This Ex-Poker Pro Built a Hedge Fund by Betting Against Beta – David Orr on Asymmetric Bets
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David, thanks so much for doing this.
>> Yeah, thanks for having me.
>> You started off as a professional poker
player
>> before building out Militia Capital,
your hedge fund that, correct me if I'm
wrong, has done over 40%
annual growth rate? What's been the
story in getting to this point?
>> Basically just been this wild ride of um
applying like what I learned in poker,
you know, to building a good track
record. I focused on performance. Um,
sort of thinking in the in terms of
bets. No. Um, I'm really just looking
for uh so in poker there's this term
expected value.
Um, and so your goal in a bet is to make
sure that you have a good positive
expected value before making it. And so,
um, in poker, the way you get good, or
at least the way I got good was I
systematically went through each type of
bet I would make, and I'd figure out
like what was not making money, what had
a negative expected value, and I just
systematically cut those out. And so, my
investing learning process was the exact
same thing. Um, you know, I don't need
to um boost my own ego and prove that my
idea will be right in 30 years. Um, I
just look if the idea is not making
money, you know, within months or, you
know, a couple quarters, I I'm wrong as
far as I'm concerned. And I'm going to
get rid of that type of bet completely.
And instead, I'm going to focus on the
types of bets that have a positive
expected return overall. And, uh, what
I've noticed, you know, other fund
managers not doing is getting rid of
those losing bets. And, you know, there
is that saying, um, you know, you'd
rather be right than make money. and and
that's just totally the case. And um and
poker will beat that out of you. You
know, if you're um wrong in poker, the
the feedback loop is so quickly that you
get in um you know, within even a
session, you made so many bets
um you know, that right away you can
start to feel it. Then after even a
month or two, the sample size is quite
good. Not not perfect, but you know, a
decent guess. And um and so I have way
more reps that way than most fund
managers do because it takes years to
see, oh, you know, I shouldn't have
stayed bullish oil for 3 years. And some
guys are still bullish oil right now.
And maybe they'll be right. I don't
know. But, you know, I don't I never do
this in investing. I don't stay wrong on
some idea I have. So, I think that's how
I've done it. And so, you you were
playing poker in Thailand for a little
bit. Um what was the moment when I guess
you started getting curious about um
about equities, commodities? What did
that look like?
>> Yeah, so basically um I was playing um I
was like one of the the better players
in the world by 2015 16. Um and then one
day sort of these really good players
showed up who were even better than me.
And I didn't realize what that was at
the time, but people actually figured
out how to use um like a bot in real
time.
that would play not perfect but nearly
perfect poker. Uh the game was being
solved around that time. And so um you
know I I realized, oh man, like
something's happened here. I'm not
winning money at poker anymore. It
wasn't that bad right away, but I could
see that the writing was on the wall,
even if I didn't even understand why. So
I stopped playing um around then. And
then
um I had some money saved up from poker.
I before I was just in the S&P 500.
Uh I sort of believed that market was
efficient like everyone else uh or most
everyone else. But um so I my whole goal
back then was to sort of do the academic
idea which is that if you can uh
increase the risk you're taking, you'll
also increase your return. That's that's
how they teach it in school. So I was
like, "Okay, great. I'm fine with risk
takingaking. you know, if I can get an
extra percent or two a year return,
that's fantastic. So, that was my whole
goal from the outset. Uh, but then as I
researched um how to do this, I reached
the opposite conclusion. It was actually
um the more risk you take, the lower
your expected return is in investing.
And if that whole backbone of this
academic way of thinking about investing
is wrong, then you know what else is.
So, I I
>> I just kept learning from there.
One of the things I remember you saying
because I listened to you on another on
another podcast and you said that you
read this paper called um betting bet
against beta. I have it written down in
front of me. What was what were the core
lessons that you learned from that that
paper? Yeah. I mean that paper just
refuted
um everything that they had taught. And
so if you collectively had one type of
uh investment that would underperform
and you have another type of investment
that will outperform, then my idea back
then was as simple as, oh well, I'll
just, you know, get long the ones
that'll do better and short the ones
that'll do worse. It's of course not
quite that simple. Um there's no free
lunch that big, but um
so at first all I did was just exactly
that though. I just went in and shorted
the uh higher beta stocks that seemed
pretty bad and I bought the lower beta
ones. And then, you know, you sort of
learn from there what works and what
doesn't. You learn other market
anomalies. You learn about uh good short
selling strategies. Um so you just sort
of keep piling up new strategies on top
of that.
And so from that point, I guess where
did your learning take you? So from this
paper to trading almost everything. I
mean, I think I was reading your I think
it was either your I think it was your
audited report on your website and I saw
all sorts of different asset classes
traded. I even saw a prediction markets
bet and I was very curious about that
and we can get into that later but it
just seems that
you know David you taught yourself a lot
and I want to understand how that
journey actually progressed I guess.
>> Yeah. I mean I I just I just try
different things. I I try anything, you
know. I didn't even know how to bet on
interest rates, for example, in 2020.
Um, and so in that example, it was just
as simple as, okay, so I asked some
friends, hey guys, how do I bet on
inflation being possible? You know, what
what are the odds that people are going
to pay for this? So, I just wanted to
see what it was. I didn't even really
intend on on betting, making the direct
bet, right? I was sort of more curious
about how this would fit into the other
bets I was making at the time. And then
one of the guys in our chat was like,
"Oh, you know, you can bet on this thing
called the Euro dollars futures option.
This is kind of esoteric thing, right?"
I had no idea what this was. And then I
was looking at this. I'm like, "Well,
wait a minute. This is is this right?
This this says that if we get inflation
within a few years, this thing will pay
200 to one."
And I was like, "What do you mean 200 to
one? what what are we talking about
here? You know, and I don't even know
what this was. I actually didn't know
exactly how this instrument even worked
in this CA case. So, that was my whole
concern was there like am I just
misunderstanding? Surely I'm missing
something, right? This pays like 5 to1
or something maybe, right? Or but you
know, I just sort of learn how the
product actually works and sure enough,
it was like 200 to one. So, all right,
now I'm a macro investor. You know, I'm
going to play some of these. I bet I
think I risked half a percent or 1% or
something on that you know it's like
okay um and I you know I wasn't once the
uh asymmetry went went away I sort of
closed a lot of it too early because it
started repricing by mid you know by
2021 really and I'm not a macro guy I
don't really know anything about macro
investing
so once it got to you know like
um 20 to1 it was a lot less interesting
um and by 10 to1 I'm like okay I don't
really know enough here to to really
have a read on the situation to know
that this is a good bet intuitively. I
don't think you you don't need to like
you know you you don't you like ask
normal people right like hey um if you
could make this bet on inflation you get
paid 200 to one I think norm would be
like oh yeah okay so you really didn't
need to be like a genius you just sort
of had to find it and think about what
was going on and um that I do that kind
of thing all the time in investing I
just look up what I think is uh you know
extreme extremely lopsided bet and then
once it passes I don't think about it
again. So, you know, another fund
manager might from that point be like,
"Oh, I'm now this hot shot macro
investor or something." For me, that was
not the case. I was like, "Okay, I I
looked at a few macro things from there,
but I was like, no, this seems pretty
competitive. These guys are smart.
They're playing their competitive game
here. I'm not going to get involved."
Um
but but yeah, if you can just find
anything to bet on, um you know, in that
prediction market example, um the Camala
Harris, um Donald Trump, that wasn't
what that one was about. And
you know, it's basically right near a
coin flip right before election day. And
so in that case, I just zoomed out and
said, "Well, wait a minute. here you had
um
Camala Harris wasn't even the candidate
and she had like only a couple months to
even prepare and so that's like already
pretty difficult to believe you zoom out
and think about it like wait a minute
you know two two months nobody even
really likes the lady you know a lot of
people do particularly hate Trump right
but but okay so so okay coin flip I'll
bet on that
uh similar kind of logic.
>> Yeah.
>> And so I guess what you've said there
and and I think this is the case for for
every great investor. They look for
asymmetric bets. They try to um have a
you know a basket of those. So say a
hundred um ideas that that they they
deem asymmetric. Um
how do you go? What's your process for
finding those bets? Um what does that
look like?
>> I just look at new ideas all day. So, I
sort of have a curated list of guys I
follow on Twitter. You know, they don't
really share that much alpha anymore,
which is kind of sad. I think nobody on
Twitter really does anymore. Um, but I
have my sort of internal group that I
talk with. That that that's always been
a pretty small percent of it, though.
Really, it's just as simple as I'll I'll
start like looking through tickers one
by one.
Um, and then I'm just trying to
understand, okay, well, what is this
company? What do they do? Does the do
the financials look interesting? That's
the biggest backbone of what I do. I
don't really focus on the other types of
uh bets we talked about too much.
Mostly, it's just individual companies,
which are nice because they're sort of
uh they're all correlated to the market,
but besides that, you know, they they're
pretty uncorrelated bets. So, um, you
know, one of my better calls was I was
actually short Nvidia in 2023,
uh, going into the May when the people
started realizing just how big of a deal
AI would be. And I, back then, I was
just short because I thought I was
shorting like a crypto miner.
>> Um, but then I got, you know, I got
pretty blindsided by this, uh, their
earnings result in May 2023. I was like,
okay, well, what's happening here? And
then I took time and I, you know,
understood what the technology was. I'm
like, "Oh, this could totally work." And
then I a couple months later I posted,
you know, Nvidia could be like the most
valuable company in the world. And then
that ended up happening, you know. So it
was just about understanding this
technology in that case and what they
actually have and who can compete with
them. And that was a pretty simple one.
>> At any given moment, how many positions
do you have in the fund? We've got uh
well we have my my partition and then
we've got other portfolio managers now.
Um all combined we have 1,200 positions
today uh overall fund level but my own
partition is about 350.
>> How do you understand each of those 350
names? Well, I guess how do you hold
that in your in your memory?
>> So the um the longs are really an easy
side. So that part of it I don't think
is impressive at all. It's just like
once you figure out a company is good
and you you know it's got a simple
thesis that you understand what what
everyone understands is different but
for me I understand that airports for
example that's a pretty simple business
they just benefit the more people that
travel the more profit they make it's
not like
>> it's not like an airline which is um
really complex dynamic business very
capital intensive airports are really
simple
um so it's easy for me to see how this
business can keep growing growing at say
5% a year long term. They're not going
to have any competition really because
airports typically there's one per city
maybe two. Usually if there even is a
new airport, you know that implies
really good things have happened, right?
It means that the demand has gotten so
damn big that your your investment has
already killed it like four times over.
So this is a really painfully simple
thesis. So, we're long I'm long like um
like seven airports, airport companies
worldwide.
Um and after I've convinced myself of
that thesis, I don't even really like I
don't read the earnings reports. Even
every like twice a year, I'll go through
and make sure that um you know, in fact,
the passenger growth is going up. Um so
that that's a pretty straightforward
example. Or another similar one would be
the natural gas pipelines.
Um, in this case, it's almost like a
utility. They're providing gas basically
to natural gas power plants. They now
have two new tailwinds in America
because they're going to export more gas
to Europe and they're going to supply
more power plants to AI data centers.
So, even without those new tailwinds
though, they seem at least reasonably
priced to me. You know, they're yielding
like a 7 8% dividend and uh those are
robust earnings. it's well covered. Um,
and then if you have any sort of new
tailwind on top of that, it's easy to
see how this this one will be, you know,
more like a 12% return. Um,
so yeah, longs like that are are really
simple that they really are. um or like
Japan as a whole, that's another theme
I'm long today where the corporate
governance is improving and the Japanese
government keeps doing things to force
um these small companies to treat their
shareholders better and they're really
taking real and it's not just a show and
it's a clear pattern and companies are
actually reacting. It's not like I'm I'm
theorizing that this might work. it's
like already very clearly working today
and so I'm just betting on a large
basket of those types of companies just
to play that theme really. The valuation
and things already look good too of
course but
um so yeah on the long side it's these
sort of themes that you can ride for
years or hopefully even like decades you
know I think in the airport example that
might be the case. Um
and then you know the only thing you
have to watch is valuation. if they get
way too expensive, then you have to sell
and find something new. But that doesn't
happen that often. So,
um, and then shorts are are a lot
harder. So, on shorts, you're trying to
think through there's like a lot of
different types of shorts, but like, uh,
an obvious example is this company's
just going to fail. It doesn't have any
good possible future to it. I think um
like I think cable TV is like this, you
know, like linear television. It's like
I don't it's almost weird that the
stocks are still trading because they're
so obviously screwed. Um but like
companies like Charter seem like in big
trouble to me. I've been shorting that
one on that really simple idea that
cable TV is bad. Um,
and then other types of shorts, it's
just um, like let's say they have really
poor management or like management's
even just dishonest and outright
stealing the money, which is a lot
different. So, some some types of
management are stealing in a different
way. They sort of uh, they get called a
fraud. And I don't actually like those
types of shorts because it's a lot to
follow. And these types of man
management are very um skillful at
pumping their um
at their story, right? And then that
means the stock could run up on you a
thousand% pretty easily. So I'm actually
not interested in that type of
dishonesty. I'm more interested in like,
oh, okay, so the business is stagnant.
Nothing's happening. Management keeps
paying themselves enormous bonuses. They
still have a a private jet they're using
all the time. you know, the shareholders
paying for that. Um, or like another
type of dishonesty is just an empire
building. Not like they're trying to
hype up a false new story, but they're
trying to um just do acquisitions for
the sake of managing even more and
solidifying their job even more. Um,
and once you figure it out, like in that
case, a management team is bad. Uh,
those are really long-term.
um you can just sort of stay short that
management team um for years. You know,
often these guys will keep their jobs
for decades. Um
you know, so
yeah, there there's just so many
different types of shorts, but you know,
as I've done this longer, I like to do
the longer term stuff, and you just uh
then you can have ideas that work for
years, which is how I've been able to
get way more diversified.
Um,
yeah.
So, it seems to me that at Militia you
like to bet on these long-term trends,
these these mac these themes that you
think play out for I mean, you've just
said it for years and years and years.
when I speak to let's say
pod analysts or people who've worked at
pods
um the mindset I feel is quite different
in that they are um constrained to a
particular sector and even within that
sector it's it's a couple names knowing
those in and out and trying to uh make
money every month or so every month Um,
I guess what are your thoughts on the
differences between those philosophies?
On your end, it's looking at the big
picture. On their end, it's scrutinizing
every little detail and then them
fitting into this
larger business. How do you think about
that? Yeah, I mean I've been kind of
critical of the pod shop model in other
interviews I think and some like someone
uh Twitter, but
yeah, I think that they're playing a
game that benefits from a relatively
smaller scale and then nowadays they're
so big. I actually don't think that
their whole super short-term focus can
actually work mathematically.
Um, so I don't think for that reason
it's good. I think the way it used to
work was kind of smart. Um, I'd say the
biggest benefit of what they do is it
doesn't let them stay wrong just by by
default. So, at the start of the
interview, I mentioned um that that's
the thing that gets almost all
fundamental investors, guys like me, is
that um they'll just stay wrong, you
know, like let's say that their long
charter and then their story just keeps
morphing over the years from like, oh,
it's this long-term wonderful growth
thing to like, oh, it's facing like a
somewhat of a headwind, but the multiple
so much better. And nowadays, I talked
to one recently, smart guy, very smart
guy. But I think a lot of these people
are smarter than me. I mean that like
genuinely, but they they just tricked
themselves and like now the story is oh
well now it's priced for um only a 2% a
year terminal decline or whatever or
sorry it's now priced for like a say a
4% a year terminal decline, but I think
it's more like a 1 or 2% or whatever.
And for me I'm just like man, do you not
even see the data? Even if you're right
that it is only 1% which this is cable
TV we're talking about. Okay. So even if
you're right though, like this is just
never going to even play out well. And
obviously what happens is over the years
these people
sort of um move the goalposts around and
they want to be right. They don't want
to admit that they were wrong and take
the loss or whatever. And the pod shots
can't do this. Like they will actually
get fired pretty quickly if they do. Um
and then if they're focused on well
what's actually working over the next
month and that's their timeline, then
they actually will change their mind
constantly, right? I think that that's
by far the biggest benefit of what
they're doing. So, uh, but is it
actually an optimal way to invest at
all? I don't think so at all. Where do
you see the future of
the hedge fund business? So, you're a
smaller fund. Um, even though you've
grown a lot recently, I was looking at
your AUM growth and I was like, "Wow,
this is crazy." Like, good job. Right.
Um and then uh but you see these
articles of call it the four big hedge
funds you know your citadels your
millenniums uh they've just gotten
bigger and bigger and bigger and
it just seems like with that
scale as you've said it's hard to find
it's just harder to find off right it's
just harder And so where do you see the
future of the business where you have
these guys growing? Allocators love them
because no one is going to lose your job
if you allocate to to one of them,
right? You're like it it's fine even if
they're down or even if they
underperform, right? It's you're no one
like no one is going to fire you for
investing, you know, allocating more
money. Um how do you think about that?
Like where do you see the future of the
business going?
>> Yeah. So, I think one of their um
mistakes is trying to charge like a
performance-based fee on that kind of
AUM. And they've been really successful
as multi-managers and everything, which
that aspect of what they're doing is
brilliant. I copied it. Uh but this
thing where they're letting the AUM grow
so big, um it's it's actually good for
their own bottom line, too, I guess, to
their uh credit, right? I mean, they're
just kind of printing money. Um I think
just their management fee alone is over
a billion dollars a year. And then
they're uh they call it a performance D,
but you know they're it's almost like
not that diversified. It's basically
just almost like another management fee.
And so, you know, they're collecting a
few billion dollars a year each one of
those shops just sort of every year,
year after year. So, for the guys
running it, I guess that's brilliant. Uh
for me, I I don't like it. I find it
distasteful to sort of um take the money
from everyone else and sort of put in my
own pocket. Uh, I can see I can sort of
understand the temptation of doing that.
Um,
but I'm not going to. So, you know,
that's why I don't just endlessly raise
money. I could at this point I could go
raise a lot more in the hedge fund
structure. Um but instead what I'm
intending on doing is like having a more
vertically integrated financial services
business where we um have a much lower
fee layer uh using ETFs. Um and then
basically
there's other like layers on top of that
we can add to create more value for us
and that's by cutting out various
middlemen. So, for example, the broker
dealer business um is really
interesting.
Um
especially for like levered investing,
which is what we do, you can really save
a lot of costs there. Um and basically
my idea is if we can get the cost down
to nearly zero and then we charge let's
say a long-term like a 1% fee on an ETF
structure, that's like really long-term
once you're way bigger. then it's a lot
easier to actually add value for people
in a real way on a 1% fee layer with
zero middleman than it is to have, you
know, this in practice, it's more like a
four or 5% a year fee. Um, with still
paying middlemen on top of that. Um,
so longterm, that's sort of what I have
in mind to do here. It's it's it's kind
of a big project to pull off, but
because you you need like um a lot of
legal compliance people to make sure
there's no conflicts of interest that
you know the assets are being treated
properly and you also need um like a lot
of portfolio managers
uh still. So you need the multi manager.
need to sell the portfolio manager on
this idea that hey, you should run this
lower fee thing. Even though you'll
probably not make quite as much money as
the citadels and things, you should do
it anyway because it's the right thing
to do. Um, I think it's easier to sell
people on that if basically you're
telling them that you'll be able to
raise them a ton of money using the same
brand. So that way from day one they
they uh get a huge fee, right? And then
also you'd offer like a lot more real
ownership versus the companies like
Citadel, they don't actually pay the
talent what they they deserve to. I'd
pay them, you know, most of that 1% fee
would actually go to the guy running the
money. Um, so I I basically plan on um
yeah, I'm really trying to reinvent how
this whole thing's done with uh lower
fee, no middleman sort of business.
um versus,
you know, like let's say that every time
these guys get, you know, their set of
sports tickets and everything for for
for free, like someone's actually paying
for those kind of perks, you know, our
company will have none of that kind of
crap. Um,
you know, so
that that's how I'm seeing it. And I
think the brand value alone once you get
people to trust that you're adding this
big edge and then money can kind of
automatically that's kind of uh already
wonderful for the PM especially if he
believes in the sort of ethical side of
it like hey we shouldn't we shouldn't
just fleece pensions and things out of
uh you know billions of dollars a year
like that's how I see the other
multi-manager jobs today.
>> When did you introduce PMs into your
business from running it solo to now?
Uh, I got the first one at the start of
2024. He's a guy I've been following for
a few years on Twitter. Um, and then the
second guy, um, I actually met him the
first time in person in 2019, so I sort
of knew he was a long time ago. And then
now we're trying another couple. We're
starting a new couple really small. Uh,
and I also found them on the internet.
So,
and so talk to me a little bit about
that business. What is it? What what
product are you trying to create?
>> Well, I just wanted to be a
multi-manager smaller scale hedge fund,
which is how the edge has been possible.
I've sort of repeatedly said the small
scale is what allows for such a big
edge. Um,
so yeah, I mean, if we can just get
people to agree to that at the hedge
fund layer, then the way um it's even
kind of a selfish thing if you just put
in a spreadsheet and see how it works
out if your your compound annual growth
rate is super super high. Just the way
your own carried interest compounds is
kind of insane versus like a lot lower
fee at a lot lower compound annual
growth. It's um
you know it's it's not actually people I
think are shooting themselves in the
foot even trying to uh grow endlessly.
Um
so so yeah this layer of the business is
really just as simple as let's have a
huge edge let's charge you know kind of
a regularish hedge fund fee for it and
then if you prove yourself in the hedge
fund then we'll we'll make you the
larger scale more marketing oriented ETF
uh vehicle instead and each PM would
have his own ETF. Wow, that's a really
interesting structure.
How's that been playing out for you so
far? How's it been going?
>> Well, the PMS are going great. They've
been killing it. I can see what they're
doing. I think it will scale pretty
well, so I don't see why it couldn't go
in an ETF structure.
Um, yeah, if they keep doing well, we'll
launch them their own ETFs probably in a
year or two.
um because the the ETFs are, you know,
it's still a very new idea to put a
hedge fund in into an ETF. So, we don't
actually know that uh confidently how
well that'll even work mechanically yet,
for example. So, I want to be a little
patient there and see what happens. But,
>> and for the fund for the funds that
you're building, are you how do you
think about risk management? Are you
doing the whole like are you hedging out
all the exposures?
Um, do you not view risk in that way?
I'd love to hear your thoughts.
>> Yeah, I think that the the pod shops get
way too neurotic about it, like they
basically want the factor exposure to be
zero or I've heard some through the
grapevine now that they're easing up on
that for their good guys to actually let
them have some kind of I don't even know
if that's true. Um, but
you know,
I I see it like um,
you know, you want them to be able like
you want the PMs to manage their own
risk in a way that seems good just by
itself.
Like, so I want to make it so I'm
watching the risk on my side, of course,
but I want it so that none of my filters
are are sending a big alarm signal,
right? And so if the PM has let's say 6
beta to the AI factor, that's totally
reasonable. Like that's fine. You can do
that. But if on the other hand, he's
like running three beta to the AI
factor, that's just a no-go. And I like
honestly if a PM is doing that kind of
thing,
I don't even think I'd step in to try to
get them to correct it too much. Maybe
maybe like a little bit. maybe like
maybe he's got this one blind spot. But
if I notice they're just doing this kind
of thing even somewhat often where it's
just totally reckless.
Uh then I would just end their their
deal, right? But so far the two PMs I've
picked, they don't do anything crazy
like that at all. They have their own
good risk management system as far as I
can tell as its own whatever. However,
they're seeing it personally. It's
already pretty good. And then my layer
is like everything's fine, too. And
then, of course, you have the the
broker's layer of risk management on top
of that. So, yeah, basically three
layers. And as far as I can tell,
everything's good on every layer.
And yeah, as for for pure factors, man,
I'm pretty sure this is a mistake. You
know, some factors are good to be long
and some factors are good to be short,
and that's totally fine.
>> Yeah. I mean, yeah, one of the questions
I do like to ask a lot of the pod guys
who come on or even just in person is
I mean, the market tends to go up. Um,
if you believe in the AI play by
definition, you kind of should be long
the AI factor. Uh, momentum tends to
work um, year after year after year.
obviously crashes sometimes, but
the thing I'm always curious about is
why not just include those in the
portfolio? And the answer they typically
give is that they don't believe that
they have skill in predicting those,
which I can kind of see. But what I see
more so is the guys on the top, you
know, the guy the center book, the guys
who see every single PM, I think they
can somewhat gain. And then I think the
factors and hedging all those out, it's
just good for building a product that
the allocators like, right? And um I
would like to get your I guess I'd like
to hear your thoughts on that. Why do
they hedge them out? Do you think that
neuroticism
um is just a consequence of them getting
burned before? Um would love to hear
your thoughts.
Yeah, I think the the biggest reason by
far is they have too many guys and so
they're neurotic about risk both factor-
wise, but the other key one is the tight
stop-loss wise as well. So, they're
really extremely tight on risk. And
that's cuz their whole platform is built
to say, okay, well, we can just sort of
let you can basically let anyone try and
then just see sort of see what they do.
And it the way they've structured it,
there's not any way that someone can
game it on beta. That's one of their
concerns, right? They're worried that
this guy's going to ride a factor bet
that can be kind of trendy and he'll
take advantage of us that way or he'll
take way too big of a risk. He'll take
advantage of us that way. Um, so they
don't actually under I my opinion is
they don't understand actually what
their people even do. It's almost like
they have a black box and they have a
rule set where things actually can't go
wrong is how is how they see it. Um,
but I think um,
yeah, I actually don't think it'll work
long term, but I guess we'll see.
No, we certainly will
>> because the thing is for me, I actually
understand my guys. I understand what
they're doing. Uh, I have a good I don't
I can't do what they do, but it's
adjacent to what I'm doing enough. So, I
actually understand it. Um,
and I can see that they're diversified
and um, they're not just doing something
crazy. They're not taking advantage of
me in some way.
And that that's the key thing. Like the
one of the new guys I'm backing, he's
very very bullish on AI and basically
his own portfolio. Uh, I'm interested in
backing him because his short book I
think has good alpha probably, but his
long book is just like it might as well
just be long in the S&P 500 or
something. That's almost how it is or
QQQ.
Um,
it's almost like why are you even
building a long book? Why don't you just
see why you just get long the index
then? But um you know, in that case, I
told him like, "Look, we're going to
start you small, but you know, in order
for me to ever upsize you, you're going
to have to learn how to um make
differentiated bets or at least control
your beta, you know, quite a bit because
I don't want to pay for beta. I'm not
interested in guys like one beta uh to
the general market. I don't think anyone
should pay for that." So, I think
I think that that extreme is bad, but I
also think the pod chop extreme of zero
is also bad. Um, especially especially
at the individual factor level. I think
that's where they're making a key
mistake
because if you're saying, okay, well, we
really shouldn't be paying you for like
S&P 500 beta. That can kind of make
sense. I I'd respect that. But there's a
lot of beta within that, you know, like
if a guy's bullish on oil, then he
should be long. whatever point for the
energy
uh factor.
>> David, you're super unique in that
you've taught all of this to yourself,
right? Um,
if there's someone watching this right
now who I guess maybe they're a student,
they're looking to make a very
unorthodox career transition and they
want to sit in your seat, which
taking a step back seems ridiculous how
your career's progressed. What advice
would you give and how did how would you
go about learning this skill of
investing? Yeah, everyone has a
different um
like a different um way of thinking
about things. We're all sort of
hardwired a different way. Uh you can't
fight that. And so one thing you can't
do is just sort of try to copy what
someone else is doing.
Um like like a big failure mode is just
everyone wants to be Warren Buffett.
uh of all that's like half of all funds
is just people trying to mimic Warren
Buffett. Um so you know I'd say don't do
this like you have to actually figure
out how you see the world. You need to
block everybody else out like really and
try to think through okay what can I do?
What can I figure out that's unique to
what what I'm
you know to my own talents at to my own
etc. Um
and then
there there are a few like rigid things
you you can learn like a more rigid rule
set like you shouldn't you know mix
leverage and concentration. You
shouldn't mix you know you shouldn't
take like stupid risks. You should
control your draw downs to some extent.
Pod shops take it way too far but the
math is really clear. You don't want to
have regular 30% draw downs cuz each
time you do you need a 50% win to get
even. you can't do this. Um so once you
learn those really basic that sort of
basic correct framework though you want
to apply your own
your own methods completely and I would
just say
just keep finding things to bet on and
then put it in a portfolio and like a
few 5% bet or whatever and then move on.
That's on the long side. But on the
shorts, they have to be smaller. But um
and then just keep finding the next one.
And then watch how it plays out over
three or six or nine months. And then
you know if it's not working,
take a good honest look about why it's
not working. Don't just say, "Well, I
must be right anyway, even though the
market's saying I'm wrong."
Yeah. Some of these guys, some of these
guys on Twitter, man, it's weird. It's
like their their track record is so bad
and they're still giving the advice of
like, "Oh, well, it's gone down more
against you, so you should be buying
more." It's like, "No, man." Like, the
fact that the market has gone against
you, it actually means something. It's
like one of the strongest tells there is
actually. Um,
especially like over a diversified
basket of things. If if like a bunch of
your bets are going wrong, you actually
have to figure out at least half of them
or more that you need to cut. and figure
out some new idea because you were
probably just wrong. And if you just do
this over and over and over again,
um I think you can actually get the
experience you need to even have a
chance at succeeding.
Um versus, you know, you think you've
done super deep research on these four
stocks, you're going to be long all four
and then, you know, who the hell
actually even knows? And I just see guys
doing that all the time and it fails. So
yeah, just get in a ton of reps.
Stay humble, you know, don't stay wrong,
follow a reasonable risk controls, not
super tight, but reasonable.
Um,
yeah, that's pretty much it.
The advice that's given to junior
analysts in an institutional setting or
aspiring junior analysts is work on your
modeling, pick a sector, cover a couple
stocks, run a book,
and
everything you're saying seems to be
somewhat contrary to that because by
definition,
you were saying find out your unique
edge by picking something and I guess
learning the general skill set of an
analyst. You are
trying to force another skill set on you
that maybe
is a base level that you need. What are
your thoughts on that traditional
institutional path for forming
outstanding investors long term versus
a more unstructured way of learning
where you are continuously reflecting on
your own personal strengths and how that
can translate into edge in the market.
>> Yeah. The whole the whole way they do it
is just wrong. Uh and it's not like my
opinion. It's like none of them have an
edge, right? So the whole institutional
way of doing it, it um it seems
responsible, it seems serious, which is
why I think it even goes on like this.
Um
you know, as long as um
I mean these institutions, they're not
really in the performance business.
They're not even really trying to
perform well. I I would argue what
they're what they're trying to do is is
sell a serious seeming product to a
committee that's running a pension or
whatever. That's their entire business
model. And those pensions would be way
better off just buying the S&P 500. Um,
so I guess to those people I'd say look
if you want to be in the marketing
business and you want to figure out a
way to sort of get your claws in and
take siphon away some of that money. Um,
then sure follow that path and you know
if you went to Harvard and you know you
feel like you can uh be a salesman using
that credential especially that
credential is key. If you don't have
that credential I would say just don't
even bother trying to go down that path.
you will always fail almost always
unless you're exceptional marketing. Um
but yeah, if you're going to become a
professional marketing person, you know,
I would just um I'd say almost just like
pretend like you have to pretend like
you're doing the model and everything.
That's part of the job. But man, you
could just have Chachi PT write up some
slot for you and then you could focus on
like building up your marketing skills.
I per for me, I think it's
reprehensible. I would say don't do it.
just go do something useful. Um,
but yeah, if you actually want to learn
to beat investing and have a real edge
and add value for people, don't listen
to what they do, what they're saying
because it it never works. None of those
guys have an edge.
I want to go deeper into that. So, you
mentioned the kid who graduated from
Harvard, right?
um he has the institutional pred he has
the pedigree. He can get into one of
these elite hedge funds institutions,
right? He can learn the institutional
investing way. He can be the salesman.
He can wear a suit and he can um he can
talk about factors and exposures and and
and wear the
um and about these these sophisticated
products that he can sell to
institutions
relatively easily in in a
straightforward way. Um but he's not
there yet. You know, he's he's still
let's say he's in his senior year,
junior year, and he tells you, I want to
be a great investor. I want to be um not
Warren, not Stanley. Um but I want to be
like my own unique
unique person and then and and and
really build up this skill from zero.
Where would you tell them to start?
>> Yeah, you get on Interactive Brokers.
You put in whatever 5,000 bucks or
whatever you can scrape together. You
could put in even a,000 bucks. I mean,
why not? Um,
I don't know what the minimum is for a
margin account if you wanted to get into
short selling. I think that might be
five grand. So maybe you for a buffer
you want more like 10,000 bucks. It
can't be that hard. Go get a summer job
and get 10,000 bucks and put it in the
account and then just like learn to bet
small on things and you you know you
don't have to you're not even really
trying to make money from this exactly.
What you're trying to do is learn how to
have an edge and make the, you know, if
you can win at 30, 45, 50% a year on a
small account, that's a pretty good
sign. It's very doable. Um, you have a
huge edge with a small account. You're
you have a you can get in and out of any
position literally instantly for no
cost. There's no friction at all. Um,
it's the greatest way to learn. And
yeah, you just bet on like try to find
like 30 genuinely different like long
ideas. So it's not all just AI, right?
Because you could say like Nvidia and a
bunch of other semiconductor stocks, but
that's all the same bet, right? So you
really want to find like 30 different
things long to bet on. It might take a
year or whatever to figure that out. But
if you're really serious about it, man,
you should just sit there and non-stop
15 hours a day is a competitive game. If
you're not if you're not loving it to do
it 15 hours a day within the first
month, just give up. You're not going to
win. Not you're not you'll never be a
great investor. U but if you're happy to
do it 15 hours a day and then it'll take
you a month or two to come up with a
list of 30 long ideas. Most of them will
be horrible, which is fine. And then,
you know, if you're find building a
short book and you have like um you
know, you have like 0.5% short positions
or even a little smaller and you want to
find 50 of these and that'll take
another few months. Um and then yeah,
you just learn by doing and and if you
have that sort of like a 50 position
portfolio on or 80 position if you can
get up to it, it's very hard to juggle
it, but the money amount is so small,
right? That's the key of this. If if you
like lose, who cares? you like lost a
few thousand bucks. It's like nothing.
It's like cheap tuition. So
that's what I would say. Just don't
don't do models. Don't don't read
academic theory. Don't try to see how
the supposed professionals do it. Just
try tons and tons of different bets.
Don't stay wrong and try a ton new
different bets and do it over and over
and over again. And by the time you have
like 500 or a thousand reps in, then
you'll start to have an idea if you you
can even have a chance at this. And
you'll actually have a real chance of
generating real edge doing it this way.
>> And let's say he does that or she does
that. Put the reps in um a year, right,
of of absolute focus.
Would you from that point try to work
for a money manager like yourself who
would give him the freedom and you know
he has a track he's young his um his his
intellectual mode is expanding. You can
tell he's hungry. Um would you try to do
that? Would you try to do it the
oldfashioned way? I mean old I say
oldfashioned but um it's just that no
one can no one it's very hard to do this
today. I mean, no one really does it
today where you you raise money from
friends and family and you kind of build
up this hedge fund that that you started
out of college. I guess my real question
is once you've put those reps in and
that training and you think that you
have edge and I guess you can prove it
with your track, what would be the next
step for you?
Well, I tried to build my firm in a way
where I actually said, okay, what
percent of the economics would I share
to make it so if I was in that person's
shoes? That's actually the question I
asked. And I that's why I came up with
the answer. I'm giving them 90% once
they meet partner after three years. So,
I think I've created a deal for any guy
who has a genuine edge uh to come work
for somebody like me. So, on the
economics part of it, I think that's way
better actually than running your own
fund. you don't have to deal with
fundraising or administrative costs.
It's actually just a straight up good
deal. The only downside of this model of
joining me would be um you're trusting
one person, right? So, in in in your
case, your counterparty to your
everything you're doing is one guy. And
the the big benefit of um is uh of uh
starting your own fund and doing that
friends and family and and doing what I
did. Right. Today we have like almost
100 limited partners and the largest one
is like 10% of the fund's money. So that
means even if I pissed off a whole bunch
of my LPs, I'm going to be just fine.
I'm going to be staying in business. It
doesn't it doesn't actually matter. I
have a very robust business that way. So
that that's the only reason to go off
and do it on your own. It is a good
reason, I guess. Um you can also have
your own sort of final say on risk
controls is the other big one. um level
like if you wanted to go get more PMs or
you have a different idea about risk
than I do because um ultimately I
control the risk, right? That's um my
key role here is figuring out um if
people shouldn't
do something and so
so yeah, I think if you do have an edge
though, if you have an edge and you just
write about it and you like just write
it like like you're role playing, you're
you're saying, "I'm a fund manager.
Here's my letter. And this is what I
basically did in 2019, right? I started
writing these things in uh quarter 1,
2019.
And um
and yeah, I promise if you have an edge,
people will find you. They will. And and
people like on the internet say, "Oh,
you can't do it. It's not possible."
This and that. These people don't exist.
If you have a good solid edge, like
actually the the the closest guy who's
like got kind of a raw deal is this
Upslope Capital on Twitter. He's a
really smart guy and he he has a small
edge. Uh or like not even that small.
It's like a pretty decent edge, you
know? He's like he's better than most
real fun bun managers, but he's not just
he's not quite there yet, you know? So,
he's kind of like in this this crappy no
man's land where that guy probably
deserves more success than he should be
getting right now. I actually that
that's actually kind of frustrating to
me. I think about it once in a while,
but besides him, like everyone else I
know that has had a big enough edge is
doing reasonably well. Plus, I mean, he
even that guy, he has a small fund. It's
not like he has nothing, you know? It's
still like he probably should be getting
compensated more and everything, but he
still has freedom and he still makes
some, you know, decent amount of money
doing this. So, it's not even the end of
the world in that case. So,
you know, yeah, I think if you just go
off on your own, have the balls to do
it,
you know, I I think good things will
happen if you have an edge. I wouldn't
worry about that.
I really like what you said
about
putting in the 15 hours of work every
day. And if you don't want to do that,
that being uh I mean a pretty strong
indicator that this game isn't for you.
>> Um for sure that's a good filter because
95% of people will quit right there.
Like if you don't
>> even higher
>> didn't look at if you didn't look at
Yeah. Even higher. So, if you didn't
like look at stocks, dine hours, go to
sleep, and you want the first thing you
want to do when you wake up. You don't
even want to make coffee first. You
maybe only do it because you know
they'll probably make you work faster,
you know, like the first thing you want
to do is start reading more. That's
that's how you know that you even should
be doing this. If you can't do this um
at first, I'm not saying you don't have
to keep this pace forever. Um,
you know, it's probably even detrimental
too to uh because you stop you're not
balancing things. But at first, like by
far the first thing to do is just learn
as many companies and situations as you
can. And yeah, if you don't have the
drive to do it, just give up, you know,
go either go be a professional marketing
person or or you can try to work in the
um there's not enough people working in
um the support roles. That's a kind of a
a quiet thing about the investing
business is uh
like most of the these professional
middle office or professional compliance
firms prof
um mercenary they don't actually care
about what they're doing but if you
could find like um you have a sincere
passion for some aspect of investing
services I think that can also be
another interesting route for people who
want to work in the this industry but
besides that so you know you have you
know genuine edge that's a workaholic
thing. You have the marketing aspect
which I I don't suggest you do it but
you know some people want to do it just
in that case realize what your role is
or work in support which is severely
underrated and I think there's a lot of
uh opportunities there for people who
are passionate about investing but maybe
you didn't have quite the talent or
quite the drive to do it. That third
route I think could be a interesting
path for people to look at.
I want to hear more about the support
roles because I think everyone wants to
sit in the investment seat. Everyone
wants to be Stan Ducken Miller or Warren
Buffett or even among mathematically
minded people. So I I'm I studied math
and physics from undergrad. I'm doing a
master's in financial engineering right
now. Everyone wants to become a quant.
They see the bonuses, they see the the
salaries, the internship salaries, the
first year salaries at Jane Street, at
Optiviver, at Citadel, and they go, I
want to sit in that seat. But like
you've said in most cases I mean the
quant equivalent of the 15 hours a day
is still 15 hours a day just doing quant
work right or and so
>> about that game but it's the same thing
I think. Yeah.
>> Yeah. Yeah. No exactly. Exact. I mean
it's the same level of obsession right.
Um but what you've said there about
support roles I've never heard that. I
don't think that stuff like that is
probably talked about enough because I
think we have too many people trying to
get into these very limited number of
buyside seats and people who were really
just interested in this because all
right they saw the bonuses they saw like
a couple reels on Instagram or some Tik
Toks about Jim Simons right but but tell
me what are those support roles and I
guess we talked about what is the type
of person that thrives in one of these
investment seats. What is the type of
person that thrives in one of these
support seeds?
>> I don't actually know um enough about
that to answer that confidently. I'm not
good at this to be honest.
>> Fair play. Fair play.
>> In my own hedge fund, um finding like
I'll put it if I put like a a job
opening for an analyst role, I'd get
like 200 resumes in a day or more
probably. It'd just be absurd. But if I
put like, hey, I want like an operations
support person, you know, I get like
two. Okay. So, that that just shows you
where the opportunity is. And then a lot
of hedge funds, it's a more cushy kind
of a boring job where
um the hedge funds pretty predictable
business, you know, especially for one
that manages risk well. These things are
in business for decades. Usually,
there's not almost anything to do and
you're going to basically be playing
social media all day. Um, so but if you
do a great job and you're really
reliable and responsive and you make the
portfolio manager's job easier, they're
they're they're never going to fire you
and they'll probably overcompensate you
compared to like a similar job. you
won't get the yeah the the huge
performance fee that everybody wants and
you won't make millions of dollars a
year but you could probably get yourself
in a pretty good two 300 grand a year
job there from a maybe maybe especially
if you like work for um a smaller up and
cominging firm a bit lower salary at
first and then they probably you know
get your rate up and there's just not
that many people looking actively for
those jobs there's nobody's proactively
saying how can I make the portfolio
manager's job easier there's so few of
these people or like even even like the
higher level people like um
trying to keep it anonymous here uh but
there's like some CFOs who did a very
mediocre job in my opinion for some
other funds for for instance and they're
not even doing anything for these funds
and I don't think the fund manager even
realizes it where the CFO could be uh
adding value in more ways if they'd
spend more time sort of um thinking
through broker relationships for example
or thinking through better ways to
structure certain types of trades. For
example, the really large shops do it
well, like the Jane Streets and
everything, but the smaller fund
managers, I think there's a room there
for a guy who's willing to be more
proactive and not just um you know, wait
for LP wires to come in or do a few
redemptions a month or whatever. That's
sort of what most of those people's job
is and it's basically nothing. But
there's a lot of dead time there and you
can actually figure out ways to add
value to the firm there. And if the firm
manager uh is smart, he'll recognize
that like, oh, he just saved us like $2
million a year in financing costs or he
figured out this cool tax thing which is
going to defer, you know, 20% of the
LP's taxes a year and that didn't even
cost us anything, right? A good fund
manager will probably reward you at
least decently for that. And you could
be making, you know, a few hundred,000 a
year, even a bit more. Um, and I've just
been doing this all by myself. And it's
shocking to me. I'll talk to other fund
managers about these kind of things. And
the other fund managers just aren't
doing any of this. They're not even
thinking about it. They're just like
letting these free lunches go away to
these middlemen.
Um, and then I I mentioned earlier I
have this plan to build like my own sort
of vertically integrated operation. And
that's a way larger role than a typical
person would be at one of these funds.
the in in my firm, the job won't just be
collect a wire, you know, fill out these
compliance forms and work with the
auditors and sort of busy work kind of
thing. Uh, in my firm, they're going to
be figuring out, well, how do we
actually structure this in a way that's
going to maximize our investors edge?
And there's no way I can juggle all
this, right? It's just too much. You
have to like know who the 50 brokers in
the world are. You have to understand
what types of services they're good and
bad at providing and why, how that's
changing over time.
Um, and then in in my firm, it's going
to, you know, if we we end up launching
our own broker dealer, of course, that's
going to be its own kind of large
workload, too. And so, I'm I guess part
of this is a little self- serving and
saying that, yeah, I'm looking for
support people who want to be really
truly passionate about it. Um, but I
think there's room for improvement in a
lot of other funds, too. And that's not
as intense as what I want
>> from running your fund, from hiring the
two PMs, from
looking for support people now as well.
I mean in the past as well. Um
I guess from working with people in the
investing industry,
what's one thing,
one skill that the best people have that
is so unbelievably underappreciated?
>> You mean for the portfolio manager or
for uh who?
>> For for the PM. I guess for both even,
but for for the PM first, I guess,
>> just think originally, man. Like, you're
not going to you're not going to have an
edge copying some Bin Twit idea. You're
not going to find all your ideas on
there. You just need to like look at
ideas genuinely by yourself. Do the
work. You know, I think it's good to put
your ideas out there because maybe
somebody will mention something that you
didn't realize. But you you shouldn't
just like listen to what they're saying.
There's a lot of naysayers and
everything. A lot of people who say why
the thing is broken because they're
quoting the sellside research or you
know things like this or the the the
perma bears will just say all of your
ideas are bad on the long side for
example. Um you just need to block all
that out and just do your own thinking
truly do your own thinking. Have your
own ideas. You know there there's a you
have a very unique brain and you you
have to use it that way. That's the only
way to beat the market.
>> I love that. And
what you said there about the sellside
research. It's funny. I mean, whenever I
ask someone for advice on how to start
investing, they say, "Do not read
sellside research because I mean, I've
only got recently gotten interested in
in the whole like in in in fundamental
analysis and how that works." And yeah,
everyone tells me sellside research like
they they will say whatever to get you
to to like their ideas.
Dude, it's just junk. I mean, I I know
because like one of our portfolio
managers had that job for a while and he
said his boss would just tell him what
he wanted the answer to be and he had to
come up with the report to justify the
answer that way then go sell the stock
and that's all you're reading there. And
this is and then so RPM is is like he's
like passionate about what he's doing.
Um but you know like
most of the people at his job they
didn't care. they just like nodded and
went along and they were happy to have
their, you know, decently well-paying
job. Uh, they're going to make up
whatever kind of nonsense. And it's just
like reading a word salad from a
23-year-old who doesn't actually care
about investing or the company or
anything. And why do people spend any
time on this, man? It's crazy.
And if there's a final piece of advice,
and I think we can end here. If there's
a final piece of advice that you would
give to um
to to students who who who want to get
into this game or or people looking to
make this transition, what would it be?
Just another thing I guess.
>> Yeah. Figure out what you're going to
do. Like if you want to perform well,
just focus on that. If you want to focus
on marketing, focus on that. And if you
want to focus on the operation side,
which means, you know, you could even go
apply for jobs at a broker dealer trying
to help them that way, for example.
Um,
you know, then do that. Um,
and you know, have an idea of like, do
you actually want to do it? If you don't
actually like want to do it, there's
going to be better ways to make money
anyway. This is a really competitive
field. Um
so yeah know what you want to do and
then actually like do it and then have
an honest feedback loop and say can you
do it and if not you should move on. You
know most people won't make it in this
business and but it's always good for
people to try. So everyone should try
but you know try doing what you're doing
and then if it's not working you know
find something else to do. You know,
there's
it's kind of sad these people who sort
of um are bitter and angry and they they
post about it all day on Twitter about
how, you know, they didn't like that
they didn't get the job or they saw some
other co-orker they thought they thought
was stupid who's succeeding and
everything and then they're all bitter
and angry and their whole identity is
wrapped up in this. Like, you don't want
to be one of those people. So,
yeah, figure out what you're going to
do, try doing it. If it doesn't work,
move on and do something else. That's
it.
Thank you for keeping it simple, David.
And thank you for coming on Open.
>> Yep. Thanks for having me, man. It was a
good time.
Ask follow-up questions or revisit key timestamps.
The video features an interview with David, a former professional poker player who transitioned to building a successful hedge fund, Militia Capital, known for its impressive annual growth rate. David attributes his investment success to the principles learned in poker, particularly the concept of expected value and systematically eliminating losing bets. He emphasizes the importance of a rapid feedback loop in identifying and cutting losing strategies, a concept he found lacking in traditional fund management. The discussion highlights David's journey from poker in Thailand to exploring equities and commodities after encountering bots that changed the poker landscape. He details his discovery of market inefficiencies, refuting academic theories on risk and return, and his early strategies based on the 'Bet Against Beta' paper. David elaborates on his process of finding asymmetric investment opportunities, focusing primarily on individual companies with interesting financials, but also exploring macro trends and prediction markets. He explains his diverse portfolio, including long positions in airports, natural gas pipelines, and Japanese companies, as well as short positions in declining industries like cable TV and companies with poor management. The conversation delves into the differences between his long-term, thematic investment approach and the short-term, sector-specific strategies of 'pod shops.' David critiques the traditional institutional approach to investing, arguing it prioritizes marketing and sales over genuine performance. He advocates for a self-taught, individualized approach, emphasizing original thinking, rigorous self-reflection, and continuous learning through practice. He advises aspiring investors to start small, experiment with various bets, learn from mistakes, and avoid blindly copying successful investors. The interview also touches upon the future of the hedge fund industry, David's vision for a more vertically integrated, lower-fee financial services business, and the importance of genuine skill and integrity over scale and fees. Finally, David stresses the need for passion, hard work (15 hours a day), and an honest feedback loop for anyone aspiring to succeed in the competitive investing world, suggesting alternative paths in support roles for those passionate about the industry but lacking the specific drive for direct investing.
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