JEFF BERMAN: Hey folks, Jeff Berman here.

I got a chance to talk to my very old and very dear friends Kass & Mike Lazerow on stage at South by Southwest earlier this month, and we wanted to share that conversation with you.

Kass & Mike are two of the very smartest, very best entrepreneurs, investors, and humans I know — and I’ve had the pleasure of watching them work, working with them for a very long time now. I was on their board at Buddy Media, the SaaS company that they built from scratch, from the ground up, and eventually sold to Salesforce for nearly $1 billion. And now Kass is on the board of WaitWhat, the company that makes this podcast. So we’re keeping this all very much in the family this week.

Kass and Mike are unabashedly honest about how hard it is to build successful companies — especially when your co-founder is also your spouse.

The Lazerows have distilled their most valuable lessons into a new book, which is coming out this spring. It’s called Shoveling $h!t – yes, Shoveling $h!t: A Love Story, about the entrepreneur’s messy path to success.

We talked about this “love story” live on stage in Austin, Texas as part of South by Southwest. And I started by asking Kass about the messiest parts of their careers. Their toughest business moment was back just before the dot-com bubble burst. Mike and Kass were newlyweds, and they were co-founders of the site and the business, Golf.com.

Inside Golf.com’s messy exit

KASS LAZEROW: We had sold Golf.com to Chipshot. And Chipshot worked in Silicon Valley, and they made custom golf clubs in the most expensive part of the world. We were bought on December 23rd, 1999, and we were psyched. This company was going public in the spring. We were our board had all voted for it. We were like, “Oh my god, this is the heyday of everything that you wanted for the internet.” Like, this was: eToys was going public for billions of dollars. And in March, I think it was March 3rd, 2000, we got a call that said, “Hey, I just wanted to let you know, this is from the president of Chipshot.”

BERMAN: So the deal hadn’t formally closed yet. You’d signed an agreement to sell the company to Chipshot in advance of their going public.

KASS LAZEROW: It was closed. It was fully closed. We no longer had control of our bank accounts. Okay? Every bit of money was coming from Chipshot. March 3rd, 2000, I pick up the phone. It’s the president of Chipshot saying, “I’m very sorry, I have bad news. We’re going out of business.” And I said, “What the f*ck are we doing here?”

BERMAN: We can swear, it’s Texas.

KASS LAZEROW: Okay, we can do it. Okay. So I said, “What the f*ck are you talking about?” And basically he said that Sequoia, who had backed them to go public, had pulled out.

And there was no more filing, and they were going bankrupt. And they’d be out of business in two weeks. And they had no more money to pay anything for us. Nothing for payroll. Nothing. Zero.

BERMAN: And, this was not a deal where you had taken a whole bunch of cash off the table?

KASS LAZEROW: No, this is an all-stock deal. We were psyched. We thought we had hit it.

BERMAN: And your team members were going to do well as well. Right?

KASS LAZEROW: Yes. Big time. And we own more than 50 percent of the company.

BERMAN: So, so set the stage for us. You are now in March. This call comes in. Where are you when the call comes in?

KASS LAZEROW: So we actually lived above our office. And when we got too big, we started bringing people up into our living room. And we were in what was the bedroom. So the three founders, Mike, myself, and Mike Casper, were in the back.

And just for the record, there was only one bathroom. So anytime someone had to go to the bathroom, they had to walk past us, which is incredibly embarrassing.

MIKE LAZEROW: It was the poop deck.

KASS LAZEROW:. Yes. It was basically a poop deck. And so we were sitting there in the bedroom part of this office, and I put it on speaker, and then Mike and Casper came by and they were like, we just started firing questions.

And I actually think there was an employee in the bathroom at the time that came out and was like, “Is everything okay?”

BERMAN: And the answer is no.

KASS LAZEROW: No. Immediately.

BERMAN: Yeah. So, you’re in the bedroom, you’re taking this call. It is a deluge of bad news. The sh*t is hitting the fan. You must have been personally devastated.

KASS LAZEROW: Yes, I think the first thing that came to my mind was all the employees, right? I didn’t even go to the all the investors, and we had a lot of friends and family as investors, but I immediately went to, “Oh my god, how am I going to pay these people? This is their livelihood, what’s gonna happen?”

BERMAN: What happens next?

KASS LAZEROW: The first thing is I had to calm down. I was angry. So I felt an immense amount of responsibility to everybody there. I felt like I was duped, right? So, of course, I’m the operator, so I’m the COO. So I’m going backwards. I’m like, okay, what did I miss in due diligence? What did they say to me? I’m looking through notes. And I keep looking, and Mike’s like, “Okay, okay.” And then I was like, “What are we going to do?” And he literally turned to me, and he’s like, “We’re going to start this again. We’re going to just start it again. We’re going to do this.”

BERMAN: So, Mike, where did that come from? I mean, I think most people would be spinning.

MIKE LAZEROW: Yeah, so it came from just this idea we’ve always had, which we didn’t know at the time, which was you just keep going as an entrepreneur. So as an entrepreneur, you show up to work, and sh*t hits the fan. This particular day, it rained sh*t, right? It was like, whoa. And what we have to realize is 1999, the frenzy around the internet was like Taylor Swift meets AI. Like globally, everyone’s talking about the internet. Etoys is doing like 100 million in sales, but it’s worth like 50 billion dollars, and everything’s going up and to the right, and we sold to a Sequoia-backed company, and we were, in our heads, very rich; we owned half of this company.

BERMAN: And on paper.

MIKE LAZEROW: On paper, yes. And so all of a sudden it’s, oh, we have no money now, which was fine, so we didn’t really have money at the time. And I remember sitting down, what do we need to do? And the first thing we need to do is raise money. And so, we hit the road with our partner in San Francisco, the Bay Area, which had very expensive hotels. So we stayed at a motel that had the thick glass bulletproof, but there were three of us in one room with our co-founder, which is like a little awkward. Cause we had just gotten married, we got married on October 23rd, 1999. We did what no one probably should do, which is start a company while you’re dating. But to us, I was 25, I’m like she’s really smart, she’s hot, she loves the internet, I’m all in. And, yeah, and I’m like, cross eyes, like bad heart. I’m like, okay. I was like, are you alive and like me? And we raised the money; you do what you have to do as an entrepreneur.

And we found the money. And the key thing about that, and Kass, who’s the operator, such a brilliant operator, she was so transparent with the employees and the team that we didn’t lose anyone even though we didn’t pay them for three months. We got lucky like a lot of this is luck, and we met a guy named Keith Bank in Chicago

And we raised $1.2 million or 1.5 million in one lunch.

KASS LAZEROW: In one lunch.

MIKE LAZEROW: Yeah, and that was like, such a key meeting. And we filled it in with a few others.

Our former investors in Golf. com, some of which were friends and family, just weren’t pleased with us.

BERMAN: I think that’s a bit of an understatement.

MIKE LAZEROW: Yeah.

BERMAN: What was the worst part of that?

KASS LAZEROW: The worst part I would say is that, well, first of all, I think telling our individual families that we lost their money and don’t forget that you have start-up costs when you start a company, and that comes from yourself, right? Unless you can take a loan or anything. But I think the worst part was that a very close family member sued us.

And just demanded the money back. And over and over again, I had calls. Then I got lawyers to tell him this is not going to happen — I mean, I don’t have any money to give you. It’s not even legal. And then he basically threatened to kill Mike. Which was pretty awful.

MIKE LAZEROW: Like why me?

KASS LAZEROW: It was a little odd that he didn’t threaten to kill me.

It was a little bit odd but at the time, I think I was just deeply embarrassed by that, like thinking to myself how does this happen? It was a good lesson in pick your investors wisely. And make sure that they can afford to lose whatever they’re putting in.

BERMAN: What happens from there?

KASS LAZEROW: We went back. I think the first thing that would that made like brought a little bit of joy was that I could hold an all-team meeting and say, “We’re back in business.” So that is like a feeling of just massive relief. So we did that, and we put our heads down, and you have to understand this is now 2000 — there is nothing, nothing living.

BERMAN: The 1.0 bubble has popped.

KASS LAZEROW: No one cared about us. There wasn’t a lot of business. We had to like limp along. We were mostly dead, right? But barely alive for seven years until the ad revenue business started coming back.

The initial vision for Buddy Media

BERMAN: You were able to sell the company, ultimately.

There are very few people who start one company and exit it and do a second company and have some success and notwithstanding the Chipshot-crazy, you did have a successful exit.

So, that’s two at that point, you’re married. You’ve got, I think two kids with one on the way, right?

And you would be understood for saying, “Well, I’m going to take some time off.” But you didn’t. You started yet another company. Why?

KASS LAZEROW: Well, it usually happens around the birth of every kid. And, he loves to think, like you said, in rabbit holes. And so, May 24th, 2007, Facebook announced that it was opening up its platform, and you could develop on it.

And so I get pulled out from just delivering our daughter, our third child, and we’re in the recovery room, and Mike goes, “I’ve got it.”

BERMAN: So you, just be clear. You’ve just given birth to your third child. It’s not three weeks later, you’re on the couch — you are in the recovery room.

KASS LAZEROW: I was in a lot of pain, and he goes, “I’ve got it.” And I literally think he is getting me sushi. Like he’s going to get me pizza and he’s going to get me sushi and this is going to be great. And I go, “Okay, where are you going to order from?” And he goes, “No, no, no, no, no, I know what we’re going to do next.” I said, “Are you f*cking kidding me?” And he goes, “No, this is it, this is it. You have no idea what’s about to happen. I know the next company, and we’re doing it.”

BERMAN: What happened in that moment? Where did that come from, and what was the thing?

MIKE LAZEROW: I knew about Facebook, about 200 million people on it. I was kind of fascinated, and Mark Zuckerberg gets on stage, says, “We’re opening up our platform, we’re exposing the social graph. Anyone who wants to can build apps on Facebook.” And this is back before Facebook had kind of impacted democracy and mental health and all the stuff. So it was like kind of a good thing for the world, we thought.

BERMAN: It was a simpler time.

MIKE LAZEROW: It was simpler time, and I just thought that like everything’s better with friends. But when Facebook recreated the social graph, that kind of the real life map of relationships, and you could put that on apps, it fundamentally changed the internet.

And we ended up launching a business that became Buddy Media, we didn’t know was gonna be a software company and had to pivot a few times. Would’ve never called it Buddy Media if we thought it would be a software company.

BERMAN: So, you talked about the company pivoting a few times. What was the initial vision once you got past kind of the space you knew you wanted to go to? Where did it start, and where did it get?

KASS LAZEROW: This is pretty ugly though.

MIKE LAZEROW: Yeah, so the initial vision was we want to bridge the commercial world, like businesses advertising with Facebook. And it took us, I think, four business models to get there. We pivot really fast. We love throwing away stuff. And so the first idea was probably the worst idea I’ve ever come up with in the history of ideas.

It was a loyalty platform for Facebook. And it was basically like Venezuelan currency, massive inflation, and it crashed and burned.

I remember going into HBO at the time. I said, “We can help you on Facebook. We got this thing called ACE bucks,” and they just like laughed, but they said, “Can you help us deploy our content on Facebook?” And we heard that enough times. So we said, “Okay, we’re going to pivot into software to help the largest brands in the world.”

BERMAN: I think is a really important moment in the story, because you’re out pitching one thing. The market’s giving you feedback on the product that the market needs. And so rather than searching for product market fit, you’re actually being told by the customers what product market fit looks like.

KASS LAZEROW: And you have to be ready to listen to that because half the time with pivots – it’s ego that you don’t do the pivot. So you have founders who sit there and go, “Well, wait, I raised money on the first idea. I can’t go back to the board and tell them that this isn’t working. I can’t go back to my family and tell them that this isn’t working.” So you have to listen, and we were having clear feedback to us.

BERMAN: Still ahead, how a focus on company culture helped Buddy Media grow, and why Kass and Mike turned down a massive offer from Google and exited to Salesforce instead.

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Kass & Mike’s philosophy on managing a board

Around the time that Mike and Kass were getting Buddy Media up and running, I was working at MySpace. And shortly after, I left MySpace. I went out to New York, in part to see them, and we sat in their makeshift conference room, and they showed me what they had built so far at Buddy Media. And we started riffing on what it could be, where it could go, what the market needed, what the business opportunities were, and before I knew it, they were offering me a seat on their board.

KASS LAZEROW: I said we gotta get him on the board because at that point we were moving so quickly that I think I needed someone that I could bounce ideas off of.

And that was another lesson that I learned — you need to have a working board, you need to have people who actually help you. Right? So they have to have a purpose. It’s not just like, oh, they gave you money, and they get a seat on the board. It’s like, no, what are you going to do for that money?

BERMAN: Mike, there’s something very powerful about how you communicate with boards and how you manage boards. Can you talk about your philosophy on that, how you did it at Buddy, and how you now advise companies to do it?

MIKE LAZEROW: Yeah. So I think the biggest issue with founders and their relationship with boards is the founders don’t have a clear idea of what is going on, right? They can talk about it, but they really can’t think clearly about their plan. And so I would write these epic letters.

Which would take probably like a day where I’d outline my thinking. Here’s what we said we would do, here’s what we’re doing, here’s where we’re going, here’s why. And that forced me to put it down on paper. If it didn’t make sense to me, it would never make sense to anyone else. And so board decks are very useless.

KASS LAZEROW: Yeah.

MIKE LAZEROW: Other than the financials because it doesn’t really tell a story if you can’t sit there and communicate what you’re doing, why you’re doing, what are the top three areas of focus, why those areas of focus are so important. You will never be able to move the board forward let alone your team.

I’ve always treated the board as partners, not as bosses. I’m no better than them or worse. It’s just we are partners in this, and it’s helped me — as you know we have like a hundred investments in the tech space — work with entrepreneurs better. I really asked them to write it down. Like, if it’s not written down, it doesn’t exist.

KASS LAZEROW: I think Mike’s also not telling the other story. So at Golf.com, when we started, like we had to redo the whole company, that meant new money, right? And a new board. And we had two sharks on our board. Now, we didn’t own much of the company. And that was Jeremy Mindich and Matt Sirovich. And they had a hedge fund.

And I remember the first board meeting that I gave, right? So, a whole new company, and he said, “How is sales going?” I’m like, “Yeah sales is going pretty good. I mean, Mike, why don’t you talk about it?” And Matt Sirovich, I’ll never forget it, screams at the top of his lungs at me, “Don’t shine the turd.”

And I remember just kind of like literally like losing the blood in my face, having goosebumps and going, okay, and that was the lesson. And so Mike took that.

BERMAN: So what did you hear when he said, “don’t shine the turd?”

KASS LAZEROW: Say what the sales are. They’re not good. They’re not great. They’re not okay. Say the number. Say what’s going on. Be truthful. Be transparent. Like have radical transparency. And it doesn’t matter if it’s your board, your employees, you’ve got to be transparent. And I think Mike did, took that lesson because we were like, it was as if we had just been massively reprimanded, and we took that lesson, and he did such a good job going forward, and that was it.

It was just full transparency going forward.

MIKE LAZEROW: I think we realize that people in general are okay with bad news, especially these days, right? But even then they’re fine with bad news. People hate surprises. So if they think things are going this way, but they’re actually going this way, that just ruins trust forever.

How Mike & Kass operate as co-founders

BERMAN: It’s one thing as co-founders to figure out roles. You’re also wife and husband here. How do you two divide roles in leading a company?

KASS LAZEROW: So I do everything that’s operational. So anything that touches legal, accounting, teams, employees, HR, finance. And then I also took on marketing, which is unusual, but it’s like a pastime for me. And Mike is always doing vision, sales, strategy, board. So raising money.

MIKE LAZEROW: I got all the credit, like Ernst and Young Entrepreneur of the Year, all these things, Kass does all the work. And she made me look incredibly great. These companies only work if they’re operated incredibly well. It’s not the ideas. You have to have a big market and differentiated product, all that stuff. But how Kass has run companies our whole life has been the biggest blessing to us business wise.

Lessons for building strong cultures

BERMAN: Kass, among the things that you do incredibly well in operating a company, is the team part. And you talk about putting the cult in culture. How do you do that? How do you do that great? How’d you do that at Buddy Media?

KASS LAZEROW: So I think it stems from my childhood. I don’t want to be over-dramatizing this, but I did not have the team atmosphere in my childhood that I’d wanted. I’m the fourth kid. There were a lot of alliance games. I always felt like I was not getting picked on a team, if that relates to anybody, and ostracized at some points.

And that was just such an awful wound that I thought, okay, if I’m gonna participate, I’m gonna take a role, and I’m gonna try to make the culture better. So the same thing happened at all of the companies I did.

I wanted to create an atmosphere where there were no alliances, where there was none of this bullsh*t clicks. And literally, there were times where I saw mean girl stuff happening, not just with girls. And I literally brought them in and I said, “If I see it again, you’re fired on the spot. Period. Pencil down. We’re not gonna have that. We’re gonna lift everybody up.”

And then you have to think about the tools, right? What’s the glue to connect everybody? Everyone talks about, oh, how it’s so hard right now because everyone’s remote. It is. But you have to think about how do people bond? They bond in bad times, and they bond in good times.

So if you’re transparent, that’s incredible. If you celebrate the small wins together, that’s a pretty obvious one.

So I wanted to start the glue from the very beginning. So I’d do scavenger hunts. I made everyone dress up. I had leadership team who did not want to do it, and I basically said, I’ll fire you.

But, it was the bond of being together. And the same thing on celebrations, so, I figured if you could make it a year — I mean, this is going to sound bad. But make it a year with me, and I had it thought literally put you on a PIP performance improving plan for those who don’t know that you were going to get the best prize, I could give the most expensive one to put on your desk.

And that was a custom bobblehead of you wearing a Buddy Media t-shirt. And they became the symbol that everybody wanted. Every single person who interviewed there would talk to me in the interview about wanting to get a bobblehead. And it was just crazy, because now, all across New York, everyone’s talking about the Buddy Media bobbleheads.

And you’d see them on the desk. And then the second year, I did this huge, it must have been like, I don’t know, three feet tall, plastic sculpture that said, “I’m a somebody.” Because Buddy Media, we became buddies, everyone was into it. And these rituals and symbols — that is not anything different than what you do in a family with traditions, right? And you have celebrations over birthdays. And so I realized that that was the way to do it. And if I could make them feel things, it would, it would allow them to want to come to work. And there was another big part of it, though. You had to laugh every day. You had to laugh. I cannot stand work environments that aren’t That are so serious, and so I presented bobbleheads by scaring the sh*t out of people, so I would jump out of like rooms and doors, it’s probably not a great HR thing now, but—

BERMAN: And hard over Zoom.

KASS LAZEROW: Correct, it’s a bit harder to presume, but I would make it, and so it was fun because you’d see people going, “Oh my god, it’s my anniversary week,” and they’d start like looking over their shoulder, they’d look under their desk, but I made it fun, because how do we take ourselves so seriously, like we’ve got to be in this together.

How adding a salesperson fueled Buddy Media’s acquisition

BERMAN: So, as the leaders of Buddy Media, you navigate these pivots, you navigate these scaling challenges. There’s product market fit. It starts hockey sticking and company gets to a point where there’s, there’s some M&A interest. There are few companies in the category that are swirling, but he’s the market leader.

There’s one critical hire that happens in this phase and there’s a process that leads to selling the company and not deciding to go it alone. Take us, take us there if you would.

KASS LAZEROW: So one of the things that was happening is Mike was getting a lot of interest from California companies, specifically Salesforce was really talking to us about like, what are we doing? They were kind of opening lifting the hood up and asking.

And I thought to myself, what would really make us well-known to companies? And I think I even bounced it off of you. What if I stole the number one salesperson from Salesforce and convinced her to come over to our team? We needed her. We needed to upscale our team. At the time, Jeff Ragovin, Mike, and I, we were doing the best we could, but if we were going to really go for it, and at that point, with 50 million dollars in ARR at that point, we had to go public.

Right? Because we were getting so big.

MIKE LAZEROW: We were on the trajectory,

KASS LAZEROW: We were like, looking, that was our plan. I thought, this would be a good move.

And I was going back and forth to the West Coast to meet Susan and convince her that she should lead this big company.

BERMAN: Not easy. I mean, Salesforce is a fast-growing company. She’s a superstar there.

KASS LAZEROW: And Marc is incredibly generous with all that he gives every

BERMAN: Marc Benioff. Yeah. So, how did you get Susan to come on board?

MIKE LAZEROW: We dated her, it’s felt like, and which just means we’re spending time with her. We’re flying out. I remember the dinner in Woodside at that fancy restaurant, and we had a vision and we needed someone

KASS LAZEROW: And she was gonna be president.

MIKE LAZEROW: We were the fastest at the time, like the fastest-growing company to reach 50 million in like annual recurring revenue. took us three years on the back of Facebook. No end of sight. Nine out of the top ten brands in the world were using us for all of their social marketing to get messages out to all their markets globally. We have offices in Singapore and we’re like, can’t keep up, right? And we just told the story the way we saw it and gave our really, it wasn’t about the money, but at that level, it is, so we have to present with like very generous equity grant and to her credit, she took the job and I kept thinking, I don’t know why she’s doing this right?

Like leaving Salesforce and she’s gone on to do incredible stuff, but I think three months later, after we hired her, I then had to have another scary conversation, which was you’re going back to Salesforce because I just spoke to your old boss, man, and he’s going to buy Buddy Media.

Buddy Media’s acquisition to Salesforce

BERMAN: So at the time, Google was looking to acquire in this space. Microsoft was looking to acquire in this space. Salesforce, there were a couple of other companies circling, and there were a handful of competitors who were smaller, but doing similar kind of work.

You guys had a choice. Right? You could keep going it alone and probably go public and try to stay on the trajectory or sell. And you ran a really interesting process. Tell us about the process you ran and why you ultimately sold to Salesforce?

MIKE LAZEROW: So we ultimately sold because the signs were so clear that it was our time to sell. We had, I’ve never told this story publicly, but we had a term sheet from Google, there was a hundred million dollars more than Salesforce. A hundred million is a lot of money. And it was a lot of money for us at difference. And we had Yahoo and Microsoft circling and, I had been in San Francisco and I went to Marc’s house.

And he just said, let’s go through your software.

And I had all the data, and I used this mapping tool where I just circled an area of the map, and it put all the people on Facebook into a targeting bucket. And Marc is like me in the sense that like we can’t control our like excitement. Like when I get excited it’s like I kind of jump out of my shoes.

And Marc’s like, Oh, like this is so cool. And we basically hashed out the deal. And I knew nothing about the software business, but Marc had written a book that’s like, here’s our playbook. And I’d consumed this book, modeled the whole business off of the book, and I had this like massive man crush, which I still do.

He’s such a great guy, forget entrepreneur. Just he does the right thing.

And we got the deal done and it turned out that if we hadn’t done that deal, I think like I haven’t talked about this publicly either, I think we would have had a hard time as a business and I think it was a tough acquisition for Salesforce because soon after Facebook made it known that they didn’t want anyone between them and their customers.

We were the biggest one between them and their customer. Their advertisers were spending at the time it was early over a billion dollars with Facebook through our platform, right? That’s not a great thing for a large platform, right? To seed their ad business. And so the timing was just great.

KASS LAZEROW: And also, we had done our due diligence. Remember if you remember back with Golf.com, I was not going to let this happen again. So I was doing due diligence that, by the way, anyone who’s done due diligence, congrats. If you get through that process, I was up all night, all day for three months making sure that everything was looked at.

And one of the things I also realized about Marc Benioff is he has this huge charitable part of himself and his companies. Like he believed what we believed. And I thought, this is great. We were struggling to keep up with hiring salespeople. Here’s a company that’s all about salespeople. And the expertise. And there’s also the same shared values and morals. So it was great.

Kass & Mike’s investment strategy

BERMAN: We’ve got a few minutes left. You all have become extraordinary investors, post-acquisition extraordinary investors.

For those who are listening to this, Mike’s wearing his liquid death cap as we sit here and talk. You have invested in over 100 companies, largely tech companies. How do you decide what companies to invest in and how do you allocate the responsibilities of assessing that?

KASS LAZEROW: So I always look at the team members, right? And I’m gonna also do the due diligence, right? So Mike’s gonna look at, obviously, does the business model make sense.

Do they know where they’re focusing? And I look at, do they know what they don’t know? The biggest thing I can tell you as a founder, is you better know what you don’t know, and then you better hire around you. Do they know that they need a leadership team that fills in their gaps? or they do they have hubris?

Are they incredibly arrogant? Are they full of pride? Do they understand they’re going to pivot six times? What time they start with is not going to be what they end with. So I’m looking at that.

MIKE LAZEROW: I’m very gut-oriented, but I have a framework as well. So I just think that an entrepreneur who loves to shovel is unstoppable, and it’s, is this person going to be able to run through walls and get it done? Because whatever they’re doing right now will have to evolve if not completely pivot. then it comes down to something that we actually have we have a framework, which is kind of in the book, Shoveling $h!t, A Love Story, which is very simple:

What’s the product? Why is it different? Who’s the customer? When I say who’s the customer, it’s not only who, but how many of them are there?

How are they going to find out about it? So the sales and marketing, how are you going to deliver it? Like, so it’s the whole operations side. And then do the financials make sense on the napkin? Like do they pass the smell-test?

Those six things with – is this the right founder has gotten us into just great companies, companies like LiquidDeath, companies like Scopely, which we were a seed investor that sold for five billion in cash. Companies like eToro, and originally we were investors in Facebook and Tumblr, and so I just think that entrepreneurs have a miserable life, and there is nothing else that they’d rather do. It’s the beauty and the struggle. And if you see an entrepreneur, you know it, and we really have tuned into kind of who are the people who are on their path, who have found their purpose like we did and that’s what matters.

Advice to young people right now

BERMAN: As we sit here in March of 2025, if a college student comes up to you and says, what should I be looking at? Forget about what I’m passionate about, Mark, what should I be looking at? What’s your answer right now?

KASS LAZEROW: I mean, to me, it’s so simple. It’s basically large platforms that have aggregated audience, AI, and the no-code development platforms.

So check Lovable.

I think that IO, but it’s just a chat. Build me an app or a website that lets me upload a picture of my of an animal and get a picture sent to the house like, and it’s like, it opens it up and it walks you through how to connect it to a database.

Right? And so all of a sudden we have the democratization of engineering with the largest productivity hack the world has ever seen, AI, and access to consumers that we have never had access to like this,right? And I’m not talking about just Facebook and Instagram and whatever that Twitter X thing is, but also Shopify and Etsy all these other incredible platforms.

And so I just think figure out an I=idea that should exist, and even a journalism student can build it now.

BERMAN: Shoveling $h!t, A Love Story comes out in June, Cass and Mike, it’s a fantastic read, I can’t recommend it highly enough, if you’re in business, if you know a young person who’s thinking about being in the world, this is the gift to get them for graduation this year.

Thank you so much for being here, and more to come.

KASS LAZEROW: Thank you.

MIKE LAZEROW: Appreciate it.

BERMAN: To say that I had so much fun talking with Kass & Mike at South by Southwest would be a horrible understatement. Their intellect, their ability to see what’s coming next, their drive, but also their humanity — it makes them extraordinarily special people. I’m so glad we had the chance to talk about their journey and to talk about why they wrote Shoveling $h!t: A Love Story. I devoured it, I think you’re going to love it when it comes out, and we’re grateful for you being here for this conversation.

I’m Jeff Berman, thanks for listening.