Mental Models That Change How You Think | Bill Gurley
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Bill Gurley advocates for systems thinking as a foundational approach to navigating complex environments where small changes can trigger delayed, nonlinear consequences rather than immediate linear results. He illustrates this with the example of dating sites, noting that while increasing profile length initially boosted engagement, it eventually harmed conversion rates due to user fatigue, demonstrating why optimizing single metrics deterministically is often flawed without understanding the entire system. This philosophy extends to his investment strategy, which rests on a bedrock of classic financial knowledge from figures like Warren Buffett and Peter Lynch but has evolved through mentorship to appreciate network effects and growth investing beyond traditional value models. Gurley argues that while many Silicon Valley venture capitalists lack deep finance training, grasping the mechanics of eventual liquidity events such as IPOs or mergers is essential for accurately evaluating early-stage ventures.
Beyond financial metrics, Gurley emphasizes the critical importance of combining historical context with obsessive learning about emerging technologies to differentiate oneself in a competitive career landscape. He cites examples like John Lasseter's mastery of animation history and Magnus Carlsen's chess trivia to show how deep domain knowledge provides an edge, while also highlighting that general AI models may eventually dominate but vertical-specific workflows will persist due to specialized data needs. In the realm of global dynamics and regulation, he contrasts China's open-source ecosystem, which fosters rapid innovation through forced knowledge sharing among competitors, with Western duopolies that often seek restrictive regulations to protect market share. Furthermore, he critiques Wall Street's inefficient IPO pricing mechanisms compared to tokenization-enabled anonymous auctions and points out how stablecoins challenge entrenched payment infrastructures by bypassing slow banking settlement times like ACH systems.
The discussion also covers the unique traits required for success in venture capital and entrepreneurship, where storytelling serves as a vital tool for founders to recruit talent, raise capital, and close customers while writing cogent documents forces deeper problem-solving skills. Gurley identifies product instinct—the ability to build new categories—as another unfair advantage that requires deep conviction, contrasting this with traditional corporate models by noting how companies like Uber sustained unprecedented burn rates unlike their peers. He explains Benchmark Partners' unique equal partnership structure among five founders as a way to eliminate political overhead but acknowledges the scaling challenges it presents when removing clear leadership roles leads to simplified operations, such as maintaining basic websites for decades despite complex internal needs. Additionally, he observes that venture capital increasingly favors younger investors who can dedicate eighty-hour weeks to mastering niche technologies like esports or YouTube, whereas older generalists often face limitations due to age-related responsibilities.
Ultimately, Gurley defines his own success not by continuous accumulation but by the decision to retire when feeling no work remained, signaling a desire for a new chapter in life. He aims to apply his analytical skills honed through venture capital—specifically synthesizing problems and understanding complex issues—to address broader societal challenges rather than remaining solely within traditional financial sectors. This transition reflects his belief that true expertise comes from staying on the bleeding edge of knowledge while maintaining a holistic view of systems, whether in finance, technology, or global markets. By integrating deep historical study with forward-looking innovation, professionals can navigate inefficiencies and structural barriers to create more equitable outcomes for capital allocation and societal progress.
Read the full video transcript
We do live in a world where information
is really cut up, but we also live in a
world where you can have access to more
information than you ever could.
[music]
>> What are the key mental models that you
keep coming back to that sort of explain
how the world works to you?
>> I'm a big believer in systems thinking.
There's a there's a book called Thinking
in Systems that I read.
>> What does that mean to think in systems?
>> I'm on the board of the Santa Fe
Institute. The Santa Fe Institute
studies complexity theory. I would
describe complex systems as
multivariable nonlinear systems. And
multivariable nonlinear systems are very
hard to predict. They can behave one way
for a long time and then one variable
can switch and they can behave another
way. The weather, stock markets, all
these things. There's consequences that
can be first, second, third derivative.
And you know, you you can't just think
with a linear model or just think one
variable because
things can can go way off the path.
Being aware that if you make a change
here, it could change something here
which could change something there and
it has to be the whole system.
>> How does that help you when you're
solving problems or thinking about
stuff?
>> I think it keeps you out of trouble
because you can avoid
consequences that you might find out
later. You know, I was I was talking to
a guy that worked at one of the large
dating sites. They had this this idea
making the profile longer would lead to
more engagement. Simple, you know,
heruristic. And they tested it and it
was true. And so they rolled it out.
They found out many many months later
that it let it it was negative for
conversion like when people knew more at
that level.
>> Oh, interesting.
>> And so but but you find that out way
later. There's my point about like a
second derivative effect. And so you
just got to you got to be really
conscious of the consequence and not get
too deterministic about a single metric
or a single variable and know what's
important and what's on top.
>> What was the process you took to go
about learning the craft of investing
and who were the mentors and peers that
played a role in that? So because I
started on Wall Street, you know, and
not in venture directly, I got caught up
in all the people you would expect, you
know, around
Wall Street and stocks. And so, you
know, that starts with Peter Lynch, One
Up on Wall Street, you know,
best-selling book, probably the first
book I read about investing, a random
walk down Wall Street, Burton Male, all
the Buffett letters, you know, uh, Ben
Graham. Once you read Buffett, you have
to read Ben Graham. And so, and then
Howard Marx, uh, who's just incredible.
And you were talking about the purpose
of your podcast. those those people have
spent their whole career assembling
their thoughts and publishing them, you
know, along the way. So, so that those
were the ones that I read everything. I
I think I had a very strong kind of
bedrock of financial understanding. It's
>> it's interesting because as you're
saying that, I'm thinking like value
investing and then you went into
nonvalue investing in a way, right? Like
how did that translate? How did what
Buffett said translate into seed
investing and sort of venture investing?
>> I think having a firm understanding of
the bedrock is super valuable and then
when you recognize the need to innovate
on top of it, it's just really good to
have that foundation. I have an
incredible peer in this guy, Mike
Moeson. I don't know if you've heard of
him, but he's a writer of financial
books. We started at First Boston. He
had probably been there a year year or
two ahead of me. So it it you know just
super fortunate that I landed in the
same place as him and we've been
lifelong friends since then. He
introduced me to a gentleman named Bill
Miller who ran leg mason and had this
like 15-year run of beating the S&P one
of the most famous investors of all
time. And he claimed to be a value
investor and he was the largest
shareholder of Amazon for a very long
period of time. And what he would say,
I'm getting back to your question. He
would say that, you know, value just
means that the asset is underpriced
relative to what you think it will be
worth in the future. I spent a lot of
time talking with Bill about network
effects. And if you believe in that,
then Amazon might be able to grow at a
unreasonable growth rate for a very long
period of time, which he believed. And
so that that's how you get there. But
yeah, I I I've often thought that many
of the VCs in Silicon Valley would
benefit from having a better
understanding of finance. And one other
answer to your question about how it
becomes valuable. You know, I've always
thought of Wall Street as the buyer of
the product that venture capitalists
create
>> because of the eventual liquidity is
either an M&A or an IPO. And now the
price is being set by that group and
that institution. So if I know what they
value, even if we're starting at a very
early place, two people in a PowerPoint,
you're still thinking about when this
thing grows up, is it going to be
something they're excited about?
>> Yeah. The trajectory matters more than
the starting place, I think.
>> Yeah. That that's where you're going to
end. That's the out that's the output at
the end of the day.
>> What does it mean to know the bedrock of
the industry? We live in a world where
people skim. They want the gist of
things. They want, "Give me the summary.
Give me the executive summary."
>> I'm going to tell you a story. So, um,
my partner at Benchmark, Alex Balcansky,
would go to this charity auction that I
think Andre Agassi would run in in
Vegas. And one year, he bought a dinner
with John Lacier, the creative genius
behind Pixar. Mhm.
>> And we go to John's house and he serves
us in his [clears throat] movie studio.
He serves us in his viewing room a 10
course meal. And each piece of the meal
is tied to a classic cartoon that he
believed was was super important to
understanding animation. And he would
show it and he would talk through it and
explain it. And you see that and you're
like, "Holy crap." like he knows more
about the history, you know, and and
then here's another data point that I
just love. There's a, you know, world
chess tournament and they take a break
and run a trivia contest and [snorts]
Magnus Carlson wins the trivia contest
and it's all about the history of chess.
We do live in a world where information
is really cut up, but we also live in a
world where you can have access to more
information than you ever could. And
that's even more true now with LLMs. I
mean, you could just sit there. You have
an hour drive and you could sit there
and talk to OpenAI and learn about
anything you want to. And I think more
people would benefit by studying the
history of whatever field they're in.
The there's another one that we
mentioned is uh Picasso was a wildly
successful realist painter by the time
he was 14. If you go to the Barcelona
Museum, you can see that. And I don't
think anyone that looks at his cubis
paintings would in intuitit that that
was true. And then one last thing I
would just say about this, and I think
this is broadly applicable to almost
anyone in any career. Imagine, let's
just pick a field. I'm going to pick
marketing. All right? Imagine you're
interviewing for a job at PNG or Pepsi
out of college and there's 20 people
there and you're the one that
understands the masters of marketing
more than the others and you're able to
bring that up in the interview. Isn't
that wildly differentiating?
>> Yeah, totally. I can't I can't imagine
how it would land on me if I that I met
that person and and yet other than
fields like I think in like literature
you probably everyone studies the greats
but in these other fields it's not a
practice and I I just think it would be
like remarkably differentiating for
people to walk around with the history
of their field. I had a friend who
actually recommended to people that
their college essays do that when their
admissions essays talk about like if
they want to go into physics talk about
the forefathers of like physics and and
show them and like you'll instantly
create tons of contrast with everybody
else
>> and you'll show a passion like it it it
infers passion
>> to want to know that. Um, and then the
other part I get into, if that sounds
tedious, it's probably not the right
[laughter] like like if it's tedious to
learn that this isn't a passion like
you're not in the right I don't think
you're in the right lane.
>> So you've spent your life working with
outliers, all these founders. Are there
is that a common trait? And I mean not
just the the history of the field but
the details as well.
>> I don't know if the history is a common
trait. I would say that that a more
common trait that's related in the
entrepreneurial world is obsessive
learning like constant learning because
the disruptions that allow for the
technology waves that allow for
companies to be disruptive and take
market share from an incumbent are all
tied to something dynamic that's
happening on the edge. And every
entrepreneur that's exploiting that,
it's AI right now. They're they're going
home at night and reading everything
they possibly can cuz the edge is moving
and they need to be right there and they
need to be a top 1 percentile person
that understands this new thing that's
happening.
>> And today it's AI, but that was true of
the mobile wave. Like like when the
mobile phone came out, there were no
engineers that had written apps for
mobile phones. and a few people got on
that edge and figured out what that
meant. And that requires obsessive
learning on the edge.
>> The way that I'm thinking about that,
and maybe I'm coming at this wrong, is,
you know, if I'm young and upcoming, I'm
on that edge. And I'm going to dive into
it, but if I'm an incumbent, it's much
harder to dive into that because it
might mean, it's the innovator's dilemma
in a way, but it might mean giving up a
previous decision I've made or saying
that I've been wrong and going
backwards. How do you think about that
in terms of competition?
>> I mean, I think that anybody in any
field should want to be on like curious
about the bleeding edge and what
happens. And, you know, as a venture
capitalist, you know, we're always
definitely afraid that some new app's
going to pop in the app store that we
haven't seen or and so everything that
comes up, I play with, I roll around.
Right now, I have like five premium AI
accounts cuz I just don't want to miss
something. and you get trained that way.
I think everyone should operate that
way. I mean, it's kind of an interesting
contrast. I'm suggesting you should
understand the really old stuff, the
history, because it's differentiating
and shows a passion and it gives you a
great frame of mind, but you also want
to really understand the new edge. If
you do both of those things, like you're
I think you're a power player in your
field, you know. And the the second one
is a great way for young people. That's
another thing that could really
differentiate you in an interview. If
you're applying for that marketing job
and you understand all the legends and
the history, but you also really get Tik
Tok, like that's super like that's going
to be a very differentiated skill going
into those companies and it matters.
Like it really matters. Gives you a
chance to shine. If I was to observe you
use AI for a week, what would surprise
me about the ways that you're using it?
>> You often underestimate how much it can
do. So you might ask it um to f identify
the top 10 of something and then you're
going to take those 10 and go study
them. But you can say identify the top
10, list their pros and cons, and then
rank order them based on this dimension.
and then rank order them again based on
another like stuff you would have done
later you can just build into the prompt
and it can it can do more of the work
earlier for you early on I would often
ask it for numbers and then I would go
add them up and I'm like oh you can
just tell it to do that part too
>> do you find chat GBT is the best one
>> I I like the project structure and I'm
being sucked into the memory element in
that it knows who I am and it knows
things about me for for restaurants and
stuff I' I've been using Gemini just
because it has all the Google review
data and you can, you know, you you
don't just ask it which restaurants are
good. You can say what are three plates
people rave about and what have people
warn against. Like you can go deep into
the menu, which I I do all the time. You
know, the coding people swear by uh
Claude.
>> Yeah. And I met a guy this morning who
says for finance he prefers perplexity,
but if he's doing deep research on
companies or like companies and
countries he doesn't know, he find
Claude does better. So I think it's
still a mix.
>> Do you think we're going to end up with
like one model that just sort of like
dominates or do you think we're going to
end up with niche models and they're
effectively going to be commodities in
some way?
>> I think it's highly dependent on how
things play out. There are certain
examples in the verticals especially in
the coding one which is probably the
largest vertical right now where people
have swapped out models you know cursor
even lets the the user pick the model
that they're using and as we move
towards optimization and price
optimization which isn't really the
objective function right now but it will
be in a few years um you may see more
people try and do those swaps. I think
the thing you know that could cut
against that if [clears throat] the
regulation gets extremely difficult and
mundane and expensive that could
actually lead to more igopoly and I
think some of the players know that and
are begging for regulation.
[clears throat and laughter]
>> Oh cuz they want that because it's a
protective mode
>> pulls up the bar against especially
against the Chinese open source models.
>> How do you think about regulation in the
global sense? Just zooming out a little
bit here. If if one country is regulated
on AI and it slows them down effectively
and another country is not regulated on
AI and it speeds them up like how do you
think
>> this has come up especially around
copyright you know and if if if if our
models all have to adhere to some
special rule and there's already been
settlements and whatnot and the Chinese
open source models don't it it could
have it could have an effect you know
it's very un I'm very uncertain how the
EU might rule in that type of situation.
So, I don't know. You know what I'm
saying? I don't know how they might view
it.
>> How do you think about it from a systems
point of view? Just from like China
seems they have four open source models
now that are really good. Is that
>> By the way, this is a great a great
question just to talk more about systems
thinking. So um they have like 10 open-
source models and so you have a
situation where the competitive dynamic
in China is more intense because it's
more intense. Everyone's chosen to go
open source and that creates a system
that in my mind is capable of innovating
far faster than the competitive system
we have here. All the models learn from
one another. You can actually have a
model train another model or test
another model. I'll use a simple
metaphor but imagine you have two
societies and both agricultural
societies and one of them when all the
farmers come to market they just sell
each other goods and then they go back
and the other society when the farmers
come to market they're forced to share
best practices with all the other
farmers.
Which which one of those is going to
going to evolve faster? And open source
allows me to see what they're doing, how
they're doing it. Are they open sourcing
weights too or just the
>> Yes. And a lot of them are publishing
how they figured it out like new
techniques and and things like that. So
it's more it's way more dynamic.
>> And does that help Western nations then
too?
>> Well, there's an irony that a lot of the
startups are forking those models and
this would be a question of how
regulation plays out and whether you
know someone tries to stomp those out or
not. I would say it's kind of a quiet
secret just because I haven't read it on
the front page of of the journal that
you know especially from a breath
standpoint like a volume companies are
using these models all over Silicon
Valley.
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If AI is really going to change
everything or, you know, have such a big
impact, how does it change how you
invest? and you look at a company, are
you looking like this is a rapper on AI?
You're effectively like a calculator app
on the iPhone or like how do you think
about
>> I I I think that question is up for
grabs and it's a hot discussion between
everyone. So, you know, if if you
believe that these models
[clears throat] become near sentient,
then that there will be no need for a
vertical model because this one model
will just do everything. I probably come
down on the other side of that. I think
that there are workflows and data modes
that if you get and and also just
understanding like there's three or four
legal startups in the AI space, they're
just spending so much more time making
sure they ingest all the case law and
and really understand, you know, the
processes and principles there and and
then you implement with them and they're
writing stuff on your behalf and you're
building new databases out of there. I
just don't know that you then switch
that to chat GBT as they climb up the
stack. But and I'll take I'll flip back
to the other side. You know, they have
talked about in their product groups,
you know, going after verticals. So,
it's I think it's a TBD. People point to
Microsoft, you know, starting with the
OS and then, you know, there were there
was Lotus one 123 and there was I forget
I can't even Oh, there was a word
perfect like I can't remember the the
specific apps, but you know, they
eventually moved up the stack. That
could happen. We're going to see how it
goes. Do you think there's limitations
to how we're training the models now,
which is sort of they're trained on all
the data from the internet, including
like, you know, Elon has the opposite
approach where he's like, we're going to
take all the data and then we're going
to filter out clear untruths. We're
going to use that as the starting point
versus the other. I do think that there
is a valid argument that we might be
running out of data, you know, that that
we're I call it painting in the corners
like you know, just we've filled in
everything right now. One of the most
powerful um solutions to improving the
models is hiring experts. literally
hiring experts for thousands of dollars
an hour to to sit in and fine-tune and
and you know ask very hard questions and
then tune them to to be able to solve
those. I there's got to be a limit to
that like where's the edge of of human
knowledge. So it's a big question like
do do we run into asmtopes or not? And
part of it goes back to do you believe
these things can become [clears throat]
super intelligent at which point they
start solving things that we've never
imagined. There's a lot of debate about
that.
>> I mean the I guess the theory correct me
if I'm wrong is like the minute that
they are super intelligent they can
effectively make themselves a little bit
better and at that point you just you
enter a nonlinear curve.
>> That that's an argument that some people
have made. I I don't know that I believe
it but but
>> give me give me the other side of it
>> rather than me stand on that hill like
Yan you know Yan Lum you know makes that
point like he says that that the next
version of AI is not it's not LLM it's
it's outside of LLMs it's broader than
LLMs and that that we're going to run
into a a asmtote with these because
they're language based and there's just
a limit to what language what you can
capture with language which is part of
why they're not specifically great with
math and numbers, right? There are much
better people to talk about this than
me, but there's a people point to this
famous game that Google Alph Go where
Google implemented and the bot
eventually came up with a move that was
shocking to all humans and that I forget
the number. It's like a famous move
number, whatever. And that is proof that
they can innovate, you know, beyond what
they're taught. The people that take the
other side say that's a very constrained
game and environment. And the computers
can search a field of possibilities
that's impossible for a human to search
because there's just too many, right?
And that that gives it the ability to
find that move that that we didn't know
about before. But in the real world,
it's not constrained enough where you
can tell it to walk all the possible
paths. There's an infinite number of
paths in a complex in a big complex
system. And by the way, those AI models
aren't LLM based like AlphaGo is not LM
based. It's a AI model trained to a very
specific constraint system.
>> And that was trained just by playing. Is
that true?
>> Yeah. Yeah. Yeah. Exactly. But and even
FSD is you know at Tesla is a
constrained environment like there's the
inputs are the brake and the steering
wheel and the gas pedal
>> and or those are the outputs actually
the inputs are are all the visual data
>> it's scary good [laughter]
I mean I was telling someone the other
day I was like I would be comfortable
sitting in the back seat at this point
with full self-driving like I don't I
don't feel a need to drive anymore.
>> Yeah.
>> What's your take on that? the corner
cases.
>> Would you sit in the back seat with your
Tesla driving?
>> The the the corner cases are impossible
to fathom at this, you know, right now.
Yeah, maybe at some point. I mean, I
certainly think if it were in a world
that didn't have the randomness of the
real world. So, if you were in a g
geographic area where all of the cars
were that, it'd be easier to to to go
into that mindset.
>> Is that We got humans that think it's
fun to test. People are jumping in front
of these cars like that's that's that's
not good.
>> I was talking to Rory Sutherland. He's
like, "You can just have fun with this.
They're going to stop. You know they're
going to stop." And so like you don't
even have to look both ways now. What
are the consequences of that?
>> Yeah. Yeah. That's not good.
>> What do you What opinions do you have
today that are sort of non-conensus that
you you think are correct? Having spent
ton of time in China over the past 20
years, it's hard for me to adopt this
mindset of vilification that's heavy
amongst many in Washington and now many
in Silicon Valley. The US is like 3,
four, 5% of the global population.
>> Yeah.
>> American exceptionalism. When people
utter that word, I always wonder like
imagine the other 95% of the planet
thinks when they hear someone say that.
You know, that's probably a
non-consensus
viewpoint.
>> Are there Do you think we're overfunding
this buildout? How do you think about
that?
>> I saw that smile on your face.
>> I mean, it's such a hard question to
know. If you told me five years ago that
the that these uh max seven would become
worth $3 trillion and then turn around
and take their free cash flow from 50 to
100 billion a year down near zero
because they were going to spend it all
on capex, I'd have been like no way.
Like I wouldn't have believed it. So
from a certain standpoint, I'm shocked
that the money's this big. I will tell
you that the venture capital community,
you know, I meant we talked earlier
about increasing returns and and that
concept and other people call it power
laws like when startups have become
important in an ecosystem and then
they've been able to prove that they can
grow and that that growth might be a
function of their size already or their
footprint or their users and that would
include everyone from Google to Amazon
to Meta that they end up being worth way
more than anyone thought. And I think
the investor community writ large has
slowly
become aware of and believes it strongly
in increasing returns and power laws.
And so over time, if they all believe
that, they're going to be more willing
to invest on the come and take risk.
Right? That that makes sense that
follows. And so, you know, someone
forwarded me a chart this morning of the
losses of the leading company in the
field prior to going cash flow positive.
And you look at, you know, what for for
for Amazon it was like two or three
billion. For Uber it was like, you know,
15 billion. And now for these companies,
it's going to be way bigger than that.
And so the venture capital community as
a whole is is getting more risk-seeking
and taking on more risk because of their
knowledge of how things have played out
in the past.
>> What do you think are assuming we are
overfunding? We haven't had a correction
like
>> not not really
>> like a mini one kind of like and usually
that that weeds out sort of the weak
competitors the strong ones survive and
>> it depends. Yes, but but it can be, you
know, if you look at what happened with
the.com crash, you know, there was a
four year, three or four year lull
before the Amazon of the world started
climbing out again, you know, it was it
was like a nuclear winter like right now
there's so much optimism and belief in
AI. you get to the place where there's
very little, you know, um I don't know,
some of these the these quote circular
deals that people are talking about
>> [snorts]
>> um enhance the probability that we'll
have a correction, but also extend the
time before we have one.
>> Wait, how so?
>> Yesterday at the dealbook conference,
Daario was asked about circular deals
and he goes, "Well, maybe people just
don't understand. Let me explain how
this works." Um, you know, imagine
you're a cloud service I'm I'm echoing
what he said. Imagine you're a cloud
service provider and you notice that
this company Anthropic wants to develop
this model. It's going to cost maybe $5
billion, but they don't have that money.
So, you give them that money so that
they can spend it. And I'm like, well,
if you didn't give it to them, they
wouldn't spend it. And so like the
growth of everything is enhanced by the
fact that you're giving money to
companies to spend back on your services
they wouldn't have otherwise. And so if
you were in a more constrained
environment where you didn't do that,
things wouldn't be growing as fast. You
inflate you inflate what's happening.
>> So you push further ahead faster.
>> Yes.
>> But there still is likely to be sort of
a culling of the the weaker competitors.
Look, first of all, if a company's
successful, someone will knock on your
door and try and give you more money.
So, like almost every round is
preemptive for successful companies. And
when you take that much money, $300
million, the only way to spend it is to
take your burn rate up. And I always
thought of burn rate as a measure of
risk. 10 years ago, like it was super
risky to burn a million a month. You
know, today these companies are burning
five billion a year. Like like you know,
you're you're burning a hundred million
a month or more. Like it's really hard
and this may go back to financial
bedrock and whatnot. It's really hard to
know what your unit economics are
>> when you're being that aggressive
financially.
>> Do you think things will change? Like I
I wonder about the role of retail
investors in this like if you tokenize
some of these assets like they might be
competing with VCs in some way to fund
some of these startups. How how do you
think about all of that playing out?
>> Well, first of all, there is zero lack
of fund availability right now. So
>> that's not the bottleneck.
>> Yeah, there's [laughter]
>> the pricing would change, right? There's
no con.
>> This is kind of played out in the public
markets. I mean, I think you look at
obviously like stocks like GameStop, but
I I think most people believe Palunteer
is a stock that retail investors really
love and take it to a valuation that
it's very hard for institutional
investors to get their head around. So,
some of some of that has played out.
Yeah, it's it's there's a there's a risk
with tokenization, especially if it
happens on assets that don't have
regulation around financial disclosure
that you get a ton of speculation and
even worse manipulation.
>> Do you think that that would affect
private companies if there was like if
somebody figured out a way legally to
tokenize Stripe, for example, and the
price of the the Stripe share that's
tokenized effectively fluctuates wildly?
Yeah. Do you think that has an impact on
Stripe or its employees?
>> Well, it would. One of the reasons
they're staying private is so you don't
have that dynamic
>> because they have more control over sort
of like the market cap pricing
>> when they do um liquidity events for
their employees. They sit down with a
handful of investors they trust and they
negotiate a price and so it's done on a
one-off basis. And I think we're going
back to the financial bedrock. The
underlying asset probably does move
around a lot. It's just it never it
never gets recorded so you don't see it.
>> Right.
>> And that's a I think from the operator
standpoint that's a benefit. Like if
you've heard any public company CEO, if
their stock moves around a lot, it
creates a lot of chaos for the employees
who are owners who are wondering what it
means. This is already starting to play
out, right? Robin Hood announced they
were going to do what you just said and
and the companies, you know, threw up a
a a strong argument that that would be
illegal, like you don't have a right to
do that. So, we'll see how that plays
out.
>> Yeah, it's fascinating how all that
plays out. Or you tokenize real estate
and what effect that would have on.
>> Look, I I I think that and I've been
outspoken on this particularly around
the IPO process. I think it is insanely
unfair to the companies the way they're
forced to go through this process where
the bankers pick the price and pick the
shareholders. There's just no need to do
that. If you took a freshman computer
science student and a freshman finance
student and said, you know, imagine how
a company should go public. They would
match supply and demand anonymously like
you would in any auction. And exactly
the way a a ICO works. Yeah. With
tokenization, no one would invent this
thing where you you cherrypick your best
customers and give them this sweetheart
price. No one would do that. So, I do
think that Wall Street because they just
can't get out of their they can't let go
of this greedy power grab they have
around the IPO. you know, we we pushed
direct listings for a while, which which
uses this auction mechanism, and they
could have embraced that, but they
didn't. They've gone back to this kind
of controlled igopoly. I I think that is
an area where where tokenization like
just merely getting to the first base of
how the share should be allocated um
could be very disruptive. Stable coins
could be very disruptive too to credit
cards.
>> Well, go deeper on that. most of the
rest of the developed world, the
governments um established a an ability
to do instant transfer from bank account
to bank account and from bank account to
a partner or retailer, whatever. UK
faster payments did this 20 years ago.
Recently, Argentina did it with picks in
the past six years and it quickly became
60 70% of transactions and precisely
because of regulatory capture the banks
have kept our government from doing
that. They've the government wanted to
they have something called Fed now but
there's massive push back in the finance
committee in Washington so it never
happens and as a result you know we have
credit cards that charge two two and a
half% in a whole ecosystem of companies
that live underneath that umbrella. If
you have a Coinbase account you can put
your money in a USDC stable coin and
earn 4% and within seconds immediately
transfer money to someone else for
pennies. What is a stable coin? Like I'm
totally naive here.
>> It's a cryptocurrency that if the
company's following the regulation, I
believe that USDC is is in fact doing
that. Um where they have they have
created a dollar fordoll holding in
treasuries, US treasuries. Okay. For
each each stable coin that's
represented.
>> So that's kind of like the gold standard
back to the dollar almost.
>> Yes. But because it's on the crypto
rails which are now quite proven and
quite fast and global and immediate, it
gives you the ability for me to to give
you or for a company to give a company
or anyone um a dollar, you know,
immediately. Who holds the dollars in
this case? It's like if a bank transfers
a dollar to another bank, I I just in my
head I'm like, you know, it's it's an
electronic transfer, but in reality,
it's probably like there's a dollar
actually transferring at some point.
>> Well, no one's taking a physical cash
dollar, right? Like that's all it's all
digital anyway, right? In America, if I
want to send you 50 bucks digitally,
I've got to go through AC, which is
three-day settlement, which is part of
this regulatory capture in in
in Argentina now it's immediate because
of pics but
>> so we don't actually need the three days
we do like the regulatory makes that
happen
>> no I can I can wire to you same day but
it cost me $25 and I have to fill out a
page of forms and I might have to do a
verbal commit with my bank
>> so the way around that is stable coins
because you're really just working
around the regulation
>> same yes and credit cards which cost 2
and a half% but this there's no reason
that it should and once again
>> these other countries which include UK,
Australia, India, China, Argentina,
they've all done this but we never did
it and probably won't like I at this
point I think stable coins will get
there faster than than the government
will will be able to do it.
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>> How do you think about the competitive
mode of Visa and Mastercard? I think
they will be heavily threatened by this.
And historically what they've done in
and by the way those two companies have
two of the highest operating margins in
[snorts] the history of business. They
have like 60% operating margins and
they're they're duopies and and they
were created by the banks. So and the
banks have a stake in it. So it's like
the the whole industry is is kind of
stuck in this world where they make a
lot of money because it is this way. But
there's zero reason why it should cost 2
or 3%. Just zero. And it will change in
China because they had this digital
immediate transfer. Um Alibaba and
Tencent were able to very quickly build
digital wallets that people carry
around. And so if you walk around China,
if you want to buy a hat from a street
vendor or or a car, you know, in a
Huawei store, you you use we we we chat
pay and Alip pay for everything. You
scan a QR code like at a you check out
of a restaurant like you can just pay at
your table. There's a QR code on the
table. You just take your WeChat pay or
Alip Pay and scan it and you're done.
like one click. I so they they've
innovated their entire payment system
way further than we have because because
of this
the decision by the government to make
money transfer easy
>> and that means like no three-day
settlement sort of
>> exactly
>> and it doesn't necessarily mean stable
coin it just means
>> that's true I just think because they
waited so long in the US you know this
Fed now project's been just out there
forever that that the threat becomes
this new thing and especially with the
momentum the crypto momentum in
Washington that could change with a new
administration.
>> As you were talking about that I was
also thinking about Moody's and AI and I
was like oh Moody's you know basically
they sold analysis on debt.
>> Yeah. How do you think AI changes their
competitive position? Because like in
theory AI would be able to do that
better than or equal to Moody's which
also makes great margins.
>> Yeah. I think Moody's power comes from
the fact that um that it's a standard
and everybody trusted as a standard,
>> right? So even if they used AI on the
back end, they're still the
>> the Yeah. the the the watermark. Someone
could pop up. I mean, there's been a lot
of talk about these companies like ISS
that that that tell shareholders how to
vote. That came up yesterday
um at at the Debook Conference and
whether or not AI could solve that
problem as well. It's possible. Yeah. I
mean, I think everything's up for grabs.
>> What do you think about independent sort
of like services like that that that
profer advice on how to vote your
shares? Oh, I think in the US it's
gotten to a really bad place because of
the rise of the index funds. Um, the
index funds and this is why they're
asking Larry Frink about it at Black
Rockck like they don't the index funds
don't have the time to truly evaluate
the what the vote should be in these
situations. And so the they rely on
these services, but these services have
been built. They play this game that
that that it's not particularly um
settling, but they they score you, but
they score you with a black box. They
don't tell you how they score you,
right?
>> You and guess how you can learn more?
>> You you hire them.
>> Yes.
>> So they get paid on both sides. And it's
just it's more of a heist, I think, than
anything else. And I'm I've I've spent
some time talking to I don't know that
they they they they got focused on
issues that weren't shareholders
interest like what what's like what they
really care about is is um what what's
best for shareholders,
>> right?
>> And they got away from that. Um the the
Tesla case is a great example that that
package that type of package that they
did for Elon. I've said this, you know,
publicly. I would agree to that type of
package for every company I've ever
worked with, and most CEOs wouldn't take
it. Uh, it basically says you don't make
money unless the stock goes way up. And
if you stock goes way up, you make an
obscene amount of money. And I would do
that deal over and over and over and
over again. None of these ISS like
evaluators agree with that. like they
just in fact they take the opposite.
They say oh no that's a negative we
should vote against it.
>> Is it just because they're looking at
the headline number and they're like
that's egregious not looking at what's
required to make that happen.
>> Yeah. And they started from a place of
corporate governance where they were
looking out for fraud. And so so risk
mitigation rather than shareholder
interest. And so when you come at it
from that perspective, you're like,
there should be rules and people should
adhere to the rules and when people get
outside of the rules, that's bad.
>> Yeah.
>> I think that's their legacy.
>> What do you think are sort of the second
order effects of the rise of passive
like we've uh indexing which is mostly
post the GFC. How do you think it plays
Well, this is one of those things like
this this wouldn't be a problem were it
not for because it's the large number of
shares held by the uh the passive it one
one thing that would be really great is
if they just wouldn't vote um because
then the people that are active
shareholders would have more of a say in
what happens with these companies but
there's they own such a large
percentage. Um
>> there's also an argument that they
should have to vote in the same
proportion that direct holders vote.
Yeah. Well, if they didn't vote, that
would happen just by natural because the
the vote would just be it'd be more like
how unfortunately how voting works in
America where you only have like a 20%
turnout. But
>> the second order factor that like I
could have control of the company with a
very small share of
>> Yeah. At first, I think the public
investors got really scared because they
were marked to the index and they ended
up doing what people call closet
indexing to make sure that they didn't
>> um lose out. And like when the MAG 7
took off, um if you didn't own those,
like you had a bad year, as an example,
and so you're forced to kind of closet
index. But they were they had kind of
reached a point where they think the
number of active investors is so few
that the ability to get an edge has
maybe increased as a result of the of
the massive indexing.
>> Do you believe that?
>> I don't know. I mean it's it's the buy
side is a very hard job like to to beat
the S&P. Some people have even
highlighted the fact that, you know, QQQ
has probably outperformed 80 or 90% of
venture funds.
>> One of the surprising things that I
learned about you through reading your
book was that you love the craft of
storytelling and writing.
>> Yeah.
>> Talk to me about what you've learned
about storytelling over the years and
because that's really important to
founders. It's really important to
anybody trying to get a message out in
today's world. Someone asked me like the
top three traits of founders that are
successful and I put storytelling in
there. Um the the there's another thing
that happened you know when I prior to
going to business school I didn't read
much but some bit flipped when I was in
business school. I started reading and I
I started with business books that most
people know. Um, I got into personal
development books, which I find a lot of
successful people have this moment in
their life where they roll through, you
know, Dale Carnegie and like like Seven
Habits and stuff like that. Um, and then
and then biographies.
>> Um, but but after that, I I I've kind of
fell in love with with long form
non-fiction journalism that reads in an
exciting way. And part of it was the
wave that was Malcolm Gladwell and
Michael Lewis and John Crockower and
those books that read like fiction, you
know, even though they're non-fiction.
And there's actually multiple books
written on that art. It's called the new
journalism and the new new journalism.
And I've read those books about that
writing. And I just find it super
powerful that someone can maybe put
together 20 pages that like really
impacts you in a certain way. And so I
started studying the craft, studying
Buffett and Howard Marx and seeing these
investors that were successful like
putting their stuff out there. If I was
thinking through a problem about a new
most of my most successful investments
fall in this category people call
marketplaces and before there was a
first marketplace like there wasn't a
knowledge base and you know we crafted
that along the way and codified it and
wrote it down and that in addition to
helping you think through all the corner
cases and this is exactly why Bezos has
his six-page letter concept at Amazon.
He he believes that if you have to write
it out and make it stand alone and be
cogent that you'll think through more of
the the problems and you'll it'll be
more cohesive and it'll it'll um you
you'll figure out the loose ends and
you'll tie them up. Um, and but in
addition to that, in the venture world,
for the founder that doesn't know you,
when they see your knowledge on a
subject or they see what you're talking
about in their own business, they reach
out to you. So, it becomes a calling
card.
>> It's like a magnet.
>> Yes. Yeah. And I I'm not the only one
that's done it. A lot of people have
done. And some people don't use that
technique. There's other ways to to get
deal flow, but it's powerful if if you
do it right.
>> You mentioned storytelling. What are the
other uh you know chosen unfair
advantages that founders have? You said
there was three.
>> Oh, right. I have a fourth one. I hope I
can remember it. I think product
instincts is another one that that that
comes partially from understanding the
new edge which we already talked about
but like it probably took my whole
career for me to fully understand how
hard it is to hire someone who's not a
product first individual and then get
them to be good at it. I'm sure there
there are examples, but it's got to be
5% or less of the use case. super hard.
>> Um um so uh storytelling is so important
because
in the founder case, you're recruiting
employees, you're you're you're
recruiting executives, you're raising
money, you're closing customers, you're
closing partnerships, you're selling all
the damn time. Yeah.
>> And the best ones are just super
effective at it. Um and you can see it
with Bezos. You can see it with like
Toby at Shopify. I mean, God, like,
listen to any Toby podcast you possibly
can. Like, of course, the world's going
to follow this guy, Daniel E. Like,
they're just so gifted at describing
what they're trying to do, you know, and
that's that's just just, you know, super
super valuable. I once asked Jeff Bezos,
"How have you had such a successful
angel portfolio? You don't have any free
time." And he says, "Oh, when I meet an
entrepreneur, there's only one thing I
ask myself. Is this person gonna do this
no matter what? Come hell or high water,
they're doing this. Like, they're just
already convinced that this is so
important, they're not going to stop.
And I think that level of determination
is present in all the great founders.
Like, they're just going at it, you
know, full blast.
What are the what are some of the real
world lessons you learned while working
with Uber that you wouldn't find in like
an HBS case study?
>> Well, that that's that's an easy answer
to get to quickly. Although now uh
[snorts] because I had I had a moment in
my brain where where that exact phrase
you just said popped into my brain. We
were, you know, in a situation where I
think most people that were investing in
the category knew it had winner take all
dynamics and network effects. And as a
result, there was this determination
that they were just going to have to
fund it kind of ad nauseium. And you had
a situation where the burn rates, you
know, where okay, well, someone's hands
lift a billion dollars. Well, then we
get handed three billion. And so, and
and and once again, the only way to
compete in that world is to spend that
money. And so, you have these burn rates
that are bigger than any pro public
company would ever spend going after a
new category. And and so aggressive. And
I thought to myself, at the moment, um
there is no HBA case study. You could
take the board members from Walmart and
Costco and GM and and General Electric
or whatever you consider the top 10 best
companies and they would have never been
in this situation before. So there was
no there was no one to call. There was
no there's no mentor to go find. Um
which was uh horroring a bit to
recognize you're in that situation. But
now all the AI companies are in that
situation. So, I uh I feel for him.
>> Uber was kind of the first in the in the
>> in the mega burn. Yeah. I mean, well,
Amazon was, you know, they they had a
big burn rate, but then Uber took it to
a new level. Um, but now it's at a
they've added a zero. [laughter]
>> I'm curious from the like how Benchmark
was structured on the inside and how
that structure contributed to its
success.
>> I've talked about this a lot. I I was
very fortunate to get invited into
Benchmark. I was I I joined on the third
fund so I wasn't there early. Um they
had left the founders of Benchmark had
been at hierarchical firms where they
felt like the senior patriarchs were
maybe taking too much of the money and
too much of the credit and not doing the
work that was imperative for the firm's
success. Um most partnerships, you know,
you think law partnerships or accounting
firm partnerships work in a way where
the the senior people have more power
and take more of the economics and the
junior people have to work their way up
over a long period of time. The founders
decided at Benchmark that they were just
going to make it equal, an equal
partnership. And there's no there's no
lead partner, there's no king, there's
no president, there's just
five equal partners.
>> So what are the second and third order
consequences?
>> There's a bunch of them and I think most
of them are positive. The first thing is
it makes it very easy to recruit
exceptional talent from other firms
because they're not in that situation
and you immediately and I was at a firm
that was hierarchical and you know even
if you went back and said well I'm going
to leave to go to this equal partnership
and they said oh we'll make you equal
well you did it because I was leaving
not because it works that way
>> right
>> that's one the second one is it really
encourages development of the new people
that come in because I'm going to take
an equal part of their success when they
start delivering. And so I'm not I want
them to be super successful and I'm
going to spend time and and I boy on my
way in I felt that like I just felt like
you know and the type of support it if
you're in a up or out firm I bet it
feels kind of lonely. I bet you know
you're competing against that person
over there. Are you going to share ideas
with them? Maybe, maybe not. Like, and
in this equal partnership, you know, if
one of my companies needs a new CFO and
they know of one, they'll probably just
give it to me right away. My company
succeeding is no different than their
company succeeding. So, you just create
a a different dynamic. And you don't
spend any time annually on comp review
and recutting the pie. You don't like
it's all it's always equal. it's always
going to be equal like that that amount
of political overhead just goes away. It
there is there's one huge negative. So I
don't want to just say it's all um the
it's almost impossible to have uh
because you don't have a CEO. It's hard
to scale out and it's hard to have new
initiatives like because there's no like
oh maybe we should you know the website
was always a funny one like who's going
to own the website? Well, are we going
to hire, you know, someone to do that?
And well, who owns that responsibility?
>> Yeah.
>> And when Matt Kohler came in, he had
he's like, "Oh, man. I'll take it on. I
love I know exactly what we need." He
created this super complicated website
and it had all the founders on it and
now they're connected to all the
partners and and people started
complaining because stuff wasn't right.
And one day, Mac came in [laughter]
and uh he said, "You know what? I'm
taking it all down and I'm putting up a
splash page. And he did that. He did
that like I don't know 15 years ago. And
still today, Benchmark has a single
page. And that's a result of this issue
that I'm describing.
>> Well, you know, it's interesting you say
that because I find a lot of websites
have such a high cognitive load to use a
splash page with like, you know, four or
five sentences or Berway's website. I
totally get it. I don't there's not a
lot of cognitive like [laughter] if I
you know I heard this example um from a
guy a couple weeks ago. He's like if I'm
going to buy a sweater I don't want to
know your mission statement. I don't
want [laughter] like I just want to buy
a sweater.
>> There's a little bit of bespoke
confidence in in just having a splash
page. I would just add that there are
plenty of highly successful venture
firms that aren't structured that way.
And so I don't it's not I'm not saying
it's the only way to do it. It's clearly
there clearly many ways to do it
>> in a world of wash with capital.
What makes a founder choose Benchmark or
somebody else? Like what goes into that?
>> First of all, at a high level, if you're
successful as a venture capitalist,
people want to work with you. you know,
when I came in, you know, the Mike
Moritz, you know, John Door, like
they've had so much success that that
not only, you know, is it likely that
they
>> are are great at what they do and know
people that will help your company
succeed, but their stamp of approval of
you will carry weight in and of itself.
And so there some people have said it's
the only investing category where there
are network effects because once you
have a reputation it it you have an
unfair advantage in deal flow.
Underneath that I would I would say
founders are particularly
um motivated
to be around people who understand what
they're doing u and are excited by it
and excited about it. And one of the
reasons young people can break into
venture and be wildly successful is
they're much more likely to be the age
of the founder, they're much more likely
to feel
someone that understands what they're
doing with with many of these
technologies that are new. They're much
more likely to understand them. And you
know, I I've used examples describing
this in the past, but let's say you're a
really into esports or something. You
you it would be very easy to know more
than the successful generalist venture
capitalist in that category.
>> Yeah.
>> Like you could very quickly know more.
And that could be true of of
YouTube video creations. Like it'd be
very easy for a young venture capitalist
to know more about what it takes to be
successful on YouTube than John Door or
Mike Moritz or me or whoever. Like
because you could just go spend 100% of
your time on that. So, so in that way,
is it sort of like athletics where you
you age out in a way and you're
competing against younger people who
know or understand a niche better or how
>> I I I think the the whole industry bends
towards youth for that reason and
because it's a hustle business like
there there's there's always a rock you
haven't looked under and you know age
brings children and homes and and and
other requirements you get tied to and
responsibilities and you're just not
able to go spend 80 hours a week
studying YouTube like you just can't.
>> Um so I think it bends towards youth. Um
which is great like like it's a it's a
highly competitive industry. It's hard
to get a job but if you get one there
are reasons why you can break in.
>> We always end with the same question
Bill which is what is success for you?
>> I think I think it's changed over time.
I would say when I look back on my
venture capital career, I made a
decision, a very specific decision to
say, "Okay, I'm done." And and I I don't
think I would have done that if I felt
there was work left to do. I think I
reached a point where I felt there
wasn't any work left to do. So, in that
case, you know, that was my dream job. I
was thrilled to do it. I loved every
minute of it. I often said that I would
if we lived in a socialist society and I
everyone had to work for free, I would
still take that job. Um or the same fe
salary or whatever. Um
>> might not be eating, but you'd be
>> Yeah. But that's now done. And so as I
look forward, you know, I was very moved
by this book Arthur Books wrote called
Strength to Strength to Strength where
he talks about this next chapter in your
life. I would like to take some of the
techniques that I use to be successful
as a venture capitalist mostly around
the blog and understanding problems and
synthesizing and see if I can apply
those techniques to bigger broader
problems in society and see if I can
dent the universe a little bit that way.
>> I love it. I wish you luck.
>> Yeah, me too. Me too.
>> Thank you so much for taking the time.
Thanks for doing this. It's great.