Like, I was thrilled. I hope I tried to contain my excitement a little bit because we still had some details to work out, but I couldn't have been more thrilled. And one of the things that I recall that helped get me excited was the depth of understanding that Toma Bravo had you, in particular, chipped with the technology space we were in and the competition and the opportunity.

That excitement that you showed Seth and I that morning was absolutely necessary because a lot of people thought we were crazy to want to embark on this mission.

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Welcome to Toma Bravo's behind the deal. I'm Toma Bravo founder and managing partner, Orlando Bravo, and that was John van Sicklin, the former CEO of Dynatrace, speaking with Toma Bravo partner Chip Burning. The Dynatrace deal was one of the most intricate deals we've ever pulled off at Toma Bravo. It involved a complex carve out, a take private, a subsequent IPO, and a million square foot building that we needed to sell. But despite all the moving parts, Tomo Bravo partner and deal lead Chip Bernig never gave up. He really understood how valuable Dynatrace could become. Ultimately, he was right, and our firm was rewarded with one of the best investments we have ever made. Years before, it was common knowledge in the business community, we at Toma Bravo saw the massive disruption cloud infrastructure was going to have on SaaS and the tech sector as a whole. In searching for a partner that could help us take advantage of this coming change, and that was aligned with our values, we found a company in Austria called Dynatrace. We were impressed by their culture, their products, and their founder and CTO burned Grayfinator. But unfortunately, before we could make a move, they were acquired by another company.

Later, through a complex carve out that leaned heavily on the unique skills of the Toma Bravo team, we got our hands on Dynatrace and gained an opportunity to work with its general manager, John van Sicklin. John has a career in enterprise software that dates back to the. As we said to him, we were betting on him and his leadership as a full partner in this deal. John rewarded our faith and then some. And in 2019, Dynatrace had one of the most successful ipos we've ever had here at Toma Bravo, one that ended with the team behind the deal ringing the opening bell at the New York Stock Exchange. Today, Dynatrace has a market cap of over 16 billion. There are three key points that I take from the Dynatrace case study. First is the investment judgment required to buy a very special company. And that wasn't obvious. The company was buried within compuware and went largely unnoticed. Second is how one could achieve high margins and high growth at the same time that they go hand in hand. And third, investments for Toma Bravo are not linear. And Dynatrace was certainly not linear. About a year after the investment, things were not great.

But our team stayed focused on how we operate and supported existing management. The Dynatrace deal employed a multitude of operating levers that we have to pull at Tomo Bravo. Building value, carve outs, a merger with another portfolio company, operational improvements on day one, backing existing management, and transforming the business to a SaaS based model. As I said, it certainly wasn't easy, but it was exciting to see it all come together in a single deal. And it's a great example of what an IPo can look like. So today, you'll hear everything that went on behind the deal of this investment from Chip Vernog, the deal lead and partner at Toma Bravo, followed by his conversation with former Dynatrace CEO John van Sicklin.

Hi, I'm Chip Vernig, a partner at Toma Bravo, and I've been with the firm for 15 years now, focusing on our infrastructure and cybersecurity investment efforts. Diatrace is a leading provider of modern cloud infrastructure and application observability solutions. And why is this important? Well, companies across every industry are increasingly relying upon technology to accelerate the way they do business, the way they interact with their customers, their employees, and their partners. And this movement is broadly referred to in the industry as digital transformation. I think it was Mark Andreessen, a very well known VC, who first coined this term by famously saying in 2011, software is eating the world. So that is really where the thesis of diatrace originated from. It was really our efforts to capitalize on this thesis of digital transformations. And our view was, if this world is going to be run on software, and we are going into a digital world and a digital economy, who is going to ensure that this world functions and everything runs well? And that really was the thesis of dietrace. Dietrace's mission statement is to make software run perfectly. So back in 2012 was when we were chasing this thesis down, and we quickly moved on to try to then figure out what investment could we make that would be the ultimate play on this thesis around enabling digital transformations and ensuring these digital transformations run perfectly.

And we did extensive market work back in 2012, and that's when we landed on diatrace as being the ideal company for us to invest in on this strategy. Unfortunately, Diatrace had been acquired right around the same time that we were coming into this thesis by a large, publicly traded, tech diversified holding company called Compuware. So we quickly realized it was going to be very hard to convince a large, sophisticated public company to sell us something that they just acquired, despite how much we liked it. Now, at the same time, we got lucky, because compuware, as a large public company, was struggling on its own. The diatrace business they acquired was just one small piece of a small piece of a big amalgamation of assets that they have acquired over decades and decades of being a public company. Specifically, an activist investor got involved in their stock around the same time period. And that is when we decided to hang around the hoop, because typically, when things like that happen, we thought the business could be sold outright, pieces of the business could be available. And we were really keen on trying to figure out how we could land on diatrace.

While we were waiting and getting smarter and trying to get an opportunity to look at compuware, we continued to do our market work and actually ended up making an investment in a smaller player in this market known as keynote systems. And that was our first kind of effort and our first investment in this observability market. And having owned keynote for a little while, we quickly realized that it was a great market to be in. But keynote didn't have all the pieces, and it made us want dynatrace even more. The activist effort at Confiware was continuing at this time, and they ended up selling four business units to various firms, which simplified the story, from our view, significantly. Confeware was a holding company that had six business units. Now it just had two. And the two remaining business units were a mainframe business that focused on development tools in the mainframe environment that had been around for a long time, a very mature business that was, sadly, at the time, declining about 35% per year, and nobody wanted to touch it. And then the other asset was their APM business unit, which referred to application performance monitoring.

And within that APM business unit was Dietrace, which was the crown jewel of this whole company, and what got us all started. So we quickly realized that having had four businesses already spun off of compuware, two remaining. If they sold the mainframe business to somebody and really simplified this, it would be very competitive to get our hands on diatrace. So we decided to bite the bullet and buy the entire company. So that's how the deal came together. We bought the company in 2014 for $2.4 billion. There was absolutely zero competition on that. Take private from our perspective, because nobody wanted to deal with the overhang of the declining mainframe business. They didn't want to deal with all of the other general administrative and shared services expenses that we had to inherit. That once supported six businesses in total. And as I mentioned, four were sold, as well as a 1 million square foot building that they wholly owned in Detroit. So no one wanted to deal with it but us. But we were now the proud owners of compuware. We had that $250,000,000 revenue mainframe business that was falling off a cliff. A GNA.org structure and shared services center of $200 million of annual expense that supported those six business units, and then a gigantic building that we didn't need.

And we finally got our hands on Dietrace. Now, what we did next, I'm pretty confident that I could say that not many other people could pull off. And we first sold the building to a prominent investor in the area for over $100 million. We got rid of all of that shared service, General administrative, 200 million dollar annual expense base that once supported this larger conglomerate, got rid of all that expenses. We then carved out the mainframe business and brought in a very seasoned operator by the name of Chris O'Malley to run that business as CEO. We stabilized that business and actually got it to grow 5% per year for our entire investment hold period from a 35% annual decline the five years prior to our involvement. It actually led to a great exit where we sold that business to BMC, and then we carved out that APM business unit. We promoted the general manager, John van Sickland, to be the CEO of that company. And we backed his existing team from the dynatrace business to merge that entire business unit with our existing portfolio company. Keynote. And we rebranded that entire combined company as diatrace.

People look at diatrace today and see this massive, highly profitable, very disruptive, cloud modern vendor growing very fast. But it wasn't always that situation. It wasn't always that pretty. When we carved out the business, we had to create entirely new systems. We luckily had the core folks in the management team, John van Sickland and Bern Greifinar. And their team. But we had to build an entire new back office system, all new reporting systems, stand up, a GNA structure, legal, build a new sales department, and all that took time. And we also had, at the same time, had to cut a lot of cost that was stranded, that came with all these different assets. The company, when we carved it out, was really 400 million of revenue. Only about 200 million of that was recurring through maintenance contracts growing mid single digits, with some product lines growing really fast. Mainly the core dynatrace product, which was just one piece of the overall APM observability business. But it was making no money. It was literally break even. So we had 400 million of revenue making no money, and that was a non starter for us. We had to prepare the business for profitable growth.

And the first year we spent building all the back office systems, building out the rest of the management team with a mandate to get the profitability up to $100 million of EBITDA in the first year, which took a lot of work, because we also had to make sure we simultaneously were prioritizing our investments in our next generation cloud product, which we'll talk about shortly. And we accomplished 100 million of EBITDA. From there, we really focused on a plan for profitable growth, while also investing in the future. We knew that this market was taking off, but it was actually moving even faster than we thought to the cloud. So as these large enterprises were moving quicker to the cloud, they were increasingly writing and building applications in more modern environments that were more cloud friendly, and that made some of our classic observability solutions obsolete. Diatrace was incredible at handling the most complicated environments with the most scalability, finding the root cause as to why an application or a piece of software wasn't running perfectly. But Dynatrace wasn't equipped to monitor and observe all of these workloads in modern cloud environments and modern programming languages. And we just couldn't anticipate the market moving as quickly as it did now.

Luckily, we had a strategy, and we were shown this strategy during diligence with this next gen offering that they were building behind the scenes at diatrace. But it couldn't come out fast enough, and we felt like it was behind when we first launched it. The intent was to go after small, medium sized businesses, which was not really core to Diatrace's dna. They were always known to go after larger enterprises. So instead of going after the small, medium sized businesses and changing our market segmentation, we intentionally, as a board, told management to go back into the Batcave, quote, unquote, and not come out with this new product until it was indeed enterprise ready again. We carved this thing out in 2014, took about a year to really create the standalone entity. 2015 got to 100 million of EBITDA, growing, but not growing very quickly, and then told everyone we had to build this next gen offering and make it enterprise grade. And then 2016 happened. And I'll never forget, we were in the holiday season of 2016 and we landed our first customer, our first enterprise customer on the new platform. And they came in as an eight figure deal.

And from that point on, it was just nuts. The velocity of new deals, the velocity of hiring new reps, the positive reviews from the analyst community, customers landing using the product, immediately coming back to us wanting more. It was just amazing. And it was amazing to see such a disruptive transition to a company. And it was entirely due to the management team and to burnd, having invented this market in the first place, sold to Compuware, carved out to us. And then he and John van Sicklin disrupted themselves yet again by introducing a whole new platform to leapfrog the market and with the intent to transition all of our existing revenue and all of our existing customers to this new platform, which would take a lot of work. This is where our skill set really came in and our board to really help them manage through the complexities of that transition. It's one thing to sell a new customer a new product. It's another thing to convert all of your $400 million of revenue to this new product over time and over a few years, we got that done and eventually decided, based on the profitability of the company, the growth, having almost all of the revenue and customers on our new platform, that it was time to go public.

And in 2019, we went to New York, we rang the bell, and it was a moment I'll never forget. We ended up going public at around a four and a half billion dollar valuation. And today, you fast forward a few years later, and I think the market cap today is around 15 billion. And I think the company is over $1.25 billion of cloud ARR, which is just amazing to think about, because when we got involved, it was zero of Cloud ARR. So it's just been an amazing story to be a part of. It's a case study that we never get tired of talking about. Not only was it one of our most successful investments at Toma Bravo, but it really, as a case study, exemplifies every single thing we have done with the company that we've done with investment, we just happened to do everything to the same company, and it was just a huge success for us. And it's been very inspiring and fun to be a part of. And now we're going to bring in former CEO of Dietrace and close friend John van Sicklin.

How are you, Chip?

I'm doing all right. Retirement's looking pretty good on you.

It's not bad. I enjoy it.

You deserve it.

Glad you're holding down the fort. Making sure the economy continues to move.

Forward one deal at a time. We've been talking about a case study and finally talking to the world about this story, so I am very excited to be doing this with you today.

That's great. No, same from my perspective as well. The Toma Bravo years, where they were special, to finally get unleashed from where we were hidden and sort of buried at a 40 year old holding company. I've been in the industry for 43 years and it never ceased to amaze me how it would reinvent itself every five to ten years. I remember the early stages of my career being with companies that were extremely successful and all of a sudden hit a wall when there was a technology shift. And so I think prior to Dynatrace, the longest I had been with a company is probably six, maybe six and a half years. But Dynatrace was different, and it was different because the technology continued to evolve and the technology team was able to reinvent itself over and over again and catch the new waves of technology every step of the way. It was really quite amazing, which was the reason I stayed with it for 13 and a half years. It was like multiple lives and multiple adventures into new and exploding markets. Some of the streams were the same, the CTO and founder was the same, the market in general was the same, just an evolution of it, but just amazing how many pivots and shifts were required in order to continue to build a multibillion dollar business in the category we were in.

So, John, in 2008, you had already been a successful CEO. What made you take the diatrace CEO job?

What made me take the diatrace CEO job was meeting and then interacting in a workshop with then founder CTO and CEO Byrne Greyfinator. Now, Byrne started and founded the company in Linz, Austria. One of my first things over breakfast as I was talking to him was, gee, even if this doesn't work out, I'm going to get a trip to Linz, Austria. So that'd be fun. But it was a really interesting sort of feeling out of each other a little bit. I'm not a founder type. I need to see a technology actually be acquired and used by customers before I can really figure out how valuable it is, how special it is, and whether we can take this from the first several dozen customers to thousands of customers. Once I get the hang of it, I'm pretty darn good at it. And that's really been my serial entrepreneurial career is high growth moments in companies. So I was trying to figure out whether this CTO was able to productize things well enough that we could really go from several dozen customers to thousands. Now, burnd, on the other hand, had just been interviewing dozens of ceos who he thought were just empty suits, as I think he told me over breakfast.

And he wanted somebody of substance who didn't just talk a lot, but actually could roll up their sleeves and really understand the business. And one of the things that is unique about Byrne is he's not just an unbelievable technology genius, he's actually quite an astute businessman as well. So anyway, we had a workshop, a two day workshop in Linz, Austria, and we solved some problems that he had from a business standpoint. And he convinced me he wasn't a CTO type that was going to try to hang on to the CEO role, that he really wanted a partner in the journey. And we hit it off. And from there, I knew this was going to be something special. We're both still making sure that we both were staying on the same page and good partners throughout. But I got to tell you, he was just a wonderful person to work with. And together, I think we brought the best out of each other.

John, I know we had lots of stops and starts to the deal, like any deal. But for me, when I think about when we really came to an agreement on what we're going to build together, I think about the breakfast where me and my managing partner, Seth Borrow, flew out to Boston to meet with you and really align on the deal. And I think it was at that breakfast when we told you with complete transparency, what we wanted to create. I think we walked you through our thesis. I'd love for you to tell me if that's what you recall as being the pivotal point in the move forward for you as well.

I couldn't have been more excited because where I was as a general manager, when a technology holding company that was quite distracted with a hostile takeover, I felt like we were trying to build a business in a competitive market space, no matter how good the tech was and how great the market was. But we had one arm tied behind our back, maybe both of them. And when Chip Yu and Seth Borough explained what you wanted to do, which was truly and aggressively carve out the business and stand it up as a separate growth entity, I couldn't have been more excited. It's what I was trying to do inside of compuware, but without a lot of luck. And I knew at that moment that I would spend, instead of spending 80% of my time internally with politics and communication and all the rigamarole of being a division, one of several divisions in this holding company, that I'd be able to spend 80% of my time out building a great business. I hope I tried to contain my excitement a little bit because we still had some details to work out, but I couldn't have been more thrilled.

And one of the things that I recall that helped get me excited was the depth of understanding that Toma Bravo had you, in particular, chip, with the technology space we were in and the competition and the opportunity. I remember talking about apps eating the world as a core thesis of yours, which was the same one we had. So that's a medial alignment. And then from a carve out standpoint, you guys really understood probably more than I did, even about how much viscosity I was wading through and what could be done on the other side with a little bit of freedom. But that alignment and your entrepreneurialism throughout that process of being excited about it, this carve out and what it could be was just phenomenal.

That excitement that you showed Seth and I that morning was absolutely necessary because a lot of people thought we were crazy to want to embark on this mission and take compuware private, carve out the APM business unit, merge it with our pre existing keynote entity, rebrand the whole thing as dynatrace, you as the CEO, hire a team around you, stand up the copywriter or mainframe assets as a separate business, sell the building. This was unnecessarily complex, and nobody really wanted to do it. But we needed that excitement from you, because that's our business, is working with passionate leaders, working with existing management with you, and burned as a combo. If you weren't excited and. Or if burned, opted out, I don't know if we'd be where we are today and if Diane Trace would exist. Because we needed to show our investment committee and ourselves, Seth and I, that we had that buy in and that breakfast and that relationship, and that transparency was so critical for us to get this thing started.

I got to believe there were plenty of hurdles. It clearly wasn't a straightforward deal or sort of line to success. The passion you guys had was clear to me. And I remember something else from that breakfast chip, which was your and Seth's directness about betting on the CEO in particular, and then the extended management team that the CEO would build together with Toma Bravo. That was something that was special to Toma Bravo and meant a lot to Toma Bravo. And so I was partly flattered, but also it's really important to hear, because there's all these thoughts about private equity that run throughout the marketplace as if it's going to just cut and burn everything. You're not going to have any value left and you're going to sell it because of profitability, but not because of value and growth, which is required in a tech company. Once we were aligned there and you said you bet on the CEO, I thought, here we go, let's do it.

And that's a good transition point, John. So we got the deal signed right around that time, and then we weren't without some hurdles along the way. How do you look at the investment from your perspective and the journey from there onward?

Gosh, I remember maybe two or three moments when that journey, the first one was just, oh, and by the way, we need you to cut 25% of your cost. It's on a pro forma basis, don't worry. But 25% of your cost in the first twelve months. And I figured for freedom, that was a low price. We jumped in. We got to 20% in the first year. We ended up past 25 in the second year. But that seemed daunting at the time. In hindsight, I realized that a lot of our ability to do it was, nothing hurt the company. It just made us stronger, it made us lean. But in being lean, you're healthier, you can move faster, you're more nimble. You know where everything is. You can move. And my hats off to the operating partnership that you guys brought on to join the board and the team, because they were invaluable in helping us carve out, reset, restructure, and regain momentum as a separate business. I remember those first couple of years of being quite a challenge to stand up, but if we hadn't done that, we never would have had the success and the next pivot, which was needed.

Yeah, let's go there. The next pivot, because you got your baseline, we had the carve out, we helped you build your structure, get the profitability so you can sustain yourself as a standalone entity. And then the next big step to the journey I believe was the move to the cloud. And I'd love for you to walk us through that whole journey and transition.

Yeah, that was a good test, wasn't it, between the management team and Toma Bravo? So we had actually started on this cloud journey prior to the acquisition, and so we had the skunkworks that quickly gained momentum post the Tomo Bravo spinout, where I think we ended up having maybe a third of our engineering team on this reinvention around cloud. And I remember when the tech team came to me and said, okay, we've done our research. Let's have a dinner and we'll tell you all about it. And they said, you know what? We've decided, looking at everything that's going on and the trajectory in the market, development trends and the rest, the cloud platforms, that we're basically going to have to reinvent everything. And here's why. And they convinced me in a couple of days it didn't mean that we did it overnight. There was a lot of transition work. Took four years, maybe five, to actually do it all. But it was a year into the Toma Bravo take private. Once everything was profitable, things okay, we got our foundation that let's review the product set, and let's review how you're allocating resources. And when the Tomo Bravo team found a third of the engineers on something that was driving zero revenue, I remember some of those conversations, and it did take us a little time to work through it.

It took some due diligence with Byrne and his team, but to Toma Bravo's credit chip, to you and Seth, one of the operating partners, they ended up, after several weeks of due diligence, saying, sounds great. Carry on. And I remember such a relief of that, because internally we knew it was right. But it is a tough pill to swallow, being part of a private equity carve out to all of a sudden realize that the zero dollar thing we were going to bet on as the big thing over the next four or five years. How'd you think about it?

Yeah, I remember all those conversations and all those discoveries and burned and yourself including you were comfortable disrupting yourself, disrupting your own company in order to disrupt the market and jump in front of the competition. And I remember these difficult discussions and these pivotal moments, and we wouldn't have felt comfortable if it wasn't for the consistent leadership and backing the existing team and someone like burn, who invented the market in the first place, and then somebody that he's worked closely with as you, with great commercial expertise on the go to market to make it a success. So once we realized that we had the business set up in a profitable manner, and we could fund this former Skunkworks project into our next gen enterprise cloud solution, we trusted you. And then there were some proof points along the way. I'd like to hear from you, given you had inside scoop. I was seeing everything, and after thought, but what was it for you that gave you confidence and conviction that it was going to work? Because for a while, we were a flattish business. We were profitable. We had this great new tech, but we didn't really have numbers to show for it.

I know it was frustrating for all of us, and we were a little bit worried.

It's a good question, Chip. When we had set up the skunkworks, the concept was not just to go after the enterprise market space, but also down market. And so that's a big space. And I remember one of the operating partners talking about it like, you got to think about it this way. Water through a very wide channel goes very slow, but the minute you start to confine it, it goes really fast. So it's not a bad thing to confine your market angle. So what's wrong with the global 10,000? It's what you're best at. Anyway. So that was an early aha. We took that on board 110%. We shifted the engineering to build out the enterprise capabilities, accelerate them beyond some of the other things we had on the list. We just jettisoned low end, automatic cloud setup and et cetera, et cetera. We had a services team. They could do all that. And that really changed our ability. That ability to focus accelerated a number of things, and I think it culminated in a really large deal at the end of that first year, a seven figure to eight figure deal, largest in the company's history.

And it was all on the new platform.

I remember that moment, and as number oriented individuals, Seth and I were mostly focused on that deal when that thing came in, and it was eight figures, I'll never forget it. In the holidays of 2016, your CRO, Steve Pace, was texting us that. I think I landed a big one. And we're like, on what product? And then he told us the acronym at the time of our next gen product, and we had zero revenue to show for that product prior to this customer. And Seth and I are like, oh, my God, they did it. And from there, it was just like the confidence just went across the entire field organization, and it was one deal after another. And then I guess that leads to the next big milestone. John, which is we got a lot of our revenue tied to this new product very quickly. It was a crazy flywheel for us. In just a few years it was.

And there was another piece of the puzzle that was another defining moment, I think. And that was, it didn't go right along with it at the time. It was actually offset by, I don't know, six to twelve months. And that was a shift in the licensing model away from the classic perpetual licensing with maintenance to a modern, predictable subscription. But those two moments were the ones that really unleashed the opportunity to not just have a highly profitable, solid growth company that we might be able to sell to a strategic, but actually a business that could be an IPO candidate. And not just an IPO candidate, but a leading, high growth, super exciting public company at the time. And that's what we leaned into next, and together we were able to pull it off.

Yeah. And that transition, just to give everybody some context, when we carved out dinetrace, it was roughly 400 million of revenue. And as you mentioned, you got the profitability up to 100 million of EBITDA in the pretty close to after close. But that 400 was roughly flat. And it was almost entirely what we called our classic on prem products, our old pricing model, zero cloud. And it was flattening out. And that 400 million at the time of our prospectus, when we went public, that classics was almost down to zero. And the billion plus that became as a public company of ARR was entirely on that new cloud platform. You basically took 400 to zero while building the zero all the way up to a billion plus, which I don't think there's been a more successful SaaS transition from a carve out that I can see at scale, and it's certainly taught us a lot.

Now, I appreciate that, because I remember at the time feeling, why can't we grow a little bit faster? And we just had too many declining revenue streams. We just had to wait long enough for that new platform to eclipse that 400 million mark. And the beauty of the new platform, which allowed us to really pull this off, was it truly was a platform with monetizable modules. So what we did in product lines before that, these classic product lines, we reinvented them all as modules on this new cloud first multitenant platform, and really surprised the market. Our competition, we still couldn't believe that we had really done this. And in fact, it was probably one of my biggest challenges in those first few months prior to IPO, as well as the next year, was convincing the market that, no, this truly is a reinvention. And what's going on under the hood is truly a high growth, modern software business that is a multi billion dollar winner.

You not only disrupted yourself, you disrupted our model at Toma Bravo in a positive way by enlightening us on how to successfully navigate these very complicated SaaS and next gen transitions that, as you mentioned, this ever evolving industry that is technology, you're constantly disrupting yourself to stay ahead of the competition. And we got the confidence on how to implement that and operate that effectively with our experience with you and your team. And that's led to so much of our success as a firm since that journey with diatrace. So we're forever thankful for that experience. Not just the amazing financial outcome that we generated together in diantrace, but the everlasting value it's had to our firm.

That's great. I mean, it really is one of the truths about the technology business. If you don't disrupt yourself, somebody else is going to do it. And like I said, the early years of my career, I was with a number of companies, but they couldn't disrupt themselves. And those companies, if you see the multibillion dollar businesses that are out there, and there's a number of them in tech, of course, but they are constantly reinventing themselves. Some try to acquire it in, but I think the most successful ones today, whether it's servicenow or Crowdstrike or dynatrace, they're all innovation engines, and they're doing it with, they might pick up a little piece or a little piece or a little piece, but they're wrapping it into their organic innovation engine itself and expanding into new markets here and expanding this market there. And it's exciting to watch. And I think maybe that's a new trend in software in some ways, is that organic innovation model and how powerful it can be.

So, John, I just want to go over some history here and some timeline and some milestones, because it's pretty incredible. When you joined Diane Trace in 2008 as a venture backed company, I think the value was around $50 million. Then in 2011, a few years later, you sold to a large, publicly traded strategic compuware for $250,000,000. A few years later, in 2014, as part of our take private transaction, we assigned about $1.7 billion to that same company. And then in 2019, we went public for around four and a half billion. And then in 2021, when you retired, I think the market cap was 20 billion. So how does that resonate with you that you were the CEO of this company for a little over a decade, from 50 million when you joined value to retiring at around 20 billion.

Well, I look back and go, wow, that actually happened. But when you're in the throes of it, you don't really think about it. You keep your head down and just to get to that next. So from the venture standpoint, the milestone know, I knew that given I was on the east coast and the way the East Coast VCs think is probably going to be a sale to a strategic very few east coast companies actually get positioned for IPo exits. Just a difference in the way the VC world, but so I knew that was the goal. I thought it would take a little longer, but came in a little early. I will tell you, I wasn't super happy at that point because I knew there was more value. The market was big, the competition was stale. It was an opportunity, which is why I stuck with it in the next chapter. And the next chapter was interesting. We became a multi product line global business, absorbing resources from that compuware world. And then Tomo Bravo, unleashing it and carving us out. That was chapter three and then IPo and post IPo, chapter four. Maybe I should think about it as four different lives instead of one.

But with such a great continuum and such a great set of building blocks between technology, market and burn, I couldn't get away from it. I loved it. Absolutely loved the whole journey. And like I said, it's wake up at the end of it and go, wow, what a success.

Your commitment was really amazing and it was a pleasure working with you every step of the way. And I can't thank you more for joining us on this podcast, John, it was really a pleasure to get together again and I'm so happy we could share our story with a broader audience. This is truly a special transaction experience for us.

Thank you, Trev. I got to say, it was the same for me. Without Tomo Bravo, it just never would have happened. And it's not just because you carved us out or saw the opportunity. It was all along the way, many times providing advice, asking key questions at important moments, believing in the team and me, and some tough decision points that didn't seem obvious at the time. Great partnership and forever indebted. Thank you very much.

Thanks to John Van Sickland for talking with us today. If you want to learn more about diatrace, visit diatrace.com. And for more stories behind the deal, check out all of our episodes wherever you get your podcasts. Plus, don't forget to subscribe to behind the deal to hear new episodes as soon as they drop. If you like this episode, check out our mini series beyond the deal for bonus content from Jovan Sickland and myself that we didn't have time to share with you today. Catch it in this feed next week or on YouTube. From all of us at Tomo Bravo, I'm Chip Vernig.

Tomo Bravo's behind the deal is produced by Tomo Bravo in partnership with Pod People. Stay tuned for more stories behind the deal. I'm Orlando Bravo. Thanks for listening.

Certain statements about Toma Bravo made by portfolio company executives are intended to illustrate Tomo Bravo's business relationship with such persons, rather than Tomo Bravo's capabilities or expertise with respect to investment advisory services. Portfolio company executives were not compensated in connection with their podcast dissipation, although they generally receive compensation and investment opportunities in connection with their portfolio company roles and in certain cases are also owners of portfolio company securities and or investors in Tomo Bravo funds. Such compensation and investments subject podcast participants to potential conflicts of interest.