0:00
Does Stanford need another entrepreneur club? Absolutely not. Right. Right.
Does Stanford need another entrepreneur club? Absolutely not. Right. Right.
So, so I'm like, let's just look at the existing landscape.
Let's infiltrate, extract the best individuals, recruit those agents, so-called, and then add the most immediate value.
Not that we're trying to take them away from the scene that they exist in, but intro them to 20 other, 30 other delusional people where that delusion is coraled and the delusion becomes reality.
The willingness to give up early just astounds me.
People who judge a single outcome are really doing themselves no favors.
Everybody thinks that's so like you're you're all over the place. What are you doing? Find a niche. Dive deep, right? I don't know.
It doesn't really make sense to me.
If you look at a lot of these top companies that are being built, they're all built by these polymaths. Well, hello everyone.
It's Jim Onessy who Tommy basically said, "How the [ __ ] are you so high energy?"
And my answer was because I get to talk to people like Tommy Potter.
Tommy is a polymath, an amazing guy who we discovered not too long ago.
And my chief of staff met him and he called me on the phone.
He goes, "Jim, you absolutely are going to love Tommy.
You got to have him on the podcast."
That almost never happens.
So already Tommy, you're very special.
You are currently at the University of Michigan doing a selfdesign degree.
You got bored with high school because you thought it was all basically [ __ ] I agree.
Uh but then you went to Austin and and got a better uh thing going there.
You are the head of power hour. I love this.
The CIA for entrepreneurship, highest signal society for it for college kids in the world.
Tommy, please tell me you are not running a new version of MK Ultra. I hope not. I hope not. Welcome. I appreciate it, Jim. Thanks for having me.
It's a pleasure to be in your presence and in your orbit.
So, honestly, going through uh all of your accomplishments at such a young age, first off, very impressive.
Um, but let's kind of start at the beginning.
Um, let's give me your origin story.
I I know that you've been hustling since you were five, you know, lemonade stands, selling Girl Scout cookies.
I love seeing that because what one does when they're young often is a good indicator for what they're going to turn out like as adults.
Uh but give us give us the origin story.
Yeah, I don't I don't think my my sisters necessarily deserved those those badges.
I think I was I was the one going door todo.
Um but uh yeah, I think even even Nick and I talked about this um that it was kind of the there there's that uh orange orange dot which in like Don Lowry's uh like framework of of color personalities and it's that athlete.
It's that person that kind of just is a spontaneous adventurous um and like the competitive drive to win.
Um and I think that's always kind of been innate for me.
Um hence Yankee Candle, you know, fundraising and such.
Um, but yeah, I think it it all kind of transpires uh from like a small town uh Molen, Illinois, like John Deere headquarters is my backyard.
Um, so it's nice to have a Fortune 500 company in in the middle of nowhere.
Um, and then uh yeah, from like 12 to to 18 was completely, you know, competitive golf uh around the country.
Um, and I love to kind of look for that uh exceptional, not to say that was exceptional on my end, but exceptional uh talent that isn't related to building whatsoever.
Um, in in young, you know, entrepreneurs and founders, um, trust masters, Olympiads in math, etc.
I think that exceptional talent kind of directly translates over um to exceptional building and exceptional passion.
Um, but yeah, that was like from 12 to 18, you know, major major golf uh, every day.
um a lot of time on the course.
Um and then uh yeah, for the latter half of high school went to uh the University of Texas um online high school and that was a way I think online high school was even more hands-on than inerson high school.
Um and I'm sure this might be a little little a little topic that we should probably discuss because I'm I'm curious even your thoughts on these kind of rudimentary systems and industrial uh age systems.
Um but yeah, I I never saw the the value in 8 hours of of school, um 5 hours of homework, um and then not much left to to do much much else.
And uh I I think many people don't take action to actually get out of that system, um that you're kind of indoctrinated into.
Um but in instead, for me, I I was like, let's let's move.
Um let's get the hell out.
And uh yeah, online high school was for me.
I started like building solar houses in my living room, studying the pH levels of my of the Mississippi River in the backyard and and um was even more hands-on I think than in in normal school.
Um and you kind of start to see these alternative schooling, you know, it's kind of starting to pop up.
Stanford's online high school, UT kind of the top one and two.
Um you have Ad Astro with Elon Musk and kind of his new school.
Um, Sandbox is even another one in college where they'll allow you to build um and and people in Utah churning churning YC companies.
It just kind of shows like are these builders in Utah? Not necessarily.
But if you give the time um and allocate the time and resources to to builders and just letting them build, you'll you'll get into some pretty interesting accelerators and build some pretty good companies.
Um, so I think that's kind of where where it all kind of begins is this Charlie Munger inspired theory to kind of learn a lot about a lot of things transferring into Michigan now.
Um, creating my own degree in and business psychology, philosophy and polyai, very very humanentric.
Um, and love learning people.
Um, and uh, yeah, now that kind of brings me into uh, saying yes a lot freshman year.
Um I I had this theory that um being nonlinear would give you 100% success.
I'm I'm curious your thoughts on that.
But uh it random nonlinear stories seem to always prove true and almost if you can purposefully live very random very nonlinear um I'm curious if I'll be successful with that.
Um, so whether that's from ARV, our immersive media research, some some like investment analysis and publishing pieces there, uh, over to like co-developing the the space entrepreneurship curriculum with a good friend from Michigan and, uh, and then moving into like filming a documentary on homelessness in Ann Arbor for 3 months.
Um, everybody thinks that's so like you're you're all over the place. What are you doing? Find find a niche. Dive deep, right? And uh, I don't know.
It doesn't really make sense to me.
I think uh if you look at a lot of these top top companies that are being built um even the even the top you know five and and fortune 500 right now um they're all built by these polymaths these people that you know learn a lot about a lot of things.
What's the quote um um master master of none jack of all trades master of none right but then second half of that quote is oftentimes better than a master of of none.
Yeah like so wow a lot to go on there.
Uh we'll get to high schools in a bit because I completely agree with you.
They were designed by industrialists essentially with the marching orders.
Yeah, we need uh you to train people to sit placidly for 8 hours, follow instructions, and do it without complaining.
And voila, you got your public high school system in the United States of America.
And you know we whenever you change the dominant um kind of zeitgeist of an era you see it ripples out and it's not just one segment it's all of society. Right. Right.
What few people understand is the change from like the age of monarchies to the age of uh democracies the age of uh you know scientific inquiry etc. That was rough.
They had a little war, you know, called the Napoleonic wars because uh the old system was collapsing, the new one was emerging.
And uh everything needed to be changed.
And sometimes you can do it just right as I think uh the American uh founders managed to do.
Sometimes you can take it way too far like our friends in France with the reign of terror.
But what comes out on the other end is a completely reordered, reconfigured system, right?
And we are still in kind of the death throws of the industrial era, moving into the era, I hope, of abundance and people having a lot more choices in their life.
But cultural lag is a real thing and it takes a while to reorder stuff.
We invest in a uh offshoot of ad Astra called synthesis schools which does AI tutors for math and soon to be other subjects.
The results you really can't debate them when you look at those kids and what they you know you take kids who you know self-reported hating math uh and make them love math and not only love math but be really good at it.
it becomes pretty evident that the alternatives are going to ultimately be the new way of doing things.
But we're going to have to do a lot of pushing and a lot of rooting for that type of stuff because, you know, stasis is is rough.
It uh you know, but that's the way we've always educated our kids.
Well, yeah, it doesn't work.
Trying to install a correct answer machine in young minds, I think, is laughably idiotic.
And what we should be doing is say, "Hey, Tommy, figure it out, man. Show me.
Show me what you're thinking about.
You should have a lot of free time to explore, to do all of that kind of stuff."
We'll get to that in a bit.
But I'm also was really interested on the golf angle because you turned down a lot of internships, you know, traditional internships because you wanted to be a caddy in the Hamptons for rich guys.
te tell tell me what was driving your thought process there.
Yeah, I mean I I'm not one for formal program programs as you can probably tell already.
Um and so freshman year most people will just kind of flaunt, you know, different ideas out there, maybe go back home, maybe maybe do an internship, right, if you're if you're lucky.
And for me, I think uh there's this amazing book called The Third Door.
um unsure if you read it, but uh and and I' I've always loved being able to back door into circles that I'm not supposed to be in.
Um and for me that would have been the the Hamptons, obviously from a small town, not my usual scene, but had some good golf background um and some experience there.
So, uh kind of cold email 200 real estate agents um to find me a place to stay in in a woman's basement.
And uh for 90 days uh it was like 12 hours catting um 2 hours kind of playing pickle ball with their wives, 2 hours chauffeering them around in their Range Rovers at night.
Um and this was a way that I think I realized instead of just building a relationship with some of these kind of important people um that that be in the Hamptons um I was able to rapidly expedite some of these relationships over multiple contexts and multiple settings.
Um because if you just have a working relationship, right, um it's not as great as, you know, maybe when you see them drunk or maybe when you you kind of see uh maybe their family, um kids, you know, wives, etc.
Um I think that expedited some of the relationships and I was able to, you know, very very hedge fund, very real estate, I think, group of people out there.
Um but but it was a very unique 90-day experience.
It was actually directly after the homeless documentary that I filmed. Wow.
So, one week in between and it was bottom of 1% of America, top of 1% of America and that was an insane kind of switch.
Um, and a kind of a surreal six months overall.
Um, but yeah, I was able to kind of get into a decent club out there and and it was a it was a it was a good time.
There's a great book you might like.
It's old, so it might seem antiquated by but it's by a British guy named Steven Potter called OneUpsmanship.
Um, and uh, I suspect that there's a lot of that going on out on Hampton golf courses.
There's another one uh, by Paul Fouseel called Class, which is would speak directly to your experience from going from the bottom 1% to the top.
He his theory is he's wickedly funny.
Uh Paul and his theory is that what he he he doesn't do traditional classes like you know there's working class, middle class, upper middle class, right? Rich, etc.
He he he has a much uh more uh detailed uh group of classes.
But the joke is as you get to the end of the book, he he says that what he calls the top out of sight, right?
Those are the folks you were with are identical to the bottom out of sight.
And then he goes through all the ways that this is true. Hysterically funny.
It's like normal people very rarely see them.
In the one hand, it's because, right, they're living behind walls on huge estates and on the other one, they're they're lost somewhere in the streets.
Um, but let's let's dive right into that.
Like, did you notice any similarities between the uh the homeless people that you documented with your documentary and those rich folk in the Hamptons?
Yeah, I I think I think you're hitting, you know, it perfectly.
Um, a lot of people have asked this kind of what's the takeaway from those two groups of people.
Well, I think we're very similar.
Um, and and many people have problems on different levels. I'll say that.
Um, whether it's I I can't get a shower to have an interview for a job or it's all the way up to my Wi-Fi on my beachfront property um is not working.
And I hate it when that happens.
frantically running around the course for three holes.
Um, calling calling your your IT guy to to kind of get it fixed before you're home.
Um, and and stopping play on the course for a little bit.
Like, yeah, I think I think we all have problems, but on different levels.
Um, so, uh, yeah, there there are some interesting similarities that I did find and and that was definitely definitely one.
Um, but yeah, it's a it's a unique little bubble in fantasy land and one that I think um I don't know if if it's right to say obviously these people that we just don't know and are kind of unheard of um you kind of have the face of America and these celebrities that everybody thinks kind of uh whether that's you know run America and and pull these puppet strings but I don't think in reality that's true um and and kind of saw that vividly. Interesting.
Uh, keeping on that theme, there is an old movie starring Dudley Moore called Arthur in which he plays the son, the narrwell son of one of America's richest families and he's a drunk and everything's a joke to him and everything.
And so finally his family forces him into rehab and he's there with a bunch of regular folks, right?
And they're all attacking him and they're like, "You're just a drunk just like the rest of us."
and he looks at them and he goes, "That is correct.
However, the difference is I'm a drunk who knows exactly where my next drink is coming from." What did you find?
What were your observations about about those rarified circles? Like what'd you learn?
Did you if anything good and bad?
I think I was ignorant to think that they would care about a 19-year-old.
Um cuz I I I I think I really did think that they would they would care that, you know, I I hustled my way into the circle, right?
Um but in reality, I think it's that I was um spilling coffee on on people that were, you know, more likely to give me a chance, right?
And that was that was the whole point.
You're bumping into the right people maybe at the right time.
And I think it's a lot of a lot of the time you have to be in the wrong place at the wrong time in order to be in the right place at the right time.
And yeah, I think uh the the circles that you're you're surrounding yourself in there and to be able to maximize that and and and that can kind of be, you know, extrapolated outside of the Hamptons itself.
Um go go to the coffee shop next to Sequoia headquarters if you're raising, you know, for your for your uh for your startup, right?
like find the clicks, find the equinox cuz you might stumble into a better founder there.
You know, there's different circles that you can kind of manifest into that would hopefully give more chance for more opportunity.
Um, and so that would be kind of the the generalized theme, I think, of of going going to the Hampton specifically.
Um, but yeah, I don't think these people necessarily cared um sometimes, and I I was ignorant to think so.
And so you really start to you start to understand that you have to pitch yourself in like two sentences.
You get two questions is kind of what I realized over time. You get two questions.
They they ask you, you know, maybe where you from, where you go to school, what are you doing out here, right?
And then if they like you a little bit or there was some sort of connection maybe with Michigan or like from Illinois, they might follow up with, okay, you know, where where do you want to where do you want to go and you know, what are you going to do with your degree? Something like that.
And I I learned over time over the, you know, the the maybe the first month that the only way they could help me is if I said that I wanted to be in their shoes.
And so I started to to kind of illustrate that I I wanted to be right where you are, sir.
You know, blank blank, you know, Mr. uh Mr. insert name.
And then light bulb, hey, I can I can help this help this kid.
M and so I don't know if it's uh not authentic to not illustrate your your means um specifically, you know, but I I think that that was a way for them to maybe assist me if I wanted to hopefully be in their shoes one day.
And something I kind of learned as you start to get your one sentence pitch down, um that's all you get.
That's all the time you have.
Um but uh but yeah, it it was it was unique. It was wild.
I want to go back, but I think the ROI is on on some other adventures, too. Yeah.
Well, you know, between a yes and a no, there's always a maybe.
And that's why persistence helps, right?
Because uh you can't tell till you ask.
Um I I I think it's interesting from another perspective like I don't golf um because like my father golf was a religion to him and so I was he you know according to him I was a really good natural golfer.
But I I kind of did realize that my mom for many many years was a golf widow, right?
Because at least in the summer, I grew up in Minnesota, so uh you know, she uh had him around during the winter.
Uh but during the spring, summer, fall, he was always out on the course.
Um, but I think it it it seems to be an artifact of an older age to me at least because and I'm going to get in trouble for saying this, but like a lot of rich people I know are really [ __ ] boring and they're they're not like they like I really prefer the the kind of crazier. You got energy, Jim. You got energy.
Whacking around a ball doesn't make sense.
I I guess have you ever seen the movie Catty Shack? Of course. Yeah.
I would have been Chevy Chase in that one.
Like if I had to play golf, I'd tried blindfolded and all that kind of stuff because like chasing what did Mark Twain not say?
Everything that everyone say like very rarely is a quote from Twain actually from Twain.
I've gotten to the point where I actually try to have our AI find it in the actual book.
Uh but uh I think he might have actually said this one.
Golf is a good walk spoiled.
Um so it's also a great book itself too. Yeah.
But um you know I think golf can also be I think one of the reasons why it is uh so many very successful people like golf is it's a great environment to have a casual conversation which oftent times leads to hey why don't we do that deal together or whatever and so I do find that interesting.
I'm really fascinated also.
What motivated you to make the documentary about the homeless people?
And then I also have a question about that.
What what if what if a documentarian followed you around for 90 days?
What what would they what would uh the viewers see that would maybe conflict with your public persona? Yeah, very interesting.
Um the reasoning for the film um it's actually really interesting.
Uh my good friend was a senior.
I was a freshman and the we were very busy people.
Um the best way to be friends and and kind of learn your friends even more is to do a project together.
You're forced to spend time together. Yep.
Um we were very curious people.
We were walking down the street one day and um we see we see a homeless folk and we're like, "What's life like at 2 p. m.?
What's life like at 2:00 a. m.?
we only see the the 4-se secondond panhandling.
We always look the other way.
If anything, I always thought we need to lean into their stories even more because they are failed stories um that often have very teachable um and kind of great learning outcomes that I think at least some of them.
We partnered with uh with five folks that cared to in that sense partner with our journey and were willing to, you know, roll around 90 days with with a with a camera and we were in 10 communities at at at 2 a. m.
seeing how these people lived in the forest all the way over to abandoned industrial buildings that they were living in and trespassing in.
um and uh and and film some of that with heroin needles on the floor and going into this kind of dark room that was uh a little a little dangerous.
Um, I don't know if my parents were too fond of of the the adventures I was going on for um, I mean, you know, a couple months there, but uh, you know, 7. You're doing what?
What are you doing, Tommy? The 7 a. m. breakfast.
We tried to see all of the emotion, all of the thrill.
Um, and and no, we weren't just like putting a camera on the on these folks and we were trying to assist them in a way.
Um, and I and at the end, you know, it's the philosophies of the streets documenting their journey.
um and and some of our people were successful to escape.
Um I think the best way for me to actually convey homelessness um and we we went into this film specifically thinking that there was some sort of um inflection point like homeless now reasoning is because of blank.
There was there was no there was no point.
Um, and we realized that kind of halfway through that each reasoning was, you know, I think I think of homelessness as a 30-story building and you're born on said level, say 15, you know, 20, 25.
Um, homelessness is is this compilation of series that, you know, you you miss a paycheck, you're you get in a car accident, you you missed work once, you're out of a job, and it's this step by step by step, right?
All the way down to rock bottom, ground zero, right?
But then, you know, I was always thinking they're jumping out of the window window.
They're they're coming down, you know, very fast and it's kind of that one thing.
But no, they they finally get to rock bottom level by level and soon enough they can't take the elevator.
they have to take the stairs.
The society is kind of and then there's grease on the stairs and then there's it's a struggle to kind of walk back up um and and climb your way out of the society that's very much stacked against you.
Um and so that's I think the a little interesting analogy that we kind of figured out along the way.
Um but yeah, very very much thrill of emotions um across it all.
some successful people get in apartments, help them get like a Planet Fitness membership to then have a shower, have a place to go, maybe even work out to then get them that interview, to then get them that job.
And that's all it really like almost like a shower was literally all all it t all it took um to kind of get the boost.
Ironically, all it takes is a shower.
It it was it was odd that it's something maybe that simple.
Um but but yeah, unique unique experience.
Have you read Chris Arnad's book on the back row kids? It's called Dignity. Don't believe so.
I'm going to write that one down as well.
It's really interesting because he is a photographer.
He's an old Wall Street trader who retired and took up his love of photography and walking.
And uh his book Dignity, I had him on the podcast when I just started the podcast.
And one of the things that he pointed out to me that really resonated with me was that he went in thinking, "Jesus, man, there are all of these programs, right, food stamps, food assistance, public housing, etc.
Why do we have this problem with homelessness?"
And he goes, "I figured it out when I befriended and talked with them that most of them were absolutely horrified by having to go as the supplicant to whatever bureaucratic busy body uh was overseeing the dispensing of said benefits, right?"
And and so he was like the the these are oddly very proud people and they would kind of rather be homeless rather not take the assistance if if the opposite it means that they have to comply with some petty bureaucrat uh and their kind of power grab over them. Did you see that? Very much.
Um food was not an issue at all.
there's two or three free meals.
Everybody thinks we actually did, you know, interviews on the streets with just some some random folks to say, you know, what what do you think?
You know, why why are people homeless?
Um that was a common answer and it's not an issue at all.
There's plenty of of honestly food to go around.
Um there's plenty of systems.
the voucher program to get a house was actually some people waiting nine months um in line and if they didn't if they weren't at 2 am on the 31st with their with their with their person to check in they're bounced off the list.
We had one of our folks 8 months in and gets bounced off because they they they were not not on time and they didn't show up or like were a day late or something like that.
Um yeah, I I think also people very much mentioned that they you have to be very um I wonder if this actually relates to to founders now that I think about it, but shameful um to to be sorry shame shameless to to to be uh panhandling.
Many of them were very uncomfortable that very first time to ask for things.
to ask for things. And I think you're kind of hitting the point where to go ask from a bureaucratic system for something um to to be handed something like they wanted to earn it but you you it's very hard to earn something at that at that level um similar to founders and you get to be very scrappy and it kind
of converts into going door to door being told no however many times right and so yes I think you definitely see um wanting to kind of pick up your own bootstraps and and get going but it's it's very hard to do so um so I definitely think there's like a a a pride issue there and like responsibility issue there. Um but yeah,
Um but yeah, there's honestly a ton to unpack and and kind of all this this is it also even a crisis, right?
Can you can you call it a crisis if only you know not only but you know in terms of population?
I think it's just just around 600,000 people are homeless.
It's a lot of people in terms of the population.
There's there's other things to to do with money though.
Um I think when you have a lot of a lot of people um struggling with an issue and and in terms of a percentage is that a crisis, right?
Um another thing to kind of think about.
So So now let's turn the camera on you.
We're going to follow you around for 90 days and make a documentary about you.
Uh what are we going to learn about you that might conflict with your public persona? Yeah.
Um, I think it's I think it'd be very hard to show complete true colors.
I think you try to be um as honest and as forefront with with whether that's actions or words.
Um, and uh I sometimes think back to the only maybe true self is the family group chat. Can you be more true?
And actually one guy was trying to make a startup around the family group chat and biometrics around being able to have access to the family group chat, you know, in your bloodline.
Um, really interesting concept, but uh, but you know, I don't know if you can really be true.
I don't know if I could be completely transparent in all things that I do.
Um, and and like I guess live stream or or maybe build that documentary around me for 90 days.
You know, you hope your actions are the same, but I I I would think otherwise.
My friend uh Ron Howard made a movie called Ed TV a long time ago, and that was the premise.
The premise was they were just going to film him.
Unfortunately, it came out at exactly well almost exactly the same time as the Truman Show. Yeah.
Which uh did a little bit better.
But you know, I if I'm right, if my memory is correct, persona is actually the Greek that leads to personality, right?
But a persona is almost by implication your public face, right?
Like TS Elliott had a great line in one of his poems where he says that he's preparing his face to meet the faces that he meets.
This idea that like essentially everyone has a mask, if you will, uh that they give to the public, right?
And they uh the worry there, of course, is that you come you become what you consistently do.
And and so uh I've always been very fascinated by that because like part of freedom to me at least is to be as absolutely close to the way you actually are just in real life, right?
And and and so those are things that come often with uh some challenges, right?
because as you mentioned, shameless.
You've you've got to be uh you've got to be um very willing to disagree with other people in social settings where you know the the norm would be being polite.
I I maintain that you can be polite and disagree at the same time. Um it's an art form.
Um, but I I I think that you're right.
People when when the cameras get trained on you, it's like, uh, you know, and now obviously some people are natural performers um and and others aren't.
Uh, but I I wonder like what did what did you learn from making the documentary uh about the way you approach founders with Power Hour?
I first want to hit on like the the masking and and I I think about authenticity.
Um and so the the masking aspect I I wouldn't necessarily go completely against you, but I think that is very much how I've lived to I'm not a filmmaker, but I guess you know a portion of my life did do you know you know you know allocate some time toward a film.
Um, I wouldn't call myself a filmmaker, but now when I come in contact with a few close friends that are in film, I have a piece of myself to resonate in that conversation.
Now, do I emphasize that like right now a little bit more than I probably should be? Yes, I do.
Um, and and I I wonder if if that's, you know, some people say, you know, I'm masking, you know, I'm I'm playing a role that isn't true to myself, but I think it's the whole point of living this random story, this very Yeah. Yeah.
But see, I would differ I would differ with you there.
It's you're not masking anything.
you made the [ __ ] movie.
I mean, like you did have that experience.
So, and I love your point about authenticity because like I've had a lot of people ask me, "Yeah, but can you coach me and kind of teach me how to be authentic?" No, I can't do that.
And and where do you think that come from?
Comes from do you think it comes from fear?
from like the worry that other people are going to laugh at you.
I mean, it it it seems to go away, at least in my experience, as you get older.
Uh, you know, when you're young, you are heavily into socializing.
And I think that's from our evolutionary past, right?
Because we lived in tribes.
And what do you want to do in a tribe?
You want to fit in because if you don't fit in, they exile you and you die.
fit in, they exile you and you die. So you definitely want to fit in and that seems to be younger people are that vibe is very strong but as you get older you realize you know other people aren't thinking about you at all honestly
they're thinking about themselves for the most part and and so it gets easier you should exactly right Wallace Wallace Waddles quote I don't know if you've read much of him but I have actually he's wonderful the the science of getting rich I could talk about that with you for for a little bit of time. It's kind of my Bible to live by and uh
It's kind of my Bible to live by and uh add more value to the world than you collect and and you know the the only thing you can do for yourself or sorry for this world is to be to make the most of yourself is his kind of quote that you know there there is no other reason to live. Absolutely.
to live. Absolutely. And you know that's the it is not at all selfish to fix yourself first because you got to and the only way to do that is to be as introspective and honest as you can be and that's hard sometimes right like a
lot of people are like there's a great quote from Jed McKinna where uh he's quoting Socrates and says you know the unexamined life is not worth living and he goes I think most people would have a really hard time even examining that statement much less their own lives, right? And and there's this notion that
And and there's this notion that we kind of come into this world, no owners manual for human OS.
And yet there are tons of shrink wrapped systems that you can just sign on to, right? Oh, okay.
This religion was the one I was born into. Cool. I'm doing that. I'm going that way.
I'm going to do that whole thing.
And to me, that was just never an option, right?
It was always like, well, [ __ ] that.
I mean, I'm not interested at all in that.
When when you are trying to recruit people for your CIA power uh hour, like what do you look for?
What what kinds of traits stand out?
And you're like, "Ah, okay.
This uh man or woman is going to fit in really well."
Yeah, there's there's a lot to to touch on here.
Um, and I think specifically you have a lot of people vetting on I would think of it in terms of a graph on like y intercept, right?
And this current credibility and this current established um knowledge base or or kind of status symbols on a on a LinkedIn resume or something like that.
Um, and and I always wonder, um, as I kind of call it, people, you know, collecting these Infinity Stones, people that, you know, kind of be able, you know, scoundrel up maybe two or three nice brand names.
I wonder if the first one [ __ ] up, right? Yeah.
you question their their ability to maybe directly source the right person and then that compiles on to the next name and the next name and then everybody's giving this name to a person that maybe didn't deserve it.
And so sometimes you have to question all the way back and it's very hard to do so because you're like they worked there, they worked there, they have they went through this.
Um, and so I think that's where it comes to the rate of change is what I love to see.
And and so less less y intercept, how fast and the slope at which they're moving.
Um, and and less brand names, but give me more give me more of what you've built, what you've done.
Um, weird exceptional talent in the past like chess master, uh, uh, Olympiad in in in math.
um exceptional musical composer.
Um diving into things that are very curious and and less related to building itself in any any in any form.
Um I I don't really care if they're if they're like designing fashion, you know, it's something that is very very deep and can directly translate over to be deeply building and learning into into their company.
Um, and so then the last thing that I I I kind of search for, which I'm not sure if many communities do, um, is the culture dynamic and culture fit.
You kind of have these two types of founders.
The [ __ ] founder over to, you know, whether that's Travis, right?
I think you mentioned Steve Jobs on some other podcast like these people that are phenomenal um, yet aren't fit for a community probably, right?
And so I always joke that jobs would have been voted right off the island first thing, you know, you wonder, right?
And so although we we praise some of these people, um, and you look for those people with a chip on their shoulder, many, you know, venture capitalists do, um, are they a fit for the group?
Um, and are they, uh, you know, the the quote being like, you know, all all boats rise with the tide.
um that's one that you you kind of search for someone that's elevating the lives of others, the founder that is more uniquely passionate rather than that has the chip on their shoulder.
Um and so the culture and personality fit within the group I think is very important to continue sustaining that community.
Um and so the way I guess my my group operates is is less on applications. We don't churn cohorts.
um we don't we don't have applications.
The CIA model is actually very interesting.
I'm not trying to make some secret society.
Um it's more about the model in which I've kind of studied with them.
Um and uh and how they don't have necessarily, you know, a branch and office in Ann Arbor here.
They just have a couple agents, right?
and you go to, you know, you go to each each system and ecosystem um and you see does Stanford need another entrepreneur club? Absolutely not. Right. Right.
So, so I'm like, let's just look at the existing landscape.
Let's infiltrate, extract the best individuals, recruit those agents, so-called, right?
And then add the most immediate value to where, you know, not that we're trying to take them away from the scene that they exist in, but um intro them to 20 other 30 other delusional people that are um are where that delusion is coraled and the delusion becomes reality is kind of how I've thought of it.
Um, and so, you know, when you're sourcing, I think what does delusion mean?
Uh, it's it's to me it's like high self-efficacy, the the ability to have high, you know, high self-worth and understanding your capabilities. Um, high self-respect.
I think if you have one of those teetering, you're like looking at like a psycho killer if you're on one spectrum and then like a person that you don't want to be around.
So, make sure you have both.
Um, but then, uh, I think the delusion aspect is someone who, uh, believes they're capable.
um you know more than they actually are.
Um and that's where the sense of delusion something that they actually are trying to attain that is is not even you know possible in their realm but as you put those people together there they'll you know the selfworth kind of boosts up and and that delusion hopefully yeah can become reality.
Um, so I think that's that little section on the graph that I'm looking for.
Um, and people um, and and we're hoping, you know, we we find them rather than churn churn some applications and a bunch of cohorts.
They're supposed to supposed to be one community that lives on.
Everybody asks who's going to be my who's my predecessor?
Who's going to who's going to operate this once you're graduated college?
And I'm like, why why do I have to be done, right?
Why do I have to I I'm going to put, you know, some time into this for a few years and then I'm just I'm just going to be moved to a different section of the platform and now I'm going to be an adviser or an alumni and I'm going to be set off in the dust in the corner and I have to be tapped on a new tab in order to see my name.
Like to me that doesn't make any sense.
Um and I I hope for this, you know, and and the people within this group um can just continue on in this whether I don't even know if I'll recruit, you know, so-called recruit afterward, you know, after a few years.
It might just be 37 people, you know, for for for the rest of, you know, I guess our lives.
And maybe companies at 30, maybe we build companies at, you know, 35.
But it's just it's just the the right people that are within the group.
So Dan Tops Tapscott said, "Your network is your filter."
And so maybe we're trying at OSV to scale that a little bigger than you are with Power Hour, but I think you're absolutely right about that.
And your environment plays a really big role with how you're vibing.
And like they've done study after study after study that literally introduce one turd into the punch bowl and nobody's going to drink the punch bowl, right?
and and people can people's energy uh enthusiasm commitment all those things uh authenticity uh can bring up an environment like several quantum leaps uh and then the naysayer the ah that'll never work uh but like and I'm not saying that we should be polyianish we shouldn't we should always be [ __ ] things up and and learning from that like oh okay we really [ __ ] that up.
Let's let's fix it from what we learned.
And I love the delusional thing because um I I I myself don't uh say that's what we're looking for, but the number of times when I was starting a company that those near and dear to me said, "Jim, you are delusional."
Uh was uh very very many.
And just like recently, I had a good old friend from high school.
We caught up when I was back in Minnesota and he's like, "You know what I love about you, man, is like you just decided you're gonna start a film company, production company, oh, a publisher, too, and uh new media.
You have no experience doing any of that, Jim."
And I'm like, "That's right.
That's why I'm really excited about it because I get to learn and because I'm not burdened by the that's the way we've always done it here, right?
And I think that's the beauty of of your group similar similar to ours that it's this isn't just one CS group of people and very technical talent.
Um, and you see a lot of those groups and societies and and all these like brand names that you go through this accelerator, but it's only for technical people.
Um, we have like, you know, a guy that has like seven million followers.
We have a guy who's maybe um laser physicist, AGI researcher, like a deep marketer 10 plus million in you know in revenue at age 20, right? Folks declining Doge.
Like it it's all over the spectrum because that's where I think these new ideas, these diverse perspectives come in rather than just one person being praised within that hierarchial system because they've had the most, you know, money raised, most traction, most results.
Um and and to me that person isn't receiving um they're only giving uh some advice, right?
When you're kind of at that top, but that CS kid might not know a damn thing about how to personal, you know, a personal brand, how to package themselves or maybe storytelling, things like that.
We actually we actually had that happen at the last fall.
We had all the fellows that uh we uh give out through OSV uh gathered here in Connecticut and uh a highly technical scientist who was building an athome uh device where you could uh basically test your baby's poop and make sure that there weren't pathogens or whatever in it.
sat down with our now uh officially named uh CEO and editor and chief of Infinite Books, Jimmy Sony, and pitched him on what she was doing.
And I was kind of in the earshot and I was listening.
I'm like, "Oh, that's cool."
And I kind of went to a different group.
And then she found me like an hour and a half later and she goes, "I cannot tell you how happy I am that I had that last hour and a half."
She goes, "I learned that I knew nothing about pitching people who were into the doing things this way, etc."
And Jimmy essentially listened to her in terms of what she was trying to accomplish, who her target market was, all of that, and gave she had been just focused on the science, right?
And gave her like an entire marketing plan.
And one of the things that I'm a big believer in is cognitive diversity, right?
Like I'm crap at many many things.
And I'm not saying that those are not important things.
I'm really shitty at some really important things.
Uh so having someone on my team that is really good at that, it it it helps very very much.
helps very very much. um generalist specialist I think here even the cross country to I was just recently kind of going campus to campus cross country and finding the most intelligent and talented individuals at each of these campuses um SF Boston New York City went over to Canada to water UIC mission and and and so what's really interesting is that
what I saw on the east coast and how that is kind of different than the west coast I think these bubbles have have different DNA you have your your long-term you a researcher over at MIT that is very I think of it as like a calm lake just pure technical talent that is very long-term very um I'm going to research for 5 years and then I'm
going to build and they're very adamant about that you start to see maybe the flip side in the Harvard maybe entitlement which I don't think is bad I think that's a ne negatively conoted word but entitlement can be good especially in this founder world and then you move over to like SF where there's people getting getting a capital allocation for you know barely having an
MVP but they have all the right founder DNA um and So, it's really interesting to kind of see these different different groups of of people and and the different bubbles of the these uh the you know we want to talk about you know being being you know the your your friends or your closest um the some of who you surround yourself with. I guess
I guess that quote um is kind of who you are.
you can kind of easily see in those in those bubbles um how people kind of are are whether that's growing up or you know you even think about you can choose your friends but you can also choose your college you can probably choose your friends um you can you choose the former a lot easier than than college but I think some of these college
campuses have a type of person or persona you want to be around uh maybe a reason why you go to college unsure but and and where are you finding the most talent one of the things that we're going to do is we're going to put somebody into the field full-time, but I've sort of expressly said to them, don't go to Stanford. Everyone's already
Everyone's already there.
Like, we're not going to find anything there.
Uh I want you to go to second, third tier universities.
Uh because there's, I bet, a ton of diamonds in the rough there.
And uh so but our strategy is very similar to yours which is why Nick was excited uh when he met you because we we are also going to give that person uh who is roaming for our venture division check writing authority or wiring authority or you know Dogecoin authority whichever you prefer where they can literally write a check up to $10,000 to somebody that they find incredibly promising.
Uh but you got to you got to go looking is is my opinion. It's low ego. Most firms won't do it.
Um it's manual labor and and it's low of many firms, many many GPS to to actually put that effort in because not to say they want uh all these people to kind of gravitate towards them and all the the applications to be booked through their portal.
Um, but I think it slightly diminishes the brand.
Um, to be going campus to campus to have some like popup shop, some event, right?
Um, I think you can do it in a manner that doesn't necessarily diminish the brand, but instead um, having access, I mean, being being available, I think, is a huge why be closed doors?
Um, and so it's kind of a different way to feel about the firm.
Um, but yeah, definitely a low ego play, but I think it's obviously the right play to to find.
Well, I'm I'm very lucky because I don't have LPs, so I don't have to justify any of that to them.
And and I just it just seems very like I know you admire Charlie Mer.
He had this great joke about this guy who's in a uh a fish lure shop and he's looking at these really fancy lures and he can't make up his mind and he walks over to the counter and he says to the guy, he's holding up a couple and he goes, "Do fish really like notice the difference between these things?"
And the guy looked at him and he goes, "I don't know. I don't sell to fish.
So it's like you know the the the obvious the obvious you know acolytes or right college all of that sort of stuff it it will give you a a significant advantage in the beginning right says the guy who barely graduated from a state school University of Minnesota.
Um but it it diminishes rather rapidly based on what you actually do. Right. Right.
Um so you also those campuses Waterlue. Yeah.
Not to say it's like a second tier or anything.
I think it's phenomenal school and a lot of talent, but I don't think it was on many people's radar until recently. Yeah.
And and that's been one that's you know been churning a ton of amazing technical talent. Yeah.
And McGill is the big uh name brand up there in Canada.
So we probably won't we probably might go to McGill, but we'll definitely go to Waterlue. Oh, is great.
You also though use which attracted my eye because I sort of built a career on building algorithms to help me decide things.
Uh you use uh Elad Gills Elgo after you've met people. Talk about that. Walk us through that.
That's actually how I source um for people.
So yeah, that's partly this like manual game um on the ground, but that only gets you so far.
Um and so we we've in like a week and a half um we'll run our eighth national retreat um for 20 builders, no phones, no substances for 72 hours.
And that's and that's one thing that when I when I ask people um and invite them on this kind of all expenses paid retreat and treat them as such exceptional people.
I ask them for maybe one or two people um that you'd recommend and heavily vouch for that are you know after I say I've been you know cross country finding the most exceptional people you're one of the 20 um find me find me one or two that if we have some room at the end I'll I'll allow them in.
Um, and mainly that's a play to find, I think some people have called it a weirdo broker.
Um, and that we're all around the, you know, these weird people. Um, I'm weird.
I have some weird friends.
Um, and and some of these people aren't very public online, so you can't always get the content play.
Um, but they have friends.
Um, and so that's been a way and and Elad's way of of uh of hiring talent.
You hire through the close people you trust and then you ask for their close referral.
Um, so that's completely why I don't have applications.
It's completely referral-based.
It's completely through the three best friends and their three that goes to nine that goes to 27.
You can kind of scale up fairly decently and find a boatload of amazing people um just through, you know, establishing some credibility and some trust and providing the utmost value to those individuals and then them referring you, you know, a person or two.
Um and then they they can be the reason for the the connection.
So what has gone in in groups that you've run?
What has gone exactly as you expected it and what has gone ex exactly the opposite of what you were expecting?
I don't know if I necessarily try to have expectations.
It's one of my huge thesis on on kind of whether that's building communities or running events in general.
Um, I I think there's a like having an itinerary I'm completely bearish on because for what reason do we have to move to the next activity and kill the current beautiful moment that we're in because it's 9:00 Jim, we have to go to the next activity.
You and I would get along at these things, right?
And very similar to when to when Nick came out, like I I didn't know what the hell was going to happen.
I think the success is putting the right people in the room um and that's about all there is.
So um when you put um 20 people in a room, let's say, if a few people are on their phones, if you have to mandate no phones, I've been starting to think about this with my retreats.
If you have to mandate no phones, um instead act act with uh the group and see if they pull out their phone, then you know you've failed, right?
because you can just be an observational user uh on that side to see why did that person get on their phone?
They're probably not fit for the group.
They're not engaged in the people that I've brought to the retreat or they're not engaging themselves.
They're not, you know, you know, highly intelligent themselves to to go deep on a conversation with some of these intelligent minds that I've brought. So, that's on me.
Um and that's the the the the fault that I must have put um in in the group.
Um if you want to call it that, you know, kind of one turd in in the in the group like that kind of diminishes.
Maybe that's a negative infin infinite loop. I'm unsure. Right.
Um but yeah, I think that's that's one thing that I I try to not have expectations with how an event is run or or how a retreat is run.
Um I don't know if I had any expectations coming on the podcast.
Just have a good conversation.
Hopefully the two intelligent minds um that are hopefully brought to the table can can speak um well with one another.
So that that's how I usually operate most of these events so-called um is mainly through serendipity less less itinerary and it uh is a great sorting mechanism as well because um as you point out right like people seem to have this hostility to learning
via negativia and your point about them pulling out the phone that's learning through negativia right like I I I I couldn't agree with you more that some of the best of those sessions that we've had no agenda other than hey just show up. Um and we'll see what happens. It
Um and we'll see what happens.
It seems to me that that also selects for people who have a lot of courage.
I think that that is often overlooked and and maybe even people will use different words, right?
It's like no no no I'm not courageous, I'm obsessed, right?
I'm obsessed with making this and and bringing this into the world.
But I definitely think that to put yourself out there takes courage, right?
Like it it is you're willingly going and putting your work, whether you're building a company, whether you're writing a book, whether you made a movie, whatever.
like you're showing it to people who might make really hostile and uh derogatory remarks about it and and so courage is one that I'm always very interested in.
Um, the ability to pivot is another one that I think is really important because I agree with you that like if you think that you're going to have some linear plan that is going to get executed with militarylike precision, you are deliluding.
Well, then you really are diluted because what you got to do is, you know, you're either going to succeed or learn, not fail, right?
like, "Oh, I failed and now I'm gonna just throw all my chips away and I'm done."
And like the the willingness to give up early just astounds me because like 80% of things that I look at, hey, that shows really great potential.
Hey, whatever happened to that book you were writing or that podcast you started?
and and just like the the people call or Annie Duke is a friend of mine.
She she was the champion poker player and she's doing a lot of consulting now around things like you know h how to look at the world in terms of taking a much longer view right and she calls people who judge an outcome are a single outcome are are really doing themselves no favors. Right?
It's what you should do is look at the process, not the necessarily the outcome.
If you So, for example, if you and I got together and we had a really dumb idea and we thought, "Oh, let's give it a try." And it succeeded.
If we're the type that makes our plans by the result of that one isolated outcome, we're going to get really [ __ ] because it might not continue to succeed.
What you want to do is look at the underlying process. What has surprised you?
Um, and I know you don't go in with an itinerary.
I know that you are very open-ended about it, but what uh give me a give me a session where you like were at the end of it, you were just like, "Holy [ __ ] I never expected that that would happen."
And you were just absolutely supercharged by what happened.
It's It's every time, right?
Because you put the right people hopefully in the room.
hopefully in the room. There was this one time uh you know we're sitting at the top you know the top of an apartment building um for for like you know hangout um I don't know maybe 20 people 40 people showed up and you kind of see
at the beginning who maybe are some of the ones that not are transactional but are there to quickly stop in say hey aren't there much for the group maybe there for themselves right and the ones that stick around and you're there four five six hour. It's It's 2 a.m. We're on It's It's 2 a. m.
We're on the couch talking about philosophy, which government's going to win, anarchy, neoliberalism, and and I remember that, you know, specifically this one time, I think it was 4:00 a. m.
, and I was like, "Guys, I got to go.
You know, I got class at 9.
Like, I got to get out of here. You guys continue.
Let me know which government wins, but uh but I got to run."
And many people think, "Oh, you're not starting.
You're not talking about startups.
You're not talking about the next idea." Of course not. um that's not the point.
Um because where we're challenging each other's opinions, beliefs, um and that's where I think a lot of progression is.
Um it's almost a time for us to not even think about the next best company.
Of course, we love our feedback on maybe progress that week or give us an update, but honestly, I might have a co-founder in the room here in, you know, in the next month, um that I I've just really enjoyed getting along with um and because of that want to build a company with them.
I think that's one like very vivid example.
Um, and a lot of that happens.
It's it's the deep philosophy talk on the couch after, you know, good subset of of of four, five, six hours of of a conversation and perusing the room.
Um, but soon enough, you know, you're not talking about startups anymore.
Um, it's usually the huge success point.
Is is are you finding that there is kind of a dominant philosophy among these types of people?
Uh, you mentioned, you know, which government system is going to win.
Um, I I'm I'm I'm intrigued by that.
Uh, I think that was just a way for people to go against each other.
Um, and necessarily maybe something they believed, but they researched it and were like, you know, I don't necessarily believe in neoliberalism, but yeah, I'll fight this one.
You know, I know, but let give me give me the reigns. Let me go.
Um, and so I don't I'm not sure if there's necessarily a specific government or belief that I could kind of give it to you, but uh I think a lot of these people are very very not headstrong.
Um, but they're very intelligent and they can they can argue aside very well and and they have that athlete in them to try to be competitive and win.
M that you know that's one of my theories that it's actually harder to get a super intelligent person to abandon a no longer useful mental model.
And the reason behind that is because because they're so smart. Guess what?
They build iron ironclad narratives around why that particular mental model works and they've thought through all the arguments and they have an answer for every one of them and and so they chess players Jim. Yeah. Absolutely. Absolutely.
and and and so I I've always found it really uh an irony that some of the brightest people are the ones, you know, because they link that with being headstrong, as you put it.
Um, and they're like, "Yeah, well, it continues to work for me no matter what you say."
And I'm like, "All right, that's good."
Another Jed McKinna quote that uh I love uh because it happened to me.
The smartest thing I ever did was stop being smart.
Um, and being much more open to uh like I never thought about it that way.
Let me see how that works.
Um, every conversation as if that person is superior to you in some way.
Very similar to the homeless documentary, why you approach someone in that circumstance because they they do have something to teach you.
Um, if anything, those people have more to teach you than some others.
Um, and I think that's, you know, very much the superiority that you hope to give to another person in their, you know, wisdom that they have.
You even touched on a little bit a little bit ago dilution and dilutive.
Um, I think a lot of these communities, they they think it's really awesome utility in the tagline to be the largest entrepreneur community at Harvard.
I I laugh at that and completely turn the other way when I see it.
Um because that's that's another issue in these communities.
The the talent bar isn't high enough.
The high curation isn't there.
Um and and and the and that's a main flaw because as we talked about it's a negative loop because the people won't come back.
I how I always measure this is if I have one amazing individual um now not you know we're all amazing in different ways.
ways. I think these people as you know they all have different deep expertise but if you search for that one person that if if this person had a conversation with them would would they be tuned out right would there not be a value on both sides and that's usually how I go about put these two people one-on-one is there value ad with kind
of your maybe more intelligent person or or person you respect hopefully the most within the group and that's how I think you can vet people as well on a very case-byase basis um instead of having to say like, "Oh, this person looks great on paper and and and has a lot of things I really like conversation." No, put
No, put them put them with your other person that is is is really hard to maybe have conversations with.
Are they going to are they going to thrive? I think that's tell.
And if you start to question, it's probably not a fit. Yeah.
Either you got to be all in or or if you're second guessing and is he worth it? I I don't know. You know, probably out.
One of the things that I was lucky to have happen in my life is uh my main career being in public markets.
And if if you know there's an old saying on Wall Street, there are old traders and bold traders, but there are no old bold traders.
And and what what I took away from that is if you need to learn some humility, and I certainly did when I began my career, you'll get it by being completely trashed by Mr.
Market time and time again.
And what you realize very quickly is if you think you're right and the market thinks you're wrong, who's usually going to be the winner of that battle? Good.
So, you have humility forced upon you, right?
Because like you've got to be willing to go from genius, idiot, genius, idiot, genius, idiot, because that's the pattern.
And it also really helps you inure yourself from like people being really nasty about you.
um when you're doing poorly, then the long knives come out and then when you're doing really well, they often the same people will say, "Oh, you're the best. This is great."
And it's just very amusing to me.
You you have you've you've had experience in investment analysis and and let's talk a little bit about that.
Just going to ask you actually.
I'm curious since you turned more venture. Yeah.
Or not more venture, but turned into venture itself. I'm curious.
I I've seen some people that love being very liquid like hence some Hampton's people that I catch up with in New York and they're like I love the liquidity the the direct immediate maybe return that I can get investing compared to the 7 to 10 year.
I'm curious what you think like why turn into to venture if maybe you know public market markets was your was your previous you know main career was it was there a love in the game for the immediate liquidity over to maybe a 7 to 10 year outlook and kind of having your money all you know you know scrunched up in in a company for maybe a little too long and that and that didn't feel I'm curious just your thought process around that. Yeah. So, um neither.
Um the what drew me to Wall Street was I looked at it as the Olympics of business.
Like you got to know a ton of [ __ ] about a lot of things to do really really well in public markets.
And I felt that there a lot of people were doing it completely wrong. Right.
And and this is back before quants were a thing and before algorithmic investing was a thing.
And I thought, well, you know, everyone seems to be making their decisions based on their uh view on like the CEO or the chief marketing officer or anything like that.
I think that that's really dumb when you get to be a public uh company, but it's not really dumb when you're dealing with private companies.
So, very very different there.
And that led me obviously to quantitative algorithmic style investing in public markets, but we started doing private investing in probably 2006.
Uh just because I was very intrigued by what you're all about.
I was very intrigued about because there's a really big difference between the personality and emotional profile of the CEO of a Fortune 500 company and a founder of a uh you know company that might not even have an industry yet, right?
like this person over here who's climbed the ladder to become the chairman of the said Fortune 500 company often might make a horrible founder because the skill set is very different right and that's why you sometimes inflection points come along Jobs again being the exception here right like he probably when he got fired was not the right guy to be running Apple at that particular time.
He needed some time in the wilderness and he got it right and uh went and did next and oh I don't know Pixar but he he he needed that time I think to get seasoned to go to be able to go back to Apple and say okay here's what we got to do to survive in it's just a very very different personality profile skill that etc.
in public and private and I just wanted to explore hm all right like that seems to be pretty evident let's see if that's true and what we're finding is yeah that's very true um and and plus we just have a ton of fun doing it right we know we know the success rate is going to be small and that's fine um you know we we conceivably have learned a lot more from the total bombs that we invested in than the ones that, you know, went according to plan.
First off, nothing goes according to plan.
Um, and if it does, it's an accident, right?
And and often times we find that if it's going way too close to plan, either they're not dreaming big enough, either they are, you know, it and then so we'll come in and say, you know, uh you don't you think we should maybe push a little harder here?
And they'll look at you like I'm doing everything like all of the milestones.
And we're like, okay, but like you're kind maybe you're accomplishing them too easy.
So very different kinds of investing.
Love both kinds because at the end of the day, it all comes down to we humans, right?
And and like in public markets, I always say the last arbitrage left is arbitrageing human nature, right?
Like all quant study, we we all use the same data, right?
One of the things that I was doing at Oshanosy asset management before we sold it was building out other data sets uh just to see if there was going to be a huge difference. Right?
Everyone uses Compostat and um you know their data has been audited.
It's what I would use to write what works on Wall Street.
It's what all the academics use. And guess what?
If you kind of scratch the surface on quantitative public market investors, their models look very very similar because they're using the same data and and so it just got a little dull.
And at the same time, machine learning was coming online and I'm like, aha, we have new ways that we can do this type of investing.
But that just led me much more deeply into that world.
And you know then we ended up selling the company.
We didn't the company wasn't for sale.
Uh they came to us not the other way around.
Um but then we kind of thought well cool we'll we'll have an opportunity to do the things that are fascinating to us right now.
Um, you know, so the way I look at it is life's an adventure and you shouldn't worry too too much about if you get a destination change.
Um, you you I I I see a lot of people and it's this is not necessarily a function so much of age but of disposition.
Like a lot of people just live on cruise control on autopilot and I try very hard not to do that.
Um and when you don't Yeah.
a lot a lot of [ __ ] that happens, you know, you ideally wouldn't have planned for that to happen, but you always at least I always seem to find something a nugget in that like, oh wow, okay, I've got to upgrade this model that I'm using because I haven't, you know, executed right here.
But it's all ultimately it all comes down to us, human OS, human operating system, and I'm fascinated by it.
And so when you're fascinated by that and you can arbitrage it like why why on earth did we start a book publishing company?
Well because I've written four books. I love books.
I read a ton of books and the current legacy system is broken and there's a huge amount of arbitrage uh in that uh industry.
So, let's try to arb all those inefficiencies away.
It's I I joke that, you know, legacy publishing companies are using best practices.
The only problem is they're from 1925, not from 2025.
And so, when I see things like that, I just get really excited and like, oo, we get to make this a lot cooler.
Um and and so I think that um you've got to be just very very open-minded in your approach to finding these things that are going to you know what who was that woman uh that was po popular for one hot second?
She was always going on about sparking joy.
I don't remember her name, but like for a while uh there that like every tweet was but does it spark joy?
Maria Kundas I don't know.
Well anyway um what tell me a little bit about what motivated you to do these investment analysis reports?
um very much thought it was the initial path kind of kind of way back investing since I was 12.
Dad's in the business, sisters are in the business.
Um and kind of was uh definitely dinner table talk.
Um and so yeah, started to write.
I really enjoy kind of the both cross industry analysis is actually really really fun to me.
actually really really fun to me. very very uh very you know fundamental investing um on my side but published some good pieces that you know got like 300,000 views um and things like that I started looking at with the GLP drugs and that impact maybe on the Lululemon right or or the difference like in in
the Gen Z kind of shift with now Celsius and a new way of energy drink so get away from Monster but all all the all the people want to drink healthy ier if you know what does that make sense but right you know there there's a great marketing shift there and and that's what I I love to kind of analyze um more
the maybe slight contrarian perspective as well being I just feel slightly contrarian myself with always trying to run against the grain um but a lot of that investing style um is very uh is very cross-industry and and now for the most part my my investing is kind of two times leveraged poor a bought in um to
the right companies very very much Tesla, Palunteer and Nvidia um are are are where my kind of current uh continual investments and and play the uh the long-term game on double double leverage shares and a lot of people think I'm very very risky with that but what billionaire was ever made not being risky. They all say diversification but
They all say diversification but I don't think that's how you made your money sir.
I have a really good friend because I was on the soap box for a long time about trying to get people to understand that deterministic thinking is a relic of Aristotle and Arisatilian logic where it's yes, no, you zero 100, etc.
And and we were together in Manhattan and he's like, "Jim, listen, you got to get off this trying to convince people to be probabilistic thinkers."
And I'm like, "Sid, why would you say that?"
you say that?" And he goes because if every if it was normally distributed if if appetite for VA or risk was normally distributed we don't exist there are no us because it would become an efficient market like and I'm like that's a really good point and I love studying people
because it's all emotion I mean that that's the whole point of the study people as well because I thought you know I might I might go into you know investing route still might you know and that's that's how I loved learning emotion and we're the ones moving the market, not for the most part. I mean,
I mean, sure, there's some, you know, plenty of computer computer algorithms out there moving markets, but mainly it's people.
Um, and so I thought, learn people, learn learn emotion, learn greed, learn fear.
Um, and it's really hard to to buy and sell at greed and fear, even though that's what you're supposed to do.
Um but uh well you know Sir John Templeton who was a legend in investing in public markets uh told the story about how he made a practice of putting in uh price limited orders on stocks that he loved way below the what price they were trading at.
And people would say to him, you know, Sir John, why why do you do that?
And he goes, "Because I know that if it ever gets to that price, I will not have the guts to pick up the phone and tell him to buy." Yes.
And so he was aware of his own fragility and like, "Okay, I guess I got to game this out and do it a different way."
It's absolutely hard, right?
Like I think the thing that I was most proud of for my career in public markets was that I never overrode one of our models emotionally.
And that people kind of look at me strange when I say that, man.
When you're in the at the the center of a great financial crisis and people are literally taking $200,000 in cash and putting it in a safety deposit box, it takes a lot of [ __ ] guts to say, "Back up the truck. We're doing it. We're buying it.
We're not overriding because, you know, we we are hyperbolic discounters.
That's part of our nature.
And like right now, what's happening right now, we we extend that as far as the eye can see into the future and think that it's always going to be happening that way.
And it's like the worst way to think about things.
You know, talk about first order thought being a a real limiting factor to the way people tend to do things, but like when you're emotional, like the amygdala takes over.
The prefrontal cortex, no contest, man. It's a knockout.
The amygdala is meant to be there at rare moments when you're really in danger.
We didn't get that memo from evolution, right?
like, "Yeah, guys, you're no longer being chased by saber-tooth tigers here.
This is uh not the same situation."
The brain doesn't know that.
And it's like, and you previously talked about negativity, too.
And how we're we're apt as humans to kind of gravitate on it.
It's because of that survival type fight orflight mode.
To totally we are we love the media when when someone which car accident happened, which you know, which shooting, right?
It's like where we gravitate toward this type of of news and all this negative media and then and then you hope to not have maybe hence the podcast negative infinite loops because of it. Right. Yeah.
And you know we are we are optimized to pay very close attention to novel dangers and that comes to us from evolution and it [ __ ] a lot of people up for life.
It's like you you want a simple way to calm yourself and get rid of that brain fog, stop watching TV news.
And if you can like stop reading the the most what I would call popular news sources.
I have one on my phone that's called the paper and it was basically just the facts. Here's what happened.
No editorializing like this happened.
This happened, this happened, this happened.
And you know, it's it it is difficult for people because we love drama. We're hooked on drama.
And like the, you know, look at the look at the anti-hero and some of the greatest shows are anti-hero shows.
Breaking Bad, you know, like it's brilliant stuff.
And so we, you know, it's it is easier to entertain with that kind of dark [ __ ] than, hey, guess what?
Another 7 million people left poverty over the last year.
Like that is the true underlying thing that is going to transform the world.
And yet it's like people yawn.
It's like, oh well, yeah, that's good.
But hey, did you see that fight over there or you know what's going on?
And it's it's even even on this like similar similar topic to kind of all the the hedge fund uh kind of talk we or like just investment talk we've kind of been having.
I I've always found it interesting on the occupational status that has kind of been over the past decades of of like back in the 70s, you know, you're a doctor, you move 80s, it's the lawyer, the IB in in maybe the '9s, moves over to like 2000s and you're looking into like consultant hedge fund and then 2010s, right?
You know, you're like venture capital, but then all these venture capitalists are now going to be entrepreneurs and builders now like into 2020.
And so I' I've always seen this like shift over interesting decades over and I know you're a big fan of history.
Um, and the fact that there's now 32,000 plus uh venture capitalists when back in like the '9s it was like 150.
It it's crazy um how much money is available.
It's the best time to build right now.
I think maybe that's the shift in I don't know if that's a shift in money necessarily, but it's there's definitely a shift in a mindset of of people I I think it's the you love movies, right?
Close Encounters of the Third Kind. Yep. Love it. Great movie.
and and there was a there was an investor I respect and and we and we we chatted over coffee and and he brought up um the interesting concept of how uh that movie illustrates Devil's Tower being Silicon Valley and you might have heard of that, right?
But it's it's like the many people that are gravitating um for unbeknownsted reasons to Devil's Tower.
It's like this it's this internal pull.
It's this we're sculpting uh we've had some sort of interaction with these aliens but we don't we don't know why we're going here.
And although there's talent, although there's culture, although there is is uh capital there, um I think a lot of people, you know, a friend text me two days ago, I got to get to SF.
And it's just this just this this poll um that uh it's Devil's Tower. It is.
And and not not to say it's it's a bad Devil's Tower, right?
But um I think that it's uh very interesting to see kind of how I think it's mainly just the it's possible, right?
That crazy dreams might just be possible out there. Totally agree.
Uh so you call yourself a contrarian.
What is something that you passionately believe that a majority of very very successful founders say just ain't so? Interesting.
I might get a lot of heat right now for this one.
Um I think I I don't know if I'm trying to convince myself not to drop out.
Um but I think I I'm even curious to hear your thoughts on the word dropout and is it overused and is it less of even signal these days to be honest.
Um and you know you go to college for these these these groups that you hopefully you know you hope Michigan kind of coraled some of the best talent.
I think there's leverage in the title of student.
Um, and I think again I think a lot of people would go against me on that to say that no student has no utility.
Um, you know, dropout that's that's utility that that brand name to put it on the LinkedIn. I'm done.
Um, and uh, yeah, I think I think it's a time to still kind of mess around and almost not have responsibility.
He had another friend get on a call a couple days ago and he said, "I'm in the real world now."
And that was kind of a a not a dawning moment.
I think he loves it, but at the same time, it's it's the shift into this real life now.
Um, and you don't have four years to just uh, you know, play the Well, I I think there's a lot of utility playing the manual game on on the campuses as we talked about to do that as a dropout.
It seems interesting, right?
I don't know if there's as much leverage there um to be a full-time community builder.
There's less there's less utility there.
But again, I think that's that's kind of a uh something I might get some some heat for um after this.
But uh yeah, that is the the current Our uh thing is to be the dropped out of Stanford to build.
What is what's your new flag?
Is there a new flag on the OSV radar that's instead of is it is it not even going to college in in that for that matter?
Like give me high schoolers that are are beyond their years like I I don't I have I'm trying to figure it out myself, but what's almost the flag?
So a new flag would be the one you mentioned.
Uh people who are so different that they, for example, our CTO uh just turned 21. Yes.
and literally what he accomplished in his young young life.
Uh completely unconventional um amazingly talented and and so he was one of those people who didn't he who didn't need that college time, right?
To him he kind of just looked at it at a waste.
Now I want to be very clear. I am not anti-ol.
I think that for a lot of people, as you mentioned, it's a great time in a young life to have all of those opportunities afforded to you that you honestly can't or won't be able to do, as your friend said, in the real world, right?
Um and and so we we we don't make it a marker like you don't get extra points if you have on uh you open your pitch to us saying yeah I dropped out of Stanford to do this.
We're like okay everyone's saying that talk to us about you know your idea your vision what you're doing.
vision what you're doing. uh but yeah the the we have found quite a few people who don't even for example I I I when I when we have a team that looks at all the various opportunities and then when the team is kind of like wow this
there's some legs here we really think we should do this that's when I talk to them and when I talk to them I have not looked at their CV I don't ask them where they're at college if they're young I don't give a [ __ ] What I want to know about is what's your idea? Why is
Why is my why are are you getting my team so excited? Like dazzle me, man.
And like I don't give a [ __ ] about credentialism, but I'm not opposed to college.
So I have this kind of weird like I I was uh at a company I started Netfolio which was basically the first online investment advisor sort of like a robo advisor now right except we founded it in 1999 uh and actually got patents on it.
A lot of cool stuff uh about giving investment advice over the internet and fulfilling that investment advice over the internet.
We have a patent on that.
We let it expire because we did it just for marketing reasons because I didn't want to be a patent troll.
But I had a a guy on who wanted to come work for us and we were on a Polycom and I was interviewing him and back then I did look at resumes and I knew full well that he had graduated from Harvard.
And so I'm like, "Okay, so what's wh why why why do you want to work for an online investment advisor that's mostly quant?"
And his he immediately was, "Well, you know, when I was at school in the Northeast," and I was that was the prompt for me to say, "Oh, where'd you go to school?"
And of course, I refused to do that.
And then I was it was kind of mean of me, honestly, because I just kept letting him prompt till he got down.
He was so frustrated by the fact that I didn't ask him where he went to college that on like the seventh question he was like when I was at Harvard and then I was like dude why'd you go to Harvard if you're interested in quant you should have gone to Chicago or MIT like he was just like his head was exploding right because the the you know I'm just not I I don't care I I I I I care very much about how you think.
I care very much about what your ideas are, but like the rest of it, I want to see you building helicopters when you're 15. Exactly. Exactly.
And and so that kind of stuff really resonates for us.
I am I can't believe that we've been talking for an hour and a half and it feels like 10 minutes to me.
U I'm getting the metaphorical hook here from my nannies.
Um, I've got two more questions for you.
Um, fast forward 10 years.
What would be the most controversial headline about you that you would be incredibly proud that headline?
Well, I'll I'll preface with planning is everything. Plans are worthless.
So, the 10-year outlook for me has always been um you know, I don't know what I'm what I'm doing tomorrow.
Um so, I'll preface with that.
Um that's another Charlie Mer um inspired philosophy.
This is this is a good one. Um I think Wow.
Um, I'm gonna go with Okay.
Many people have said to complete the Wikipedia page, I have to drop out.
Um, and so I kind of want to go against that since that's what everybody is telling me.
I'm very much one to go against the grain.
Um, and so, uh, that headline might I don't even necessarily I don't think I want it to be a headline.
I think I want it to be a photo. Okay.
Not even sure I necessarily want text. Um, okay.
Just just um just a picture um of of a a man walking away from the crowd. There you go. Okay.
Now, I wouldn't look at that.
I don't know if you've ever gotten Have you ever gotten an image rather than rather than text? Oh, sure. Yeah, absolutely.
In fact, I'm a big believer in that.
That's one of the modifications that is happening to us right now.
We we're going back to hieroglyphics uh with GIFs and and memes and all of that.
And if you are not well-versed in how to interpret those, you are going to be very very sorry because they are the new uh channels of communication.
Text alone that's you got you got to be you got to speak more languages than text.
Uh well, I even love that you are a big movie uh movie guy.
I think that long form in general I think I think you have to be I'm I'm bullish on people who are are consuming long form rather than short form. Yeah.
I mean what's really funny about that is like the I if you'd asked me that when I was you know your age, I'd say what do you mean long form?
I wouldn't even know the difference. Right?
because everything was books and like you just committed yourself to reading all that and like so yeah I think that um I'm I'm delighted by the way that you are interested in long form because that's you want to get to deep deep understandings of things you you the cliffnotes don't do it man the the chat GPT give me the summation of all of the important points in Arthur Kesler's the art of creat creativity.
Uh, and the only reason I know that is because I've read the book and I've also queried our AI and it gets 80%.
So, if you're an 80enter, great.
But you you get the really good [ __ ] when you really know and have really like if you're looking at many of the books that I have here, they're heavily underlined.
Um, and like chaotic notes.
Even though I think books should be essays and essays should be tweets, you don't I I started like marination over motion and and sitting with an idea and and totally life isn't a highlight reel. You have to live it all. Exactly. Exactly. I love that one.
I'm going to steal that from you.
Uh because we say uh the way we hire people at OSV, no one is hired immediately, right?
We put everyone on a six-month contract. Yeah.
And because we don't want to look at a snapshot, we want to watch a movie.
And uh but I like yours better.
Um it's not just a highlight reel.
I am definitely stealing that.
And I probably will not even give you credit. It's your podcast. It's your your right. I probably will.
I at least originally when I steal it I'm gonna give you credit but then I'm just gonna become I'm gonna probably overwrite my own memory and think hey I came up with that and then you'll send me this podcast saying you [ __ ] you did not all right how do people find you and then we're going to get to our last normal question yeah I mean uh email is best um to to find me so uh tww potter like Harry Potter um atyouish. edu is is best.
LinkedIn X also works, but love a good email.
Cold messaging in general.
It's how I met it's how I got into to this probably podcast.
I a simple cold message to Jim. Um I'm even curious.
I know we're we're running on time, but what are your thoughts on cold messages in general?
I'm not opposed to them at all, but you better make it a really good one.
uh because everyone is sending them now and and and like 90% of them are written by AI and we have AI sensing uh programs because we have an in-house AI.
we can tell instantly if something was written by an AI for us.
And loving AI, I I was originally like, are you sure that we're just going to ignore all those ones written by AI?
And uh the teammates who were reading them were like, trust me, Jim, if if you if you read a hundred of these, you would say you would you would issue a jihad against AI only. AI assisted. All fine, perfect.
But yeah, a good cold email because you can't tell till you ask and you got to get in the habit of asking.
And the other thing that's great about it is you got to get just absolutely fine with rejection, right? Totally.
Like when I did my first book proposal, you know, being one of the laziest humans on the planet, I wasn't going to write the [ __ ] book until someone said they would publish it.
So, I just did a query letter and then I went to the bookstore and got the addresses of the hundred biggest publishers and I photocop or I uh yeah, I photocopied the query letter and sent it around.
I got nine I the the list of rejection letters I lost it when we'd moved and I was so upset because some of them were so funny.
Like how dare you ask us to publish your dribbling piece of rotten business.
Like I love these people but all I needed was one and I got two.
Feels like all my friends and all my relationships these days are cold emails. Yeah. Yeah.
I mean, 98 rejections, two yes, and I was on my way, man.
And so, yeah, I'm not at all opposed, but make them good. Take some time.
And like, as you said in the beginning of our conversation, you got kind of think about it like, I got two lines to get this person interested.
Make those two lines really, really good. Yeah.
All right, Tommy, you're the emperor of the world. You can't kill anyone.
You can't put them in re-education camps.
But what you can do is we're going to hand you a magical microphone and you can speak two things into it.
And it is going to incept the entire population of the world whenever their tomorrow is.
They're going to wake up and they're going to think, I've just had two of the best ideas I've ever had and unlike all the other times, I'm actually gonna act on these two.
What are you going to accept in the world's population? It's a it's a big ask.
Um I think it's it's two two parts here.
Um so the first part being the life philosophy, the fundamental values, the kind of the mantra that I live by.
Um, and that's going to be adding more value to the world than I collect.
And then that turn elevates the lives of others.
Um, which which is very much at the end of my grave.
You hope that the the meter ticks a little more green than it did red.
Um, in terms of the resources you gave to the world rather than extracted, which is how I kind of see that.
Um, and I think secondly it's like how is the question like how the hell do you even how how do you do that?
I mean what what's the applicable route?
Um, and so for me, I'd say the applicable route is more um I think I think it's I think it might be twisted and and maybe hopefully my my reasoning uh makes sense to to kind of folks listening, but it for me it's it's life is this this this bucket of water.
Um, and you have to be very selfish.
We kind of touched on this a little bit, but you have to be very selfish.
Um, and that's a negatively conoted word in my opinion.
Um, but the best thing you can do for the world is to make the most of yourself.
Therefore, why this bucket of water is is kind of this um your life, the water is the love for yourself.
Um, and so instead of grabbing a pale or sorry, grabbing grabbing a shovel and kind of kind of splashing it onto other other folks, instead the best thing is maybe have a uh um a never-ending faucet.
And so have have the water overflow.
You did so much for yourself.
You're the radiant of energy um when you come into that room and and and things happen with your presence.
Um and you you do so much for yourself that that in in turn uh does does a lot for others.
I think the best anecdote for this that I I could maybe give was there was a friend um and we had coffee and uh I I kind of started to realize that um they uh they cared about reputation and they cared about um their their uh their personal image.
And so I was like, how can I break this down that would maybe maybe make them think differently?
And I started to think life as a as a car.
Um, and Jim, I'm going to I'm going to let you uh let you um drive around town for 15 minutes.
Uh, all family, friends, you know, everybody's going to see see your car.
Um, and uh, are you going to clean the inside or the outside? All right.
And then, you know, they they said probably probably going to clean the outside. It's like, interesting. Okay.
Well, we're now we're in Michigan.
We're going to we're going to take a cross-country trip to SF, you know, probably 30 hours straight.
Um, are you are you going to clean the inside or you going to clean the outside? You're going straight.
You're just maybe going to grab some snacks, some gas on the way.
Um, and they said, "H, probably clean the inside."
I was like, "Well, that's that's life."
You know, I I think we live in the short term.
Um, and and time is kind of an illusion, but it feels like we're very very present in the now and everything matters right now.
But in reality, I think you're driving on the highway and and like these people are seeing you for blips of six seconds, which feels like maybe years and in reality might, but in um and when you can kind of convert that over over time, it's honestly just a little a little glimpse at what they're seeing.
Um and so that those would be kind of my my hopefully my two cents.
Um and that, you know, it's a cross-country trip.
So, so clean the inside of the car and and the people that are, you know, the wife and the husband or the kids in the back and know everything is kind of the immediate immediate close circle around you that's being affected and yourself.
Um, so clean for for yourself and then kind of those around you. Very cool.
My friend George Max says that um if you're a super high agency person, it's not glass half full or half empty.
You're a tap that can be turned on and fill that class up as many times as you want. Good. So, I like that. I like that metaphor. You said it best.
Agency is what built America. It absolutely is.
Even a It is our hypomomanic edge making us a little crazy, but very productive. All right, Tommy.
My wranglers are wrangling. I got to jump.
But this has been super fun. Thank you, sir. Really appreciate it. Bye-bye.