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The Billion-Dollar Marriage: What They Know That Most Founders Don’t | Ep. 224 with Kass & Mike Lazerow founder of Golf.com
00:24:55
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- [00:01]
A
Hey, everyone. Welcome back to founder story. Today we have two guests, which, by the way, I always enjoy talking to two people than just only one individual. And not only do we have just two guests, we have two of the most incredible guests I think that we've ever had at the same time. Cass and Mike Lassero, serial entrepreneurs, investors, Co founders of Golf.com I'm a URL buyer. That has to be the best URL I've ever heard. Bloody media. You even sold to Salesforce for over $700 million. And you have a new book out, Shoveling Shit. What an. I mean, we gotta start off like, how did you come up with that name?
- [00:45]
B
Well, you know, when we really thought about what it means to be an entrepreneur and what do you do all day long? You shovel shit. So we thought it was the most intuitive name that we could go with that would really amplify the entrepreneur's journey and express to all of them that are out there that we know we can feel their pain.
- [01:09]
A
I also like how in the title, and maybe Mike, you can speak to this too, the Messy Path to Success. How do you feel in your path? How, like, why was it your path? The messy things that you had to go through, did that inspire that part of the title?
- [01:27]
C
Yeah, well, it's all of it. So it's shoveling shit, because that's what it is. You get to work, shit hits a fan and you just gotta shovel, you gotta keep going. But it's a love story because the best entrepreneurs learn to love to shovel shit, right? It's also our love story. We built our love affairs and our family and our life really on the back of being co founders of these companies. There was no separation between the business and life, which, whether you're married to your co founder, whether you sleep with your co founder, you still have a very close relationship, right? And it oozes into your personal life. So your husband may not be in your business, but trust me, he feels like he is because you come home from work and you're stressed out and you've like been busting your ass. And so it's both a warning that if you want to choose this path, it's going to be hard and very optimistic because it's where you find your passion, it's where you find your purpose, it's where you make the money that's going to power the rest of your life. You're going to meet lifelong friends. And so it's yes, it's shoveling ship, but it's this love story. About this kind of messy path. And the stuff that we love in the world is messy, right? Like a lot of the stuff we like is just not neatly put into a box. We like it because of the hard work. We went through something with other people that bonds the relationship. So we tried to capture that. But it's really the cheat codes and all the learnings inside which matter.
- [03:03]
A
So I've also co founded and worked with my wife and I was told that, you know, at 8pm you have to stop talking about business and you have to do all that separation. Do you think this is a big misconception?
- [03:16]
C
I mean, Cassie, take it away. I mean, I know what I'm going to say.
- [03:20]
B
Do I think it's a misconception that, you know, people shouldn't, who are married shouldn't work together?
- [03:25]
A
Is that what you're asking more about? Like you want to have the separation of like you, you know, you gotta stop talking about business here or there's, There has to be like a something there where you kind of stop the business side and then you go to the personal side.
- [03:42]
B
I think you have to have more than just business to talk about because it won't, I think, I don't think it really nurtures your relationship. But I don't want people to think that. We're not talking about work a lot. We're also talking about our kids a lot. Right. We're also talking about what we're doing for the weekend a lot. But, but is there work talk? Yeah. Do Mike and I, I think we don't have like rules around. Like, okay, at 8pm we're not going to talk. It's more like, I can't talk about work anymore. I'm so tired. Right. So that's my answer. What's yours, Mike?
- [04:16]
C
So I hate rules. That's probably why I became an entrepreneur. And so I'm, you know, we try not to say you can't do this, right? Or it's a rule not to do this. Last night we were up till 11 o' clock working. We have a lot of stuff going on. We have businesses, we got the book and we just need to do it and no one else is going to do it. So we put our heads down. However, we also, as we talk about in the book, have found ways to build our relationship. Date nights every Wednesday and Saturday night. And committing to them, even with three kids, even with a lot of stuff going on, making them sacred. If you can hire a babysitter and have the resources or maybe a parent will Agree to fill in on one of those nights. You know, I don't love rules, but you also have to pay attention to stuff that's important and if you don't prioritize it, it'll be gone. So if you just work on your business and don't prioritize relationships, assume those relationships will not be strong and will eventually die.
- [05:19]
A
There's two commonalities that we've heard. One is we had Ryan Sirhan on recently. He said he is, he would make the worst employee. So I think we're all, we're all in the agreement that we wouldn't be really good employees. The second one is almost choosing between some of the other successful people we've had said I had to choose between, you know, my marriage or my business. So I like the fact that you're marrying the two together. I'm, I'm a strong, I think I'm a strong believer in that, that you can do those at the same time. So how was it in the beginning when you were really building up the first company, were you working together then? And if so, how was that experience from being, you know, the startup without any knowledge at that time?
- [06:04]
B
So I think when you, when you look back, our first company together was golf.com and I started it with another co founder. There were three of us that, that actually did the company. But I came home every night and asked Mike for his opinion on everything. Right. So, so with a, you know, really strong competitive advantage in recruiting because we live together. So do I think most people should run out and start a company with the person they're dating? You know, I think it, you, I think you have to have a pause and really think about skill sets and if you trust the person and you don't overlap in your skill sets. So it was easy for us. We just started, you know, I, as, you know, a certain amount of time I was like, Mike, you just have to join the company. And so he did. And I don't think it was hard. I think it was actually like what Mike and I say. It was very purposefully driven. Like we knew what we were doing together. We, we had this support system between us because we were doing the same thing and we knew the same struggle. And so I think that actually made our relationship stronger because we never brought, we never took things personally in our, in our personal relationship because we were so direct with our business relationship.
- [07:19]
C
And I also think that, you know, the co founder relationship, no matter who you are, is difficult and it's one of the primary reasons Companies go out of business, the primary reason is they run out of capital, run out of money. You're probably not going to be in business. But I can't tell you how many of our 100 investments. You know, the ones that don't work out, it's typically internal. It's not competition, it's not product market fit. They fight. And so we in the book have a whole chapter about saying, I do. Because whether you get married like we did or you just start a company together, it's very hard to unwind that relationship as a co founder. And so there are a few things we like, we like skill sets that don't overlap. So I don't love two engineers or two salespeople. Cast does operations. We do every, you know, I do kind of more sales and that stuff. And we like asking a series of questions that are more value driven, like, how hard do you want to work? What are your goals? You know, what are the expectations on, like, how fast I'm going to respond on email, right? Very simple thing. I was just talking to a co founder who is like, my co founder is driving me crazy. It takes two days to write back. I'm like, well, why are you just emailing? You should be like co founders you should talk to five times a day. But it's, you know, that relationship is not. Is going to make you feel shitty if you don't figure it out from the beginning. And, and I think we did that by accident, but it worked.
- [08:51]
A
So knowing that you have to shovel and knowing that most people probably would not want to be into the position of having to shovel shit as their job 24 7, would you say that most people should not be an entrepreneur, cannot be an entrepreneur, or can they be? What is your feeling? Because I've heard both. You know, some people say anyone can be an entrepreneur. I'm probably of the opposite mindset, just, you know, knowing how tough it is. But what are your thoughts there?
- [09:23]
C
I think everyone is entrepreneur. So I mean, everyone is an entrepreneur. Like you're born and then, you know, think about like your life. You're a free agent and then even when you go to apply for a job, your product is you, right? Like, it's basically like, oh, why should I hire you? Like, and the problem with the industrial education complex is it teaches kids not to be entrepreneurs, right? It teaches them to sit down, shut up, do what other kids are doing, you know, not explore, you know, don't think about the world in like this project way. But in terms of like, what can I put in my brain and then they're thrown into the real world. And then the question's like, why are you different? I don't know. I'm like everyone else. They told me to sit down, shut up. And so, you know, somehow we beat the entrepreneurship out of people. I've never met a kid who just wants to like, do what everyone else wants to do. All of our kids were crazy, all over the place, right? They're just independent things, but then you, at some point they're put in boxes. Now they're different types of entrepreneurship. So this book was written in my mind for a pizza place owner, someone who's running a one pizza place or a series, who's dealing with employees and dealing with like investors who've like put in some money and customers who want their pizza and all. And I think anyone can be an entrepreneur. It's just what level? We're not all going to be kind of Elon Musk, Bill Gates, like whoever you put up on a pedestal. You may be a great accountant who hire some people and have a great accounting firm. You're an entrepreneur.
- [11:09]
B
I agree with Mike. Everyone is their own entrepreneur. It's just about how, how much of who you are, you're going and how much risk you're going to take. Right? So you could be your own entrepreneur within a company and really have you as the product that you're selling and your output is part, you know, the product that you're selling. Or you can take on more risk and actually start something on your own. Right? But I think what you need to become a successful entrepreneur, I don't know if everyone has that. So that's what I would agree with you on, that not everyone has the right skill set, the right risk tolerance, the ability to lead, to understand how to communicate effectively and transparently. And, you know, how you scale a company in that very specific period when you get product market fit, that is, that is a really unique skill set.
- [12:06]
A
So you've sold a company over $700 million. I would probably say if I asked a thousand people that own a business, what is their end goal, at least in the US they would, they would say, I want to exit and I want to exit. You know, exiting for a couple hundred thousand dollars might be, you know, the dream of some, but selling for a few hundred million dollars is, you know, is the ultimate pinnacle goal, I would think, from many, many people. So what was that experience like? Cause I've heard, you know, the goods and bads of, of when you exit. What was the experience, like, for the two of you, maybe even on the emotional side of leaving. Leaving that company and then knowing that you're going to have to do something else.
- [12:51]
B
So I think if. If we start with the fact that we were. We spent four and a half years getting to 50 million in annual recurring revenue so really fast and getting up to 350 people. And, you know, we. We were thinking projections for the following year of about a hundred million in annual recurring revenue. So we were thinking really, really big. And I think the acquisition came at a perfect time. So in terms of, like, were we bummed that we're leaving the brand behind and everything that we built, I think we were really proud. I think that both of us thought, like, this is something that we've really done well, because we are. We believe in giving everyone a slice of the pie. And even some of our vendors got slices of our pie, and everyone was going to leave with something. And that made us feel very, very happy. I think the road to get there really beat Mike and me down. And it was. He was traveling nonstop. I was traveling some, too. We had three kids under the age of, I don't know, 10, under 9 years old. And it was hard. It was really hard. And to keep connected in the personal way when you're also, like, trying to put out fires, like, left and right. So. But I was very happy exiting. I don't know. Mike, were you happy? I mean, obviously there's a huge reward.
- [14:15]
C
I wouldn't say happy. What's interesting is it's a really good question, like, what Daniel asked, because what I remember is sitting in Marc Benioff's townhouse negotiating the deal. But my head was back in New York because our oldest was having some health issues. Miles, I don't know if you remember, Cass, but Cole was getting in trouble at school for goofing around. And we just hired this, like, you know, I was having a hard time scaling just myself. Like, we went from zero to, like, hundreds of employees. We hired this woman named Tammy to, like, help, and she, like, interviewed all my direct reports, and she came back like, oh, you got issues. Like, let me tell you what people are saying. And I was 20 pounds heavier. Cass and I were not very connected because we had offices in Singapore and Europe, and we were never, like. We were working together, but we were never really together. Constant travel and, you know, we were. I wouldn't say broken, but we were kind of numb. And so when we announced the deal, it was just like, um, you know, yes, we were proud, but Also relatively miserable because of the five years of just nonstop, like you don't go from zero to hundreds of employees of 50 million plus in revenue with, from just an idea without like shoveling a lot. And you know, Facebook was going public around that time and it was high profile because once it got announced, it was like the biggest deal in New York City for I think a decade, like the decade before. And no one prepared us for that. And we never got into it for the money, so we weren't like, oh, how's this going to change? And it does. Like, making a ton of money changes stuff. And we're the luckiest people in the world. So it's like all these conflicting emotions. Even when you're successful, I could tell you when you're not, it just wears on your health. It's hard.
- [16:26]
B
I think he covered it and you know, there was a feeling of like, pride. And I remember when we had made this like, like it was basically an acquisition party for everybody. And we announced it and we were gonna all celebrate it together like we usually did. And there's 350 employees. People flew in from around the country and around the world. And Mike comes out on stage and everyone's clapping and we do this whole big thing and it was like this moment, like a snapshot of like we could actually feel it. And then right after we got in the car and I was like, okay, we've got two doctor's appointments for the kids tomorrow. Who's going to be home with Viv? It was just like you just keep, you kind of keep going and you know, the shit never stops, no matter where you're getting it from. So it's absolutely life changing. And like I said before, what, what made me the most proud was our team and everybody having a slice of the pie and making something.
- [17:26]
A
So you, you mentioned Gary Vee earlier and I have to say, getting to spend some time with him, he's probably one of the most humble people that I've met and just grinding 24 7. The guy's like non stop energy. And it just made me think about what you said and I'm, I'm curious your thoughts here. So you, you, you create this hope, high profile exit, incredible success with this company. Like unbelievable success in, in that period of time. I can imagine the, I'm sure we could talk for three hours about the. That happens when you, when you scale that, that fast, that soon you sell the company like you said. Now you have to go back to, back to real life or back to the Other life, you know, personal life. And, and, yeah, but it seems like, like entrepreneurs go through this thing, okay, I sell my company, I create this high profile status of myself, I gain notoriety and some fame. But, you know, what is this all leading to?
- [18:25]
B
Well, for us, it was leading to. I mean, obviously personally, you know, money doesn't make you more happy, it just makes you more comfortable or it's convenience. But for us, it meant that we could do more giving. Right? Like, we could really focus on the impact we could make. And I think that became a big priority. We've been working with Cycle for survival for 18 years, and that has become our number one cause. So I think that's, that's what it all means for us. Right, Mike, what would you say?
- [18:56]
C
Yeah, what's interesting is, you know, Gary. Gary started from one of our conference rooms. So when he showed up, he was like many of your listeners. He'd worked for a family business, never made more than a hundred thousand a year, had no money in the bank. Dad wouldn't give him equity. We know his dad, we know why. Like, you know, he's first generation, you know, great business guy, but it's, you know, different. And he said, I need your conference room. I don't have money for an office. And I'm like, I'm fine with it. You know, I didn't really know Gary. I'm like, you seem pretty, like, wild, like you're a weird creature, but I kind of like, you know, but you got to talk to this lady. So I'm like, you know, he went and talked to Cass and Cass said yes, which was. Amazed me. And like, the mentality that we share, that all entrepreneurs share is this love of hard work. This. The best entrepreneurs, I think, want to give more than they receive. So in selling, their giving, in hiring, they're giving, you know, Cass, when she lets someone go, they feel great because they know their strengths, their weaknesses. Like, it's like the first real conversation a lot of people have had in their life. And so I think inside this struggle, the suffering that we all love is just a lot of purpose. Because I've thought a lot about, like, okay, it's hard, it's miserable many times, like trying to sell books like we're doing right now. However, there's nothing else I want to do. Like, there's nothing else I would do. So it's that kind of being able to hold the idea that it's going to be hard and you're going to have to sacrifice and you're not going to be able to do everything you want to do because you're responsible for other people and investor money and customers and it's awesome. Don't do anything else. Now the problem with most entrepreneurs is they're entrepreneurs before they know they're entrepreneurs. And they, their first PNL is their personal P and L and they have a job and then they decide to buy a huge house and they buy three cars and they're on their second marriage. They have child care and then they're like, I'd like to start a business. Well, dude, you're like, you know, your L, your losses, like your expenses are so big that like you're not going to be able to recreate that out of the gate. Right. When you're working for yourself, there's a lot of sacrifice. We didn't take salary for many years. And so there are two ways to get rich, which I forget which book. I was just reading a book which like perfect, like you know, comment on being rich. It's like want nothing or make a ton of money. And I think you need to want nothing as an entrepreneur. Like, Gary wanted nothing. He wanted a conference room to start his business. He didn't want cars. He didn't want anything other than like what he needed for the business. So if you've got a huge mortgage and you have like all these responsibilities, be an adult and figure out how to pay for it. Being an entrepreneur may not be the best route for you.
- [22:05]
A
Wow, that was deep. I like that either. Maybe Want Nothing is better in life. Maybe that is the, the best way to be rich is to want nothing.
- [22:14]
C
It's actually, it's this book right here which for those who can't see, Rules for a Night by Ethan Hawke, one of my favorite all time books, which was just sitting here. And it's basically these tiny bits of wisdom about life. And people don't go bankrupt because they're not making money. They go bankrupt because they like took on debt. Right. Entrepreneurs know the power of debt and the destructive force of debt. Right. We understand how to balance a checkbook. Like learn that before you do anything else. And I'm a journalism major, so entrepreneurship.
- [22:52]
A
Is like the balance of, I don't want to say good and evil, but it's like the, like you said, the debt could be the greatest thing to your business, but it could also be the bankrupting thing to your business. And taking on an investor. Could be. I was just reading about some people that I know that were, you know, kicked out of their company from the investors so it's like, could be the worst thing and it also could be the greatest thing. But you might have to do it knowing that it could turn into the worst thing. Because right now it's the greatest thing.
- [23:22]
B
Right? Because. And you have that risk tolerance, right? Like despite the fear, undeterred by the fear, you're going to move forward, right. And make decisions and live in a storm that's constantly changing.
- [23:35]
A
So successful entrepreneurs really are crazy.
- [23:37]
B
They, they really do have to have high risk tolerance.
- [23:40]
A
I can tell you that I'm equating crazy with risk tolerance. But yeah, that's fine then. That sounds better. That sounds much better. But this has been amazing. I could talk for three more hours. I, I mean, you have to come back on because I have 40 foot moments of another conversation that we have to have about some things I didn't even get to ask yet. But if people wanted to check you guys out, they want to get the book. How can they do so?
- [24:02]
B
Just go to shoveling.com very easy. You can see the book. We also are giving away like lots of free bonuses. If you buy one book, you can upgrade and get a ton of other bonuses. But just go there. It's all right there for you.
- [24:15]
A
You have the best URLs.
- [24:18]
B
Thank you.
- [24:19]
A
Com is the most epic URL.
- [24:20]
B
Like that was amazing.
- [24:22]
A
Yeah, a four letter URL. I'm like a. I buy crap.
- [24:25]
B
I get it.
- [24:26]
C
At a time when URLs mattered. Now it's like apps and sidetrack traffic.
- [24:30]
A
It's amazing though, like shoveling.com that's, that's incredible. But quas. And Mike, I'm really honored and appreciative that you are here and I hope everyone checks out the book because I know it's going to change a lot of lives and you're going to impact millions of pe, if not billions of people. So thank you for joining us today on Founder Story.
- [24:49]
C
Thank you, thank you, appreciate it.