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
Mon, 2 Jun 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.
Chapter 1: What does 'shoveling shit' mean in entrepreneurship?
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? 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 shit because that's what it is. You get to work, shit hits the 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.
Chapter 2: How does business intertwine with marriage?
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. Right. 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 shit, 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. Yet 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 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 the separation of like, you, you know, you got to stop talking about business here or there. 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 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.
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Chapter 3: What are the keys to successful co-founder chemistry?
Do Mike and I, I think we don't have like rules around like, okay, at 8 p.m. 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, 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 have 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
There's two commonalities that we've heard. One is we had Ryan Serhan on recently. He said he would make the worst employee. So I think we're all in 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 my marriage or my business.
So I like the fact that you're marrying the two together. 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 the startup without any knowledge at that time?
So I think 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 really strong competitive advantage in recruiting because we lived together.
So, do I think most people should run out and start a company with the person they're dating? 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. 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. Right.
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Chapter 4: What was the experience of selling a $700 million company like?
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 six. 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 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, um, 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 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 than,
I cast and I were not very connected because we had offices in Singapore and Europe and we were never like we're 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, um,
relatively miserable because of the five years of just nonstop. Like you don't go from zero to hundreds of employees at 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, 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.
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 all celebrate it together like we usually did. And there's 350 employees. People flew in from around the country and around the world.
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Chapter 5: Can anyone be an entrepreneur?
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.
So you, you mentioned Gary V 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 nonstop energy. And it just made me think about what you said. And I'm curious your thoughts here. So you create this high profile exit.
um incredible success of this company like unbelievable success in in that period of time um i can imagine the shit i'm sure we could talk for three hours about the shit that happens when you when you scale that that fast um that soon uh 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 uh
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, right? 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, 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, right? 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 like wild, like you're a weird creature, but I kind of like you. 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 the mentality that we share, that all entrepreneurs share, is this love of hard work. The best entrepreneurs, I think, want to give more than they receive. So in selling, they're giving. In hiring, they're giving.
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Chapter 6: What makes a successful entrepreneur?
Well, dude, you're like, you know, your L, your losses, like your expenses are so big that like, you're not gonna 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 fear, which I was just reading a book where it's like perfect, like, um, 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, um, If you've got a huge mortgage and you have 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. Maybe want nothing is better in life. Maybe that is the best way to be rich is to want nothing.
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 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 do it knowing that it could turn into the worst thing because right now it's the greatest thing.
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.
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Chapter 7: How do you balance work and personal relationships?
Just go to shovelingshit.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.
You have the best URLs.
Thank you.
Vault.com is the most epic URL.
That was amazing. Yeah.
A four letter URL. I'm like, I buy crappy URLs.
I get it. At a time when URLs mattered. Now it's like apps and sidetrack traffic.
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Chapter 8: What are the common misconceptions about entrepreneurship?
It's amazing though. Like shovelingshit.com. That's, that's incredible. But, Kwas 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, if not billions of people. So thank you for joining us today on Founders Story.
Thank you.
I appreciate it.