How to Win in Business and Marriage (Without Burning It All Down) with Mike & Kass Lazerow

Summary

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The Mello Millionaire with Tommy Mello

Episode: How to Win in Business and Marriage (Without Burning It All Down)
Guest: Mike & Kass Lazerow
Date: January 16, 2026

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Episode Overview

This episode of The Mello Millionaire dives into the art and reality of building both a business and a lasting partnership, with guests Mike and Kass Lazerow—serial entrepreneurs, bestselling authors of Shoveling Shit, and prolific investors. Host Tommy Mello explores topics ranging from surviving the grind of entrepreneurship to balancing success, wealth, and family. The Lazerows, known for selling Buddy Media to Salesforce for nearly $1B and investing in 100+ startups, frankly discuss the sacrifices entrepreneurs make, what really matters in business, and how to keep both marriage and business thriving through hardship.

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Key Discussion Points & Insights

The Real Path of Entrepreneurship: Suffering & Resilience

• Suffering as entrepreneur’s currency:
  • "Pretty much every single day as an entrepreneur are going to be losing days... Too many entrepreneurs give up. It’s the ones that succeed are the ones that can take the suffering, take the punches and stand back up." – Kass Lazerow [00:00, 38:51]
• Passion and addiction to the journey, not just the wins.
• Even with big exits, the pain, struggle, and grind are ever-present.

Building Together: 30 Years as Co-founders and Spouses

• Complementary Strengths:
  • "We don’t have overlapping skills, which is one of the greatest strengths you can have as co-founders." – Kass [03:11]

Moneyballing & Team Dynamics

• Kass excels at “moneyballing”—placing the right people in the right roles [04:11].
• Empathy & Honesty:
  • "We bring a lot of understanding and empathy to entrepreneurs. We’ve seen just about everything... including multiple pivots, going bankrupt. We will steer them correctly, but always honestly." – Kass [09:26]

The Investor’s Perspective: VC vs. Private Equity

• Venture Capital:
  • "Venture capital is about inventing the future… A good 90% plus of VC-backed companies fail to produce outsized returns." – Mike [07:14]
• Private Equity:
  • Seen by the Lazerows as “financial engineering”—more stable, but less thrilling [07:14].
  • Their sweet spot: helping entrepreneurs grow, not just optimizing for returns.

Life after a Big Exit: Identity, Wealth, & Purpose

• Handling Liquidity and Identity Loss:
  • "Founders who sell oftentimes find themselves wanting to give the money back and get their company back. That comes from ego, identity, and purpose." – Mike [10:53]
• “Money lets you buy your time back. Design your calendar before you design your investment portfolio.” – Mike [20:20]
• Advice for new wealth: Don’t rush into big buys; find a great financial advisor [13:11–14:14].
• “There are two ways to be rich. You can have a lot of money or not want a lot. I like doing both.” – Mike [12:43]

Practical Advice Post-Exit:

• Buy time, not toys—no lifestyle inflation [20:20].
• Concentrate before you diversify—focus investments on what you understand [20:20].
• Watch for hubris—don’t assume wealth makes you a genius [20:20].
• Health is wealth—prioritize longevity activities after the grind [22:14].

Knowing Your Strengths—and When to Walk Away

• Not everyone should be an entrepreneur:
  • "You have to moneyball yourself. Figure out what you’re best at. But if you do choose this, you must have the ability to suffer and not give up." – Kass [38:51–40:09]
• The myth of overnight success and dangers of comparison on social media.

Marriage, Family, and the Home “Team”

• Business principles don’t always transfer to parenting.
• "You can’t put your kids on a PIP [performance improvement plan]! And you can’t fire them." – Kass [28:00]
• Presence and modeling healthy relationship dynamics for kids, especially between ages 2–7 [28:55].

Deal-Making & Leading with Values

• The Lazerows choose not to over-leverage deals:
  "We’re not optimizing for every last dollar. We will give up some money to sleep at night and not live on the edge." – Mike [25:47]
• Buy businesses and keep founders:
  • "When we buy a company, we’re not buying 100%... We love the founder so much, we want her to be a billionaire too as we build the business with her." – Mike [23:17]

Emotional Intelligence, AI, and the Future

• Emotional intelligence (EQ) can be taught but is partly innate [36:14].
• “In a world where instant gratification isn’t soon enough, skills like listening, empathy, and selling are more vital than ever.” – Mike [35:53]
• "There are two types of businesses: those that adopt AI and those that are out of business." – Mike (paraphrasing Mark Cuban) [33:53]

Quickfire & Closing Questions

Best Advice They Wish They Knew in Their 20s:

• "You can do anything, you can’t do everything. Focus, focus, focus." – Mike [29:25]
• "My 80% is probably better than most people’s 150%. I didn’t realize that back then." – Kass [30:10]

Where Would You Invest $10 Million?

• Equal parts in “boring” returns, venture, kids/experiences, and homes/community [30:53].

Professional Dream?

• Build a $1M/year paid speaking business, keep time for longevity and freedom [32:30].

Book Recommendations:

• Man’s Search for Meaning by Viktor Frankl ("If you find purpose, you get through any misery." – Mike [41:06])
• Outlive by Peter Attia (on health/longevity) [44:03]

Final Words of Wisdom:

• “Do the right thing. Usually costs you something, but it pays off.” – Mike [44:08]
• "Watch out for your health—don’t let business cost you years of your life." – Kass [43:14]

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Notable Quotes & Memorable Moments

• "Entrepreneurs love to suffer—it’s our currency." – Mike [01:09]
• "When you start a company, you’re giving people a front row seat to your failure." – Mike [00:54]
• "You buy time, not toys." – Mike [20:20]
• "There are two ways to be rich. You could have a lot of money or not want a lot. I like both." – Mike [12:43]
• "We thought we could bring home what worked at the company back to our team at home. Home teams don’t work like that… you wish you could put them on a PIP, but you can’t!" – Kass [28:00]
• "Just ask yourself, what’s the right thing to do? It usually costs you something." – Mike [44:08]

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Timestamps: Key Segments

• Suffering in Entrepreneurship: [00:00–01:09], [38:51–40:09]
• Defining Roles in Marriage & Co-Founding: [03:09–04:02]
• Post-Exit Identity & Strategy: [10:53–15:49], [18:42–22:37]
• Venture vs Private Equity Explained: [07:14–09:08]
• Advice to New Founders/Post-Liquidity: [20:20–22:37]
• Emotional Intelligence, AI & The Future: [33:53–37:40]
• Key Life/Business Advice Quickfire: [29:23–32:30]
• Book Recommendations: [41:06, 44:03]
• Final Words: [43:14–45:05]

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Tone & Takeaways

Candid, self-deprecating, and deeply authentic, Mike and Kass bring wisdom forged in trenches—not just boardrooms. Key takeaways: The entrepreneurial path is brutal, but meaning is found in the struggle. Money’s true value is in what it frees you to do, not buy. Focus, empathy, and health are as critical as hustle. And, perhaps most important: do the right thing, even when it’s hard.

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For listeners seeking both business breakthroughs and life lessons, this episode offers a masterclass in ambition, resilience, and building what matters—together.

Transcript

[A]

The one thing that you have to have, the one trait that you better have as an entrepreneur if you decide to do this, is the ability to suffer. Because pretty much every single day as an entrepreneur are going to be losing days. Days that something hasn't clicked and too many entrepreneurs give up. It's the ones that succeed are the ones that can take the suffering, take the punches and stand back up.

[B]

Successful, renowned worldwide, Cass and Mike Lazaro are award winning entrepreneurs, best selling authors and visionary early stage investors.

[C]

The more you de risk, the easier it will be for investors to say yes.

[B]

As co founders of Golf.com and Buddy Media, their company was acquired by Salesforce for $745 million. These days as investors, they've backed more than 100 startups including Scopely and Liquid Death.

[C]

When you start a company, you're basically announcing it to the world and giving people a front row seat to your failure.

[B]

They've helped generate over $10 billion in realized returns. Their best selling book, Shoveling Shit reveals the real and messy path behind their success.

[A]

The takeaway is that entrepreneurs love to suffer and it's kind of our currency and any successful entrepreneur has to learn to love to shovel.

[B]

Today the two of them run a portfolio of businesses, advise founders worldwide and split time between NYC and the Hudson Valley with their three kids. All right guys, welcome back to the Mellow Millionaire. Today I got Mike and Cass Lazero with me. They're award winning entrepreneurs, bestselling authors and visionary early stage investors. They are widely recognized for building and scaling cat defining companies. Today they run a portfolio of businesses, advise founders worldwide and split time between New York and Hudson Valley with their three kids. Thank you guys very much for doing this. I'm excited.

[A]

Thanks for having us.

[C]

Thank you. We appreciate it.

[B]

So I, I guess let's just talk about what was the pivotal moments that you guys really enjoyed. What are you excited about today and where are you headed? And I don't know who to choose here. So we're whoever wants to take the questions.

[A]

Mike, you start.

[C]

Yeah. So we've been entrepreneurs our whole life. So I went to journalism school at a time when journalism was falling apart as an industry and as something that people actually wanted to do. And the Internet, started the commercial Internet while I was at Northwestern in journalism school and I just went down a rabbit hole and I never came out of the rabbit hole. So it started with my first company at Northwestern called University Wire which merged with a company called Student Advantage, went public, we then kept going. Cast started Golf.com while I was doing that, and then she had an unfair recruiting advantage and got me over to help her build that. Sold that to Time Warner after some ups and downs for 25 million. And then what we're best known for is Buddy Media, the leader in social media marketing software, which we sold to Salesforce for close to a billion dollars.

[B]

I love Cas. What do you think?

[A]

I mean, Mike said it pretty well. We've been serial entrepreneurs for the last 30 years and we've worked together for all of those, which to most people seems like a surprising fact. But we don't know any better and it's worked perfectly. We don't have overlapping skills, which is one of the greatest strengths you can have as co founders. So here we are, you know, 30 years later. We wrote a book that's called Shoveling A Love Story about the entrepreneur's messy path to success. It's our kind of nod and love story about each other, but also the love of being an entrepreneur and sharing that validation with all the other entrepreneurs out there that we see them, we know the shit shoveling that they have to do, and we are here for them.

[B]

What would you say, what do you Enjoy the most, Cas, what's your passions in business? Where do you get excited to go into a business and help out?

[A]

I definitely, you know, as investors now, I would say the thing I'm most, most excited about is helping the founders and teams form. I'm very good at what I call moneyballing, so I like to put the right people in the right spots to get over the plate. And that's the strength that I bring. And it's also what I love doing.

[C]

I love it.

[B]

Mike, what about you?

[C]

Yeah, so we love entrepreneurs. I mean, people ask us all the time, why'd we do 100 deals ourselves off our own balance sheet? Why'd we start a venture capital fund? Why are we buying businesses right now? It's because we're addicted to entrepreneurs and entrepreneurship. And although the book's called Shoveling Shit, it's a love story. It's the great entrepreneurs. I mean, just look at you, Tommy. Like, you've built a business and, you know, you have a great life right now, but I can't imagine what it took to build, you know, that monster business where you're going like door to door, like, getting customers on board. And so we think that it's both miserable being an entrepreneur and the best way to spend your time. You both suffer and it creates a lot of pain, but the pleasure it brings in personal relationships and security eventually. And just kind of being able to get out of bed and have a purpose in the morning has been the biggest gift. And so we, we know what we do. Like we're not the smartest people in the room. We're not, you know, our gift is in identifying people, identifying opportunities, which we did with the Internet and web 2.0 and AI and water. When I first met Mike Cesario, he had this crazy idea that I want to market a water product, a health product. Like everything that's bad for you. I want to be an entertainment company that happens to sell water. And it was such a crazy idea that we're like, yeah, we're in before he even sold one can of water. And so this is something that we, it's our identity, it's our relationship, our love story. And why we're so thankful to be here is your effort in supporting real entrepreneurs. When I say real entrepreneurs, these aren't venture capital backed businesses. We wrote the book for people who don't have a safety net, People who are building businesses for future generations without the crutch of venture capital. Those are the real entrepreneurs.

[B]

Yeah, you know, venture capital. If you had to explain to me, and I'm just, this is for the audience. I, I, I've met a lot of venture capitalists. It seems like Jeff Bezos said it, the best in baseball, the best you could get is four runs. And when you're a VC, you could get a 10,000 runs. But, but then there's private equity. And private equity is swooping into all of home service, home improvement, and a lot of other industries. What do you think the biggest difference is between private equity versus venture capitalism?

[C]

Yeah. So venture capital is about inventing the future. It's about how do you get to the future faster. And typically whoever gets to that future faster as a business sees outsized rewards. Having said that, it takes a lot of capital, venture capital backed businesses, and most of them fail, most of them don't work out. And not just a majority, but if you look at the numbers, a good 90% plus of venture capital backed companies fail to produce that outsize return. And it takes a different mentality to go from 0 to 1. So to go from an idea that has never exists, whether it's kind of ride sharing, cars that fly, any of these crazy crypto ideas, it's just a different mentality than how do you scale something that exists? And we do both. So we both invest in the future and we're buying businesses that are just great Businesses like executive search firms and healthcare companies and firms that basically provide a great service to a customer like you do and build on the back of word of mouth, which is the ultimate marketing. And so private equity has basically said that, listen, these are great businesses, the home service business. They're not going to be crushed by AI. Everyone's going to need these services as they are with dental practices and all these other businesses that are getting rolled up. And because the cash flow, they're able to leverage their acquisitions, use equity and debt. To me, that's more of a financial engineering. It's not as exciting to us. We love inventing the future. But what we like about buying businesses is working with entrepreneurs who've never had an operating partner who can tap into our network, into our playbooks, to start growing again, which is exciting.

[B]

Cas, what do you think? You guys obviously probably have people, whether It's. There's probably 10 people for different types of marketing. You got the right CFO background, you got the right FP and A teams, you got the right executive searches. What do you think you guys are known to bring to the table?

[A]

So I think Mike and I fulfill to most companies help with networking, sales, fundraising, marketing operations, team building, hiring, retaining, you know, their employees. So they kind of look at us for different things. Mike and I, like I said, we, we divide our talents, which is great. And I think they know that because we've been in the trenches, we've seen just about everything when it comes to any kind of a company, including multiple pivots going bankrupt, you name it, we will steer them correctly, but also honestly. And we're going to understand when they vent about something, we get it. We absolutely get it. Because, you know, being an entrepreneur is 24 7. So I think we also bring a lot of understanding and empathy to entrepreneurs.

[B]

You know, I want to ask some selfish questions here and I think the audience will get a lot out of it because Gina Wickman and I had a long conversation about it of you build this business, sometimes it's your DNA, it's your identity, and the money comes. And I think a lot of people just don't know what to do when they have that first exit. You know, I rolled half back into the business and I still feel like it's my DNA. I really do. I'd love to say, oh, no, I'm not attached to this business at all, but I am. But what is, what is your take on that? Either one of you could answer this.

[C]

Founders who sell oftentimes find themselves wanting to give the money back and get their company back. And that comes from kind of ego and identity and purpose and purpose. And so they find themselves with a lot of cash, but not a lot to do. In the morning, I was, we were just at an event in LA and a founder had sold his business for 3 billion. Said I'd give the money back right now to get my business back. And I think what we've learned is that money is great, but it doesn't really change who you are. What it does is it lets you make decisions to buy your time back, which is what you're talking about. And so how can we have a venture capital firm and a private equity firm and write a book? We have incredible people. We have incredible people who, a lot of them who've worked with Cas Forever as operators. And we're able to buy our time back. We don't have to do everything. And we protect our time, we protect our energy. Like it's capital, right? And that includes sleep. People are like, you guys must not sleep. It's like, no. Cass knows at 10 o', clock, I'm gone. I'm asleep. When I get up, I'm up. Like, I don't stay in bed. It means resting, it means working out. And if you are a founder who finds yourself in money with money. A few things that I would do. One is don't buy anything for a year. If it dries, flies, you know, just don't do it. These boats are like. We owned a boat once. We, we bought a house in Turks and Caicos and it came with a boat. And it was like the only thing we thought about. It was like the bane of our existence. So rent a boat, rent a captain. That's fine, right? But just like, you know, make things easy. There are two ways to be rich. You could have a lot of money or you could not want a lot. I like doing both. I like having a lot of money and not having a lot that I want. Right. Especially like physical things. Number two is find someone who's really good at money management. I'm not talking about stock picking. I'm talking about trust. I'm talking about tax strategies, which is ironic. I'm sitting in New York City, which.

[A]

Is the worst place, and making sure you protect your estate. Right?

[C]

Yeah. And a lot of us, just because we have success in business doesn't mean we're good at managing our own money. Just realize that. Realize that you are good at doing your business. You do not have the experience of managing hundreds of Millions of dollars. And so once you kind of realize that they're experts, you shouldn't be kind of paying all your bills. You shouldn't be worrying about the day to day. You should be thinking about what are your strengths? How can you exploit those strengths for the benefit of the world, both through business and through, for the first time, if you're just making money? Philanthropy.

[B]

I agree. I mean, look, the right person, the tax strategy, the trust, there's, there's so much. If you got a lump sum of money, it could be 10 million, 100 million or a billion. But do you believe like the, oh shit, money should just be like, this is going to continue to make money. This is like, this is our safe. Or do you just say, let's, let's bet it all and diversify it in more ways to grow it.

[A]

I, I can tell you that over the past, let's call it 15 years, we have struggled to, to stop investing in venture, right? Because we love entrepreneurs, right? So we have done a better job at having the boring return, right? And, and literally when you make chunks, putting it aside and just letting it grow, don't worry about, you know, the next investment and things like that. But you do have to think about it, just like you said, which is if you, if you make a million bucks, what are you going to do with it, right? And you should be thoughtful about it and you should have someone who can advise you so that you do have boring and you do have the stuff that you love to invest in so you're not, you know, missing those opportunities. And then, you know, you have to use some of it for whatever that is. We happen to have three kids, so they got a lot of that money spent on them. In terms of education.

[B]

With VCs. Explain to me because I'm not very familiar. I've never been down the VC path. I was at a Goldman event. There was 80 founders. I was very fortunate enough. I was like the most boring guy. I'm like, I do garage doors. There's all these software guys solving like sickness and genetic mutation. And I was like, yeah, I do. I make the doors go up and down. But where do you go? How did the deal flow come in? Like, what do you look at? Do you have a whole team that does diligence? Are you guys out there meeting people every day? We what's good, what's bad? What gets you excited? I mean, this is a loaded question. But I just, I don't know much about it.

[C]

So it's a good thing you don't know much about venture capital. I mean, it's really a. It's not even an industry. It's has been perverted in this world of like, you know, Facebook and Uber and everyone wants to do be an angel investor. And at the core what it is is basically taking money from very large individuals and institutions and say they have a 2% allocation to venture capital, which is like this innovation economy. You raise money from those what are called LPs that you then are investing in companies. Now, for us as entrepreneurs, we just happened to hang out with a lot of entrepreneurs as entrepreneurs who returned several funds for our investors. Meaning like they invested in our company that returned all of the capital for the entire fund. That makes a lot of friends, right? Like you have people who are, who like you. And so our deal flow comes from these friends who over the years, like any industry, it's a very small industry. So when Peter Pham in la, who has a firm called Science, calls up about this crazy idea of liquid death. Do you want to meet Mike? Yes. When I get a call from Howard Lindsin saying, do you want to meet Walter Driver who started a company called Scopely which sold for 5 billion in cash? Yes. And so all of us have our industries, we all have our network. And what I would tell everyone is that more than money, your network is your net worth. Ours happens to be in venture capital, but it's not like anyone can get into venture capital. If you're not in venture capital, the jobs don't exist. Cass, you would you agree with that or no?

[A]

Yeah, I do agree with that. Well said.

[B]

Yeah, that's interesting. I mean, I know of a lot of funds. I'm good buddies with the, the guys that founded Service Titan and they, I think at Bessemer as early investors.

[C]

And yeah, it was Byron. Dieter, I know.

[B]

Well, yeah, Byron, I met him the other day at a football game. He's a real great guy. And then they invite, you know, some they talked about Fusion. They were like, yeah, we're, we're a couple of years out from Fusion. There's about 10 companies we're investing big. And then they said, might sound unorthodox, but we invested in the 49ers because we think people are going to want in this AI driven world to come together.

[A]

Entertainment. Yeah, Community.

[B]

And so I love learning about this stuff. And you know, I'm thinking like, you could buy gold or you could buy bitcoin and you could buy real estate and get accelerated depreciation or do a cost segregation study. There's like, a million ways to put money in. I mean, what would you say to somebody that just had a really good exit? I mean, but you still want to have purpose. I think you guys nailed it. Like, you don't just want to sit around and just watch this, you know, S&P 500 all day.

[A]

I think. I think the first thing, since we do have some experience with this, is that you let yourself sit in the uncomfortable quiet for six months. And I say that because you want to do this. Like, what's the next best thing? You know, I got to get in it again. You're like. It's like an addiction almost. These entrepreneurs like to keep going, and first you got to reset your whole, like, nervous system, because what you do, and you know this from being such a successful entrepreneur, it's a lot, right? Especially when you're. When you're pushing and running really fast. And you know, what we tell entrepreneurs is you've got to figure out if you want to, your next best idea. But also that might come from just sitting in the quiet, doing a lot of reading, consuming information that's out there, learning, educating yourself. Because what happens is when you're in an industry like, you know, we were in software, you're going to know everything about that, and then something else is going to come by, and you have to adapt. And a lot of times, the best founders can't adapt because they're running out of time, and they just don't have that focus. So my. My goal to every founder when they do this is to hire a team, an accountant, a tax attorney, an estate attorney, someone who can talk to them about what money is in the estate and outside the estate, especially if you have kids. Think about education and take a breather. I know it's hard, but you got to take a breather.

[C]

There's basically like, yeah, I was just talking to a founder about this, and I just gave three pieces of advice. Number one is buy time, not toys. So no lifestyle inflation. And the idea was that before you even think about your investment portfolio, design your calendar. Like, design what you want your life, be proactive, because too much of our day is reactive. And so if you say, this is what I'm doing, this is what I'm not doing, you know, it could be anything from, you may want to play golf once a week for the first time in your life. You may not want to. You may want to volunteer, you may want to kind of sit on boards, but just design it. Number two is concentrate before you diversify so feel, think about, like, okay, if that's your calendar, don't worry about spray and pray investing. You could hire someone to do that. But what are the areas that you deeply understand and what are the areas that you want to concentrate on? And it could be starting a company, could be investing, and try to stick. Number three, there's hubris that comes with selling a business. The way you're treated when you make hundreds of millions of dollars is just different. Like, people think you're smarter. People think you're not the schmuck you were three minutes ago. Right. And so try to invest kind of where you can add judgment, not just money, because capital's everywhere. And kind of those three things, I think, have really helped us. And the goal isn't. You know, your goal after you sell is, as I'm thinking about it, isn't to get rich anymore. Right. It's not to, like, make another hundred million. It's to stay free. It's to stay unencumbered from all of the bullshit.

[A]

I would add one more, too, Mike, that we forgot. Health number four. Health. What's up? Exactly. So you have to focus on being healthy. And I haven't seen a lot of great entrepreneurs do that from the start, but I can tell you that they start doing it after an exit. And so that should definitely be on your calendar.

[B]

You know what's interesting? I was at a private equity event, and I got to speak. I was the only founder there speaking. Then I asked the guys in my, you know, Cortech, which is our P fund, I go, what am I going to do up there? I go, just go up there and be. You tell stories like you always do. And luckily, I got a standing ovation.

[C]

I.

[B]

At the end of it, I was like, guys, if you could do anything, your LP's in this fund. It's time to buy a new garage door. And I told a lot of stories about my family, my mom.

[C]

So good.

[B]

So what do you guys feel? Especially if it's a platform, what is the process or the thought process of not having the founder's role?

[C]

Yeah. So we're big believers in founders staying, and as are the people we're closest with. Marc Benioff, when he bought Buddy Media, it wasn't just about buying this company. It was about helping to build a whole new part of Salesforce, which was the marketing cloud. Right. I remember him saying that, listen, if we cut open our arms, we're the same. Right. Our blood is entrepreneurial. I don't know how to keep you Guys here, but I'm going to take the 30% that were paying in stock and re vested over four years. And he was already paying a lot for the money, kind of overpaying for the business. So I was like, okay, great. And Cass said, okay, when we buy a company, we are not buying a hundred percent of it. One deal that we're doing right now will own 50% of it. 51% of it. We love the founder so much. She is so awesome. We want her to be a billionaire as we build the business with her and she's fired up and she's young and she's just, you know, she's in the medical space. Just great at what she does. Same thing. We bought the executive search firm and other companies. They own anywhere between 25 and 50%. And most of the entrepreneurs we speak to work with us at least and I think work with other private equity for two reasons. One is they have no one else to work with. Like they just get a bunch of money, but that's very rare. The other is they haven't had any operating help. And so we bring in a whole playbook and a team to do all the business operations. If you talk to an entrepreneur, what do you love doing and what do you hate doing? They know it right away. They're like, I love this. I love being with customers. It's like the thrill of victory where we land the customer and delivering for them. What do you not like? Oh, the payroll and all the bullshit around people who. It's like babysitting. And you're like, okay, well, let's go.

[B]

I love that you guys identify those things because I look at the way the company's grown in the last three years and I'm not a big fan of pivot table or payroll or dealing with HR or dealing with lawyers. And so I've got such an amazing team that they do everything I don't like. So I get to love what I do. I come in and I don't do anything I don't want to do. I do the orientations, I run some of the bigger sales meetings. I'm on every marketing call. And that's what, that's where I jam out. I love recruiting people. How much debt do you guys typically use in a deal? I mean, do you use like maximum leverage if you can get 5 or 6x?

[C]

So we use 0 right now because we're equity people. And that's going to sound crazy, but we basically started the firm with our own capital to buy companies. And my dad Went bankrupt as a real estate developer because of debt and we've never really played in the debt markets. Having said that, that's going to change in 2026. I've seen the light. I've been read the riot act by many of my very smart investors and private equity people. We're not going to over leverage the business, but if we are going to start bringing on debt, probably no more than 50% so we have a debt coverage that we can live with. And we're also different than private equity firms. And I share this because all of your entrepreneurs who are listening are the same way. We're not optimizing for every last dollar. We're not financial engineers. We will give up some money to be able to sleep at night and not living on the edge. I have a friend in the storage business and they had short term self storage. They had short term debt on a lot of properties and as the interest rates went from 0 to 7%, they just got crushed. Like that is what would stress me out. Customers leaving, dealing with employment issues, even getting sued, which we've never really done those you just deal with. But existential issues is what you have to look out for and debt is one of them.

[B]

A lot of people get burned out. My first exit, I lost a lot of my. I had lop show. Like it was stressful. I had no idea. I was like sitting in a room and I'm like, I'm biting my nails and I'm like oh, like what is, what's going on? Like another dinner and we got to do this dog and pony show and like literally like we're a great company and I'm like. And then we set up all this stuff and they told us how to act and what to do and when to grab our forks. It was a little bit over the top and we're lucky. We got the right partner and we got a great return for them. And you know, I want to do it again and. But I do want to have kids. I'm just going to be an old ass dad and I've heard the days are long but the years are short. So I'm looking forward to it.

[A]

That is exactly correct. With kids, if you want kids, just pull the trigger. Because like you said, you know, I think it's a young person's game. So you want to make sure that, you know, you're moving that. I mean like Mike and I always talk about longevity because I want to be the grandmom that's out there still throwing the football with My grandkids and everything. And also just remember, like, and I think Mike and I learned this lesson. We thought we could bring home the things that work very well in a company back to our team at home. Our home team doesn't work like that. First of all, you, you know, you, the kids, they are who they are when they're born. It's not a lot of, you know, nurture that changes them. Second, you can't put them on a pip. I wish I could put them on a performance improvement plan. It doesn't work and you can't fire them.

[B]

100. I think I've read a lot on this and I'm not going to get everything from a book. I know that. But, you know, the first couple years they're kind of like learning their foods and stuff. But years like 2 to 7 is when they're like, if they don't see the parents getting along, I think that's a really big deal. I'm going to ask you guys three repeat questions I ask in every single one of these podcasts. What's one piece of game changing advice you wish you knew in your 20s?

[A]

Mike, you can start.

[C]

I mean, my biggest one is focus. I wasn't very focused. And what I've learned is that you can do anything, you can't do everything. And so no matter what age you are, and it's more important if you don't have any money and you can't buy back your time. Focus, focus, focus. What are your goals for the year? For the next six months? What are the three things you need to do to reach those goals? A lot of what we did, we just did without much thought. Like, we're going to launch Golf.com, we're going to launch a software company. But hyper focus, and that was the. I think as I talked to people who wrote our book, who read our book, that is something that really resonates because entrepreneurs see a shiny object, they're like, I got to do that and that's bad.

[A]

Mine would be that my 80% as an entrepreneur is probably better than most people's 150%. So I think in my 20s, I said, if I do all of my effort over here, it means everything else is at zero, where it's not at zero. So if I'm all in with Buddy Media, when we were, I was thinking, my kids are getting zero, they weren't getting zero. They were probably just getting 80%. And that still counted, you know, a ton.

[B]

That's great advice. If you had to Start over. You get $10 million. Where's the $10 million going?

[A]

I think 25% is going into our boring 7 to 10% return. I think 25% is going into venture, and I think probably 25% is going into the kids we have and probably like experiences, I think, because that's how we'll build memories with our kids later on. And I think the rest would be the homes that we build so that we had places to build in community and have our friends and family there.

[C]

With 10 million bucks. Like, how are you going to build homes and live?

[A]

I don't know where. I'm just giving you the.

[C]

I'm glad. I'm glad we're already rich because we would not agree on that.

[A]

Well, I'm thinking, I'm thinking about like, okay, we're going to need part of it to live.

[B]

We'll get deeper here, Mike. But where do you guys. Where's the main home?

[A]

New York City. And then we have a house upstate. Yeah.

[C]

So we have a place in Hudson Valley, which we love. And then we're now empty nesters. So we if. When we're invited places, we show up. So people just need to invite us. And we love nice places. Having said that, it's where our businesses are, where we live. We love New York City, but we love leaving New York City. It makes no sense as a tax location for us, like living in New York City. Sometimes it feels like no one has enough money. So people are worth a billion dollars, Are feeling like they're worth 10 billion.

[B]

What's your biggest professional dream at the moment?

[C]

Because we hit the New York Times list and people seem to like us speaking. We have a, like, paid speaking business, which is kind of so weird to us after all these years. And so our next goal with that is to do a million bucks a year in speaking, which I have no doubt we like we'll be able to do. People said we couldn't be New York Times bestsellers with a title called Shoveling Shit. And we said, okay, that's like catnip for us. We'll just work our ass off and make it happen.

[A]

I think he's right on that. I think speaking is good. I also want to continue to have enough time. Like Mike talked about freedom to think and participate in longevity activities.

[B]

All right. You know, I wanted to just touch upon something because I'm cautiously optimistic. And I've been reading a lot about AI and really studying people that know a lot more than I do. And unlike the Industrial Revolution, it's not like you're just going to go learn something else. Like when that came out, it was muscle. Instead of 50 farmers, now you needed 10 to run the machines. And I just worry because Ara, the founder R and Bahi are in his office and he just kind of said, I feel bad for my kids because we got to come from nothing. And slowly but surely, I mean, robots are coming out next year. I don't know, I don't know where we're going. What is, what is your take on that?

[C]

I mean, so I do believe in like what Mark Cuban has been saying lately, where there are two types of businesses are ones that adopt AI and then they're ones that are out of business. What's interesting about where we sit is we sit in two distinct but powerful areas. One is we're funding a lot of AI products and services. And so we're part of a group that funded a company called Etch AI, which is making chips that are 10 times faster than Nvidia at half the price with a quarter of the energy. Very fast growth company powering a lot of the services that on the flip side, the companies we're buying are using. So think of executive search and, you know, longevity. A lot of these services instead of doing like a lot of it's just like brute force. You have to call people, you have to do outreach, you have to do sales. We're basically building stuff. That's who are the top five people that we should speak to about this C level job at this company, right? So all of a sudden the outbound takes a minute and you're identifying candidates and then it's just a sales exercise which we love. We train our people to be great salespeople because you gotta, you know, everyone who we wanna recruit has a job they like. I'm happy, I'm not moving. You talk to them, Whoa, this is interesting. And you have to get them to say yes, right? At some point. And so I think what I've told my kids is learn how to sell, learn how to communicate, learn how to listen. Just harder for dudes. We just don't listen very well. I mean, listen not just hear what he or she's saying, but sit in their shoes. And those are the skills that I think will be rare in a world that we're glued to our phone and people don't have any attention because instant gratification isn't soon enough.

[B]

Is emotional intelligence learned? Or because we could talk about nature versus nurture. But my grandparents told me I was their favorite because they listened to their same stories over and over, and I was genuinely happy to do it. And I'm not saying I have the top emotional intelligence, but I think my EQ is probably higher than my iq.

[A]

I think that you can, to a point, teacher eq. Right. Emotional intelligence, I think, to a point. But I do think there are some people who are born probably you, probably me, with much higher EQs than IQs. Right. And it's just our sweet spot of really understanding people, being able to sit in their shoes, understanding, listening, making people feel heard, things like that. But I do think you can teach them. I mean, we used to. I used to run a ton of different meetings in all of our companies based on eq, because it's how you actually run a team. You have to have that. You have to be able to pick your head up and not just look at numbers. You have to be able to understand how to put people in the right position, what to count on them for, and then how to actually pep them up so that they do what you need them to do. And that's emotional intelligence.

[C]

And look at. Look at me, Beth. Like, I'm the worst. Like, I had no EQ and it was, like, beaten into me. Like, it's not about, as I think about it, it's not about empathy. It's about, like, regulate yourself. Like, sit down, shut up, listen. And that's what I'm seeing is missing across the board from employees, from kids, from adults. It's like, just pause before you react. Like, think about what you're feeling, what you're contributing.

[B]

You know, there's this. There's this book that. It's called Driven, and it's. There's really only about 6% of people that have this. It's actually genes. It's like our chromosomes, and we're hunters. And there's a lot of farmers out there. Hunters need farmers. Farmers don't necessarily have to have these hunters, but a lot of people all over the Internet, especially in the United States of America, everyone's saying, you need to be an entrepreneur. You need to be an entrepreneur. You need to be an entrepreneur. And I'm thinking about the times where, like, I couldn't make payroll and I had to go on a fight or flight. And that's when I do my best. I don't give up. I didn't quit. And, you know, I had to learn how to focus, and I had to borrow against my mortgage, and I. I mean, I put the chips back in 10 times and I keep doing it. And I don't really think that advice is very good for most people. I think they could be entrepreneurs. I think they can make a lot of money, they can still have equity in the company. But now everybody's like, I want to be an entrepreneur. I want that dream. And they see these Instagram posts or TikTok or whatever and they see all the good stuff. They don't see what comes with it. And I said, I'm an overnight success of two decades is what I tell people. What is your guys take on that 100%, right?

[A]

I mean, first of all, you know, social media is like the worst thing that's ever been invented. It's great for marketing, but it's horrible for everyone's mental health. And the comparison problem that everyone has is they think, like you said, that you are an overnight success. We're overnight success story of 30 years, right? So it's, I don't think everyone should be an entrepreneur. I think you've got a moneyball yourself. I think you've got to figure out what you're best at. But the one thing that you, you have to have, the one trait that you better have as an entrepreneur if you decide to do this, is the ability to suffer and like you said, not give up. Because pretty much every single day as an entrepreneur are going to be losing days. Days that you something hasn't clicked, you messed up, you have many failures. And if you keep going, you said this in the very beginning. Too many entrepreneurs give up, right? It's the ones that succeed are the ones that can take the suffering, take the punches and stand back up. So your advice is correct. That advice is not great for everybody, but I think it is the right advice for the right entrepreneur. It's just not everybody should be an entrepreneur.

[B]

My experience, I always get so pissed when my dad would say, if I knew then what I knew. Now I'm like, so tell me. And what I realized, what every one of my uncles and dad was saying was, don't care what other people think. Go for no. You only worry about you don't fear rejection. And these are life lessons though. The deal is you got to experience them. You can't tell somebody these things. Hey, I want to ask you guys a couple closing questions. If I had an extra hour, I want to do a 2.0 of this and I definitely am going to invite you guys out. So you got an invitation coming. I want to get to know you guys.

[A]

I would love to.

[B]

And we got to pick up shoveling everyone that's Listening to this New York bestseller, and I've got a million questions I didn't even get to. So is there anything, any books that you feel like are a must read other than shoveling shit that will change people's lives?

[C]

You said, my favorite book in the world, which is Man's Search for Meaning. Victor Frankl. Victor, if you have not read that book, you are doing yourself a disservice. And I think shows that kind of finding your purpose, whatever it is, can get you through whatever misery your life is. And I'm not a listen, the backdrop was a holocaust. It's not a very pleasant thing, but if you can find purpose in the midst of that backdrop, anything you're working on as an entrepreneur just gets easier. And so, both personally and professionally, that's the book. And when you mentioned it, I kind of got a little tingly because it's like when I say we're cut from the same cloth, there's a lot of this stuff that we believe, and then there's a lot of tactical things. Most of that stuff was written by stuff that have never done anything. And so if someone's trying to sell you ideas, why I was so excited about coming onto this podcast is that there's so many people who are trying to do what you're doing who've done nothing. We did so many as part of the book, like, earlier in the year, and there are only a few who actually have built real businesses. And you could name them probably on both hands. Right. And so we just appreciate the time that you've given us and hopefully. First of many conversations.

[B]

Yeah. I've got a lot to learn from you guys. And one thing I, I tell everybody. I mean, literally the best advice I could give anybody is success leaves clues. Just go ask.

[A]

Well, it's also like, who do you surround yourself with? Right? You want to surround yourself with the people that you aspire to be a hundred percent.

[B]

And I want to give you both 30 seconds to close us out, because this has been an amazing. I've got so much to learn. I've got so many notes. And we will do a 2.0 or a second, another podcast on this, but go ahead, Cas.

[A]

You know, I would say, I think the biggest thing that I would like to say to the entrepreneurs out there, the people who are thinking about it, is like, we went over. It's not all glory. You will have freedom, but not always with your time, because it is 24 7, so watch out for your health. There have been times when Mike And I put everything in and let go of our health. And that's a big deal. It actually will cost you many years of your life in the future. So I would add one more book. I'd add Peter Attia's Outlive to the list because it really talks about longevity. And I think America needs to start rethinking what health means.

[C]

I agree.

[B]

It's so important. Mike, what do you got for us?

[C]

Only thing I'd leave you with is, you know, which I was reminded about earlier today, is just do the right thing. So you may have contracts and agreements and all this legal stuff, but just keep asking yourself, what is the right thing? How should I handle this situation? The right way. And it usually costs you something. It's going to cost you money, speed, control of something, ego, whatever. And I go back to Marc Benioff, who talked about this soon after he bought the business. Just, if you do the right things, things will work out. And when you don't do the right thing, optimizing for just money, not looking at the larger stakeholder group, whatever it is, that's when at least we find ourselves in situations that don't feel as great. And so personally, professionally, just keep that in the back of your mind, do the right thing, and all will work out.

[B]

I love it. Well, I appreciate you guys doing this tonight. It's a little bit later where you guys are at, and I'll make sure to follow up with you guys and definitely follow up on a phone call and get to know you more. Very much appreciative.

[A]

Thank you so much.

[C]

Appreciate it.

[A]

Thanks for having us.

[B]

You guys are amazing. Thanks so much for listening to this episode. Like always, we're going to close it out with the Tommy Truth, which is a little slice of wisdom from me to you that can help guide you in whatever you're striving towards right now. Don't spend too much time on Facebook and Instagram and tick tock. You start living other people's dreams. And let me just tell you this. I know a lot of the people and they don't live those lives.

[C]

Lives.

[B]

They're renting the car. The house is leased. They live this life where they spend every penny to make other people believe they're great. What I would tell you is live your own life. Look at the people you hang out with. You'll become like them. It's not easy, but learn to get in the right circles and everything will come. You won't go golfing every week with three people that are better than you and not become better. There's nothing in life you can't become better at if you hang out with the right people, living your own life.

[C]

Make it the best. Watch out are you hanging out with.

[B]

And keep your commitments and you'll be great. And that's it, guys. We'll talk to you next week.