#93: From Startup to Grown-Up: Kass and Mike Lazerow, Serial founders; co-founders of Buddy Media (sold to Salesforce for $750M) - How to survive a failed acquisition, stay married to your co-founder, and enjoy the journey of entrepreneurship.

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 Grown up. My name is Alyssa Cohn, and today I'm thrilled to welcome a dynamic duo to the podcast, Cass and Mike Lazzaro. Cass 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 three kids, a pretty amazing feat. In addition to being serial entrepreneurs, Mike and Kaz are also angel investors who have invested a lot of companies, including Scopely, which was 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 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. 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 Cass and Mike Lazzaro. Cass 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 going to say it. Just going to say it out loud. Shoveling shit. A love story about the entrepreneur's messy path to success. And I want to start by asking each of you what.

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 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 entreprene.

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 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 Cass 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. And. And 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 because you're married, you're. You're not immune from the challenges.

Exactly.

For that. That plague co founders. And in some ways I'm sure it's even more stressful. So I definitely want to talk about that. But before I do, I actually want to 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, before you even dating? Yeah. Tell us about that.

So I had opened up the interactive arm of an agency before. So I was very young. I was probably 24ish. 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 Owned 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. By the way.

Polite of them.

By the way.

I went to journalism school at Northwestern University, McDonald's 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, want to start a business, 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 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 Startup to Grown Up. I sort of tell people I wanted them to avoid unforced errors.

Yes.

Especially in the talk of leadership.

Were you a tennis player? No. Unfortunate errors is a big term in the tennis world. So I thought maybe.

Oh, that's fascinating. Oh, yeah. Tell me more about that. You were.

Yeah, 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 unforceres. It's the same thing as missing putts in golf. Like you're, you're, you're trying not to, you're trying to basically not have yourself lose the match. Right, Right. So I think that's what you're saying.

Exactly, exactly. So the two of you were obviously entrepreneurial and then you started dating. And wasn't it that you had started golf.com so what. Tell us about the sort of the coming together of Golf.com and then we're going to get to the dramatic, the dramatic finish.

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. 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 because 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 had 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?

So our company started off as Golf Serve, and then a couple years in, we actually got the right to buy the domain, which was like, great because domains meant something back then.

Totally. How much did you buy it for?

What was it?

$289,000.

Wow. Okay. As opposed to the millions? I mean, we were willing.

It was actually part of an auction process. Yeah, 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. Can we just do that? That just hacked because we knew how valuable it is. It was being Sold by NBC. So think about that. Like, they were broadcasting tour events, and they were basically saying, we don't think the Internet's going to be anything.

Totally. They were voting 289.

Exactly. Like, why do we need this domain, One word domain of a popular sport.

That rich people play right before behavioral targeting.

I'm going to bookmark this because I want to hear the story of golf.com but I just want to 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 want to talk about that later. But I want to 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. So you could 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 USG handicaps online. And you could book tee times, you could look up courses because, you know, golfers are fanatical. They want to see the course, the slope, the rating. They don't see how hard it's going to be. And so we provided this content on our site, but then we took the content and syndicated to all the large, like, newspapers out there.

USA today dot com.

Yeah.

Use their 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.

Yeah.

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. Wait, wait. But before we get there, it's like you were. This was your idea 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 you're young. I was 22.

I definitely didn't think it was wrong. I just was like.

Didn't think. Yeah.

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 for you to get business together. 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.

Year and a half. Incredible.

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

1999. Yeah.

December 23rd, 1999. We'd been married three months to the day. And myself, Mike, and our other co founder, Mike Casper, we all were like, wow, 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.

The moment.

And the deal was closed.

Yes. And our board said, like, all stock. This is what we want to do.

Yeah. And you were, like, living the dream.

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

Yeah. So that was like, you were. Everything was happening. But then you got a phone call, a faithful phone call. What happened?

So it was March, and I got a phone call.

It was three months later.

Three months later. And we. And just so you know, in those three 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 excited because it'll be, like, one of the first times we actually get paid. 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 problem 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? Because 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 up. Big financing and the finances.

They chip shopped.

Chip shop.

So they had a little money when we did the deal, 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 in sales at the same time. The environment was like AI meets Taylor Swift in terms of the Internet. People were losing their mind. Anything with a dot 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 dot com. They were multi billion dollar companies. And so we're like, oh, chipshot.com, golf. Why aren't we going to be a multibillion dollar company 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 have 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 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. Kind of stuff hits the fan. I can say it. Shit hits the fan and you deal with it. 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 of. Were you gonna say something else?

Well, I was gonna say, like, I think I. I know Mike's mind. I. 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?

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 and they pulled up.

Oh, they definitely did.

Yeah.

Yeah.

Like, complet.

And also, I mean, I will 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. Yeah, 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 real. We should have been looking at the landscape, and that's important.

We were just kind of like, flying high. 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, 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 horses. 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 nothing, and raise more money, which was not gonna be advantageous to you, and rebuild it?

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

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 is a few years before this, and fixed the vsd, noticed the valve damage, and eight days after that surgery, my aortic valve burst. You need your aortic valve without the aortic valve.

Essential.

What happens is the oxygenated blood goes back into the heart, and you're pumping unoxygenated 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 while you're getting surgery. She's like that. Love you, Nancy Zirkin.

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

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

And I've questioned her a lot over the last 30 years, 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 Svrestasi didn't go out, everything.

And I was, like, happy afterward. Like, I had a girlfriend at the time. I told you that, you know, she was kicked out of the hospital because, like, 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 going to 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, and not one walked out over those three months. So we didn't pay people for three months and they stayed with us.

Why do you think that is?

Well, I think it's relationship based. You know, 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 going to 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.

Yeah.

Then you just kept pushing yourself. And I think that some of those employees really love that.

Yeah, I can see that. And so you, you went and told the employees.

Yeah. And then you hit the road.

Hit the road.

But telling employees is a huge lesson that we took for. Because. And I remember Cass said, we have to let everyone know. And first I'm like, oh, 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, no matter how bad. And so people are okay with bad news. Especially in the innovation economy, people are not okay with surprises. So if all of a sudden it's payday and they're like, hello, where's my money? Like, oh, sorry, it's coming. Like, no, 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 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 this? It's going to 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, 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. And she's also a cicada. She emerges every 17 years with atheists. But, you know, there's a lot here.

Yeah, I'll give you a chance.

Yeah, yeah, yeah.

But I think, you know, Cass as a leader, made decisions, 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, like, that was all private. But, you know, we would come out of meeting, we had very small offices, and we'd have investors come in. And I would remember, I 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 two 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. 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.

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 going to le.

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 serve. I'm sorry, Golf.com board. After we raised all the money and we had Matt Serovich talking to us. And I remember it very well. I was sweating.

He's a New York hedge fund. We're very scared of him.

We were very scared of him and his wife.

Now we're friends with some of those.

Creatures and Jeremy Minaj. And they were asking about the company and I went through all the details and then he 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 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.

This is one of their book chapters, guys.

Yeah. And it became actually a motto going forward where like, if it's bad news, set that, say it's bad news. 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 going to do about it. You can't try to 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 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 a hundred percent. So. Ok, 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 in.

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. 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 a million and a half to get restarted. Everyone else said no. So we got like, a hundred no's. 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. 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 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? The time happened to be right for golf. That's fascinating. So how did you exit? How did you ultimately resolve that?

So 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 want to reach golfers. And he would be going up against Time Inc. That owned Golf Magazine and they owned Golf Online and Conde Nast and Conde Nasty and golf. And he would win on all the bids. And so they were 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 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, Bumblebee. Yeah, we love Julie.

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

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

Right.

We got down to four 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. I was having babies. And Mike, you had two babies during that period. Yes, right. I did. 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 want to also clarify for everybody who doesn't remember, like, there was that dot com bubble in the dot com bust, right? Nobody was advertising anymore. No one was like, the Internet's over.

Yeah, that's like done.

Amazon bomb, right?

Until like 2003. 4 for the ad business. And we. And our revenue, we cobbled together a few million bucks. Right. Like, I think our biggest year was like two and a half million, three million.

Do you remember when I had to go, we were watching paycheck to paycheck and watching 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 everyone was holding onto their payment. Yes. Because it was.

So that's what show up at offices.

Say, I'm not leaving until get the check paid.

You dislike me.

I totally respected that.

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

Yes.

It was like I had to go fly in to get money. 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 have thought it like I was a quitter. I think I was really tired. I mean, I just had our second 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 gonna keep going.

Yeah, tired and just don't quit. You just.

You just keep doing it, 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 see what we're going. Like, look out for land. We've gotta 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. 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.

Does all the work. Paddle, 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 to. Him to.

I wanted him to say, land the plane. Yeah, he land the plane. And also, you know, 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 three 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. But you seem to. 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? And 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 uire. 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. 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. There was abuse, there was guys doing the stuff that guys do, and it was just not great. What Mark, I think really honed in was this idea that everyone, Zuckerberg, everyone wants to belong. Everyone wants. 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 24, 2007 and said. And called on developers to build applications using the social graph. And I immediately said, this is a new Internet 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 have talked to her earlier, but she was delivering C sectionally 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. Nicole was very cute. Miles got a little banged up.

Yeah, he's a little banged up. But they're all fine now.

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 cheeses.

She hadn't eaten in nine 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. Three 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 cast. 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 decision because I think she also saw Social media as a new trend that was just about to happen 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 the social Internet or whatever 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.

And at the time, 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.

Hachette, the publishing company?

Yeah, yeah. And Mark went on to do Zynga.

Zynga, the 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, or I used to be. She thinks I don't work anymore.

No, you can't outwork me.

I can't outwork Cass. Cass is a monster. But two of you 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 supposed. 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 want to come on and, like, use it. And I Don't think I really thought it made any sense.

Sounds like an early bitcoin. Early crypto. When you say currency, I mean, it.

Was more of like, Amex points for Facebook.

Okay. So that's like crypto.

But we didn't understand kind of monetary policy and there became massive inflation and no one wanted our currency. And. And we just kept having conversations with companies and they said, we think Ace Bucks is what it was called, is an awful idea, but help us with Facebook. We want to figure this thing out. I remember meeting with HBO and a bunch of media companies were first 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 Cass is like. Like, Cass is like, you guys can't sell this anymore because it's not scalable. I can't find enough programmers to do it. We're building one off.

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 were talking. It wasn't just my idea, you know, in years. He was Eric Hippo, who at the time was. Was working for Softbank. Now he's at Layer Hippo 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, message, something.

Yeah.

You know, do a sweepstakes, like, all these things that we were doing. So we. We invented something called Saplets, 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 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. We didn't want to be a WPP company or a Publicis company or an Omnicom. We wanted all of them. 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, so we didn't have to be heavy services.

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. Rebranded.

Yeah.

YouTube.

I've heard of that.

And if you think about it, like Unilever. Right. Think about how many different brands they have and then 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 nine out of the top 10 Fortune 500 brands.

Got it onto Facebook 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.

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

Yes, 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.

She was great.

We'd never scaled a sales team. Her. Her whole career was building armies of salespeople. And so we wouldn't have done it just as an FU to Salesforce, even though I like that idea. 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 flying out there, having dinners, getting grown up.

Clothes.

Yeah. Cats had to get out of sweatpants. Susan, if anyone knows Susan St. Leger, one of the great executives, she's gone on to do even much bigger Kashi Corp and others. She dresses incredibly well. She wears a lot of Chanel.

Yeah, we all have to up our game sometimes.

Yeah. And so we, we're still scared of her to this day. But what happened and is 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 had 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, who 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 the 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 love Salesforce. We still do. Love Marc Benioff, love the team. If you're in software, that was and is the place to be. 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 launch 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 fit into the portfolio. Yeah, yeah. But I still, I have to say I don't think that you wake up every day and leave a hundred million dollars on the table.

You know, so we, you know, as a board, you have fiduciary obligations, 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 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 Department of Justice.

Oh, 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 three years from time we started selling the product. We got to 50 million of annual recurring revenue with nine out of the top 10 global marketers. And these marketers are paying 5,000amonth. 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 Search. Right. Google was it. There's. There was no Bing at the time. They were 100%, basically market share, a little Yahoo. And. 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 dangerous.

The momentum is totally.

And there's zero risk in. In Salesforce.

Yeah.

They don't own anything in marketing.

Right. That was just going to work. That makes a lot. This was more pragmatic. Yeah. You know, Cass, I think you said in the book that part of why you thought about this acquisition was that also it was 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 three when we started. So Viv had just been born, and Cole was three, and Miles was five. So we're doing this now five years, and we are barely there. Right. Thank God. We had incredible babysitters, but we are barely there. And it's taking a toll. Bigger kids. Bigger, 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, principal's 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.

Yes. Which, for the record, is way harder taking care of kids than any job. It is. It's just.

Yeah, totally. So. Right. So you just realize 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. Is because we have been there for the last 13, 14 years consistently since selling Buddy Media, we've noticed that they actually have learned some things from us. And what we've done is led by example. We could tell them eight times out of ten, every single day, 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. For. Was it three and a half years? Four?

Yeah, close to four.

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. He's trying to make their life miserable. I'm going to pay you a billion dollars and make you miserable. And Mark, he gets off on philanthropy, the one, one, one model, 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, I want you here. Come to me if you're not happy. And. And I was happy. I did what I wanted to do. I moved around. I was chief strategy officer. I headed up 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 going to die if I didn't get in better health. So I was like, at Salesforce, there's no first gear, second gear. It's like, oh, Unilever is not happy. I'm flying to London, right? I'm going to dinners every night. I'm like, having drinks before they're in New York, before they had 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, why me? 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 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. The business would have 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 because I don't think we would have probably pivoted, but the business we had would have 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 two years, four years, whatever it is, inside the larger company?

It's very hard. And I actually don't talk about it a lot because 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. You're going to work with these people over the next 50 years of your career. You're going to need stuff. You're going to help them out. Do not carpet bomb anything. You're going to 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 over communicate 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 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 banker dinners and conferences. And I won Ernst and Young Entrepreneur of the Year. We laud entrepreneurs. We put them on pedestals. And then you're just another worker. And so you just have to 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 four years about how to focus on organization, how to lead, how to communicate, how to communicate to investors. I was one of the kind of investor relations people in New York because 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. So, 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.

Totally.

Because you're not worried about, like. Like, we were always worried going to a payroll.

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

And like, hr, like, just 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. And did we want to 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 million. What was it like to have money like that kind of money, like, genuinely, as we say, fu. 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 into that money?

Well, we both kind of grew up on third base. First of all. We did because you know, we had all of our education paid for. I was able, a very trained athlete. So that meant lots of lessons and coaches and mental coaches. So I did have the opportunity, you know, upper middle class family. But when we started everything, like we started dating and moving in together, we didn't have anything. And the only thing that we had, 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, you are when it was acquired by Student Advantage. That also hit the tank when. And 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 because we had not really had any real vacations and we couldn't afford them. 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. So we've gone really, really long into giving, especially cycle for survival.

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

Yeah. So it's weird. The first year is 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.

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 part of it is like an expectation Some people, oh, like they're super rich. They're going to 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, it's all like their. 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. Which we realize is a luxury because most entrepreneurs, if they're on Instagram or TikTok, they're like, cutting it up and doing it themselves.

For the record, I myself do it myself.

Yeah. So I think we, you know, it's kind of like we're at an event with Gary Vaynerchuk, 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. And I remember that was such a dull, 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, 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. You need someone to tell you no. And if you don't have someone to tell you no, liquidity's low. You could 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 have done.

Right.

But all of a sudden you're talking Real money. And especially in New York City. Right?

Yeah.

Because talk to anyone in New York City and even the people living in $50 million townhomes think that their place isn't big enough. 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 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 was. 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.

You were invited to a lot of things.

Yeah, yeah.

And let's just say we had probably 30 to 40 invitations to gallows 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. I know it must be that your. That your marriage affects your businesses and your businesses affect your mar. Yeah, talk about that interplay.

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

Cause you bought a minivan. Yeah.

Well, I love. Listen, 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. So it's just been a perfect yin yang, complimentary skill set and life in that sense. And people always say, oh, well, who does this? Well, Mike's VP of religion. Right. 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. 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 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 team sports.

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.

But 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 part of.

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.

Oh, yeah, 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. 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 Fish. 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 really 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. Same lane.

You gotta go there.

Yeah, same lane.

So same lane. And I think Mike would say, so 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. And podcasts seem like a lot of work.

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, it is. And so we wanted to do this, and I had kept of the truth.

Well, 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 in my mind. It's like, oh, you're writing a book.

Well, wait, but you know that 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 companies.

Like, rather than having division of labor. Cause 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 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 that was the beginning. You have to understand. I'd kept all the lessons.

Feedback.

I kept.

Okay, what? Like.

Like, I had kept all the lessons over the last, you know, 30 years.

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. 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 do it, and we 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. Because we kept trying to figure out how to share it. And then after that, we. We ended up writing it in three and a half months.

Yeah. Yeah. So kind of once you find your rhythm.

Yeah, we got a chapter.

Yeah.

And then no one sells books. There's no, like, agents here, so you have to sell the book yourself. So then we're like, okay, now we have a third job.

Then I'm like, yeah.

I mean, when you say no agency, I mean, that's the whole thing. You write the book and now, wait. No one tells authors that you have to now go promote the book.

You gotta go, and you have to.

Figure out how to get 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 that.

I mean, listen, I think things would happen with Gary though. He has a huge audience and a.

Sure.

A whole army that if he press 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 actually do things about and who are the convenient friends. When one of our friends buy, like writes a book, we buy 100 copies.

Yeah. Because now you know what, it's how important it is.

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 three hour live stream 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. 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, Rachel and Jackie. 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 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 Birth by Columbus Circle.

Yeah.

So the more you give, the more you're going to 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 relationship 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. You also. Also had another co founder 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. 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 hospital for mental health issues kind of 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 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 eight 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. 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, because 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 because 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 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.

Are you. Do you have tears in your eyes again?

A little bit.

Aw, that's sweet.

It's really cute, Mike.

Yeah, it's true.

You really feel it? Yeah.

Oh my gosh. He is 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 Startup to Grown Up, I've co founded pretty prenup. So because I. You have to really talk like what I say and I can do you guys can relate is that when you have a co founder, you have a marriage. It is either going to be a good marriage or a bad marriage. But you need to talk out some of these difficult things in advance before.

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

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 want to give them away because then they'll actually.

They're all in the book.

Well, they're mostly in the book but like I'm trying to basically figure out out where their headspace is and if they understand that this is not going to be a quick thing just because AI is out now. Totally. Social media was out or the Internet was out and all the different decades we worked, it doesn't mean that there's going to be like a two to three year turnaround and you're going to like make a ton of money. I want to see that they know what they don't know and I want to see them ready to shovel right. To do the hard work every single day.

So big for you is work ethic.

They have a matched work ethic. No, I don't want to 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 three years. We've done it in 30 years.

Yeah, yep. For sure.

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

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

So we really like when there are two people who could cover a lot of ground. Because you're going to 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 have 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 in 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? He was also doing art. And these things take focus. And what are some of the values that are important to you? And for me, I could list them. Really. We've talked about it. Hard work, transparency, trust. Like if Cass. I say to Cass, I'm going to 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 going to do at the highest level? I'm not saying I forget some stuff. And 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 friend.

Yeah.

He's not very happy because we did have a prenup. And the prenup was that I control the budget because I'm raising all the money. He has veto rights over some of the technology decisions. And 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 and around work ethic and what happens if someone's scaling and someone's not scaling 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.

Yes.

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 friend who's done a bunch of customer service software and they did like three 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 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 a hundred investments at least. A lot.

A lot.

100. Like tech 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 want to invest in and then how you kind of organize yourselves.

So we get deal flow because 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. Who's a customer and then one of our sales leaders. And we'd invest in this company called appboy. And appboy's great company, they rebranded to Braze. Right. As they were rebranding. They were looking for a go to market head. And so I helped recruit Miles because we'd worked so well together. We were an early investor in Mark Girmizian and his company. And that is so helpful for a company. It's now a public company. It's $5 billion public company. Miles is president. He built the whole Go to market thing at the company, the whole or. 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 are like when an entrepreneur is successful, they come back.

Right?

Right. Or like yes, like that's someone we want it back. And we outline in the books on how to go gauge, which is 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 people don't really. We talk about marketing. How are you going to 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. We got. I remember in the golf.com deck it's a huge industry. $80 billion. We didn't own a golf course, so that's 60 billion of it. Right. We didn't know own a golf club manufacturing facility. So that's another 8 billion. We didn't sell golf balls. So our market was actually very small. And smart investors knew that. That's why we got 100 no's. 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 six is do the finances make sense on the back of a napkin? Not like a huge like financial like unit economics, but like does it make sense? Does it pass a smell test? Yeah, because you're going to especially early stage. You're going to 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 want to make sure. 9:00pm I appreciate that we might keep talking. I want to ask you my final traditional question. Okay, so three 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 got to remember who I am. It's very specific. I'm never going to say I'm an expert in X, Y and Z. I am an expert in starting companies and running them. Okay. And pickleball, maybe. And so pickleball for a 55 year old. But. But that's it. Right. And so I think that's what does. It is I just kind of reframe.

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

I did at the beginning. I remember a U wire. I was a student and I went down to meet with the Chicago Tribune and I'm like, why would they ever want to 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 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. It's Ray Keel. 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, 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 got to 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 unbelievable amount of intense focus in different phases, and that's okay. And I, you know, we have three amazing kids who we were convinced were suffering the whole time, and they're actually great. That's really great. And they got to see, you know, their mom work really hard.

Yeah, for sure. Yeah. Mike, how about you? What are you shooting 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 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 Cas, which I've done. And then I'm like, why? Like such an idiot, I just spent five 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 three priorities? How do you know that you're going to. How are you going to know that you are successful? What are those metrics?

And.

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? Because it could be the right things, but you just can't do them. And are there things you should be focused on that are going to 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 and to 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 want to sound self serving, but I. Every company that we invest in will get shoveling a love story.

Mm.

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 doubt. Doubt 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 want to live, which I think is 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 going to really benefit from it. You guys, thank you so much for joining me.

Thank you for having us. Thank you.

Love to.

Thanks for listening to From Startup to Grown Up. 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, alyssacon.com.