Founder's Story - From Zero to $700M: The Brutal Truth Behind Startup Life as a Couple | Ep. 224 with Kass & Mike Lazerow founder of Golf.com

Episode Date: June 2, 2025

Kass and Mike Lazerow peel back the curtain on life—and love—as co-founders of multiple breakout ventures. From the early days of building Golf.com to scaling Buddy Media into a $700 million+ Salesforce acquisition, they share the grit, the joy and the “shoveling shit” mentality behind every pivot and payoff. Key Discussion Points: Why “Shoveling Shit”?: The visceral truth of entrepreneurship—every success is paid for in messy, daily hard work. Business + Marriage = Love Story: How dating, co-founding and parenting three kids forged their partnership both in and out of the boardroom. Co-founder Chemistry: Choosing non-overlapping skill sets, setting clear expectations, and having tough conversations early to survive the rough patches. The High-Profile Exit: Celebrating a $700 million sale to Salesforce—and the mixed emotions, burnout and newfound freedom that followed. Who’s an Entrepreneur?: Everyone—from the corner pizza shop owner to the solo‐founder—can embrace the entrepreneurial spirit if they’re willing to shovel shit. Risk, Debt & Scale: Why wanting nothing (minimal burn) + smart leverage of debt + relentless focus on execution define the winners. Takeaways: Real success demands loving the daily grind—embrace the mess, don’t fear it. A co-founder relationship is your most critical asset—invest in alignment on values, work ethic and communication. Money changes the game but doesn’t guarantee happiness; use your windfall to fuel purpose and impact. Everyone can be a founder at their own scale—but only those who master risk tolerance and ruthless prioritization will thrive. Closing Thoughts: Kass and Mike Lazerow prove that the world’s greatest companies—and relationships—are built one shovel of shit at a time. Tune in to find out how they turned daily disasters into billion-dollar exits, and why the love of the hustle is the ultimate driver of both profit and purpose. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hey everyone. Welcome back to Founder's 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 Lassro, serial entrepreneurs, investors, co-founders ofGolf.com. I'm a URL buyer. That has to be the best URL I've ever heard. Buddy Media, you even sold to Salesforce for over $700 million, and you have a new book out shoveling shit. What a name. I mean, we got to start off like, how did you come up with that name? 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, really, amplify the entrepreneur's journey and express to all of them that are out there that we know we can feel their pain. 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? Yeah, well, it's all of it. So it's shoveling shuffling, shit, because that's what it is. You get to work, shit hits a fan, and you just got to shovel. You got to 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 affair 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 it 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 And, but it's really the cheat codes and all the learnings inside which matter. So I've also co-founded and worked with my wife. And I was told that, you know, at 8 p.m., you have to stop talking about business and you have to do all that separation. Do you think this is a big misconception?

I mean, Cassie, take it away. I mean, I know what I'm going to say. Do I think it's a misconception that, you know, people shouldn't, who are married, shouldn't work together? Is that what you're asking? More about, like, I want to have this. separation of like you you know you got to stop talking about business here or there you there has to be like a something there where you kind of stop the business side and then you go to the personal side 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 is there work talk? Yeah. Do Mike and I, I think we don't have like rules around like, okay, at APM, 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? 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 11 o'clock working.

We have a lot of stuff going on. We've businesses. We've 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. There's two commonalities that we've heard. One is we had Ryan Serhan on recently. He said he is he would make the worst employee so i think we're all on the agreement that we wouldn't be really good employees the second one is almost choosing between some of the other successful people

have 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 uh i think i'm a strong believer in that that you can do those at the same time so how was it uh in the beginning when you were really 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? 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 actually did the company. But I came home every night and asked Mike for his opinion on everything, right? So with a, you know, really strong competitive

of 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, 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 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 personal relationship because we were so direct with our business relationship. 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 hundred 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, adult, overlap. So I don't love two engineers or two salespeople. Cast as 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? A 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 I think we did that by accident, but it worked. So knowing that you have to shovel shit 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 knowing how tough it is. But what are your thoughts there? I think everyone is an 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 of 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 and 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 freaking crazy all over the place, right? They're just independent things. But then, you know, 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 at 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. I agree with Mike. Everyone is their own entrepreneur. It's just about how much of who you want.

are you're going and 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 of you know the product that you're selling or you can take on more risk and actually start something on your own right but um 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.

So you've sold a company over $700 million. I would probably say if I asked, ask a thousand people that own a business, what is their end goal? At least in the U.S., 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? Because I've heard, you know, the goods and bads 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.

So I think 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 were thinking projections for the following year of about 100 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, where 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 nine 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. I was very happy exiting. I don't know, Mike, were you happy? I mean, obviously, there's a huge reward. I wouldn't say happy. Like, what's interesting is, like, it's a really good question, like, what Daniel asked.

Because what I remember is, like, sitting in Mark Benioff's townhouse negotiating the deal. But, like, my head was, like, 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 yeah 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 i cast 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 um 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 um and no one prepared us for that and we never got into it for the money so we weren't like, oh, how is 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. I think he covered it. And, you know, there was a feeling of like pride. And I remember when we had made.

this, like, it was basically an acquisition party for everybody. And we announced it and we were 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, you know, where you're getting it from. So it's absolutely life changing. And like I said before, what made me

the most proud was our team and everybody having a slice of the pie and making something. So 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 guys like non-stop energy. And it just made me think about what you said. I'm curious your thoughts here. So you create this high-profile exit, incredible success with this company, like unbelievable success in that period of time. I can imagine the shit. I'm sure we could talk for three hours about the shit that happens when you scale that fast that soon. You sell the company, like you said, now you have to go back to real life or back to the other life, you know, personal life.

Yeah. But it seems 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? 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 what it all means for us, right? Mike, what would you say? Yeah, and what's interesting is, you know, 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 100,000 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 wild like you're a weird creature but i kind of like you but you got to talk to this lady so like you know he went and talked to cast and cass said yes which was amazed me and like the mentality that we shared 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 their giving you know, cast when she lets someone go, they feel great because they know their strengths, their weaknesses. 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, you know, 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, you know, customers. And it's awesome. Like, don't do anything else. Now, the problem with most like entrepreneurs is their entrepreneurs before they know they're entrepreneurs and they their first P&L is their personal P&L and they have a job and then they decided to buy a huge

house and they buy three cars. 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 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, you know, which I feel which, 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. Wow, that was deep. I like that. Either maybe want nothing is better in life. Maybe that is the best way to be rich is to want nothing. It's actually, it's this book right here, which for those who can't see Rules for a Night by Ethan

Hawk, 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 is like the balance of, I don't want to say good and evil,

but it's 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 kicked out of their company from the investors. So it could be the worst thing. And it also could be the greatest thing.

But you might have to, to do it knowing that it could turn it to the worst thing because right now it's the greatest thing. Right. 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. So successful entrepreneurs really are crazy. They really do have to have high risk tolerance. I can tell you that. I'm equating crazy with risk tolerance. But yeah, that's fine. That sounds better. That sounds much more. But this has been amazing. I get talked for three more hours.

I mean, you have to come back on because I have 40 fun 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? Just go to shoveling shit.com. Very easy. You can see the book. We also are giving away 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. You have the best URLs. Thank you. Alp.com is the most epic URL. That was amazing. Yeah. A four-letter URL. I'm like a, I buy crappy URLs.

I get it. At a time when URLs mattered. Now it's like apps and sidetrack traffic. It's amazing though. Like shoveling shit.com, that's incredible. But Quas and Mike, I'm really honored and appreciated that you are here. And I hope everyone checks out the book because I know it's going to change a lot of lies. And you're going to impact millions, if not billions of people.

So thank you for. yesterday on Founder's Story. Thank you. Thank you. Appreciate it.