#106 Kass and Mike Lazerow— Serial Married Founders Sold their Company to Salesforce for $750M on Loving the Journey (Encore)

Who you pick as a co-founder is more important, I think, in many ways than what you decide to do. You could always pivot the business. It's very hard to pivot a co-founder.

Yeah.

It's where people's misery comes from.

Yes.

They pick the wrong partner.

Oh, big time.

And then when you pick the wrong partner, you don't perform at work. And now you're like miserable at home. You're poor, depressed. Like, that stresses me out.

Welcome back.

This is From Startup to Grownup. My name is Alisa Cohn, and today I'm thrilled to welcome a dynamic duo to the podcast, Kaz and Mike Lazzaro. Kaz and Mike are the husband and wife team who built Buddy Media and sold it to Salesforce for $750 million, all while keeping a strong marriage and raising 3 kids. A pretty amazing feat. In addition to being serial entrepreneurs, Mike and Kaz are also angel investors who have invested in a lot of companies, including Scopely, which was sold Golds for $5 billion, and the super popular water company Liquid Death. They've now codified their startup success playbook in their new book with the edgy title, Shoveling Shit: A Love Story. We cover a lot of ground in this discussion, including what they did when the acquisition of their first company totally blew up, and the exact words that Kaz used to let the team know she might not be able to pay them. And why everybody stayed with them despite that. That led to a discussion of culture, specifically how to build a winning culture and the tactics that they use that go against conventional wisdom. We also talked about the importance of the pivot. Mike said they love throwing stuff away. Now, it's not so easy to step away from the things you've invested a lot of time and energy in. So we covered how they did that, how they do that regularly, along with their specific framework they use to assess if a startup will be successful. Obviously, we talked about how they maintained their co-founder relationship and their marriage, and also about Mike's blowup with a different co-founder and what he learned from that. There's a ton to learn in this conversation if you're a founder, a leader, or a spouse yourself. So please enjoy my great conversation with Cas and Mike Lazzaro. Cas and Mike, welcome to the show. I'm so excited to have you here.

Thank you for having us.

I'm super— I can't wait to sort of COVID all this material. I wanted to set the context. You two are co-founders in work and life. You're a husband and wife team, and you founded a number of companies, including maybe the most well-known, Buddy Media, which was sold to Salesforce for a cool $750 million. Not a bad day's work. And now you're investors in multiple companies, and now you're authors of this new book called, I'm just gonna say it, just gonna say it out loud, Shoveling Shit: A Love Story About the Entrepreneur's Messy Path to Success. And I wanna start by asking each of you, Why a love story? What do you love the most about entrepreneurship?

So there's really beauty in this struggle. I often say that entrepreneurs shovel all day long and, you know, what that means is they come in, you know, with this positive attitude that they're gonna get stuff done. They get punched in the face 10 times, they'll have one mini win. And really it's about the resilience. And so it's the loving of the shoveling that you keep doing it day in and day out and it gives you purpose and it gives you passion. So we thought it was like our ode to entrepreneurs.

I love that. You know, I had Gary Vaynerchuk, who I know is a friend of yours, on my show also. And one thing he said was, I love the whole thing. I love the stress. I love the boring meetings. I love, you know, sort of the whole thing. And that's your point. You have to love the shoveling and the journey. Mike, what about you?

Well, I think you grow to love it. And Cas and I, this was our relationship. So we started dating many years ago. We've been married 25, together for 28, 29. Don't quote me. The end, we started a business while we were still dating. And so for us, we had to in many ways try to have a life outside of the company. Could have been all-consuming. And so what we're trying to do with the 50 Cheat Codes is not only help entrepreneurs excel at work, but also have a life worth living. What's the purpose of making money and being successful if you hate your life? And so a lot of the cheat codes are actually not work at all. It's how to build relationships. You know, we talk about our date nights Wednesday and Saturday night and how we protected that time. We put it on the calendar. Yeah, right. So all of these cheat codes that we learned the hard way.

Yeah.

Health— we were not very healthy. And how to build relationships, which didn't come easy for us because it was all work. We had to say, listen, we got to step away or else we're going to burn out and we're going to burn the relationship out.

Yeah.

And just because we're married doesn't mean that other co-founders who aren't married have any easier. It's actually just as hard for them.

And in some ways, I mean, I would say just 'cause you're married, you're, you're not immune from the challenges.

No, exactly.

For that, that plague co-founders. And in some ways I'm sure it's even more stressful. So I definitely wanna talk about that. But before I do, I actually wanna ask, you said we started a company together when we were dating. So like not recommended, very, very unusual. But was you, didn't you each have your own entrepreneurial ventures before that?

Yes. Before you were even dating?

Yes. Tell us about that.

So I had opened up the interactive arm of an agency before, so I was very young. I was probably 24-ish, and I got to run that whole arm and start it and building websites. You know, this was 1996, so that was like my first journey into it. And Mike started his first company in college.

Yeah, I was always entrepreneurial. I remember writing when I was 13 years old to the board of Sallie Mae Student Loan Marketing Association, public company, saying they need a student on their board.

That's a great idea.

I got a rejection letter saying thanks but no thanks.

And I'm polite of them, by the way.

I went to journalism school at Northwestern University, McGill School of Journalism, and the internet was happening. And there are times in our lives where, like, you're part of a trend. To me, it was obvious the internet was going to be something. Not obvious to a lot of people, definitely not obvious to the newspaper industry at the time. And so I started a company and What was great about that company, it just forced me to get things done. So I recommend to all young people who wanna start a business, like stop talking, just do something. It doesn't matter whether it's a lemonade stand, whether it's a resale business, whether it's an app company, do something because what you'll learn, you'll be able to use in other companies. And you know, we say all the time that we're a 30-year overnight success story. So it's taken many, many, many years what we're trying to do with the book is help people avoid mistakes.

I love that. I love that. I can relate to that. My book, From Start-Up to Grown-Up, I sort of tell people I wanted them to avoid unforced errors.

Yes.

Yeah.

Especially in the topic of leadership.

Were you a tennis player?

No.

Unforced errors is a big term in, in the tennis world. So I thought maybe.

Oh, that's fascinating.

Yeah.

Oh yeah. What, tell me more about that. Like it's just, 'cause you were, you were a tennis player.

I was a tennis player. Yes. I was a tennis player in college and a little bit after. You just, it's all about your unforced errors.

Yes.

It's the same thing as missing putts in golf. Like, you're, you're, you're trying not to make, you, you're trying to basically not have yourself lose the match.

Right.

Right. So that, I think that's what you're saying.

Exactly. Exactly. So the two of you were obviously entrepreneurial and then you, you started dating and wasn't it that you had started golf.com?

Yes.

So what, tell us about the sort of the coming together of golf.com and then we're gonna get to the dramatic, the dramatic finish. Yeah. Dayma of that.

Yeah. So it was, we, I just moved there, so it was 1998 and I started working for the interactive arm of Leo Burnett at that time. And, we were playing a lot of golf. That was how we started dating, right? We were playing lots of golf and I would track all of our stats 'cause I was a crazy golfer, you know, recreational golfer. We didn't have any place to do this online. And I kept sending it to my brother and my father and Mike and I and put all our stats and I'd get it back and I'm like, wait, I'm in last place. Like, this isn't right. So I said to Mike one day, like, wouldn't it be great if we could track all this online? And he goes, I think we can, and let's syndicate that content. So that's what we did. That was the start of golf.com.

By the way, was golf.com easy to get as a domain name or?

So our comp— our company started off as GolfServe.

Mm-hmm.

And then a couple years in, we actually got the right to buy the domain, which was like great. 'Cause domains meant something back then.

Totally. Yeah. How much did you buy it for?

What was it?

$289,000.

Yeah. Wow.

Okay. As opposed to the millions, I mean hundreds of millions at this point. Yeah.

We were willing. It was actually part of an auction process. Yeah. And it it was one of these, like, we don't go to a lot of these court-run auction processes, but we saw those coming up and we were ready to bid up to a million bucks, which we didn't have. So we kind of got investors to put up some of the money.

And when we won it at $289,000, we were just like, this is the greatest thing ever.

We just do that. That just, that just happened. Cause we knew how valuable it is. It was being sold by NBC. So think about that. Like, that's crazy. They were broadcasting tour events and they were basically saying, we don't think the internet's gonna be anything. Totally.

They were voting against the internet.

And so, and this is exactly like, why do we need this?

Yeah.

Domain. One word domain of a popular sport.

The rich people play.

Right. Right.

Before behavioral targeting, obviously.

I, I'm gonna bookmark this because I wanna hear the story about golf.com, but I just wanna note that like, you know, you two, both of you kind of voting for a trend as opposed to against a trend is very interesting to me. I, I wanna talk about that later, but I, I wanna also just understand, so you were, you were basically, Like created a website people could like what, just so like we capture their scores.

We definitely had a website. It was all golf content. Okay. So you could base follow all the leaderboards of all the big golf tournaments that were going on. You could track your game. We actually went up against the USGA handicap and then forced them to allow official USGA handicaps online. And you could book tee times, you could look up courses cuz you know, golfers are fanatical. They wanna see the course, the slope, the rating. They don't wanna see how hard it's gonna be. And so we provided this content on our site. But then we took the content and syndicated it to all the large, like, newspapers out there. Yeah.

USA Today.com.

Yeah.

Used our golf stuff as their golf section.

Got it.

With the idea that if we can aggregate enough rich people, we could sell ads.

Yeah.

Before a time where you could, like, buy audience segments.

Yep.

Which is how people buy it today.

Right. That makes sense. Okay. So then you created this golf.com and I'm sure it was working for you. Wait, wait. But before we get there, It's like you were, this was your idea. Yeah. And you guys had to do it together and you were dating. Did you at any moment think, I don't know if this is a good idea?

I don't think we thought. We were young.

Yeah.

Um, I was 22.

I definitely didn't think it was wrong. I just was like, so didn't think, yeah, didn't question it. I came home, you know, my, my usual behavior was I'd come home from work, I'd complain to him, I'd ask how we'd solve it. And that was that.

Just perfect. Yeah. Right, exactly. So then, so that was just normal if you're gonna get business together. Yeah. So then, you got into business together and then you have this golf.com and then you, you know, eureka, the entrepreneurial moment, you got bought.

Yes. Within a year and a half.

A year and a half. Incredible.

Big, you know, dot-com boom. This is like the greatest thing, you know, 1999.

Yeah. Yeah.

December 23rd, 1999. We'd been married 3 months to the day. And myself, Mike, and our other co-founder Mike Casper, we all were like, wow, we, we did it. I think it was like a $10 million stock deal or something crazy, like low. Or $20 million stock deal. But we thought like, okay, Chipshot.com just bought us. They're Sequoia based, they're going public, they have their filing ready. This is it.

This is it.

Yes.

The moment.

And the deal was closed.

Yes. And our board said like, all stock, this is what we wanna do.

Yeah. And you were like living the dream.

And we owned, the three of us owned like 80% of the company.

Yeah. Yeah. So that was like, you were just, everything was happening, but then you got a phone call.

Yes.

A fateful phone call. What happened?

So it was March and I got a phone call.

So it was 3 months later.

3 months later.

Okay.

And we, and just so you know, in those 3 months when you do an acquisition and you're like merging and transitioning, they like take over your bank account. So we're no longer paying our employees payroll and we're, we're excited 'cause it'll be like one of the first times we actually get paid. Right. Right. So we weren't even taking payroll back then. Very different now with founders and no FaceTime or Zoom. So the phone call happens and I hit speaker and it was the president, it was Brian Sraub, and he says, hey guys, I'm gonna cut to the point. Sequoia backed out. We pulled our filing and in a week we go bankrupt. And I'm sorry, you're gonna be in bankruptcy. And I'm like, what? And he said, yeah, we don't have any more money to pay you or any of your employees.

It's incredible to think about how that felt in that moment. Yeah. Yeah.

Yeah. I was pretty angry. I remember, I, I think the first thing I thought was, what are we gonna do? For our employees. 'Cause Mike and I were used to, like, living off of, like, nothing. And then I think I got angry. And I think that's the competitive side of me. Like, the athletic side of me was like, oh no, I am not gonna have someone else make me lose.

Yeah. That's right. What a great reaction. And that's like a very entrepreneurial reaction. I do have, like, a question here. I'm, like, saying to myself, Sequoia backed out? Like, what really happened? Do we know?

So we don't know what really happened, but they were closing a big financing.

Okay.

And the financing—

they, they chip shopped. Chip shopped.

Yeah.

So they had a little money when we did the deal.

Mm-hmm.

But we met with their investors and they were all in on this company. And this company was manufacturing knockoff golf clubs in Silicon Valley at a fraction of the cost of what TaylorMade or Titleist would sell them to. And they were selling a lot of them. I think they got the company to $100 million of sales.

Yeah.

At the same time, the environment was like AI meets Taylor Swift in terms of the internet.

Yeah.

People, were losing their mind. Anything with a.com was going to the moon. And so you had etoys.com and all these companies that we've now know what happened. They crashed and burned. Pets.com, right? They were multi-billion dollar companies. And so we're like, oh, chipshot.com, golf. Why aren't we gonna be a multi-billion dollar company?

Yeah.

When you don't live through stuff, right? I'm 24 at this point. You just think things go up and to the right.

Sure.

And so we were very bullish. There was no level of due diligence, which would've kept us from doing the deal. I believe, as we look back. And Don Valentine, who was one of the founders of Sequoia, basically said— pulled back on a bunch of investments because, you know, there was a feeling that this was going to crash.

Yeah, that they were in a bubble.

And a month later, April of, you know, 2000, everything crashed. NASDAQ lost 50%. And so it was whether they'd gone public or not, it was not going to be a great outcome. Now, when we got the call, we were both in shock but also not paralyzed by fear. We just hit the ground running to try to raise money to buy it back, which we did. And so we learned more in that experience of what you could do as an entrepreneur. Yeah, kind of stuff hits the fan. I can say it's shit. It's a fan and you deal with it.

Yeah.

And if you're lucky, you could shovel it, but when it hits the fan, it goes everywhere. You can't control it, so you have a lot of cleanup to do.

Yeah, lots Visuals. Were you going to say something else?

Well, I was going to say, like, I think I— I know Mike's mind. I remember Mike and Mike Casper were sitting there and they were huddling on the side and I was just getting more angry and angry. And I was like, I go back in time as an operator. You always look at like pathways, like how do I move forward? And I kept going back, back, back singing. Did I miss something here?

I kind of miss this. Yeah.

Yeah.

Yeah. Well, that, I mean, it does make more sense to me to understand like kind of the timing and that Sequoia probably had some insight or whatever.

Oh, they definitely did. Yeah. Just like completely obnoxious. And also, I mean, I'll say this now, Monday morning court, shame on us for not also watching what was happening in the world and thinking we were immune to it, right? Like nowadays I think we're much better prepared. Obviously this is 30 years later, but, you know, we tell all of our founders, you gotta, you gotta watch what's going on in the trends here. You gotta be able to predict if something's gonna happen like, like the tariffs that are happening. So.

Yeah, that, I think that's such important information. That's such important insight. And I can see how, like with hindsight, you realize that, We should have been looking at the landscape and that's important.

We were just kind of like flying high. Like they wanted us to all move out to, what was it called? Sunnyvale, California. And I was trying to convince them not to.

We looked at houses actually.

We looked at how, you know, all this kind of stuff and our heads were down instead of lifting up and being like, what is this?

Of course. No, it's so, but then you got back on the horse as you said. And what you both said in different ways is, well, so of course, I mean, we're bank— basically you're bankrupt. And let's also say— I'm going to say like, I won't say depressed, like demoralized.

Demoralized. Demoralized. Yes.

Your employees are going to find out and they're going to be demoralized. I know that one of your family members sued you. Right. So lots going— lots of, as you said, stuff hitting the fan. Right. And yet both of you, you could have just retreated and licked your wounds and lived another day. I mean, there's like, you didn't have any money anyway. So like, whatever. Yeah. I am curious. What was the drive that made you say, we're gonna take this bankruptcy thing, this, this nothing, and raise more money, which was not gonna be advantageous to you, and rebuild it?

I'm uber competitive. Yeah. And again, like, I just couldn't believe that someone else made me loose.

Yes.

That, and it just seemed like a, a silly thing. And I don't know, I was angry and I'm like, let's do this. And I don't know, Mike, what about you?

So we're built differently. I'm not as competitive.

No, you're not.

I am also much more laid back.

Yeah.

And a few years earlier, I'd almost died. I had an artificial heart valve put in, and my outlook changed. And a big part of that outlook was like, what's the worst thing that can happen? Even if this company goes under, I'm still alive, which I shouldn't be. Like, I happen to be caught with zero kind of blood pressure at my doctor and they did—

so, so, Mike, tell that story.

Yes, I was born with a congenital heart defect, a VSD, which is a hole in between the two ventricles, and that caused aortic valve damage. They went in when I was 19, which was a few years before this, and fixed the VSD, noticed the valve damage, and 8 days after that surgery, my aortic valve burst. You need your aortic valve.

Yeah.

Without the aortic valve, it's essential. It— what happens is the oxygenated blood goes back into the heart and you're pumping un-oxygenated blood to the body, which is bad. Like, your body needs oxygen. And so I happened to be at my doctor's office when it burst, which is crazy, which is nuts.

Yeah.

Because if I was sleepy, I would have been dead. If I was anywhere else, I would have been dead. And they rushed me to Georgetown University Hospital. I didn't want to get surgery. My mom says, shut the fuck up, you're getting surgery. Yeah, she's like that. Love you, Nancy Zirkin.

And so much is coming out in this conversation, you know.

And kind of 3 hours later and one bottle of wine for my mom later, we— I have a new artificial valve.

Yeah.

She says I came out of that surgery totally changed. I was a stress ball beforehand. I had I had an ulcer at one point. And I came out—

As a young kid.

As a young kid. And so I came out, it's like, life's good.

Wow.

Like, let's go.

Yeah.

And I've questioned her a lot over the last, like, 30 years. Yeah. And she said it was night and day.

Really?

Night and day. That he— she will recall many, many, many, many stories of him being too anxious to do something. So Srostašić didn't go out. Everything.

And I was like happy afterward. Like, I had a girlfriend at the time. I've told you that, you know, you know, she was kicked out of the hospital because like, yeah, she would come and we'd have fun in the hospital. So I was just like happy, right? I was like, let's live. Wow. And so when this happened with Chip Shot, for me it's like, okay, let's go. Like, we just have to go and get it done.

So you both got there with different ways, basically, but both of you were lying like, we're gonna get this done. Oh yeah. So what was the process of getting it done? You had to find new investors.

We had to first tell the employees.

Right.

And so we, you know, we've always treated other people with, you know, respect in terms of information. We believe that information is power. So we went out right away. They were going to see it on our faces. And we explained everything. We didn't hide anything. And we said, this was our plan. Anyone who wants to leave, go to a bar, like, you're welcome to. We had about 25 employees at the time. Not one walked out over those 3 months. So we didn't pay people for 3 months and they stayed with us.

Why do you think that is?

Well, I think, I think it's relationship-based. You know, you, if you treat people really well and then you create an environment in which they like to work versus don't like to work, and you can't predict that every day is gonna be great, but they make relationships. And so work doesn't seem as awful or dreaded. And I think that's what we had. I also think there were just some incredibly loyal people that wanted to see this through. And lastly, I think they were learning. Everybody was sprinting to learn something new. This was, this was like crazy. Like everybody was doing something that they kind of had some expertise in, but then you pile on the fact that this is the internet and we have no idea what's going on. Then you just kept pushing yourself. And I think that some of those employees really loved that.

Yeah, I can see that. And so you, you went and told the employees. And then you hit the road. Hit the road.

But telling employees is a huge lesson.

Yeah.

That we took for— because, and I remember Cass said, we have to let everyone know. And first I'm like, well, how do we not let them know? Because this isn't good news. But you have to let them know, both because they're not getting paid, and if as a leader you're holding back information, it's going to come out anyway.

Yeah.

No matter how bad. And so people are okay with bad news, especially in the innovation economy. People are not okay with surprises.

Yeah.

So if all of a sudden it's payday and they're like, hello? Yeah, where's my money? Like, oh, sorry, it's coming. Like, no. Like, then everyone would have left because we violated their trust. Cass, her instinct right away was radical transparency. Everyone's in it with us. And that earned us a lot of respect, even though people didn't love the news as we didn't.

Yeah, of course. I guess I And I know that you have a strong value, both of you, around radical transparency and complete transparency. Is there ever a time not to be fully transparent?

Yeah.

What are some examples?

When we talk about radical transparency, we're talking about sharing the good and the bad of the business and treating employees like they're the board. We would go into our quarterly all-team meetings with hundreds of people where people fly in from Singapore office, from everywhere. And we would present financials, you know, how much money's in the bank, runway, where we are against plan, how many customers churned, all of that stuff. And people felt empowered and trusted. And other entrepreneurs who we're friends with were like, why would you ever do that? It's gonna leak to the press. And it never leaked because they felt like they're part of this, like, you know, our companies have a family feel, you know, it's like mom and dad. And especially now they're gray and everything, but at the time they looked at us as leaders they wanted to be associated with.

Yeah.

And we were never— it was never a democracy.

Yeah.

Like, I look at really Cass as a benevolent dictator in many ways.

Thanks, hon, I'll remember that one.

Yeah.

Oh, better. Yeah. And she's also cicada. She emerges every 17 years with this. But, you know, it's a lot here.

Yeah, I'll give you a chance. Yeah, yeah.

But I think, you know, Cass as a leader made decisions. She, she listened to people, but too many companies now, it's like leadership by committee or by democracy. And I don't know if we're kind of pressure testing democracy on the national level. It definitely doesn't work at companies.

Yeah. I think that that is just a misguided attempt at sort of quote unquote being nice to people and creating that family feel. And I think that founders just get confused about both being nice, but also being decisive.

Yeah. I mean, of course we never shared HR issues. So like that was all private. But, you know, I, we would come outta meeting, we had very small offices and we'd have investors come in and I would remember I'd just walk around saying, hey guys, investors are coming in. And someone would be like, well, why are investors coming in? And I'd say, 'Cause you're always fundraising. They're like, well, didn't we close something 2 months ago? I said, yeah, this is just Mike and me making relationships. I don't think most founders do that. I think they would never acknowledge that somebody could actually see who someone was, is coming in through the room and get nervous or be like, wait, what does this mean for me? And I think we were very, very good at just being honest and explaining what was happening.

Yeah. And that builds trust big time, of course. Yeah.

And especially the trust, it's the bad times that you need that trust.

Yeah, for sure.

Right. Easy. My dad used to say easy to win during the good times when you're playing well.

Yeah. Right.

It's the bad times where you have, you've lost a lot of customers or you have to raise more money or you have to pivot. Like the pivots are the hardest thing operationally to do. And if you don't have that trust, people are gonna leave.

Yeah, totally. Was there ever a time where you were not transparent and then you regretted it or kind of came back to bite you?

Well, we were on a phone call with the new Golf— I'm sorry, golf.com board after we raised all the money and we had Matt Sorovich talking to us and I remember it very well. I was sweating.

He's a New York hedge fund guy.

Oh yeah. Yeah.

So very, very, we were very scared of him.

We were very scared of him. And, and his partner—

Now we're friends with some of those creatures.

Yeah.

And, and Jeremy Minij and they were asking about the company and I went through all the details. And then they asked about sales and I was like, well, you know, it's okay. Like, Mike, why don't you give an update?

And then Mike, it was a little rosy of an update and he, he lost his, you know what? And he slammed the table and said, don't shine the turd.

Don't shine the turd.

Like, I want all the, all the information.

Which is one of the book chapters, guys.

Yeah. And it became actually a motto going forward where like, if it's bad news, Let's say it's bad news. Like, get it in the— and as a leader, you have to name the bad news. You have to take responsibility for the bad news. And you have to communicate a plan of what you're gonna do about it. You can't try to like put a cowboy hat on it and say, oh no, it's like doing a rodeo thing.

Yeah. That kind of rigor is really important. You have a plan and you've thought it through and you have a plan.

And telling all your employees to do the same in meetings.

Right. Right. Yes. I mean, there's so much there around like when the leader doesn't do that, but expects their employees to do that. 100%. Okay, you raised the money and this is still for golf.com. We ought to get to Buddy Media, but like golf.com, you raised the money and then what, you put it back together and what ultimately kind of came from that?

So we got very lucky on the fundraise. We—

Luck seems to be a role.

Yeah.

For your life.

In everyone's life.

I guess that's true.

I mean, in everyone's life.

You make your own luck.

And I think we made some of it, but we didn't have relationships with investors. And so we hit the road and we just had a lot of meetings and we met a VC in Chicago named Keith Bank who was a golfer trying to play the top 100 courses. He liked it and then introduced us to a top lawyer who was a member, a leader at Medina Country Club, which was like a fancy country club in Chicago. That's where they played the US Open. And he's like, I'll do a lunch with my golf buddies. And literally between those two contacts, we raised $1.5 million to get restarted. Everyone else said no. So we got like 100 nos, but we happened to find some golfers who were rich who wanted to throw in some money. And then the second part of golf.com, we got lucky, is there was this kid named Tiger Woods.

Yeah.

And Tiger Woods at the time was a global icon, as big in the media as Taylor Swift is today. People don't realize, like when he was winning, the first time he won the Masters, in a runaway by 12 strokes. First time anyone who looked like that, a Black kid, had won a PGA Tour or a major event. And he had a lot of sponsors and those sponsors wanted to amplify their relationship with Tiger. Where did they go online? Golf.com.

Oh.

And that's really, without Tiger, golf.com does not exit for $25 million a few years later.

Amazing. It's like if you had had soccer.com, that wouldn't have been the time, right? Yeah. The time happened to be right for golf.

Right.

Right. That's fascinating. So how did you exit? How did you ultimately resolve that?

Well, every time we would go up against a deal, and this is way back where we were like serving our own ads. So I was serving ads on DoubleClick again, something that I never knew how to do before. And Mike would sell, you know, to the big, like a lot of car companies, right? They wanna reach golfers. And he would be going up against Time Inc. that owned Golf Magazine and they owned Golf Online and Conde Nast and Golf Digest and Golf Digest. And he would win on all the bids. And so they were— not all of them, some of them, most of them, plenty of them, plenty of them. I love that. Like nice compromise.

And please say more.

And basically, uh, he kept beating them. And the next thing you know, Goff, you know, online Time Inc. was like, we want to buy you.

Julie Hansen, who went on, great executive, not just because she bought us, but went on to, you know, run great companies, Business Insider, Bumble. Yeah, we love Juliet.

Got it. And so that's how it, that's how you got bought by Time Inc., you said.

Yeah. But we, but I mean, it was no like flowers and roses.

Right.

We got down to 4 people.

Yeah.

So, you know, we were, I was like working, you know, booking ads, running the company, doing all the financials, figuring out the marketing. Mike was doing all the—

having babies.

Oh, I was having babies.

I was gonna say. And Mike, you had 2 babies during that period.

Yes. Right.

I did.

Yeah. And you know, this was, like we kept laying people off because the ad industry was just coming back in 2005, late 2005.

Because I just wanna also clarify for everybody who doesn't remember, like there was that dot-com bubble and the dot-com bust.

That's right.

Nobody was advertising anymore.

No, no one was spending.

It was like the internet's over. Yeah. That's stupid.

It was like done.

Amazon.com.

Right.

Yeah. I didn't talk until like 2003, '04.

For the ad business.

And we, and our revenue, we cobbled together a few million bucks, right? Yeah. Like, I think our biggest year was like $2.5 million, $3 million.

Do you remember when I had to go, like, we were like watching paycheck to paycheck and, and watching like payroll check to everything. And I think I showed up at someone, I think I flew from Chicago to New York to get payment once because, you know, everyone was holding on to their payment.

Yes.

Because it was such a— I'd show up at offices, say I'm not leaving until I get the check paid.

You're just like me.

Totally like that.

I could totally relate to that. So I guess I am curious because you, you know, you sold it to like, like you were about, like we were about to say, oh, sold the timing, ta-da, move on. But you're saying no, no, no, no, no. We had 4 people left.

Yes.

It was like I had to go fly in to get money.

Yeah.

And I am curious, wasn't there a moment that you thought, okay, this is just not worth it?

I think neither of us are quitters. I think I would've thought it like I was a quitter. I think I was really tired. I mean, I just had our second kid and I was like, I was, and we would be in an office that was just about this size and doing our work every day. I think I was really, really, really tired. That's about it.

Okay. Just tired, but you're going to keep going.

Yeah. Tired and—

You just don't quit.

You just, you just keep doing it.

We were generating revenue. We believed in it. We thought the internet was here to stay and we thought we'd build a business.

I also would tell Mike like, okay, Mike, like you gotta, you gotta see what we're going, like, look out for land. We've got to go somewhere here.

Yeah.

But then we started winning all these ad dollars.

Yeah.

Yeah.

So then it felt like, when you say look out for land, I always think of us like on a ship, like Mike's in the front. Yeah.

He's like looking left, right, which way we should go. And then he'll say, turn around and say to me, okay, right. And then I help everyone kind of turn and get on the same rhythm.

'Cause she does all the work, right? Paddle right, paddle left.

Pretty much.

Yeah. Nice life. But I guess what I mean by that is that you wanted to, like, you wanted him to—

I wanted him to say like— land the plane.

Yeah. Land the ship. He landed the plane.

And also, you know, he's, really great at consuming information and seeing where things are going before they actually happen. Yeah. So he kept saying to me like, this, the ad business is coming back strong.

I promise you.

I knew I would, Mike Casper and I'd be like, yeah, sure, Mike. Okay, whatever. And then it did. And so he kept giving us glimmers of hope because, you know, we saw he's just started winning all these deals.

Got it.

Yeah.

Okay. And so then you sold the company and I appreciate you said that about the trends because in like sort of seeing what's coming. Because Mike, I have a question for you. So Cass is busy giving birth to your third child in a C-section, and you're sitting there musing about this thing called Facebook. And I am so curious, like, what did— okay, I'll just be, I'm gonna throw my, throw my cards here. When I heard about this thing called Facebook, I thought literally, who would ever do that? And it took me 3 years to even get onto Facebook. And for years it was just about like seeing my old college or sorry, high school friends or whatever. Right. But you seem to have a different perspective than I did. What did you see about Facebook that was so— that you knew was going to be something? How'd that turn into Buddy Media?

So I had a company in college, a student company, and we had made an attempt to do that type of service. It's called the Main Quad, was what the web service that came out of UWire. I kind of was working with some San Francisco entrepreneurs. And we could never get it to work. And one of the big reasons was identity. We— you couldn't figure out who was who. And what we've seen in the internet, the anonymous internet's an ugly place. And so it just never worked. It was— there's abuse, there was like guys doing the stuff that guys do, and it was just not great. What Mark, I think, really honed in—

Zuckerberg—

this idea that everyone— Zuckerberg— everyone wants to belong. And the ticket to entry was your real identity and you connected with people in your real life. So it was this virtual representation of real-life relationships. And that is what got me so excited. They had mapped real relationships for the first time ever. And he got up on stage on May 24th, 2007 and said, and called on developers to build applications using the social graph. And I immediately said, this is a new internet. Because instead of playing solitaire alone, you could play, you know, Scrabble with friends through the computer. Mobile phones weren't as big. The iPhone hadn't launched, right? But this whole idea that you as a developer could have send functionality to friends and recruit friends to do stuff was just big. And, you know, Cass was busy. I know. I would've talked to her earlier, but she was delivering Csexually. And she gets wheeled back in with this, probably our most beautiful baby, baby-wise.

I think.

She was.

Yeah, she was good.

Yeah, she was cute. I can't say that about the boys.

That's not true.

Cole was very cute. Miles got a little banged up.

Yeah, he's a little banged up, but they're all fine now. Okay. Um, and I said.

They're all handsome and pretty people.

And I said, I got it. I wouldn't go that far. But I said, I got it. She goes, what, like food for me?

I thought it was going to be sushi.

Like she hadn't.

Like he had ordered it.

Soft cheeses. She hadn't eaten In the 9 months, right? I go, no, I gotta learn my new business or our new business. And she just shook her head. It gave me the, you're the worst person in the history of the world look. 3 months later, she's building desks in Columbus Circle. And that was the first office. And what's great about the relationship is I could never do this without Cass. Like, you need an operator. It's all about operations. You also need revenue and ideas. And so we really work well together. And there was trust in that, in that decision, because I think she also saw social media as a new trend that was just about to happen. Yeah, in a big way. And so she is not— she's a radical realist. I wouldn't call her a dreamer. She's not a pessimist at all. So it's not that she's a pessimist, just she's not an optimist like me, or as much of one. And good ideas she embraces.

Yeah. And so it sounds like you had a prepared mind for the idea of what sort of the idea of social, the social internet or whatever it could be. And social media didn't catch you by surprise and you saw the possibility of it.

I also, yes. And I also think that I've got, been very fortunate to be around entrepreneurs. And when entrepreneurs who are much smarter than you start to focus on something, you should focus on it.

Yeah.

Um, there was a guy named Mark Pincus who's still around. It's not that he's gone anywhere, but he was living in New York and his girlfriend at the time worked for Hachette. And so we were spending some time together.

He's at the publishing company.

Yeah.

Yeah. And Mark went on to do Zynga. Zynga, right?

Gaming company.

And he invested in Buddy Media. We were supposed to invest in Zynga and never got that call. I don't know what happened, Mark. But Mark, if you're out there, he called Fred Wilson instead, and Fred got the deal. But a lot of entrepreneurs like that were circling this thing called Facebook. And I was like, okay, if these smart people— and they're much smarter than me. Like, I can hustle and outwork anyone, but like, you know, I'm kind of average. What— or I used to be. She thinks I don't work as much anymore.

You can't outwork me.

I cannot work. Cass is a monster.

But together, monsters.

Yeah. But focus on what the smartest people in the room are interested in.

That's great advice. So what was Buddy Media was supposed to be. And then what I know is that you pivoted multiple times. So I both want to hear about the pivot, but I also want to hear about what it takes to know, oh, this isn't working. Like you said, Mike, I think you said we love throwing away stuff.

We love it.

Yeah. So talk about what Bed Buddy Media was supposed to be, either one of you.

Mike was pitched me on the idea that we were going to create the social currency, like the Facebook currency that big companies would wanna come on and like use it. And it, I, I don't think I really thought it made any sense.

Sounds like an early Bitcoin, early crypto. Wow.

When you say currency, I mean it was, it was more of like Amex points for Facebook.

Yeah. Okay. So that sounds like, that is like crypto.

Yeah. But we didn't understand kind of monetary policy and there became massive inflation and no one wanted our currency. Mm-hmm. and I, we just kept having conversations with companies and they said, we think Acebucks is what it was called, is an awful idea, but help us with Facebook. Like, we want to figure this thing out. I remember meeting with HBO and, you know, a bunch of media companies were first, you know, because they're in the information business. And we then said, okay, we'll help you. And we started building custom applications and we were pretty successful with that.

Yeah.

And then Cas is Mike, Cass is like, you guys can't sell this anymore because it's not scalable. I can't find enough programmers to do it. I'm building one-off things.

We can't get— we have way too— I mean, our product roadmap for each set of engineers was just out the door. We couldn't get these things done fast enough. And I kept saying that to Mike, and then he had an idea.

Yeah. And so a board meeting, we're talking, it wasn't just my idea, you know, in your seat was Eric Hippo, who at the time was working for SoftBank. Now he's at LayerHippo Ventures. And we had a really heated discussion of like, how do we take this from a sales machine that could get a lot of custom work, like an agency, into a software company? And it's when we came up with the idea of like productizing it. So a lot of the functionality is the same— send, recruit friends, post something, yeah, you know, do sweepstakes, like all these things that we were doing. So We invented something called SAPLits, which are social applications, but they're small. They're like applets, like little applications, and you could piece them together to do your social marketing. And the big breakthrough was not just selling it direct to brands, but we went to ad agencies and we said, here's a platform that you can make money from. And that's when Martin Sorrell and, you know, Publicis, they, the British and the French came in together and investigated us, which is one of the first, one of the only tech companies that both of them have done in the same round. Yeah, we didn't want to be a WPP company or a Publicis company or an Omnicom. We wanted all of them.

Yeah.

And what that did is it helped us scale because it not only brought in revenue, but the work was being done by the agencies, right? So we didn't have to B-heavy service.

So were you like— I still don't quite get it. So it was a B2B thing and you were basically allowing companies to do kind of social marketing? Social marketing and maybe commerce?

It was almost like a content management system.

Okay, got it.

For these social networks, Facebook and this thing called Twitter at the time. Yeah, rebranded.

Yeah, YouTube. And if you think about it, like Unilever, right? Yeah. Think about how many different you know, people are on each brand and how many different security levels and permission levels. So our technology, thanks to Patrick Stokes and his team, they just built this amazing platform that every big brand could go on and then really figure out how do I want to market to someone and what language.

Yeah.

Right. So if someone's English speaking, but they live in, you know, I don't know, South America, that would happen. And so this became the platform and we were able to get like 9 outta the top 10 Fortune 500 brands.

Got it. Onto Facebook.

Yes.

And other socials. That totally makes sense. So then, so you're doing your thing, you're operating the business, and then you sold this to Salesforce. Like, what? Salesforce? Didn't see that coming. So like, how did that all come together? And talk about also, if I'm not mistaken, you had other term sheets in front of you, but you chose Salesforce. Like, how did that all come together?

Yes. So, well, first of all, we weren't trying to sell the business. We thought we were going public. We'd hired a woman named Susan St. Ledger who was a top Salesforce executive to, and she knew what we didn't know. We'd never built a software company.

But hang on, didn't you do that like with the guys, like towards getting attention? Didn't you hire her kind of strategically?

Yes.

And— I, it was very strategic on my part.

Yes. And—

Okay.

And the and being like, we knew we didn't know. Like we'd never—

Yeah.

Yeah.

She was great.

We'd never scaled a sales team. Her whole career was building armies of salespeople.

Yeah.

And so we wouldn't have done it just as an FU to Salesforce, even though I like that idea.

Yeah.

At the time, we desperately needed a leader. She was by far our number one choice, which is why we waited a year, dated her. It felt like, like flying out there. Oh yeah, having dinners, getting grown-up clothes, getting— yeah, cats had to get out of sweatpants. Susan, if anyone knows Susan St. Ledger, one of the great executives, she's gone went to do much bigger— she dresses incredibly well. She wears a lot of Chanel.

Yeah, we all have to up our game sometimes.

Yes.

Yeah.

And so we, we're still scared of her to this day. But what happened, and there's a good, like, lesson for all entrepreneurs, is build relationships with potential buyers just because it's the right thing to do, well in advance. So I have relationships for years with executives at Salesforce and Google and Yahoo and Microsoft, which had a huge ad business at the time. You know, Rick was running that business and I started to feel heat. Like I'm getting calls like, oh, Marc Benioff wants to meet with you. Like, okay, I don't get that call often.

Right.

And same from Google. We had an offer when we sold to Salesforce, we had an offer on the table, $100 million more from Google. And I later learned that they were willing to go much higher. We loved Salesforce. We still do. Love Marc Benioff, love the team. If you're in software, that was and is the place to be.

Yeah.

It's a bigger company now. It's gone from $16 billion market cap to $300 billion on the back of just incredible growth. They own the sales team with their CRM product. They then launched Service Cloud. They own service. And what do you do before you get clients, you market. So Marketing Cloud was the next. And instead of just doing like ad serving, he went after social, which was a wide open new thing.

So that's how you guys got into the portfolio.

Yeah.

Yeah. But I still, I have to say, I don't think that you wake up every day and leave $100 million on the table. You know?

So we, you know, as a board, you have a fiduciary obligation as shareholders.

Right.

And so it's actually a very serious discussion. And I worked with John Lambros, who, you know, a great banker in the space based in New York City to get an opinion. And even though the money was higher, we were very concerned that everything Google was touching was getting stuck in Washington at the time. They just bought a travel service, Sabre, the Sabre system. They were a year into that review with the, you know, Department of Justice.

Oh, and so, so you mean antitrust stuff?

Yes.

Yeah. And so we thought that they already own advertising We ran the table in social. When I say run the table, it doesn't happen anymore. We got in 3 years from the time we started selling the product, we got to $50 million of annual recurring revenue with 9 out of the top 10 global marketers. And these marketers are paying $5,000 a month. So, and we had a lot of customers. And so the idea that that was gonna be put in Google, it was gonna be like, wait, you already own like search, right? Like Google, like was it, There was no Bing at the time. They were 100% basically market share, little Yahoo. And we just said, if this gets stuck for a year and we lose employees, we're in limbo, like—

Being in limbo when you're supposed to be acquired is actually very damaging.

Yeah, the momentum is just—

Totally.

And there's zero risk in Salesforce.

Yeah.

They don't own anything in marketing.

Right, that was just gonna work. That makes a lot, this was more pragmatic. Yeah. You know, Kaz, I think you said in the book that part of why you thought about about this acquisition was that also it was a, like the business was affecting your family life.

Oh yeah.

At least one of you said that.

I definitely did. I, you know, I think, well, we probably both admit it. We had 3 when we started. So Viv had just been born and Cole was 3 and Miles was 5. So we're doing this now 5 years and we are barely there, right? Thank God we had incredible babysitters, but we are, we are barely there.

Yeah.

And it's taking a toll, bigger kids, bigger problems. And, you know, our oldest was having some health issues. Our middle was getting in trouble and he never got in trouble. Like, you know, principals calling me like, what's going on? And it was just time. It was time for one of us to get back. And Marc Benioff was gracious enough to allow me to go back, which was great.

Go back to home.

Stop working. Yes.

Yeah.

Which for the record is way harder taking care of kids than any job.

It is.

It's just like, It is.

Yeah, totally. So, right. So you just realized the kids need a parent.

Yeah. I mean, you know, when they're very little, my theory is a lot of people can love them. A lot of people can read to them. There's not big conflicts at school. You're talking like someone took your book and, you know, like that kind of stuff or toy. But when they get bigger, you know, you start to see things and we weren't there enough. And one of the things we've been lucky enough to see is because we have been there for the last, you know, 13, 14 years consistently since selling, you know, Buddy Media, we've noticed that they actually have learned some things from us. And what we've done is led by example. Like we could tell 'em 8 times outta 10 every single day, like, you gotta work out, you gotta work out. They don't care. But now we see them working out because they saw us working out. So lots of different things that I think we needed to get back to. And Mike stayed at Salesforce for, was it 3.5 years, 4?

Yeah, close to 4.

Yeah.

And loved it. I wasn't very healthy, which is why I'd left, but it's a great company.

Yeah. How did you feel about kind of fitting into a, 'cause that, you know, it was smaller than it is now, but—

I loved it. I mean, I haven't, you know, I don't think I've told the story, but very early on, you know, Marc Benioff made it very clear. He said, I really want you at the company. You're a real leader. If we cut open our arms, we bleed entrepreneurship. I need that here. And you control your mental health and your mental outlook. He didn't understand why he'd pay these entrepreneurs all this money and they'd get mad at him that, you know, like he's trying to make their life miserable. Like, I'm going to pay you a billion dollars and make you miserable. And Mark, he gets off on philanthropy, right? The 1-1-1 model, the philanthropy, you know, the integrated philanthropy. And he said, if you're not happy, 'Just do something else. Come to me if you need another area. You control your outlook. If you're miserable, that's on you, not me. I want you to be happy.' And I remember I was like, 'Oh, that's so great.' I almost cried thinking about it. I'm like, 'That's such a great outlook for anyone. Just like, I want you here. Come to me if you're not happy.' and I was happy. Like, it just— I did what I wanted to do. I moved around. I was chief strategy officer. I headed up, you know, CMO for the marketing cloud for a while. I think I did good work. I also gained 30 pounds and my cardiologist said I was gonna die if I didn't get in better health. So I was like, yeah, Salesforce, there's no like first gear, second gear. It's like, oh, Unilever's not happy, I'm flying to London, right? I'm going to dinners every night. I'm like, I'm having drinks before meetings. And I'm in New York before they had a New York office. So if any customer needed love in New York, like big customer, they'd be, oh, Laz, I'll take you to dinner. I'm like, what do you mean? Like, and so I— and we weren't as connected because I was traveling. So like, I needed to like have a restart. At first, the company was like, just take some time off. But it became clear that I could have been there for a long time, but it's just not who I was. Like, I'm an entrepreneur.

Yeah.

And so I feel very good that I did more than I said I would do, I think left the Marketing Cloud in a better place. You know, the business would've been challenged either way because Facebook was changing some of their algorithms and how they worked with buddy media type companies. So it was another lucky timing thing 'cause I don't think we would've, we would've probably pivoted, but our, the business we had would've been impacted if we just had been a standalone company.

Yeah, it makes sense. All business trends at some point change for sure. But I guess I'm curious, what advice specifically do you have for, because not everybody gets that speech from a Marc Benioff. What specific advice do you have for founders after they're acquired to kind of have a happy 2 years, 4 years, whatever it is inside the larger company?

It's very hard. And I actually don't talk about it a lot 'cause it's like first world problems, right? Like I can't talk to a lot of people about like those issues, but they're not that dissimilar than any other issues in business. And what I would say is that it's the same thing that Mark said to me. Like, your mental outlook is yours. You have a filter on. You're going to be pissed at your manager no matter who it is. And it's not fair for that manager that they're managing someone worth $300 million, like, if— or whatever you're worth, they're working and they're your boss, realize that that is a weird dynamic. They know you don't need anything and they know you're going to get bitter. And what I say over and over again, you don't have to be happy, but just kill people with kindness. Like, you're gonna work with these people over the next 50 years of your career. You're gonna need stuff, you're gonna help them out. Do not carpet bomb anything, you're gonna be pissed.

And that's what, and we even saw that a lot when we did acquisitions. There was a lot of them that would come to us after they did the acquisition and their attitudes would totally change, like on a dime, like flipped. And I remember thinking, and he and I would always talk about this, like, did they not understand what this was? Because I overcommunicate everything and they would make it difficult. They would make it difficult for everyone there as if we were causing all this pain. And so I think it is a mindset thing.

And it all comes from ego.

Yes.

You know, and identity that you are the man or the woman, you're the CEO, you're the founder. You're getting invited to all these like banker dinners and conferences. And you know, I won Ernst Young Entrepreneur of the Year. Like we laud entrepreneurs, we put them on pedestals, and then you're just another worker. And so you just have to like be very cognizant of leaving that ego. And what happens when you make a lot of money You think you know everything. And I'm not saying, like, we went through this, friends. You're like, oh, we must be brilliant. But we're the same schmucks we were beforehand. We don't know everything. We know very little. We knew how to build and sell a software product, which led to the outcome. And, you know, learn. Go to a company and learn. I learned more in those almost 4 years about how to focus an organization, how to lead, how to communicate, how to communicate to investors. I was one the kind of investor relations people in New York, 'cause I was here. And so use it as a way to learn stuff that you don't know. And I think what I learned as an employee makes me a better leader and manager now because it was the first time I was an employee. I was never an employee. I went to Northwestern, I started my companies, and I can feel what it's like not being communicated to. I could feel what it's like not having enough resources to do my job, right? Like, just soak it in. Work 80% as hard as you were. Like, chill out a little. It's not hard to have a job after you're an entrepreneur because you're not worried about— like, like, we were always worried about payroll.

You're not worried about, like, am I pissing someone off? And, like, HR—

like, don't create issues. Chill out. Learn. Give.

And realize what you just got and be grateful. I think that's the other thing, is that we were very grateful grateful. And did we wanna run this company for the rest of our lives? No. But we were grateful that someone really appreciated it.

Yeah. To the tune of $750,000.

Yeah.

Yeah.

What was it like to have money like that kind of money? Like genuinely, as we say, F-you money that like, because you didn't grow up that way and also you didn't, neither of you, you were like making ends meet. So what was it like to suddenly come back?

Well, we, we both kind of grew up on third base, first of all. Oh, you did? So we did because, you know, we had all of our education paid for. Yeah. I was I was a very trained athlete, so that meant lots of lessons and coaches and mental coaches. So I, I, I did have the opportunity, you know, upper middle class family. But when we started everything, like, and we started dating and moving in together, we didn't have anything. And the only thing that we had, we, we had managed to save $30,000 that went into golf.com. So that was gone, right? We didn't have that anymore. And it's not like Mike's company UWire, when it was acquired with by Student Advantage, that also hit the tank when, you know, it, the whole dot-com bubble burst. So the thought of more money, I think to me it just meant we could have more experiences with our family 'cause we had not really had any real vacations and we couldn't afford them. I think it, I think money provides comfort, but it shouldn't change anything. And then also I think what we've learned is it allows you to give more. So we've, you know, gone really, really long into giving, especially Cycle for Survival. Hmm.

What about you, Mike? Any thoughts about like what it's like to have that kind of money?

Yeah. So it's weird. The first year's weird because all of a sudden you have money and you're like, what do I buy? What do I— and you do stupid, everyone does stupid stuff.

What stupid thing did you do?

Well, we'd already bought, like right before the deal, we bought a house in Turks and Caicos. We love loved Turks. We sold it during COVID I don't think we bought anything.

I think we bought a minivan. I love minivans.

Yeah, like we didn't buy anything crazy, but the house was like the biggest thing. And you know, we flew private a bunch of times.

And I think flying private is—

but let me, let me just say minivan is a little like, come on. Well, we had lots of kids and dogs. We had lots of kids. But, but you have to understand, like flying private, that was to get to camp visiting day, which is like, for the record out there for parents, the worst day ever. So it to get— like, it was convenience thing. It wasn't like, oh, we're going on vacation and taking a private jet. This was like, we have to go here to here to here. Yeah, I think it—

the thing that's weird, what I was going to say, is it's actually how people treat you.

Oh, that's the difference.

Like, we didn't think we changed that much. Maybe we did, but like, people kind of freak out in different ways. And that's true. Part of it is like an expectation. Some people are like, they're super rich, they're gonna pay for everything, which which we usually do anyway, but that's more because we want to, like—

No, but we get that a lot still where, you know, we had what we thought were friends even since 2012 that just never offer, right? And things like that. So you do— you're right, Mike, we do get a lot of—

and even family, like, expectations. But it's at the end of the day, they're— it's all like, they're— it all buys freedom, which is what I like.

Yeah.

Yeah.

Like it gave us the freedom to go into investing, gave us the freedom to, you know, up our involvement cycle for survival, which is really important to us. It gave us freedom to buy a healthcare staffing company. It gives us freedom to write a book and have a social media editor, right? Like a video editor.

Totally.

Which we realize is a luxury because most entrepreneurs, if they're on Instagram or TikTok, they're like doing it, cutting it up and doing it themselves.

For the record, I myself do it myself.

Yes.

Yes.

He, you know, it's kind of like we're at an event with Gary Vaynerchuk.

Yeah.

Very good friends. And he puts up like courtside seats to the Knicks, right? And someone bids up to $100,000 for the seats.

And they're like, going once, going twice.

Gary buys it for $125,000 just to buy his time back, right? So like his success has given him the ability to buy back his time.

Yeah.

And I remember that was such an like lesson of like, oh, money buys time. Yeah, like it does. And anyone who says, you know, money isn't good or bad— we have a lot of friends who've made a lot of money and lost a lot of money. One friend who made $200 million, lost it, and made it again. Wow. Right? And it can cause people to do crazy things and to do bad things.

Yeah.

And so, you know, we have a whole what we recommend to our entrepreneurs who make a lot of money, which is kind of like don't buy anything for a year. Find someone you trust to manage it because just because you did well in the business doesn't mean you're like the world's greatest money manager.

Yeah.

You need someone to tell you no. And if you don't have someone to tell you no, like liquidity's low, like you can be very rich and low, have not had a lot of money.

Cash poor.

You buy like a few houses, a plane, a boat, which we 'Cause suddenly you're talking real money. And especially in New York City, right? 'Cause talk to anyone in New York City and even the people living in $50 million townhomes think that their place isn't big enough. Like they're missing.

Everyone's overextended.

Yeah, so it's like, you know, it's, you are who you are. Money can amplify the good and the bad.

Yeah, it's so funny you talk about the way people treat you because I had Jim McKelvey on my podcast. He's the co-founder of Square along with Jack Dorsey. And he said that when Twitter, Twitter went, not Twitter, sorry, Square went public, he suddenly got taller, more handsome, and funnier.

Yeah. That makes sense.

Yeah.

Yeah.

You can probably relate to that.

We were invited to a lot of things.

Yeah.

Yeah. And let's just say we had probably 30 to 40 invitations to galas that year.

Yes, I'm sure.

Yeah.

So you two keep each other grounded, I would also think. And I have to say, like, I know it must be that your marriage affects your businesses and your businesses affect your marriage. Talk about that interplay.

So I think I am probably too grounded. Like, I tend to be a hermit, and I'm—

And because you bought a minivan.

Yeah. Well, I love the organization of a minivan. The fact that it has all these compartments and the doors open, it's like, I love it. But Mike pulls me out of that, pulls me out of my shell. I'm an introvert, and I think he's way up in the sky, and we kind of pull each other in the correct way.

Ways.

So it's just been a perfect yin-yang complementary, like, skill set and life in that sense. And like, people always say like, "Oh, well, who does this?" Well, like, Mike's VP of religion, right? Like, we have little titles for different things because then that's how we know who's got it, right?

And grocery shopping. She hates the grocery shopping.

I hate grocery shopping, and you hate laundry. So—

So division of labor.

Yeah, division of labor because it is a team at the end of the day. I think I'm way more team-oriented oriented in terms of my analogies probably than Mike, but because your sports background— yeah, sports background and just like the childhood.

Tennis and golf, they're not the world's greatest teams.

I also got recruited D1 for basketball. Thank you.

Okay, how did that go?

I didn't play. I didn't go there. That was Davidson. I should have gone there. Anyway, so you also need—

I mean, a big part of us is also the me.

Oh, this is what Mike loves to talk about.

No, I don't love to talk about it, but like, I think a big of— so we love each other and we like each other. We all have a lot of friends who, you know, who likes each other, right?

Oh yeah.

And it's— and there's a difference.

Totally.

Like, I don't doubt most people love their spouse, but do they like them? They've shared interests, they've shared vision. And so I, I got incredibly lucky there. She's an older woman who's much more— it's just a chronological fact.

I know enough. I know enough about you to know that you love saying that.

I do, but like, I got someone who really is responsible in a way that I'm not, you know. And I've learned a lot from that. I also like to do crazy things. I like to go see the band Phish. I like to see all sorts of live music. I like adventures. I like, you know, if you ask me to do something that's crazy, yeah, let's go.

I'm, I'm kind of like— he took our middle son for his 21st birthday this past weekend on a great golf trip and everyone's like, oh my God, it was like Mother's Day. How did you do that? I'm like, I had a perfect Mother's Day. I was alone with my dogs. Like it was brilliant. It was silence with my dogs. It was like brilliant.

So that works for both of you.

It does.

That's really great. So how did, how was it though for you to write the book together? Because that harder.

Yeah. Same lane.

We gotta go there.

Yeah.

Same lane.

So same lane. And I think Mike would say, I— so he, he didn't want to write a book. Here's the journalism major not wanting to write a book. I wanted to write a book. I also wanted to get it— I thought it would be better to get it out and quicker to get it out that way than doing a podcast.

Yeah.

And podcasts seem like a lot of work. And newsflash, they are. Yeah. I mean, a lot, a lot of work. And it feels like a deadline all the time. And that would just make me crazy.

It does.

Yeah.

Yeah, it is.

And so we wanted to do this and I had kept of the chat.

Hang on, hang on. We wanted to do this. Not really, you wanted to do this, but you didn't want to do this.

Yes.

At first it wasn't on my bucket list. I wasn't totally against it, but like, I went to journalism school. I'm the writer. So when we say we're writing a book—

wait a second, that's interesting.

In my mind it's like, oh, you're writing the book.

Well, wait, but you know that I didn't—

I'm trying to incite a fight here.

Yeah. No. So we did fight at the beginning. Yeah. Because it was very awkward to do something together. Like the company's like—

rather than having division of labor.

Yeah.

Because you'd always had division of labor.

And the communication around writing was not what I had hoped for. I'm only laughing because I did most of the writing to start, and Cass's editing would be, I don't like it. I'm like, okay, you didn't— that's okay, tell me what you don't like. It's just not doing it for me.

But, but that was the beginning. You have to understand, I'd kept all the lessons, feedback. I kept— okay, what I had kept all the lessons over the last, you know, 30 years of working.

You were just taking notes.

I kept them in like a, like a memo, like a note on my computer and I kept them all. And so probably like 10 of the 14 chapters, I already had the bullet points and the outlines and knew what they would be about. So I would scaffold it and I'd do very detailed bullets and I'd try to come up as best as I could with, I'm also dyslexic for the record, try to come up with like the topic sentence and the concluding sentence. And then Mike would help and I'd say to him, like, here are all the stories. And then he'd help to like bring it to life. And then I'm a great editor. So then after that we'd do it and we'd go back and forth. It took us probably a month to find our rhythm. And then after that—

And voice, the voice was hard.

Yeah, 'cause we kept trying to figure out how to share it. And then after that we ended up writing it in 3 and a half months.

Yeah, yeah. So kind of once you find your rhythm, it's like—

Yeah, we got a track.

And then no one sells books. Like there's no like agency or, so you have to sell the book yourself. So then we're like, okay, now we have a third job.

So then, then I'm like, yeah, you, I mean, when you say no agency, I mean, that's the whole thing. You write the book and then no one tells authors that you have to now go promote the books.

You gotta go and like, and you have to figure out sales.

And I kept going every night. I'm like, I'm looking at the numbers. I'm like, Mike, go sell. You know, he would be like, I'm tired. I'm like, get back in there.

I'm surprised your friend Gary Vaynerchuk didn't tell you I mean, listen, I think things would happen with Gary though.

He has a huge audience and a whole army that if he pressed a button, they would buy something.

But he's been— what's been great is you know who your friends are. As you probably realize when you write a book, you know who really is pulling for your success and who will actually do things about it. And who are the convenient friends. When one of our friends buys, like, writes a book, we buy 100 copies.

Yeah.

Because now you know what it's how important And we always did it because it's like, if they are going to be, I think, put in the effort and be vulnerable and add their story to the world's knowledge, like it's kind of an important thing for someone. Now we realize how important it feels.

Yeah.

And it's not just buying the books, but we did a 3-hour livestream with Gary, National Shovel Day, which is a holiday we made up. It's on National Garden Day and we got dressed up as farmers and, you know, we sold a lot of books. Yeah. I mean, and so that, you know, like, he— and the thing about Gary is he gave us so much in this book, not only helping us think through it, but actually team and Maha, who's, you know, we love Maha, who ran comms for him. That's how we got here. But it all started when he showed up at the Buddy Media office, and he didn't have money for an office. And so this little, kind of what we thought was little like help that we gave this young entrepreneur— he's a little younger than us— turned like into this full circle moment where we're in his office, half a billion dollars of revenue company, doing a live stream when he started in an office no bigger than this studio, which was our little conference room on 60th and Columbus on, you know, right by Columbus Circle. Yeah. So the more you give, the more you're gonna get.

You know, and that's one of the lessons in the book. I think you sort of said, I think it was answer every email.

Right, right.

Which I wasn't good at. And now I am a little better, but it's—

But you don't know where these things lead to.

And build the relationships. Build the relationships. And don't build them just to be transactional.

Right.

That's the big part.

Totally. So another relationship, Mike, that I know you talked about is with Jonathan. So you two are co-founders in work and life, but you also You also had another co-founder.

Yeah.

That you, that didn't go so well. And so tell us that story.

Yeah. So we didn't, you know, this book is our cheat codes. It's raw, it's honest. And I had a—

Love that.

I had an epic failure and there were two pieces of information we didn't know how to handle. One was my dad had massive mental health issues with his business. It led to some bad decisions, bankruptcy, and I learned a lot about mental health. Health. I covered it from my lived experience. It's not my story to tell, but how it impacted me at 13 years old with your dad in the, you know, hospital for mental health issues kind of like leaves a mark. And the other is I started a company with a friend who is an artist, Jonathan— Jonathan Kramer, a very successful artist. He sold, you know, his paintings for over a million dollars. He makes incredible sculpture, and he invented a new language, and it was a language based on the 8 basic shapes that populate the world. And he dissected them, put them together, and it's 2D and 3D and numbers and has applications in cryptography and all these, like, and I love it. I mean, I helped him for years, and after Salesforce, I had enough, I think, hubris to think that, oh, I could do this, right? We don't know who the customer is. We don't know if we could work together. We don't, but I can do this, right? 'Cause I'm a successful entrepreneur and we raised $12 million and we've worked on it since 2017. We're still working on it. I left the company 'cause we couldn't work together. We didn't talk about whether we were a fit as co-founders and turns out we're not. And it's his system, so I left, but it's been a huge failure. And who you pick as a co-founder is more important, I think, in many ways than what you decide to do. You could always pivot the business. It's very hard to pivot a co-founder.

Yeah.

And if you don't get that right, you're screwed. And it showed me how lucky I have been to have this lady as broad— as broad as my, like, best friend, lover, and business partner my whole life, right?

Yeah. Yeah.

Like it's truly a, another lucky gift that I happened to go to this wedding that we met.

And are you, do you have tears in your eyes again?

A little bit.

Aw, that's sweet.

It's really cute, Mike.

Yeah.

No, it's true.

You really feel it. Yeah.

Oh my gosh. He's very sappy. It's very cute.

I think that's very sweet. And I think that, you know, the notion of like really finding your, like your beloved, really. Yeah, yeah, I think that's so sweet.

And it's, it's where people's misery comes from. Yes, they pick the wrong partner.

Oh, big time.

And then when you pick the wrong partner, you don't perform at work.

Yeah.

And now you're like miserable at home, you're poor, depressed. Like, that stresses me out.

Yeah.

And so like whenever someone goes to get married, I'm like, are you sure? Like, double check this, right?

I actually, in my book From Start-Up to Grown-Up, I have a co-founder up.

Mm-hmm.

So, because I, you have to really talk, like I, what I say, and I can know you guys can relate, is that when you have a co-founder, you have a marriage. It is. It's either gonna be a good marriage or a bad marriage, but you need to talk out some of these difficult things in advance before you make that commitment.

Especially like work ethic, why you are doing this. Like, what do you see happening? Like, do you see you yourself doing this for a year? Most companies take 10 years to have some kind of meaningful exit. You have to have all that.

Yeah, it's so true. So how do you have those conversations? What advice do you have for both of you, either of you?

We always tell all the founders that, you know, I do a lot of the due diligence for our investment deals in terms of people. And I often try in very kind of sly ways to ask those kind of questions to each of the founders just to see if they're on the same page.

What kinds of questions do you ask?

So, well, I don't wanna give them away because then they'll actually—

They're all in the book.

They're all, well, they're mostly in the book, but like I'm trying to basically figure out where their headspace is.

Yeah.

And if they understand that this is not gonna be a quick thing, just because AI's out now, totally. Or like social media was out or the internet was out in all the different decades we worked, it doesn't mean that there's gonna be like a 2 to 3 year turnaround and you're gonna like make a ton of money. I wanna see that they know what they don't know and I wanna see them ready to, to shovel, right? Mm-hmm. To do the hard work every single day. Mm-hmm.

And so big for you is work ethic.

Yes.

They have a matched work ethic.

And, and no, I don't wanna hear shortcuts. I don't want to hear someone who's always trying to find a shortcut. There are no shortcuts in entrepreneurship. You have to do the reps. Like, we didn't do this in 3 years. We've done it in 30 years.

Yeah. Yeah, for sure.

But I think the biggest— I think the biggest co-founder question is, tell me what you two do. Oh, sure. Because if there's overlap, it's an immediate red flag. So if you have 2 engineers you're gonna be fighting about, oh, do we use like this technology or this? Should we build this first?

Or the roadmap, you'll be like, yeah.

So we really like when there are two people who could cover a lot of ground, 'cause you're gonna have to do a lot of stuff.

Yeah.

And so if I had to do all the incorporation, all the legal work, all of like the HR stuff, it would've taken me away from the customers, the product, the raising the money.

Which is what your skill set is.

Yeah. And then what I got wrong with Jonathan then was basically, how commercial do you want this to be? This was his invention. Is this a research project or a company? How hard are you going to work? You know, she was also doing art and, you know, these things take focus.

Yeah.

And what are some of the values that are important to you? And, you know, for me, I could list some, like, really— we've talked about it, right? Like hard work, Transparency, trust. Like, if Cass— I say to Cass I'm gonna do something, it's done until she reminds me again. But like, you know, it's basically, will you do what you say you're gonna do? Yeah, at the highest level. I'm not saying I forget some stuff. And you had— we never had that conversation, Jonathan and I, because we were friends for a while. We liked spending time together, and it led to not only a lost company but a lost friendship.

Yeah.

He's not very happy because we did have a prenup and the prenup was that I control the budget 'cause I'm raising all the money. He has veto rights over some of the technology decisions and, you know, it forced me to make some decisions on the budget to save cash, which weren't, let's just say they weren't popular decisions, but they were important.

Yeah, totally makes sense.

Right.

My prenup is more about having those questions around values.

Oh yeah.

And around work ethic.

Yes, yes, yes, yes.

You know, what happens if someone's scaling and someone's not scaling and those kinds of things. And I think it's so important but very challenging to have those conversations in advance.

It's awkward. Well, it's like basically getting married without knowing, like, are you gonna have kids?

Right.

Are you gonna raise them a certain religion? Do you care about religion? What about money? How do we wanna split our finances?

Totally. And when you have a co-founder that works, do a lot of companies with them. Like, seriously, don't— like, it's very rare to find a co-founder that you'll spend all your days with that you like, that you're successful with.

That's true.

And the other concept that I really like these days is do stuff that you know. So, you know, I have a friend who's done a bunch of customer service software and they did like 3 different versions.

Great.

And they kept selling one to Salesforce and then build a new one and a new one. And that's a pretty good model. Work with the same people, do kind of the same things, and good things happen.

Yeah. Is there anything else you think about? You're wearing a Liquid Death cap because that's one of your invest— investments. I know you also invested in, I think it's Scopely, which was sold for, is it right? $5 billion. Not a bad day's work on that.

What, what else?

When you, how many investments do you have? Like you have like 100 investments. At least.

Yes.

A lot.

A lot.

100 in like tech.

Yeah.

Or like venture.

And are you on the boards? How does that kind of work? How do you handle investors in terms of like picking deal flow? I can imagine, but like picking what you, who you wanna invest in and then how you kind of organize yourselves.

So we get deal flow 'cause we're entrepreneurs.

Sure, that makes sense.

Our reputation is based on doing stuff. So do we help you hire? Do we help you market? Reorg? Do we help you build a marketing team? Like, we're not going to do the work, but like, and so we take a lot of pride in being able to accelerate them. Like, oh, we have a great person. Like, you know, there was one of our greatest employees, Miles Klieger, was one of a— there's a customer and then one of our sales leaders and we'd invest in this company called Appboy. And Appboy's a great company. They rebranded to Braze. Right as they were rebranding, they were looking for like a go-to-market head. And so I helped recruit Miles 'cause we'd worked so well together. We were an early investor in Mark Gourmizian and his company. And like that is so helpful for a company. It's now a public company. It's a $5 billion public company. Miles is president. He built the whole like go-to-market thing at the company, the whole org. And that is like, we believe it to be God's work. Like if you can help entrepreneurs move faster by getting the best people, if they get an offer, how do we help get multiple offers? How do we help them fundraise? How do we help them lay off people?

Lay off people.

We've done a lot of like layoffs. And so we get deal flow from reputation with co-investors and with entrepreneurs. So the best ones They're like, when an entrepreneur's successful, they come back.

Right, right.

Or like, yes, like that's someone we want it back. And we outline in the book something called the Go Gauge, which is a very simple framework we use to look at investments. And it comes down to what's the product, why is it different? You know, so it's gotta be somewhat different. How are people gonna find out about it? A lot of, a lot of people don't really Talk about marketing. How are you gonna distribute it? How many— I skipped how many customers there are. We don't like market size because it hides a lot. We like how many specific customers are there and then multiply it by like average revenue per customer.

Yeah.

We got, I remember in the golf.com deck, it would, I say huge industry, $80 billion. We didn't own a golf course, so that's $60 billion of it, right? We didn't know owned a golf club manufacturing facility, so that's another $8 billion. We didn't sell golf balls, so like our market was actually very small, and smart investors knew that. That's why we got 100 nos. So we look at very— like, it's hard to build a big business without a lot of customers who could buy your product. And then the final one, the sixth, is do the finances make sense on the back of a napkin? Not like a huge financial, like, kind of—

Like unit economics.

But like, does it make sense? Does it pass the smell test?

Yeah.

Because you're gonna, especially early stage, you're gonna definitely pivot and figure out your pricing with customers. But what we know is if it doesn't work in a spreadsheet to begin with, it probably will never work. So does it kind of smell right?

Yeah. Yeah. That is really helpful. And that is in the book, that framework.

Yes.

The Go Guide, the Go Framework. You know, it's crushing to me that we're running out of time and I wanna make sure—

I'm free till 9:00 PM.

I appreciate that we might keep talking. I want to ask you my final traditional question.

Okay.

So 3 questions and you guys can take them together or separately.

Okay.

Have you ever suffered from imposter syndrome or severe self-doubt?

Yes, I do it all the time. Yeah, all the time. Sometimes I will catch myself in a meeting where I'm giving a really smart entrepreneur, someone who's way smarter than me in an industry that I know nothing about, some kind of advice on a process, on operations, which yes, I have expertise in. And then it'll hit me that like, why am I the one telling them this? They're so much smarter. Happens all the time. Yeah.

How do you handle that?

I think it's grounding and kind of deep breaths and just remembering that, you know, when you offer advice or your help, like that's where I feel like sometimes, you know, I gotta remember who I am. It's very specific. I, I'm never gonna say I'm an expert in X, Y, and Z. I'm an expert in starting companies and running them.

Mm-hmm.

Okay. And, and pickleball maybe. And so pickleball for a 55-year-old.

Mm-hmm.

But, but that's it, right? And so I think that's what does it is I just kind of reframe.

That's That's helpful. How about you, Mike? Did you ever experience imposter syndrome?

I did at the beginning. I remember at UWire, I was a student and I went down to meet with the Chicago Tribune and I'm like, why would they ever wanna work with me? Some of those people I met with, I'm still in touch with. I quickly learned that everyone's kind of making it up.

Yeah.

No one really knows anything. It's so true.

It is.

It is so true.

And like, and I learned that because, yeah, we were doing internet stuff before anyone knew internet stuff. And I remember talking to USA Today and being to Ray Keene. I don't know if you remember him at USA Today. And I was like, they really don't know anything about the internet. Like they don't know, they know how to print an incredible newspaper.

That's right.

But they know nothing else.

Right.

And so it's kind of, I think entrepreneurs need to realize that no one knows anything until they know anything.

And they gotta jump.

And that's not a reason not to get started.

Right. That's beautiful. What, and this is a question for each of you, what do you wish you had known earlier on your journey?

I think I wish I had known what I know now, which is you are never going to be able to give it your all in every single area, your friendships, your family, your partnership, and your kids. And I think the immense guilt that I had at all times thinking that I was failing in all the other areas. I think what you realize as an entrepreneur is you can only do one thing well at a time, and you're gonna have different phases where you're gonna be able to give that, that unbelievable amount of intense focus in different phases. And that's okay. And I, you know, we have 3 amazing kids who we were convinced were suffering the whole time, and they're actually great. That's really great. And they got to, they got to see you know, their mom work really hard.

Yeah, for sure. Yeah. Mike, how about you? What are you issued on earlier in your journey?

I think I've turned focus into a superpower and I've wasted a lot of time because I get excited. I go down rabbit holes and very rarely do I come up with whatever rabbits are looking for in rabbit holes. I don't know what the purpose is.

We never really know what rabbits are looking for.

I know.

But whatever.

That's a very good question.

So I come up and I'm like, oh yeah, that didn't work. Or even worse, I'll launch a company without telling Cass, which I've done. And then I'm like, why? Like, I'm such an idiot. Like, I just spent $5 grand on the corporation and like, I bought all this stuff. I'm now maniacal with the companies we work with about like, what are your top 3 priorities? How do you know that you're gonna— how are you gonna know that you were successful? What are those metrics? And that to me, it's what it's all about. Are you focused on the right things? Are you focused on too many things? 'Cause it could be the right things, but you just can't do 'em. And are there things you should be focused on that are gonna bite you in the behind if you don't focus?

That's great. That kind of brings us to the last question, which is what advice do you have for other founders as they embark on their journeys to grow into leaders?

I would say the first thing is, you know, radical transparency, that information is your friend and there should not be a wall between you and your team. You have to, you just tell them the truth, tell them the good, the bad, the ugly. No surprises.

Love it. Mike, what about you?

I don't wanna sound self-serving, but I, every company that we invest in will get Shoveling Shit: A Love Story.

Mm-hmm.

Because we realized that it was these lessons that helped us build confidence. With confidence, you will make better decisions. You'll be able to tune into your gut and the data. And there are 50 cheat codes that we used, that we learned the hard way, most of them. And if you can build that confidence, you can then operate in this world of fear, uncertainty, and out, which will always be there, you'll never get rid of. And you'll not only be confident at work, you'll be confident at home because you'll be able to prioritize things without saying it's either or. Which, we're not saying you can do everything at once, but you can do anything that you prioritize. And if you don't prioritize certain things like relationships, your health, they will disintegrate. Great. And so in the book is kind of not only how to build businesses, but how to build a life that you actually wanna live, which I think's even more important.

Love it. The cheat code, everybody. Shoveling Shit: A Love Story About the Entrepreneur's Messy Path to Success. Pick it up starting in June and you're gonna really benefit from it. You guys, thank you so much for joining me.

Thank you for having us. Thank you.

Loved it.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.