This episode of Beyond the Deal features a conversation with Thoma Bravo Partner Ross Devor and HubSync CEO John McGowan.
AIR DATE:
July 24, 2025
LENGTH:
19:33
Transcript
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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.
JOHN MCGOWAN:
It's good to operate within constraints. It's good to be budget constrained. It's good to put some time constraints on your business. So we put a lot of pressure early on to develop rapidly, to develop out to the market. I do think one piece of advice I have for any founders is getting — engineering is my background and strength. I mean, investing early on in engineering is invaluable. If you don't do that and you try to go cheap with development resources and offshore locations, which sometimes can work if you find the right partner, you're only going to pay for it later. And you know this. You've seen technical debt as you've evaluated companies, you're only going to pay for it later, either through bugs, through technical debt, or potentially through loss of revenue if you've got a platform that doesn't scale. So we were really, really focused on kind of engineering excellence out of the gate.
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ROSS DEVOR:
John, great to see you again. Thanks for joining us here on this episode of Beyond the Deal. It was so fun and informative to catch up with you on the last edition of Behind the Deal. And we're looking forward to hearing more of your background and experience today.
JOHN MCGOWAN:
Great to be on, Ross.
ROSS DEVOR:
So, John, can you start by giving us your quick elevator pitch on HubSync for the listeners who may not have heard that in our Behind the Deal episode?
JOHN MCGOWAN:
Absolutely. So HubSync is really the only end to end tax automation platform in the industry. We essentially white label our platform to CPA firms and they use us as the client collaboration layer between themselves and a taxpayer or an audit client. But we also do, is really automate the entire process inside of a firm as well. So if you think about a tax return, you have to issue an engagement letter. You have to collect documents from clients. You have to prepare the tax return, which we help with our work papers. You have to track the status of all the reviews and approvals inside a firm, which is complex for a tax return. You have to get e-signatures. And then you have to deliver the tax return back to the client. So it's a pretty complex process to produce a tax return or to produce an audit. We automate that entire function for a CPA firm and draw out a ton of hours for the firm professional while also providing a really modern client experience for the client through a modern client portal as well. So we're solving both the client experience and how they interact with the CPA firm, and we're making the CPA firm more efficient with our technology and our platform as well.
ROSS DEVOR:
Really interesting and I know we shared this, but I can say from personal experience, there's so much room for improvement in that process that you and I both live being a client.
JOHN MCGOWAN:
There's a lot of green space in tax and accounting for sure. We're just getting started.
ROSS DEVOR:
Exactly. We talked a little bit about that backdrop before, but I'd love to zero in on your background here, given that you're not only the CEO of HubSync, but you're the founder. You started the company. So can you take us back to the early days of the company and talk through some of the initial challenges of getting off the ground and how you took some of your background into launching this company?
JOHN MCGOWAN:
Absolutely. So I — as I described on the earlier podcast, I really built earlier versions of HubSync and the big four when I was a CIO at KPMG and Deloitte. And so I had massive budgets and hundreds of developers to build something like HubSync inside the big four. And what I found is the market right below the big four, the top 100 firms, really lacked the kind of modern end to end platform like HubSync could provide. So I left Deloitte as a partner in mid ‘18. Some people thought I was crazy to leave Deloitte in a safe job to start HubSync. And really I had this hypothesis about what HubSync could do for the market. So I actually bootstrapped the company and started with consulting. So I actually started consulting with a lot of large top 25 firms. Again, I felt like the top 25 firms were the firms that wanted to be like the big four, but didn't have the technology development capability to build something like HubSync. And they were frustrated with some of the legacy technology providers. So did a lot of consulting and bootstrapped it for those founders out there. Sid bootstrap Hubsink very early on, didn't pay myself for a long time. Every dollar that I made with my consulting practice, I put it into the product and really prioritized the build of Hubsink. I also didn't build the entire platform behind a curtain for two years. I saw the biggest pain points and problems. I built this one module at a time and I really just started selling HubSync and becoming profitable earlier. I was a firm believer that I didn't want to be developing a startup for years and then uncorking this. I really felt like let's match the technology to the problems that I was seeing and develop this module by module. So that approach was really, really successful. We were able to partner with early firms like Baker Tilly, who saw the promise of what I was building with HubSync, and they really became kind of one of our key anchor clients and then slowly was able to get a lot more logos using the platform. But we were really, really lean early on. I had a good idea that we had a really good product market fit. I know a lot of founders question product market fit. I knew I had product market fit. was just something that I was building was very, very bold and ambitious and sort of what's the best place to start and really listen to my clients in terms of how I prioritize my roadmap and built the initial stages of the platform.
ROSS DEVOR:
And that's a big customer to make happy out of the gates, right?
JOHN MCGOWAN:
Yes.
ROSS DEVOR:
Like you said, you focused on the top 25. Tell me about getting one of these top customers, your first customers, live and happy and successful. How was that?
JOHN MCGOWAN:
It was a challenge. I mean, I think, you know, the technology is the one piece, but adoption is the other piece. So I think when I worked very early on with the leadership at some of these firms, they were like, “well, of course everybody's going to want to use this new module that you've built, John, but, you know, building the technology and throwing it across the wall is not going to work”. So part of what we've learned with HubSync is not only building great tech and a great platform, but really partnering with our clients on adoption. AndI saw this in the big four too. We would develop amazing technology and we would always be like, “why aren't people using our standardized work papers, or why aren't they using a new module or capability that we built?” So, you know, there's a lot of change happening inside these firms as we talked about earlier. And really what we've learned is we can't just develop great tech, but you have to partner with these firms on rollout, on adoption, on training. So we've invested a lot in customer success and we have a lot of people inside of HubSync who've worked inside these CPA firms. So we have tremendous credibility when we can walk in here and say, “We've experienced this pain ourselves as tax or audit professionals. We're here to help you.” So I think the biggest surprise was year one, we expected a lot more adoption of the first module that we built and the head of tax was like, “wait a second, why don't we have more adoption?”
So typically what we see is first year, sometimes not as much adoption. And typically we joke around firms typically then use the m- word, which is mandatory and making some of the technology and standardization mandatory. So once some of the tech becomes mandatory we obviously see adoption skyrocket. But some of the early days required a lot of handholding for us to help these firms. Now, of course, we've got a great playbook on how to deploy HubSync and all the modules and the training, but early on there was some growing pains in terms of adoption inside these firms.
ROSS DEVOR:
Yeah, I'm sure, I'm sure. And yet still with that large kind of challenge and kind of enterprise focus you had, you didn't raise a bunch of money and push aggressively to raise a bunch of money, burn a bunch of money. Talk to me more about your views on efficient growth, because it really stood out to us as we looked at, you know, your efficient kind of profitable growth stature compared to other profiles that we see in the growth stage.
JOHN MCGOWAN:
One of the early books that I read was Getting Real by Jason Fried, and he's the founder of Basecamp. They're a $280 million company, and Jason, you know, built Basecamp with 20 people and didn't take any investment. He took a small investment from Jeff Bezos early on, but he was a firm believer — don't take money. He calls it the magic of startup land. Like, pre-revenue, you've got a bunch of money, you've got seed investors. There's no pressure to go out and actually be profitable and get a product out. So I really was a firm believer in that same kind of mindset. Like, let's build the first product. Let's solve a pain point. Let's sell it. Let's iterate fast. Let's get feedback on these products. As you know, we're profitable. We've been profitable. So I didn't want to raise a bunch of money, build HubSync behind a curtain for a couple of years. And then on uncork it. we really built this bit by bit with our clients. And as Baker Tilly continued to see these new modules coming online, they just kept buying them, which was fantastic. And then we saw that case study really take off with some other firms who wanted to do the same thing. So I also had this hypothesis that there were a lot of firms in this group that really wanted to be more efficient like the big four, but couldn't do it because they didn't have some of the technology budgets to build this themselves. So once we kind of had the Baker Tilly case study and success, we were able to move. Now we have a bunch more firms that are using the product. But yeah, we were firm believers in being lean, iterating with our clients and being profitable from day one and trying to stay profitable, which has really served us well as a company.
ROSS DEVOR:
Yeah. And I think that's very apparent to someone like me who — you probably can't build that profile unless you have such pull from your customers that they want more and more of what you're serving. And if you can do it well like you did, you really unlock a special business profile, which is exciting.
JOHN MCGOWAN:
The challenge that we had early on Ross was like, and some founders may hear this as we were doing a series A and others is customer concentration. And, you know, I would tell those investors, the customer concentration was actually intentional. We wanted to build this with a smaller group of clients and ensure that the larger firms were successful with it. So the strategy on the customer concentration was actually intentional. We had a few people on the series A pass cause they didn't like it, but it was an intentional part of my strategy. As you know, we talked about this during the process. Obviously now we've got a lot more clients, but I really think you don't necessarily need to sell your product to hundreds of different clients. You know, we were very successful building this with a smaller group of clients, you know, pressure testing the HubSync platform, really validating that this was adding value, ensuring that we had product market fit. And then it was much, much easier to sell to the next top 25 firm. And now obviously we're selling down to the top 200 firms as well. So we also developed this in a way that we knew we could scale this down market.
ROSS DEVOR:
Interesting kind of flip side to what you usually think about as you grow a business. Any other kind of contrary advice you'd give to other aspiring founders, you know, who are building products and companies out there?
JOHN MCGOWAN:
I think it was great. The other thing about getting real and Jason Friede is that it's good to operate within constraints. It's good to be budget constrained. It's good to put some time constraints on your business. So we put a lot of pressure early on to develop rapidly, to develop out to the market. I do think one piece of advice I have for any founders is getting — you know, engineering is my background and strength. I mean, investing early on in engineering is invaluable. If you don't do that and you try to go cheap with development resources and offshore locations, which sometimes can work if you find the right partner, you're only going to pay for it later. And you know this, you've seen technical debt as you've evaluated companies, you're only going to pay for it later, either through bugs, through technical debt, or potentially through loss of revenue if you've got a platform that doesn't scale. So we were really, really focused on kind of engineering excellence out of the gate. We really feel like that's the foundation for great products is to have a great engineering team. And all the rest of the things can happen around that customer success and sales and marketing, but you have to have a great product. That's where it all starts.
ROSS DEVOR:
Sure, and a follow-up to that, John, is tell me a little bit about your leadership style and how that might have evolved from the early stage, you know, one or two employees of the business, to now in this growth stage that you're in.
JOHN MCGOWAN:
Well, I, you know, I consider myself sort of, if you look at the spectrum of leadership styles or transformational, I mean, marching to a vision, being a very client centric and everything that we're doing, being bold, being innovative as a company. So I like to lead by example. So I'd say early on, and continue to be to some extent, we're really a product centric company and I'm really a product centric CIO and CEO. The early days of HubSync, I was designing — working with developers very, very closely. I was involved in all aspects of design, development. And I had a lot of background and context on what went right in the big four, what went wrong. The consulting that I mentioned earlier really helped inform the right way to build the platform. But obviously as CEO in a bigger company, I can't be involved in product all the time. Now there's go-to-market, there's customer success, there's meeting with clients. So this is part of what we want.
The help from Thoma Bravo is continue to hire into HubSync to allow me to focus on growing and scaling the company. But we still at our core are a really product centric and customer centric company. I mean, I think it's all about the product for me and it's all about our clients and listening to our clients, building great software. We wanna scale the company through the help of Thoma Bravo and the investment that you're making in HubSync. But we're really at our core, a great software engineering and product company. And I want us to stay that way, because I really think that's the value that we can provide to this industry.
ROSS DEVOR:
Yeah, and that product orientation in your background was really, really clear right from where we started the conversation — our very first conversation was just right into the product and how you've built it, which kind of jumped off the page to us, and why we love backing kind of product-oriented founders like yourself. But I guess part and parcel to your leadership and culture is your own personal, I guess, fitness routine. And I've heard about this home gym you have here in Tennessee. Tell me more about how you've always been into fitness and how that kind of influences getting ready for all the work you take on.
JOHN MCGOWAN:
I'm not in the shape I'd like to be right now. It's been busy lately, but no, I've been in fitness my entire career, athlete, you know. Even into my thirties I was powerlifting. Unfortunately, I have two back surgeries to show for it now. So now I'm a little lighter on my body, but no, I love a morning workout routine. My tricked out gym — my great tricked out gym was actually in DC. I still have a pretty good gym here in Tennessee as well.
But no, I love lifting weights. I love a bike ride in the morning. I love getting outside and getting on my bike and going for a light long bike ride. I love to get my workout in in the morning if I can, it kind of sets my day and starts me right. I've got a routine around some meditation and journaling and affirmations and some things that I do every day as well. But for me, it always — it really starts with fitness, your health. If you're not healthy, if you're not feeling good, I'm not going to be a great CEO. So really, you know, fitness and health is really, really important to me as a big foundation in my life. And my wife, as you know, owned a Pilates studio as well. So she's equally into fitness. So, she's got me doing Pilates and yoga now to help me with my, with my back.
ROSS DEVOR:
It's not just all power lifting at this point, and lightening up some pilates.
JOHN MCGOWAN:
No, no more powerlifting. Those days are long over, Ross.
ROSS DEVOR:
Yeah. Exactly. That's good. I don't want to get into competition. I'd probably lose that. But no, share the same focus on kind of starting out the day. And I feel like on both of our plates, work take so much. You got to kind of bring your A game starting with your health and fitness overall. And I share that with you.
JOHN MCGOWAN:
You do. I think that I also, you know, my assistant always blocks some time in the morning. I've always tried to block time in the morning for strategic thinking as well. I mean, the day can just start to get away from you. And I love thinking about “where am I taking the product? You know, what's the next 90 day plan”. If you don't take that time in the morning, I just find it's harder in the afternoon. The day gets away from you, client meetings, other things come up. So I always try to block time in the morning to focus strategically on HubSync. I've always done that in my career. I think it's worked out well.
ROSS DEVOR:
And if you do get some downtime, which I — given how much we're texting and emailing, I'm not sure I've seen yet, but when you do get some downtime, any books or TV shows you've seen recently that you've enjoyed?
JOHN MCGOWAN:
Not a lot of TV shows. I just read Blitz Scaling by Reid Hoffman. I love that book around how do you, you know, Blitz Scaling and how do you scale and really disrupt and grow quickly. That was a good book that I read recently. I'm kind — of being in Nashville, I got to tell you, Ross, a lot of country music. So I'm going to see Jelly Roll and Tim McGraw coming up. I've seen Old Dominion. I've seen Kenny Chesney. I've seen a lot of great bands, Zach Brown Band. So I'm a big country music fan. So I've definitely have moved to the right city.
ROSS DEVOR:
That's amazing. Any favorites in that list?
JOHN MCGOWAN:
I like Zach Brown Band a lot. They're probably one of my favorites and they put on a great, great show. So we saw them. Seen Tim McGraw a couple times too. I'm a big fan of his as well, but I'd say Zach Brown Band is probably my favorite.
ROSS DEVOR:
Amazing. You've already given me some homework since our first couple meetings in Nashville to get schooled up on country music. I won't say we're organizing our board meetings around certain concert events, but if they happen to coincide, —
JOHN MCGOWAN:
You've got to see a concert here. You go to the Ryman Auditorium, it's amazing. You can see some amazing people at the Ryman. It's a small venue, great. I mean, I saw Old Dominion there and Kenny Chesney popped up as a guest singer. So you never know who you're going to see inside Nashville.
ROSS DEVOR:
Incredible. We’re going to the country hotspot. I love it. I love it. And I guess to round things out here, John, could you share something that you wish you'd known at the beginning of your career?
JOHN MCGOWAN:
That's a good question. I'll probably answer this maybe a little differently than you think I'm gonna answer it. I wish I'd learned to code. I really wish I'd learned how to code early in my career. There are many times during the journey early on, Betsy would tell you, I would say, I wish I could just code that myself. So I have a great respect for technical founders. I think they have a huge advantage. Someone who's a technical founder and can code and program. I know enough to be dangerous. But as I look back, man, it would have been amazing if I could have coded some of HubSync myself early on. So that's something I mean, I started with tax background and a master's of tax, but as I look back, I really wish I'd done some computer science and learned to formally program. It would have helped me a lot as a founder. I'll ask the same question back to you.
ROSS DEVOR:
Oh, that's a good question. Something I think about a lot is this marriage of great innovation and great business building. And when I started in my career, you were either one of two camps: private equity or venture capital. And what I love about partnering with you and HubSync at this stage, is it really shows the power of kind of two philosophies coming together — great product innovation, but also thinking about how we organize and operate our business to take that technology to the next level by driving, you know, finding more customers, satisfying more customers and getting them to engage better.
And so I wish that this kind of concept that we are now bringing with our growth fund at Thoma Bravo was more available and more understood of this kind of hybrid of bringing great operational backgrounds and, you know, DNA from our portfolio, but bringing it into a product-centric and growth-centric company. And so I've seen that kind of become fused. And when I work with an entrepreneur like yourself, it's very much this pragmatic, growth-oriented, but yet operationally focused fusion. Which is so fortunate for myself personally to have found that mix and be working with folks like yourself in this kind of great hybrid strategy of growth oriented, long term profit building with great companies and serving great customers.
JOHN MCGOWAN:
Well, we're excited to take all the knowledge you've learned, your team has learned, and how you've scaled so many great SaaS companies and apply that to HubSync. We're excited about the future working with Thoma Bravo.
ROSS DEVOR:
I guess lastly, any demands on jerseys I've got to buy with our affiliation for the tar heels and —
JOHN MCGOWAN:
Well, you're behind it. Somebody already gave me a Drake May jersey. That's one I've received. Well, know, I'm kind of, I'm unique in that I'm a football fan first. Most Carolina fans are basketball fans first. So we're actually excited to see what Mr. Belichick can do with the Tar Heel football program. So any football jerseys you want to send my way would be appreciated.
ROSS DEVOR:
That's good. We'll leave the critiquing of Belichick and the strategy for the next podcast. But this is really great to get a little bit more —
JOHN MCGOWAN:
That could be a podcast in itself.
ROSS DEVOR:
Exactly. Exactly. On a different top 10 list, maybe.
JOHN MCGOWAN:
Exactly.
ROSS DEVOR:
But thanks so much, John. Really great to again partner with you and the HubSync team and spend the time together talking about your background and how you're building the business. So thank you.
JOHN MCGOWAN:
I enjoyed it, Ross. Thanks for your time.
ORLANDO BRAVO:
Behind the Deal is brought to you by Thoma Bravo in partnership with Audacy’s Pineapple Street Studios. Join us next week for more stories behind the deal. Thanks for listening.
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