Search Captions & Ask AI

Inside Orlando Bravo’s Private Equity Playbook: How to Build a Top Firm

October 15, 2025 / 28:57

This episode features Orlando Bravo, founder of Toma Bravo, discussing private equity, his journey from Puerto Rico to billionaire status, and the role of private equity in the economy.

Bravo shares insights on Toma Bravo's growth, managing $179 billion in assets, and returning over $13 billion to investors last year. He emphasizes the importance of mentorship and the strategic decisions that led to the firm's success.

He reflects on his upbringing in Puerto Rico, the impact of Hurricane Maria, and how his family's support shaped his career. Bravo also addresses the perception of private equity as cutthroat, explaining how modern practices focus on growth and innovation.

The conversation touches on Toma Bravo's investment strategies, including the recent acquisition of Boeing's avionics business, and the challenges posed by AI in the tech sector.

Bravo concludes with his views on Puerto Rico's political status, advocating for statehood as a means to improve the island's future.

TL;DR

Orlando Bravo discusses private equity, his Puerto Rican roots, and Toma Bravo's growth strategies in this episode.

Video

00:00:02
With one of the best track records in
00:00:03
private equity,
00:00:04
Bravo manages 179 billion in assets,
00:00:08
Bravo has grown at a blistering pace.
00:00:11
Last year, the firm returned over $13
00:00:13
billion to investors. In 2019, Orlando
00:00:16
became the first Puerto Rico born
00:00:18
billionaire. Private equity firms, the
00:00:20
good ones, definitely beat the public
00:00:23
markets. We are in the business of
00:00:25
turning great innovators
00:00:28
into great businesses.
00:00:30
Ladies and gentlemen, please welcome
00:00:33
Toma Bravo's Orlando Bravo.
00:00:36
[Music]
00:00:38
[Applause]
00:00:39
[Music]
00:00:44
See you. Thanks for coming. How are you,
00:00:48
David? Good to see you. For those that
00:00:51
don't know, let me just do a a couple of
00:00:53
data points and then we'll just jump
00:00:54
into the story because Orlando has an in
00:00:56
Wait, are we are we seriously going to
00:00:58
ignore whatever virtue signaling JL is
00:01:00
doing over here? What
00:01:02
what's this uh virtue signal you got
00:01:03
going?
00:01:04
What are you doing right now?
00:01:04
Well, this isn't virtue. This is um my
00:01:07
bestie Tulsi gave me an official scarf
00:01:10
from her office
00:01:12
for my wife and I stole it from my wife.
00:01:14
So, I'm wearing it. And
00:01:16
I know you probably didn't see it
00:01:18
yesterday, but Jason was run over by the
00:01:21
director of national intelligence, Tulsy
00:01:22
Gabbard, yesterday. He was so tilted.
00:01:26
She was walking through the Russia hoax.
00:01:28
He was so tilted he had his phone
00:01:30
googling and grocking trying to get and
00:01:33
and all he could come up with is this.
00:01:35
And literally in this tone, what about
00:01:37
Paul Maniffort? And nobody knew what
00:01:39
that meant. Nobody knows who he is,
00:01:41
including her.
00:01:43
Okay, so your mother why you got to beat
00:01:46
up on Jason so much you should be a
00:01:49
nicer to him he is your bestie sorry
00:01:52
continue Orlando has an incredibly
00:01:54
inspiring story but let me just set the
00:01:56
backdrop of what uh Toma Bravo is to
00:01:59
Bravo started in 2008 so what is that 17
00:02:02
years now and now has just a little
00:02:05
under 200 billion which is incredible
00:02:07
but here are the two stats that stunned
00:02:08
me in June you raised $34.4 4 billion in
00:02:14
basically like a set of fund vehicles
00:02:16
which is I want to understand how that
00:02:18
is even possible and then you basically
00:02:20
have owned now or 500 companies and many
00:02:24
of the big software companies that you
00:02:26
know we probably interact with and have
00:02:27
to deal with. But before we get into all
00:02:29
those details, I think what's inspiring
00:02:31
is you are a child of Puerto Rico, a
00:02:37
small town in Puerto Rico, and I've
00:02:39
texted you this before, but I just
00:02:40
wanted you to tell everybody, how does a
00:02:43
guy, and I'm not I'm saying this in a
00:02:45
nice way, from literally the middle of
00:02:46
nowhere,
00:02:48
get here? How does that happen?
00:02:51
Your parents, your family, like how does
00:02:53
that happen?
00:02:54
Well, by the way, thanks so much for
00:02:55
having me. And I'm not sure how we're
00:02:57
supposed to talk about serious stuff and
00:03:00
private equity when when when we have
00:03:02
this, but
00:03:03
you persevere.
00:03:05
I I got this. Look, um that touches my
00:03:08
heart that you asked that question
00:03:10
because when Hurricane Maria hit Puerto
00:03:13
Rico,
00:03:14
kind of everything stopped for me
00:03:15
because my best friends are there, my
00:03:17
family's there, um cousins, my my whole
00:03:20
upbringing.
00:03:22
I got there on a plane the day after.
00:03:24
And where were you at the time? I was in
00:03:26
San Francisco.
00:03:27
Okay.
00:03:27
And we had gotten a message from Puerto
00:03:29
Rico saying there's some shelters,
00:03:32
particularly one that was really close
00:03:34
to my hometown of my that had only two
00:03:37
days supply of food and water. And there
00:03:39
were all these kids and everything else.
00:03:41
And the government of Puerto Rico, they
00:03:43
had they had trouble serving these
00:03:44
towns. So we said, "We'll go from San
00:03:46
Francisco and bring you a bunch of food
00:03:47
and water and we'll we'll be there
00:03:48
tomorrow." And they actually showed up.
00:03:51
When I landed, three of my friends that
00:03:53
I hadn't seen in a while, my best high
00:03:54
school friends, one of them asked me,
00:03:56
"Oh, now you're doing all this business
00:03:58
stuff. How did that happen?" And I said,
00:04:01
"Well, the odds are one of us had to get
00:04:03
lucky out of out of everybody here, one
00:04:07
I mean that there's there's some odds to
00:04:09
that."
00:04:10
But was that something like your parents
00:04:12
gave you where they're like, "You have
00:04:13
to go, you have to do something or
00:04:16
Yes. Now, at every turn, I tell you
00:04:18
this, how exactly I got here. I've never
00:04:22
created anything new, but I always had
00:04:26
my mom who was a Cuban immigrant. And
00:04:29
for her, just me staying there, it
00:04:31
didn't feel right to her. She was
00:04:33
always, you know, she would put me in
00:04:35
positions where I would always have to
00:04:36
be traveling to San Juan to play tennis,
00:04:38
the sport of tennis individual. Then if
00:04:40
I did well, I remember I played my first
00:04:42
tournament when I was 10 years old in
00:04:44
Karacas, Venezuela. And I saw wealth
00:04:46
back then, Karakas, Venezuela in 1982
00:04:50
was quite a place and you played in this
00:04:52
fancy club and then you if I do really
00:04:54
well, I get to play in Florida. So she
00:04:56
was always always kind of giving me a
00:04:58
road map for that. I was lucky that I
00:05:00
wasn't that good to go pro. So I went so
00:05:03
so that I went into business. But then
00:05:04
the same thing at at work, you know, I
00:05:06
had the two best mentors and the only
00:05:09
thing I give myself credit for is at a
00:05:11
young age I really listened. I had
00:05:12
discipline and I would kind of kind of
00:05:14
take it all in.
00:05:15
You were also the beneficiary of an
00:05:17
incredible mentor. And there's these
00:05:19
great stories. Yesterday we heard, you
00:05:20
know, Vlad tried to get a job at Climate
00:05:22
Corp. Couldn't started Robin Hood. You
00:05:25
know, famously, um, my HR lead at
00:05:29
Facebook introduced me to her then
00:05:31
boyfriend Ben Sberman. We interviewed
00:05:33
Ben. We ended up not hiring him. He
00:05:35
immediately started Pinterest. And when
00:05:38
you graduated from Stanford, you only
00:05:40
got one job offer from like a
00:05:42
threeperson firm basically. Do you want
00:05:43
to tell us about that story?
00:05:45
Yeah, I would you know at 1997
00:05:49
there was not not much private equity
00:05:52
and the venture business you didn't hire
00:05:54
a lot of people. It was also it was also
00:05:56
small. Now I I want to add this to the
00:05:59
story. I had I got one interview with
00:06:02
one of the largest private equity firms
00:06:03
at the time and the head of the firm
00:06:06
spent time with me. Very very nice guy.
00:06:09
But you know what he said and this is
00:06:10
1997.
00:06:12
There's not much opportunity in our
00:06:13
industry anymore and the industry is
00:06:16
taken.
00:06:18
Now our firm is multiples bigger
00:06:20
than they are. And the same thing will
00:06:22
happen in the future for the few of you
00:06:23
that may be interested in private
00:06:24
equity. you'll come by and create a firm
00:06:27
and it the American spirit and
00:06:29
entrepreneurialism and being at the
00:06:31
right place at the right time because we
00:06:32
started doing software and it's hard not
00:06:34
to do well if you started doing software
00:06:36
back then and had all this uh this wind
00:06:38
behind your back. So, I didn't I
00:06:41
couldn't get a job. There weren't many.
00:06:42
And then Carl Toma hired me. And at the
00:06:45
end of the process, this is interesting.
00:06:47
There were a few private equity firms
00:06:48
that kind of opened up a position for me
00:06:50
to do Latin American private equity. And
00:06:53
I'm like, "No, I've I've spent too much
00:06:55
time in the south. The money's in the
00:06:57
north. I I you know, I want to do US
00:07:01
buyout tech. That's what I wanted to
00:07:03
do." And Carl was great. He said, "If
00:07:05
you want to do tech, that's not
00:07:06
something we do, but you know, start
00:07:08
looking at it and and we'll we'll help
00:07:10
you."
00:07:11
And so, so just tell us about how the
00:07:14
decisions you've made now to build this
00:07:15
business. How many people do you have?
00:07:16
How do you run 200 billion effectively?
00:07:19
How do you raise 34 how do you what do
00:07:20
you tell people to raise 34 billion? I
00:07:23
don't I don't even I don't even
00:07:24
comprehend that.
00:07:25
I think you do. Come on.
00:07:27
You guys have done pretty well. I
00:07:28
appreciate that. But but it's uh okay.
00:07:31
So we have we are very very focused on
00:07:35
keeping the team very small. So we have
00:07:39
about 230 people at at Toma Bravo within
00:07:43
the organization.
00:07:45
Um the the reason is you if if you have
00:07:47
too big of a team, you become internally
00:07:49
focused and start dreaming about
00:07:51
conversations internally. And as I
00:07:54
always say, the deal's not in the
00:07:56
office, the company's not in the office,
00:07:58
and the buyer of your company's not in
00:07:59
the office. So, you always have to be
00:08:01
outward facing. The second thing is I
00:08:04
got the benefit, and so did my senior
00:08:06
partners of incredible mentorship. I can
00:08:08
tell you so many stories about Carl Toma
00:08:09
spending time with me in 1998 on the
00:08:12
deal we were going to lose. And I would
00:08:14
be like, why did you spend all that time
00:08:15
with the CEO and me on his kitchen
00:08:17
table? He wanted to teach me how to
00:08:19
sell. He wanted to teach me how to do a
00:08:20
deal. and and that was just incredible.
00:08:23
So if we have too many of those, we
00:08:24
can't we can't touch the next generation
00:08:26
leadership. So that is that is part of
00:08:29
our philosophy. Now how do we raise that
00:08:31
money? Look, our first deal, it's always
00:08:34
been one step at a time. Our first deal
00:08:36
was 50 million. The second deal was 100
00:08:37
million enterprise value. The third was
00:08:39
data at 250 million. We didn't buy a
00:08:42
company in Silicon Valley till 2010. Uh
00:08:45
that was Sonic Wall that we paid 550
00:08:47
million in take private. That was our
00:08:49
first foray into real cyber um in in
00:08:52
higher growth uh businesses. So one
00:08:55
little step at a time. There was a time
00:08:57
that we couldn't raise a billion dollars
00:08:58
but now we have enough of a following
00:09:00
that you know people people
00:09:02
what is the role of private equity in
00:09:04
the US economy do you think what is the
00:09:07
role that it should play? I think it's a
00:09:09
great change agent.
00:09:11
It's it's a business in a way similar to
00:09:13
venture where what matters is the
00:09:17
returns that you put up and you have
00:09:20
incredible alignment with the sources of
00:09:22
capital. They give you the money and if
00:09:25
you make the return, you can stay in
00:09:27
business. And if they give you the money
00:09:29
and you don't make the return, no matter
00:09:30
how big we may be, we slowly lose that
00:09:33
and and we're out of business. And and
00:09:35
that that alignment is so important
00:09:37
because you're such a big change agent
00:09:39
to companies. These software companies
00:09:41
are not meant to be owned by the same
00:09:43
group for 30 or 40 years. Management
00:09:46
gets tired. It's exhausting to run. It's
00:09:48
exhausting to be a CRO. And the more
00:09:50
they trade hands. You have somebody with
00:09:52
maybe a new idea, maybe a perspective,
00:09:54
and maybe a perspective that was right
00:09:56
for the company at that time. And that
00:09:59
buyer like private equity can assume be
00:10:01
super entrepreneurial and try to do
00:10:02
something special. So Orlando though the
00:10:04
the just building on that it clearly has
00:10:07
alignment with the investors but maybe
00:10:09
you could talk a little bit about the
00:10:11
broader alignment with society jobs the
00:10:13
reputation of PE sometimes is a bit too
00:10:16
cutthroat and if you hear oh a PE a firm
00:10:18
bought my favorite brand or our firm got
00:10:21
bought by you know our startup got
00:10:23
bought by a P firm it's like okay
00:10:25
they're going to cut half the people and
00:10:26
there's going to be layoffs or maybe
00:10:28
this brand is going to get saddled with
00:10:29
debt and absolutely gutted for parts. So
00:10:33
what's fair or unfair about that sort of
00:10:36
PR crisis? Maybe there is with PR with
00:10:38
with PE.
00:10:39
That is 100% fair in the 80s, 90s, and
00:10:43
maybe early 2000s.
00:10:46
Private equity has nothing to do with
00:10:48
that. Now about 50% of the private
00:10:50
equity deal volume is in technology. We
00:10:54
we do that. We're we we're very narrow.
00:10:56
We only do software. If you look at any
00:10:59
software deal we've done in the last 12
00:11:01
13 years after SAS became irreversible
00:11:04
in '05
00:11:05
you're paying 7 to8 times revenue and
00:11:08
the financing on 7 to8 times revenue is
00:11:10
maybe two turns of revenue so you're
00:11:12
putting in five to six turns of equity
00:11:13
in the company 30% debt 70% equity if
00:11:17
you're not building and growing that
00:11:18
business especially if it's big nobody's
00:11:21
going to buy it from you it used to be
00:11:23
that for those old school deals if you
00:11:25
look at the return twothirds of the
00:11:27
return will come today from the cash
00:11:29
flow of the business from your yield and
00:11:31
a little bit in the terminal value. It's
00:11:33
flipped about 2/3 or more is terminal
00:11:36
value appreciation and you make very
00:11:38
little. So you're a growth investor on
00:11:39
your yield. We really are we had to
00:11:41
transfer to that because look the the
00:11:43
lucky thing we had was after I
00:11:45
personally made a lot of mistakes 97 to
00:11:47
the internet bubble bursting. Carl Toma
00:11:50
was going to fire me and this is also
00:11:52
true. He he talked about it in his 70th
00:11:54
birthday and and he gave me another
00:11:56
chance and I said, "Okay, I'm not good
00:11:59
at what we were doing then. I'm gonna go
00:12:02
for existing management,
00:12:05
really established companies and
00:12:08
software." In 2000, you could buy
00:12:10
recurring revenue and software cheaper
00:12:11
than in all the other categories that
00:12:13
private equity liked. Think about radio,
00:12:17
uh, cable, whatever. Rec outdoor
00:12:19
advertising, anything. So, the
00:12:20
partnership said, "Sure, let's try it.
00:12:22
Let's try with something small. At that
00:12:24
time, you could buy cheap. But what
00:12:26
happened is in 2010
00:12:29
after the financial crisis, most of our
00:12:32
competitors that were doing those deals
00:12:33
and it was heavily competitive then for
00:12:35
these smaller transactions, they left
00:12:37
the business because now software became
00:12:39
super expensive.
00:12:40
So there's a but we said chamat but then
00:12:42
we said oh instead of complaining that
00:12:45
we cannot do what we were doing before
00:12:46
because everything changes. Now we have
00:12:48
the wherewithal to buy the best and the
00:12:50
number one. So let's go for the number
00:12:52
one player that can grow.
00:12:53
So you started doing a lot of these SAS
00:12:55
deals in 2010. When you sit there with
00:12:58
your partners in 2025,
00:13:01
is there a risk of SAS
00:13:04
being cannibalized from within by AI or
00:13:07
you know how it can just be rebuilt in
00:13:09
different ways? How do you underwrite it
00:13:11
today which is different from how you
00:13:13
may would have underwritten it in 2010?
00:13:15
Our investors don't love to hear this
00:13:18
because for right our investors
00:13:21
especially the large institutions that's
00:13:23
kind of our market that those are our
00:13:25
our our people that have backed us for a
00:13:27
long time besides good returns they need
00:13:29
consistency
00:13:31
and predictability they would rather
00:13:33
have us do what we were doing in 2002 in
00:13:37
these deals and why why can't you just
00:13:39
keep doing the same thing and it all
00:13:40
changes one is there is a big risk of AI
00:13:46
in this business I mean in a big big way
00:13:49
there's so many verticals that are going
00:13:50
to get disrupted there's so many areas
00:13:52
that are very confusing and you don't
00:13:54
want to touch so it limits the space
00:13:57
significantly even if you believe what
00:13:59
we believe which is in the enterprise
00:14:01
it's going to take a while because we
00:14:03
always say technology is evolutionary
00:14:05
not revolutionary because our customers
00:14:07
are buying this stuff for cost they want
00:14:10
the ROI and you need to see the plan and
00:14:12
everything else but one is there's a big
00:14:14
disruption and that's and other all
00:14:15
these areas we don't get into. Um, and
00:14:18
we have to keep learning um and and
00:14:20
updating ourselves. That's that's a lot
00:14:22
of of work that the young people in the
00:14:24
firm as well will have to do. But we
00:14:26
have another equally big or even bigger
00:14:29
challenge which is if you look at our
00:14:31
trajectory, it's not like one day we
00:14:33
woke up and said, "Oh, we can do a $10
00:14:35
billion deal." No, we we started 50 that
00:14:39
trajectory in 2010. We did three billion
00:14:42
dollar deals in a row. Um we bought blue
00:14:44
code we took it private. DelTech we took
00:14:46
private we bought digital insight from
00:14:48
into it. When those worked then we did a
00:14:50
$2 and half billion dollar deal that
00:14:52
became Dinatrace that was compare. Then
00:14:54
when that worked we did a $5 half
00:14:55
billion dollar deal which Dina was here
00:14:58
yesterday. That was the business that we
00:15:00
sold to NASDAQ and that worked. But now
00:15:02
we're doing $10 billion deals. We have
00:15:05
to sell those for 25 to make money.
00:15:07
Wow. our our alternative here, what we
00:15:10
have to underwrite is an IPO at a big
00:15:13
discount to the comps when we paid a 30%
00:15:16
premium to the comps to buy that company
00:15:18
in the first place. So, we kind of start
00:15:20
50% in the hole. Well,
00:15:22
to do that. So, you have to Anyway,
00:15:24
I wanted to ask you this question
00:15:25
because I I asked a friend of mine about
00:15:26
you and he was competing with you to get
00:15:29
the Boeing business and you you bought
00:15:31
the Boeing avionics business recently
00:15:33
for 10.5 billion, which I think all of
00:15:35
us care about because hopefully it'll
00:15:37
improve flight safety and all of that
00:15:38
other stuff, but we can talk about that
00:15:39
in one second. But he said Orlando's
00:15:42
incredibly difficult to compete with
00:15:43
because they're so he's so ready to buy
00:15:46
the thing he wants to buy and he doesn't
00:15:49
really, you know, nickel and dime at the
00:15:52
edges. It's like, let's find a fair
00:15:53
price and we'll just transact and it
00:15:55
makes it very hard for everybody else to
00:15:56
compete with. When you get that
00:15:57
conviction, are you just willing to just
00:16:00
basically put that much money on the
00:16:01
line and say, "We're going to figure
00:16:02
this out."
00:16:03
We are.
00:16:04
That's sort of Warren Buffett's
00:16:05
mentality, isn't it? That he he already
00:16:07
knows all the companies. is he knows
00:16:08
which ones he wants to buy and when they
00:16:10
come up that he doesn't nickel and dime
00:16:13
he just quickly works out a deal. Is
00:16:14
that something is that a mentality that
00:16:16
you have?
00:16:17
100%. It all it all fits together with
00:16:19
having a small team. We also have a
00:16:21
small portfolio. So in every fund we'll
00:16:24
buy 10 to 12 companies.
00:16:26
We we strive for the two core
00:16:29
competencies that we try to have. One is
00:16:32
buy the best and operate the best and
00:16:35
just focus on that in a 3 to four year
00:16:38
time frame for our funds for investing
00:16:40
our funds. We cannot say with a straight
00:16:42
face that there are 30 of the greatest
00:16:45
companies that were available to be
00:16:46
bought at that time.
00:16:48
Right?
00:16:48
So, so that's why and two we cannot say
00:16:51
with a straight face that we can try to
00:16:53
influence management with everything we
00:16:55
learned from an incredible mentor if we
00:16:57
had a portfolio of 30. That's as much as
00:16:59
as we can handle. So, we have to go for
00:17:01
it. Now, I do want to add that what I
00:17:04
love about the private equity business,
00:17:06
one of the items is that those deals
00:17:09
because the decisions that you make with
00:17:11
your partners an hour before the bid is
00:17:15
is really really important. It's really
00:17:17
telling.
00:17:18
Well, can you take us behind the TikTok
00:17:19
of this Boeing asset? It's I think it's
00:17:21
like a it touches all of us even if most
00:17:23
of us don't understand that it even
00:17:24
existed actually. Well, it it basically
00:17:27
runs maybe you cannot fly an airplane,
00:17:30
right, without Jeepposin and and its
00:17:32
system. And the way the deal started,
00:17:35
uh, we called the the CEO of Boeing,
00:17:38
actually sent him an email saying, "Hey,
00:17:40
we could buy this division and we're
00:17:42
paying these these good prices." So,
00:17:45
there was some interest. The process
00:17:46
started and there were about 15 private
00:17:48
equity groups, all excellent groups
00:17:49
involved in the deal.
00:17:51
But, why would Boeing want to sell its
00:17:53
avionics business? I guess maybe start
00:17:55
with that like
00:17:56
Yeah, it seems pretty core. It's a good
00:17:58
business and I I I'm happy that they
00:18:00
decided that.
00:18:01
So, you're saying that was a bad
00:18:04
decision to sell a cockpit?
00:18:08
We'll take it.
00:18:09
Fair enough. Um I I wanted to ask you a
00:18:12
question about
00:18:13
Can we get the answer to that though?
00:18:14
What what what is the strategic rational
00:18:16
for Boeing to want to sell its avionics
00:18:18
business? Is the idea that other plane
00:18:20
manufacturers can then use that avionic
00:18:22
system? I'll give my answer and maybe
00:18:24
you can.
00:18:25
I think Boeing is in this incredibly
00:18:26
difficult position where there's a lot
00:18:29
of diffuse things that were happening
00:18:30
inside of the business
00:18:32
and they had to make a real
00:18:35
rationalization. What are the few things
00:18:36
we can be good at? So, you know, one of
00:18:38
our friends, Brian Utko, was put in
00:18:40
charge of new plane development. I think
00:18:43
you know, you can guess what's going to
00:18:44
happen there. That's a clear strategic
00:18:46
bet. You know, getting the 737 or this
00:18:49
the max program back online. That was a
00:18:51
clear bet. But when you do that, you
00:18:54
have all kinds of debt and stuff that
00:18:56
you just need to clean out. And
00:18:58
sometimes you have to sell. And by the
00:19:00
way, you are right. Your instincts are
00:19:02
right because my friends who called me
00:19:04
basically said this is the gem asset
00:19:07
inside of Boeing. I mean, he's being
00:19:08
very gracious by not you. So yeah, but
00:19:11
Jeepson is the thing that everybody
00:19:13
uses. United, Delta, everybody needs
00:19:15
this information to fly accurately. And
00:19:17
it was Boeing's business and now it's
00:19:18
Orlando's business.
00:19:19
Okay. So
00:19:20
what's our phone's business? I wish it
00:19:21
was like
00:19:23
it's your Orlando. We um we don't buy
00:19:26
stuff. We're generally year zero, year
00:19:28
one, two investors who help build
00:19:30
things, but Sax and I got to watch our
00:19:32
friend Elon buy Twitter and um that was
00:19:35
quite eye opening. It was also the first
00:19:37
thing that I think he ever bought in in
00:19:39
you know a major way like that. What is
00:19:42
the playbook for coming into one of
00:19:44
these technology companies and you have
00:19:48
like you said tired management maybe the
00:19:50
people who are still saying at this
00:19:52
company are the ones who couldn't find
00:19:53
other work or maybe weren't as
00:19:55
ambitious. What's it like day zero, day
00:19:58
one, day two when you get in there?
00:20:00
What's the playbook? What's you know
00:20:01
one, two, three, we got to do these
00:20:03
things in the first 30 days.
00:20:05
It's almost always the same. We we try
00:20:08
to buy companies and Jefferson is a a
00:20:11
tweener in that because their margins
00:20:13
were about 25%. But we feel that
00:20:15
business can be running like a Denza
00:20:17
that we sold to NASDAQ for 50% plus
00:20:19
running it like a software company and
00:20:21
making the right investments.
00:20:23
The the playbook is this. You meet with
00:20:25
a company uh usually a public company
00:20:28
that trades for a revenue multiple
00:20:30
because they're not that profitable.
00:20:33
And our our mentality is we try to turn
00:20:35
what we call a good innovator into a
00:20:37
good business. We have all these
00:20:39
meetings with management and after we
00:20:40
listen a lot to them, we come back to
00:20:42
them and we have we put together a plan
00:20:45
with them to cut cost. So there is that
00:20:47
element because you have to get in the
00:20:49
game with a certain level of fundamental
00:20:51
earnings to be able to afford the deal.
00:20:53
You you you basically are what we're
00:20:55
trying to do is turn a revenue multiple
00:20:57
day one, say we buy it for six or seven
00:20:59
times to an ebida multiple in day four.
00:21:02
If that company grew 20% and you achieve
00:21:04
a 50% margin, you've done that. And then
00:21:07
you say, "What are the comps? What is
00:21:08
this thing worth? Is it a 20p a 25p?" A
00:21:12
20p is about 15 times ebida. You could
00:21:13
double your asset value without the
00:21:16
benefit of that 30% leverage which you
00:21:18
pay down a bit and that's how you create
00:21:19
your return. So you you talk we talk to
00:21:22
management very openly during the
00:21:24
process even before we won the deal even
00:21:27
if they're not going to like us etc. and
00:21:29
we say, "Hey, can we put together a plan
00:21:32
where you can make the right investment
00:21:33
decisions, but can you cut 15% of the
00:21:36
cost of the company at closing?" The
00:21:39
deal in private equity, talk about the
00:21:41
change agent. If you don't do that at
00:21:42
closing in private equity, why are you
00:21:45
going to shock the employees afterwards?
00:21:47
Your 2, three, four, the deal, since
00:21:49
everybody's thinking there's a new owner
00:21:51
that's going to provide change, gives
00:21:53
you the opportunity for immediate
00:21:54
change. Now, as my mentor Marcel Bernard
00:21:57
used to say, he was the greatest
00:21:58
operator I've ever met. 35 years at
00:22:00
Motorola running different divisions and
00:22:02
that was an exceptional school of
00:22:04
management. No matter how profitable you
00:22:06
are, you can always cut 10%. No matter
00:22:08
how unprofitable you are, it's difficult
00:22:11
to cut more than 20%. Because you have
00:22:13
to change the way people make decisions,
00:22:14
the way management interacts, etc.
00:22:17
How do you evaluate the talent stack?
00:22:19
That was something that actually David
00:22:21
was exceptional at during the Twitter
00:22:23
acquisition. And we sat there in a room
00:22:25
and he said, "Well, who's exceptional at
00:22:28
their job?" And then Elon said, "And
00:22:31
who's absolutely critical for this
00:22:33
business?" And I just walked up to the
00:22:34
whiteboard and I drew four quadrants,
00:22:36
exceptional, essential. And then there
00:22:39
was this sort of exceptional but not
00:22:42
essential. And we we we then had a
00:22:44
clear Elon proved that you could cut 85%
00:22:47
of Twitter and it would still work just
00:22:49
fine.
00:22:49
And all the journalists were like,
00:22:51
"Twitter's going to go down any day
00:22:52
now." And then they were like every day
00:22:55
they would write the same story. Twitter
00:22:57
went down and be like, "Oh no, you lost
00:22:58
your internet connection on your phone
00:23:01
and they'd be like,"No, it's it's not
00:23:03
coming up." And it's like, "Yeah, yeah,
00:23:05
reut the P Wi-Fi password in." And it
00:23:07
never went down. It it was pretty crazy.
00:23:10
But how do you assess talent when you're
00:23:12
coming into one of these legacy
00:23:15
businesses, you know, 10 years, 20 years
00:23:17
into the business?
00:23:18
History tells you a lot of that. So you
00:23:20
you're trying to identify
00:23:23
not everybody's good at everything and
00:23:25
it starts with a leader. If the leader
00:23:27
is good, everything is good. If the
00:23:29
leader is not good, nothing is good. You
00:23:31
you don't want to work around them to
00:23:33
deal with sales and product and stuff
00:23:34
because the nothing is going on. Now
00:23:37
what does a good leader mean, right?
00:23:39
There's so many judgments that come in.
00:23:41
Are they is a company hitting bookings?
00:23:42
Is it missing? Are they good at customer
00:23:44
service? What's their retention? How do
00:23:45
they make decisions? What we look for
00:23:48
overall because nobody's perfect is to
00:23:50
back what they're look what they're good
00:23:52
at. We love to do add-on acquisitions
00:23:54
for our company. So the reason we like
00:23:56
to take out the cost once is the rest is
00:23:58
about bookings growth and add-ons. We
00:23:59
don't want to revisit margin too much.
00:24:01
We want profitable growth going forward.
00:24:03
Let's be done with that and then let's
00:24:04
go forward. The leader can stand up in
00:24:06
front of the entire employee base and
00:24:08
said we needed to do this. This deal
00:24:10
probably gave us the courage to do what
00:24:11
we need to do. Let's go. Let's go build
00:24:13
the business. So, but we we look at a
00:24:15
leader and we say if they're
00:24:17
open-minded,
00:24:18
if they care about numbers and if they
00:24:21
have the following of their employees
00:24:22
and customers and really know the
00:24:24
business, that is something that we
00:24:26
really, really, really try to work with.
00:24:28
With all the changes we make, we've been
00:24:29
pretty contrarian in the industry
00:24:31
because we first try to make them with
00:24:32
the existing people. And sometimes, you
00:24:34
know, we make a mistake on that and they
00:24:36
change their mind, but we we try to do
00:24:37
that.
00:24:38
Before you do a deal, what's the secret
00:24:40
to figuring out how good the asset is?
00:24:43
Do you go talk to customers, backdoor
00:24:45
references? Do you go find the employees
00:24:47
who quit and started companies and
00:24:49
interview them? Like, there's got to be
00:24:50
some tricks to assess a company before
00:24:53
you even let them know you're interested
00:24:54
in them. What are those tricks?
00:24:56
All of that. All of that. Now, we've
00:24:59
usually owned a competitor or a partner
00:25:02
to the company as well
00:25:04
and and we've usually known him for a
00:25:06
long time. Like we recently announced
00:25:08
that we were doing the Day Force deal
00:25:09
for 12 billion. My partner Holden Spade
00:25:13
met with the CEO of Day Force in 2008
00:25:15
and we've tracked that company for so
00:25:17
long watching it when does it miss when
00:25:20
does it hit its numbers and everything
00:25:22
else. It's um
00:25:25
you get you also once you sign them up
00:25:28
uh or are in a process where the
00:25:30
company's giving you all their raw data,
00:25:32
you have so much information to make
00:25:34
those choices. Like for example, a
00:25:36
company cannot say that it has really
00:25:39
really good product if its gross margins
00:25:42
on support are very low.
00:25:45
And we can bring technology people to
00:25:46
assess that and we have that on our team
00:25:48
and they look at the architecture and
00:25:49
the the talent and everything else. But
00:25:51
then you go how come your support calls
00:25:53
are so high?
00:25:54
It's a bad product. It
00:25:55
yeah it it it all fits together. If you
00:25:57
have great retention,
00:25:59
great margins on support. It's like for
00:26:01
example take support. Many people look
00:26:03
to offshore support and now maybe AI
00:26:07
would would get on on that and there's
00:26:08
no need for that. What we say is
00:26:11
eliminate the reason for the call alto
00:26:12
together
00:26:13
because there's nothing you can do in
00:26:14
product. So we're evaluating all that.
00:26:16
We love it. We geek out over it.
00:26:18
There's a handful of PE firms obviously
00:26:19
that are now lynch pins of the capital
00:26:21
markets. Blackstone, Apollo, KKR,
00:26:25
Carlile, they're public, they are
00:26:28
multistrat. They're huge pillars. And I
00:26:31
mean, you've built an incredible
00:26:32
business. You have the credibility to do
00:26:34
it. Is there an impetus to do it? Is
00:26:37
there an impetus to kind of grow beyond
00:26:38
that technology focus? And if not, how
00:26:41
do you stay in your knitting? Because
00:26:44
it, you know, how do you do that? How
00:26:46
where does the discipline come from?
00:26:47
Look, I I think um
00:26:51
we are very pure to our investor base
00:26:54
and our colleagues, the two of them at
00:26:56
the same time. What I say matters to
00:26:58
them is the return.
00:27:01
So what matters for us to grow the
00:27:03
business is get the money, get the deal,
00:27:05
improve the deal. Going public does not
00:27:08
help any of those things for us. That
00:27:11
that's that's number one. Two is we're
00:27:14
really I'm just so grateful. I I really
00:27:17
really am for my mentors. I mean, Carl
00:27:20
Toma gave me and my partners the
00:27:21
company,
00:27:22
right?
00:27:22
And he mentored us. So, we want to do
00:27:24
the same thing for the next generation.
00:27:26
And we actually feel we'll make more
00:27:28
money by investing behind the next
00:27:29
generation when that time comes than by
00:27:31
going public and having a great day and
00:27:34
a great multiple and and then what? So,
00:27:36
so far we're just going to we're just
00:27:38
going to stay where we are.
00:27:39
As we wrap, I I just want to ask you a
00:27:41
question about Puerto Rico again, where
00:27:43
we started. You're the first Puerto
00:27:45
Rican billionaire. I understand it's um
00:27:48
it's just a number obviously, but should
00:27:50
Puerto Rico become the 51st state? You
00:27:53
know, we we have Trump talking about
00:27:54
Greenland, whatever. Um you know, we
00:27:57
have these ambitions. The people of
00:27:58
Puerto Rico seem to want to have a
00:28:01
deeper relationship with America. It
00:28:03
seems profoundly unfair that they're in
00:28:04
this, you know, sort of middle state.
00:28:07
Yeah. It's such a divided place. The
00:28:10
turnouts in elections in Puerto Rico
00:28:13
when I was a kid used to be like 90%.
00:28:15
It's a whole festival in the island when
00:28:18
elections happen between the party that
00:28:19
wants the status quo and the party that
00:28:21
wants statehood. Now, the party that
00:28:23
wants statehood has grown quite a bit
00:28:25
and some of the tax incentives of being
00:28:27
um kind of in this Commonwealth status
00:28:29
have gone away. I'm going to say
00:28:31
something I've never said before and I I
00:28:34
do believe it'll be better for Puerto
00:28:35
Rico to be a state if the US would allow
00:28:37
that.
00:28:37
I'm for it. I'm here for it. Ladies and
00:28:40
gentlemen, Orlando Bravo.
00:28:43
Thanks, man.
00:28:44
Wow. Thank you. Incredible, huh? I'll
00:28:46
talk to you soon.
00:28:48
Great job. Thank you. Amazing.

Badges

This episode stands out for the following:

  • 70
    Most inspiring
  • 60
    Most heartwarming
  • 60
    Best overall
  • 60
    Best concept / idea

Episode Highlights

  • Orlando Bravo's Inspiring Journey
    From Puerto Rico to billionaire, Orlando Bravo shares his incredible story of perseverance.
    “You persevere.”
    @ 03m 05s
    October 15, 2025
  • The Power of Private Equity
    Orlando Bravo discusses how private equity can be a change agent in the economy.
    “Private equity has nothing to do with that.”
    @ 10m 46s
    October 15, 2025
  • Boeing's Avionics Business Acquisition
    Orlando Bravo explains the strategic rationale behind acquiring Boeing's avionics division.
    “We could buy this division and we're paying these good prices.”
    @ 17m 40s
    October 15, 2025
  • Puerto Rico's Statehood Debate
    Orlando Bravo shares his thoughts on Puerto Rico potentially becoming the 51st state.
    “I'm for it. I'm here for it.”
    @ 28m 37s
    October 15, 2025

Episode Quotes

Key Moments

  • Inspiring Story03:05
  • Private Equity Insights10:46
  • Boeing Acquisition17:40
  • Elon Buys Twitter19:32
  • Talent Assessment22:14
  • Statehood Discussion28:37

Words per Minute Over Time

Vibes Breakdown

Related Episodes

Podcast thumbnail
Trump vs Powell, Solving the Debt Crisis, The $10T AGI Prize, GENIUS Act Becomes Law
Podcast thumbnail
Fed Hesitates on Tariffs, The New Mag 7, Death of VC, Google's Value in a Post-Search World
Podcast thumbnail
"Founder Mode," DOJ alleges Russian podcast op, Kamala flips proposals, Tech loses Section 230?
Podcast thumbnail
Tucker Carlson: ICE Raids, LA Riots, Strong Economic Data, Politicized Fed, War with Iran?
Podcast thumbnail
E62: Elizabeth Holmes verdict, fraud origins & takeaways, navigating "The Great Markdown" & more
Podcast thumbnail
E65: VC markup dynamics, Russia/US tensions over Ukraine, Altos Labs raises $3B, Stripe mafia & more
Podcast thumbnail
Home Affordability Crisis, Palantir's Advantage, Big Short on AI, H-1B Abuse, Solar Storm Hits Earth