This episode of Beyond the Deal features a conversation with Thoma Bravo Partner Hudson Smith and former CEO and CTO of Mailgun, Will Conway and Josh Odom.
AIR DATE:
May 15, 2025
LENGTH:
22:01
DISCLAIMER:
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 construed as an offer to solicit the purchase of any interest of any Thoma Bravo fund.
Transcript
HUDSON SMITH:
Hi, I'm Hudson Smith, I'm a partner at Thoma Bravo, and this is “Beyond the Deal”, our bonus episode of “Behind the Deal,” and I'm here with the former CEO and CTO of Mailgun, Will Conway and Josh Odom. Welcome to Miami.
JOSH ODOM:
Thanks.
WILL CONWAY:
Thank you so much for having us.
HUDSON SMITH:
Great, well, this is the fun episode, guys. So, Will and Josh, just to start us off, why don't you give us a quick elevator pitch for the audience of what Mailgun does?
WILL CONWAY:
Email is an absolutely critical form of communication. There's not a single business that doesn't use it, and it's typically used in a lot of different fashions. What people don't know is that email is fully reputationally based in how it gets delivered. So, you have one part of the problem is actually having technology that can scale with your application. It can send out emails when you need to do the big burst, and then it can trickle them out when you need to do slow and steady.
You also have to scale the reputation alongside of it. So Mailgun takes care of both. We're equally potent at building world-class APIs that will scale with your application and bringing a managed offering in so that you're always partnered with somebody who can get on the phone with you and a postmaster of your choice to ensure that if things turn off or are not working the way that you expected, you can have that flowing the way that you need for your business to be profitable, successful.
JOSH ODOM:
That's right, and I think you may not have heard of Mailgun, but guarantee that each and every listener or viewer has email messages from Mailgun in their inbox today. So we —
HUDSON SMITH:
Two billion emails sent a day.
JOSH ODOM:
Yes, so Uber, Lyft, Microsoft, American Express, these are all some of the great brands that use the Mailgun email API to get those emails into your inbox each and everyday.
WILL CONWAY:
And the wonderful thing is that it doesn't matter if you're sending out five or you're sending out 5 million or 5 billion, Mailgun will scale with your needs as they stand.
HUDSON SMITH:
That’s great. Well, now that we know what the company does, would love to transition to talk about the two of you a little bit, because there's an interesting and long friendship between the two of you, you all met in college. And just curious, thinking back to then, did you ever think you'd be working together post-college, and how did this all happen, and how do you guys meet and start to become friends?
WILL CONWAY:
Man.
JOSH ODOM:
Wow [laughs]
WILL CONWAY:
Yeah, certainly, the answer is it was not the first thing that we thought when we met for the first time. Really, we have to give all the credit to our lovely wives. We both fell in love with these two ladies, who happen to be best friends; they are both named Jessica.
JOSH ODOM:
Which isn't confusing at all.
WILL CONWAY:
Yeah, it's easy at our dinner parties. So, I was a sophomore, junior in college. My wife was a freshman, and we started dating, and then I find out that her best friend, Jessica, who I'd become friends with too, she just started dating this guy, and within a month, he had proposed. So my girlfriend, now wife, said, “Can you meet this guy and find out who he is? Because that's wild,” so that's all I know about this guy going into it.
I met him, and first off, I think anybody who meets Josh knows that he is one of the most genuine, nice people that you're gonna come across and after hearing his story I came back telling my wife, “you know, I am in no way shape or form worried about him breaking her heart. This guy has been in love with this lady, like it's since high school.”
JOSH ODOM:
100%. I was stuck in the friendzone, so if nothing else, I'm proof that one can make their way out of the friendzone [laughs].
WILL CONWAY:
That's right, but you gotta go all in.
JOSH ODOM:
[laughs] You gotta go all in.
WILL CONWAY:
You gotta go all in. So we met, and that was just kind of the beginning of what was probably the most easy relationship we've ever had, I've ever had in my life. Josh is just a world-class developer, dev leader. I am doing my best to be a good go-to-market sales and CEO, so that we have fairly non-complimentary skill sets but very similar mindsets, so for us to be able to come together and Josh to kind of lay out the land of what is possible by way of tech, and then me getting to go out and just service it to the streets, it's just been a fantastic partnership.
HUDSON SMITH:
Yeah, the partnership is – and friendship is incredible. It's been a long one, and we didn't know that when I first met in 2018, but I knew something was up because when we went to the office, you two shared an office. So there was an office, you guys shared it, two desks, everyone else had their own offices around you, and, you know, you guys were obviously attached at the hip and making decisions. I mean, Josh, knowing Will, there's gotta be a time where he kind of got way out in front of his skis, but how did you rein him back in and pull him back to reality?
WILL CONWAY:
I feel like that's a very loaded question, that's for sure. [laughs]
JOSH ODOM:
Well, I think the crazy thing is, I think maybe from like an outsider who was observing Will, I think he does a great job challenging and pushing in, I think a very productive way, right? So, I think both of us believe in vigorous debate. I had to, being a little bit more introverted, had to kind of develop that over time, working with Will, but I think that others who may not have known us so well, like they would see that debate and be like, is this like an argument? Like what is happening, right? But like, ultimately, the culture that we were building was really one grounded in performance. So, the debate, the going back and forth, the challenge, right? Sometimes CEOs are out there and like, you know, they intentionally instigate not in a negative way but like to get the team moving forward and moving in the right direction and I think that there are often you know times where that debate for people who didn't know us maybe was like what's going on? But it was always rooted in trust, right? And when you have that trust with a partner and with the rest of the team, great things happen.
Will actually has a great product mind as well. So, like it is very uncommon to have somebody who has a sales persona and a product mindset, the two don't usually go together in most businesses. So, I think that often what made Will really potent is like he can pick up on patterns, what customers were saying, and then bring that to the team.
Ultimately, at the end of the day, both of us are commercial-minded. So, when there was a real, you know, debate about A or B, which feature is more important. Ultimately, the tiebreaker at the end of the day was: What's going to sell better? What's going to make more money and position the company better? And because Will has this product leaning to him, he is really able to, I think, orchestrate that really, really well.
HUDSON SMITH:
Yeah, there's a nice yin and a yang there between the two of you.
WILL CONWAY:
Nah, 100%, and because I'm a pusher and because I'm a challenger, I have to have somebody that I respect that just helps me understand how fast light moves. As CEO, ultimately, you have — it's your job to balance the room out, right? So when it's really just one strong person at the head of the table, that person has to keep an even kilter all the time.
I find that it's much better for me if I have somebody who can anchor me, and I can anchor them back. You know, in the same way that I very graciously got complimented on the product side, Josh is a phenomenal salesperson. I think that we have these aspects of this kind of overlapping and non-overlapping core skill sets. We play off of them all the time. You know, we always did this together from the very beginning, and you know, we have no pride of authorship. We're not the founders of this. We're stewards. So, probably the real answer to your question is every single day, like every single day I'm out over my skis, and you know, that's the way I like it, you know, I like being out over my skis. I like pushing, I love surprising people on what's possible but more importantly, I do like doing it with somebody else who likes doing it too.
JOSH ODOM:
And that became a big part of the culture, too, right? Like it was okay to try things and for things not to work, right? And great ideas can come from all different corners of the organization. We had people in support, right? That were working on building things for our customers, and that was a feedback loop. Our customers, prospects, of course, that was the feedback loop, but ultimately, at the end of the day, like great ideas came from everywhere and our ability to not have a lot of ego about it and listen and try things and of course, sometimes things just don't work, and you can move on to the next thing and our ability to move fast and pivot was just, I think, something that was so instrumental in our success as a company.
HUDSON SMITH:
And the team worked hard.
WILL CONWAY:
Oh my gosh.
HUDSON SMITH:
We all did, you all did.
WILL CONWAY:
Yeah.
HUDSON SMITH:
And it was a grind because we had a mission, we were growing 60%, we wanted to keep that up, we were doing M&A, we were pushing you to do something in France that you hadn't done before in terms of buying a pretty sizable French company with a lot of revenue, a lot customers, new markets, new people, new culture. It was stressful, the team was working hard, so how did you manage stress? Outside of the office? I remember [laughs] I remember your Jiu-jitsu, you know, you'd come back having fought people and feeling really pumped up before a board meeting, but yeah, how did that help you manage stress?
WILL CONWAY:
Yeah, man. I don't know that I managed stress in retrospect. I felt it every day. I never learned a trick. There was never anything that I really found that just made it to where I magically didn't feel all of the weight and responsibility that I had coming at me every day, the only thing that I could do that would in some ways put it in perspective was go ask grown men in pajamas to try to choke me unconscious because it's impossible to be worried about anything else, when there are grown men in pajamas trying to choke you [laughs] sweating on your face. So, it was like the only time that I would forget about like –
HUDSON SMITH:
That'll make you forget about a lot.
WILL CONWAY:
Oh, it'll make me forget about just about everything. So yeah, having something where I could release, and I will say this about — and I have to be honest, as the CEO job ramped up, I trained less and less, but one thing that anybody who's trained in Jiu-jitsu understands is you prove everything on the mat. It's such a humbling sport. It doesn't matter what walk of life you come into, it doesn't matter how much prestige you might have built up before you got into the room. The second that your feet hit the mat and you're training, you understand what this person is good at, what they're not good at. You get to know the character of that person so well. To me, that was absolutely pivotal. And the people that we brought into the business, I wanted people who I knew what they looked like under high strain, I wanted people that I knew what they look like in the path of evolution, in the process of evolution, you know, best and worst and I wanted them to know what I looked like, too. There's a lot of emotions that are coming in when you're doing something that can change not just your life, but the lives of everybody around you, and potentially your kids.
JOSH ODOM:
And I think at the end of the day, the stress is constant. But the thing that made it manageable was working with such great people.
WILL CONWAY:
Yeah.
JOSH ODOM:
I think, you know, when you do the math, you're spending way more time with your colleagues and coworkers than you do with your family. So a big part of our culture was being incredibly choosy about what we defined our culture to be, but also the people that came and the people that either self-selected out or, you know, when we made the wrong decision at times, being quick to admit that and move forward, because that was everything, right? You can deal with stress if you have a great team alongside you, but if you have a really stressful environment and have people that just don't mesh and fit well together. Well, that's a different thing altogether, and I think the culture that was cultivated allowed us to not only be successful, but manage a very high-growth company when it felt like everything was broken all the time.
WILL CONWAY:
No, that's an excellent point. Like — I hadn't actually thought about it. Really, the team being so comfortable with each other, and that we were able to be casual when we didn't need to go and introduce formalities, introduce all these additional elements. The team was really good about just having fun when the times were hard and making jokes. And if we did have to stay up late, we were playing music, and we were having a good time, you know, so that you could be around people that you genuinely liked.
JOSH ODOM:
Yes.
WILL CONWAY:
That you would hang out with on a normal course, like we’re all kind of in the same age. That was so helpful, that we were in that same stage of life, that late 20s, early 30s, that time where you have skill, but you don't quite have the achievement to go with it, and it's right there. And that made it so much more fun, not less stressful, but the fun came as equally as the stress did.
HUDSON SMITH:
And it's the same for us in private equity at Thoma Bravo. I mean, we're trying to do the same things that you are, like having fun at work, empowering people, just picking up the phone and getting things done, you know, it's that bonding in that environment and the trenches going to get a deal, win a deal that we try to do here as well. And the culture you've built was incredible, but in terms of Mailjet, that really was a big change, right? So you have this incredible growing company, it's growing rapidly, the culture is amazing, people are empowered, you've got this team that you trust, that you've been together for a while.
Those original kind of OG employees of the company are all still there, and, you know, you just trust them, and then you're now thrown into this European, Paris-based company, new people, new culture, different products. How did you pull them in and have them see the goodness that you have, and kind of integrate them into your culture? Or did you take things from their culture? How did you pull that off? Because the results spoke for themselves, the Mailjet business accelerated in growth once you guys got involved with it. So, how did you do it from a cultural standpoint?
WILL CONWAY:
So when we go out to Mailjet, you know, the first thing that you're ultimately looking at in most private equity theses is where are the inefficiencies. We came in there thinking that we were going to have to like, put on this bit of a dog and pony on all the great things that are going to be true around this acquisition. And obviously, the market position and these other things were absolutely true, but we started in the beginning by frankly going against our instincts and kind of sugar coating what was about to happen.
To the compliment of the MailJet team, they did not want that; they asked us to just be honest with them, and we went out on a ledge and we did. And we told them exactly what was about to happen. A bit controversial. And frankly, what we realized was that there were so many people in this asset who felt the same way about it as we did about ours, wasn't as many as there were in ours. Ours was more highly curated, but they were absolutely there. And they were fantastic performers, fantastic leaders.
Once we realized that they craved the truth. They craved the honesty. They wanted a logical path to success. They knew how to read a P&L just as well as we did, once we told them what we were going to do, how we curated through performance, and how that was going to help us go win against the gorilla in the space, the Titan, Twilio, and then of course they have their own competitors out in Europe that they were going against, I think they saw that and for those who, that thesis was right for them at the right time, those who weren't looking for kind of a lifestyle business, weren't just comfortable kind of going to work and not sure where this was gonna go. Those people saw it. It resonated with them. They stepped forward.
And we were given some phenomenal leaders. I mean, people that we wouldn't have known at the time, whereas the runways as far as they were, but with just kind of like the people who were not performing out of the way, this leadership vacuum, if you can do it, if you are willing to put the time into it, we will give you an opportunity to go and work your way and step into positions in the exact same way that we were given those opportunities.
So, I think that was really exciting for a lot of people at Mailjet at the time — obviously, not everybody, we had a mass, you know, once we kind of did our performance cuts, then we had a second tier of people that just left because they weren't happy with how implemented and you know at the time it felt like I felt like, “oh my god, we have to do all these cuts”
JOSH ODOM:
Yeah, I remember that.
WILL CONWAY:
Yeah, and then these other people are leaving in addition to, and we hadn't forecasted that, and we're running this thing so lean. In reality, it was the best possible thing that could ever happen.
JOSH ODOM:
That's right. The people that stayed were committed to the mission and wanted to move forward.
WILL CONWAY:
And they attracted more people like them. Even better, now we're growing, like Josh said.
JOSH ODOM:
It builds on itself.
WILL CONWAY:
Yeah, when you have a growing asset. Now the excitement's coming, and people are getting opportunities that they wouldn't normally get at this stage in their professional journey.
JOSH ODOM:
Yeah, and I think the other thing that really stood out in our approach was that we were willing to be there.
WILL CONWAY:
Yes!
JOSH ODOM:
I think, you know, it means so much, and you can build so much trust when you actually get off of Zoom or Teams or whatever your video conference tool of choice is and actually just sit in a room, go to dinner, have drinks, and build a real relationship and Will and I certainly spent at least a week, a month, many times two weeks, a month.
HUDSON SMITH:
Your passport was full.
WILL CONWAY:
Man.
JOSH ODOM:
Our passports were full [laughs], but not only did we do that, but our entire leadership team did that. We had people raise their hands and volunteer to be there for multiple months on end, like it was a real time commitment to start building bridges, identifying, “Hey, like maybe this person is underutilized, let's use them in a bigger role, bigger capacity”, so by being there, by enabling people to take on more scope, more responsibility, move their career forward. I think that was ultimately the thing that led to it being a successful integration in the end, though incredibly difficult.
WILL CONWAY:
Incredibly difficult.
JOSH ODOM:
Incredibly difficult.
HUDSON SMITH:
Sure.
WILL CONWAY:
As you can imagine, a Texas-based culture and a Paris-based culture, well, there's a lot of working out to kind of bring those together. You might be surprised, though, like, those fiery personalities actually kind of are around the same cloth.
HUDSON SMITH:
Yeah, very direct communication style.
WILL CONWAY:
Exactly, nailed it. So, once we got to that point, it was actually so much fun. Like, I think there's just something that's so intimidating about Parisians. If you've seen “Emily in Paris”, that's exactly how I felt. Literally, that happened to me. I went in and asked a bunch of people, I was like, “Hey, can I take you out to lunch?” And they're like, “Oh no, we're not gonna eat lunch.” And then I left, walked two blocks over, like, ate my lunch, came back, and saw them sitting and having lunch and smoking cigarettes, and I was like, “yo, not a good first week.”
HUDSON SMITH:
You were not invited to that?
WILL CONWAY:
No, not a good first week. But, you know. They're people like everybody else. They've been through something that's fairly new and traumatic, they didn't know what to think. So once we dropped our guards, it really was, It was, they were so much fun, like the best parties we had, I think, in the company's history were in Paris for sure.
[MUSIC IN]
HUDSON SMITH:
Thank you so much, guys, for coming to Miami. This was a lot of fun to sit here and reminisce about these old stories and learn more about Mailgun and the culture and what you built, and hopefully that will be enjoyed by our audience.
WILL CONWAY:
Yeah. Thank you so much for having us, and thank you so much for believing in us. It really changed our lives, and it was an incredible experience.
JOSH ODOM:
Absolutely. Thank you so much, Hudson.
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.
[MUSIC OUT]
