Kass & Mike Lazerow — Shoveling Shit: A Love Story About The Entrepreneur’s Messy Path to Success, Building Golf.com & Selling Buddy Media to Salesforce

Welcome back to the Casey Adams Show. Today we are joined by Mike and Cass Lazzaro. Thank you so much both for being here today.

Thanks for having us.

Thank you. Appreciate it.

Of course. So first off, I know we were chatting before, but I am so inspired by your story. You know, as, as. As co founders, as husband and wife, and as now co authors on your new book, which we'll get into. Um, it really couldn't have come at a better time in my life. I know we were chatting before I got married a month ago, and I really am so excited to dive into this conversation today. And you know, for people that may not know, and you guys are both Co founders of Golf.com and Buddy Media with both had acquisitions which we'll dive more into. But again, thank you so much for being here and so excited to dive in today and to kick things off, I got to say, one takeaway from the book you mentioned. Always respond to emails. And I got to start with you, Mike. Your proposal in the book, which I'm sure people will dive into, this whole thing started from an email. Tell us more about that.

Yeah, so Cass and I really met at a wedding right after I graduated Northwestern University. And Cas almost didn't go to the wedding. She RSVP'd to go, but it was over a holiday weekend and one of her friends luckily said, you're cass Savaris. You RSVP'd. You have to go. You can't ditch it. And so we went to the wedding and we hit it off at the wedding. We gave a speech together because we're both from dc, friends with the bride. And, you know, right after the first dance, we had our first dance ever. And there was just kind of chemistry and electricity. Unfortunately. After the wedding, I went back to Chicago and Cass went to D.C. and so what that meant is that we had a year of a long distance relationship and email was really where it started. And yeah, we'd talk on the phone, but I went to journalism school. I'm a writer. And so we'd go back and forth and I have these emails on my desk right here. And they were really cherished emails. And so we were working together@golf.com we did what everyone probably shouldn't do, which is start a company with someone you're dating. And we weren't married yet. And I thought it was time to get married. So instead of asking her and getting on a knee, I sent her an email. And let me just say, the response was not quick. I started to start to sweat after 10 minutes, 20 minutes, half an hour go by and I'll let Cass kind of tell from her side.

Yeah, please. I will say right before you respond, Kaz, when I was reading, like when I was at this point of the book, I literally laughed out loud because I'm just like, oh my gosh, like the way you guys show up online and the dynamic you have and I learn about this. I'm like, this is incredible.

Well, you know, we were launching the very next day, so this was a Sunday, I believe. And we were launching either that Monday or Tuesday. And I was going through all the emails, you know, I had a ton from legal, accounting, you know, web services, you name it. And I go in the order in which they're received. So I start at the bottom. And he obviously had sent it and then he took our dog. We were living above our office so that we could have, you know, we didn't qualify for office space so we just rented it personally, both floors and we were living there. So he's like, I'm going to go up and watch March Madness. And I'm like, okay, well I've got emails to do. He's like, okay, I'll see you in a bit. I think that was like 40 minutes later. And I, and I couldn't. We had another co founder and his wife who were working and they kept looking back at me and just smiling and going. And I was like, this is weird, like something's wrong with them. And then finally I got it and was like, oh no, and then ran up the stairs. So.

Oh my gosh, I'm so glad that to hear that from your both point of view and perspective is so lovely. And of course the book wouldn't be here today if you didn't say yes. So it's very exciting to hear that story and to take a step back before we continue to dive into everything. I know I mentioned it before, but I got married a month ago and I was telling you both before we started this episode that the book, but more importantly your story specifically couldn't have came at a better point in my life. I got married a month ago. I've been together with my now wife for five years and when we first started dating I was starting my previous company which is a tech company called mediakits.com and my co founder and I, his name is Kieran and our first hire and really founding number became Jacqueline, my girlfriend at the time. And I remember the selling that not only needed to be done, but even for myself, like, oh, working with your partner, people say, do it, people say, don't. And it just created such a level of like, intimacy and trust that I believe wouldn't be able to get to where we are today without that. And hearing the early days of not only how you both met, but company dynamics, it really is so inspiring. And I want to ask both of you, in the early days when you both started working together and what became Golf.com was there any doubt? What were some of the conversations that maybe people can get a preview of if they haven't read the book? Because I think it's such a vulnerable state to be in where one thing committed to a business partner is you're locked in. And then being married is one thing, but when you're working with a partner, when you're not married, it does create this level, in my opinion and perspective of trust, unlike anything I've ever experienced before.

I agree. I think you nailed exactly what we tell everybody about working together. So we figured out all of our kinks, you know, by working together and being apart. We had really good communication that year we were apart. You have to, otherwise it just fizzles. And if you're in a long distance relationship and the trust is so huge, I think we actually were surprised when people would say, like, what are you doing? Or like when family would be like, you can't do this. Definitely investors didn't like it. And I think it just kind of fired us up because it's been the foundation for our personal relationship and it's kept us going strong because we do trust each other implicitly. We know we will get things done. We know we have strengths and we play to those strengths. So I think it's been great. What do you think, Mike?

I mean, I think one of the reasons why we wanted to write the book was because of this topic that there's so many just incredible business books, you know, zero to one. And you know the hard things about hard things, I could go on like lean startup. And they really focus on how to build a business. And I think when we look back over 30 years, right. People look online and they think we're like overnight success, but it's been like 30 years of hustling. We have all these cheat codes that are unfiltered, that, yes, help with the business, but more importantly, what's the point of success if you're miserable, Right. Personally, and I think we had a heightened sense of partnership because of the business. But any entrepreneur who has a relationship they care about needs to invest in that relationship. Otherwise it will just go away. And for us, it meant coming up with cheat codes that worked for us, that let us build the relationship outside of just the company. And so date nights on Wednesday and Saturday nights, standing sitters when we could afford it. Communication, how we got away once a year together. So we tried to lean into all of those cheat codes that helped us not only build a business, but now that our youngest is going to college, actually build a life that we like and a partnership that not only do we love each other, but we actually like each other. We like spending time together. And the last thing I'll say is the cheat code that really is most important is just communication, transparency. And I think that that part of our relationship has kept us going and it lets us get through the bad times. And as an entrepreneur, shoveling shit, right, there are a lot of bad times. So if you can't fight well with your spouse or your co founder and move on, you can't have the hard conversations. It's going to be a very difficult life.

Absolutely. And then I know you, you mentioned the book title for those that are listening. So the book for context, Shoveling shit and the subtitle a love story about the entrepreneur's messy path to success. It really is. And as you both said, as I was reading the book, the love story and the intertwined of business problems, personal problems, I learned so much about how you both think. And I want to ask you both, like, what was the moment when you both realized, like, ah, we need to write this book. And I will say the co author dynamic of, you know, hearing from both of you, it really was such a unique read for me. And I'm not just saying this because you both are here I was telling my wife Jacqueline when I was diving in, I'm like, you have to read this book, like literally, like hearing Mike's perspective and Cass's perspective, like it was a continuous conversation that I think whether you're in business with your spouse or not, you can learn so much from the dynamic. And I want to ask you both, when did you decide, like, hey, we need to write this book and what was the process for you both when it comes to the dynamic of not only starting a business and having children, but now co authoring a book together on this new journey?

I think it started, you know, we give. We love entrepreneurs, let's just say that. And so we're always trying to help any entrepreneur, whether it's someone that we've invested in or not. We just feel like you have to Give back to this incredible community. And we need more entrepreneurs. Right. So we always do it. And I just started, you know, keeping one of those, like, notes on my computer that had all the lessons that I thought were really important that Mike and I kept saying over and over and over again to every entrepreneur who would ask. So the book didn't take us a long time to write because we had the scaffolding, but I knew I always wanted to write it. I think Mike wanted to do a podcast. And I kept saying, like, let's amplify this a little bit more. So in that if we ever did a podcast, it would get out there because the goal is to help as many entrepreneurs as possible.

Yeah. So I would say I got dragged into the project. I went to journalism school. I knew that writing a book would mean potentially me writing more of it, which is fine, but it was never on my bucket list. Once we started digging in, I think I got more into it or just as much into it. And the reason is because it just became really rewarding. After the first chapter, which was relatively painful. Working with Cast, we got into a floor flow because we normally don't work together. I do more of the sales and the vision and product and raising money. And she does everything, runs the company. Hr, pr, marketing. And so what I really got out of the book was I saw how. I think I'm here.

You lag a little bit, but I can hear you now.

Oh, good. As we wrote the book, I think what I got out of it was this evolution that I had, which a lot of men have, which is this realization that vulnerability is important, that knowing your strengths and weaknesses. I look at the first few chapters and let's just say I wasn't very aware of. I would do what CAST would later call shining the turd on everything, no matter how bad things would be. Like, oh, it's not that bad. Like, we're crushing it, even though we like no customers. And like, you know, reality was different. And so, like many men, I had this, like, traditional model of masculinity when we started, which was like stoicism and self reliance and dominance. And, you know, I think that I was able to come up with a better type of being a man, which had to do with listening and owning my mistakes, taking responsibility. And that not only happened at home, but also transcended home into being a better leader, a better entrepreneur. And I think that imbalanced life, especially for me. Cass was born with a spreadsheet in her hand, like, super organized, but for someone who I think came into their own a little later, like many men do. That evolution that we outline in the book of dating, starting companies, being parents, investors, now kind of being parents, so to speak, to other entrepreneurs, that's what I got out of it, which was so rewarding.

Oh, that's so great to hear. I appreciate you both sharing that. And just to pivot the conversation a little bit, one thing that I not only loved about the book, but the companies and most importantly, the domain. Golf.com? i'm someone that my new company is called listener.com and it took probably 10 months to hunt down this domain. And my Instagram is just my first name, Casey. And domains and IP have always been so interesting to me on the stories and just why people do what they do in that space. And I would love for you both to take us back to and for people listening, if they aren't familiar, like where what Golf.com was when it started and what it evolved into. And also I'd love to hear the story of the domain and how that came about in the early days of the company.

I'll take that first part. So it was 1998, and I was working for the interactive arm of Leo Burnett called Giant Step, and our co founder, Mike Casper, was there, and Mike and I dated. And the dates were playing golf. So we were avid golfers, but we were recreational golfers. And that meant that those were cheaper courses. But if you wanted to have a handicap, you had to go back to the same course because there was a physical box there and you would enter in your handicap. So it forced you to go back to the same course, which I just thought was crazy. I also tracked all of my stats because my senior year in college, I walked onto the golf team. So the idea came about in that how can we help all these crazy avid golfers who want to track their game? They want USGA handicaps in an easier way right online. They want to watch scores at that time, like the Masters. They wouldn't allow any, you know, live scoring online. So we were the. We became the only place you could get live scoring and booking tee times and understanding courses and searching for them. So that was the real catalyst to starting golf.com and then, Mike, you talk about the domain.

Yeah. So this was not up and to the right. This was early Internet. And what that meant was we're figuring it out as we went. There was USA Today and a few other sites, but we started out, there were not a lot of vertical sites. You had kind of search engines. But there weren't the deep content sites and commerce sites you see today. Amazon was only selling books at the time and not even doing it that well. And so we looked at how do we get big fast and we actually sold the company about a year and a half after we started to it. Sequoia backed company. Sequoia is a just legendary VC firm that backed Google and all these big companies and it was a dot com craze and eToys and pets.com, and they were multibillion dollar businesses. We were a very dangerous combination of very optimistic idealist and nai and we just assumed everything was up and to the right. We hadn't lived through a major shock, right? Cause we're 22 years old, I'm 22 Cas, let's just say is a little what they call older. And we sold the business and April 2000 happened. Everything crashed, they lost their funding, they didn't go public. The company we sold to, they're supposed to go public. And when we reformed the business there happened to be this company, NBC that owned golf.com and they were broadcasting the U.S. open. They had a golf business. But someone within the halls of Rockefeller center said this Internet thing is not going to be popular. And so let's sell golf.com oh man. We were prepared to bid up to a million dollars in a court run auction because they had inherited it through a bankruptcy of one of their companies. And we got it for $289,000. And I, yeah, I'd be lying to say it was competitive bidding. And that with a combination of the luck of Tiger woods, this kid before he was Tiger shows up. He was Tiger, no one knew him, shows up to the Masters, wins by over 10 strokes and before you know it, he's basically a global superstar like Taylor Swift. People forget that at the time you say Tiger anywhere in the world. Europe, China, us, you know who you're talking about. And we just rode Tiger and his sponsors and Phil Mickelson and sold that for $25 million, which still is a lot of money to us. But at the time we were like, you know, we didn't have a lot of money. And it was like, man oh man, we will never make more than this. This is huge. That's what we know. We'd sell business for a billion dollars and part of other stuff. But the what we learned early on and what we tell every entrepreneur is just do it, just go for it. Like if you want to do your own thing, do your own thing. Don't talk about it, just launch. And what you learn by getting kicked in the face as you shovel shit is what's going to power you and those contacts that you build and just the strategies. And yeah, we hope that a few ideas of the book help accelerate you. And the good news, if you read the book, you read every one of our mistakes. So it's not just shits and giggles in this book, as you know, of course, it's the ugly stuff.

Yeah. And again, I appreciate you both sharing that and even too hearing the Domain, but something you mentioned, which I know you go more in depth on in the book. So you guys sold a company to this Sequoia backed company. Obviously the plan was up and to the right and they go under and you get, you buy the business back or you get the business back and you sort of like say, hey, round two, we're gonna go back at this again. And I, I found that part of the story so interesting because, you know, when you, as you would say, like, you're shoveling shit, you are going through this process of everything just kind of hit the fan. What were the conversations back then between you two during this really transitionary process? Like, was there like, what the doubt, the future, like, bring us to that moment of, you know, after you sell and then this kind of goes south. What happens between the relationship between you two? Did anything change then?

I don't think anything changed at all. This was, I think March of 2000 and the entire economy was tanking. Right. The boom was over. I don't think anything was changing. I remember that what was propelling me was just anger of losing. I don't like to lose and I certainly didn't like to lose, not on my own terms. And that's the real athlete and competitiveness inside me. And I also felt an immense amount of responsibility to these employees who we were taking care of their livelihood. Right. Like they needed the money. We were used to no money back then. What people don't remember is entrepreneurs, entrepreneurs and founders were not paid anything to start a company. You got your equity and you moved on. Nowadays it's very, very different. So we weren't as shocked about that as we were. How are we going to tell every employee? And because we were so transparent and did it in, you know, just a very open way, no one left, which was amazing. And then Mike said, let's do this, let's hit the road. And that's what the three of us did. We just got on the road and said, we're going to find money, and we're not coming back until we do.

Yeah. And I remember you raised like $1.5 million during that transitionary period. And speaking of just raising money, not only was that the beginning of the long journey, but you guys have raised hundreds of millions of dollars across companies. And I want to hear from you both and starting with you, Cas, when it comes. And also, I know Mike, you said you do more the fundraising side of things, but when it comes to raising money, what have you learned over the years regarding raising money that founders should apply today in this environment, 2025? Because obviously things have changed so much from when you first started raising money and the markets. And just curious to know just this over overarching viewpoint of fundraising advice.

I think there's two things for me. One, when you're really nervous and have never done it before, the only thing, the worst case scenario is they say no. So you have to kind of break down that fear and just go for it. Because surprisingly, people might say yes. And the second part, which I know Mike will dive into more, is that if you just cold call someone and just say, like, hey, I've got this investment, it's not going to go well. You need to build relationships over time. And Mike was like, definitely the king of this. And I'll let him explain it.

Yeah. So in the book we really. Which is written more for entrepreneurs who are selling real estate or running pizza places or hair salons or it's not built for like tech companies, even though all of the cheat codes were kind of gotten through those types of businesses. And it's definitely applicable. The best way to raise money is customers. So provide a product or service that people want to buy and use kind of revenue to fund the business. If you're building software, if you're doing something that takes investment, you're going to have to go raise money. I tell all entrepreneurs the best way to ditch the fear of raising money is exposure therapy. Just go do it. So if you weren't scared to raise money, you wouldn't be human. You'd be like a psycho. Right. Because it's a really unnatural thing to go to friends and family first, which is where most of us went. You know, I went to my grandfather and he invested $5,000, which to me I was like, man, he's going to like go under if I lose this money. Right. I was 19 when I did it. But you just have to do it and you have to be. You have to believe in what you're doing and if you don't think that it's a good plan, it's definitely not a good plan. So as entrepreneurs, we're optimistic, we think things are going to work out, but oftentimes we don't listen to our gut and say, wow, this makes no sense at all. And the last thing you want to do is raise money when it makes no sense at all. And I've done that. I've raised $12 million for a business that failed pretty spectacularly so far. And I didn't think it through. And people just assumed, oh, he's been successful, we might as well back him. And so my kind of cheat code for raising money is never be raising money, but always be raising money. So you're never asking for money. Or very rarely you're saying, how can I help you? How can you build real relationships with investors? You trust, investors you respect, and everyone has needs. So you may know some stuff about AI that investors need. You may know some entrepreneurs who investors are trying to invest in. You may be hosting an event, you know, that you could invite some investors to. I used to create a pretty epic board letter, like in written form, not a deck, even though we had financials. And it would be the narrative of the business. Because if I couldn't convince myself it made sense, I couldn't convince anyone else. Employees, with the hundreds of employees, you have to have your strategy super focused. I would take that letter, strip out all of the really bad stuff. So I would communicate in this letter, like, the good, the bad, and the ugly. And if it was and it was.

Ugly and not all the bad stuff, meaning more like the confidential stuff. Right.

Well, anything that's like, you really don't want to get out to the world. Like, anything that's like, you know, a lot of times at companies, you're sitting around the kitchen table talking about bad stuff, like.

Yeah.

And so I would send it out as kind of an update that, hey, just want to keep you updated. And by the time you ask for money, you are going to increase your conversion rate. If the person you're asking likes you, let's just say that, and respects you. And this is something that I do today. You know, I do a lot of outbound cold calling, not just for the book, but just for my investments and over a hundred investments. And I'm always looking at as, how can I help this person? Because I know the more I give, the more we're going to get. And some of our biggest relationships and most cherished relationships started with us giving. And that's it we didn't even think about taking.

Yeah, that's such a great perspective. And I think too it goes to. I know one of your dear friends, Gary Vee, is the jab, jab, jab, right, hook, right. The idea of giving and giving and giving without asking for anything in return and something that I think you both would appreciate that I wanted to bring up. And I know the story of Gary, which we'll get to in a moment, which I loved, was awesome. So Gary, his book, Crushing it was really what inspired to start this podcast when I was 16 years old, I was a sophomore in high school, I was coming out of a neck race where I was nearly paralyzed playing football and go from this young 16 year old kid that grew up an athlete to never being able to play football again. Depressed, don't know what I want to do with my life. Kind of stumble upon the Gary Vee universe in like 2016, 2017. And the last chapter of his book was of Crushing. It was about podcasting. And as this naive 17 year old kid, I have my Apple headphones and just start walking in a circle. I'm like, all right, this is episode one of the podcast and the goal is to meet, to learn people, to learn things from successful entrepreneurs, to build a network and hopefully create some business opportunity one day. And, um, I mentioned this because it's relating to like fundraising for my, my last startup. It was like three, four years into running the podcast. Probably did like 250 interviews up until this point. And when I went to go raise for my last company, funny that the number was very. This is why I love the book so much. Like, I find so much relatability to it. We raised $1.5 million for my last company, MediaKits.com and it was from 37 angel investors and pretty much 90% of them were past guests on my podcast. People who I've built relationships with, people who I've planted seeds with. That's so awesome and thank you. And it was really like that. Again, the jab, jab, jab, right, hook, right. I would come to them like, hey, I just want to get your thoughts on this project we're working on. It wasn't about raising money, wasn't a cold call. It was just like, hey, I want your feedback and talk to them about the opportunity. And I think for me that was the full circle moment of not only the podcast, but the vision I had when I was 17. I was like, meet great people. Hopefully create business opportunity. And I think it comes full circle. To this conversation where if it wasn't for you both kind of hosting what people now know as Gary Vee, back in those early days, he's inspired so many people and hearing how influential you both were, part of his story was so awesome. So I just wanted to share that story with you both because I find it very relevant to the book and how you guys think about business in the world.

What's interesting about. And we don't know each other incredibly well. We've been fans from a distance, hope to get to know you even more, but you have done something you're good at over and over and over and over again, and that's the key to life. Like, find something you're good at and exploit it to the benefit of the world. And so too many people do 10 episodes or, you know, they launch, but they don't pivot or they launch and they're like, oh, we don't have any customers. So we're just packing it up, right? And so if you can continue doing what you do every day, every week, every month, every quarter, every year for a decade, you can do anything. And that's what we saw Gary do. He showed up to our office and he had this little show called Wine Library tv. And I say it's little because at the time it was little. It just happened to be one of the only ones on YouTube. And he basically said, I've been working for my father for 20 years, since I was like, 13. I've never made more than 100 grand, and I don't have money for an office. Can I use a third of your office space, your conference room, for my office? And so for someone who's like, jab, jab, jab, Right hook. We just got the right hook. Off the bat, right out of the gate, I said yes. But then I was nervous what Cass was going to say. Cass, you want to talk about your love relationship with Gary?

Gary and I are, like, really close brother and sister. That's how I, you know, like an adoring brother and sister. Not like, you know, you're kind of sometimes family of origin. But, like, he is very hard to say no to. And he cajoles you to, like, come on, you can say yes. This is not going to be a bad thing. We'll play ping pong every day. And that's what it was like. So the good news is that we got a front row seat to see him start to build his empire with AJ, his brother. And we also got a great partner in terms of culture, because the way he treats people is the way we treat people. The bad news is he just happened to have our only conference room for months and months and we didn't kick him out.

It was the, you know, he filled up this conference room like double decker desks, like it was crazy. And the fire department showed up for an inspection one day and they looked in the conference room, they're like, are these refugees? Like, what's going on here? And they basically said, if we're going to come back tomorrow, these people aren't gone. You know, I'm going to have to write you up. And we're like, oh man, we don't want to have to go to court and do all that.

So.

But at that time he had focused on landing customers and he's the best salesperson ever. And he had a bunch of like 12 year olds doing the work, doing like social media marketing. They, they seemed to be 12. It turns out they weren't. We know Marcus and these guys.

Yeah, yeah.

Like fast forward. These are our family now. Right. And so, you know, Gary did what all entrepreneurs do. He just does it really fast. So what he's built in 16 years or 17 years is amazing. And there's a lot of lessons in that for everyone.

Absolutely. And hearing that story when I first came across it, I think it's just, it speaks to the character of the both of you. Right. To one third of the office space. Give it to a friend. And most importantly, the belief that you both had and the love for the game of business and entrepreneurship and even how you both live your life today with what you do as investors and obviously like writing the book. It's, it's very evident to see that this is how you both have lived your life for, you know, since those early days. So very cool to hear. Let's talk about Buddy Media. So first off, you, you sell golf.com as you mentioned, $25 million and then what's next? This whole next era of social media marketing and being there in the early days, it, it actually reminds me of just. And I want to draw the parallel to this modern era of AI and the early innings of where this is going. What did you see back then in social media and sort of the prediction for the future and how is that relevant to AI today and how companies should be thinking about the opportunities ahead.

Yeah, so I do most of the idea stuff. And so this was not Cass idea. I was blown away by Mark Zuckerberg. On May 24, 2007, he launched the Facebook platform and he did it by inviting developers to build applications that were social. And so up to this moment, the Internet was relatively. It was basically a one player game. You basically searched, you played solitaire, you maybe went into chat rooms. But it wasn't. The idea of social was just kind of like these online communities, like the. Well, I wouldn't even say MySpace, which was bigger than Facebook at the time, was very social. No one knew who you were. You were anonymous, right?

Yeah.

And so when he did this, it just hit me really hard. And I had a student business in college. I was an early user of Facebook. I loved it because it let guys connect with other guys without picking up the phone. Right. Like all my friends who were on it, I could keep up with without. And at least dudes we don't love, like chatting on the phone. Or at least I didn't at the time. And so when he released it, I just saw a world where like, games would be social and marketing would be social. And this whole idea of birds of a feather flock together. How do you kind of get your customers to invite their friend into your brand and the brand universe? Right. And so we pivoted a bunch of times, but we were really believers in the idea that if we connect people in one platform, good things will happen. Now we can talk about what happened. The business. Yes. We had a billion dollar exit and it was great. I wouldn't say Facebook has been a net positive for the world. And so it has turned out very differently than what we expected. But that business and the idea, we just put ourselves in a. In front of a big pile of money. And we had nine out of the top 10 global brands using our software to do their social marketing. And in many ways, we helped invent what then Cambridge Analytica and others weaponized starting in 2016. And it hasn't really stopped.

Yeah. Wow. And there's so much to dive into there of when you say not a net positive. I'm curious to know the viewpoint of what has Facebook done? Well, what has Facebook done bad and is the platform overall in your viewpoint?

Facebook.

I can start. Oh, sorry, Mike. Go ahead.

Yeah, I mean, Facebook has made money, and they're very good at making money. And the reason is they optimize for engagement. The flip side is when you optimize for engagement, negativity and hatred is much more engaging online. And so because they have never optimized for anything other than engagement, they've created an environment which is toxic for mental health. It's ruined democracy to a certain extent. Not on its Own, but it's been an accelerator, it's been the, it's fueled the fire. And looking back, I think the world would potentially be better without the platform. Having said that, we're not Luddites, so we believe in progress, we believe in technology. We believe that technology isn't good or bad. It can be used for good and bad. Unfortunately, the people who use it for bad are oftentimes better. And it's why we love Gary and other entrepreneurs who take a position of positivity with everything that they do. And even though the book is called Shoveling Shit, which sounds negative, it's a love story. It's this love affair with hard work, these social networks, I think it's just made it hard. We've seen our kids who two in college, one graduated, we'll have two in college in the fall. It just made it harder to navigate social interactions.

Anything on that end? Cas?

I agree with everything Mike said. And little did we know back then, right. What we were actually doing, we just thought it was just such a new innovative way to market to customers. And now as you know, it's actually the pandemic of the current generation. Right. And the generations behind us. It is a, almost like a disease. Social media to. You get addicted, you get the hits really quickly and your, you know, hours go by. So. And these kids over the last 10 years have been hit by technology plus Covid. Right. So they've really lost a lot of what you and I just, and Mike just called reps, like reps of interactions, reps of knowing what their teachers are thinking or reading, body affect and tone, understanding tone and looking up and, and just sitting and listening and learning. So that's what we think.

Yeah. No, I appreciate this perspective on that and immensely. And I think too, I, I have a nine year old niece and I think the idea of like having kids and how it affects children definitely stems a whole other thought process than I do with my own like personal perspective on. And I think, you know, my niece, obviously she's not on social media, but I'm like, okay, in the coming years ahead, like how is that going to affect her?

Right. Think about self esteem.

Right? Absolutely. So I definitely, I get that.

And that. And that's also why we wanted to write the book in such a different way and a raw way is because we wanted to show people that it's really just getting punched in the face every day. Right. And you have like maybe one win a day if you're lucky, but there's, there's there. Everyone thinks it's like all this, you know, glamour. It's not glamour. It is. You are literally digging in the trenches every single day. And if we could open up, you know, and show everybody what it really is like, we thought that would be much better and more realistic picture.

Yeah, I think you said it very, you know, to the point. The rawness that I've. I have this whole bookshelf right in front of me that you can't see, and I have some behind me as well. And my favorite thing is this biography. That's all I read. And I think this, the story that you both tell and the rawness that comes with it. I want to ask this next question about the business, about the exit. But most importantly, hearing the story and the progress and the challenges, the punches in the face every day to get to, as you described Mike, a billion dollar exit. I want to ask when you guys got to that moment together as a couple that have been on this journey for a very long time, how did that feel of this big exit? You've struggled. You've gotten punched in the face every single day. The first company, you sell it, everything crashes, you start again, you have a win and even one thing to reference. And I don't want to give away the whole book, but I remember when you guys were starting Buddy Media, you've made some money from the acquisition, but then you bought an apartment. And as you said, I believe, Mike, you were cash poor. And it was like, okay, how are we going to go figure this out? How are we going to feed the babies? How are we going to feed the business? And when you finally get to this acquisition, take me back as a couple, as a husband and wife, how are you both feeling? And how did this not only change your life, but the relationship and just your viewpoint on life?

I think we both were trying to survive at that point. Because anyone who's done an acquisition knows that there's this process called due diligence. And it is horrific. And if you've been in business longer than a year, like, get ready for most of your waking hours to be taken by this process. And then your other bandwidth, which is what Mike and I would spend our time, like, talking about is like, do you think this is really going to happen? Like, is there anything we're missing? Like, what do you think this means? And you know, your, your bandwidth is kind of consumed by that. And when it's not consumed by that, it's consumed by your family, either each other. And Mike was on the road the Whole time. And I was holding down the fort with basically three kids under, I think it was 10 at the time, and a new puppy that Mike so courageously decided to get. And it was hard. It was a wild ride of us trying to survive. And we knew we needed help, and that's why we had brought, you know, we had hired Susan St. Leger. But then things just get even more crazy. You think you can't get to the next level, and it just becomes absolutely beyond crazy in terms of all the things that you're trying to do and deliver. And I think when the day came and we had this huge party and every employee flew in from it from all around the world, and we had a stage and Mike walked on because he had negotiated this incredible deal which really gave every single person a slice of the pie. Even vendors got slices, which was really lovely. And then we were kind of like, okay, what's next? Like, who's taken our kids to the doctor's appointments the next day? Who's dropping someone off here at their sports class or whatever? It doesn't go away. And I think entrepreneurs have an endurance for suffering, which helps you just keep going.

Absolutely. Very beautiful. And well said. What about from your perspective, Mike?

Yeah. So success has never been about money for us. Even though money, it turns out, is awesome and it empowers you to do a lot of stuff and it gives you freedom. And I felt numb, like, walking off that stage. Heading home with Cass, I was 40 pounds overweight. I'd been traveling the world. Cass and I had not been doing a regular date night Wednesday and Saturday because of the deal and the company. And there was a misery that I had grown used to, and there was nothing I'd rather do in life than what I did. So it's not like the misery or the fear I feel with sharks in the ocean where, like, I never want to be with them again. It's basically this love affair that we had with suffering and with 19 hour flights to our Singapore office and every night dinner with clients, which the first few you may like, but then do it 200 times a year and you got £40 and you start shaming yourself. Right? And so we knew that we were lucky to be able to build companies, do it together, celebrate together, make life changing money for us and our generations to come. And we needed to get our health in order. We needed to get our family in order. There was a lot of healing and so a lot of what we learned in terms of after how to heal, how to get kind of in Shape, physically, mentally, our relationship. Hopefully it doesn't come across that it was always great every day with Cass and I. Like any co founder relationship, any partnership, any marriage, it's a constant thing you have to work on, and work is not always fun. And so it's just we wanted to capture this kind of euphoria and misery, and that's why we kind of named it Shoveling Shit. A Love Story. It's not a negative thing. If I were to ask you, like, how hard it is, you kind of go through the list of everything you've done and kind of, you know exactly where you're hurting. And then if the next question is like, what would you rather do? Nothing. Because inside these companies is where a lot of us find our purpose. It's not the only way. There are a lot of other ways if you want to, you know, in the nonprofit space, you know, hard work is a virtue. So go work for a company. Put your head down like there is a lot of other places. But for entrepreneurs, this is where we find our passion and purpose. That makes us get up in the morning on days when we don't want to go talk to customers who are yelling at us. We don't want to deal with employees who are unhappy. We don't want to admit to ourselves that we're about to run out of money.

Yeah, very. I appreciate the perspective immensely. And I have a couple more questions before we wrap up here. I mean, I could talk to you both for hours. I got to start doing the Lex Friedman style four hour podcast, and we'll.

Have to run it back.

You know, having not only accomplished so much, but been through so much together. And on this new journey of. With the book Shoveling Shit coming out soon for you both, I'll start with you, Kaz. What excites you the most as you think about the future with each other? Children, business. What's something that's just keeping you up at night that you're excited about moving into this next decade and beyond?

Well, I have a couple things. First of all, our oldest graduated from college this past Saturday, so that was.

Congratulations.

Thank you. That's amazing. Yeah. One got through college. And I keep thinking back on the day that we all showed up for each other in our little nuclear family, which was really awesome. And we also had, obviously, Mike's parents and my parents and my cousin. But it was just nice to see that. So I look forward to more of those times, and I'm actually looking forward to having more time to give back. I think Mike And I thought about the first 50 years of our life as just earning. Like you're earning friendships and relationships you're building, you know, our marriage, we created a family, and we're earning a reputation. And now I think it really wants to be the other way, where we give back and make bigger impacts. I want to go, you know, stay committed to Cycle for Survival, which is our biggest charitable organization. And I look forward to. I think I look forward to traveling without feeling guilty that the kids are at home. I think that's really a big thing for me. And not making any more food for anyone. Sorry, Mike. That includes you.

Oh, man. What do you have to say about that, Mike? And what excites you?

That was an interesting comment because I do most of the cooking.

That's so not true. You do most of the cooking, but I'm the one who always has to plan it and get the groceries and all that.

I'm not saying I do the planning.

I'm not the operator, so I do not want to do that anymore.

We don't have to love that perspective.

There, but I'm happy to cook for it. You know, I think after we sold Buddy Media, we went into investing, and it's been an incredible run. I mean, we've seen companies we seeded, you know, exceed all of. Not only our expectations, but way beyond what we ever did. Right. I look at a company like Scopely, and we were the first investor in Walter Driver, and they sold the business for $5 billion in cash, and it was awesome. And like. Like, we love that. But at the end of the day, we got away from. And we know why. We got away from shoveling. We got away. We had kids. We had to kind of double back and really pay attention to, which I wouldn't say we did. While we were doing Buddy Media, we were very unfocused. We just tried to get by. And I think what I'm looking forward to do is doing what entrepreneurs do, which is picking up a shovel, doing the hard stuff. And I can't tell you how excited we were we are about the book, because people look at us, they're like, why are you working so hard? And why are you doing all this speaking and all these podcasts? And it feels like we felt at Buddy Media, we have a great team. We're working harder than we've worked since Buddy Media, and that's just kind of wet our appetite for hard work, smarter work. We're capitalists, so we like making money. We like giving back, and the impact that. That, like, if you want to do good in the world, make a boatload of cash. Unfortunately, some of the people who have, like, we don't see them, like, building hospitals and giving back, but a lot we are. Look at Marc Benioff. Look at a lot of, you know, the entrepreneurs that we all respect, they. You just can't say they're not making their communities better. And that's where it all starts. So we made launch companies. I want to do 10 pizza places. Cass doesn't. So we got to have that conversation. I don't think we'll write another book. We may do a show, but we look at what you've done.

I'm a big fan of that idea. All day.

We look at what you've done, and we're not going to do it unless we have a plan and we could break through. It's very difficult to break through now, but a challenge like that, we're like, okay, let's go. And so it's.

You have my stamp of approval on a show together, I'd be the number one power listener. So.

Well, we. I mean, we don't do anything unless we do it right, of course. So how we approach this book is like any business. And, you know, with a little luck, it could be a bestseller. And we'll be really proud of that. Not because it matters, but because we want people to read it, we want people to experience it. And we're going to do stuff that requires a beginner's mind and will make us miserable. But we hope to find our next 50 years the passion and the purpose in whatever we do next. And we really look at it. The one thing we share with Gary is a long horizon. So it's not about quick wins. Cheat codes are how do you kind of avoid mistakes, but you still have to do the work right. These aren't shortcuts. They're just hopefully, secrets that will help you work harder, which is what AI does. And we think that if we could help be a part of the cure of cancer, launch businesses that matter, support entrepreneurs, and share the wisdom of all of our friends, that could be a good next 50 years.

Absolutely. Very beautiful. And last question. We can make these quick. It's two. Part one is I would what is something? And I want you to ask or tell each other this. What is something you believe you don't tell each other enough? And what would be your biggest piece of advice to me as a newlywed running businesses with my partner in this next phase of my life?

I think one of the things that that Mike and I have concentrated on in the last like five years is saying thank you for the little things. And so I think effort counts. And so acknowledging when someone drives the two hours instead of the other person who just got to sit there and check emails and move their work day forward, if someone made dinner, the little things I think count. And that acknowledgment counts.

I love that.

And something that's still hard for me that I'm working on is saying sorry. So saying sorry when I mess up, being specific about it, reflecting how the actions impacted negatively and sharing a plan to ensure it either doesn't happen again or is minimized. And I think that it's one thing to mess up, which we do, men and women, but owning it and being specific about it. So not oh, sorry, sorry, sorry, sorry. That's what I used to do. But like I'm sorry for doing this. I know it caused this pain. I'm going to slow down and make sure that before I say something or do something reactive like that, I'm going to try my best to stop it. I'm not going to guarantee it. And so that has been a big. Whenever I do that, things feel better and whenever I don't, it just gets buried and builds up until it inappropriately comes out at another time. And so Cass is very good at saying sorry and moving on. I don't know if it's a guy thing, but I'm a little less so I got it.

I appreciate you both sharing that. And as we wrap up here, I want to ask where is the best place for everyone to learn more about the book? To buy the book. And then I also saw you guys are doing a lot of events and co hosting some awesome events with founders and I'd love for you both to speak on the book. But also these event opportunities which I found very interesting.

So right now everyone can go to pre order it until June 3rd at Amazon. Just look up the title Shoveling shit under the books and it'll come right up. So that's where we'd love for people to go.

And anyone who buys a book becomes a if they want. So you have to proactively join. We don't force anyone becomes a member of the founders farm community and we have regular meetings. We invite epic entrepreneurs to come present on different topics and it's been a community, although it's small right. It's like a thousand people right now who have joined. They're helping each other out and they're selling to each other which is Great.

That's great.

Like to see, like, business being generated and so entrepreneurs helping each other out, which may be as simple as giving them business or as complicated as helping them through a sticky situation. That's going to be a part of everything we do going forward.

I love that. And for the listeners that have made it this far that are still listening, I will be sure to link down the book down below, and of course, Mike and Cass, all your socials. And before we wrap up, I just want to say again, and I said it many times, but thank you so much, both of you, for being on the show today and for writing this book. And as I said, it came to a point in my life at a point where I feel that I needed to hear a lot of what you both discussed and the story, and it just really resonated. So thank you both so much for writing this incredible book. I've already told so many friends about it personally and cannot wait for my audience to dive more deeper into the story. So thank you again.

Thanks for having us. Appreciate you.

Yeah. And congrats on everything.

Thank you.