In this special episode of Thoma Bravo’s Beyond the Deal, Managing Partner Holden Spaht and Partner Brian Jaffee turn the microphones on each other.
They share how they joined Thoma Bravo, what it was like in the early days, and how mentorship, accountability and entrepreneurial ownership shaped their careers. From cold emails and crowded cubicles to leading major exits, this episode offers a candid look at leadership, partnership and building performance over time.
This podcast is for informational purposes only and does not constitute an advertisement. Views expressed are those of the individuals and not necessarily the views of Thoma Bravo or its affiliates. Thoma bravo funds generally hold interest in the companies discussed. This podcast should not be considered as an offer to solicit the purchase of any interest in any Thoma Bravo fund.
March 5, 2026
19:58 minutes
Carl Thoma, one of the things that I've heard him say, and I've now heard Orlando [Bravo] say a bunch that I think has really stuck with me as I've kind of gone on my career here, was, "It's okay to make a mistake, but it's not okay to make that same mistake twice." And it's such a simple but pretty profound statement. And I do feel like that kind of lives inside of our firm everywhere.
Welcome to Thoma Bravo's Beyond the Deal. I'm Orlando Bravo, founder and managing partner at Thoma Bravo. Today, we're doing something a little different. Instead of sitting down with a CEO, Thoma Bravo managing partner Holden Spaht and partner Brian Jaffee are turning the microphones on themselves. They'll share how they got their start at Thoma Bravo, how they've grown with the firm and how they work together to drive results. It's a candid look at leadership, mentorship, and what it really takes to sustain and perform over time.
You and I have worked together now about 12 years, but I was trying to remember the origin story of how you came. I remember it was a great class, but talk a little bit about your background maybe and the decision to come to Thoma Bravo, how that came about.
Yeah, happy to. I started my career at Merrill Lynch in the investment banking group, actually in 2007, so right as the financial crisis was about to hit. And was in the leveraged finance group, learned a ton. And actually, that was the point where I really got to see and understand private equity. I always knew I wanted to go into finance. I wasn't sure exactly what, but knew investment banking would be the right jump off point. Got this great experience, even though deal flow at the time was tricky, but really got to see the market structure and how it all worked in these different private equity firms. And I realized pretty quickly I wanted to be an investor, and what does that mean and how do you do that?
And so I was fortunate enough to get a job at Veritas Capital, another private equity firm based out of New York. Really cut my teeth there as an associate for three years. Then I went to business school at University of Chicago. And at that point, I was starting to think about, "What do I want to do next in this kind of post MBA role?" And I was doing a bunch of networking and actually came across A.J. Rohde, one of our partners, and reached out to him cold. And I'll never forget-
Wow.
Yeah, so I was doing some sourcing-
Good for you.
I was doing some sourcing. You had to be-
I didn't realize that, okay.
Yeah. Coming out of Chicago, you had to be maybe a little scrappier. AJ also happened to go to Chicago and was a Midwest guy. I reached out to him. He responded in three seconds and basically said, "I just had twins and work is on fire. Ping me in three weeks." I was like, "Three weeks?" He was like, "Ping me in three weeks, I think we're going to run a process. We're probably going to hire a couple VPs." So I reached back out to him, had a great conversation. He ended up putting me into this process. You guys were actually at the time, in the process of raising Fund 11. And so you needed a couple of post MBA VPs to help continue to build out the firm. And I was lucky enough to go through that process and get an offer.
I will say the interview process, looking back on it now, it's so funny to think about. But again, I'll never forget, at the time we were in the Transamerica Pyramid. We were up on the 32nd floor, had a pretty small office. And I walk in and literally in the lobby of our office, you guys had constructed a cubicle because we ran out of space for our associates. And so this poor guy was sitting. I remember he had his dry cleaning all over the place and he was on 100 phones. And we were kind of coming in and out of the lobby as part of our super day. But the energy of the office and just kind of seeing how everybody operated, how collegial it was, I'll never forget that.
It's kind of a sad story in a way. Jesus, we've come a long way.
Can't afford a lobby? We've come a long way.
Yeah. Well, that's a great story.
Holden, you joined the firm in 2005. What was it like back then when you joined?
Well, we were in the 32nd floor of the Transamerica, in that way it was similar, so we just couldn't have had that many more. First of all, when I joined, it was called Thoma Cressey Equity Partners. And I went into private equity, to be honest with you, not for any grand thing. I liked finance, I thought investment banking was sort of interesting. And then everybody seemed to want to go into private equity, so I was like, "I should probably go into private equity. It seems smart. It'd be fun to be an investor and learn how to operate these companies." But I did it for two years at Thomas H. Lee Partners in Boston, and they were a generalist firm. And in '99 to '01 when I was there, it was a really, they had a $6 billion fund, a lot of smart guys, great guys there.
Then I went to business school. Then I went to Morgan Stanley Capital Partners in London, which was also a generalist fund. And the way they would do deals as a deal would come in from an investment bank, and then we'd have to clear conflicts with the investment bank. And then you'd try to go find an operating partner to get smart in an industry. Then you would go compete with 15 private equity firms and the deal would take six months, and you probably had a pretty low win rate. And I remember thinking, "This does not feel like the best way to do this." And when I was at Thomas H. Lee, which was a great firm, I mean, we would partner with Bain and Blackstone, and we looked at these consortium deals, tried to take Harcourt private. But you'd be in these rooms with management, and it would be these massive tables with people from Bain, people from Blackstone, people from McKinsey, people from Goldman Sachs, people from Morgan Stanley.
At my level, I remember thinking, "How am I ever going to figure out whether I'm actually a good investor or I'm just another cog in a good wheel, but a wheel?" And so I remember coming out when I came out to the Bay Area, I was like, "I want something different." And I met Orlando, I was still on the headhunter's radar, I met Orlando. And at the time, Thoma Cressey was a $550 million fund and Orlando had done two software deals, neither of which had been realized at the time. So it was very early, but he had a thesis around it. And at the time, software was only 30% to 40% of the investing. We did a lot of healthcare deals out of Chicago. There was something about his intensity and that he had this strategy and he had found Marcel Bernard, this kind of senior operating partner, who's an incredible mentor to all of us in operations.
It just felt different, it felt different. It felt like a place where Carl Thoma had given him all the rope he needed to either be successful or not, and it felt like he was going to give the same opportunity. So it took me a while to be convinced because he was really... I mean, he comes on, he's intense. You know how he is. He's so into this. And I think his impression of me was probably, I'm almost thinking there's some analogs between you and me because he's like, "Oh, he's calm, he's thoughtful." So I remember our last meeting with him, I could tell by this point, I had decided I wanted to do it and that took a bit. But I could tell he was still wondering if I was... I'd been working at these more pedigreed larger firms with more bureaucracy and was I going to get on the phone and just start cold calling people and going to trade shows and doing all these things that he really espoused?
So I remember telling him, I'm like, "If you're worried that I'm going to sit around and just look for things, just not show you the entrepreneurial spirit that you're looking for, if you're worried about that, you can take those fears away. I'm going to work extremely hard. This is what I want to do." And I remember the next day I got an offer and that's when I joined. So Seth started the same day that I did and we basically had two teams doing software. It was Seth and Winnie Quan, and it was myself and Tre Sayle, were our two teams, and there was Orlando and Scott. And Seth, because he came from Summit, knew all the software companies. I mean, I'd been at Thomas H. Lee and Morgan Stanley Capital. I mean, I'd done one or two tech things, but I didn't really know any of the software companies.
So he immediately hoarded all, he put all the names in the database with his initials next to them, so I was already getting crowded out. It was kind of funny back then, we didn't have much structure. We had a strategy. And I remember Seth and I, sometimes we'd go to Orlando and be like, "Orlando, you need to make this fair, divide these lines." And so that's where we ended up doing applications and infrastructure so that we each had enough market and we weren't just colliding into each other every day. But that's where the ride really started. And it was exactly what I wanted, which was, you got to go figure out a space, a name, you got to go meet these people, you have to sell them on doing business with Thoma Bravo. You got to figure out how to price deals.
And when we split from our other team in '08 and '09 and raised a fund on our own that was just software, Seth and I were pretty young. I mean, we were just crossing from VPs to principals. And I remember some of our LPs looked around and were like, "Well, who's going to do deals for you?" And Orlando, they were like, "These two guys, these guys." And so all that responsibility came early, which is exactly what I was looking for. But I'm curious to hear about your evolution because we've really tried hard, as you know, and you're a real leader of our firm now, but we've really tried hard to continue to be kind of nimble and entrepreneurial and not a lot of, you don't have to have a 200 slide PowerPoint deck to go talk to about an investment with a managing partner. We've really tried to maintain that culture of collegiality, but also entrepreneurial culture. So I'm curious about how you see the firm and your evolution here.
Yeah. No, that's such a cool story. And as I just think about continuing to draw that line, I show up in 2014 and I had met everybody as part of the process. I come in and to your point, we're organized really into infrastructure and security and applications. And I remember at one point, A.J., who now runs our Discover Fund, he called me and he was on the road somewhere and he was like, "What do you want to do?" And I'm like, "I just walked in here. I want to do what you guys need me to do. I don't want to..." Although, looking back on it, I probably should have just been like, "I want to work for you." And I think there was-
A.J. was my right-hand guy then.
That's right.
For many years. I mentored him, trained him up and he was amazing. And yes, he was, in '14, he was still active, but he was about to go do the Discover. But not then, not quite yet.
I got to work with A.J. for a couple years.
Right. I remember asking him, yeah, "Which one of these two guys do you want?" And we were waffling, or I can't remember why we couldn't make a call.
Yeah.
Sorry about that.
I'm sure the behind the scenes discussions were hilarious. I'd love to go back and look at the text and email traffic. But as luck would have it, I ended up fortunate enough to be on your team with A.J. and here we are, 12 years later and just kind of looking back on how everything unfolded. I've been so fortunate to have you and have A.J. as a mentor. But coming in as a VP, I think the story you told about how much rope you had and how entrepreneurial the firm was, that's exactly what I walked into whenever, nine years later. And I feel like that's still how we try to operate today. And Carl Thoma, who obviously, one of our co-founders, one of the things that I've heard him say, and I've now heard Orlando say a bunch that I think has really stuck with me as I've kind of gone on my career here, was, "It's okay to make a mistake, but it's not okay to make that same mistake twice."
And it's such a simple but pretty profound statement. And I do feel like that kind of lives inside of our firm everywhere. We throw people into a ton of responsibility early. That's the only way that you can really learn. You're going to make mistakes, they're going to be painful, but they're likely not going to be totally fatal. And what comes out of that in terms of what you learn and how you evolve as a professional, in the different places I've been in, in my career, I've never seen anything like that. I think it's really special. I think we've got to make sure we keep it that way for a long time.
That's really well said. It's so funny because I think that same question, and now it's obviously been answered many times over, you are so good at this. You work so hard and you're so quietly intense and you have so much conviction, but you do have a calm exterior. And so I was like, "Is he going to grind over the price at the last minute," which you do unbelievably well, by the way. And I remember too, when Orlando was out here and he really wanted to start a new product and he was like, "Well, first we thought maybe Tre Sayle," but Tre didn't really want to do it. So he's like, "Well, A.J.'s the only other choice."
And A.J. was my right hand for five years and you walked right into it. You saw by the end, there was probably a little bit of tension. There probably wasn't a lot more I could teach him and we were... But he's so good and he's so ambitious. And I remember I had a drink with Orlando, and over the course of two hours, Orlando is just the master, right? By the end, after my third vodka soda, I was like, "All right, A.J. can go do this." And I remember I woke up the next day and I was like, "Ah." I had total seller's remorse. I'm like, "Dammit."
And he was doing all these things.
Well, how good was it, end up being? But when I went to Orlando, I go, "I don't think I'm ready." And Orlando had already told A.J. And A.J. was already literally white-boarding strategies.
It was done.
He'd already had three deals under LOI. I mean, it was in 10 minutes. So I was like, "Okay." But you were young in career. And I was like, "Okay, I've got to go train." But I remember too, we worked on one of the first deals we worked on, it was you, me and Tre-
Yep.
In between. And I remember after that, frankly, it was a little bit of a clunky setup. And we're very much, one thing we've always espoused, it starts with Marcel and Orlando in my mind, is direct line of sight, accountability. We work in teams, everybody know who they're reporting into. That's kind of our thing. And so that was a bit of a clunky structure for our firm and for you. And I remember being on a plane with you once, and I thought this was pretty cool because Tre had been such a great investor and person and worked with us for so many years, but he was kind of trying to figure out what he was supposed to be doing.
And I remember asking you, I'm like, "Well, do you want to work with both of us or would you rather just work together?" I mean, I had been here a long time and you were new. And you were like, "Let's work together, that's what I want." And similar to A.J.'s evolution, it was just a very quick learning curve. And now I think about it and you've got six exits under your belt. And frankly, I'm glad you allow me to continue working with you because they're similar. I can't teach you much more, but I enjoy it. So it has been quite an arc for you.
Yeah. No, well, I feel the same way. One of my earlier memories, I had just joined the firm, we had gotten sorted out what team I was going to be on and we got our first deal to work on. And it's basically you, A.J. and me. And this company is in Chicago, so we take first trip out somewhere to go have a management meeting and really start to dig in. So we fly out together. And actually, I remember the night before the meeting, there was no dinner or anything, so the three of us went out to dinner and had a great dinner. I realized at that point, I saw it in my interview process, but you guys were just great people, obviously incredible investors, they're really good people, people that I could see myself working with for a long time. Next day, we go to the meeting, it's a great meeting. We ended up having to take a United flight home.
I think back then, VPs, I was in the back of the bus and you and A.J. were up front. And at the time, and it was kind of towards the end of you guys working together, and so I think A.J. wasn't shy in sharing his thoughts in probably a really direct way. And I think you guys have been really going at it about the merits of the deal, whether it was interesting or not. And at this point, back then, there's basically no WIFI in these places. I'm just sitting back there and I'm probably working and trying to figure out what's going on.
So we land, you guys get off the plane first, you wait for me in the terminal. I come out 10 minutes later from the back. It's 10:00. You both have your laptops open in the United Terminal at SFO and you're cranking on stuff and kind of bickering with each other about the deal. And then I come in and A.J.'s just like, "Where have you been?" And I realized, I'm like, "What?" My first question I started to ask myself was, "What did I just get myself into?" But then I realized how special that relationship was that you guys had. And it was such a good moment of, "Wow, this is..." But I just loved how in it you guys were and how you worked together. And I feel like hopefully I've been able to carry that on.
You've more than carried on the form, but it is funny. At that point in our relationship, AJ can get so much done in such a short period of time that it's almost annoying. I'm like, "How does he?" Because I remember with United, you remember they bring out the ice cream and all those great treats in the beginning? And for the first two hours of most of those flights, he would watch a movie. And for some reason, that drove me crazy. I'd always be looking to see if he was... I'm like, "Why isn't he working?"
I learned to always sit behind you at that point.
I used to get annoyed by the weirdest things. I mean, nothing to do with anything. But yeah. Well, Brian, thanks so much for sharing. It's a fun walk down memory lane. Been great to have you on board and thanks for sharing. Thanks for sharing those insights and a little bit of your own personal experience and the history of your arc here at Thoma Bravo. Thank you.
It was super fun. Now we got to get back to work.
Listen to Thoma Bravo's Behind the Deal, season four on Spotify, Apple Podcasts, YouTube, or wherever you get your podcasts.
