Kass and Michael Lazerow. $800M Exit: “Shoveling Shit” in Business and Marriage
Episode - 50
Kass and Michael Lazerow. $800M Exit: “Shoveling Shit” in Business and Marriage
VCs notoriously avoid investing in married couples, fearing that personal conflicts could sink the business.
Yet, the Lazerows defied that norm—building not just one, but two successful companies together, culminating in an $800M exit.
They didn’t just make it work; they mastered it—and then wrote a book about it.
Today, we’ll dive deep into what exactly they did to make it work—and what they wish they hadn’t.
What We Discussed:
00:00:01 - Introduction
00:00:14 - Learning from Failure vs. Success
00:00:27 - Building a Business as a Married Couple
00:01:08 - First Meeting and Early Impressions
00:02:30 - Life After an Exit
00:03:08 - Golf.com: The First Big Exit
00:06:58 - The Struggles of Entrepreneurship
00:09:14 - The Emotional Toll of Entrepreneurship
00:10:35 - Taking a Break After an Exit
00:11:14 - Was Their First Exit Life-Changing?
00:12:54 - Why Start Another Business?
00:14:31 - Entrepreneurship with Three Kids
00:16:47 - Why Entrepreneurs Keep Going
00:19:41 - Becoming Investors
00:23:20 - The Hardships Behind Entrepreneurship
00:28:17 - Coping with Post-Exit Stress
00:31:41 - Entrepreneurs and Mental Health
00:34:55 - Reframing Anxiety & ADHD as Superpowers
00:38:46 - The Dark Side of Entrepreneurship
00:44:01 - Work-Life Balance: Do They Have One?
00:48:01 - Michael’s Attempt at a Painting Career
00:50:12 - Filtering Opportunities
00:52:28 - Navigating Marriage After an Exit
00:55:15 - Raising Kids with Wealth
01:02:11 - Teaching Kids About Money and Responsibility
01:09:04 - The Purpose of Their Book
01:11:20 - Final Question: How Do You Want to Be Remembered?
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Anastasia: [00:00:01 - 00:00:11]
Welcome to Exit Paradox, where we explore what actually happens after a successful business exit. I'm your host, Anastasia Koroleva.
Michael Lazerow: [00:00:14 - 00:00:27]
And I think, you know, you learn so much more from adversity, challenges, failures than you did from success. Even though you come out of success thinking you're brilliant.
Anastasia: [00:00:27 - 00:01:06]
Venture capitalists tend to stay away from investing into married couples in fear that personal conflicts may derail the business. Yet Cass and Mike Lazzaro proved them wrong. They built not one, but two successful businesses, leading to an $800 million exit. Along the way, they mastered both business and marriage and wrote a book about it. Today, we will uncover their uniquely valuable insights. Mike, Cass, hello. Happy to see you here.
Kass Lazerow: [00:01:07 - 00:01:08]
Thanks for having us.
Anastasia: [00:01:08 - 00:01:39]
No, absolutely. You remember, first time we met, it was at this conference for post Exit founders called Chapter X in Miami. And all of us spoke there, and we were waiting for Mike Saylor to dive into Bitcoin. And then, Mike, you leaned over to me and you said, cass and I, we do everything together. And you gave me this cheeky smile, and I was like, oh, my God, my heart is lost. This was the moment when I just.
Michael Lazerow: [00:01:41 - 00:01:43]
Late night the night before.
Anastasia: [00:01:44 - 00:02:27]
I don't know about that, but your magic absolutely worked. And I got so curious, and my heart melted, and I was madly in love with both of you. And then obviously, Mike, you and I ran into each other at this longevity gym called Alchemist, and we ended up talking until they kicked us out. We were just carried away, and I was mesmerized by your story. And this is when I was like, oh, my God, I need to have these people on my podcast. They're such a treasure trove. So I'm so excited you're finally here, and we can dive into your life. We can get figure out the secrets to your amazing, interesting, uniquely balanced life.
Kass Lazerow: [00:02:28 - 00:02:30]
Amazing. Thank you.
Anastasia: [00:02:30 - 00:03:07]
As you know, this podcast focuses on what happens to entrepreneurs after they've completed their entrepreneurial cycle and they've lived through the exit with all its challenges and messiness and lack of predictability. And we try to learn from each other's lessons to see how we can all do it. Better yet, you have been in this situation for a very long time. You had several exits, both of you together. And of course, the biggest one you had, what was it like, you know, 20 years ago? No, no, I think your golf.com was 20 years ago, right?
Kass Lazerow: [00:03:07 - 00:03:08]
Yes.
Anastasia: [00:03:08 - 00:04:07]
Which want us to start talking about because it was your first, like, really big exit, but then you later had an even bigger one, you know, an almost 800 million one from Buddy Media. And that probably added a different level of complexity. And complexity is what I love. And we'll talk about it. So you are now wearing so many hats, you're entrepreneurs. You are speakers and authors. You just wrote a book about entrepreneurship called Shovelin Shit A Love Story, which I've pre ordered and just can't wait for you guys to publish. I definitely going to read it right away. And you are parents of three amazing kids. So we'll talk about all of it today. I really hope so. But let's start with that first exit from Golf.com, how it affected you, what you learned from it, how it all happened.
Kass Lazerow: [00:04:07 - 00:06:57]
I think it kind of started all back in 1997. I had moved to Chicago to live with Mike. And my first job there was working for the interactive arm of Leo Burnett at a company called Giant Step. And I was the director of new business and marketing and PR and kind of wanted to work for myself. I wanted to create a different kind of environment where things were more equitable, where people owned a slice of the pie, so to speak. And I had this idea, thanks to Mike's vision, that, that there was probably a way that I could track all of my golf scores and statistics online if I could just figure out how to lock it up on the Internet. And Mike's amazing and brilliant visionary traits and skills came into play. And he helped me come up with the idea for Golf.com, which was syndicating golf content across all of the big major news sites. And we started that in 97 and we didn't sell it until January 2006. And so we went through the big.com boom and then massive crash. And it was brutal, absolutely brutal, because after one year of being in business, we actually were acquired by a company called chipshot.com and they were out of Silicon Valley and they were backed by Sequoia. And the hope was that our content merged with their custom golf clubs would create this kind of behemoth in the golf space. And we were super excited. Our board was excited. They voted for the deal and it was an all stock deal and we moved forward. And that happened in 1999. It was December 23, 1999. By the spring in March, we actually got a call from the president of chipshop.com telling us that Sequoia pulled out and they were no longer going public and the company was bankrupt. And then he delivered the news that there was no more money to pay our payroll or any of our employees. So what I think maybe Most people don't understand is that the life of an entrepreneur is just shoveling shit all the time and you don't know what's going to be thrown at you and you just have to keep shoveling. And so despite the fact that we did get a good outcome, we had to start the company over.
Anastasia: [00:06:58 - 00:06:58]
Yeah.
Kass Lazerow: [00:06:59 - 00:07:26]
And Mike and I got on the road. We told our employees that we would figure out how we could pay them, but we had to get on the road and start raising money all over again and really recapping the whole entire company because we had lost everything. So whatever Mike and I put in, along with all of our angel investors and seed investors, that was wiped out. So that's really where it all began. I don't know, Mike, if you want to add anything, the only thing I.
Michael Lazerow: [00:07:26 - 00:08:39]
Would add is if you think of the AI frenzy right now, the Internet frenzy of the late 90s was probably 10 times more intense. So the global media was focused on Internet companies. In 1999, which is when we sold that company, there were 300 IPOs that raised 25 billion. But there were companies like eToys that would raise 200 million. The stock would quintuple in the first day. And so when we sold to an e commerce company, in our mind we were billionaires. We were going to go public, this was going to go to the moon. And we just got shit thrown on our face like, you know, they went out of business, all the funding dried up in the space and so. And we'd very little money. I was a journalism major, I'm 25 years old, didn't want to work for anyone else, so. And we're pot committed, meaning as a family, Meaning Cass and I are recently married. We're thinking about our future. It's not like one of us has a job making money and the other is an entrepreneur or other.
Kass Lazerow: [00:08:39 - 00:08:40]
Health insurance, right?
Michael Lazerow: [00:08:40 - 00:09:14]
Yeah, yeah. We don't have health insurance, we don't have money, we don't have safety net. And I think you learn so much more from adversity, challenges, failures than you did from success, even though you come out of success thinking you're brilliant. I think how we worked through golf.com, bought it back, ended up selling it for Time to Time Warner for 25 million. And then that put us on the path to starting more businesses. And then ultimately the close to billion dollar exit to Salesforce.
Anastasia: [00:09:14 - 00:09:19]
Why did you not stop? Why did you not consider safer paths?
Michael Lazerow: [00:09:19 - 00:10:35]
Well, let me make something clear. After we sold to Salesforce and I worked there for Four years. Incredible company. Marc Benioff, one of the all time great entrepreneurs. Definitely the entrepreneur of the cloud computing generation. I was tired. I had gained 40 pounds. I was cranky, I was traveling the world. And so I needed to take some time off and I thought that I would potentially retire. I started painting, I started doing kind of what most adults call hobbies. And I was miserable and I didn't have purpose. Cass and I were. It wasn't the best time for our relationship. And after a lot of soul searching individually and together, we realized working is what we do. It's how we built the life. It's how we find our purpose. It's how we model what we do to kids, to our kids and others. And so we jumped back in. And so it almost, it took us, you know, we had to fail. We had to succeed. We had to succeed. We had to kind of fail personally to be able to write this book and show the imbalanced life of the entrepreneur.
Anastasia: [00:10:35 - 00:10:35]
Yeah.
Michael Lazerow: [00:10:35 - 00:10:58]
And how there's no worse way to spend your day in terms of stress inbound, the amount of work. And there's no better way. So that's why it's shoveling shit. A love story. This is not a negative story. This is the story of hard work, grit, tenacity, and our love affair with each other and two entrepreneurs.
Anastasia: [00:10:58 - 00:11:13]
So, Mike, that happened after your second exit, though I don't want us to jump through a few super important years in your life. So when you did sell golf.com for 25 million, that had to be life changing for you financially?
Kass Lazerow: [00:11:14 - 00:12:20]
Wasn't really, you know, I look at it as we were really fortunate to gain a nest egg of money. But when we had to go back out on the road and raise new funds and start over, we didn't own the same amount of the company as we did before. We were really, really, really crammed down. So at the end of this journey, when we sold in January of 2006. I'm sorry, January. That's right, January of 2006, we had enough money that basically would have covered the salaries that we didn't make for those seven years. Because back then, what people didn't, I don't think people now realize, especially entrepreneurs, you weren't making a salary when you started a company. Right. So boards were really finicky and they basically wanted you to work for nothing but the sweat equity. So, you know, for two or three years we were making zero. Then I think each of us were making about $30,000 each. And then we kind of moved up from there to 50,000 or 80,000 max.
Anastasia: [00:12:20 - 00:12:21]
Yeah.
Kass Lazerow: [00:12:21 - 00:12:54]
But when you. When you kind of amortize that over seven and a half years, what we actually made was less than what we would have made in the market, you know, if we gotten paid salaries. So while it was a huge win for us and the new investors really did well, we were. We were kind of set on a path of. Of kind of breaking even, the way we looked at it. And we were able to. Which was really great. Able to kind of afford living in New York City, which is really expensive.
Anastasia: [00:12:54 - 00:13:04]
Oh, yeah. So would you say that your motivation for starting the next business just two years later was financial primarily?
Kass Lazerow: [00:13:04 - 00:14:22]
I don't think it was primarily financial. I think, you know, Mike had a short earn out at Time Warner. The actual company was Time Inc. That was owned by Time Warner at that time. And I went back. We had two kids at the time. I think we both. I think. I mean, I can talk for myself. I struggled with purpose. I absolutely love, you know, having my kids. And I was looking for something that drove me with a different purpose. I was always very motivated by helping others and teaching. And so I think by the time I was pregnant with our third child, our daughter Vivian, it was kind of a great time for me to step back into it, even though I just had her. Yeah, it was time for me mentally, because we were really tired. I described the Golf.com days as kind of limping. We were mostly alive and partly dead at all times because we were waiting for the industry to bounce back. And it wasn't really until Tiger woods and Phil Mickelson kind of reignited the golf craze that we had our exit.
Anastasia: [00:14:22 - 00:14:26]
Right. So. So you took two years off, basically between.
Kass Lazerow: [00:14:27 - 00:14:31]
Just about. Yeah. Yeah. Well, it was like, you know, year and three quarters. Yeah.
Anastasia: [00:14:31 - 00:14:36]
And you were ready even though you just had your third kid.
Kass Lazerow: [00:14:36 - 00:15:17]
I mean, I think the funny story is that the day that I gave birth, you know, I was wheeled at a C section and I was wheeled into the recovery room, and Mike happened to check his phone, and he said, oh, my God, I have an idea. And I. I joke around and say, you know, I thought that was like, oh, my gosh, I'm gonna get you pizza and sushi and soft cheeses and everything that you haven't been able to eat in the last 10 months. But it was that he had an idea for the next company. So while I was definitely shocked, I did follow him right into it. There was really no hesitation. Do you agree, Mike?
Michael Lazerow: [00:15:17 - 00:16:47]
100%. And I don' I don't think the money thing's interesting because, you know, I'd started a company in college called University Wire, which became Student Advantage and went public during the dot com craze. I was entrepreneurial in high school and grade school and I think our identity was we're just entrepreneurs. So it's what we do. It's not something that we choose, it's the path we're on. And so I was constantly looking for the next idea. And I think what we've done really well is together because I come up with a lot of ideas and very few end up as businesses together. We've been able to be early in several really generational waves. So if you think of the waves of like the Internet and social media and crypto and AI, we're early enough to be a leader, but not too early that we get the arrows in our back. And I think, you know, we're capitalists, we love making money, but at the end of the day, if you're doing it just for the money, that's not going to be what propels you to shovel every day. And if you look at our biggest exit, it was 20 some years after we started. Right. So, yeah, you know, it's a 25 year overnight success story. This isn't kind of something you can do if you're just in it for the quick win.
Anastasia: [00:16:47 - 00:17:33]
Yeah, no, absolutely. So, Cass, I want to go back to you because you make it sound so normal and casual that you just had a third kid and then you jumped into a second business when you already knew full well how difficult it is. Right. You did not have this naivety. Not only you knew, but you knew through a particularly hard experience of, you know, pulling your own company out of a bankruptcy. So I have three kids too, and I also continued building companies through, through that time. And I remember having a lot of guilt. Like I constantly felt like I was failing my kids and then when I was with my kids, I felt I was failing my businesses and my employees. How did you deal with that?
Kass Lazerow: [00:17:33 - 00:18:25]
I definitely, absolutely relate to what you're saying. And one of the things I think I came to understanding, or at least trying to accept was that I really only believed that I could do one thing well at a time. And I think, as many people have heard me say, I definitely went into the buddy media days saying to myself, I am unfortunately sacrificing my kids really early years in hopes that I can get back to them on a more full time basis and a more present basis later. And So I think I always had the guilt. And I said to myself, if I'm going to do this and I'm really going to be honest and try to get back to them, which is what I wanted, then I've got to be all in.
Anastasia: [00:18:25 - 00:18:26]
Yeah.
Kass Lazerow: [00:18:26 - 00:19:00]
And so, you know, I think personally that raising children is much harder than any day job, any entrepreneur job. Anything else, it's. Yeah, it's way, way, way harder. I, I say this all the time. You can't fire your kids. You can't put them on pips. You, you know, the, the skills you might learn in the office don't apply back to your family life. So in a lot of ways, work was comforting to me because it was, it was easier.
Anastasia: [00:19:00 - 00:19:09]
Yeah, yeah. That actually I can fully relate to. It's easier. And it also engages your brain, distracting you in a good way.
Kass Lazerow: [00:19:09 - 00:19:10]
Yes.
Anastasia: [00:19:10 - 00:19:41]
Feeding you, nourishing you in a good way. I think I only fully appreciated it after the fact, but those years when I had to combine both were extremely painful because of that guilt. All right, so let's then talk about that other hat you're wearing, which is investors, and the whole story of how you got into it, what you've learned along the way, and why you seem to prefer your identity of founders and entrepreneurs to your identity of investors, even though you still have it.
Michael Lazerow: [00:19:41 - 00:20:16]
So I'll take that. As entrepreneurs, you end up hanging out with entrepreneurs. Right. That's how we met. We were at an event and it turns out we're the same person. So three kids, you know, you thought about them, you had an option to go a more traditional route. Right. Like you were a high powered corporate lawyer and found entrepreneurship after that. And yeah, we happen to dive right into it. And when you hang out with entrepreneurs, they are often raising money.
Anastasia: [00:20:16 - 00:20:16]
Yeah.
Michael Lazerow: [00:20:17 - 00:23:02]
And when they're raising money and you like them, you like their vision, you, if you are fortunate enough to have resources, you obviously want to invest. And a lot of our entrepreneur friends invest in each other. Entrepreneurs who started funds will do each other's funds, and it really started there. And because we were around the Last Wave Web 2.0, we were fortunate enough to be able to, you know, invest early in some of the leading companies. So we pre, you know, pre ipo, Facebook and Tumblr and, you know, companies like that. And we have gone on to do over 100 investments. And we do it through our venture fund, Velvetsy Ventures, and, you know, our family office kind of off our own balance sheet. And we're addicted to entrepreneurs. We love the Energy. We love helping out, and we love making money. And we don't think that making money and loving what you do is mutually exclusive. We actually think we can love what we do and make money. So that's how we got into being investors. And we really used our personal investing as a platform to become more professional in our investing. So we did many deals and cut our teeth as board members and advisors before going out and asking people for money. And we felt like we had deal flow and more importantly, we could help the entrepreneurs. And we have loved working with companies like Scopoli that sold for $5 billion last year, or, you know, 2023. And, you know, Liquid Death is one of our companies that's doing phenomenally well, and a company called Carta Health, which is virtual cardiac rehab. And. And we just love being around building. And all entrepreneurs know that investing is a lot easier than working. So the shoveling of shit as investors is not as hard as the shoveling of shit as entrepreneurs. The great investors build companies and they are, you know, those investors are shoveling a lot of shit. But at the end of the day, writing a check to an entrepreneur is, you know, it's the biggest honor we could be given, someone saying that, I would like you to invest in me. We don't look at it as we're doing them a favor. We look at it as, you know, they are doing us a favor.
Kass Lazerow: [00:23:02 - 00:23:04]
They're giving us an opportunity.
Michael Lazerow: [00:23:04 - 00:23:13]
Yeah. Like when we were raising money, I was never asking for money. I was offering an opportunity to make boatloads of cash on the back of.
Anastasia: [00:23:13 - 00:23:17]
Yeah, because you're the one working capital. You're the ones who are doing the hard work.
Michael Lazerow: [00:23:18 - 00:23:20]
It's an opportunity we're offering them.
Anastasia: [00:23:20 - 00:24:17]
Yeah, and investing. Not money or not just money, but your time and your energy and your lives and sacrificing. Talking about sacrifice like you. It took me some time to define my sense of purpose and find it. And I know that everything shifted for me when I realized that that sense of purpose and that sense of fulfillment only happens when I sacrifice and I work hard. And that's when I realized why lots of charitable activities that I did soon after my first exit never gave me this sense of satisfaction. I actually felt very guilty about it. I thought something was wrong with me. And the reason I went back to building companies again was exactly that. Crystallizing and defining the sense of purpose as something that requires hard work, focus, and sacrifice. Would you agree with that?
Kass Lazerow: [00:24:18 - 00:24:59]
I've never thought of it that way. And I kind of do agree with it. I do think that there is something about the idea that you have to do something, you have to sacrifice other things. I think I liken it to again, training as an athlete, there's a huge amount of sacrifice you have to make. I remember my entire childhood missing most extracurricular activities and not doing anything socially. And so yeah, I think you're absolutely right. So I like the feeling of discipline and having to make difficult sacrifices. So I love that.
Anastasia: [00:24:59 - 00:25:35]
I just think if people embrace that, maybe it would be easier for post exit entrepreneurs to not be stuck in this limbo for years thinking, oh, can I get that sense of purpose back without actually working hard? Right. That's the biggest question. People don't want to work hard again, but they want to have the same level of satisfaction. I don't think it's possible. I think you just need to embrace the hardship if you want that sense of purpose. The sense of purpose and fulfillment is the reward you get for contributing at your very best to the society. That's how I see it.
Michael Lazerow: [00:25:35 - 00:28:17]
Well, that's the. Therein lies what we're trying to capture with shoveling shit, a love story that it is the shoveling of shit which is the purpose. That is the end in and of itself. Everything else that comes from the honor that you get and being able to spend your day shoveling shit is a bonus. But is the actual shoveling which matters and, and there will be consequences and an impact of that decision to your life, good and bad. And that's what we outlined. Like, you know, it's not all shits and giggles in the book. It's basically a lot of issues. Like I, you know, as you were talking about that I was taken back to like what should have been the culminating moment of our career, which is we had announced the deal to sell to Salesforce. We told the company and this is kind of June 2012. I walk onto a stage to just thundering ovation in a soho hotel and our employees are just going crazy. Cass is in the front row. My brother John, whom very close with is there. He was living in New York at the time. And I, what I remember is not just that, but Cass and I get into a car to go home to meet our kids for dinner. We didn't discuss like the money we would make or the opportunities or you know, we didn't gloat. We, you know, I think spoke about how lucky lucky we were to build and sell the company and how much we need to do to rebuild our life. We had you Know, one of our kids needed some attention. We, frankly, we weren't doing well. You know, I was traveling the world. We had offices in Singapore and London. And, like, when we're not connected and communicating, it's hard. It's harder for us to work. And the toll that. Five years getting to 50 million in annual recurring revenue with eight offices and all this stuff, the toll it took on our life. We were just starting to realize, and I think it took a few years for us to really get our groove back.
Anastasia: [00:28:18 - 00:28:23]
So what exactly did you do? What helped and what was a waste of time?
Kass Lazerow: [00:28:25 - 00:31:05]
Well, first of all, you know, I. Being the operator and kind of seeing two of our kids struggling in very different ways, I tried to learn to be present. I think that's when I started doing breath work and started trying to breathe, because I think I realized that when I am very high focus and multitasking and kind of being in operations mode, I don't breathe as well as I should. So, first of all, that helped. Second, you know, I was in therapy, right? So it's not like I. I stopped it while I was doing, you know, all the companies, but therapy definitely helped. But returning back to slowing down, I think was a big part of it because I was so. I think my whole body and. And my whole, like, nervous system was shot by the time we sold Buddy Media, because I had so many balls in the air and was worried about so many different things, especially the kids and then all of the employees that I felt responsible for and responsible to, that I had to kind of take everything one by one off my shoulders and kind of go through this exercise of literally visualizing. So I went back to the tools that I had learned as an athlete, which was like this visualization which some people just basically call meditation, right? You're just visualizing what. What you want to happen or. And taking things off my shoulders and realizing that I am no longer responsible for those things and I can let them go. I see a lot of entrepreneurs who, like you said, are stuck. And I think another part of it is because they haven't let go of some of the responsibilities, which becomes the. The record that gets played behind them at all times. So for me, it was that and also focusing on health because I. By the. By the end of Buddy Media, you know, Mike said he gained 40 pounds. I was probably 30 pounds overweight and doing everything I could to try to figure out what was going on. And it turned out that, yes, my stress system, my cortisol was high, and, you know, off the Charts. But I had very severe thyroid disease, which I was. Was undiagnosed. And so I spent the next 10 years trying to figure that out. And that's where I think every entrepreneur should start, is with health.
Anastasia: [00:31:05 - 00:31:41]
Yeah, no, I completely agree with you because people tend to underestimate the toll that building a business actually takes on our health and our mental health. And we're so busy, we are so driven, we're so into this, you know, solving the problems day to day that we just don't step back and we sacrifice our health without even thinking about it. And then what I see happen a lot is that afterwards, many post Exit founders don't actually take enough care of their health and they jump straight into another business just because they're uncomfortable, so unfamiliar.
Kass Lazerow: [00:31:41 - 00:31:41]
That's right.
Anastasia: [00:31:41 - 00:32:07]
And especially with mental health, even more than physical health, I think people are doing better with physical health. But mental health is so scary, so unfamiliar to so many of us. And I know you've mentioned it in your previous interviews that you have, each of you dealt separately with mental health diagnosis, and would you mind sharing how you embrace that, how you dealt with it through the whole journey?
Kass Lazerow: [00:32:07 - 00:33:36]
Absolutely. I'll start with, you know, I've had anxiety and bouts of depression my whole life. It runs in, you know, my family of origin and mine. My symptoms are of, you know, I will start to do more and more and more and more. That's like a coping mechanism for me is I, like you said, I never wanted to be comfortable with the feelings of being anxious. And so over time, and we're talking like 30 years of working on myself, I've learned to embrace it and then understand what are more positive and more impactful coping mechanisms. Right. Because you don't want to be doing more of the stuff that actually increases your anxiety and decreases your mental health. So, you know, that, like I said, all the tools that I've mentioned before, but the mental health thing is really scary because it can paralyze you. And the more and more you can get comfortable with, you know, not being shameful about it like I've had, I don't know why. And Mike, maybe you can agree with this or not, but I've never really been ashamed of my anxiety. I've tried to use it as a superpower. And when it's not being used for good, that's when it gets in the way. That's when I know it's taking over, if that makes sense. And I've got to step back and kind of concentrate more on it.
Anastasia: [00:33:36 - 00:33:42]
So how do you reframe your anxiety as superpower? What do you tell yourself?
Kass Lazerow: [00:33:42 - 00:34:45]
So the way I've thought about it is, and I think I tell a lot of college kids this, Right. I talk to my two sons, you know, friends is that everybody's got strengths and weaknesses. Right. You're born with whatever it is that you have and there's a reframing of how you can look at something. My anxiety of trying to make sure that I understand the path and what is the most efficient and way to move forward and how do I rally teams to move forward. That is a gift. But my mind could continuously think about the different paths. Right. So I chose purposely, and I think mindset is a choice. Right. So you have to start to choose how you think and you have to choose what you're going to reframe. So it's not always been like, how do I reframe something? It's the act of reframing that actually has made things better.
Anastasia: [00:34:45 - 00:34:55]
Yeah, makes sense. Mike, I heard you mention that you also reframed your ADD as superpower. How did you do that?
Michael Lazerow: [00:34:55 - 00:36:14]
I knew my brain was different. If I'm very interested in something, I go down a rabbit hole. I can't stop thinking about overtakes my life. If I'm not interested in something, I just don't pay attention. And that was my life experience at school where if I was interested in a subject, I did great. If I wasn't, I didn't really pay attention, I would forget stuff. And it became even more disastrous in relationships where, you know, it would manifest itself. And then I was not always present. So I was, I'd be talking to someone, usually Cass, and what she needed, what she was experiencing wasn't necessarily landing. And so as kind of. I was diagnosed shortly after we were married. A lot of things clicked and basically said, oh, yeah, that's how my brain works. And I need to compensate and I need to kind of feed my brain and be proactive and not reactive. And part of the mental health journey for everyone is, I think, understanding how your brain operates. And everyone's different. And, you know, some of the smartest people I know have a very busy and noisy and high powered brain that is hard to deal with.
Anastasia: [00:36:14 - 00:36:15]
Yeah.
Michael Lazerow: [00:36:15 - 00:37:17]
And many of those are entrepreneurs. I also, you know, I spoke about kind of my heart issues earlier, but I also was taught about mental health very early in life. My dad was an entrepreneur and Shortly before my 13th birthday, he, you know, had a complete mental breakdown due to a severe cash crunch in his business. And you know, I was both angry, bitter, and confused as kind of a young kid. But as I kind of have reflected, you know, I learned just this important lesson that, you know, entrepreneurs have mental health challenges that are the combination of a lot of factors that others don't. So when you think of, like, what causes people to really worry, it's money issues, it's relationship issues, and it's health issues.
Anastasia: [00:37:17 - 00:37:18]
Yeah.
Michael Lazerow: [00:37:18 - 00:37:57]
And many entrepreneurs who are facing kind of running out of money, you know, underwater in debt, they start to not only feel the financial pressures, but it seeps into relationships and ultimately their own health, which is what happened to my dad. He bounced back and, you know, was fined and helped others with their mental health struggles. But mental health has been, you know, for at least 30 years of my life, kind of. I've been aware of it in a way that maybe, you know, another generation before me would not have been aware.
Anastasia: [00:37:58 - 00:38:46]
Yeah. There's obviously really scary statistics about the mental health issues among entrepreneurs, and I've tried to find any statistics specifically about people who had successful exits. I couldn't find any. But my own observation in the last 13 years of working and meeting lots of post exit founders is that those rates are even higher. If I just look at my podcast guests, everyone has an issue. There is always something that they had to overcome. So I'm thinking that in overcoming those issues, in understanding ourselves better, we probably actually become better entrepreneurs if it doesn't. If it doesn't kill us, you know?
Michael Lazerow: [00:38:46 - 00:38:50]
Yeah. I mean, you know, as you're talking, I'm thinking about Tony Hsieh.
Anastasia: [00:38:50 - 00:38:51]
Yeah.
Michael Lazerow: [00:38:51 - 00:39:24]
Who, you know, Web 1.0, you know, I got to know. And then, you know, here's a guy who sold Amazon for over a billion dollars. He, you know, revitalized downtown Las Vegas. Very wealthy guy. Last time I was with him, full of life, you know, was at the, you know, Vegas Golden Knights hockey game, which he loved. The Golden Knights. Little did we know, under the surface, for this guy whose mission in life was to create happiness.
Anastasia: [00:39:24 - 00:39:25]
Exactly.
Michael Lazerow: [00:39:25 - 00:40:40]
He was being eaten inside. And I think that we write about this in the book because there are, I don't know the numbers, but a hundred percent of entrepreneurs that I speak to. You know, you speak to entrepreneurs, and it usually goes like this, hey, how's everything going? We're crushing it. Never been better. I'm like, great. Tell me, like, you know, how many employees? Like, I'm like, are there any issues I could help out with? Well, I got this, this, and this. How are you doing? Personally miserable. My husband Hates me. My. You haven't seen my kids. I many days don't want to get out of bed and deal with everything, but I know I have to because people are. And so it's like this, you know, externally crushing it and internally getting crushed, which is typical. And part of writing this book is to tell entrepreneurs that, like, loving to shovel is great and miserable. There's beauty in the suffering, and you're not alone in the misery that you're feeling. And the weight of your situation, which is oftentimes very weighty, let's just say so.
Kass Lazerow: [00:40:40 - 00:41:44]
You know, you often talk about these sacrifices, right? Like you had to crystallize what made you feel fulfilled. I think one of the other ways that entrepreneurs need to think is, yes, there's a massive discipline in the sacrificing and shoveling. I also think the way Mike goes about things is the way to do it is to plan things. You can't do a lot when you're an entrepreneur, but plan things you do look forward to that will allow you to escape the current mindset of an entrepreneur. It's hard to do because I'm very, very disciplined about even kind of rewarding myself. Again, I think this comes back to being an athlete. But when I don't have things to look forward to or breaks, and I mean, that has to be. Breaks away from the kids as well, from it for me, it breaks away from people needing me or asking things of me, then it gets really tough.
Anastasia: [00:41:44 - 00:42:08]
Yeah. Yeah, Cass. I can very much relate to it. And I have to say, to say, at this point, I pretty much gave up on being able to have that discipline, and I delegated it to my husband. I decided that I'll have this external scaffolding for self care. So he's responsible for making sure I take care of myself and he gets in trouble if I don't.
Kass Lazerow: [00:42:09 - 00:42:31]
You know, another thing which has been kind of amazing that I learned this year was at least for operators, because you're always looking at, like, everything that could possibly happen, and you're kind of moving different chess pieces up the board, knowing there's going to be sacrifices. Mike and I got into fly fishing, which is kind of micro focusing.
Anastasia: [00:42:31 - 00:42:31]
Okay.
Kass Lazerow: [00:42:31 - 00:42:49]
And it's allows me like this and, you know, yoga and Pilates, when you have to do something that requires very small movements and full concentration, it's ironic, but it actually relieves you of thinking about 80 things at once.
Anastasia: [00:42:50 - 00:42:50]
Yeah.
Kass Lazerow: [00:42:50 - 00:43:12]
So, you know, people talk about meditation because you're only, you know, doing one thing at a time. That's hard for someone with a busy mind, but doing these micro focusing things, or trying to get your body in different positions while you're doing yoga or Pilates, that will allow your brain to kind of heal, you know, in those moments.
Anastasia: [00:43:12 - 00:43:20]
It's interesting that you're a golfer and lots of golfers say that golf helps, but you're saying for you, fly fishing is better than golf in this sense.
Kass Lazerow: [00:43:20 - 00:44:01]
Well, golf, what I, what I do like about golf. There's lots of things I don't like about golf, including how frustrating it is. But you're outside. I think that's what golfers really benefit from. You know, nature is this incredible therapeutic tool. Right. Because when you connect with nature, even if you're just taking a walk, things that you're thinking about kind of fall to the wayside. So golf is definitely one of those things I think people and definitely Mike, you know, uses as a tool. But for me, it's about only doing one thing at a time, which is not something I do on a daily basis.
Anastasia: [00:44:01 - 00:44:15]
So how do you structure your days at the moment? Like, if you look at your typical day or a week, whichever you prefer, how much time you spend on investing? Entrepreneurship versus family, self care, fly fishing?
Michael Lazerow: [00:44:15 - 00:45:27]
Yeah, we work. Like what we do for living and how we live is we work. So we're friends with people, we work with. The inbound is tremendous. So opportunities, people need help. I would say a third of my time is on that, which includes a lot of it. The, the venture business. Right. And when I say a third of the time, I'm talking about like 20 hours in a day. You know, we, I get six, seven hours of sleep, but it's not uncommon for us to have dinner and then Cass is back at her desk until 9 or 10. If something's going on, we says maybe half the time. We then have our proactive stuff. So we are building. So that's the book. We own a healthcare staffing company. We have stuff that we want to build. So it's not just investments we made, but it's our stuff. And that takes up a portion of time. And any given day, we have close friends, family, kids and each other that need stuff. We try not to. We try to say no a lot.
Anastasia: [00:45:27 - 00:45:28]
Okay.
Michael Lazerow: [00:45:28 - 00:46:29]
We're not. I'm worse at it. Cass is very good at it. And we ask ourselves all the time, if we do this, when we look back on our life, will it be worthwhile? So when we first started thinking about shoveling shit, a love story, is this something that we're going to regret? Or is this something that's going to be additive, that we're going to be like, wow, that was really worthwhile. And although we're spending a lot of time kind of getting the word out and connecting with people, we love it. And we think that it's going to be a. An inflection point that opens up tremendous opportunities that we can't even understand or identify today. And so when we commit to do something, we do it. It's our reputation. It's why we get deal flow. If we don't commit, we don't do it. So if we say no, we say no.
Kass Lazerow: [00:46:29 - 00:46:40]
Don't you also spend. Because I'm actually watching you do this a significant amount of time these days, taking care of yourself. And you do saunas and cold plunges every day.
Michael Lazerow: [00:46:41 - 00:47:18]
Yeah. So I, you know, in my schedule, it's a good point. Like, I worked out at 8am with Rico Wesley, my trainer of over 10 years. Great guy. We have a sauna and a cold plunge on our deck here in New York City. Saunas have the data around. Sauna is, I think, infrared. Infrared, really either one, just heat. It's great for cardiovascular. It's great for mental health. It's great for. For inflammation. And so I've been trying to do it almost every day. And then I have hobbies. Like, I like doing stuff that are creative. I like creating.
Kass Lazerow: [00:47:19 - 00:47:22]
Mike makes bracelets. And, you know, to kind of.
Michael Lazerow: [00:47:22 - 00:47:23]
Do we have to go into this?
Kass Lazerow: [00:47:23 - 00:47:25]
I like the bracelets that you make.
Michael Lazerow: [00:47:25 - 00:47:33]
Here's one of the bracelets. I made two of them, actually. I like making, like, I like making stuff. It relaxes my brain.
Kass Lazerow: [00:47:33 - 00:47:37]
And drawing. You, you often draw, so. Yeah, it's about relaxing the brain.
Anastasia: [00:47:37 - 00:47:38]
Can we talk about that?
Michael Lazerow: [00:47:38 - 00:47:42]
Let's roll this, Cass. Let's not kind of share everything.
Anastasia: [00:47:44 - 00:48:01]
Mike. But I actually do want to talk about your painting career because I know you try to focus on it full time after your exit while you're exploring what else to do in life. So could you share that adventure with us?
Michael Lazerow: [00:48:02 - 00:49:03]
Yeah. So, you know, after I left Salesforce, you know, I really wanted to get back to creating. And I thought that painting was my future. And I really thought that, like, maybe I could be a painter. When you love something, but you're not that great at it, it's called a hobby. And so it's something that, you know, helped me realize that what I do for a living is create businesses. What I do for fun is create art. Go and listen to music. Fly fish with cast. Play Golf, like a few other things. Like, entrepreneurs don't have a ton of hobbies. I think I have more than most and I always have, but I think it's important. Like, I forget who told us this, but imagine you have a plate and only a certain number of things fit on that plate. Be proactive in putting what you want on your plate and everything that's not on your plate, just don't do it.
Anastasia: [00:49:04 - 00:49:05]
Yeah.
Michael Lazerow: [00:49:05 - 00:49:51]
So either do it because it's important to you and it's on your plate, or say no to it because it's not important. And be proactive versus reactive. That's something that comes harder for me, but it's been really important. And so when I say to Cass, listen, you're not going to love this. In January, I'm disappearing for five days to go to Mexico with two of my best friends, one from high school, one from college, to see a bunch of 60 year old dudes play music on the beach. Fish, the band that I've had a relationship with before I had a relationship with Cass. We've been married for 25 years. That's on my plate. But I'm very careful not to do that every weekend. Right?
Anastasia: [00:49:51 - 00:50:12]
Yeah. Mike, how do you figure out what it is you want to do? Because especially for people who go through this transition from their business into the rest of their lives, it's often very hard to figure it out. And I would love Cass to also talk about it. How did you guys figure out what it is you actually wanted?
Michael Lazerow: [00:50:12 - 00:50:22]
So I'll start. But Cass is really, you know, a better answer. I want to do everything and Cass is my filter.
Anastasia: [00:50:22 - 00:50:23]
Okay.
Michael Lazerow: [00:50:23 - 00:50:39]
Literally, we had a meeting yesterday and I'm coming out of it, like, let's do it. Like, I'm not going to say what it is, but it's like any other person would be like, this is an incredible opportunity. And Cass is like, you're fucking idiot. Like, no, like, just sit down, shut up.
Anastasia: [00:50:39 - 00:50:39]
Yeah.
Michael Lazerow: [00:50:40 - 00:51:57]
Like, and so I think, like, you know, the beauty of my relationship with this incredible woman who will not share an office with me is I got all of the credit for our businesses. I was named Ernst and Runk Young Entrepreneur of the Year. I was named Fortune magazine's 40 under 40. Well, Cass is older, so maybe she didn't qualify. You know, I got all of the credit, but we were equal partners. Neither of us would have been able to build any of the businesses alone. And so part of writing the book was exposing Cass's behind the scenes work that has created the life we have today. And I think any entrepreneur who's thinking about a co founder needs to really dial into how do you choose someone who complements your weaknesses and your strengths negate their weaknesses so together you're stronger and you can build a foundation of trust, empathy, compassion, respect, which only happens over time.
Anastasia: [00:51:57 - 00:51:58]
Yeah.
Michael Lazerow: [00:51:58 - 00:52:28]
Like you may be friends with someone, but until you start a company with them and literally get work married to them, you really don't build an enduring relationship. And you know, some relationships are built on interests, hobbies, religions, way of life, our 30 year love affairs based on just the hard work of building companies and families and, you know, homes and memories and yeah, you know, you and a life.
Anastasia: [00:52:28 - 00:52:52]
You did mention that after the sale of Golf.com, you went through a rough patch together. What helped you get out of that? Because again, this is very common after exits. Right. There are so many divorces or difficult years for couples. How did you guys handle it? And other lessons you could share with others who are going through this.
Kass Lazerow: [00:52:52 - 00:55:14]
I think it's cliche, but it really is communication. Mike and I have always talked about like the kitchen table, that's where we bring everything and just sit down and dump and, you know, dump it all. Whether. And it wasn't easy. Right. So there's a lot of miscommunication when you get to that point. But it is about unpacking everything, listening, and then rebuilding. And I think often, you know, you forget the simple. The simple part of what makes relationships grow. And that's communication. Right. And we're so good at knowing each other's lanes that when we're disconnected, it's because we haven't communicated and we haven't shared on a. On a deeper or more meaningful level. We've checked boxes, we've told each other the things we've done, we've shared to do lists. I'm very good at giving Mike to do lists and priorities, but we haven't really talked about the feelings underneath it. And I think that's really how you start to rebuild. And you have to do that because I remember both times after selling the company, Mike being really grumpy. Right. And it wasn't because he had to go work at Time Inc. Or go work at Salesforce. You actually, I think, enjoyed your time at Salesforce and learning there because it was a different. There were different things you were learning. But he was, I think, you know, going through an identity shift. And instead of, you know, I think we could have gotten stuck not talking about his feelings of grumpiness. And what was causing it, and. And those start to pile up, and then you think those feelings are gonna last forever. Right. And both sides say, oh, my God, he's gonna be grumpy forever. Or Mike's thinking, I'm gonna feel like crap forever. You've got to acknowledge the little feelings along the way, the mishaps along the way, so that the intention is there, and then you can move forward. And then the healing. You want to heal the little cracks, right? You think about a foundation. If you have little cracks, you want to put, you know, the glue back in, because otherwise they become big cracks.
Anastasia: [00:55:15 - 00:55:37]
Yeah. So yesterday I interviewed another amazing entrepreneur who created his business with his wife, Adam Rossi, and he said that the venture community really dislikes businesses run by. By couples. And I'd love to share that experience and how you handled that.
Kass Lazerow: [00:55:39 - 00:55:43]
Mike, why don't you tell the story about us trying to raise money for Go?
Michael Lazerow: [00:55:44 - 00:56:37]
Yeah. So, yeah, we've seen everything. We've. We've had investors who absolutely embraced us from day one, and we've had investors who we've made trips to Silicon Valley to pitch them. And literally we walk in and they hadn't paid attention. One in particular, very like, well known firm. And the head person, the person whose name is on the firm basically says after the first slide, wait, you're married? Like, yes. Like, that's same last name. Like, we've set up this meeting. We don't invest in married founders now, mind you, we'd flown from Chicago to Silicon Valley to meet with them.
Anastasia: [00:56:37 - 00:56:38]
Wow.
Michael Lazerow: [00:56:38 - 00:56:51]
And so what I did is I didn't even respond. I closed up the computer. I said, cass, let's go. We didn't say goodbye. We just got up and walked out.
Anastasia: [00:56:51 - 00:56:53]
I'm sure they regret, you know, most, most.
Michael Lazerow: [00:56:53 - 00:56:59]
I think I said, well, I think I said to them, well, we're not changing our status. So thank you.
Kass Lazerow: [00:56:59 - 00:57:58]
That's definitely what you said. You know, I have talked to a lot of up and coming entrepreneurs who are, who are couples and doing this together, and I've always told them that, especially the ones that are in different lanes. Right. I think that's how it has to be for success. You don't want like two product people because I think micromanaging starts to happen. But it is a superpower when you meet a couple who complements each other's strengths, and it becomes a real superpower for investors. And I think all investors should look at it that way because you know that this couple is pot committed. Right. A hundred percent in. And when You. You never have to worry about work ethic. Right. With a couple that complements each other's strengths and weaknesses and are running a company together. So, again, I look at it as a superpower.
Anastasia: [00:57:58 - 00:58:15]
So talking about superpowers, how do you think about your parental strategy in this sense? Would you prefer your kids to be entrepreneurs as well? Do you want them to do whatever they want?
Kass Lazerow: [00:58:16 - 00:59:25]
I. What I always tell them. I mean, they've had these discussions all the time of, like, how did you know you were going to do this? Like, how did you know? For Mike, I think it's a little different for me. You know, I. I had to try a lot of things and cross things off and figure out what I'm really good at. So I would prefer that our three kids spend their twenties really honing what they're good at and identifying their weaknesses and then figuring out how to surround themselves with people who fill in their gaps. Right. And especially with their careers, because I think they have to understand what that's like. And this generation of kids, our kids are in their 20s and our daughter is, you know, almost 18. They've lost that sense of community because of COVID and technology. So in terms of what I want them to be or not be, I think I want them to know and, you know, who they are based on, you know, what their strengths are. I think that's my answer. Mike, what would be your answer?
Michael Lazerow: [00:59:26 - 01:00:49]
I mean, it's really the same. We've lived our life, and it's been a great life. I think we've modeled hard work and ethics that we want them to carry forward. At the end of the day, it's their life, and we want them to be productive and to have purpose and to have impact. However they choose to define that, and there's no pressure, find your path and attack it. And I tell them all the time, part of, you know, college and be an early professional is learning what your superpowers are, and then exploit those superpowers to the benefit of others. And you will receive whatever your goals are. Could be money, could be, you know, doing good. Could be balance, recognition. Could be balance. Could be just a comfortable, just a happy life. And so it's kind of the key is like, understanding yourself, what makes you tick, what you're good at. And then from there, you can figure out how you can be service in service to others, which is really what a company is.
Anastasia: [01:00:49 - 01:00:50]
Yeah.
Michael Lazerow: [01:00:50 - 01:01:15]
You know, you are providing a service or a product, of course, that will benefit others. And if you don't, you die. It's probably not going to be a great company. And if you, if you want to be a change maker, if you want to be a therapist, if you want to be an accountant, if you want to cut hair, all of that is identifying stuff you're good at and literally exploiting it to help others.
Kass Lazerow: [01:01:16 - 01:01:25]
And I would add to that, I often tell our kids, as well as all their friends, you don't have to know what you want to be.
Michael Lazerow: [01:01:25 - 01:01:26]
Now.
Kass Lazerow: [01:01:26 - 01:02:11]
Mike and I are still reinventing ourselves, right? And we plan to continue to do so. And while that may seem scary, you know, again, if you focus back and you go in as opposed to worrying about going outward and you understand who you are and you know your strengths, it's fine to not know what you want to be when you grow up. It's fine to try on 10 different kind of experiences in a career until you settle on what that is. And do I want them to be entrepreneurs? I only want them to be entrepreneurs if, if they want to love to shovel, right? If that's what gives them purpose.
Anastasia: [01:02:11 - 01:02:17]
So how do you approach the whole crazy challenge of raising kids with wealth?
Kass Lazerow: [01:02:17 - 01:03:07]
It's definitely not easy. And it's amplified in New York City. I can tell you that. I think we've done as best as we can do and we could have done, but it's about, you know, unlike most of, I think, our kids, friends who have often, you know, they tell us that they have unlimited budgets and credit cards and things like that, our kids don't. So they, you know, have to live within their means. Obviously when they're with us, they have, you know, nicer experiences, nicer hotel rooms. But we, we've always tried to tell them that this is a, you know, life is, is much better when you learn how to. The things that you have.
Anastasia: [01:03:07 - 01:03:12]
Do you, are you open with them about what the family has financially?
Kass Lazerow: [01:03:12 - 01:03:47]
For the most part, I think, you know, they've read enough, they're old enough to know, but they also, I think, are, you know, have a front row seat to how we decide to spend that money. Right? We're not, we're, we're, you know, I'm a hermit. Like, I, I'm a homebody, right? Like I, I enjoy being home and creating spaces that are cozy and warm and traditions and things like that. So they see how we spend our money on experiences and family, right? We're not extravagant people.
Anastasia: [01:03:47 - 01:04:31]
So I found that there are two schools of thought on this. Some people are saying, including lots of professionals in the space are saying it's Extremely important to start training children on how to manage wealth and prepare them psychologically to having to deal with wealth in the future. While there is another school of thought where many entrepreneurs belong to, which is absolutely not. Kids need to be hungry, they need to experience this hunger and they need to go and earn their own money, even if we know that we are leaving enough for them. So which school you think feel you would you belong to if if either.
Kass Lazerow: [01:04:31 - 01:05:20]
The latter, we want our kids to earn it themselves, even if there's a small parachute at the end that, that we will help them with. I think that people in general who earn their keep and understand again, it's about the struggles, right. And the failures, living with uncertainty, you know, learning kind of financial literacy. Right. I think those are really important skill sets that provide a lot of confidence as you grow and go through changes, especially in life with careers, if you lose jobs, have to find new jobs, you know, when big stressors happen, it's important to know that you can count on yourself and you have those skills. So we, we strongly believe in that.
Anastasia: [01:05:20 - 01:06:11]
So a common argument against this school, which by the way I also belong to, the common argument is that we may be setting up our kids for failure because if they at some point suddenly have to manage money and they don't know how to do it and we supported their entrepreneurial mindset, they may have the problem, which as I'm sure you know, is very common for post exit founders. When it's so hard to switch from entrepreneurial thinking into investors thinking and so many people lose money because entrepreneurial mindset is so different from investors mindset. What would you say about that? Because you did go through this transition yourself successfully.
Michael Lazerow: [01:06:12 - 01:07:06]
I like a lot of stuff. Cass asks the important questions and part of being a good investor is trusting your gut both ways. I can look at any deal and give 100 reasons why it won't work. The question to ask isn't why will it not work? What happens if it does work? So, okay, Uber, it's not going to work because they don't have licenses, they're not able to hire drivers. They're going to be category, categorized as employees. There's no way that you can employ thousands and thousands of people as drivers and manage them well. If they pull it off, they can be one of the largest transportation companies the world has ever seen. Right.
Kass Lazerow: [01:07:06 - 01:07:08]
But I think she was asking more about the kids, right?
Michael Lazerow: [01:07:09 - 01:07:10]
Yeah, basically when I look at the.
Anastasia: [01:07:10 - 01:07:43]
Kids, basically, yeah, the kids and I wanted to transition into talking about entrepreneurial versus investors. Mindset, because I think this argument that people who belong to the other school of thought about kids often make is it's very hard for kids to then suddenly be in a position to have to manage their own personal wealth if we don't prepare and train them to do that, as opposed to being entrepreneurs.
Michael Lazerow: [01:07:43 - 01:08:38]
So everything Cass said about how we approach money and kids, we're on the same page, right? I mean, how could we not be? It's one of the most important things. And we have prepared them. And we've prepared them because we have the head of our state, who's my brother, who's a money manager, who set up the trust, who knows everything about it, who, if God forbid, anything happens, will be there to steward them and teach them. And we have backup plans for that. Right. At the end of the day, it's very hard to teach people concepts, especially your kids who naturally tune you out. Right. At least our kids do. So you can talk, but the only way they're going to learn is through modeling of behavior. How can you model behavior?
Anastasia: [01:08:38 - 01:08:39]
Absolutely.
Michael Lazerow: [01:08:39 - 01:08:56]
And I think we've modeled ethics, we've modeled hard work, and we've modeled practicality in a way that we hope they have a foundation that they'll take forward regardless of our involvement with their life.
Kass Lazerow: [01:08:56 - 01:09:04]
I do agree, and I think they're well prepared while also knowing that their life is going to be about earning it.
Anastasia: [01:09:04 - 01:09:15]
I really want to quickly talk about your book again and what it is. Like, why are you written it? What is it given to you personally?
Kass Lazerow: [01:09:15 - 01:10:14]
At this point in our career, and because we often on a weekly basis talk to entrepreneurs who have questions, need our support, we're often asked like, oh, can you talk to this person? Or you know, I'd really love if you could help out this person. This next 50 years of our life, we really wanted to give back to the entrepreneurial community. And so for us, this book is a chance to provide the 50 plus cheat codes that we've learned over the last 30 years together in hopes that we can be supportive as well as so that entrepreneurs don't feel alone in these struggles. So that was the purpose of this book and to share like the real gritty part of being an entrepreneur, the shoveling part, and why those who actually learn to love to shovel are the unstoppable ones out there. So that's why we wrote this book.
Anastasia: [01:10:14 - 01:10:24]
I love that those who love, who learn to love to shovel shit. Unstoppable. Yeah. I'm so used to, I wouldn't be.
Michael Lazerow: [01:10:25 - 01:11:20]
You know, and as entrepreneurs have to hustle. And so my sales pitch is, go to shovelingshit.com, buy a copy of the book, pre order it. There's $350 worth of benefits, and our benefits are real. So when you start a company, you gotta have budgets, you gotta have planning documents. Like, we've included everything we use to start our companies. You have access to the founders farm. We're doing an event with the community where we get together on Zoom and we shoot the shit. Entrepreneurs helping entrepreneurs. An interview with Seth Meyers where he really goes deep with us about the book, the concepts, among other things. So if you want to join the community, pre order the book. Benefits start right away. And we look forward to meeting all of you virtually or in person at some point, we hope.
Anastasia: [01:11:20 - 01:11:37]
Brilliant. I'll definitely add a link to the interview. I'm so grateful for you. So much wisdom, so much authenticity. Can I ask you just one last question? Because it's the question I ask everyone on this show. How do you want to be remembered?
Kass Lazerow: [01:11:37 - 01:11:44]
I would like to be remembered as someone who gave back more than they received.
Anastasia: [01:11:45 - 01:11:46]
Beautiful.
Michael Lazerow: [01:11:48 - 01:12:24]
And I think I haven't really thought that much about it, but I think at the end of the day, I just want to be remembered as a good guy, someone who did the right thing and that's enough. Like, we don't put our names on buildings. We don't like when we donate. You know, we fund scholarships now at Northwestern in the name of my advisor from college. Like, we don't want to be named. We don't want to be remembered for the stuff and the things. It's just, how do we make people feel when they interact with us, which is really important to us.
Anastasia: [01:12:25 - 01:12:29]
This is so wonderful. Thank you, too, so very much.
Kass Lazerow: [01:12:30 - 01:12:32]
Thank you for having us.
Michael Lazerow: [01:12:32 - 01:12:32]
Thank you.
Anastasia: [01:12:32 - 01:12:33]
Absolutely. Bye.
