Exclusive: Selling My Company & Making Life-Changing Money

We signed the deal. We did what's called a split sign and close. I think I told you this offline, but like, so we signed on the 21st of December and we closed on the 4th. So imagine the most like anticipatory 2 weeks of your life. The deal is done.

Like, all this is— I don't know if we're going to run this, but this is the M&A version of blue balls.

Yeah, I didn't want to say that, but yes, it's just like Oh my God, is it gonna like it's gonna happen? It's like yeah, you know, and then your family like nobody knows to congratulate you. Like but I was like that's not close, and my dad's like a real estate guy, so he's like you don't you stay on this every day until like you know it's not done until the money's in the bank. Like so there's all these like it's just like sitting there, and that was a like just a highly anticipation oriented period.

What's up everyone? I'm Alex Lieberman.

Yo, this is Jesse Pujji, and this is the crazy ones.

Okay, I'm going to start with something. I have a little surprise. Oh, tell me if you can hear this.

It's the acquisition alarm.

Ladies and gentlemen. Welcome back to The Crazy Ones. My co-host Jesse, Class A crazy, officially sold his business Ampush after what, 13 years?

13 years. 13 years.

Yeah, the 13-year overnight success. Congratulations, man.

Thank you. Thank you.

We are going to talk about a lot on this episode from the origin story of Ampush, what the business is so that you have some table setting, but then What the process is like of selling a business. It's it can be brutal at times. It can be long, but there's so much you learn. And then, of course, I'd be remiss to not ask the the squishy questions about the emotions around the process. What it was like to share the sale of a business with your family. So we're going to hit it all. Stay tuned for everything, and welcome back to the crazy ones, everyone. Okay, so. You sold your company. I saw— pretty funny. I saw the, the announcement on Google, I think, before you saw it.

I was just going to tell you, you were the person who told me that it got announced.

It's so ridiculous.

You didn't have lesson number one of selling your company. It ain't your company anymore. So they didn't— they didn't call me and go, hey, can we send this press release? That is the most ridiculous thing. Last week. And then I was just told like, it's going to go out sometime this week. And then literally like you go, hey, it's public now. Can we talk about it?

It's It's absolutely ridiculous. I have to start with one question. How much did you sell it for?

One day I'll share that.

I was talking to Jesse before this. I said, is there anything off limits in this conversation? And he said, nothing is off limits except for talking about the price. So I had to ask.

I think the pertinent detail is like it was a very good outcome. It was— it's like life-changing and it's sort of— it is the moment. I think I dreamed of as a 20-something, you know.

Yeah. How old were you when you started? Do you remember the exact date?

Well, here's a funny story. So the name Ampush, you know this, but the audience might not know this. It's, it's the first 2 letters of the founder's last name. So Chris Amos, Jesse Pujji, Nick Shaw. And our first company, we started sophomore year of college. We were super douchey and it was called Amos, Pujji, and Shaw Inc. It was like, oh my God. And it was our t-shirt business and You know, one day we were looking at the forms for it, and Chris, I think, came up with it. Chris looked at it, he goes, "Man, that spells Ampush." And then, like immediately, we jump on Google. Like, is that domain available? And it was available. So we've owned the domain and have kind of used that name for various things since 2004.

I love it.

That's how old it is. And then, and then we held on to it, and we didn't do much. You know, it, and then the company sort of as as a real business, and you know, and as adults. Was we started in 2000, late 2009 and 2010.

I will say the name has a very good ring for it, ring to it for like assembling initials of names. Usually when you try to do that with founders, like it doesn't work out. Like if I try to do it with Austin Reef, Alex Lieberman, it would be like Lara. And I really would have been upset if Morning Brew's name was called Lara. So it's a catchy name. I want to— okay, so the way we're going to do this is I want you to just set the foundation of the sale. So, you know, when the deal was done, who you sold it to, and then we're going to pull— we're going to pull back the timeline and start working towards, you know, this week that everything just happened. So tell me a little bit about the acquisition.

Yeah, sure. So it was acquired by a large tech-enabled marketing services business called Tenuity. And Tenuity has a really cool origin story itself, but it was, it was a roll-up of a variety of different marketing services and agency businesses. That business is backed by a really awesome private equity firm called New Mountain Capital, who I got to know really well. I knew a little bit prior to this process, but really got to know them well and like love their approach. They're all about finding a good sector and actually buying a bunch of businesses inside of it to create a bigger business. They're super entrepreneurial. Some of the partners there were awesome, like they were, they were generally really great party. So The reason they bought the company, you know, they had had their eyes on it for multiple years. And so when we finally kind of put up the flag, which we can talk about, they pounced and they pounced pretty hard on it, which was exciting to see. They, you know, they had bought one small social agency without a lot of tech and, and data chops. And I think they were— they felt like they could really— that the Ampush offering would enhance what they were doing in a very meaningful way. And so I think for them it was They're trying to build the most— the large— I think they call themselves the largest independent performance marketing business out there. They run Amazon television, Google. And I think this was sort of an area where they thought they could, they could build something really awesome and big and kind of upgrade their capabilities.

And I feel like that it's a relatively common strategy in, I guess, like the private equity middle market world where like you have kind of like an anchor business and then that anchor business does all these kind of add-ons to increase the overall value, right? Like that's a common practice.

Yeah, very common. The other thing that happens, you know, it's kind of a cool thing is it's called multiple arbitrage. And, you know, one thing that just happens in businesses as your business gets bigger, investors pay a higher multiple. It's more stable. It's demonstrated more sort of staying power. And so what a lot of these private equity firms do, and we were sort of a part of this arbitrage, was, hey, I can pay you, you know, X multiple I can buy at X multiple, but I can sell at Y multiple, and Y multiple is, you know, 2x or 50 to 100% greater than what I'm paying. And so naturally, every time I bring on a dollar of profit, it's worth more to me as the holder. The other cool thing is, you know, especially our management team and our CEO got a lot of equity. We got a little bit, which was by design. But so we're riding a little bit with them in terms of what's, what's going to happen.

Got it. Sweet. So I want to talk through the mechanics of the deal, but I would say probably some chunk of our audience knows your different businesses between Ampush and then all of your GatewayX businesses. But also, you know, I think the pod has grown a lot in the last month or two. So there are people who may not know your story and what Ampush is. So can you just provide context on what Ampush is, you know, when it started, what, what the offering was so people can understand why a company would look to buy you guys?

Yeah, totally. Let me take 5 minutes to tell the whole saga because I think it's worth it. Just because I think you will appreciate the wholesale more knowing what all has happened. Because Ampush has really— I mean, Ampush for me, and just to get the emotional a little bit, like it is the place I grew up as a business person. It's where I learned all the things I've learned. Everything I do without a doubt from here forward and from here forward will be Ampush at its core in some ways. Right. And it's, it's just like the first of anything, right? It's the first child, the first love. Yeah. And it's also been multiple businesses. So I'll tell the story. You know, I mentioned earlier my college roommates, all of us went to go work in like finance. We were in the financial crisis. Nick, one of our co-founders, you know, one of my partners, he was going to a hedge fund in 2009 and he gets an email. I get an email or message one morning from— I was sitting at Goldman Sachs and it says Blue Wave has blown up. It's down 40%. And I wake him up. He's in India at the time working at Morgan Stanley. And I'm like, hey, Your hedge fund's gone. Like, and he kind of paused and he was like, you know what? I was like, are you going to— I can get you job interviews. No big deal. We'll figure this out. And he's like, I'm going to chill. I'm going to see what happens. And so he actually— I think that was a big move for him without us. I was still at a job and Chris was at a job and he said, I'm going to just hang out. And he like started kind of working on a project. And then, you know, you call me every week for advice. And then like, you know, as these things snowball, I was kind of like, I wasn't loving the job anymore. And, you know, one funny story is, you know what GLG is?

Yeah. Yeah.

So it's Gerson Lehrman Group. It's this expert network where like private equity firms and hedge funds can call experts. And so I told my firm probably in late '09, I'm leaving, I'm going to go start a business. You know, if you leave for a reason like that, they're very supportive. So they're like, oh, why don't you hang out for a few more months, transition your work? What can we do for you? So I was like, well, I want to just use GLG. Goldman has like an unlimited, probably million-dollar-a-month subscription to GLG. And every day we had 3 experts calls with like digital marketing experts. It was amazing. I mean, dude, you couldn't ask for—

That is the most incredible hack.

Best hack ever. We got the sell-side internet analysts to come pitch me and tell me like, what's the growing sector? And so we had a lot of support in getting it going and we were really keen on bootstrapping. And I think I have this deck. I don't think I've ever shared it with you, but I will, which is like all about creating a really cool culture, generating cash flow, and then multiplying it many times over. And many times like what GatewayX is today, that vision was, was back in 2009, we had no idea how to execute it, but we wanted to find a business we could get going, we could start and sort of multiply on top of each other. And so we heard from people, they said, oh, you're good with numbers, data, go look at digital marketing. Okay. So a bunch of 25-year-olds, we said, okay, we'll go look at digital marketing. We start poking around, we go, we have no relationships, we don't know anyone. They go, well, there's this one sector called performance marketing. It's kind of like Wall Street. You spend your own money and if it works, you make some money back. And if you don't, it doesn't work. So we're like, okay, performance marketing. We're like, what's a good space to do this in? And at that time, just totally randomly, you know, Kaplan, University of Phoenix online education was having this day in the sun because it was a recession. There was like this legal issue loophole that they were taking advantage of. So we decided, just totally screened our way into this, meaning, you know, no passion, which is like we're going to start generating leads for online universities using digital marketing. We're going to arbitrage it. We literally bought AdWords for Dummies, start reading them. We had financial models and PowerPoint presentations and we didn't know anything. We hadn't made a single sale. We— for 8 months we did this. The one funny hustle thing we did, you probably heard this story from me, is there was a company called QuinStreet that went public early on in us getting going. And a friend of mine called me who was a hedge fund guy and was like, isn't this what you're doing? Like, this sounds really familiar. And he's like, explain it to me. So I started walking him through how digital marketing works and How you buy a click and then you get a conversion. And he, he was like, this is amazing. This is so valuable. And like the light bulb went off in my head and I called GLG back and I'm, you know, I used to be a customer. I go, can I be an expert now? My rate is $500 an hour. And I was like, are you getting questions about this QuinStreet company? And they're like, yes, we are. And I'm like, great. And I start getting these calls for $500 an hour. And then someone goes, do you have more research or data? You know the space so well. And of course I'm like, sure we do. So Nick and I spent one weekend making a 50-page deck. I'll send it to you after this call. We can post it. Yeah, it's all about the online lead gen industry. And we started selling it for $5,000 a pop to hedge funds. And for a minute we were like, should we do this business? Like, this seems like a way better business. So anyway, we were, we were doing a bunch of random stuff for the first, you know, 8 months.

Were you, were you using that just to fund your business?

Like, was it enough? Yeah. I mean, the way we funded the business was the 3 of us. There are a few sources of capital. The 3 of us each decided to put $33,000 in, which we had made kind of working on our Wall Street jobs. We were 25, 26. We had one of the most unique arrangements in the history of co-founder arrangements, which was Chris had a commitment to Carlyle. He was at private equity and he had 9 more months left on his contract and he didn't want to burn the bridge and leave early. But we all agreed that basically we would treat ourselves as one entity and he would give up 2/3 of his salary to the end, to the entity while we, we tried to get the company. And that's how we all remained equal partners.

That is so interesting.

It's like the our accounts were like, this is the craziest arrangement we've ever seen. And then, and then we used credit card debt like we used American Express. Actually, one of the saddest moments in the closing of this deal was when I had to cancel the Ampush Amex because I was like, oh my God, this thing. Like, I hope you kept the card. Yeah. I mean, it— I have the card, but it's like, damn. Yeah, it was a moment. But, and then, and then, and yeah, we sold these reports and other hustles to kind of give us enough money to keep going. So Anyway, we learn how to do these ads. We build a landing page and a website. I think I'm super smart, you know, start running Facebook ads or Google ad campaigns on AdWords and just start losing our ass. I mean, we would spend $5,000 and we'd get 5 leads.

So you were just— you were just shitty at the one job you were doing.

The one— I mean, beyond shitty, right? And like, didn't work.

Yeah.

Over— made it so complex, overdid it. And we're just like, what were we thinking? This was a terrible idea. We don't know. We have no idea what we were doing. Like, it really hit us at that moment. You have all the, like, kind of positive version of it. And we had no— you know, this was something we were starting from a cold start. You know, we had nothing going for us. So we just— we grinded for 90 days, eventually started making like a 5% profit using Google Ads and just really simplifying it, frankly, copying our competitor.

We just found what competitors were doing and started copying, which, by the way, is like the best hack in the early days of the business is just look at a competitor who probably has tested Everything because they're everything, right?

They're buying this keyword, they're sending to this funnel. Like I literally went that was the final solve. I was like, I want I want to because we we were trying to make our website really fancy because we thought the websites in the space looked shitty. Yeah. Then we realized no no no we're we're the you know we don't know what the hell we're doing drag and drop nobody wants that they want to quickly move through the funnel and submit a lead right? Totally. So so we start copying a better making a five ten percent margin on what we're doing and you know that was right around the time Facebook had launched the first version of their self-serve ad platform and. We actually ported over the same— back then there was this thing called AdSense, which is now Google Display Network. And you could say like categories like, oh, painting or drawing, oil painting, and they would contextually target on a website. We took those same exact ones and copied them over to be likes and interests on Facebook. And then we'd make ads that were like, are you an art, art, art lover? You should get your online degree at, you know, whatever. And what was a 5% margin on Google was a 75% margin on Facebook.

Why?

Well, we were the first. We were the first mover.

Yes. So there was just no demand there yet.

There was no demand. No one knew how to use it. You had to build one ad at a time, and literally within six months of doing it, we had guys in India doing it. It was our first version of Growth Assistant, right? But we had people just uploading one ad at a time and going, and then the clients called us and said, "These are amazing leads. Where are you getting them?" And we said, "Oh, well, we figured out." We you know, and that became this calling card. And here I'll tell you a crazy story. In June of 2010, the business did $100 grand in gross revenue. By August of the following year of 2011, it was doing $2 million a month in gross revenue. It just— it just skyrocketed. I mean, and it was all Facebook, right? And it— I mean, we were not all Facebook, but it was 70% Facebook. We were scaling it as fast as we possibly could.

Were you scaling clients or just you were Scaling a ton.

Okay. Yeah, because there's only 20 clients that matters, like Kaplan University, University of Phoenix, Art Institutes.

So you're still all exclusively in education, all in and expand.

Yeah, correct. All exactly all in education and growing that business really fast. And then, you know, we started to get a little bit like the whole lead gen category performance marketing is a little bit skeezy. Like we go to these conferences we didn't like, you know, we just like, this is not a space that we were proud of. You don't tell our grandma about it. Like there's a lot of you're selling people's information. It just wasn't, wasn't our cup of tea. But the business was making a lot of money. And, and by the way, it was, you know, everyone's listening like it was making millions a year in profit and we were 18 months in and all coming from Facebook. And we got, you know, a call from Facebook and actually really one of these serendipitous things where our account manager was this awesome woman named Pat Lai, and she moved internally at Facebook from the account management group to the partnerships group. And one of her mandates was go find companies that Facebook can partner with to build around their ads ecosystem. They can build software, they can build services. So Pat, I jokingly call her the 4th co-founder. She was, she was like, guys, stop this lead gen stuff. You're like literally so smart on the platform, you should be building a software and tech platform. And so in early 2011, I think I broke off and Nick and Chris continued to run the core business and I started a new business that for many years we called Ampush Social. Now, eventually we sold the lead gen business off in like 2013. We divested it. We can talk about that. And we went all in on the social business around late 2012, early 2013. We went all in on it. And, you know, at that period, we were one of the few companies who knew how to make Facebook ads work, one of the few who had access to Facebook's unique API. We knew it wouldn't last forever, but like we were early to it and we were getting calls and customers that like today are dreams. They were tiny companies then. We got this one coming like, They got cabs in 10 cities. Like, I don't know if it's going to be very big. And it's like, oh, it's Uber. Okay. And like, next thing you know, we scaled them to 600 cities globally. We were spending $50 to $100 million a year with them on driver acquisition, getting drivers to sign up to be on the platform. Dollar Shave Club, Clash of Clans.

It's insane.

Peloton, Blue Apron. I mean, you name it. Like, we had a stat that 8 out of 10 unicorns have been Ampush clients at some point. Yeah. And so for us, it was, you know, We originally wanted to be a SaaS business, by the way. Nobody wanted to buy the software. They wanted services. We were bootstrapped. We didn't, we didn't know SaaS servers. We didn't know any of that shit. We just said, great, they need services. We're going to— we start hiring young, really bright kids, training them on how to do this. Nobody, you know, 80% of AMP pushers don't have a marketing and advertising background. We taught them from the ground up. The business grew, grew, grew, and grew. And, you know, 2015 came around. I was probably your age, a little bit older, 30. And we were like, we're going to sell, we're going to grow really fast and we're going to sell. And we ran this process and we ended up with a handful of really good offers. But in my mind, I thought we were going to sell the business for 9 figures. I was like, we're going to sell it for 9 figures.

And how big was the business then?

Can you say? I probably shouldn't, but it was— well, so what we'd been told at the time, there was like companies like Rocket Fuel and Marin Software that were trading— were billion-dollar market caps in 2012 and '13. By 2015, '16, they had gone down 80, 90%.

Why?

And so as somebody, they were just, they were just ad tech businesses that weren't— they were sort of overhyped. But when we greenlit ourselves the strategy, we said we're going to grow and sell for a huge multiple. Basically, the multiple collapsed, like didn't come in. It was still life-changing money. It was still bootstrapped, no outside money. But one of my big lessons from that, looking back on it, was like, I did not understand my emotions. I didn't. I was so sad and disappointed. because I was like connecting myself to my valuation. I was like, no, that's wrong. That's wrong. And I was like, no, the market's never wrong, right? I mean, you go out and you say what it is. And so we ended up, you know, everything happens for a reason. We ended up selling a minority stake to this really cool company called Red Ventures, and we actually gave them an option to buy the rest of the business for, you guessed it, 9 figures. We literally like— because in my brain it was so clear that that's what I— that's— that was my mark I'd created for myself.

Yeah, you had to keep the dream alive.

I had to keep it. That's exactly what it was, right?

Yeah.

And the deal, that was kind of a cool deal, by the way, like, which is it was unique and maybe only very few companies would have done it. They bought, you know, a stake in the company, a 20-ish percent stake in the company. We gave them an option to buy the rest of the business at a nominal number, not a multiple. So normally you'd give an option to buy at a multiple.

Totally.

We said no nominal number. And the reason for that was it was a 2-year option and we wanted— we were going to behave as one company. So because they basically had all the incentive in the world to pump our EBITDA because they had a fixed price they could buy us back.

Totally.

And, you know, so we signed this deal, we celebrate the first—

and what year was that?

That was in late 2015.

Okay.

There were all kinds of other learnings along the way, but yeah, late, late 2015. And that was very close to an M&A style deal because they, you know, we'd done most of the paperwork and, you know, what immediately occurred to us like a few months after it, one, we made good money. And so that started this sort of reflection of like, what's the point of this and whatever, which we can talk about. But the bigger thing was we were tired. Like we had been grinding, you know, for 5 years. And we said— and now I said, now, now you have to change your business to try to fit the mold of this Red Ventures thing you did. And it was like, it was just for the first time I was like, I don't really want to do that. Like, I don't really want to do that. Right. And, and it was like we probably had our worst year ever in 2016.

At that point, were you regretting doing the deal or did you never regret it?

Hugely. I mean, Well, also because they were willing to buy the whole company, but I was so caught up on valuation and we did the deal.

I just— that was actually an option.

They would have bought the company full out. Multiple. We had multiple offers to sell the company, just not for the number that Jesse Pujji's ego wanted.

Right.

His 30-year-old ego is like, no, it has to be a bigger number, right? Yeah, I'm worth— I'm worth this. And you're wrong. All you people are wrong about what I'm worth, right? I didn't do coaching back then. I didn't know it. Like now I'd say if I'd felt my disappointment and sadness I probably would have made a clearer-headed decision. I just didn't. It wasn't a clear-headed decision. Right. And so, yeah, we regretted immediately. We had to— we fired a bunch of people the next year. We were one foot in, one foot out. So we were trying to convert our business model more like Red Ventures, but we weren't willing to fully commit because we were afraid that, you know, they had this option to buy us and they weren't being clear about it. And I, you know, I'd had a son. And I had a daughter on the way. Like, it was just— it was a time that was like the worst period of the whole—

So you had your son in that 2-year period?

I had the son, like my son, within months of closing the Red Ventures deal.

Oh my God.

And so, which was fine, by the way. I was like, oh, I'm a millionaire. Like, this is great. And I have a kid. This is the right time to do it, right? And but then like, then you become a parent of a young kid and, and I just— yeah, I wasn't feeling motivated. I wasn't feeling excited. The one silver lining was like the Rick and the Red Ventures guys. I mean, we— they were so Impressive. Like I said this, I think on Twitter, like I thought I was an 8 out of 10 business person. Then I met them and I was like, oh my God, I'm a 4 out of 10. And not in a mean way to myself or anyone. They're just, they're just genius. I mean, they're very smart. They're dialed in. They're extremely kind. Like they had found this, like, you know, as I said, like I worked at both McKinsey and Goldman and I would look at my bosses there and not in a mean way. Again, I just never wanted to be them.

Totally.

And Rick was the first person I'd worked with in my life Who I said, I want to be that guy.

Yeah, you saw that. You saw the perfect formula, right? You said it sounds like you saw the person who, like, on one hand had this side of your brain that can, like, do laps around people when it comes to analyzing deals and company strategy. Right. But then on this— but on the other side, someone who, like, so deeply exhibits, like, empathy for other people and actually cares about them. And to find that mix is extremely—

And is, like, so comfortable in his own skin. Yeah, right. And it's funny because I tell him these sometimes, like, man, I'm working on myself. He's like, well, you know, I was in a plane crash. I almost died. So I kind of have a cheat code. He's very gracious about it, right?

No, but it's true. It's true.

Yeah. So anyway, so we do that deal, you know, we really blew up the business. I mean, the original Ampush business was more or less gone by 2018. And this new business that we had created, that was— it was basically deeper, more involved partnerships, so on and so forth. We continue to run it. Business was growing. It was kind of coming back, but it was more volatile. And, you know, I got to 2019 and kind of there's something about hitting your 9-year anniversary at anything where you're like, oh, next year's 10. Like it causes you to reassess. And I had started coaching in 2017, '18. And one of the big things is like finding up the thing that really truly lights you, zone of genius.

Yeah.

And I, you know, I knew that I wanted my, my why that I talk about is wanting to help other people learn and grow to be the best versions of themselves and using entrepreneurship as a way of doing that. And so we did a lot of things inside of Ampush to do that. We invested in companies, we, we tried a lot, but we never quite got there. And so I think it just became clear that like I couldn't run Ampush as the CEO while also trying to like live that purpose. I just wasn't able— I tried it for multiple years and that's really what led me to go, okay, I'm ready to kind of transition out. And actually at first we were going to, we were going to use Ampush as a, as a holdco platform. It was generating a lot of cash flow and we were going to— what I've done at GatewayX, we were literally going to do a version of that at underneath Ampush because we had the cash.

And why didn't you?

You know what happened was so, so just to kind of memory lane, right? So transitioned out. We interviewed actually outside CEOs. We ended up selecting the head of our New York office to be CEO. He's awesome. He knew the culture. He was the, he was the one everyone wanted. People cheered when we announced it at the company-wide meeting. The company-wide meeting to announce it and our offsite was February 20th, 2020. You may know what happened a month later, right? The world shut down. Right. So all of a sudden the world shuts down. I was— I moved back to St. Louis after 10 years in the Bay. That was also part of my plan pre-COVID and a part of me stepping down and not being CEO. And we just took some time off. Nick and I took some time off and I think we got back together and basically between us two and then Red Ventures, who's an investor, and John, who is an important stakeholder, they're just— people didn't want to do that. There wasn't alignment around doing that. You know, he was running the company now. He was like, I need my cash. I want to, you know, manage it. Red Ventures was like, guys, I don't want to be Jesse's playground. And Nick was like, I'm tired. I want to take a little bit more of a break. And I was ready to get going. As you know, I took a little more time off. And so from that point forward, we essentially, you know, we ran it as sort of we were controlling shareholders, you know, Nick and I, meaning we ultimately called all the shots of what happened, but we tried to empower John.

You were the chairman at that point.

I was chairman. I mean, it's a pretty informal board.

Oh, yeah.

The board was me, Nick, and Red Ventures.

Yeah.

And then John was sort of like a tech— legally, technically wasn't a board member, but he behaved as one. Yeah. We'd meet once a quarter. You know, we were involved. I was still involved in helping drive a lot of business to the business, you know, to the business. I took most of 2020 off and then I started GatewayX in 2021. And so I was not super involved. There was different points where ebb and flowed. I was really supporting John. Whatever he needed me to do, I would do. Him and I had to recalibrate our relationship a ton because he was used to reporting to me.

Yep.

And now I was like, well, I kind of report to you now, John. Like, you're the CEO. That took him some time. He had to lead a business through COVID, which I wouldn't wish upon my worst enemy. I mean, and poor guy, like, he became CEO and COVID happened and it was tough on him.

Probably made him a 10 times better operator.

I'm sure. Yeah. And anyway, so We make it through that. We had a huge year during COVID We were actually down the next year, which was COVID. We had a bump we weren't expecting and then the business was back up in '22. And, you know, he, he at the beginning of '22 sort of said like, I need a change of scenery. I need different people around the table. You guys are kind of off doing your own thing. Red Ventures is no longer involved. Red Ventures was ready to be done with it too, right, from their perspective.

And wait, and by the way, I have to— I'd be— I have to ask about it because you talked about this timeline. What happened in 2017 when the 2-year option was up?

They didn't actually—

I mean, they just didn't exercise it and they kept their 20-something percent.

Yeah, they kept theirs as a minority owner. They had gone on to do a totally different business strategy, as most people know, buying all these content businesses. They weren't interested in a marketing services business anymore. And Yeah, but they've been— I mean, they've been great partners. So throughout all of that, they've been fantastic and always helpful whenever we needed them. But yeah, it's a tiny rounding error for their business. It's not like they were giving us their, you know, their resources.

Yeah. For context, by the way, for people listening who have never heard of Red Ventures, Red Ventures is like the biggest company you've never heard of. I think last I saw, you know, rough valuation on the business is like $12 billion. It's a massive company.

Yeah. And totally bootstrapped.

Yeah.

By the way, wow. And amazing people. But yeah, so, so that was kind of— John was like, I'm ready for a change of scenery. I want to get my team a win. He negotiated with us for incentives for his team. Like there was a lot of things that went on where he's like, I'm ready to kind of— and I think if he could have had his ultimate top choice, he probably would have had his own, like found a private equity partner and started to buy companies himself to like spread the Ambush culture. I think the Tenuti guys basically give him a version of that that's got a little more scale and capital. And what's really cool is they, you know, this was a proud moment for me. There's a, there's a, they're a huge company, but they have a team that's kind of competitive with Ampush and they're going to have that team kind of coming under reporting into John and they're like embracing the culture that we built and wanting to have that as a big part of what they're doing. So that was an awesome moment for him, awesome moment for me where we're like, cool, this is really a cool thing that we're doing. So anyway, That's kind of the whole, the long version of the story.

The 5-minute ambush update.

I love it. Exactly.

Okay. So that is— I think it's awesome foundation setting. And I want to go from that point you just finished on forward to talk about the deal. I think the first thing that I'm sure founders who are listening to this are wondering is like, how do you know when is the right time to sell? So it seems like in the context of your business, John, who was the CEO of the business, like he was ready for, for a change. Was that the primary driver for why you guys were looking to sell Ampush? Was there anything else contributing to it?

Yeah, I think it's a great question. I mean, you know, in 2015, I think what I'll say is I think most founders undervalue how important it is that they— it's a personal— it's such a personal choice. So in the case of John, I mean, John was like, hey guys, you know, we're going to sell this business or I might, you know, I need to— I need a change of scenery one way or the other, sort of. Right. That was kind of And we're best buddies and trust. So it wasn't like he was going to surprise us with anything, but he was also raising a flag going, guys, I'm— and that was the CEO version, professional CEO version of the founder version, which maybe happened to me in 2015, '16, which was like, I've worked really, really hard for a long time and I'm ready for something different. And I think like way too many founders who are great tacticians and try to get the answer right all the time go, what's the right time? Is it optimized? The valuation optimized, all these other things optimized. And with enough years under your belt, you realize that stuff is far less important than am I ready? And is it the right thing for the people in the company? And so I think in our case, it was— everybody was ready, you know, like it's— if it was going to be the holdco, we would have probably owned it for a really long time. But now that it wasn't, it no longer made sense. It was a huge asset in my portfolio that was like, you know, not diversified at all.

Yeah. And there's just that— there's, there's a feeling of like you don't have full sense of like control over your money.

Oh, for sure.

Yeah.

I mean, one of my friends in private equity, he says, look, we buy the business because it's a good business. And then the CEO, either back them or sack them. That's literally— and then at first I was like, damn, that's hardcore. Then I was like, well, no, that's actually the only thing I control is who's running the company and the company and what does the company do.

Yeah, that is exactly their incentive.

Yeah. And that's how we were. We were like essentially active private equity owners. We weren't going to get involved. There was a couple of instances where John and I got into it, which was rare. But it's because he expected me to show up more like a person who still worked there, and I was like, "Well, I've got a bunch of other things going on." Yeah. And and so him and I finally got on the same page about that, which was partly my fault. Like I was saying, "I'll do that for you," and then I would be late on it or something, you know. And and and then he'd go, "What the hell, Jesse? When you told me you're gonna do something you normally do," and I'm like, "Shit, you're right. I've got other things in my life." And totally. And so that was part of the you know.

Okay. So you got you got to this point where so it sounds like all of all of the founders. And then, and John were like ready for the next thing. So once you knew that you wanted to exit the business in some way, like, what do you do from there? Like, what is the process? Like, okay, I want to sell the company. What do you actually go and do?

Yeah, well, it's— it wasn't the best year in the history to sell a company.

Probably not.

So that is what it— I mean, you could consider timing. And again, like, people have pinged me since the deal and going, oh, what? What should I do? Should I, you know, especially guys who run marketing services businesses. And I've said, look, if you can, if you don't have to and if you're not in a rush, if you're not like, then hang on for another year or two because there's no reason not, you know, wait till the market's a little bit better. But in our case, you know, it's the best analogy. And, you know, this is kind of like, you know, selling your house. Okay. You decide and you're like, okay, let me make sure my carpets look clean. Am I, you know, repainting a little bit? And so there's a little bit of just like We did. We spent a lot of time in the beginning of '22, as an example, getting all of our most important customers into really long-term agreements. Right. So like these are going to be ironclad, multi-year agreements. And we may even gave up on price and certain things that we might have otherwise not done to get them into these contracts. Right. We made sure our best people were locked down and they were feeling excited about the year and incented appropriately. There was real tactical incentives handed out related to this, but I don't recommend actually normally, but In our case, it made sense. And then, yeah, we started, you know, whatever, paying attention to the business, spending more time with John. We started— our board meeting shifted to every 6 weeks. So we would start just paying, being closer to it, trying to drive things forward. And then we started meeting with bankers. And, you know, it was, it was interesting because it was a mixed bag. Like we had bankers who were like, I actually don't want to work with you guys. Like, I think you should wait. And we have other, we have other business. It wasn't like a, you know, slam dunk that everyone was like, oh yeah, this is the hottest deal on the planet. You know, I'm just being completely honest.

And one also, right, there are certain bankers like they won't think about working with a business unless it's at a certain size because it's not worth their time.

Yeah, there was, it was a combo of size growth, you know, market, current market conditions because, because, you know, they're doing their math of like bankers, for everyone's knowledge, they, they get paid on a success fee. So they're basically betting on their chances and ability for them to get you a deal good enough that you'll take it. And so some people just look at us and kind of go either they didn't think we were serious enough or they like they didn't think the market was right. They think, I don't know if I'm going to get you a deal and you're going to take that deal. I think I can get you a deal, but you may not accept that deal. And so they have to kind of balance all that out. And one of the big pieces of feedback they got was like, get a quarter or 2 of this year under your belt showing that your plan is going to work because, because of COVID was such a volatile period for the business, we needed to get— make it more stable. And so by Q2 or so, John was beating his plan and we started, you know, talking to more folks and started working with a banker. And, you know, by the way, just another thing is you're not, first of all, too small for like Morgan Stanley or some big company, but you go typically find a banker who knows your space and sector really well. Did you guys use a banker?

Yeah, we did. And we use like a boutique guy who he was— he ran corporate development at IAC, the big media.

Exactly right. So we use a firm called Palazzo. They had been previously at other media-related firms. Like, they knew this space really well, right? They could talk to us about our business, what the buyers wanted. And, you know, when we ran the Red Ventures process, we didn't use a banker. And I actually think it was a mistake. It was, again, me and my ego being like, I can get us a deal. And I did get us the deals.

But yeah, it's not worth paying them the fee. I can just like—

exactly what I said in 2015. Yeah. And the work part of it is okay. I think there's a lot of leverage and I think they can say things and do things you can do that 100% you can't do in a buying and selling selling process and they help create leverage. They make everyone behave more seriously, which if it's just me swashbuckling, like they're like, oh, we'll call you next week. There's a banker there like, this thing is happening. So if you either want it, you get involved. So that helps create leverage of multiple parties getting—

I feel like it's also just hard for you to be a hard-nosed negotiator with the company that you're going to then be in bed with after they buy you.

Exactly. So there's, there's a lot of value there. We started marketing it in late August. It was pretty fast, honestly. And I think, I think there were, you know, things moved very quickly. So late, late August, we were a known quantity. That helped. We'd been around forever. Right. So it's not like no one was wondering who's this random company. It's been around 13 years. Right. And, and so they knew us. So we went in and had a lot of conversations. I think, you know, there were a handful of interested parties who got serious and put together like written terms to actually give us real things. And then I think the folks at Junior New Mountain, they wanted the business. They were pretty— they moved fast and pretty aggressively. And again, just like when you're selling your house, yeah, maybe this other guy's offering you a little more money, but you're not sure they're going to have the cash in their bank account or there's other issues you have to kind of sort through. And then there's one guy who goes, I'll buy it all next week and all cash, right? And so that's another big thing founders forget is certainty of close.

Yeah.

Is the person going to actually get the deal done right? And there was a whole span of— there's PE firms, there's— these guys were backed by a bigger PE firm. There's like random founder-led companies that There was a public company, like there's all these different kinds of companies and you're like, ooh, who's going to be the best? What's the best fit? You know, it's also in our case, unlike a lot of cases where you're the founder CEO, we weren't going with the business. So we were a little bit— we were like, get the deal done, get the right numbers, what kind of economics are coming to us? But we also carved a lot out for John to go, hey man, you're going to— you decide. And almost explicitly had an agreement with him of we will accept— I think, I think I said 15%. I'll accept a 15% discount on mine. in exchange for you choosing the right partner for you, right? Like, I don't want you— I don't want to sell you down the river. Totally.

And I also feel like there's an aspect to it of like, you know, it makes sense to optimize for your economics, but also like you've built this thing over the last 13 years. Like, it'd be a shame to 5 years from now just see the company be a shell of itself.

Totally, totally. Yeah. And I think like one of the other many benefits of that Red Ventures deal was I'd had enough of a taste of making money to realize money is not everything. When I was 30, before I'd had that, I thought it was everything, which is why I thought, you know, 9-figure valuation versus a high 8-figure was different. It's just my brain had never processed that stuff before. So, so yeah, we were, we were under terms with them on November 1st. So September, October was taking pitch meetings, lots of different companies going back and forth, going deeper in the numbers, getting LOIs. They moved pretty aggressively and we weren't going to slow them down.

How early in the process did you tell these So your banker talking to a lot of these different firms, how early in the process do you give— do they get an indication of like the price that would be required or the terms that would be required to get a deal done? Like how early are expectations set?

Never. We never gave pricing guidance because why would you do it? I mean, you know, someone comes in like, why would you signal? Why signal unless you need— I mean, you can as you get closer to someone, if someone's late to the party, which happened in our case, we gave— you give them a number and they're kind of like, It'd take me a few weeks.

I got to get basically to just fast-track them.

Yeah. Well, once you have a real written offer in your hand from a serious party or a few, right, then, then the leverage flips very quickly. First, you're like, get everyone to fall in love with me. Oh, a few people have fallen in love with me. Okay, now I get to pick and I can call the other parties and go, here's the number if you want to get involved.

Yeah. Now you're like, let me shop this in.

It's like getting a job, right? You go around interviewing for a job and you make sure you put your best pair of shoes on and you tell your story and then you get 3 job offers and you get to start digging. So that's kind of what that process feels like.

Got it.

In our case, there was a lot of alignment on our side again because it meant different things for different people. And that was a really important part of this. And then, yeah, the closing process went, you know, closed on January 4th so that we was, you know, I was pretty impressed with everyone. We got done in 63 days or whatever. And it was, it was a bear.

I mean, for context, that like Jesse's— so the process from beginning to end How long was that process for you? From when you hired your banker to close?

August to January.

Yeah.

So just like on the fastest path, especially in this market.

Just for folks who, you know, haven't been part of an M&A process, haven't sold their business, that is incredibly fast. Like I would say, you know, for Morning Brew, our sale process was 11 months. It's definitely on the longer side. That was like in the thick of COVID which is why things were slowed down. But, you know, 4 and change months is like crazy fast.

Yeah. So yeah, I think it's like 6 to 12 is normally what they'll say and what I would tell people also. I think ours, the couple of things that demonstrated was like, again, we're a known quantity. So like, you know, and you build— if you're in multiple— if you're in year 4 or 5 and thinking about this, like build relationships now so that by the time you have those conversations, you're a known quantity. I think the other big thing was When there's a strategic need, like when you fit in someone else's glove or whatever the glove like it is, it just there wasn't a lot of it was clear that they needed it more than they wanted it more than anyone. They, you know, all that, that stuff was and boom. So they went and got it done and they and I will say, by the way, because I think it's important, they're buying other businesses. They were amazing throughout that process. That's another thing that founders don't realize. I made that mistake when we divested the EDU Business. I took the highest bidder, and they're—and I'll say it publicly—they were scumbags. They retraded the deal. They kept adding time to the deal. You know, they had—they knew they had leverage. I was building the social business back in 2013, 2012, and—and you know, they fucked us at every opportunity they got. This other—this was back in 2013. These guys couldn't have been more different. Yeah, there was an issue that popped up. Hey guys, we're going to work through this with you. Oh hey, what's going on with this client? They changed around when they're spending their money. No problem. We get your business. We're going to work with you. They— no retreat. No, I mean, they were— they did exactly what they said they were going to do. And the reason I'm calling it out is because it's rare. It's actually—

Oh, yeah. Most people do. Most people do not act in good faith when they're buying or selling companies.

Well, the buying especially, because remember, once you sign, just so everyone knows, you sign on November 1st, we signed, they have exclusivity over, over us. We cannot talk to anybody else. That's one of the binding requirements. So if you're a buyer, you get someone in and then you go, oh, you know what, we looked at the company. We thought it was worth this. We actually think it's worth 20% less. That's a very common occurrence. And I thought that they, if they wanted to, they could have done stuff like that to us. They could have picked at things. Yeah. And that's just not how they behaved. And I thought I was like, I was very happy with the way that they all behaved during the process and very collaboratively.

I have one last question for you about the process, and then I want us to finish this episode talking about what it was personally like for you. Around the process, tell me for you what you have all these different variables that are involved in a deal. You have what amount is cash versus equity? How much are you getting today versus in the future and how long, how far in the future? Who is the partner? What is their goal with why they're acquiring us and how much autonomy will we have? How much will be our vision versus their vision? I'm sure there are other things. that also go into the process. How did you in your, in your head prioritize these different variables and what did you optimize for?

Yeah, I think the number one thing for me was cash at close for me and my family. You know, I wasn't running the business anymore. I don't control a lot of what's going to happen if there's an earnout or anything else like that. And so I was like, all right, like, what am I taking home when this thing closes? What am I giving up? And one funny surprise, by the way, in the process, it's yours. You know, the previous time I'd done this, like lawyers and accountants, they all obviously turned to me. I was the CEO and the founder. Now I was not. And one funny thing that happened that was like, it made sense to me later on was they, the, the lawyers and accountants kept coming to me and Nick for every decision. And actually they left it with one of their jokes and we were doing like superlatives at the end of the deal. And one of our jokes was John was the most left-off person of emails and it was actually kind of crazy, like, but it did reinforce the importance of ownership to me, which was as a matter of course. And the bankers too, they came to us, they go, you're the owners, what do you want to do here? And that was like, whoa, that's, you know, and so that was an interesting aside. But cash flows, I think number 2 was, you know, was the team going to be taken care of both financially as well as a good Good culture. Are they going to preserve that? Are they going to build on that? That was super important to me on the margin, you know, relative to cash. Once we had hit a certain number, I think those are probably the two. Okay. And I mean, yeah, it's different when you're going with the company, right? Then you have your comp plan and your earnout timeline and all these other things. I coached John a lot through that, by the way. Like I helped him negotiate those things.

Well, just speaking about negotiation for a sec, what was— what's your negotiation style in these types of conversations? And talk for a second about the, the interesting clause you negotiated around if you died.

Yeah, but that was a different deal. That was— that was a money fundraise. Yeah. Oh, what? I can bring that up. But the, the, you know, one funny thing that happened to me during this deal was I remember feeling very uncomfortable in the middle of it. And not knowing why and not knowing what to do about it. And the reason I realized later, because later on, you know, typically when I negotiate with someone, I have built a relationship with them. I have a lot of trust. I'm the kind of person who's on text or can just give them a phone call and say, hey, you know, let's problem solve this together. Like, I like to— I believe in collaboration and problem solving. And like, I always believe 1+ 1 can equal 3 if you're creative enough. and you're sort of, you know, you're not coming from a place of fear. I had no relationship with the other party up until really the last couple of weeks of this. They had met John. He pitched the business. He was going with the deal. And, you know, he, you know, he obviously cared about his own economics. He cared about ours, too, of course, but not in the same way. And so there were a handful of like silly things. There was like the date moving. There was a few big items that felt very serious at the time. And I couldn't pick up the phone and just call Zach, their CEO, and go, hey, man, Help me. And I didn't have that actual trust with the other and with the other person. And that was super uncomfortable for me. And even like that, I remember the term sheet was like pretty back and forth. It wasn't normally how I would do it, which is like I would get on the phone and go, what's really important to you guys? Here's what's really important to us. Let's put this on a page. Let's find the Venn diagram and let's find a deal we're both really, really excited about. And so we got there. I mean, the deal ultimately happened that way, but that was a really good learning for myself. I was talking to my coach after, like, man, I felt Like I was entering into this hugely important thing for my life. I knew you didn't have control. One hand tied behind my back. Yeah, but reflecting on it, there's no reason I couldn't have asserted that. I just didn't. It's not like— like I could have said, hey, hold on, before I sign this thing, I would like to meet these people and like get to know them a little bit. And like there was a call, there was like a very serious call with 30 Zooms and lawyers and all these people on right towards the tail end where we had to sort through the final, final issues of the agreement. Right. There's like What's this going to work and how's the non-compete and all these things? And I ended up— I realized it right after that call because I ended up leading that call from our side for a variety of reasons. And I was joking with their, their private equity guys and their CEO. I'm like, guys, you want, you want to tie me down for so many years? Like, and then I realized I was like, oh, I'm really good at that. Like, that's a skill I have and I haven't been able to use it up until now.

Yeah, your banter is incredible tool.

Yeah, but it's like trust building. It's not taking yourself too seriously. There's all these pieces that go into a good deal. Yeah, like most of them I didn't get to use during, during the process. And towards the end I did a little bit because there was a few final things, but, and I was like, shit, like that's a good learning for me. And I could have just, I could have had that from much earlier on. And why don't I negotiate? That was problem solving.

So do you think, do you think the reason that you didn't engage like the CEO of the business that bought you directly because you were afraid of stepping on John's toes? Like what was the reason that you didn't do what you could have?

I'm a beginner. Like I've never been the chairman founder, but not the CEO of a business. I like, I didn't, you know, I just didn't know what to do, I'd say. And I think part of it was like it was John's thing and I didn't, I didn't want to create conflicting signals. And I didn't, you know, it was just like, let him lead. There was bankers also. We asked the bankers, you don't need to do that. It's not a big deal, which they're probably right. I mean, the deal got done. It wasn't. But for me, I think I would have, I would have felt more comfortable and been better if I had some line into someone on the other side, which I just didn't really.

Yeah, it's so interesting. It's also interesting to think about, right? Like you mentioned with the term sheet, it's not the process you would have run, but like still worked itself out, which is just an interesting thing. And just seeing like—

I bet you it would have gotten done if I disappeared for— if I was in the hospital for 90 days and couldn't talk to anybody, I would have just had this check show up in my bank account.

Yeah. So interesting. Okay, we're going to get into the, the internal stuff. If you had to— you think about the journey from August to deal close or even to today, from beginning to end. I want you to just start pointing out to me specific emotions that, you know, you felt in this process and when you felt them and kind of why you think you felt them and just bring up any emotion that comes to mind first.

Yeah, I've had so many, man. I think like I felt some fear early on and John would call me out on it because, you know, he's never sold a company, never pitched like buyers or investors. And I have and I'm pretty good at it. And so I felt fear early on or I was like a little micromanaging towards him that it like we even— we almost got an unsolicited offer earlier in the year. And I was just like freaking out. I was like, oh wait, make sure you don't say this, do this, say this. Like there's just a bunch to manage around it. And I sort of not, not probably not my most, the best version of myself that was like, I remember that feeling. There was, I can't talk about it, but there was one buyer in the process who was like such a cool buyer, like such a well-known brand name company and You know, I don't think they were the right buyer, but but they it would. I felt a lot of pride that they took a long, hard look at the company. I felt really, really like that's that's super. You felt like a badass. Yeah, I felt like a badass and proud of the culture and proud that it like it wasn't like they took a look and like ah we're good. They they spent you know hours days with the team and were waffling and and half the people who didn't do the deal call me and say oh we should have done this you know. So it was like, it was a cool one.

That's awesome.

At some point I'll share it. And that was pride. I think like a ton of excitement and gratitude for John and the team when, when we signed the term sheet because, you know, that's, as you know from the process, like that's the moment it really gets real, you know, like it's at that point you're 80% to close, right? You're very likely. And so I felt a lot of pride. At that point, there was a lot of fun during the process. So we like our— my long-term VP of finance and HR became the COO of Ampush. Then she actually left. She left like a year and a half ago. She went to be the CEO of another startup, didn't work out. And then we convinced her to come back to help lead this deal.

That's awesome.

So she was back and then me, Nick, and John, and we were like, it was very Last Dance vibes. Like, it was like, this is it. We're calling each other, we're texting, we're figuring it out. Like, there was— it was just fun. It was like really fun. I also felt a lot of gratitude for the people like Kahani Growth Assistant. Like they were, you know, they were helping me. It took a lot of my time and more than my time. It took a lot of my like mindshare for somewhat obvious reasons. There was a couple of like periods of frustration, like the biggest one, again, in retrospect is not a big deal, but you just— these things are so tense, right? Like we were ready to close the deal and they said, let's close the deal in December, such and such date. And then like 3 days later they said, never mind, we want to close in early January. And we just— it was fear and frustration. Like, what? What? What do you mean? Are they looking at another deal?

You were just ready. You were just ready for it to be done.

Well, it was just— well, no, it was more fear. Like, are they giving themselves optionality to look at a different deal? Are they— are they cooling out? Are they like, what's going on? You don't really know. And it's like I called my buddies in private equity. I go, this is what happened. And they weren't reassuring at all. They were like, yes, it could be. It could be the reason they're saying. It could be they just need more time and they don't want it to show up in their financials for a year, which is like the stated reason they want to give more time to communicate it internally. So very reasonable reasons. It could also be they found another deal they like more. It could also be this. And these private equity— I'm like, fuck, this is scary. Like, what? We've spent so much time and energy on this. There's a lot of fear there.

It's also just such a good illustration of like when, when you are feeling fearful in any of these scenarios, it's amazing how good our brains are at at storymaking and also how often the majority of the time the simplest story is the answer. But like how good we are at creating stories that are— go to the extremes of painfulness.

It's also, by the way, back to my whole thing of not having a line into the other side and not having trust built. It also for me was a signal that was lacking because again, when I've done deals in the past, if I actually have human trust with another person and he goes, you wouldn't worry about it, I get it. You feel a little worried, like On my honor. And I could even— I would— I'm, by the way, I'm a very candid person and I'm very okay asking uncomfortable questions. So I'd be like, dude, are you guys looking at someone else? I would have that conversation with the other side normally. Right. But you didn't.

You couldn't do that.

There's a CEO, like, you know, there's all these other people there and it made it harder for me to. But it was a good— it was a good point out. You know, we signed the deal. We did what's called a split sign and close. I think I told you this offline, but like, so we signed on the 21st of December and we closed on the 4th. So imagine the most like anticipatory two weeks of your life. The deal is done.

Like all this. I don't know if we're going to run this, but this is the M&A version of blue balls.

Yeah, I didn't want to say that, but yes, it's just like, oh my God, is it going to like it's going to happen? It's like, yeah, you know, and then your family, like nobody knows. You should congratulate you. Like when I was like, that's not close. And my dad's like a real estate guy, so he's like, you don't. You stay on this every day until, like, you know, it's not done until the money's in the bank. Like, so there's all these, like, it's just like sitting there. And that was like, it's just a highly anticipation-oriented period. It kind of like just preoccupied, you know, every day is preoccupied. And then I flew up to New York for the deal to actually close. And that was like the night before me, John, and Nick got dinner and there was just like tons of appreciation and gratitude and You know, their wives came and there was just, just like really— I think, you know, one of the things I'm proudest of us as a group is this is something my coach really introduced. He's like, you know, typically when you go through like a salary negotiation with someone or a challenging situation, like everyone basically prices in that you're going to hurt your trust with that person a little bit. I'm going to piss them off a little bit, but we'll get to a place. He's always like, no, how do you get your trust to go higher through a process like that? Yeah. How do you love each other more and trust each other more? And actually, when you reframe it that way, You do things very differently, and so that was like I felt like we all came out of it feeling more gratitude and love for each other. You know, there was a really interesting well actually, I think it happened around then. Like there was like it was weird for me and strange I'd call it, and maybe feeling like I just being totally candid, like a little bit underacknowledged or lost in the process because I was I'm just so used to being the man, like the guy in the middle. Like when Jesse he's Jesse Pujji, he's this guy, he's going to be the guy everybody falls in love with. and nobody gave a shit about me. I was just like shareholder A to like, just John was the man and the team, you know, which by the way I love. But there was a part of me that was like, well, what about me? You know, like there was definitely a part of me—

That's very rational.

That wanted, yeah, that wanted the glory of, of, and then part of also the glory of like, hey, I ran this business for 10 years.

Yeah.

And this guy, you know, these guys ran for like, I, you know, what about me? I built this thing. So there was definitely a little bit of that and wanting, and ultimately came from, I think from Nick and John of just saying like, Acknowledging me going, yeah, like, dude, we know, we know that you were critical to this. But it was definitely— that was a feeling as we got towards the end of like, you know, of wanting to be acknowledged or wanting to be— get some credit for it, which is hard to admit, but true.

No. And I think it's such a natural thing. I'm just curious if you can, from your perspective, identify why you want that validation. Like, what do you think was the root of like why you want to be recognized for that?

I don't know. That's a good question. I mean, I think I worked my ass off for it.

Yeah.

I think I feel like I, you know, one of the downsides of the 3 co-founders structure from early on was always like we were the founders. And I think like, yeah, at different times I felt like I was— without me it couldn't happen. And I wanted someone to say that. I don't know, just like wanting to see, be seen, maybe.

I feel like anybody wants that. I can imagine also, like, again, this, this identity for you as an entrepreneur and a business builder is like so core to who you are. Yeah. If there's anything—

well, and Ampush was so core to who I— I mean, I think I wore t-shirts publicly like, like some founders do for 5 years. I mean, if you saw me externally at a conference, I had an Ampush t-shirt on. Totally. And I remember I hadn't worn one during that, like, post-CEO phase as a part of changing that. And then I was like, wait a second, like, This is, you know, the other funny thing that happened to me, Alex. I don't know if I told you about this, but like, you know, I stopped being CEO and I left San Francisco in the middle of COVID And so there was never the party. There was never both personal and business party of goodbye, Jesse. There was never— there was like an all hands on Zoom or something.

It was more like the Irish exit of running a company.

So I felt there was like this missing closure. And then I'd say, I think as the deal got done, the day the wire got sent, I felt like a crazy amount of probably anticipation because it takes whatever, 6 hours. Like, I was like, I'm not— I can't feel happy. Like, I just don't feel it yet. I don't feel it yet.

And were you constantly checking for those 6 hours your bank account?

Texting people like the bankers in the middle of it wrote us a note like, hey, did you guys get your wire? I'm like, wait, does that mean you got yours? Like, you got paid before? Like, so there's like this funny process, like, where's the money? You know? And like, my dad wouldn't call me until he confirmed I got the money. Like he's like, did you get the money? And then as soon as I was like, yes, he's like, you know, like, so there's like that day of— but then were you—

where were you with your family? Like, were you with your wife and kids? I can't—

well, so I'll tell you, it's a great story. So I was with Nick and his family in the morning because I was in New York. We did the phone call where you're like, signatures approved, blah, blah, blah. The money is being sent. Him and I took a long walk in Brooklyn and did a lot of reflecting and sort of just like appreciation acknowledgments for each other. But it felt He was like, dude, are you okay? Like, I was like, because I just wasn't fully there yet. I was like waiting for it. And then I went and got lunch with the private equity partner from the firm who bought it. And then it finally hit that afternoon. Then I was like, oh, let's go. Like that. Like it was— I felt the release, physical release. And then I flew home that night and my wife, the kids were all decked out in ambush gear and they had like music playing when I walked in. So they were so excited and so happy about it. And it's really You know, one really cool part about it is like it would have been cool to sell the company in 2015. It was so cool to share it with them, and they're both old enough now to like actually be like, "Oh, I know that like that means something really big." Yeah, and that would have to feel excited for you. Excited for me to see it happen, to understand what that means. Like the funny thing was when I first told when we first got under LOI, I told my son, "I'm like we're selling Ampush," and he got upset. He's like, "No, don't sell it. You're the founding father." He calls me like, "You're the founding father of Ampush. Don't." You can't. That's your company. What do you mean you can't give it to someone? Like, he was really upset by it. And then I'd say like a big crash of sadness happened on that day. Like, we sold it. Like, it's the first time Nick and I don't have anything we're working on together in 20 years. And I think it hit both of us. He was crying. I was crying. Like, it was—

And are you a crier? Like, do you cry often?

No, not a huge one, but I do. Yeah. And no, it hit me. I mean, it hit me big time. And I think like even it's a little surreal of it not being ours anymore. It's been such a big part of my life for so long. So it was like kind of like feeling a little bit like feeling for your cell phone and it's not there anymore or whatever. Like there was that feeling of it just being a normal part of things. I'm still in a couple of the Slack joint channels, so I'm like, hi guys, I'm still here. I said, I miss you, them the other day. And there's like a business development channel. I was like, I miss you guys.

So funny.

But yeah, it was sadness. And then, and then I think like a huge way that one of the coolest things that happened was the next couple of days and that happened again this week. 2 days after the deal, we announced it to the employees and former employees because they were all getting paid. Right. And then it was like I felt tons of gratitude, but we got barraged with messages. So I should— we should share some of them. But I was like, I'm so glad I started my career there. You guys changed everything. I'm so happy for you. I know this is what you like. There was hundreds. I mean, we had a huge alumni base and all these people pouring in. And then the external version of it happened this week when we announced it publicly, which was like, oh my God, these people I haven't talked to in 5 years and people who bet on us early, you know, like there's a lot of humanness involved in this. I started when I was 25. It's insane, right? And now I'm like, I'm 38. And so there was like— and I don't think there was ever a proper moment to go reflect on the whole huge journey. And now that moment is here. And so it's been really great to have that. But a lot of gratitude, a lot of gratitude for my wife.

Like, well, I was going to say, you, you wrote an awesome Twitter thread that we should link to in the show notes. And honestly, I feel like that could be an episode in itself because you had all these lessons in that thread, but you finished your thread. The last tweet was about thanking your wife and having gratitude for her. You know, just talk about for a second because I feel like it goes underappreciated sometimes. Kind of like the level of just sacrifice and support that any partner, life partner, has to provide to another partner who is an entrepreneur and has their own business. Just talk about that for a sec.

Yeah, it's a— yeah, it's a superhuman level of, of, you know, appreciation, support, tolerance. That's a word that comes in some ways. Like, it's, you know, the best analogy I was like, it's like imagine training for an Olympic sport I feel like people can visualize what that looks like. You're up early in the morning, you're home late at night. Your diet is unique. You're— you have to do certain things on the weekends you otherwise wouldn't have to do. You're— it's hard to be mentally present. You know, I had, you know, my EQ has grown as I've grown, but I had no EQ in the first 5 years. So, you know, wasn't— wasn't open to— like, so, yeah, I mean, I think— I think it's— it takes a lot to, to, as a person, in some ways take a backseat to somebody else's thing. Right? Like knowing like you're late to something, you're going to cancel something. And even just being in that status with another person, I think it's obviously unfair in retrospect, but like that's the status. The status is something, something for your business comes up that's important. I'm going to— my thing is going to get deprioritized. And I think I got much better at it after we had kids. But those first 5 years, I mean, you know, it was— I was, I was working a ton and I was mentally— when I wasn't working, I was mentally not fully there. And she's still here, so she didn't have to be. You know, I mean, like, and she was supportive of that. And yeah, I think it's one of the most unseen roles in any kind of success like this. And I'm even now we're still unpacking sort of, you know, my appreciation, gratitude, the things I didn't even know I know I was feeling or know that I needed that I was getting from that. And Yeah, it's a big one. Yeah.

And I like how you just talked about it in retrospect of being unfair. It's like I almost view it as like, you know, the— a partner to an entrepreneur is like so beautiful in the fact that they're signing up for ground rules that are unfair ground rules, yet they're still doing it and they're doing it unapologetically, which is amazing.

And the other crazy thing I think we don't say enough is No, if you're not doing it, you have no idea what it feels like or what it's— what the person's going through. So they do it not— I don't mean this in a negative way. They don't have an understanding or empathy because they can't. It's hard to know. And yet they're still doing it.

Yeah.

So it's like, I'm going to support you. It's almost parental, right? Like, I'm going to support you even though I have no idea what that's like. I don't even know what you're feeling or going through, but I'm still going to somehow choose to support you. That takes a big person. You know, it takes a lot of 100% and a big heart.

Well, I think the tape's been running for like over an hour, and I feel like we could go for another hour. But given our other episodes are 15 to 40 minutes, if you've made it to this point in the episode, just shoot us an email at thecrazyones@morningbrew.com. I just am so interested in how many people made it to this exact spot. Seriously, thecrazyones@morningbrew.com. Just say hi. I want to see how many people got to this spot. But we're going to finish up with some rapid fire. I have a few fun questions for you and then we'll call it a night. First question is, do you feel more successful today than before the deal closed? Yes. Why?

You know, I thought back in 2014, like the having the stamp as an exited entrepreneur, successful entrepreneur would matter a lot. And then for many years I was like, it doesn't matter, doesn't matter, doesn't matter. You know, Rick, Rick is this guy I really admire and he doesn't— he's not exited. He's been running his business for— and I think there is something to it. Like, I think getting it across the finish line matters to the world, like people, the way you're treated, the way kind of that success. And I think I'm getting used to this amount of cash, but like there is something unique about it and getting to plan and think for the future or feeling very secure and safe in the family. You know, I had that to some degree before, but now it's like really there and it's like I get, you know, luxury example maybe thinking about is like I was talking to my buddy the other day about like, could we start something that would like be here in 100 years? And I just have never thought that way before. Never like thought I could think that way. Totally.

Second question, have you made a fuck you money purchase yet or are you thinking about it?

I think you know the answer to this question. I'm fine. I know that you're thinking about it.

But, but I will say that Jesse is always judicious about his finances. And so it is a car that there will be tax benefits of buying.

Yes. I will write off the entirety of this week's large purchase price. And I got the dealer to come down $23,000 by calling around. I called around the country and I found— I created some leverage. So there we go.

Yeah, you're going to be— you're going to be the grandpa that's going gas station to gas station when you're older, seeing which one's selling a gallon for a penny less. My grandpa does that. Next question is, have you thought about how you raise and support your children in a way that they have the hunger that you had as a child, given that you have money now that can lead to entitlement? Hmm. I've definitely thought about it.

I don't know that I have. Any genius answers to it. I mean, I think I'd love for them to have the motivation. I mean, I've spent a lot of time on motivation, but I'd love to have for them to have as much or more motivation than me. But I think one of the issues with the premise of that question is like my motivation came from like maybe seeing hard immigrant parents. And we talk a lot about the fear motivation or the chip on the shoulder being the driver versus a like love or desire-oriented motivation where you're actually trying to go do something interesting and compelling. And so in my perfect world, they'd be more motivated or as motivated, but from a different place. My son is very inventive. He comes— I mean, he created like a widget toy the other day with Legos. He and I want him to be able to pursue that with reckless abandon because he likes it and he wants it, not because he has to or not because he feels the need to make money. And I think he will ultimately. But I think— and my daughter's insanely creative. I mean, she tells entertaining stories at the age of 5 that, you know, And so like, I want her to be able to pursue that, assuming that's what they choose and want to pursue as people.

Totally.

So I want them to be motivated to be— I want them to be enabled and motivated to do great things because they want to and they're drawn, you know, they're drawn to it. Not because— not in my opinion. My reasons were like, I wanted to be rich because I like, you know, I saw my parents struggle and wanted to be a business baller. Like it was just a very different motivator, is a different motivator. I think I think the biggest thing is like you know there's not like some of the thoughts in my mind is like I'm not there's not going to be a lot of free money given between me and them. I don't just mean when they you know when I die, which is also probably not going to happen. But you know like they'll if they get allowances, they'll do chores for them. If I'll expect if they want to spend money on random shit, I want them just like I did to get an hourly job. I think an hourly job when you're fifteen or sixteen is One of the great balancers, right? Yeah. So I don't think there will not be a lot of like, here's your credit card, you have a budget and allow like that. That, that just won't happen regardless. Yeah.

They're going to work for what they earn. Yeah, exactly. Yeah. Makes sense. Well, it sounds like kind of the North Star there is very clear and you want them to feel this love-based motivation for the things they do as you get a better sense of like the tools and the language you use in your life to try to guide them towards there. I'd love to do an episode where we kind of really unpack what is the playbook, because I, you know, not that it's a very common challenge, but I think it is a very real challenge for a group of people that, that experience it. Last question for you, and then I promise we're done. What's next?

Yeah, one of the benefits of the way we did this for us was Nick and I acknowledged this was like we thought about selling the business in 2020 when we decided to come out of it. And we probably, you know, we would have just been finishing an earnout right now or something like that. And instead we kind of got the benefit of we took time off and then we've both of us have started new things and we're working on new projects. So I have my hands full with all the stuff I've gotten going, which, which, you know, multiple— 3 companies have started, the venture studio. There is a part of me even before closing the deal who wanted to reduce the time on my calendar a bit. You know, we've talked about my schedule and bring that down a little bit. And so I think that still holds a little bit. I'm curious to see. I'm like not trying to overcontrol how I will respond and react to this at the moment. I'm like, no, this is— I'm building Kahani and there's this going on and, you know, these things are getting off the ground. I have— I still want to build this venture studio. I still want to work every day and build some cool— something really cool that I'm really proud of. I, I suspect there will be some edits and adjustments as I go. You know, one example is like, can I use some of my talent and capital to build again something that's just for the benefit of humanity versus making more money? Like, that's again a question I don't think I would have even asked a month or two ago. I told my coach, I was like, I think I will do things less because I feel like I have to and more because I want to. And I don't mean that in a big way because I think in a big way I'm doing what I want to. But I mean, like, like I'm the key sales rep for Kahani right now.

Right.

Like, I take the sales calls and I like it to a degree. But it's like, you know what, like maybe we should hire a person to do that so I could get like 7 hours back on my calendar. You know, it's like there's stuff like that where I think I'm doing them from the more foundry need to get this done thing that I think I'll probably have less tolerance for. I love it.

Well, you know, I'm incredibly appreciative for you walking through the journey and also kind of what the, what the emotional experience was for the 13 years that was building the business and the reflection on selling it. Because, I mean, I think you painted such a good picture of kind of this rainbow of emotions that founders experience. And I hope our listeners found it valuable. And, you know, I know as, you know, a friend and I look to you as a mentor, I've learned so much just from your process of building your businesses and, you know, just another notch on the belt. And I know there's many more to come.

Yeah, thank you. You know, the one thing I'd end on is with the benefit of this many years and this kind of view of hindsight, the people are really the only thing that preserved through any of these things. And of all walks in life, like our biggest clients are, you know, who at one point took the business in-house and churned, they're still my friends. You know, some of our employees, like a lot of our employees, Part I've been going back and forth with all the partner managers at Facebook who got us to be in the special program. Like those relationships endure beyond any of this stuff, and it's just a reminder to everybody and myself of like that's also why they should be the most prized and prioritized part of any of these things. But it's so true. Like it's just none ambush doesn't matter anymore technically to me, right? The numbers don't matter. The none of it—it's not mine anymore. But all of these relationships and people. Are very much a part of my life. And it's just a really important thing to remember for anyone listening.

100%. And on that very similar note, if you are a listener that is still listening to this episode after an hour and 15 minutes of us bantering about the journey that Jesse's experienced over the last 13 years, we thank you. And I just have one last ask of you before Before you sign off for the day and wait until next week's episode of The Crazy Ones, and that is shoot us an email at thecrazyones@morningbrew.com and just say congratulations to Jesse. I want to see how many congrats we get for for Jesse because what he's accomplished is awesome, and it'd also be cool to just meet more people in our community, see how many more crazies there are out there. Thanks everyone for listening.