AIR DATE:
April 9, 2026
LENGTH:
22:30 Minutes
CARL PRESS (00:00):
It is not uncommon for me to walk by Adam's office late at night when I'm leaving and he's sitting there learning about MCP server or talking to one of our companies, or Sam, you're calling, you know, the CEO of one of our businesses to ask about where we are on the latest agentic capabilities on a product that we know we're launching. Just insatiable curiosity is so critical, I think, in this job.
ORLANDO BRAVO (00:27):
Welcome to Thoma Bravo's Beyond the Deal. I'm Orlando Bravo, founder and managing partner at Thoma Bravo. Last week, we shared a Behind the Deal episode on Exostar, the first investment from our Explore platform. This week, we're using that story as a jumping-off point for a conversation about how our Explore platform launched. Thoma Bravo partner Carl Press, principal Adam Kinalski, and Senior Vice President Sam Yules, come together to reflect on what it was like to build the platform from the ground up as its founding team. They share an inside look at the early days of Explore, how the strategy took shape, and why the platform plays such an important role in the broader Thoma Bravo ecosystem. All right, guys, I'll let you take it from here.
CARL PRESS (01:24):
Hi, and welcome to Thoma Bravo's Beyond the Deal. I'm Carl Press. I'm a partner at the firm. I've been with Thoma Bravo for just about 11 years. Last week on Behind the Deal, we got to talk about Exostar, which was the very first investment in the Explore platform. And so this week, I thought we'd do something a little bit different, and we take a minute to talk about the formation of the Explore platform within TB and how that fits in broadly within the Thoma Bravo ecosystem. And of course, I had to bring two of my very close colleagues and partners with me in the Explore journey, Adam Kinalski and Sam Yules. Guys, why don't you introduce yourselves?
ADAM KINALSKI (02:00):
Yeah, no problem. Hey everyone. Adam Kinalski. I'm a principal at Thoma Bravo, and I've been with the firm for close to 10 years.
SAM YULES (02:05):
And hey, everyone, I'm Sam Yules. I'm a senior vice president here at Thoma Bravo. Been here almost 8 years.
CARL PRESS (02:11):
So Adam, you and I did a Behind the Deal episode where we talked about our very first investment in the Explore Fund, Exostar. And as we were going through it, it got us thinking about the very early days of forming the Explore Platform. And so we thought we'd take a little bit of time to rewind and tell the story of Explore, which is part of a much bigger story of Thoma Bravo and how we've evolved as a firm, how opportunity gets created here, how we've kind of stayed true to our roots in the middle market. And so I want to go back first to 2016. So I joined the firm in 2015. At the time we had one fund. We didn't call it the flagship fund, it was just the fund. And in late 2015, I got a call from Orlando, a very quick call on a Saturday, letting me know that we were going to launch our first new fund product outside of our core.
(03:06):
It was something that A.J. Rohde was going to lead and that he asked me to be A.J.'s number two. And that was Discover. I was fortunate enough to be part of the Discover platform for the first four years. And then in 2019, as Discover was getting big, we decided, let's go do it again. Let's create another platform. And the whole idea, the genesis of both Discover and Explore is as our firm gets bigger and as the funds got bigger, we wanted to stay true to the middle market, which is where Thoma Bravo really cut its teeth in enterprise software, working with what we like to call the emerging category leaders in enterprise software. These are businesses that are a hundred million of ARR or below or in some cases 50 million and below. These are often founder-run businesses. They're deeply ingrained in a particular vertical, founders with deep domain expertise, businesses that we just absolutely love.
(03:57):
We never wanted to get away from that. Discover gave us a vehicle to do that and then eventually Explore. And I was so privileged to be asked to help co-lead this effort in Explore. Maybe start guys, early days, Explore memories when we were first getting going. Adam, I remember the first conversation you and I had about this coming together, but maybe why don't you give your take on it?
ADAM KINALSKI (04:21):
Yeah. Yeah. Happy to. So I distinctly remember it was a morning, I think it was a Thursday morning in July 2019 when I woke up, I think it was about six in the morning, and I'd already received an email from Orlando Bravo that says, "Please swing by my office first thing in the morning."
CARL PRESS (04:38):
Perfect way to wake up.
ADAM KINALSKI (04:39):
Immediately I was like, "Oh God, what did I expense? What did I do wrong? I'm going to have to pack up my things and leave." So I quickly got ready, sprinted to the office and he was already there. I think it was like 7:30 in the morning. And so I went in and he sat me down and he told me about the formation of the Explore Fund and he gave me the full pitch as you described it. He told me that you were tapped to lead it, that I was being asked to kind of be the number two to help you with that and really pitched it like you did as an opportunity for us to go back to where we really developed our operational playbook on how to run a best-in-class enterprise software company, where we thought the most opportunity was for the toolkit that we have.
(05:27):
And so I just remember being super excited for the opportunity. It was also a giant leap in responsibility. I was barely a year into my seat being a senior associate and I was asked to go effectively from number four on the team to number two. And so it was really a sink-or-swim moment for me, but I wanted to do well and I wanted to crush it. And so it was a no-brainer for me to kind of hop on board. And so the next task I had was to find the number three to fill out the three amigos for the fund and—
CARL PRESS (05:57):
Enter Samuels.
ADAM KINALSKI (05:58):
Enter Sam Yules. So I don't know, Sam, if you have any context you want to share on the early Explore Fund days.
SAM YULES (06:05):
Yeah. I remember it being a very exciting time. A lot of change, obviously. I think what's funny is we sort of knew each other walking the halls of the firm, but had very rarely interacted. I think Carl, you and I maybe shared an Uber to a basketball game once, and Adam and I, we were friendly, but I don't think we had ever worked on anything together. And so I remember being so excited about the idea of starting something new with Thoma Bravo, a clean slate, an empty plot of land for us three to go build something incredible on. I mean, it was such an incredible opportunity and I couldn't think of something more exciting to do early in my career. So thank you guys for taking a risk on me, and it's been a fun journey ever since.
CARL PRESS (06:47):
And I remember, Sam, you mentioned this before, is when we first sat down as the three of us to go through a pipeline and talk about, well, what are we going to do? It was as blank slate as sort of blank slate gets. Now, there were some names that had become too small for the Discover Fund. And so we started talking about those. One of those was Exostar and that really was the first deal we ultimately did and of course launched the platform. But maybe switching to the tactical, the pipeline building, the business building, what are your sort of early thoughts on how we attack that?
SAM YULES (07:26):
Yeah. I have a very distinct memory in my brain of opening our folder structure where we save everything, starting a drive called Explore, and there was just nothing on it. So as blank of a slate as you could imagine—
CARL PRESS (07:38):
That has like 50,000 folders now, some folders in it today—
SAM YULES (07:40):
Yeah, yeah, it does.
(07:42):
And I remember thinking, okay, so I came from infrastructure and cybersecurity, you came from apps and you came from Discover. So there's virtually no overlap in our experience. So we were starting from kind of what we knew, right? So I was going through, okay, what were all the add-ons that we looked at in the companies I'd worked with? What were interesting Discover names that maybe had gotten too small for them, but were good fits for our fund and our strategy? And obviously that's how we found Exostar. And then we spent a lot of time getting on the road, which was not something I had done before. I remember, I think in our first week we were in Boston at a conference, we met with maybe 30 companies in two days and Adam and I had the opportunity to pitch Thoma Bravo and pitch a new fund that didn't even really exist yet.
(08:20):
So we were kind of telling people a secret. And it was such a fun opportunity for us to get to bond together, sort of learn, okay, how are we going to market this? And it was such an unfair advantage. I remember going to these meetings and these companies where 20, 30 million of ARR meeting with Thoma Bravo, one of the largest software investment firms globally. And they were so enamored by our brand. And I think it gave us a really big advantage, frankly, because we now were able to really spend time and bring all the resources that Thoma Bravo has into smaller founder-led companies that were really looking for a great partner and we could fill that role.
CARL PRESS (08:53):
Yeah, I remember we used to joke, it wasn't bringing a gun to a knife fight. It was bringing a bazooka to a knife fight. And because we were unencumbered by portfolio operations or really much of a pipeline to start with, we would take every meeting with any CEO that was willing to talk to us at every conference. I remember the early conferences that we went to, you mentioned the Boston one, we ended up flying to London, I remember in January of 2020, that was a very fun trip right before COVID and everything shut down. I remember running through the airport thinking, "If we miss this connection, we're in trouble here." But we had a whole day of meetings lined up in London that ended up being highly productive. And so just all the trips. Adam and I went to Israel together, right? We were there. It was a fun. Fun trip. Spent time with a bunch of Israeli CEOs talking TB, talking Explore.
(09:40):
And so I think you're hitting the nail on the head, which is we just grinded it out. We went everywhere that we could fly to, meet with CEOs and go build the brand and talk up TB and Explore and evangelize and source. We did no banked deals in the first two years. It was all proprietary stuff. And to pull off a proprietary deal is an incredible feat. And you guys were leading the charge on that. And so it was really fun to watch you guys develop that skill, which I think Adam, you mentioned, we had to evolve that sales skill, right? Like it is selling, it's selling Thoma Bravo, it's selling ourselves, it's selling a vision for what the platform can offer. And you guys have both evolved into true sales people as you do your jobs as investors. I think that's why we've been able to have so much success with proprietary deals.
ADAM KINALSKI (10:27):
Yeah. Yeah. So for me, I had no idea what kind of impact that would have when we officially closed Exostar. So it took us from signing the LOI until closing almost a full year, basically 11 and a half months to get that deal. And people kept reaching out to us because our banker kept saying, "Hey, we are so excited about your first deal." And when we finally closed, people got really excited and money flowed in and we were just off to the races. I mean, I remember within the next 30 days we had made another proprietary offer and we bought a company called Clari 5, which worked really well. And so I loved how it all came together and how we tried out the strategy. And once it was, I think, vetted and we found deal flow and product market fit if you will. Me, I just felt super fortunate that I got to be to be at the ground floor of forming this platform so I could learn what it really takes to start and run a business, while still having the luxury of the Thoma Bravo brand and ecosystem around us.
CARL PRESS (11:25):
Yeah, I think there's two or three questions that I get asked the most. And so we'd be remiss of us to not address them here. One is, what is your day-to-day look like? How do you split your time? Second question is, how does all this fit together at Thoma Bravo? The different teams and the different platforms. And the third is, what makes a great investor at Thoma Bravo? And so I kind of want to hit them all if we've got time. So let's tackle the first one. Day-to-day, how does it work? What percentage of time are you spending on sourcing versus executing versus operating?
SAM YULES (11:56):
Yeah. For me, I'd say it's a big bulk of my time right now, at least, it's going be sourcing, right? So I'm either on the phone or I'm on Zoom with potential corporate development contacts, bankers, CEOs, working on relationships, working on ideas together. And I'm just grinding and so that takes probably 50, 60% of my time. And then when I'm in a live execution, it takes up the rest of my time. So you're just in investment committee or you're on diligence calls or you're doing analyses to figure out how to transform a business or you're sitting down with a CEO and helping them understand what Thoma Bravo does and how we can be helpful. And then we don't spend a ton of time on portfolio monitoring because we have such an incredible team called Operating Group led by Richard Tartak. And they have folks embedded in each of our businesses oftentimes many folks. And so we get the support of folks that are helping operationalize improvements or reporting information or strategic initiatives. So we get to sort of stay closer to the strategy level, stay creative, stay sourcing, and they're on the ground fighting a lot of the day-to-day fights for us.
CARL PRESS (12:58):
Yeah. And I remember in the early days, we're like, "Okay, well, which team members are going to go on which boards?" And I think all three of us wanted to do it, but I think we quickly learned that's a three- to four-hour monthly commitment. We really need the time to source and execute on deals and then manage a business and it works. I mean, I always joke it's on the one hand, the hardest job that I can imagine and most fun and most rewarding. On the other hand, there are days where I'm like, this is amazing. And so in a lot of respects, we've evolved so much as a group. We've grown, we completely deployed our first fund, we then raised the second fund, which is almost twice the size as the first fund, but the work, the sourcing, the activity, it feels like it hasn't changed, which is kind of special and unique and it's exciting. I like it.
ADAM KINALSKI (13:54):
Yeah. I think one thing I learned about our fund and what makes us special is that part of our job is really sales and relationship building. And so we spend a lot of time being on the road, developing relationships. A lot of these companies are bought, not sold. So you need to really put in the time and effort to make sure that you're going to be a good steward because a lot of these businesses we're looking at are founder-owned businesses that take years to decide on a partner, not a process through a banker. And so that's something I think we've done a good job of is developing and cultivating those relationships.
SAM YULES (14:28):
Yeah. And that's what really helps to be a part of Thoma Bravo because we have all of that history of other teams that have sort of built some of those relationships for us that we can inherit, enrich, grow, and so it helped us get a fast start to our franchise.
CARL PRESS (14:42):
One thing I give so much credit to Orlando and the managing partners on is we never felt, and I think this was true of Discover too in the early days, we never felt like the little brother or the stepchild or less important. I always tell CEOs and bankers and anyone who will listen that if you just look through the conference room window into a meeting, you wouldn't know if it's Flagship presenting or Discover or Explore. The audience size isn't any different, the attention that we're getting, the scrutiny that an investment is getting is no different, and I'm eternally grateful and appreciative of the managing partners setting it up that way, because it really makes us feel like we're another team in a much broader constellation of teams at Thoma Bravo. There's Explore, there's Discover, there's Flagship applications, Flagship security, infrastructure, and so forth, and I just think that that setup has served us so well.
SAM YULES (15:37):
Yeah, totally. It really helps that we all do the same thing too, and we're all focused on the same types of companies, the same metrics, so it's all very transferable in terms of, okay, what makes a great Explore deal probably makes a great Flagship deal. It's just a different size. So it's very extensible for everyone as well.
ADAM KINALSKI (15:51):
Exostar, Carl Thoma, founder of our firm, joined for several meetings, diligence meetings, served on the board of Exostar, and this was a sub-$100 million equity check deal. So just goes to show the level of attention that we get.
CARL PRESS (16:06):
Yeah. I don't think there's ever been a meeting where we've asked Carl or Orlando to join us, fly out, make a phone call on our behalf and they haven't. I mean, pick up the phone immediately and do it for us, which is obviously, again, it's wielding a bazooka in the knife fight. It works 100% of the time.
(16:25):
One of the things that I think has remained true throughout our journey in Explore and was certainly true in the early days of Discover is if we're going to win, we have to be creative and we have to be more creative than our competitors. And I think that's one thing that we particularly pride ourselves on is not just sitting back and letting deals come to us. We get out on the road, we pick up the phone, we get on Zoom, and we're very proactive on sourcing. I think that served us extremely well. Sometimes we step into stuff that's a little too creative and then we've got to walk that back and reel back, yeah, but that's okay. And I'm particularly proud of how you guys have spearheaded that sourcing initiative within our group and now have kind of imbued that philosophy across our junior team and throughout the entire team.
ADAM KINALSKI (17:15):
Yeah. Yeah. I would say we like to, and credit to you for kind of imbuing this sense in us, but we like to really dig into the quote-unquote dirty stuff or find deals that are perhaps a little bit contrarian and you need to squint or you need to really do the work because the data is really bad. And if the data's really bad, you already eliminated 85% of the competition because they don't want to do the work to get under it just to see if there's a deal or not.
CARL PRESS (17:43):
Have we done a deal with good data, by the way? I—
ADAM KINALSKI (17:45):
I think it's a criteria that the data is bad in order for us to do it.
CARL PRESS (17:49):
It's a necessary condition. Yeah.
ADAM KINALSKI (17:50):
But Exostar is an example, right? On the surface, if you just look at the high-level P&L, it was burning money, it wasn't growing all that much and the data was extremely hard to manipulate. It was very hard to get a sense for retention, revenue quality, and so I think Sam and I spent maybe a cumulative hundred hours over the phone with the CFO, the head of finance, our accountants and just literally going line by line with, I think it was like a hundred thousand rows of different customers, different revenue lines, revenue swings, credit memos that we had to adjust out. And once we did all that work, we found out, holy, holy cow, this is like a 95% gross retention business. If you took a first pass at it, you would probably think it's in the high 80s, low 90s. We knew that fundamentally, the business model made sense that this should be a really high-quality business. The numbers didn't seem to tell that story. And so we really had to do the work and dig in to kind of uncover that story.
SAM YULES (18:47):
Yeah. I just remember thinking, are all the deals going to be this hard? Because if so, this is going to be a really hard job. But no, yeah, you said it really well, Adam. I think I credit you and the mentorship you gave me to sort of get through that because like we were talking about earlier, we had never done it before, right? Everything we were doing was new. Everything we were doing was sort of setting the precedent for the next deal. And we still leverage materials, analysis, thoughts from our very first deal on stuff we work on now. Obviously we've gotten a lot better and faster and even more creative in some circumstances, but I totally agree. I mean, so many of our best deals are companies that were not for sale, did not have bankers involved, did not have a legitimate ERP system for us to pull information from.
(19:29):
So oftentimes we're building the analyses ourselves and that takes patience, that takes hard work, that takes a lot of help from our advisors, but I credit you and the direction you've set us on of finding the right companies and the right setups, the right markets where we're confident we're going to find the right answer. We just have to do the work. And I think it's led to some really good investments.
CARL PRESS (19:49):
Yeah. I'd say another theme at Thoma Bravo is we're never satisfied. We never sit still. Just when we feel like we've got this software thing figured out, we got it licked pretty good, the world changes and then it changes again and then we have to relearn everything. And I think the two of you guys and our whole team, we share the same ethos as our broader firm and Orlando and the managing partners set this tone, insatiable curiosity and understanding what's next, what's coming for our businesses. Of course, right now it's AI and it is not uncommon for me to walk by Adam's office late at night when I'm leaving and he's sitting there learning about MCP server or talking to one of our companies or Sam, you're calling the CEO of one of our businesses to ask about where we are on the latest agentic capabilities on a product that we know we're launching.
(20:37):
Just insatiable curiosity is so critical I think in this job because things are always changing. We have such fierce competition and we have to stay ahead of what's happening in our industry.
ADAM KINALSKI (20:50):
Yeah, 100%.
SAM YULES (20:52):
Yeah. And we only have 14 people on our team trying to deploy all this capital, right? So every person really needs to be creative, needs to be thinking about what sectors am I interested in? What sort of niches or categories do I want to go explore? And I think we all set the tone of, "Hey, feel free to do that." There's no constraints on how you should be spending your time as it comes to origination, finding new companies. I'm so proud of our associates when they find a really interesting off-the-run company that looks like a great opportunity for us because that's how this firm was built, that's how this fund was built, and that will continue to be our strategy.
CARL PRESS (21:24):
And that's where the best ideas typically come from anyways. 100%. Well, guys, I'm so glad we got to do this. I always joke that I feel like I have the best seat at Thoma Bravo and it's not just because I get to
(21:37):
work in the middle market, which is exciting and dynamic, but really get to work with the two of you and our whole team. And it's been an absolute joy to be able to build this business within a business and to be able to do it with you guys who are really two rising stars amongst many at our firm, across all the different teams that will end up being senior leaders of your own. So thank you guys for the friendship, for putting up with me when I didn't know anything, really appreciate all the support and partnership. And I'm pumped to keep doing this for a long time. I think this is just the only the beginning.
ADAM KINALSKI (22:10):
100%. Thanks so much. Yeah, it's been a fun ride. Yeah.
CARL PRESS (22:13):
Let's go.
ADAM KINALSKI (22:14):
Let's do another podcast soon.
ORLANDO BRAVO (22:19):
Listen to Thoma Bravo's Beyond the Deal, season four on Spotify, Apple Podcasts, YouTube, or wherever you get your podcasts.
