We Study Billionaires - The Investor’s Podcast Network - TIP179: Private Equity Investing w/ Doug McCormick (Business Podcast)
Episode Date: February 25, 2018On today's show we talk to private equity investing expert, Doug McCormick. Doug has been a private equity investor for two decades and his company has assets under management in excess of a billion d...ollars. IN THIS EPISODE, YOU’LL LEARN: How does the private equity model work? What happens when a private equity company makes an acquisition? Why has private equity industry outperformed the stock market and will it continue? Which critical factors determine if a takeover is successful or not? BOOKS AND RESOURCES Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, and the other community members. Douglas McCormick’s book, Family Inc. – Read reviews of this book. Doug’s website with free financial tools. Raymond M. Kethledge and Michael Erwin’s book, Lead Yourself First – Read reviews of this book. NEW TO THE SHOW? Check out our We Study Billionaires Starter Packs. Browse through all our episodes (complete with transcripts) here. Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool. Enjoy exclusive perks from our favorite Apps and Services. Stay up-to-date on financial markets and investing strategies through our daily newsletter, We Study Markets. Learn how to better start, manage, and grow your business with the best business podcasts. SPONSORS Support our free podcast by supporting our sponsors: SimpleMining Hardblock AnchorWatch Human Rights Foundation Unchained Vanta Shopify Onramp Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm
Transcript
Discussion (0)
You're listening to TIP.
On today's show, we talk to a good friend and fellow West Pointe and Harvard grad, Doug McCormick.
Doug is a partner in a private equity firm that has conducted countless deals across
two decades buying and selling companies.
And what I think you're really going to enjoy about today's show is the perspective on
valuation and how to think about buying businesses with an enduring competitive advantage.
Doug is one of the smartest people I know when it comes to investing in capital allocation,
so I have no doubt you're going to capture a lot of value hearing his thoughts on the industry.
So without further delay, here's our discussion with the thoughtful Doug McCormick from HCI Equity Partners.
You are listening to The Investors Podcast, where we study the financial markets and read the books that influence self-made billionaires the most.
We keep you informed and prepared for the unexpected.
All right, so how's everyone doing out there?
We've got our special guest here with us. It's Doug McCormick. And Doug, thanks so much for coming back on the show. We had such a great time the last time we talked with you. So we're excited to have you back. Glad to be back and had a lot of fun last time as well. Not as much fun as the Warren Buffett annual meeting, but still a lot of fun. Hey, since you bring that up, we've got a group. We're going out there again this year and we're really excited about the event. Tell the audience quickly about the event. Since you brought this up, what kind of
stands out in your mind about why a person should go to this because there's a lot of people
that listen to the show, they hear that it's fun. But like from your vantage point, Doug,
what did you get there going out to the meeting? Yeah, well, first of all, I would say this is,
it, it's a very big, very well-attended event. And I think having a chance to go with you guys
because you guys know the whole circuit, you know, where to go, where to stand in line, how to get
good seats. So first of all, if you're going to go, you got to go with you because you
you guys got it wired. So that would be the first thing. The second thing I'd say is, listen,
I think it's a chance to see history. No other investor has been as successful as Warren Buffett
and he's not going to be around forever. And just to be able to watch he and Charlie think and respond
to questions was absolutely amazing. And then the social stuff is equally good. So it was a thumbs up
event all around. Yeah. Let's go ahead and dive into our questions here. So we're talking about private
equity and you've been in this space for a little bit and you understand it quite well. And so I'm
really excited to have you kind of teach our audience some of the things about private equity because
people hear this terminology. And for a lot of young people, maybe just fresh out of their undergrad
or something like that, they hear private equity, but they really have no idea what that means.
So if you could just give us a simple definition, kind of what you think when you hear private
equity. And then if you could share how you got into the space, that might be interesting for
some people. Sure. Sometimes describing it's almost easier to talk about what it isn't. So,
you know, very simply put, private equity refers to making investments in equity securities
in companies that are not listed on the exchange like the NASDAQ or the New York Stock Exchange.
If you want to list on an exchange, like one of those, there are a number of criteria. You've got
to meet regarding financial performance, liquidity, governance. And essentially, these requirements
ensure that there's enough interest and information in the marketplace to have a liquid market.
So private equity investors are essentially pursuing opportunities that don't meet these size,
liquidity, or information or governance requirements.
And as a result, you see some very different attributes in these kind of investments.
So I think there are five worth noting.
The first is lack of information.
So there's no equity reports, no published financial statements.
you're really making decisions only on the diligence that you've done as buyer and the information
that's been shared to you by the seller.
And so that makes underwriting much more difficult, but it also makes for a much less efficient
market.
So that's kind of one key difference.
The second is everything's negotiated.
So when you think about a public market, all the terms of an equity offering or a debt
offering are set, and the investor determines the price.
In a private equity situation, you're negotiating not only the price, but you're negotiating terms and conditions, things like governance, things like interest rates, if it's a contractual return, et cetera.
The third would be governance.
These type of securities are often take a while to get into.
They take a lot of work.
And so private equity investors generally buy a meaningful portion of the company.
So a minority or a majority stake.
And along with that significant portion comes.
some level of governance or control or influence. The fourth would be duration. On average, I think
private equity investors expect to be in their investment for five or six years. Compare that to,
you know, average whole period on the New York Stock Exchange is well under a year. So I think those are
those are the four biggies. So, Doug, we hear about private equity in the news all the time,
and you also hear about venture capital. So could you please explain the differences and the
similarities between the two? Yeah, so I actually think the way I would describe it is I think venture capital
is a subset of private equity. So private equity are all things not listed on exchanges like we just talked
about. And then within private equity, you have growth equity, which is a business model that's
been established, but looking to really scale. You've got venture capital, which is a lot of the early
stage stuff that we think about in Silicon Valley. And then you've got things like leverage buyout,
which are big mature businesses, and often because they're mature, they can afford to be financed
with debt. And then you've got a bunch of other smaller kind of niches like turnarounds,
like mezzanine financing, which is private debt capital. But all of those strategies kind of
play in the overall private equity asset class. What would you say for this space, where do you
think most private equity people dwell? Like, what kind of market cap? That's really interesting.
So first of all, it's a classic conversation around means and medians, right? So if you think about means, the averages are skewed to the very big, and there's some very big private equity firms out there, KKR, Carlisle, Blackstone, for example. And they would be dealing with very, very large companies, billions of dollars in enterprise value. Having said that, there's probably about 4,000 private equity firms out there. And if you look at medians, most of those private equity firms are focused on much small.
businesses, like good American businesses that are not in urban areas, but are a critical
part of today's economy. And those have, you know, kind of enterprise values well under
100 million. We talk about enterprise value a lot in the public markets when we talk with
Toby Carlow and Stig and I use that as one of our main metrics for filtering results and
trying to find the best undervalued picks is using the enterprise value to the EBIT. I'm curious,
Is that how you typically look at things from the private equity side?
Are you looking at enterprise value a lot versus just like the value of the common stock?
Absolutely.
We look at enterprise value relative to metrics of cash flow.
And depending on the business, there may be slightly different metrics to look at.
But to your point, enterprise value to EBIT, I think is probably one of the most important.
And essentially, enterprise value allows you to think about the value of the concern absent capital structure.
Could you please elaborate on that, Doc, because it goes into the debt structure of the company
and why it's such an important starting point to have?
Yeah, well, I think, you know, as we talk about the big landscape of private equity,
and we talked about leverage buyout as one of those, and so those are more mature businesses,
more stable businesses.
One of the ways that that part of the asset class drives returns is they finance the transaction
with a significant amount of debt.
And, you know, I would argue it's often appropriate because those businesses are
slower growth businesses, but more mature, less earnings volatility. And, you know, the analogy I
would make is it's the same analogy as buying a house. You know, if you bought a house with no financing
and the house appreciates 10%, your equity went up by 10%. If you, you know, bought a house with 90%
purchase price financed with debt, the house goes up by 10%. You've doubled your equity money.
Same concept in financing leverage buyouts. And there are numerous benefits to that. The first we talked
about is, you know, you leverage your equity investment. The second is you're providing a cheaper,
lower source cost of capital. And then the third is there are tax deductibility issues with interest.
And so when you add all those things together, it can really help drive attractive returns for
that part of the asset class. So this is my impression of private equity is that it's grown a lot
in the last couple decades. And that might be true or false. I'm kind of curious to hear your
thoughts on that. But if it is true, why has that occurred and why has this become such an
attractive asset class for investors? No doubt about it. This asset class has experienced tremendous
growth. So if you define the asset class by assets under management, AUM, in the 2000 time frame,
the entire market was about 600 billion of assets under management. And today, that's approaching
two and a half trillion. So, you know, kind of a 4x growth here. And as I mentioned,
there are now 4,000 firms approximately in this market space. Very simplistically, I think the number
one reason the asset class has grown is it's been an attractive returner. You know, there's lots of
firms out there that estimate what the kind of market return looks like for the asset class.
And most reports would say that the private equity asset class has returned, you know,
three to 400 basis points in excess of a broad equity indices. So if the Russell is doing 10% on a long-term
basis, private equity is kind of done 13 or 14 percent. So I think that's the number one reason
things have grown. And as you kind of think about why private equity is interesting or why it's
performed well, a couple comments. First of all, it should, right? This is a very illiquid asset class.
There are risks associated with being the asset class. So if it's not returning better than the
public equity markets where you can turn around and sell tomorrow if you don't like the way
things are going, then it's not going to be a smart investment. But I think at a very high level,
there are some things that make this asset class sustainably attractive. One is the overall
supply and demand equation. There's a lot of capital out there. And there's certainly a lot of
capital that's come into this market, but it's also a very big fragmented market in terms of
where this money can go reside in terms of the deals. And so I think the supply demand equation
has been favorable to private equity.
I talked about the inefficiency of this market in terms of there's no information out there,
and that makes it very challenging to get good deals done,
but it also creates real opportunity where we think you can find real value
because of just the inefficient nature of information.
Another aspect of why this is such an interesting asset class is it actually solves real problems.
And what I mean by that is when you're trading stock in the market,
It's buyer and seller directly as a secondary share, and the company is really not a participant
in that transaction. When you think about private equity, you are solving a corporate finance need.
A company needs capital to grow, and they're raising capital from you, or a founder or an owner
needs capital to execute a succession plan or a consolidation strategy. And in all cases,
I think those are win-win scenarios, not just buyer and seller where one wins and one loses.
So I think that's a big contributor as well.
So if we have this one scenario where you as a private equity company would go in and
just outright buy the other company and you will just get all that net income back to you,
basically everything would be business as usual and you won't really interact with that
company.
And then the other scenario where it would be completely opposite that the private equity company
would go in, send all the experts, perhaps even change the management.
and basically not only look at the strategy, but also all the nitty gritty operations.
What are we closest to are those two scenarios if you have to say what a typical case would be like?
As you think about, we just described how this market's experienced tremendous growth.
And as it's experienced tremendous growth, it's matured a lot as well.
And so, you know, I generally break it down into three stages.
When people first started doing this in the 70s and the 80s, the real value of driver was price,
price discrepancies, real discounts to the public markets. And then in the 80s and 90s, a lot of
the value was driven by leverage, and you were able to get much higher leverage reads at that point,
and so you could finance a much greater percentage of the deal with cheap capital. And in today's
market, I think both of those two previous sources of value have been kind of commoditized, if you will.
And to be successful, you've got to be a really good underwriter, which means you need to specialize
in certain industries where you have a competitive edge.
And then you've got to figure out how to drive value or do something different with that
asset over time.
And so lots of firms have developed different strategies for that.
But common strategies are bringing operational expertise to the party or bringing unique
industry expertise to the party so you can really help grow the business.
And so I think to a certain extent, organizations are evolving to be strategic buyers.
You know, they come at it from a financial perspective, but they've got to bring more
than capital to be successful. Interesting. So I would imagine that you'd see a lot of private equity firms
really specialize in certain niches. Is that true? Yeah, I think it's specializing in niches or
specializing in a business model. So you can define your core competency as we know everything about
aerospace and defense. You could define your core competency as we know certain types of business
models, distribution, transportation, let's say, or you could define your core competency as, you know,
we have operational capabilities to drive, you know, enhancements and operations. Let's take a quick
break and hear from today's sponsors. All right. I want you guys to imagine spending three days in
Oslo at the height of the summer. You've got long days of daylight, incredible food, floating saunas on the
Oslo Fjord, and every conversation you have is with people who are actually shaping the future. That's
what the Oslo Freedom Forum is. From June 1st through the 3rd, 2026, the Oslo Freedom Forum is entering
its 18th year bringing together activists, technologists, journalists, investors, and builders from all
over the world, many of them operating on the front lines of history. This is where you hear
firsthand stories from people using Bitcoin to survive currency collapse, using AI to expose
human rights abuses, and building technology under censorship and authoritarian pressures. These aren't
abstract ideas. These are tools real people are using right now. You'll be in the room with about
2,000 extraordinary individuals, dissidents, founders, philanthropists, policymakers, the kind of
people you don't just listen to but end up having dinner with. Over three days, you'll experience
powerful mainstage talks, hands-on workshops on freedom tech, and financial sovereignty,
immersive art installations, and conversations that continue long after the sessions end. And it's
all happening in Oslo in June. And it's all happening in Oslo.
If this sounds like your kind of room, well, you're in luck because you can attend in person.
Standard and patron passes are available at Osloof Freedomform.com with patron passes offering
deep access, private events, and small group time with the speakers.
The Oslo Freedom Forum isn't just a conference.
It's a place where ideas meet reality and where the future is being built by people living it.
If you run a business, you've probably had the same thought lately.
How do we make AI useful in the real world? Because the upside is huge, but guessing your way into it
is a risky move. With NetSuite by Oracle, you can put AI to work today. NetSuite is the number
one AI cloud ERP, trusted by over 43,000 businesses. It pulls your financials, inventory,
commerce, HR, and CRM into one unified system. And that connected data is what makes your
AI smarter. It can automate routine work, surface actionable insights,
and help you cut costs while making fast AI-powered decisions with confidence.
And now with the Netsuite AI connector, you can use the AI of your choice to connect directly
to your real business data.
This isn't some add-on, it's AI built into the system that runs your business.
And whether your company does millions or even hundreds of millions, Netsuite helps you stay ahead.
If your revenues are at least in the seven figures, get their free business guide,
demystifying AI at Netsuite.com slash...
The guide is free to you at netsuite.com slash study.
NetSuite.com slash study.
When I started my own side business, it suddenly felt like I had to become 10 different people
overnight wearing many different hats.
Starting something from scratch can feel exciting, but also incredibly overwhelming and lonely.
That's why having the right tools matters.
For millions of businesses, that tool is Shopify.
Shopify is the commerce platform behind millions of businesses.
around the world and 10% of all e-commerce in the U.S. from brands just getting started to household
names. It gives you everything you need in one place, from inventory to payments to analytics.
So you're not juggling a bunch of different platforms. You can build a beautiful online store with
hundreds of ready-to-use templates, and Shopify is packed with helpful AI tools that write
product descriptions and even enhance your product photography. Plus, if you ever get stuck,
they've got award-winning 24-7 customer support.
Start your business today with the industry's best business partner, Shopify, and start hearing
sign up for your $1 per month trial today at Shopify.com slash WSB.
Go to Shopify.com slash WSB.
That's Shopify.com slash WSB.
All right.
Back to the show.
Talk to us a little bit about the negatives because I think a lot of people that would hear this be like, wow, you're getting 3% more than the public markets. This sounds like a lot of fun and really interesting stuff. But like what are some of the negative sides of private equity that I think a lot of people maybe don't think about or miss?
Lack of liquidity, right? So these are generally 10 year limited partnerships. And so, you know, the duration between the time you invest your capital and you get.
it back is going to be a very long period of time. So you kind of got to be comfortable with
parking this money for a long time and not expecting to get at it. And if you do need to get at it,
in many cases, you're taking a significant discount to avoid that illiquidity. The second thing is,
we talked about this inefficiency in the market, lack of transparency. That also exists in
terms of trying to find investments as a retail or an individual investor. And that's good news and
bad news, but it's very hard to identify good deals. And candidly, it's very hard to identify good
teams. So if you think it's challenging to underwrite a business where you can see the business,
you can see the financial performance, and you can evaluate the businesses and performs today,
imagine trying to underwrite a team that's going to invest in those kind of businesses,
and you're trying to evaluate consistency of strategy, quality of team, teamwork, team's ability
to source deals and add value. And so that's a challenging process as well. The last thing I would tell you
about the market is, I think averages are deceiving. And what you see in the market, I think it's one of
those markets where persistency of performance is very high. And what I mean by that is if you look at
the public markets and you look at top quartile performers in a period, let's say a year or five years,
and you compare that to top quartile the next period, the pull through between high performers
in both periods is often relatively low. But in the private equity space, you see persistence where
if you are top performer this period, you are likely a top performer in the next period.
And I think that's indicative of an inefficient market. But what I also think that means is it's
very hard to identify good managers and it takes a long time and a unique skill set to do that.
Is that because they just get a bit of deal flow?
think it's they get better deal flow success perpetuates success and I also think they continue to
develop their skill sets and their capabilities and you know this is an area where you're not just
competing on capital you're competing on human capital right so I think a lot of times at least in
the market that I'm in which is the lower end of the middle market entrepreneurs are not only picking
capital solution they're picking a partner and as they evaluate a partnership they want to work with
people they like, people that they're aligned with, and also people that they believe can help
them build a better business.
So I know if I was young and I was listening to this, and let's say I had $50,000 in my pocket,
I'd be wondering, how can I invest in something like this?
Like how is that possible?
And is it possible?
I'm kind of curious how you see that.
Yeah, it's absolutely possible.
And I think it's a mixed bag, candidly, but there are a number of very large private equity
firms that over the course of the last decade have gone public. So KKR, Carlisle, Blackstone, Apollo,
I think all those four are public now. And so you can participate by buying and equity interest
in a business that's investing in private equity. There are also ETFs out there that are
investing in those kind of businesses. So that's an option. We started off the conversation by talking
about what a great time we had at the Berkshire Hathaway annual meeting. I would argue in many ways,
you know, Berkshire is a private equity holding company, you know, so you think about some of the
big assets that they own and have bought, Burlington, Northern, Heinz, Geico, I mean, those essentially
are private equity plays, and so that's an interesting way to play private equity. And then,
you know, I think there are some ways that individuals can play directly, not through a private equity
investment professional, but lots of angel investing networks out there. I think investing in real
estate in some ways is a private equity play. And then many of us are involved in families that have
family businesses. And to some degree, that family business is private equity interest.
So you've been in this business for a long time, Doug, and you both seen the successes and also
the less successful ventures. So what would you say if you could come up with the common
denominator of what separates the good deals from the bad ones? Yeah, so I guess the first thing I'd say
is if anybody's been in the business a long time and they're not talking about both
their good and bad deals, they're not being genuine with you because everybody sees kind
of both sides of that equation. And I think the first thing is it starts with good underwriting.
You know, it's often in this business when you're a long-term investor, it's hard to win on the
buy because you buy so well that you've immediately created value, but you sure can lose.
You know, Warren Buffett has one of my favorite sayings which says, when a management team
with a reputation for brilliance tackles a business with a reputation for bad
economics, it is the reputation of the business that remains intact. So very simply put, you know,
good managers, it's hard to overcome a bad industry, even if you have a good management team.
And that good industry, good business model starts with good underwriting. I will say the second
thing, though, is because you're a long-term investor, you've got to have a good team to go execute
and take advantage of the opportunities. In every deal that I've been involved with, even if they're
good deals, there are always periods of struggle. And so you've got to acknowledge that. And
put the team in place that can execute against those struggles. And I think competitive advantage
is ephemeral. So, you know, if you're not continually moving, continually improving, your
competitive advantage is often, you know, kind of quickly eroded. The other thing that I see is
when we underwrite something, there are a number of unknowns. But I take a lot of comfort when I see
situations where there are multiple levers for improvement. And I essentially look at that as if I'm
buying a decent business with embedded options. And what I mean by that is there's options to grow
through acquisition. There's options to grow geographically through opening new entities. There's options
through pricing or through supply chain management. And so when I'm underwriting that, I don't know for
sure which of those options will present themselves to me, but I take a lot of comfort in. There's numerous
ways to kind of drive value in this business and we'll figure out, you know, of the five we've
identified two, three or four that can really help get us home. And then listen, I think in every
good deal, there's some element of luck. Talk to us more about you brought up competitive advantage.
And this is another big buzzword that Buffett and Munger always talk about is an enduring
competitive advantage. I know from my own personal investing experience, this is something that I think
has matured where I didn't realize how important this was when I'm a lot of it. I know, I know,
whenever I first started investing, but now when I look back, I think that that's one of the
most important things that I can look at next to price and all the others.
But this competitive advantage piece is so important.
Can you explain why you also think that that's so important to the audience?
I'm working process and my experiences cause me to think about things differently.
But I have a lot more confidence in my ability to underwrite the quality of a business
model, then my ability to underwrite growth in a market. So, for example, you know, you think about
trying to project GDP growth or the growth of an end market like oil and gas or commercial
aerospace. I think that's really challenging. And in many ways, it's a little bit like a coin toss.
But if you ask me to underwrite what makes a good business model and you think about the attributes
of that, once you've identified that, I think those attributes are likely to be persistent.
So, for example, we look at things that have very low customer concentration. We look at businesses that have barriers to entry. We look at businesses that have relatively high variable costs because that allows you to navigate changes in the marketplace. We talk about value in terms of multiples of cash flow, but we talk about quality of businesses as a product of return on tangible capital. How much cash flow to the tangible assets of this business generate. And so I think that's a much more
durable way to underwrite and get comfortable with the investments that you're making.
And you're obviously looking at the trends of those and how they're progressing over time,
I'm assuming as well.
Absolutely.
Yep.
And, you know, it's kind of interesting.
All the analytics are quantitative and they focus on the metrics, but it's easy to forget
that those metrics are driven by people.
And so, you know, it really is a combination of financial capital and human capital that
create a successful situation.
You know, I'm curious when you think about a discount rate for the business that you'd be looking at.
One of the frustrations with a lot of people that are Warren Buffett-style investors that are doing these calculations for intrinsic value and things like that, they go to a business school and they're doing these CAP-M models and they're using the prices of other businesses and the volatility of other businesses to determine what they think the risk or the discount rate should be.
You know, my personal opinion is that that approach is so backwards.
I'm kind of curious how, because in private equity, I would think you're not doing no cap M model.
You're doing what you think your risk is, and then you're assigning that as your discount rate.
Let's talk about DCF and discount rates and cap M in general.
So it's tremendously theoretical.
And so it's interesting, but I think it's interesting not because of the answer it gives you,
but because of the process that forces you to explicitly make assumptions.
So when you're doing that analysis, you've got to make assumptions about growth rates,
and you've got to make assumptions around exit.
And so those are all valuable processes to kind of work through, but I think the answer
doesn't really drive how we think about what we're going to pay.
So first of all, the great thing in the private equity market is you pay a combination of
what you think it's worth, but also what you think you have to pay, right?
Because, again, it's a negotiated transaction.
So we think about the analysis we do as what can we afford to pay, what's the time?
top end. And then if we can, we obviously try to do better than that. But as we think about the actual
modeling, you know, we think about it in the context of a five-year-hold period. What can we pay
assuming a certain capital structure? We've been out in the market. We've talked to lenders.
We know how much leverage they would provide at roughly what rates. And then we do a forecast
over a five-year period. And we generally assume we're going to exit the same multiple that we bought
in at. And the combination.
of those things drives a certain return profile. And we would expect on, you know, deals that are
in our kind of wheelhouse that those pencil out somewhere in the 20 to 30 percent IRA over a five-year
period kind of time frame. So, you know, that is a planning process, not necessarily, you know,
the gospel, but that's how we think about the process. And do you have an internal rate of return
model for this? In other words, a threshold of how much return you're expected to get if you invest
in this opportunity? Absolutely. Yeah, no, for us, it's not so much in theoretical what is the cost
of capital. It's what's the IRA to the investor. So, Doug, now that we heard about some of the good
deals that you made, I don't want to put you on the spot, and I guess yet I'm doing it anyway,
could you tell us about some of the mistakes that you made in some of those deals and perhaps
even some of the things you completely neglected in whenever you did your due diligence of the company.
Yeah, so first of all, I think let me go back to one thing I said when we were talking about
good deals. All these deals have challenges, so you got to expect them. We kind of joke.
There's no such thing as a 20% T bill. We're pricing these assets with an expected high return
and implicitly that means I've got significant risk here. And so I think a lot of the game in my mind
is setting yourself up to avoid long-term impairment. And what I mean by that is, you know,
these things will go through cycles and there'll be tough times, but if you can avoid long-term impairment,
you generally can find a way to work your way home to a decent outcome, or at least an outcome
where you haven't lost significant capital. Where I find you run into real impairment risk that's
hard to navigate through, I think businesses with real customer concentration can lead to real
drivers of impairment. And then, you know, we talked about capital structure, and that drives a better
return because I'm using leverage. The reverse of that is if you're too aggressive with capital
structure and you hit a bump in the road, it's very difficult to kind of course correct.
And so, you know, we think about leverage as a double-edged sword. We want to use it to leverage
returns, but we try not to take the last dollar to give ourselves kind of a zone of error or
a margin of error in a way that we can navigate, you know, kind of Murphy's law, if you will.
And listen, we talked about teams on the positive side.
Teams, bad teams can be an opportunity or a liability.
If you find a situation where you have a bad team, if you're willing to make changes,
that actually can be an opportunity.
But I think you've got to go into the deal knowing that you think you're going to change
out the management team and be committed to doing that.
But I find generally, you know, on the deals we've struggled with,
we thought we had a management problem and we probably didn't act soon enough.
Let's take a quick break and hear from today's sponsors.
No, it's not your imagination.
Risk and regulation are ramping up,
and customers now expect proof of security just to do business.
That's why VANTA is a game changer.
VANTA automates your compliance process
and brings compliance, risk, and customer trust together on one AI-powered platform.
So whether you're prepping for a SOC 2
or running an enterprise GRC program,
VANTA keeps you secure and keeps your deals moving.
Instead of chasing spreadsheets and screenshots, Vanta gives you continuous automation across more than 35 security and privacy frameworks.
Companies like Ramp and Riter spend 82% less time on audits with Vanta.
That's not just faster compliance, it's more time for growth.
If I were running a startup or scaling a team today, this is exactly the type of platform I'd want in place.
Get started at Vanta.com slash billionaires.
That's Vanta.com.
slash billionaires.
Ever wanted to explore the world of online trading, but haven't dared try?
The futures market is more active now than ever before, and plus 500 futures is the perfect
place to start.
Plus 500 gives you access to a wide range of instruments, the S&P 500, NASDAQ, Bitcoin, gas, and
much more.
Explore equity indices, energy, metals, 4X, crypto, and beyond.
With a simple and intuitive platform, you can try.
trade from anywhere, right from your phone. Deposit with a minimum of $100 and experience the fast,
accessible futures trading you've been waiting for. See a trading opportunity, you'll
be able to trade it in just two clicks once your account is open. Not sure if you're ready,
not a problem. Plus 500 gives you an unlimited, risk-free demo account with charts and
analytic tools for you to practice on. With over 20 years of experience, Plus 500 is your gateway
to the markets. Visit plus 500.com to learn more. Trading in futures involves risk of loss and is not
suitable for everyone. Not all applicants will qualify. Plus 500, it's trading with a plus.
Billion dollar investors don't typically park their cash in high yield savings accounts. Instead,
they often use one of the premier passive income strategies for institutional investors, private credit.
Now, the same passive income strategy is available to investors of all sizes thanks to the Fundrise
income fund, which has more than $600 million invested in a 7.97% distribution rate.
With traditional savings yields falling, it's no wonder private credit has grown to be a
trillion dollar asset class in the last few years.
Visit fundrise.com slash WSB to invest in the Fundrise income fund in just minutes.
The fund's total return in 2025 was 8%, and the average annual total return since inception
is 7.8%. Past performance does not guarantee future results, current distribution rate as of 1231,
2025. Carefully consider the investment material before investing, including objectives, risks,
charges, and expenses. This and other information can be found in the income funds prospectus at
fundrise.com slash income. This is a paid advertisement.
All right. Back to the show.
Talk to the audience about the term impairment so they understand the terminology there.
Yeah, essentially think about the stock market. You know, the stock market goes up, the stock market goes down, and I still have value. The good news is the concern has not been impaired and over time I can still kind of grow my money back, if you will.
And impairment essentially means you've permanently diminished value in the asset.
So a good example is a bankruptcy, right?
At that point in the cycle, you were forced to turn over the keys to another owner, essentially.
And so there's no way you can kind of overcome that impairment.
Okay.
So, Doug, you have written a book.
And Stig and I have both gone through your book, Family Inc. is the name of the book.
And writing a book is really time.
consuming. I mean, it takes a lot of effort to put a book out there. And when you look at the
revenues that a book generates, it's often not worth the effort to write a book. And so the reason
I ask this is because you've dedicated so much of your time and energy to writing a book. And I'm
curious, what motivated you to do this? Like, why did you put this out there for people?
Yeah. Well, so first of all, let me let me make, just reaffirm something. You said, I'm,
I'm pretty sure that I'm violating minimum wage laws. If you look at it.
how much I've made on the book versus ours invested. So I can promise you there's not a money-making
adventure. And listen, I did it because I'm passionate about the topic and I think there's a big
opportunity to have an impact on people and really change the way people are thinking about
financial literacy. I argue it's one of the biggest challenges that we face in America today.
There are so many trends out there that are making it harder for people to navigate their life
in a way that's financially secure.
You know, it's job mobility, it's wage stagnation, it's increasing cost of education,
it's diminishing social safety nets, and it's increased life expectancy.
You throw all those things together, and the skills required to create a life where you're
financially secure are dramatically different than they were 20 years ago.
The problem is we're teaching this topic the same way we did 20 years ago.
And so my book is really an attempt to give people an actionable frame.
where they can make good decisions for themselves and help identify the big decisions that
really impact your financial security over a lifetime.
You really have these awesome tools on the website and we'll definitely link to them in
the show notes where it's very clear that you look at yourself and even your family as a business
and it's all lined up with financial statements that you can directly apply.
I don't know if it's because I know you and I know your background, but I couldn't help but think,
is this not just seeing yourself as running your own company, perhaps even a private equity company?
Is that the right interpretation of that?
That's absolutely correct.
And a little bit of history on how some of the key concepts of the book evolved for me.
My inspiration for the book is a product of my experiences as a young private equity investor.
And so I'm working on a number of portfolio companies looking at making investments.
And what I realized is many of the tools and analytics that we were using to assist the portfolio company could actually be applied to my personal finance situation.
So, you know, essentially, we're all in the business of selling our labor into the market.
So you're in the business of you.
I'm in the business of me.
You can make that leap.
Then the same kind of tools and logic apply that, you know, we teach folks in business school.
we should be thinking about that in our own personal financial decisions. Now, I'm not saying that means
you need to make every choice that is the financially optimal choice, but I think at least it forces
you to understand the financial implications of the choices you make.
You know, so for me personally, whenever I started my own business and I had to do my own
income statement and my own balance sheet and cash flow statement. And I was literally, you know,
doing the double entry accounting on my company, that's whenever I personally felt like my
understanding of how to assess the value of another business just kind of went exponential.
And it was very helpful for me to be doing those calculations and figuring it out because
when I looked at another company's books, I was like, oh, well, that's, that right there is not
good because in my own personal accounting when I would do that, that would be a really, that'd be
a red flag.
And so what I love about these tools that you've developed is that you've basically allowed any person off the street who doesn't own their own business to basically be doing these financial statements on their own on themselves.
And I think this is my personal opinion for people listening to this.
If you go in there and you play with some of these sheets that Doug's developed, you're really going to improve your understanding of how financial statements work.
It's going to help you when the next time you look at a public stock or, you know, maybe you get interested in private equity,
someday. All this stuff is going to really help you understand the value of a business and to understand
the plumbing of how the money moves through a business, how it moves through your personal finances.
I just, I love it. So I'm just, you know, if I could give it a plug for people, I highly recommend
that you check out these tools that Doug developed. Well, thanks, Preston. And for what it's worth,
I agree with you, you know, if I could encourage folks in school to take one course, I think it'd be an
accounting course, and not because you want to be an accountant, but it is the tool,
it's the communication, the language of business, and I think it just gives you so many,
such perspective as you apply it in other fields. And so I think, you know, causing, forcing yourself
to sit down and kind of think through what a person's balance sheet looks like and include
non-traditional assets like lifetime value of labor, lifetime value of social security,
and think through what the implications of those things are on your investment choices.
I think that's a really valuable exercise.
You know, I encourage people to do it periodically so you can see progress in the balance sheet
or essentially accumulation of net worth.
Having said that, just, you know, if that's not your thing, if you do it once and force
yourself to kind of look at it, I think that's still very eye-opening.
So going back to the background, I'm very curious to hear how you would equate that to
a busword like entrepreneurship, which is something that you always share these days.
So if you have entrepreneurship on one hand, then private equity and another, how are they similar?
And do you see them marry up in the end?
Yeah, I think it's, there are very similar activities on different ends of the spectrum.
But so first of all, I consider myself, and I'm a private equity investor, I consider myself a financial entrepreneur.
And essentially what that means is my skill set is not technology or software.
My skill set is capital.
and I'm trying to apply that in an entrepreneurial environment.
And so, you know, I would argue if you're an entrepreneur and you're trying to create a business,
you still are taking your intellectual property and your human capital and you're combining it
with financial capital to create a business.
And in that case, your primary tool is your intellectual property, your human capital.
I'm kind of coming at it from the other side of the equation saying I'm trying to find
businesses that have a capital need.
my primary tool is the capital, but I'm also using, you know, my intellectual capital and human capital.
And so I think it's almost a matter of mix, you know, so an entrepreneur is kind of nine parts,
human capital, one part capital, and a private equity investor's, you know, probably nine parts capital,
one part human capital.
But it's really, they're both very similar activities when you think about taking an idea,
a strategy, and operationalizing it through labor.
and a combination of capital.
All right.
So I'm really curious to hear your response to this one here.
Oh.
If you could go back to being 22 years old, you could meet your 22-year-old self.
That's how I need to phrase this.
If you could go back and meet your 22-year-old self, you just graduated from West Point.
You just threw your hat.
And you could give yourself just one, two pieces of advice about investing.
What would you have told yourself, knowing what you knew?
back then. What would you tell yourself? Oh, man. So advice about investing. So this is my advice to
young investors. I think you're asking, right? Yeah. Well, and so, and after you're done with the
investing advice, what would have been your life advice? So I want to get that next. Okay. All right.
So, you know, I think young investors make a couple common mistakes. The first is return over
dollars. And that concept is everybody focuses on IRR. People want to talk about my return on an investment
and a percentage terms. I think dollars gained is a much more relevant metric. And so I don't want a
20% return for six months. That's 10% big deal. I want to invest in businesses where I can
compound for long periods of time, which result in multiples of capital returned. So, you know,
20% for five years returning multiples of capital. That's the name of the game. And I didn't,
you know, early on, I think I thought about return and be damned what the duration was. And I think
duration is another concept that is hard for young people to deal with. But the name of the game here,
you know, Warren Buffett talks about all the time is patience and conviction. And so when you believe
you've got, you know, you're well-founded in your conclusions, you've got to have patience to let the market do.
thing for a young person, that's often very difficult.
All right.
And then if you need a moment to think about this one, feel free.
So what is the life advice?
I want to hear this one.
Yeah.
I honestly, it's a little bit of the same applied to your personal situation, not your
investing situation, but it has to do with duration.
And I think being able to think long term, being able to make choices that have
long term payouts is a real competitive advantage, strategic advantage.
And I wish when I was 20, I had thought more about what these decisions would, what the ramifications of these decisions would be when I was 50.
And I think when we're 20, we think about what it's going to be like when we're 20 and a half.
And so forcing people to think longer term.
You know, Bill Gates has a really interesting quote.
I don't know if you've ever heard this.
He said people way overestimate what they can do in one year and way underestimate what they can do in 10.
Yep.
Yep.
I think it's right.
And I think that's a real competitive advantage.
It's a real competitive advantage as an investor if you're able to look past the noise of a year and think about 10-year time horizons.
And it's a real competitive advantage as an entrepreneur, you know, just a life choice as well.
Thank you for your response, Doc.
And I can definitely say for me, I'd wish that I had applied both of those two pieces of advice when I was 22 when just starting out.
So my last question is a question that we're always very excited.
to ask of authors. What is your favorite book and why? You know, I don't know if I'd say
favorite, but the one that I'm most interested in right now and have really enjoyed, it's called
Lead Yourself First. It's inspiring leadership through solitude. And this is written by a guy
Mike Irwin, who happens to be a buddy of mine, but essentially Mike studies leaders throughout history
that have used solitude as an important tool for creative thought, using your moral compass,
emotional balance and confronting tough problems. And so he studies people like Eisenhower,
Martin Luther King. So I love the historical aspect of it, but I also love the tilingess of it.
You know, I think technology has a lot of unintended consequences. And in today's environment,
if you don't purposely carve out an environment where you're going to not be disturbed and you can
have good quality solitude, I think it's very hard to have any kind of deep creative thought
these days. And so it's a book that I enjoyed, but has been impactful in the way I'm trying to
spend my time today. Doug, we can't thank you enough. Brilliant answers here. And if people want to
learn more about you, they want to check out some of these tools, where can they find that?
So the name of the book is Family Inc. using business principles to maximize your family's wealth.
And I have a website. So that's family inc.com, f-am, I-L-Y-I-N-C.com. And as you
were so nice to describe. There's a bunch of tools there that help an individual create financial
statements as if they were a business. So that's a balance sheet and an income statement. And I think
just going through that exercise will force you to think a little bit differently about, you know,
things like your labor assets. So it was worth the time. Thank you so much, Doug. Really enjoyed the
interview. All right, guys. That was all the Preston and I had for this week's episode of the
investors podcast. We see each other again next week. Thanks for listening to TIP. To access the show
notes, courses or forums, go to theinvestorspodcast.com. To get your questions played on the show,
go to asktheinvestors.com and win a free subscription to any of our courses on TIP Academy.
This show is for entertainment purposes only. Before making investment decisions, consult a professional.
This show is copyrighted by the TIP network. Written permission must be granted.
before syndication or rebroadcasting.
