Live from SXSW: Mike and Kass Lazerow’s ‘messy’ path to success
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I got the chance to talk to my very old and very dear friends, Cass and Mike Lazaro, on stage at South by Southwest earlier this month. And we wanted to share that conversation with you. Cass and 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 a billion dollars. And now Cass is on the board of, wait, what? The company that makes this podcast. So we're keeping this all very much in the family this week.

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

You've got to have incredible talent at every position. It's like this huge push. There are fires burning when you're going out. Can you believe it? Such an idiot. And then you go back to, this is totally going to be amazing. There are so many easy ways. I have no idea what to do. Sorry, we made a mistake. But you have to time it right. Oops. Working out of a three-bedroom apartment. Stuff that just seems absolutely nut balls. Ten years later, we're like, well, that's just how you do it. We haven't made it just how you do it.

This is Masters of Scale. The Lazaros have distilled their most valuable lessons into a new book, which is coming out this spring. It's called Shoveling S***. Yes, Shoveling S***, 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 Cass about the messiest parts of their careers. Their toughest business moment was back just before the dot-com bubble burst. Mike and Cass were newlyweds, and they were co-founders of the site and the business, golf.com.

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 December 23, 1999, and we were psyched. This company was going public in the spring.

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 like billions of dollars. And on 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. So the deal hadn't formally closed yet. You'd signed an agreement to sell the company to ChipShot. It was close. They're going to go in public.

It was closed. It was fully closed. 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. Right.

And I said, what the, you know, what the f*** are we doing here? We can, it's Texas. Okay, we can do it. We can curse. Okay. So I said, what the f*** 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.

Nothing. Zero. And this was not a deal where you had taken a whole bunch of cash off the table. This was a stock deal. This was an all-stock deal. We were psyched. We thought we had hit it. And your team members were going to do well as well. Yes. Big time. Right? And we own more than 50% of the company. So set the stage for us. You're now in March. This call comes in. Where are you when the call comes in? So we actually lived above our office. Okay.

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. It was the poop deck. Yes. It was basically a poop deck. There's going to be a scatological theme to all of this. Yeah. Yeah.

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're 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? And the answer is no. No. Immediately. Yeah. So you're in the bedroom. You're taking this call. It is a deluge of bad news. The shit is hitting the fan. You must have been personally devastated. Yeah.

Yes. I think the first thing that came to my mind was all the employees, right? I didn't even go to 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 going to happen? So what happens next? Well, 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 a 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. Mike, where did that come from? I mean, I think most people would be spinning. 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 s*** hits the fan. This particular day, it rained s***, 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. E-toys is doing like 100 million of sales, but it's worth like $50 billion. And, you know, everything's going up and to the right. And we sold to a Sequoia-backed company. And we were in our heads very rich.

Yeah, we owned half of this company. And on paper. On paper. Yes. And so all of a sudden it's like, oh, we have like 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, San Francisco, the Bay Area, which was very expensive hotels. So we stayed at a motel that had, you know, the thick glass, like bulletproof. But there were three of us in one room. And we shared a room with our co-founder, which is like a little awkward. Yeah.

Because we had just gotten married. We got married 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.

I mean, objectively, you hit the lottery. Yeah, and I'm like, cross eyes, like bad heart. I'm like, okay. I was like, are you alive and like me? That's all I needed. And we raised the money. You know, you do what you have to do as an entrepreneur. And we found the money. And the key thing about that, and Cass, who's the operator, such a brilliant operator, she was so transparent with the employees and the team that

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, I think, $1.2 million or $1.5 million. In one lunch. Wow. 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, said,

Just weren't pleased with us. I think that's a bit of an understatement. Yeah. Yeah. What was the worst part of that? 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 startup 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, like, this is not going to happen. This is not, 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. I'm like, why me? It was a little odd that he didn't threaten to kill me. I'm not your direct family. It was a little bit odd. But at the time, I think I was just deeply embarrassed by that. Like thinking to myself, like, how does this happen? It was a good lesson in...

Pick your investors wisely. Yeah. Okay? Yeah. And make sure that they can afford to lose whatever they're putting in. So you raised this $1.2 million over lunch with a bunch of golf dudes at a legendary country club. And what happens from there? We went back. I think the first thing that 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, right? No companies are living. The 1.0 bubble has popped. No one cared about us. There wasn't a lot of business. We had to like limp along. We were busy.

mostly dead, right? Barely alive for seven years until the ad revenue business started coming back. And 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 chip shot

crazy. You did have a successful exit. You know, at that point, you're married. You've got two kids with one on the way, right? When we start the next company. Yes, right. And you would be understood for saying, well, I'm going to take some time off. I'm going to figure it out. But you didn't. You started yet another company. Why? Yeah.

Well, it usually happens around the birth of every kid. And he loves to think, like you said, in rabbit holes. And so May 24, 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.

So let's just be clear. Yes. You've just given birth to your third child. It's not three weeks later. No, no. You're sitting on the couch. You're in the recovery room. Yes, and I was in a lot of pain. And he goes, I've got it. And I literally think he is getting me sushi. Like this is going to be, 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. I know what we're going to do next.

I said, are you f***ing 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. So what happened in that moment? Where did that come from and what was the thing? 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 this stuff. So it was like kind of a good thing for the world, we thought. It was a simpler time. It was a simpler time. And I just thought that like everything's better with friends. But when Facebook recreated the social graph, 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 it was going to be a software company. It had to pivot a few times. We would have never called it Buddy Media if we thought it would be a software company. 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? This is pretty ugly, though. 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 like 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 that we said, okay, we're going to pivot into software to help the largest brands in the world. Which 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. And you have to be ready to listen to that.

Because half the time with pivots, it's ego, right? 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 me that this isn't working. So you have to listen. And we were having clear feedback to us.

Still ahead, how a focus on company culture helped Buddy Media grow and why Cass and Mike turned down a massive offer from Google and exited to Salesforce instead. Meet Romeo Regali, a Capital One business customer and chef and CEO of Roz, a plant-based restaurant with two locations in New York.

We started talking about our own restaurant. I don't know if she thought I was serious, but she said, you know, let's just do it. Let's just start our own brand from scratch. Romeo's recalling the moment when he and his wife and co-founder Milka Regali decided to take a leap of faith. I started working as a server at Milka's mom's restaurant. I fell in love so much with the industry, and that's what sparked it.

Romeo and Milka weren't certain how they would bring their dream to fruition. But they were certain of one thing, their passion. We knew we had a vision and we found a space. We had to gut the entire space and build everything from scratch. The kitchen, gas piping, and the restroom, the sound system, everything. We really believed every detail matters.

As they broke ground on their first ROS location, Romeo and Milka soon faced the financial reality of building something from scratch. They looked to Capital One Business to help navigate the fiscal burden of making their dreams come true. We used a Spark Cash Plus card from Capital One. The no preset spending limit really had a big role in helping us finish the project. We're very happy with what we have accomplished. We want to expand more.

To learn more, go to CapitalOne.com slash business cards. The thing about a great pitch is it doesn't just share facts. It tells a great story, the kind of story that moves investors, customers, and teams to action. If you want to get great at storytelling, join us on March 20th for Masters of Storytelling, a live virtual workshop in partnership with Virtuoso.

Learn practical storytelling techniques to refine your pitch, articulate your mission, and build a business story that resonates. Seats are limited, so please reserve yours today at mastersofscale.com slash events. That's mastersofscale.com slash events. Welcome back to Masters of Scale. You can find this conversation and much more on our YouTube channel.

Around the time that Cass and Mike 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.

I said, we got to 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 that 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 at the board. It's like, no, what are you going to do for that money? Right.

Mike, there's something very powerful about how you communicate with boards and how you manage boards. And can you talk about your philosophy on that, how you did it at Buddy and how you now advise companies to do it? Yeah, so I think the biggest issue with founders and their relationship with boards is that

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 in paper. If it didn't make sense to me, it would never make sense to anyone else. And so board decks are very useless 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 has helped, and it's helped me as, you know, now that we have like 100 investments in the tech space, I think it's helped me work with entrepreneurs better because I really asked them to write it down. Like, if it's not written down, it doesn't exist. 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. Right.

And that was Jeremy Minage and Matt Sarovich. And they had a hedge fund. And I remember the first board meeting that I gave, right? So a whole new company, right?

And he said, how is sales going? I'm like, yeah, you know, sales is going pretty good. I mean, Mike, why don't you talk about it? And Mike says, yeah, you know, it's going like this. And he interrupts and Matsurovich, 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 losing the blood in my face, having goosebumps and going, okay. And that was the lesson. And so Mike took that. So what did you hear when he said, don't shine the turd?

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 took that lesson because we were like, it was as if we had just been massively reprimanded. Mm-hmm.

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. I think we realized 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 like ruins trust forever. 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? 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. It's raising money. I got all the credit, like Ernst & Young Entrepreneur of the Year, all these things. Cass does all the work. And she made me look incredibly great, right?

And these companies only work if they're operated incredibly well. It's not the ideas. You have to have like a big market, like differentiated product, all that stuff. But how Cass has run companies our whole life has been the biggest blessing to us business-wise. Cass, among the things that you do incredibly well in operating a company is the team part. And you talk about putting the cult and culture. Um, uh,

How do you do that? How do you do that great? How'd you do that at Buddy Media? So I think it stems from my childhood. I don't want to be like 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 going to participate, I'm going to take a role and I'm going to 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 clicks. And literally, there were times where I saw like 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 going to have that. We're going to lift everybody up.

And then you have to think about the tools, right? What's the glue to connect everybody? Everyone talks about, oh, 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 had scavenger hunts. I made everyone dress up. I had a leadership team who did not want to do it. And I basically said, I'll fire you. But again, it was the bond of being together. And the same thing on celebration. So I figured if you could make it a year...

I mean, this is going to sound bad, but making a year with me, and I had it thought, literally put you on a PIP, performance improvement 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've 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, right? With traditions, right?

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 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 are so serious. And so I presented bobbleheads by scaring the shit out

out of people. So I would jump out of like rooms and doors. It's probably not a great HR thing now, but, but. And hard over Zoom. Correct. It's harder over Zoom, 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, 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. 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. Company gets to a point where there's some M&A interest. There are a few companies in the category that are swirling. Buddy is the market leader there.

there's one critical hire that happens in this phase and then 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. 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, you know, lifting the hood up and asking. And I thought to myself, well,

What would really make us well-known to companies? And I think I even bounce 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 Raghavan, 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 in ARR at that point, we had to go public.

right? Because we were getting so big. We were on the trajectory. We were like looking to like, 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. Not easy. I mean, Salesforce is a fast-growing company. She's a superstar there. And Mark is incredibly generous with all that he gives every employee. Mark Benioff. Yes. So how did you get Susan to come aboard?

Well, we dated her, it felt like, 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. And she was going to be president. We were the fastest at the time, like the fastest growing company to reach 50 million in like annual recurring revenue. It took us three years on the back of Facebook. No end of sight. Nine of the top 10 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 this we're like, can't keep up. Right.

And we just told the story the way we saw it and gave her really, it wasn't about the money, but at that level, it is. So we had to present with a 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. So at the time, the...

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. 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 that was $100 million more than Salesforce. $100 million is a lot of money. It's a lot of money. And it was a lot of money for us, that difference. And we had Yahoo and Microsoft circling and

And I had been in San Francisco and I went to Mark'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 like circled an area of the map and it put all the people on Facebook into a targeting bucket. And Mark is like me in the sense that like you can't we can't control our like excitement.

Like when I get excited, you know, it's like I kind of jump out of my shoes and Mark's like, oh, like this is so cool. And we basically hashed out the deal. And I had I knew nothing about the software business, but Mark had written a book that's like, here's our playbook. And I 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 customer. We were the biggest one between them and their customer. Yeah, customer being the advertisers. 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. 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. 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 Mark 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. So we've got a few minutes left. You all have become extraordinary investors. For those who are listening to this, Mike's wearing his liquid death cap as we sit here and talk.

You mentioned you've invested in over 100 companies, largely tech companies. How do you decide what companies to invest in and how do you two allocate the responsibilities of assessing that?

So I always look at the team members, right? And I'm going to also do the due diligence, right? So Mike's going to 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?

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

Yeah, and so I'm very gut-oriented, but I have a framework as well. So I just think that, you know, 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. And then it comes down to something that we actually have, you know, we have a framework, which is kind of in the book, Shoveling S***, The Love Story, which is

is called the Go Gauge, which is very simple. It's 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 a 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 Liquid Death, companies like Scopely, which we were a seed investor that sold for $5 billion in cash. Companies like eToro. And originally, we were investors in Facebook and Tumblr and all of these. And so I just think that entrepreneurs have a miserable life

and there's nothing else that they'd rather do. It's the beauty in 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. Mike, 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, market-wise, what should I be looking at? What's your answer right now? I mean, it's so, to me, it's so simple. It's basically large platforms that have aggregated audience, AI, and the no-code development platforms.

So check out lovable, I think, that IO. But it's just a chat. Build me an app or a website that lets you upload a picture 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 and, you know, all these other incredible platforms. And so I just think figure out an idea that should exist and even a journalism student can build it now.

Shoveling Sh**, A Love Story comes out in June. Cass and Mike, I mean, 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. Thank you. Thank you. Appreciate it. To say that I had so much fun talking with Cass and Mike at South By 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 grateful we had the chance to talk about their journey and to talk about why they wrote Shoveling S***, 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.

Thank you for listening. The Lobatical is for any employees who have been with us for five years to take a vacation. They get a week of extra PTO. They get to pick anywhere in the world that they want to travel, and we allow that to happen for them. That's Brooke Wright, Capital One business customer and chief people officer at Local, a change marketing company that works with huge corporations in order to facilitate meaningful communication between C-suites and their frontline.

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