March 9, 2025

E144: How the World’s Top Investors Compound Their Advantages

E144: How the World’s Top Investors Compound Their Advantages
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In this special solo episode of How I Invest, I break down one of the most powerful forces in investing: compounding. Over the course of 142 episodes, I’ve discovered that the best investors all leverage compounding—not just in their portfolios but in every aspect of their business. From relationships and reputation to proprietary information and top talent, compounding creates exponential advantages in a hyper-competitive market.

Highlights:

Compounding Beyond Capital: The biggest investors understand that everything compounds, including reputation, diligence, and deal-making experience.

The Power of Relationships: Trust compounds with each deal, leading to faster and more efficient decision-making.

Reputation as an Asset: Warren Buffett’s ability to negotiate superior terms stems from his compounding reputation as an ethical and skilled investor.

Proprietary Information Loops: Access to unique insights leads to better investments, which generate even more privileged information.

People as a Compounding Advantage: The best organizations attract and retain A-players, who in turn recruit other top talent, creating a self-reinforcing cycle of excellence.

The Arbitrage of A-Players: Paying A-players above market rates is a competitive advantage, as they generate exponentially greater value.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (0:21) The role of compounding in investing and relationships (2:13) Trust bias, deal-making efficiency, and reputation effects (4:23) Proprietary information and the compounding of talent (6:50) AI's impact on productivity and compounding (7:49) Closing remarks
Transcript
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Welcome back.

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For episode one fifty, I wanna do something
completely different and record my first solo

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episode.

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But just like with my New Year's resolutions, I
don't really believe in waiting for an

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arbitrary date to do something.

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So, alas, I'm releasing this as episode one
forty three.

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If you enjoy it, please let me know by sharing
this episode with a friend, which lets us know

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that you value the content.

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Let's dive right in.

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Across the first hundred forty two episodes,
the one consistent component I found across all

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top investors is the role of compounding in
their business.

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Today, I'm gonna cover how the world's top
investors compound their advantages in a hyper

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competitive capital markets.

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Lesson number one, when it comes to
compounding, is that everything compounds when

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it comes to investing.

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Whether you're investing someone else's money
or your own, even areas that appear not to

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compound.

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Most investors assume that going from one
investment opportunity to another is a linear

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exercise.

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But in reality, it is a compounding exercise.

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Your reputation compounds, your experience
compounds, your ability diligence compounds.

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All these skills compound and stack on top of
each other from one deal to the next.

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That being said, while some things compound
exponentially, others only incrementally.

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What compounds exponentially?

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Above all else, relationships compound
exponentially.

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This is both for obvious as well as non obvious
reasons.

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Relationships compound because, of course,
doing the second deal or the third deal with

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somebody is much easier than the first deal.

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On the first deal, your counterpart needs to
diligence both the deal at hand as well as you,

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the individual.

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When you get to the third deal, the diligence
at that point is almost entirely based on the

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deal presented, not on you as a counterparty.

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The implicit difference here is trust, which is
why trust compounds within relationships.

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When you present a second deal, you're much
more trustworthy than when you had presented

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the very first deal.

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By the time you present the third deal, there's
almost an automatic trust in the relationship

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and embedded trust in the diligence process.

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Of course, capital allocators will rarely admit
this and may not even be aware of this, but

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indeed a bias of trust is present.

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This trust bias is a heuristic or a mental
shortcut that serves to save investors time.

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Before you go about criticizing this behavior,
keep in mind that when psychologists studied

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people's behaviors over many decades, there was
consistency as it relates to ethics.

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Just take a moment to think about someone that
you've known for twenty years.

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Have their ethics changed dramatically?

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I would venture to guess that although their
skills and maybe even their lifestyle has

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changed dramatically, their ethics have
remained consistent throughout the twenty years

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that you knew them.

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There's another reason why relationships
compound exponentially, and that is because of

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the familiarity between parties.

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What does that mean?

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Once you've done enough deals with a
counterparty, you have an implicit

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understanding of how the other side looks at an
opportunity, how it fits into their overall

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portfolio, and the kind of deal terms they care
about.

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You essentially start with half of the deal
cake already baked.

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The next factor that compounds exponentially is
reputation.

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Reputation compounds when it comes to
investing.

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Teddy Roosevelt once said, reputation is what
people say behind your back.

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Reputation can be a key advantage when it comes
to investing.

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This is the number one reason why Warren
Buffett is able to negotiate superior terms on

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his investments, both because of his reputation
as an ethical counterparty and as his

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reputation as a great investor.

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This is so much the case that every deal that
he's worked on has been kept extremely

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confidential, lest it increase the price of the
stock before the deal is ever announced.

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The opposite, of course, is also true.

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Negative reputations compound exponentially.

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Institutional investors oftentimes do a minimum
of 10 reference checks on a potential manager

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prior to investing, making it nearly impossible
to raise institutional capital if you have a

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bad reputation in the market.

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This is why, sadly, many investors will never
raise a single dime of institutional capital.

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The next factor that compounds exponentially is
proprietary information.

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This compounding factor is less obvious versus
the other ones.

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There's a significant compounding effect when
it comes to proprietary information.

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This is because proprietary information leads
to higher returns, which leads to improved deal

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flow and turn leads to additional proprietary
information.

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This is a virtuous cycle.

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This is why some families are able to preserve
their wealth for many generations, especially

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in poor countries where information is more
concentrated and limited to a small group of

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powerful individuals.

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This can even be the case when the next
generation is not as hardworking or even as

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intelligent because proprietary information can
beat that much of a competitive advantage.

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It becomes exponentially easier to make good
decisions when you have access to proprietary

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information.

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One does not need to be a genius to buy land in
an area where there's a recently discovered oil

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field that few people know about.

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The same goes for buying secondary in a private
company that you know is doing well.

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The next factor that compounds exponentially is
people.

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People compound exponentially.

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Every CEO says, our most important advantage is
our people.

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But if you don't have policies in place that
lead to attracting and retaining the very best

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people, this statement is simply window
dressing.

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How do you go about attracting and retaining
the very best people, the a players?

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Firstly, a players want the ability to develop
skills and develop their own value in the

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marketplace.

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This could be a difficult pill to swallow for
insecure managers.

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Insecure manager may think, what happens if I
develop my a player and he or she leaves my

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organization?

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The answer is that if you don't develop your a
player, they are guaranteed to leave and likely

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sooner than later as they have many options.

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To the upside, having a fully developed a
player for three years is more valuable than

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having even an equivalent a minus player for
ten years.

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So many ways developing a players is the price
for having a great organizations.

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A players will recruit other a players at your
organization.

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A players are the most underrated recruiters on
the planet.

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That is because a players wanna work with other
a players.

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Conversely, a players serve as a very effective
quality control for the business.

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A players have zero tolerance for even a single
b or c player on their team as they realize

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that one bad apple can significantly hurt the
entire team and organization.

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This is why as investor, even with a small
investment team, you could argue that your

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number one job is to make sure that you attract
and retain a players.

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A players are the ones that will create the
organization that leads to sustained alpha and

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performance.

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The arbitrage when it comes to a players is to
pay them 10 to 25% over their market rate.

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This is a competitive advantage in both
attracting and, perhaps most importantly,

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retaining a players.

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The reason you can afford to do this is because
a players will produce an order of magnitude

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more and higher quality output than even a
minus players, leading to overall savings.

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This arbitrage will only continue to grow as
productivity increases with the advent of AI

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and AI tools.

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And that's the lessons I've learned through the
podcast and also in my career on what compounds

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exponentially.

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Einstein famously said that compounding is the
eighth wonder of the world.

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What do you think?

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Do you agree?

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Thanks for listening to my episode on
compounding.

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If If you enjoyed this episode, please share
with a friend.

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This helps us grow and also provides the best
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Thank you for your support.