Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974

1. 0:00 – 1:53

   Thoma Bravo’s Founding Story

   1. HSHarry Stebbings0:00

      ... early stage VC is very often where, you know, price, it doesn't really matter. At your stage, I think it's a very different game. How do you reflect on your own price sensitivity?

   2. OBOrlando Bravo0:09

      Oh, price matters. (laughs)

   3. HSHarry Stebbings0:12

      Orlando, I am so excited for this. So first, thank you so much for joining me. I've been really looking forward to it.

   4. OBOrlando Bravo0:17

      Harry, I'm fired up. Thank you for having me.

   5. HSHarry Stebbings0:21

      Uh, listen, the joy is all mine. But I want to start with a little bit on you. So we see Thoma Bravo today in all of its glory, but take me back, how did you come to found Thoma and what was that aha moment for you with the opportunity in front of you?

   6. OBOrlando Bravo0:33

      It was awesome. (laughs) I, I tell you how it was. Um, I started at our predecessor firm in 1997. And now I'm, I'm really dating myself, I really don't think of myself as that old.

   7. HSHarry Stebbings0:44

      (laughs)

   8. OBOrlando Bravo0:45

      And, and, and my, my mentor, Carl Thoma, gave me a lot of authority and responsibility, and I always wanted to do tech for some reason. I was in the San Francisco office. And, and I made a lot of mistakes and he didn't fire me.

   9. HSHarry Stebbings1:00

      (laughs)

   10. OBOrlando Bravo1:00

       And, and, and something happened, which is when the dot-com bubble burst, '99, 2000, we saw that we could buy software really cheap. The more we studied these companies, the more we realized their recurring revenues are really strong, but none of them were making money. So we developed an approach that said, no, with 90, 80% gross margins, like today, these companies can be buyout candidates and can be really profitable. So Carl Thoma gave us another chance. We did one deal and it worked, we did a second deal and it worked, we did a third deal and a fourth and a fifth, and they all worked. And close to seven or eight years after that, we said, "Look, these deals are working, we seem to have a theme here, let's just do this: let's do software only." And that is when in 2008 we founded Thoma Bravo

2. 1:53 – 3:31

   Mentorship from Thoma

   1. OBOrlando Bravo1:53

      and we became a software-only, uh, private equity firm.

   2. HSHarry Stebbings1:57

      Now, Orlando, yeah, (laughs) I sent you a schedule beforehand, but I always go off-schedule and, and you gave me a couple there. I've been very fortunate to learn from great mentors. You mentioned that your early mentor in Thoma. Uh, uh, what were some big lessons for you from him when you reflect on that mentorship?

   3. OBOrlando Bravo2:14

      Oh, everything. A- and I had two. On the investing side, it was Carl Thoma. And Carl taught me the values of investing, what a value investment really is and why. He taught me a lot about leadership, what kind of people we partner with and what kind of people are not for us, they're maybe great for others. Carl really taught me how to do a deal, which I love, which is a big aspect of private equity, right? Because you're buying the whole company, you may have to convince a number of constituencies, you have to value it based on your operating plan, which affects the lender, so a- all those pieces that come together, he really taught me what I call the art of that. Um, and, and it was really, uh, uh, just an amazing, amazing mentoring experience. I, I'm so lucky that he took the time when I was an associate to teach me all that. And...

   4. HSHarry Stebbings3:14

      Good.

   5. OBOrlando Bravo3:14

      ... and that is something that dr- really drives me today with our younger people in, in our firm.

   6. HSHarry Stebbings3:19

      Can I just jump in before you move to the second? I'm too interested. I, I interview obviously predominantly VCs who often say on the show that when you inv- like, to you value investing, it's not a good investment and a good deal is often not a good

3. 3:31 – 4:23

   What does “value investing” mean?

   1. HSHarry Stebbings3:31

      investment. What, what does good value investing mean and why?

   2. OBOrlando Bravo3:35

      Look, we believe every company in the world is worth its future cash flows. We, we just come from that world. We don't believe in multiples of revenue, we don't believe in, uh, a technology might be worth a trillion dollars or a billion dollars because it might do this. We believe that a business in this capitalist world is worth its future cash flow and those p- future cash flow prospects. So we do growth and value, but you earn, you have to earn some sort of yield and multiply that by your growth. And that is what w- what I really learned, those fundamentals of, of what I call value and fundamental investing from, from Carl.

   3. HSHarry Stebbings4:18

      I, I, I love that. We're gonna dig into it more. Tell me, you mentioned a second mentor. I'm too intrigued. Who

4. 4:23 – 5:42

   Orlando’s Other Mentor

   1. HSHarry Stebbings4:23

      was that?

   2. OBOrlando Bravo4:24

      So my second mentor, and this happened simultaneously, is Marcel Bernard, who became chairman of our operating committee really quickly. He was the one who taught our whole organization, including me, how to turn a great innovator into a great company. How to work with existing management to take these high-growth market leaders that have great fundamentals but are not making money today and work with the existing people to also turn them into 40% cash flow businesses. Every single board meeting, and we do monthly board meetings, for 20 years that I would go to with Marcel, I would learn something new. It l- and it was all consistent, e- every tactic that he had and that he tried to talk to people about had the same philosophical umbrella over it. There's so many great sayings he, he used to have which are very applicable to today. Now, what was interesting is Carl Thoma and Marcel Bernard, they didn't know each other. This happened relatively independently until, until Marcel started working with our firm, but they had the same philosophy. One was an investing philosophy and the other one was an operating philosophy, and that was really cool.

5. 5:42 – 7:14

   How to turn a company into a free cash flow machine

   1. OBOrlando Bravo5:42

   2. HSHarry Stebbings5:42

      Can I ask, what does it take to turn a great innovator (laughs) into a great company, and what is the secret to working with that management team to make it a free cash flow machine when it has the potential to be?

   3. OBOrlando Bravo5:53

      What we would do, and what he would always tell us to do, is measure. Take a big problem and divide it into many component parts...... prioritize which parts are more important and then within those parts, measure where you are and begin the journey towards improving that. Delegate authority and responsibility to those individuals that are responsible for each component part. We see even today the world of software, which are much better innovators today than they were 10 years ago, than they were 20 years ago, but these businesses mainly have a big bucket of revenue and a big bucket of cost and they don't really separate their activities and their efficiency in a way that leads to what we call profitable growth. And every time we had a big problem, he would always say, Marcel would say, "Remember, any business problem can be solved. Health is another matter." And he would dive in with the team and as long as that team cared about numbers, knew their business, and wanted to win, everything had a solution to it.

   4. HSHarry Stebbings7:06

      You mention that, the people behind the business. Before we dive into actual markets, companies, investments, I do just wanna actually learn (laughs) a little bit more about you,

6. 7:14 – 8:38

   What are you running from/towards?

   1. HSHarry Stebbings7:14

      if that's okay. I believe we're all a function of our histories, which means we're, we're running towards something and we're also running away from something. W- what are you running from, do you think, first, Orlando?

   2. OBOrlando Bravo7:24

      You know, I'm always on the go. I never like to stay in the same place for too long. Sometimes my family looks at that and says, "What? What is it, he can't stay still?" And, and I really think I'm running from the fear of being trapped, the fear of being isolated, and I, I think about that and part of it is I grew up on an island, I grew up in Puerto Rico, a relatively small island, and to pursue things and to get better opportunities, you always had to leave. Not necessarily for everyone, but that was for me. And maybe that's why also private equity, which is a deal business, where you go from one deal to another, from one country to another, from one state to another, maybe that's why it fits me, uh, really well. But I... Yeah, I have this, this fear of stagnating and feeling, and feeling trapped and isolated.

   3. HSHarry Stebbings8:24

      Can I ask you, just, uh, feeling, like, stagnating, isolated, d- was there ever a time when you felt like your career was plateauing? And was there ever anything that you did to get out of that? I think often, especially today, people feel like, "Am I actually going anywhere? Am I going where I want to go?"

7. 8:38 – 10:49

   What to do when you’re plateauing

   1. HSHarry Stebbings8:38

      Have you ever felt like it was maybe plateauing and what did you do to get out of that plateau?

   2. OBOrlando Bravo8:43

      I felt that my career was a failure, um, in 1999. I, I had come out of Stanford Business School and Law School, uh, with what I thought was this, like, blue chip, pristine, right, education and, and resume and I had very high expectations of myself and a timeline for which I needed to, quote-unquote, succeed, and none of that worked. I was really close in, in '99 to being fired, as I said before. So it wasn't plateauing, it was like, "I'm gonna have to start over." And, you know, I'm a big tennis fan and I used to play tennis and maybe it helped me fight to stay in the game. Just stay in that match, maybe take your time in the change-over, maybe take your time getting, hitting your second serve, and, and in that process also see if there's enough opportunity to change the game. And, um, and then I think it happened and I got lucky. Now, since then, I, I have not felt a, a plateau on, on my career because here's the thing, my job has changed enough over the years and the, the industry that we target has changed enough as well. So if I was doing the same deal that I worked on in the year 2000, I'd probably be pretty bored, feel isolated and plateaued. (laughs) Uh, but, but things have changed enough.

   3. HSHarry Stebbings10:27

      You mentioned the love of tennis there, Orlando. You know, okay, this schedule is not what I had signed up for.

   4. OBOrlando Bravo10:33

      (laughs) .

   5. HSHarry Stebbings10:33

      But you mentioned the love of tennis there. I spoke to many of your mutual friends and they all cited your skills and ability in tennis. I think winning at tennis is about mind talk. When you're set down, how do you speak to yourself to get yourself out of that? And I, I think investing is the same. How

8. 10:49 – 11:36

   Orlando’s Mind-talk

   1. HSHarry Stebbings10:49

      do you think about your mind talk when it comes to you investing and in tennis and what you tell yourself to win?

   2. OBOrlando Bravo10:56

      I tell myself, when working on a competitive investment situation in which there, uh, is another suitor for the company or many, the deal isn't over. You could be losing, you could be behind on price, you could be losing something. Maybe your operating plan is not yet as good, maybe your relationship with management needs to improve, maybe there needs to be more buy-in, but there's time for that. It's, it's really not over, so just stay in it and that's what I was, what I was alluding to before.

   3. HSHarry Stebbings11:28

      Uh, final one before we move into markets and actual investing. You know, people will look at you and look at Thoma and see the incredible success and think, "He

9. 11:36 – 14:20

   What does “success” mean to you?

   1. HSHarry Stebbings11:36

      has everything." When I say the word success, what does success mean to you, Orlando?

   2. OBOrlando Bravo11:44

      I don't have a finite... Uh, I don't see success, for me or for us, as this finite, definable ending goal. Uh, I'll give you an example. We were just at our holiday party, um, for, for the firm, which we have in January because December's extremely busy, and we had 400 people at this holiday party.... and Holden Spade, one of my co-founders, uh, grabbed me to the side and said, "Wow, remember that holiday party we had 17 years ago in San Francisco where we couldn't get a reservation and it was seven of us? This is, this is pretty crazy." And, and I looked at him and I said, "Yeah, but you know what? You know we're only getting started." And, and he nodded. And we've been together, I mean, us partners, we're best friends, it's five of us, we've been together forever. Uh, we love what we do. But I tell you what success means. I, I look at success in many little steps. We can talk about family, friends, work, philanthropy, but I'll take work since we're on that. When we buy a company and we spend a year and a half working to build the trust with all those constituencies and we actually are able to buy one of these great innovators, these great businesses, and then we all collaborate to produce these great margins and growth, right? The, the success story. And then we, we exit that business. I look at that and I say, "What a beautiful piece of art in collaboration the team has produced here." I, I wish I could, I could just visualize it, like put it on a wall, something. But you walk through all those steps and, and it's just a thing of beauty, and that, that's what success in little steps really means to me.

   3. HSHarry Stebbings13:52

      I, I love that, and I spoke to Holden before this episode and, uh, it was, it was a wonderful conversation, I heard that warmth in the partnership that you have. I, I do wanna move to the investing in markets today. You know, it's very disconcerting, honestly, for me, Orlando, I'm seeing this for the first time, investing, in my life, and I'm going, "W- what on earth is going on in the market?" And so from a very high level, how do you assess where we are in the market today at this point, January 2023, with all of the hindsight and

10. 14:20 – 19:34

    The State of the Market Today

    1. HSHarry Stebbings14:20

       perspective you have?

    2. OBOrlando Bravo14:21

       We seem to be in a reasonable place, actually, considering all of it, and the way we look at it is as follows. And, and I'm gonna talk about software, right? That's our core competency, that's what we focus on, and it's becoming a bigger and bigger piece of even private equity, it's a huge piece of venture, of course. But if you look at the public market as a benchmark for the world and you take an index of the profitable software companies, those companies that have margins in excess of 20%, and you put them all together, on average, they trade for around a 25 forward PE, which the industry uses as a leverage-free cash flow. That compares to the S&P 500 at 16 and a half forward PE. That's a good delta and that's a fair delta for higher growth, better cash flow dynamics, and a better business overall. But, but it's, it's, it's fair because if you back into the yield, it seems like it's a reasonable place. It's not ridiculously cheap, but it's not ridiculously expensive either. The big, the big issue and the big confusion in the market is companies that still don't make money, that are great innovators, that maybe will, maybe won't, but that have traded at revenue multiples that are with really the expectation of profitability, 'cause a- most investors think the same way. The revenue multiples on those have gone from an average of 17 times forward to 3.5 today. Where is that gonna end? It's, it's hard to tell and it's more business dependent. Um...

    3. HSHarry Stebbings16:16

       Can I ask, gi- given what you just said, and actually a ve- very reasonable state of the market today as you articulated, is this the new normal and was the prior three years purely, uh, quantitative easing to the extreme by central banks in an artificial environment created by, bluntly, printing cash?

    4. OBOrlando Bravo16:35

       Look, I will never claim that I can predict the stock market or the economy. I can tell you now that things look reasonable. So if, if I w- if you really push me, I would say yes, this is the new normal, because I don't see investors jumping in en masse to do the same thing that in the last 18 months lost them 80% of their money. At least not in the next few years.

    5. HSHarry Stebbings17:14

       I, I, I totally, uh, agree, and I'm British so it's very rare that I would actually push anyone.

    6. OBOrlando Bravo17:19

       (laughs)

    7. HSHarry Stebbings17:19

       (laughs) Uh, but, I- I have to ask then, when we look back at the, the prior few years, how did you and how did the industry approach how to value the companies in the boom time? I'd just love to understand that.

    8. OBOrlando Bravo17:31

       I can tell you how we value them. It's never changed.

    9. HSHarry Stebbings17:33

       Yeah.

    10. OBOrlando Bravo17:34

        It, it really has never changed, is we... And, and I really want your audience to understand this and private equity. When we buy a company, in many cases, that company is unprofitable or has very little profitability, and, and we can talk about examples. But the moment we partner with that team and we buy that business, we are going to completely change, delegating it to them, the way that business is run so that we can combine high profits and high growth.... and we value it based on the earnings that we can produce in partnership with our team year one, two, three, and four, and five, and we back into our return based on a multiple of those earnings that we assume for the future. Now, today, we're assuming a bit lower multiple on those because the cost of capital is higher, and maybe two years ago we were assuming a higher multiple on those earnings because the cost of capital and the financing cost were lower. That has never, never changed. Now, what we did observe in the market is this, uh, hunger for growth, and people were making a lot of money by getting into companies that had exponential growth and accelerating growth, and as long as you got in the deal, it seemed like the deal was gonna work as long as th- there was enough market for the company and other people liked it.

    11. HSHarry Stebbings19:12

        I remember being (laughs) in some of those deals. Uh, my, my, my question to you is, you, you mentioned quite a few times working with management teams to turn those unprofitable companies into very efficient cash flow machines. Respectfully, Orlando, and maybe naively, what do you do to make that transition? I think a lot of people view it as, like, asset stripping and they see Elon today, you know, losing a l- load of

11. 19:34 – 25:08

    How to turn an unprofitable company profitable

    1. HSHarry Stebbings19:34

       workforce. What do you do to turn those machines from unprofitable to highly profitable?

    2. OBOrlando Bravo19:40

       First, we have a big benefit in, in private equity that I, I don't think gets talked about enough, that it's kind of a, a structural benefit that, that this industry of buying companies has, which is the catalyst of a deal helps you make peace with the past and set a new way. That is very hard to do when you're just raising capital and you still have your other investors. That's very hard to do as a public company. You just go more linearly and people tend to think linearly. But a deal can allow you to change everything going forward for what is right today, and put a set of incentives together for the investor group along with management, along with the employees, that drives a certain kind of behavior and performance. Think about it, it's like playing a different sport. In the public markets, the game that has been played for the last decade is the beat and race game. As long as you beat and you race, then your stock goes up and the multiple of revenue and all that. All the sudden, you have one owner with one agenda and one management team, and that game is about maximizing your cash flow growth and how you do that, and focusing on that. So y- we have... Our industry has that structural benefit. Now, the second thing is, Marcel Bernard would always say, "Remember, everyone always has to learn from somebody else." Nobody's born with innate knowledge. Many of these great billion dollar ARR companies are young. They've only been in business 12, 15 years. Their founders are unbelievable. Look what they've created. But they, they may not have been through the old GE school of management or these principles or this mentorship. So if they're open to it and come in with an open heart and an open mind, we can really help 'em do that, and that's something that in the process of getting to know a company we really get to the bottom of.

    3. HSHarry Stebbings21:46

       In the process of getting to know a company, in terms of the, the material substantive, quantitive elements that you have to work with, this was something that a lot of people suggested we talk about. What do you need to see in terms of margins, in terms of close to profitability to be excited? What is it about the fabric of the data, of the financials that makes one interesting and one not?

    4. OBOrlando Bravo22:09

       The story matches the financials. It has to. For example, if you have a very high quality product and engineering team, you're gonna get less support calls so y- the profitability of, of your support business, if you measure it as such, is gonna be higher. If you have products that are easier to use and easier to consume, you won't have to spend that much time in implementation or your implementation margins are gonna be higher. If you have a product that is so important for your customers, your average selling price is gonna be a million dollars or higher and your retention rate is gonna be higher. So everything... Y- you can really tell what is going on with the quality of the business through the numbers and you check that back by looking at the leadership, by looking at the technology, by looking at their processes, by looking at a number of aspects within th- each functional area or even, even regional area. What, what we really look for is give us very high quality of revenue, give us a top line that is very stable and has enough room to grow, and that's where d- we pay different values for different, for different entities and different companies. Second, give us a management team that we can work with, that is open-minded, that wants to win and that does care about profitability. And then third, give us enough inefficiency so we can earn a differentiated return. If, if you have a perfectly run business, then it's gonna sell for a retail value on that cash flow and we may not have enough delta to, to create an additional return from our efforts and, and from our work.

    5. HSHarry Stebbings23:59

       What are the most common ways you see inefficiencies where you can provide efficiencies to gain further profitability in the future?

    6. OBOrlando Bravo24:08

       As, as these businesses grow so fast, um, and it's not their fault, th- they really end up with too many people, too many processes, too many layers, um, and...... all that and that journey, actually, it- it's not only causes inefficiency but hampers the future growth of that business. More approval processes, slower decision-making, uh, a number of issues that, in our world, the more efficient you are, the faster you should grow, and it makes sense both from a numbers standpoint and operationally. To be really direct, it's all over the place. There's no silver bullet of, y- you know, the- the world is doing something in engineering or product management or distribution or marketing that- that is consistently inefficient. It- it's really all over.

12. 25:08 – 26:04

    Elon & Twitter

    1. OBOrlando Bravo25:08

    2. HSHarry Stebbings25:08

       Can I ask you a bit of a divisive one, which is again very non-British of me.

    3. OBOrlando Bravo25:12

       (laughs)

    4. HSHarry Stebbings25:12

       But, you know, does Elon reducing the size of Twitter's team so much and Twitter still working... Everyone thought Twitter down, Twitter shut down. Twitter's still performing. My tweets still send. Yours still send, and we still get likes. Has it shown a new roadmap for actually the radical reduction in workforce needed to actually maintain great and core functionality?

    5. OBOrlando Bravo25:37

       Well, it's a really interesting case study. I, I don't know the details, um, enough operationally and process-wise, and I don't understand that business well enough. We do enterprise software business-to-business, right? There's a consumer. It's very interesting, interesting company. But it, it is a case study for Silicon Valley to take a look at, and let's see how, where it ends up in three to four years. It could end up great.

    6. HSHarry Stebbings26:03

       You mentioned

13. 26:04 – 29:26

    VC vs PE

    1. HSHarry Stebbings26:04

       value there. Uh, again, I, I predominantly interview VCs, uh, and early-stage VCs very often where, you know, price, it doesn't really matter. If you're paying 50 or 75, if it's a generational defining company, it doesn't matter. At your stage, I think it's a very different game. I- I'm interested. Given the many years-

    2. OBOrlando Bravo26:21

       (laughs)

    3. HSHarry Stebbings26:21

       ... of very successful investing you have, how do you reflect on your own price sensitivity, Orlando?

    4. OBOrlando Bravo26:28

       Oh, price matters. (laughs) Uh, pr- pr- price really matters. Um, it's, it's interesting because many of the principles, even if you're doing a seed stage and you're doing a buyout, many of the investment principles are the same. You may have in the early stage less data, uh, of course, um, than, than you have in terms of being able to see trend lines and being able to see... But your equity check is, is small, so you're diversifying the risk. In a buyout, you could be riding a $10 billion equity check with your partners, and you cannot get that wrong. That, that would be really fatal, uh, making a mistake on something that big, uh, which is an interesting disconnect, um, sometimes between the technology world and technology executives and buyout. The risks that that company can take with an investment of that size and, and the chances they can take on different things and, uh, and experimenting a different way are very different than when somebody's invested $10 million and there could be some behind it.

    5. HSHarry Stebbings27:41

       Mm-hmm.

    6. OBOrlando Bravo27:41

       And the expectations are different as well.

    7. HSHarry Stebbings27:43

       How do you think about downside protection and loss ratio? Again, in venture, it's a lot... Uh, you know, great performing funds are made by one breakout company, and I, uh... You know, a very prominent investor in P funds and just globally said to me the other day, "And actually, the poor performing funds in P, uh, are actually ones that just have one loss because it's so much bigger deals." How do you think about downside risk when entering and then also loss ratio?

    8. OBOrlando Bravo28:11

       That, that person is right. You just cannot have a big loss. You, you really can't. Uh, that's a big... It would be a big hole, um, to deal with. And not only is it, would it be that loss, it's also when, when things are not going that great in a buyout deal. These are really big companies. You're gonna spend seven or eight years of your entire life dealing with that, which stops, stops you or pushes you back from doing many other good things that you could be doing. There's no such thing in buyouts and private equity as triaging your portfolio and deciding what you throw away and when you keep going, which, which in another way to put it is, is actually a big motivator to management teams to partner with you, because you have no choice but to stay the journey- (laughs)

    9. HSHarry Stebbings29:10

       (laughs)

    10. OBOrlando Bravo29:10

        ... uh, with that, with that business and that entity.

    11. HSHarry Stebbings29:13

        I, I, I often say it's sometimes helpful to burn the boats. (laughs) Um, it leads, it leads to resourcefulness that you never knew you had. Um, I, I, I totally, uh, agree and, and get you, though. Uh, I... Again, I'm, I'm just gonna, (laughs) gonna ask

14. 29:26 – 31:33

    Did Orlando overpay for Anaplan?

    1. HSHarry Stebbings29:26

       it 'cause I'm gonna killed for not asking it. Uh, you mentioned kind of price matters. Some people said, you know, "Cooper, Anaplan, they were quite high prices." Um, how do you think about that? On reflection, is it, "We did pay high prices"? Uh, how do you respond to that suggestion?

    2. OBOrlando Bravo29:44

       I really appreciate you asking that. Now you're really showing your British side.

    3. HSHarry Stebbings29:48

       (laughs)

    4. OBOrlando Bravo29:48

       Okay. This is-

    5. HSHarry Stebbings29:49

       I'm so- I'm, I'm so uncomfortable asking you. (laughs)

    6. OBOrlando Bravo29:51

       Th- this is very good. This is so good. (laughs)

    7. HSHarry Stebbings29:54

       (laughs)

    8. OBOrlando Bravo29:54

       I love this. It, it, uh... Look, we've been doing this in, in the same way using the same philosophy that I described for 25 years now with the same team and the same leadership team. It's grown a lot, but we still have the same leaders at our firm. And I almost cannot tell you of a deal where a peer or competitor or s- or, or an outsider... I cannot almost say one single deal where they haven't criticized us for paying too much.... it, it, it's truly, truly amazing. So, Coupa, Anaplan, and whatever other, uh, investments are no exception. (smacks lips) The thing that I find interesting in that comment is, that may be true if we were gonna leave those businesses exactly the same, but whoever's saying that doesn't know what our business plan is.

    9. HSHarry Stebbings30:49

       (laughs)

    10. OBOrlando Bravo30:50

        Doesn't know what we're gonna do operationally with that business from a cash flow standpoint. And, and that's why an outsider looking in doesn't really have a basis of knowing what our free cash flow is gonna be in year one, two, three, four and five, and do we have a very credible, proven way, an easy way for us to get there. Because d- we will change, like we do when we buy a company, the way that company is run and we're gonna add a lot to it.

    11. HSHarry Stebbings31:24

        Speaking of kind of getting there, you mentioned three, four, five in terms of the years, what matters also is the time that you exit, and when we think about exit

15. 31:33 – 34:47

    How to think about exits in PE

    1. HSHarry Stebbings31:33

       environments, how do you think about exits for new deals in terms of strategics, in terms of IPOs, PE trades, now, given where we are?

    2. OBOrlando Bravo31:43

       I mean, in our history, we have mainly exited to strategics and other financial buyers and, and there's a reason for that is the IPO for our companies doesn't give us that much in itself because our companies generate the cash flow that is needed to fund their investments on their operations and even to fund acquisitions that they wanna do. So, in an IPO, you typically have to dilute your ownership to raise cash that you don't need. If you needed the cash because you're a younger company or right now you're not profitable, that could make sense, but typically that there's no value there for us. On the big companies, I actually look at it as a big positive for the ability to exit as follows. First, remember, in order to exit, you just need one buyer. You don't need 100. Only one is gonna buy your company. And second, do you have a better odds of exiting to the giant tech companies that are still growing by leaps and bounds by selling them a market leader with a given core competency with two billion in revenues that is by far once again the market leader in a given vertical, in a given application horizontal, in cybersecurity, in identity? Or do you have a better chance of selling them a company that's number 10 in that field? You may get more comfort in saying, "Ah, there are more buyers that can w- cobble up the money to buy the small company," but you just need one and, and buying quality on the market leaders is really all about the, the exit potential. Now, we don't sit here too much and worry about the exit because we can't control how much a buyer is gonna like a company or not from a strategic standpoint. What we can control is having the best-run company in that field and when times get really bad, the best-run company always wins because then you'll have 40% cash flow margins, you're very well put together, you're budgeting conservatively, you're not missing your numbers all over the place, you have the confidence of your lenders, you have the confidence of your investor group, and when times get tough, the ones that are stumbling, those are the ones that you can go out and buy at more attractive prices.

    3. HSHarry Stebbings34:17

       When you sell to these strategic buyers, obviously you make returns and you provide great cash back to your investors. There's a common trait now, we've seen venture firms explode in terms of their fund sizes and the k- kind of trope is that with an increase in fund size, you have a reduction in performance. A lot of people will suggest, they

16. 34:47 – 36:13

    Does increased fund size mean decreased performance?

    1. HSHarry Stebbings34:47

       ask this, we've seen obviously Thoma Bravo increase hugely in terms of fund size. How do you think about the notion of when you increase fund size you decrease performance?

    2. OBOrlando Bravo34:56

       The LP community is really, really smart and there is a direct correlation between that, that we cannot argue with and it is there. The reason we've increased fund size is not because we can, but it's because we really like buying the number one or two player in each of the many markets within B2B software or enterprise software that we're in. We feel there's a big difference in value and, and it, it depends on which sector, but in, in many there's a big difference in value in those. There's also a lot less risk. There's also a lot more stability. So, when you look at the world of software, those market leaders are now really big (laughs) and 10 years ago there were a lot smaller and 20 years ago they were nonexistent in the world of SaaS because that didn't exist. So, we've been following the industry as we grow 'cause it does, despite all the market turbulence and evaluations, it is compounding at a very aggressive rate.

    3. HSHarry Stebbings35:58

       And there's a barrier to entry, I imagine, where when you think about it, if you have to buy the top one or two and the price is here, there is an inherent barrier to entry which says my fund has s- to be that size if I'm gonna have any form of meaningful diversification at all. Do you think diversification is

17. 36:13 – 37:39

    Is Buffet right about diversification?

    1. HSHarry Stebbings36:13

       a complete BS myth in investing by the way? I've seen this so many times where, you know, even your Warren Buffetts of the world have said diversification, poof, overrated, and then in venture it's the central thesis of our whole business. How do you feel when you hear the importance of diversification?

    2. OBOrlando Bravo36:28

       On that, I stand with Warren Buffett. Surprise, surprise.

    3. HSHarry Stebbings36:32

       (laughs)

    4. OBOrlando Bravo36:32

       ... um, per fund, we'd like to have 12 companies, maybe 15. But think about it, right? If you have an investor, private equity or venture firm, that claims that they make a big difference in their companies, that they're there with those companies operationally, that they, they change them in a positive way, and you have 40 or 50, there is no way you have the time to do that. It is, it is im-... operationally impossible to do that. So if you really focus on having three new platforms a year, maybe four, and you have enough leaders at the firm with enou- enough experience that are mentoring the next generation, you can handle those assets and really pay attention to them on a weekly and monthly basis. We meet with our companies monthly. Our board meetings are monthly from 8:00 to noon on every one of these, these entities, so it does take a lot of time. And that's where if you diversify too much, you begin to hurt the operating

18. 37:39 – 40:04

    Orlando’s Biggest Miss

    1. OBOrlando Bravo37:39

       performance of, of, of your companies.

    2. HSHarry Stebbings37:42

       You mentioned earlier not being able to have a miss in your model and in the market itself. Orlando, have you ever had a miss, and what did you learn from it? I had a big miss earlier last year. I lost 28 million dollars in one deal, which was painful for me. It's small change for PE, but for venture, it's not small change. (laughs)

    3. OBOrlando Bravo37:59

       (laughs)

    4. HSHarry Stebbings37:59

       Um, and I learned a lot. Have you had a miss, and what did you learn from it?

    5. OBOrlando Bravo38:03

       Oh, we've had misses. (laughs)

    6. HSHarry Stebbings38:06

       (laughs)

    7. OBOrlando Bravo38:06

       We, we, we, we unfortunately have, and, and in some cases, we've been fortunate that in that fund, we also may have had some others that were right, uh, outsized private equity returns that look more like venture, so we could handle those and our investors could handle those as well. So many lessons. We had a really big deal, a really big company we bought at one point, and I, I won't name it because management has done a great job and they're doing well and they're gonna do great, and they tried very hard together with us. But in that deal, we bought it because it was a good value, but we ignored some of the trends that we clearly saw on diligence on one of their product lines. And the trends ended up being like we diligenced them, (laughs) but we didn't think they were gonna get that bad. It's almost like, why do you do so much diligence if you had this in front of us? And, and I was on, on that deal and I thought the other product line would really collapse that and the lines would cross and the value was good enough to get us into, into a good situation, and, and ultimately, that did not work. We, we have made mistakes where in transforming a company from a great innovator into a great business, uh, we've made investment mistakes in that company, partly because the companies were too big or big enough that management had become very strategic in nature, and they didn't, uh... they had lost touch with what pulled the train, with the operating realities. So in making trade-offs, they were a bit out of touch with the business, and then by the time we came back and reinvested in some areas, we lost too much time and it was a bit too late. But we've had many, um, we've had many mistakes and we try not to repeat them.

    8. HSHarry Stebbings39:59

       I always believe in our business that our decision-making process is the product that we sell.

19. 40:04 – 42:52

    Orlando’s Decision-Making Process

    1. HSHarry Stebbings40:04

       Um, my question to you is, when we look at an incredible institution like Thoma Bravo, what is your decision-making process? How do you coalesce and decide to buy or not to buy?

    2. OBOrlando Bravo40:14

       Well, we know exactly what we're looking for. We are... In B2B software, we know the template that we wanna buy, and we have our own target list, hundreds of companies that maybe we have tried to partner with them before, maybe one of our portfolio companies has competed with them before, maybe one of our software assets is their partner, and, and we've known them for a long time. So it's also like when we engage, uh, w- with a company on a deal, it's not like we're doing due diligence on that for the first time. We could have been watching it for 15 years, quarter over quarter, and known why they missed, why they beat, what... how management has been changing things. So we know, we know exactly what we wanna buy. Now, one of my biggest fears in investing, and this may, might apply to, to exactly what you do into venture investing, is, how far away from the asset does the investment committee get? As I like to say, something happens operationally, they give that... the CFO reports on a backwards-looking basis, then a representative or investment banker takes those numbers and creates I don't know what from it, and then our deal team gets that, and then our deal team does something, gives it to the investment committee, and you're so far removed from the operating realities. And we try... What we try to do is... Actually, what we do is we have at least a third of the management committee be involved in that deal day to day, and there we f-... therefore, you have two leaders and two senior partners that can talk about it and are living that journey while you're analyzing the, the investment opportunity.

    3. HSHarry Stebbings41:48

       Does everyone have to approve the deal? Do you agree with consensus decision-making or does some dissent actually breed better decision-making?

    4. OBOrlando Bravo41:58

       We don't do any controversial deals. We are 100% everybody consents. If somebody really has a problem with that deal, there's something really wrong. Once again, we've worked together, all of us, for almost 20 years. We're looking at the same industry. We have the same philosophy for that industry. We have the same operating playbook for each company. We have the same way to add value. So if there is a dissent, there's something very strange going on. For what we do, I 100% agree with consensus, and that's the way we've always done it.... now, if you're a firm and you have healthcare, you have tech, you have manufacturing, you have many, then you're chasing, then you have a different environment or maybe the, the job of the investment committee is different in, in that, in that case.

    5. HSHarry Stebbings42:51

       I spoke to one of

20. 42:52 – 44:32

    How to Manage Employee Mindset in an Economic Downturn

    1. HSHarry Stebbings42:52

       the largest institutions in the world before this and they said one of the most challenging things our managers and PE are facing is how do you manage the right mental balance in your team, and especially younger people in your team, on investment committee where you're willing to invest in a bluntly tanking market as we've seen over the last year, but also not catching a falling knife and pushing them too hard? How do you strike that right mental balance within the team and the investment committee?

    2. OBOrlando Bravo43:18

       It goes back to operationally, are, are you buying quality, number one? And secondly, with what you're gonna add to that from our perspective, do you have a proven way that you've shown it before, that you've done it many times, where you can have this business at a level of margin that then the price you pay makes a lot of sense relative to where the market is today? We don't depend on, as we used to joke around, buying high in order to sell higher.

    3. HSHarry Stebbings43:52

       (laughs)

    4. OBOrlando Bravo43:53

       It, it, it, it's not at all, and you're gonna hold these assets for a number of years, usually four, maybe five, in that range. So it all goes back to fundamentals. Now, you, you don't wanna catch a falling knife in terms of the revenue trajectory of that business, so there's where you spend so much time on revenue quality. What's the momentum showing like month to month? Where's it growing? Are they acquiring enough new customers? Is something slowing down? Is something gonna surprise you? What's the competition doing? What are the pricing trends? That's where you spend so much diligence, time, in actually seeing it so that you see some positive trends when you,

21. 44:32 – 46:37

    Orlando’s Relationship to Money

    1. OBOrlando Bravo44:32

       when you enter the journey.

    2. HSHarry Stebbings44:33

       I want to take a slightly different tact. When you have the, the success that you have, um, bluntly financial profiles change over time, and I- I've often thought about kind of relationship to money, um, uh, and it's one I've struggled with in my youth. Um, how do you analyze and think about your own relationship to money today, Orlando?

    3. OBOrlando Bravo44:52

       You mean me personally?

    4. HSHarry Stebbings44:54

       You personally. I, I remember, uh, I was 21. I made my first million and in my head, like, you know, we all, Who Wants to be a Millionaire, this game show.

    5. OBOrlando Bravo45:01

       (laughs)

    6. HSHarry Stebbings45:01

       And when you're a millionaire, you are happy, like that, you've got everything in the world, and I sat there on my balcony at 21 and I was with no friends and few relationships in my life, and I've never been more depressed. (laughs) And, uh, it was, that was the hardest moment 'cause it's like the thing I thought always mattered didn't. How do you think about the relationship to money?

    7. OBOrlando Bravo45:23

       It's so interesting you say that, and thanks for being open about that. Uh, it's like when I didn't have any, I was, I had a deep relationship with money 'cause I was deeply stressed out about it. I remember starting out, I would go to my bank account every other day to see if it was a little higher or not. (laughs)

    8. HSHarry Stebbings45:40

       (laughs)

    9. OBOrlando Bravo45:40

       And, and, uh, and I would get really fired up when it was a little higher and, and everything else, and, and it was a very complicated and negative relationship with money. And once I had enough, I really don't have one. But to your point, it doesn't, it hasn't cost me any happiness, at all. Like right now, somebody asked me, "Oh, when you and your team have an exit and have this great deal and it's a big home run and it pays off everybody, what do you do?" And you feel good because you proved something and y- it's that piece of art that the team painted and you feel so proud of your colleagues and of the team and f- what you stand for, that it actually worked, that it actually produced something great. But it's not... The, the money is that, you just go onto the next deal or the next opportunity. It's just, it's very, it, it's not about that, really, I, yeah.

22. 46:37 – 49:32

    How to instill values in your kids when they grow up rich

    1. OBOrlando Bravo46:37

    2. HSHarry Stebbings46:37

       It's, it's not about that, but you also have, have children and, and it does impact one's ability in terms of their parenting. How do you think you instill the same values, discipline, hunger in children when they are brought up in very different, you know, financial situations to going to (laughs) your bank and like-

    3. OBOrlando Bravo46:55

       (laughs)

    4. HSHarry Stebbings46:55

       ... pleading for, you know, a dollar more? How do you think about retaining that ambition and hunger in children when they are brought up in different circumstances?

    5. OBOrlando Bravo47:04

       Yeah, but kids, kids are great. Look, um-

    6. HSHarry Stebbings47:08

       (laughs)

    7. OBOrlando Bravo47:08

       ... w- what one thing is, um, and, and I also speak for all my partners, w- we're all like this, um, nothing goes to anybody's head. We're normal people. Uh, we struggle with personal things and, and with life and need support just like anybody else. We don't think we're better than anybody because we may have had a given wealth streak here or, or something. We really don't, and we behave that way with our kids and with our family, and for me, my older kids, they are ridiculously hardworking. I was actually talking to my daughter yesterday and I was trying to convince her to work less hard. It's like th- you're, you're crushing yourself, she's, she's this incredible performer, uh, incredible scientist. My, my son is a college athlete pushing himself, just doing the training and the incredible demands of school and combining that with friendships and relationships, and it's, uh, uh, they've... My, my kids are, my younger kids, I could see the same, they're just very dedicated, hardworking. For, I think... I, I'm now getting to understand my mom a little better, uh, because my mom certainly wanted me to work hard and she really helped me. But now she always asks me, "Are you happy? Are you happy? Are you happy?" And I go, "Yeah, I'm h- I'm happy." And at the end, that's what a parent really wants and you have no control over.... the thing that you can do, um, and I have four amazing kids, is, is always be present and try to support their dreams and not put your background or your dreams into anything. And Harry, going back to what you said as well, um, sometimes growing in a family that, that has more wealth and opportunity could be good and bad because then the individual may have to measure themselves by another individual (laughs) in that household and they may feel that they may never get there in the same way. Would they be valued in the same way? Uh, their accomplishments could be questioned. Oh, you may have done X, Y, and Z because you had another opportunity. You may, you may be in job interviews and people may think that you're not as hungry.

23. 49:32 – 51:38

    Happiness

    1. OBOrlando Bravo49:32

    2. HSHarry Stebbings49:32

       I, I, I want to be honest. You said, "Are you happy?" Your mother asked that. I'm never happy all day, all day. And I don't mean to be like too open with you, but like, I'm always failing at something. You know, if you crush it at work, I'm failing at friendships, I'm failing at being a son. My mom's got MS. It's tough. I'm failing at that 'cause I'm giving everything to work. I'm always failing at something and I'm never happy because of that and it's, it's never enough. (laughs) Sorry, I didn't mean to use this as a counseling session. But what would you say to me if you were my parent (laughs) and you said, "Are you happy?" And I said, "No, I'm never happy even though I have everything that I could have dreamed for five years ago and more"?

    3. OBOrlando Bravo50:10

       How old are you?

    4. HSHarry Stebbings50:12

       26.

    5. OBOrlando Bravo50:13

       Yeah. Yeah, you're in the middle of it. Um, I, I think that's a really tough... For me, late 20s, early 30s were a really tough part of, of life. Um, you are out there once again trying to crush it at work, but how do you do that? 'Cause you have in the w- in, in a way you have like, this endless energy, but how do you balance everything else? And you haven't... At that age, I feel like you ha- you don't have enough of an established rhythm of life and necessarily who you are and you're looking a... You, you're going through the journey of finding that. F- from a personal standpoint for me, things got clearer in my mid-40s.

    6. HSHarry Stebbings51:04

       Huh. Why, why, why is that?

    7. OBOrlando Bravo51:04

       In terms of who, it was, in terms of who I was, um, more comfortable with that, with what I wasn't great at and I did less of that, um, what I needed, what I was doing that I did not need and was not beneficial to my relationship with friends and others. It, it, it just became clearer. Now, that was my journey, which necessarily is anybody else's. Uh, but in my late 20s, early 30s, it was,

24. 51:38 – 54:07

    Work-Life Balance

    1. OBOrlando Bravo51:38

       it was tough.

    2. HSHarry Stebbings51:40

       Can I be honest? I think, you know, one of life's greatest joys is, you know, a wonderful partner and you have a wonderful wife, but you're also at the top of your game and have been for years and years. I'm terrified that I won't have a meaningful relationship just 'cause I give my life and body and soul to what I do and I love it, but like, then I will be alone and I'll be Rich Uncle Harry to my brother's children (laughs) which is a sad future I don't want. How do you maintain... (laughs) You're like, "Jesus, Harry, you owe me invoice for this counseling." (laughs) But like, how do you maintain a great marriage and be the top of your game in such a demanding industry?

    3. OBOrlando Bravo52:16

       One thing I figured out and this was... I, I don't, y- you know, you, you asked me the question. This is not meant to be advice. I tell you what I went through.

    4. HSHarry Stebbings52:27

       Yeah.

    5. OBOrlando Bravo52:28

       There was a time in my life when I wanted to spend more time cultivating those relationships and the relationship with my kids. And therefore, there's not enough time in the day 'cause you do need a little bit of sleep. Um, and, and what happened was I was forced in a way, not through coaching, but just through choices to delegate a little bit more, to let go of micromanaging things at work, to maybe not be in every single management meeting. I could be in the important ones. I could be in places where I could add value to my colleagues. I focused more on mentoring people and having people be more successful than I was in my organization than trying to do things as an individual contributor. And the more time I would spend on what you're fearful that you won't have, the better the business got by far. I mean, it's not even, it's not even close.

    6. HSHarry Stebbings53:34

       (laughs)

    7. OBOrlando Bravo53:34

       And it was, (laughs) it was very clear, uh, that, that letting go was a very, very good thing for, for work and business, and in a way it's like, let others do their job. Let others do their thing. Check in once in a while and be more, play more of a supporting role, and that may apply to your companies as well.

    8. HSHarry Stebbings53:55

       I think it does. I think it's just about letting go and being willing to. Um, but, uh, (laughs) I, I wanna move into a quick fire before I, uh, take you entirely for a counseling session. So, I say a short statement, you give me your immediate thoughts.

25. 54:07 – 55:05

    Orlando’s Favorite Book

    1. HSHarry Stebbings54:07

       Does that sound okay? (laughs)

    2. OBOrlando Bravo54:08

       That sounds great.

    3. HSHarry Stebbings54:10

       So, what's the favorite book and why? What are you like, "Harry, you should read this." It might have changed given how fucked up you heard it. (laughs)

    4. OBOrlando Bravo54:16

       (laughs) Given... No, given the discussion we've just had, you gotta read The Power of Now.

    5. HSHarry Stebbings54:22

       Huh. Wh- why? What, what did you love about it?

    6. OBOrlando Bravo54:24

       It, it's, uh... Now, I did read it in, uh... My... I actually read it in my early th- 30s. Um, it's, it's kind of like a very spiritual book. How can you be present at all times? How could you be the soul that is, that is always... It's much deeper than this, but always in the moment.... and not too worried about the past. Having no use, in a way, for the past, which in investing, right, is a no-no. You learn from all your mistakes. And it doesn't say that you don't, but- but it- it really, um, inspires you to be very present.

    7. HSHarry Stebbings55:01

       What's your biggest fear? Like, my biggest fear is being rich Uncle Harry and never experiencing

26. 55:05 – 55:15

    Orlando’s Biggest Fear

    1. HSHarry Stebbings55:05

       the beauty and joy of a great marriage and relationship. What's your biggest fear?

    2. OBOrlando Bravo55:09

       I think it's what I'm running away from. It's stagnating. It's feeling trapped.

27. 55:15 – 56:21

    Orlando’s Biggest Strength/Weakness

    1. OBOrlando Bravo55:15

       It's feeling like I'm going nowhere.

    2. HSHarry Stebbings55:16

       I- I- I totally get it. Um, can I ask you, what's your biggest strength and what's your biggest weakness when you reflect on yourself?

    3. OBOrlando Bravo55:23

       I feel, uh, I'm very good at bringing people together. This thing that we do requires so much buy-in and collaboration, and people are re-rowing towards the same objective, and- and I- I- I think I have, um, the patience and I like talking to people and I like mentoring people and I like, uh, inspiring people to do the right thing. And- and that's- that's why I chose, in a way, these deals and owning a whole company versus being a public investor where you maybe are making choices without talking to everybody and- and really trying to move an organization together. I think a weakness is I have a pretty short attention span.

    4. HSHarry Stebbings56:06

       (laughs)

    5. OBOrlando Bravo56:07

       Uh, so I- I... Right? So I like working on many projects because I'm not the right person to only do one project.

    6. HSHarry Stebbings56:16

       If you had the chance to sit down with yourself when you left the resuméed educational

28. 56:21 – 57:54

    What would you tell your younger self?

    1. HSHarry Stebbings56:21

       background that you had, but at the start of your career, and you could advise yourself something, what would you tell yourself?

    2. OBOrlando Bravo56:28

       I would tell myself to relax, first and foremost, and second, to remember to be real. And I- I- I t- I tell you why. On relaxing, I had very clear and finite timelines to achieve things, and that is out of your control, and by doing so, I was putting so much pressure on myself that the artist in me and the- the artist in you was not allowed to do its work and its thing. And for me, it was not u- not until I was able to step back, relax and get some perspective that then things started getting better. And- and the second one is to be real, and maybe that's, um, m- maybe it's part of my background being Latin American and Puerto Rican. I always looked up to the people that invented the private equity industry, which are still leading many of these firms. I loved what they did, uh, they were role models, but in a sense, I wanted to be just like them. Uh, imitate the way they dress, the way they talk, the way they did things. And it was on- uh, until I was really... and somebody said, "Just- just be yourself. Just do it that way," that once again, whatever you have to contribute, both in work and philanthropy and life, it just got

29. 57:54 – 58:19

    Timelines for Life

    1. OBOrlando Bravo57:54

       better.

    2. HSHarry Stebbings57:54

       You said about timelines. Do you set timelines for yourself? I always said, you know, 28 this, 30 this, 32 this. Do you set timelines for yourself?

    3. OBOrlando Bravo58:03

       I used to, but no longer. It- that- that did not serve the intended purpose, uh, for me at the time. You- you know what it served? It- it served when I would miss it, miss the timeline. (laughs) It's like missing your budget, it was a disaster, so why do it?

30. 58:19 – 1:00:04

    Why is philanthropy so hard?

    1. OBOrlando Bravo58:19

       N- don't torture yourself.

    2. HSHarry Stebbings58:20

       Penultimate one for you. Why is philanthropy so hard? Jeff Bezos has said it's harder than making money. Why is giving money harder than making money?

    3. OBOrlando Bravo58:28

       As you know, I have the Bravo Family Foundation and we do an inordinate amount of incredible work in Puerto Rico, and also, like Thoma Bravo, we're only getting started. We're gonna change things to the positive. It's a tremendous effort from the team. This is the deal. When I go through the budget of a company, you see this hopefully wonderful learnings coming out from all the work and you have revenue and cost and you can measure that. When you do a budget for your foundation, you only have cost. (laughs)

    4. HSHarry Stebbings58:59

       (laughs)

    5. OBOrlando Bravo58:59

       How do you measure... How do you really measure your impact and whether that effort and those dollars are producing the desired impact, and what is success? In capitalism, you are ruled by the P&L, by your income statement, and we love that. It's clear. It's your report card. Are you winning? Are you losing? Do you need to change things? In philanthropy, if you can change one community, and we work in many of them, is that enough? We work with rising entrepreneurs. We've launched... By the end of this year, we would have launched 50 companies and we've been at it not too long. Is making one of them great enough? Do they all have to succeed? How do you measure success and what are the measur- measurement points? And that's what is really, really hard about philanthropy. So before you keep throwing more and more resources at it, you have to come to grips with all that, which is a lot more complicated in the nonprofit world.

    6. HSHarry Stebbings1:00:00

       Fascinating. I hadn't thought about the two inputs. There's obviously the incoming and the outgoing.

31. 1:00:04 – 1:01:33

    Orlando’s Five Year Plan

    1. HSHarry Stebbings1:00:04

       Um, final one for you, Orlando. I love this. Uh, next five years for you. You don't do timelines, you don't do those, but I'm gonna ask it anyway. If we do this in 2028, where- where is Orlando Bravo then?

    2. OBOrlando Bravo1:00:17

       Oh, this is where we're gonna be. Well, we know that. (laughs)

    3. HSHarry Stebbings1:00:22

       (laughs)

    4. OBOrlando Bravo1:00:22

       We- we- we, as a team, and once again, I'm talking about work, we would have, um... we would have achieved another step function increase in what we do and in our mission, and we have had, as an organization, a step function change to the positive on every crisis and every challenging environment. Otherwise, it's been steady state growth. But proving once again, and you were mentioning some big deals, proving once again the value of operations, the value of partnering with management, the value of positive change, the value of ethics in business, in doing things right and turning great innovators into great companies, and doing it once again in a really challenging environment, that's gonna create another- another positive step for us.

    5. HSHarry Stebbings1:01:14

       Orlando, I- I really mean this. It's shows like this which make me realize how much I love what I do. I'm so grateful to you for being so open with me, for advising me, and- and for being such a star. So thank you so much for joining me.

    6. OBOrlando Bravo1:01:28

       Harry, you were... This was awesome. Thanks for being so open and- and this was great. Thank you.

Episode duration: 1:01:33