36.559
<v Speaker 2>as an individual. Then you go take the shots that

1:13:36.600 --> 1:13:40.360
<v Speaker 2>you want to, so like I it's like have a

1:13:40.360 --> 1:13:42.920
<v Speaker 2>collection of like independent work and thoughts like you can

1:13:42.960 --> 1:13:46.439
<v Speaker 2>share like in real time. And then I think it's

1:13:46.479 --> 1:13:48.920
<v Speaker 2>important to get one or two prestige STAPs before you

1:13:48.960 --> 1:13:50.439
<v Speaker 2>go jump off and do your own thing.

1:13:50.680 --> 1:13:52.920
<v Speaker 1>And yet in the book you talk about what a

1:13:53.240 --> 1:13:58.800
<v Speaker 1>what a misfocus it is hyping on status and why

1:13:58.840 --> 1:14:00.600
<v Speaker 1>that whole game is so cheah.

1:14:00.640 --> 1:14:04.519
<v Speaker 2>So the status thing's so nuanced. I think that if

1:14:04.560 --> 1:14:07.120
<v Speaker 2>you treat status as an ends to itself, you're going

1:14:07.160 --> 1:14:09.639
<v Speaker 2>to be incredibly disappointed. I think if you treat status

1:14:09.640 --> 1:14:11.680
<v Speaker 2>as a thing that you can acquire and leverage to

1:14:11.720 --> 1:14:14.200
<v Speaker 2>actually do ease to an end. Yes, like if the

1:14:14.280 --> 1:14:17.280
<v Speaker 2>trade is I'm going to go to an incredibly competitive

1:14:17.280 --> 1:14:19.559
<v Speaker 2>school and spend two to four years working in some

1:14:19.680 --> 1:14:23.479
<v Speaker 2>version of like Goldman, Blackstone, McKenzie, whatever, and I can

1:14:23.520 --> 1:14:26.719
<v Speaker 2>come out of that and do anything that's very much

1:14:26.800 --> 1:14:28.920
<v Speaker 2>worth it. But you don't want to be the person who,

1:14:29.280 --> 1:14:32.120
<v Speaker 2>like ten or fifteen years into their career never really

1:14:32.160 --> 1:14:34.640
<v Speaker 2>figured out their things. So kept chasing status is like

1:14:34.680 --> 1:14:39.479
<v Speaker 2>a vanity projects. It's like I say, status as diminishing

1:14:39.479 --> 1:14:42.160
<v Speaker 2>returns or like once you have enough of it, it

1:14:42.200 --> 1:14:43.840
<v Speaker 2>gets marginal. After that, you're good.

1:14:44.280 --> 1:14:46.439
<v Speaker 1>And our final question, what do you know about the

1:14:46.479 --> 1:14:51.320
<v Speaker 1>world of investing today? Might have been useful back when

1:14:51.360 --> 1:14:54.280
<v Speaker 1>you were locked in your bedroom trading specs.

1:14:54.520 --> 1:14:58.240
<v Speaker 2>I underestimated how much retail investing is like a permanent

1:14:58.280 --> 1:15:01.719
<v Speaker 2>fixture in the market today. I think it compounds from

1:15:01.720 --> 1:15:04.160
<v Speaker 2>like and this is all like public market stuff, but

1:15:04.240 --> 1:15:07.519
<v Speaker 2>like pod shops, trading, quarterback, quarter are like more and

1:15:07.560 --> 1:15:09.559
<v Speaker 2>more of a thing. Passive investing is more and more

1:15:09.600 --> 1:15:13.120
<v Speaker 2>of a thing. You could argue that true, like price

1:15:13.200 --> 1:15:16.479
<v Speaker 2>setters being like fundamental long short funds or and like

1:15:16.560 --> 1:15:19.000
<v Speaker 2>long only mutual funds are less of a thing. So

1:15:20.080 --> 1:15:21.760
<v Speaker 2>it's created this thing where you have like a lot

1:15:21.800 --> 1:15:25.040
<v Speaker 2>of like very short term trading on like whatever, alternative data,

1:15:25.120 --> 1:15:27.680
<v Speaker 2>quarterback quarter data, and then you have a lot of

1:15:27.680 --> 1:15:30.000
<v Speaker 2>passive stuff and then a really big active group is

1:15:30.040 --> 1:15:33.519
<v Speaker 2>like retail investing is a thing like game stop. I

1:15:33.520 --> 1:15:35.719
<v Speaker 2>thought was a one off fluke. It wasn't like open

1:15:35.760 --> 1:15:39.040
<v Speaker 2>door short squeeze out of nowhere. You're seeing like random

1:15:40.120 --> 1:15:43.479
<v Speaker 2>companies will just pop off like five percent, which makes

1:15:43.479 --> 1:15:45.720
<v Speaker 2>it like Dan Sundheim was on a podcast with the

1:15:45.720 --> 1:15:48.880
<v Speaker 2>Collison Brothers, the Stripe founders. A couple months ago, he

1:15:48.960 --> 1:15:51.000
<v Speaker 2>was talking about how they changed, like how they position

1:15:51.160 --> 1:15:54.800
<v Speaker 2>their shorts now d one capitals, because you just you

1:15:54.840 --> 1:15:57.519
<v Speaker 2>could be fundamentally right, but guess what, fundamentals don't matter

1:15:57.560 --> 1:15:59.400
<v Speaker 2>if the borrow rates through the roof and the stock

1:15:59.479 --> 1:16:02.160
<v Speaker 2>like eight and you get blown up right, like like

1:16:02.439 --> 1:16:05.760
<v Speaker 2>ask the game the Melvin Capitol guy about fundamentals when

1:16:05.760 --> 1:16:08.080
<v Speaker 2>his fun got blown up right like it. At the

1:16:08.160 --> 1:16:09.559
<v Speaker 2>end of the day, the only thing that matters is

1:16:09.600 --> 1:16:13.120
<v Speaker 2>making money. And I really thought a lot of that

1:16:13.200 --> 1:16:15.120
<v Speaker 2>was a twenty twenty twenty twenty one thing and it

1:16:15.160 --> 1:16:17.720
<v Speaker 2>was COVID and people were at home. We're seeing so

1:16:17.840 --> 1:16:21.680
<v Speaker 2>much stuff with like random speculative like nuclear reactor. Like

1:16:21.680 --> 1:16:24.200
<v Speaker 2>a company Akalo went public through a spack. It was

1:16:24.240 --> 1:16:26.360
<v Speaker 2>like a Sam Altman backed company. It was worth like

1:16:26.360 --> 1:16:29.160
<v Speaker 2>forty billion dollars. I don't think they have a functional reactor.

1:16:28.840 --> 1:16:33.280
<v Speaker 1>Yet, Like, are you suggesting that sites like Reddit, Wall

1:16:33.320 --> 1:16:37.240
<v Speaker 1>Street debts still carry the influence they used to or

1:16:37.280 --> 1:16:39.519
<v Speaker 1>has that attenuated and then it's spread out to die?

1:16:39.960 --> 1:16:42.200
<v Speaker 2>I would argue that they almost carry more weight because

1:16:42.240 --> 1:16:44.640
<v Speaker 2>I think that, like really, I think there's this is

1:16:44.680 --> 1:16:47.280
<v Speaker 2>pure speculation, but I think that they're now increasingly a

1:16:47.320 --> 1:16:50.960
<v Speaker 2>thing that like call it like institutional traders, quant funds, whatever,

1:16:51.000 --> 1:16:53.280
<v Speaker 2>we'll like look at as a data source where if

1:16:53.320 --> 1:16:56.000
<v Speaker 2>something spikes on one of these sites, they'll play the

1:16:56.040 --> 1:16:58.519
<v Speaker 2>momentum and like it makes these bubbles go even further

1:16:58.520 --> 1:17:01.920
<v Speaker 2>than they used to. And everything happens so fast now

1:17:01.960 --> 1:17:04.240
<v Speaker 2>because like the speed that information moves on the Internet

1:17:04.360 --> 1:17:07.800
<v Speaker 2>is just instantaneous. That like a bubble that might take

1:17:07.880 --> 1:17:10.040
<v Speaker 2>like months to build up and then collapse could happen

1:17:10.240 --> 1:17:13.160
<v Speaker 2>within a week both ways. So it's just like the

1:17:13.479 --> 1:17:18.200
<v Speaker 2>whole like internet spread of information faster and faster. It's

1:17:18.200 --> 1:17:21.040
<v Speaker 2>all all derivatives, like retail investors getting in the market

1:17:21.120 --> 1:17:24.839
<v Speaker 2>and then yapping about stuff online. That's just never gonna stop, right.

1:17:24.720 --> 1:17:27.320
<v Speaker 1>And it's so funny because everything old is new again.

1:17:28.200 --> 1:17:32.040
<v Speaker 1>Back in the day of the Yahoo message boards, like yeah,

1:17:32.240 --> 1:17:36.799
<v Speaker 1>like iomega and and that sort of stuff, nothing has changed.

1:17:36.880 --> 1:17:39.200
<v Speaker 1>It's just how much faster were.

1:17:39.120 --> 1:17:42.600
<v Speaker 2>And it's like zero commissions. Now it's like the there's.

1:17:42.600 --> 1:17:44.559
<v Speaker 1>And it's in your pocket, you know how let me

1:17:44.640 --> 1:17:46.280
<v Speaker 1>go home and call my broker does it?

1:17:46.320 --> 1:17:48.240
<v Speaker 2>And now there's like, oh we have prediction markets and

1:17:48.280 --> 1:17:50.880
<v Speaker 2>sports batting on your phone. We have removed all friction

1:17:51.160 --> 1:17:54.040
<v Speaker 2>from people putting money at risk to do stuff, and

1:17:54.080 --> 1:17:54.759
<v Speaker 2>we've made.

1:17:54.600 --> 1:17:57.080
<v Speaker 1>Regardless of how dumb or speculative it might.

1:17:56.960 --> 1:17:58.800
<v Speaker 2>Be, and the speed of which you can communicate what

1:17:58.840 --> 1:18:01.800
<v Speaker 2>you're doing is now all so instantaneous and free. So

1:18:01.880 --> 1:18:05.120
<v Speaker 2>you just have people constantly going risk on on whatever

1:18:05.560 --> 1:18:08.400
<v Speaker 2>for whatever reason, and then everybody else knows it. That's

1:18:08.479 --> 1:18:10.920
<v Speaker 2>just that's only going to keep accelerating.

1:18:10.880 --> 1:18:13.800
<v Speaker 1>Under except it kind of sounds like a very late

1:18:14.280 --> 1:18:16.080
<v Speaker 1>stage bullmarket.

1:18:16.200 --> 1:18:17.840
<v Speaker 2>Could have said that in twenty one and we were right,

1:18:17.920 --> 1:18:20.360
<v Speaker 2>twenty two is kind of a bear market. Then AI happened,

1:18:20.360 --> 1:18:23.200
<v Speaker 2>So it's like I think that. I just think market

1:18:23.240 --> 1:18:26.519
<v Speaker 2>cycles in general will keep happening faster and faster because

1:18:26.680 --> 1:18:29.240
<v Speaker 2>it'll collapse, people get blown up, and then somebody starts

1:18:29.320 --> 1:18:31.599
<v Speaker 2>running another thing. I just think it's going to get

1:18:31.640 --> 1:18:32.400
<v Speaker 2>more and more violent.

1:18:32.880 --> 1:18:36.439
<v Speaker 1>I have a pet thesis that the giant reset, the

1:18:36.520 --> 1:18:41.240
<v Speaker 1>giant fiscal stimulus and crash and recovery in twenty twenty

1:18:41.720 --> 1:18:43.880
<v Speaker 1>was like a reset and extent of the bullmark, and

1:18:43.920 --> 1:18:48.280
<v Speaker 1>another I agree with that ten years it's but anyway, Jack,

1:18:48.320 --> 1:18:52.439
<v Speaker 1>you you were more than a somewhat special guest.

1:18:52.600 --> 1:18:52.920
<v Speaker 2>Thanks.

1:18:52.920 --> 1:18:56.280
<v Speaker 1>This was really great. Thank you for being so generous

1:18:56.320 --> 1:19:00.000
<v Speaker 1>with your time. We have been speaking with Jack Rain's.

1:19:00.080 --> 1:19:03.120
<v Speaker 1>He is the author of Young Money, a field guide

1:19:03.120 --> 1:19:06.920
<v Speaker 1>to wealth and purpose in your twenties. If you enjoy

1:19:07.000 --> 1:19:10.280
<v Speaker 1>this conversation, well check out any of the six hundred

1:19:10.320 --> 1:19:13.960
<v Speaker 1>and fifty three we've done over the previous twelve years.

1:19:14.000 --> 1:19:19.479
<v Speaker 1>You can find those at iTunes, Spotify, YouTube, Bloomberg, or

1:19:19.520 --> 1:19:23.759
<v Speaker 1>wherever you find your favorite podcast. I would be remiss

1:19:23.760 --> 1:19:25.880
<v Speaker 1>if I didn't thank the crack team that helps us

1:19:25.880 --> 1:19:30.720
<v Speaker 1>put these conversations together each week. Alexis Noriega is my

1:19:30.960 --> 1:19:35.559
<v Speaker 1>video producer. Sean Russo is my researcher. Anna Luke is

1:19:35.600 --> 1:19:40.040
<v Speaker 1>my podcast producer. I'm Barry Rutoults. You've been listening to

1:19:40.160 --> 1:19:43.680
<v Speaker 1>Masters in Business on Bloomberg Radio.