Transcript

What It Takes To Build a Billion-Dollar Business with Mike & Kass Lazerow

From Tommy Mello · Episode page · Watch on YouTube

· 46 min · 8,493 words · 85 timestamped sections

This is the full, timestamped transcript of "What It Takes To Build a Billion-Dollar Business with Mike & Kass Lazerow", an episode of Tommy Mello published January 17, 2026 (46 min, about 8,493 words). It mentions 22 people, works and ideas, including Cass Lazero, Mike Lazero, Shoveling [__], Tommy (Mellow Millionaire host), Venture Capital.

What this episode is about

Mike and Kass Lazerow emphasize that resilience and the ability to endure challenges are essential traits for entrepreneurs aiming to build successful businesses. Drawing from their experiences in founding notable companies like Golf.com and Buddy Media, which was acquired for $745 million, they highlight the importance of risk mitigation and the need to embrace the difficult journey that often accompanies entrepreneurial success.

Key takeaways

  • Entrepreneurship is a relentless grind; resilience isn't just an asset, it's the currency of success.
  • Love 'shoveling' your way through failure? That's where true entrepreneurial grit and growth lurk.
  • Investors crave de-risking: minimizing uncertainty transforms 'maybe' into a resounding 'yes' for potential investors.
  • Successful partnerships thrive on complementary skills; it's a classic recipe where 'one plus one' equals magic.
  • Riding the entrepreneurial rollercoaster: it’s painful, exhilarating, and ultimately, where purpose finds its wings.

Who speaks in this episode?

What is discussed, and when

  1. – 5:00: Cass Lazero, Shoveling [__], Mike Lazero, Buddy Media
  2. – 10:00: Venture Capital, Private Equity, Health, Executive Search
  3. – 15:00: Venture Capital, Private Equity, Los Angeles
  4. – 20:00: Venture Capital, Liquid Death, Scopely, Los Angeles
  5. – 25:00: Private Equity, Buddy Media, Salesforce, Health
  6. – 30:00: Tommy (Mellow Millionaire host), Private Equity, Golf.com, Longevity
  7. – 35:00: Artificial Intelligence, Longevity, Shoveling [__], Buddy Media
  8. – 40:00: Sales, Health
  9. – 45:00: Health, Shoveling [__], Man's Search for Meaning, Longevity

Notable quotes from "What It Takes To Build a Billion-Dollar Business with Mike & Kass Lazerow"

  • So here we are, 30 years later and we wrote a book that's called Shoveling [ __ ] a love story about the entrepreneurs's messy path to success.
    about Cass Lazero · at
  • 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…
    about Health · at
  • Of them don't work out. and not just a majority but if you look at the numbers you know a good 90% plus of venture capital backed companies fail to produce that outsized return…
    about Venture Capital · at
  • 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…
    about Longevity · at
  • I'm going to ask you guys three repeat questions I ask in every single one of these podcasts. What's one piece of gamechanging advice you wish you knew in your 20s?
    about Tommy (Mellow Millionaire host) · at
  • 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…
    about Artificial Intelligence · at
  • 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.…
    about Mike Lazero · at
  • 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.
    about Shoveling [__] · at

Who and what is mentioned in this episode?

People

  • Cass Lazero — Person · Main guest · 3 mentions · first at
    She emphasizes team-building, empathy/EQ, founder support, health/longevity, and co-founder dynamics across decades of building companies.
  • Mike Lazero — Person · Main guest · 2 mentions · first at
    He recounts the Lazeros' entrepreneurial journey (Golf.com, Buddy Media), their investing approach, and views on VC vs PE, AI, sales, and post-exit life.
  • Tommy (Mellow Millionaire host) — Person · Host · 2 mentions · first at
    He guides the conversation with questions about entrepreneurship, VC/PE, exits, AI, and closes with advice on social media and networking.
  • Victor Frankl — Person · Referenced expert/author · 1 mention · first at
    Referenced as the author of Man's Search for Meaning, supporting the episode's theme of purpose amid suffering.
    You said my favorite book in the world, which is Man's Search for Meaning, Victor Frankle.

Books & papers

  • Shoveling [__] — Book · Core artifact (book discussed/recommended) · 5 mentions · first at
    The Lazeros' bestselling book frames the episode's theme: entrepreneurship requires enduring suffering and embracing the messy path to success.
  • Man's Search for Meaning — Book · Recommended book · 1 mention · first at
    Cited as a life-changing book about purpose and meaning, used to reframe entrepreneurial suffering and resilience.
    You said my favorite book in the world, which is Man's Search for Meaning, Victor Frankle.

Companies & orgs

  • Buddy Media — Company · Key company built by guests · 4 mentions · first at
    Their best-known company; positioned as a leader in social media marketing software and the centerpiece exit to Salesforce.
    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.
  • Salesforce — Company · Key referenced acquirer · 3 mentions · first at
    Salesforce acquired Buddy Media (stated ~$745M / close to $1B) and integrated it into Salesforce Marketing Cloud, illustrating a major exit.
    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.
  • Golf.com — Company · Key company built by guests · 2 mentions · first at
    Mentioned as one of the Lazeros' foundational companies and part of their early entrepreneurial track record.
    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.
  • Scopely — Company · Portfolio example · 2 mentions · first at
    Used as proof of their investing success; referenced as a major outcome (stated sold for $5B in cash).
    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. When you…
  • Liquid Death — Company · Portfolio example · 2 mentions · first at
    Illustrates their early conviction investing in unconventional consumer brands (water as entertainment).
    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. When you…
  • Time Warner — Company · Referenced acquirer · 1 mention · first at
    Mentioned as the acquirer of Golf.com (stated $25M), demonstrating an earlier exit before Buddy Media.
    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…

Concepts & topics

  • Venture Capital — Concept · Core topic · 9 mentions · first at
    Explained as funding 'inventing the future' with high failure rates; contrasted with private equity and discussed via deal flow/network effects.
  • Private Equity — Concept · Core topic · 6 mentions · first at
    Contrasted with venture capital as scaling/rolling up cash-flow businesses using leverage; discussed with caution about debt risk.
    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…
  • Artificial Intelligence — Concept · Core topic · 2 mentions · first at
    Discussed as a disruptive force: businesses must adopt AI or risk failure; also used to transform services like executive search.
  • Sales — Concept · Core skill emphasized · 1 mention · first at
    Positioned as a durable human skill in an AI-driven world; also central to recruiting and business growth.
    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.…
  • Health — Concept · Core topic · 6 mentions · first at
    Presented as a critical post-exit and ongoing priority; entrepreneurs often neglect it until after liquidity events.
  • Longevity — Concept · Supporting topic · 4 mentions · first at
    Discussed as a goal (staying active with future grandkids) and tied to reading/rethinking health practices.
  • Executive Search — Concept · Example acquisition/operating area · 3 mentions · first at
    Cited as a type of business they buy and improve, and as a domain being transformed by AI-enabled outbound and candidate identification.
    And we're buying businesses that are just great businesses like executive search firms and you know health care companies and firms that basically provide a great service to a customer like you do and build on the back of.
  • Web 2.0 — Concept · Referenced technology wave · 1 mention · first at
    Mentioned as a prior wave they identified early (alongside the internet and AI), reinforcing their pattern-recognition investing thesis.
    Our gift is in identifying people, identifying opportunities, which we did with the internet and web 2.0 know and AI and you know water. When I first met Mike Cesario, he had…

Places & events

  • Los Angeles — Place · Referenced event location · 2 mentions · first at
    Referenced as the location of an event where a founder discussed post-exit identity; also where VC network contacts are based.
    So when Peter Fam in LA who has a firm called science calls up about this crazy idea liquid death do you want to meet Mike? Yes. You know when I get a call from Howard Linden saying do you want to.
  • Turks and Caicos — Place · Anecdotal location · 1 mention
    Used in a story about lifestyle purchases (house/boat) and avoiding expensive distractions after an exit.
    A year. If it dries, flies, just don't do it. These boats are like we owned a boat once. We bought a house in Turks and Caos and it came with a boat and it was like the only…

Full transcript with timestamps

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

The more you derisk, the easier it will be for investors to say yes. 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. When you start a company, you're basically announcing it to the world and giving people a front row seat to your failure.

They've helped generate over $10 billion in realized returns. Their bestselling book, Shoveling [ __ ] reveals the real and messy path behind their success.

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. 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 category 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.

Thanks for having us. Thank you. We appreciate it. 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 whoever wants to take the questions.

Mike, you start. Yes. 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 uh something that people actually wanted to do. Um and the internet started the commercial internet while 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 and went public. We then kept going. Uh, Castargolf.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.

I love it. Cass, what do you think? I mean, Mike said it pretty well. Um, 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 and we wrote a book that's called Shoveling [ __ ] a love story about the entrepreneurs'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 [ __ ] shoveling that they have to do and we are here for them. What would you say? What do you enjoy the most, Cass? What what what's your passions in business? Where do you get excited to go into a business and help out?

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 um good at what I call moneyballing. So, I I like to put the right people in the right spots to get over the plate. And that's the the strength that I bring and it's also what I love doing.

I love it. Mike, what about you? Yes. So, we love entrepreneurs. I mean, people ask us all the time how like why' we do a hundred deals ourselves off our own balance sheet? Why did 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 [ __ ] 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 doortodoor 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 and 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 know and AI and you know 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 they even launch, you know, 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, you know, 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 to, you know, for future generations without, you know, the crutch of venture capital. Um, those are the real entrepreneurs.

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 Baso 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, uh, 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 capital as a

Yeah. So venture capital is about inventing the future. It's about how do you um 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. Um and not just a majority but if you look at the numbers you know a good 90% plus of venture capital backed companies fail to produce that outsized return and it takes a different mentality to go from zero to one. 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 you know health care 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.

Cass, what what do you think you you guys obviously probably have people whether it's there's probably 10 people for different types of marketing, you got the the right CFO backgrounds, you got the right FPNA teams, you got the right executive searches. What what do you think you guys are known to bring to the table? 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. Um, 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 247. So I think we also bring a lot of understanding and empathy to entrepreneurs.

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.

Founders who sell oftenimes 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 three billion said I'd give the money back right now to get my business back. And you know 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 Cass 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 10:00 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 Caos and it came with a boat and it was like the only thing we fought 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 stockpicking. I'm talking about trusts. I'm talking about tax strategies, which is ironic. I'm sitting in New York City which is the worst place and

you know making sure you protect your estate right. Yeah. And a lot of us like just because we have success in business doesn't mean we're good at like managing our own money. Just realize that. Realize that like 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? I

I I agree. I mean, look, the the right person, the tax strategy, the trust, there's there's so much if if you got a lump sum of money, it could be 10 million, 100 million, or a billion. Uh, but do you believe like the oh [ __ ] money should just be like this is going to continue to make money. This is like this is our safe or or do you just say let's let's bet it all and diversify it and more ways to grow it? 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 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 uh spent on them in terms of education.

Um, 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 um, 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?

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. 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 happen to hang out with a lot of entrepreneurs.

As entrepreneurs who returned several funds for our investors, meaning like they invested in our company and 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 Fam in LA who has a firm called science calls up about this crazy idea liquid death do you want to meet Mike? Yes. You know when I get a call from Howard Linden 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, right? 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? Yeah, I do agree with that. Well said.

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

yeah, it was Iron Deer I know well. Yeah, Byron. I met him the other day at a football game. He's a real great guy. Uh and then they in you know some they talked about Fusion. They were like, "Yeah, we're we're a couple years out from Fusion. There's about 10 companies. We're investing big." And then they said, "It might sound unorthodox, but we invested in the 49ers because we think people are going to want in this AIdriven world to come together

entertainment." Yeah. Community. And so I I love learning about this stuff. And and you know, I I 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.

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 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 your 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 um 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.

There's basically like Yeah, I was just talking to a founder about this and I just gave three pieces of advice. You know, number one is buy time, not toys. So, no lifestyle, inflation. And the idea was that like before you even think about your investment portfolio, design your calendar like design what you want your life be proactive because too much of 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, like don't worry about spray and prey investing. You could hire someone to do that, but what are the areas that you deeply understand that 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, you know, there's hubris that comes with selling a business. Like 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, 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 [ __ ]

I I would add one more too, Mike, that we forgot. Health. Number four, health. So, 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.

You know what's interesting? I was at a private equity event and I got to speak. I was the only founder there speaking and I asked the guys in my, you know, Cortech, which is our PE fun. I go, "What am I going to do up there?" They go, "Just go up there and be you. Tell stories like you always do." And luckily, I got a standing ovation. I 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 uh I told a lot of stories about my family and my mom.

That's so good. So, what do you guys feel? especially if it's a platform. What is the the process or the thought process of not having the founders role?

Yeah. So, we're we're big believers in founders staying and as are the people we're closest with. You know, Mark Beni off 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 we're paying in stock and revest it 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're not buying 100% of it. One deal that we're doing right now, we'll 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, you know, 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. And 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 a customer and delivering for them. What do you not like?" H the payroll and all the [ __ ] around people who it's like babysitting and you're like, "Okay, well, let's go." Like,

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 a 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. Um how much debt do you guys typically use in a deal? I mean, do you use like maximum leverage if you can get five or 6x?

So we use zero right now. um 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, you know, as a real estate developer because of debt and we've never, you know, 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 overlever the business, but if we are going to start um you know bringing on debt probably no more than 50% so we have a debt coverage that we can live with. Um and we're also like different than private equity firms. And I would I share this cuz 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, you know, like self- storage. They short-term debt on a lot of properties and as the interest rates went from zero to 7%, they just got crushed, right? 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.

A lot of people get burned out. I my first exit I I lost a lot of my like I had lopia. Like it was like 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 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 uh you know I want to do it again and uh 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.

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 uh 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. Um 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.

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, uh, 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 really a big deal. Um, I'm going to ask you guys three repeat questions I ask in every single one of these podcasts. What's one piece of gamechanging advice you wish you knew in your 20s?

Mike, you can start. 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 6 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 hyperfocus 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.

Mine would be that my 80% as an entrepreneur is probably better than most people's 150%. So I I 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 allin 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.

That's great advice. Uh, if you had to start over, you get $10 million. Where's the $10 million going?

I think 25% is going into our boring 7 to 10% return. I think 25% is going into venture and I think um probably 25% is going into the kids we have and probably like um experiences I think because that's how we'll build memories with our kids later on. And um 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

with 10 million bucks. Like how are you going to build homes and live? I don't know where.

I'm just giving you the thead I'm glad we're already rich cuz we would not agree on that.

I'm thinking I'm thinking about like okay we're going to need part of it to live. We'll get deeper here, Mike. But where do you guys Where's the main home?

New York City, and then we have a house upstate. Yeah. So, we have a place in Hudson Valley, which we love. Um, and then, uh, 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. 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 the people are worth a billion dollars are living like they're worth 10 billion.

What's your biggest professional dream at the moment? 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 best sellers with a title called Shoveling [ __ ] and we said, "Okay, that's like catnip for us. We'll just work our ass off and make it happen."

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

All right. Um, 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 uh, unlike the industrial revolution, it's not like you're just going to go learn something else. It's 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 or inva's 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. Um I don't know I I don't know where we're going. What is what is your take on that? I mean, so I do believe in like what Mark Cuban has been saying lately where there are two types of businesses.

There ones that adopt AI and then there ones that are out of business. Um, 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, you know, a group that funded a company called etch.ai 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 the 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 sea 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 got to, you know, everyone who we want to 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. Like we just don't listen very well. And I mean listen, not just like hear what he or she's saying, but like you know, 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.

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

I I think that you can to a point teach 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 IQ's, 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 we used to I used to run a ton of different meetings in all of our companies based on EQ to 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. So, 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.

And look at look at me, Seth. 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'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. You know, there there's this there's this book that u 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. Uh farmers don't necessarily have to have these hunters. Uh 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 uh 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 Tik Tok 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. 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 um I don't think everyone should be an entrepreneur. I think you've got to 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.

My experience, I used to 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. Uh, 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 would invite you guys out. Uh, so you got an invitation coming. I want to get to know you guys a lot more.

I would love to. Uh, and we got to pick up Shoveling [ __ ] Everyone that's listening to this, um, New York bestseller, and I've got a million questions I didn't even get to. So, uh, is there anything any books that you feel like are a must readad other than shoveling [ __ ] Um, like that will change people's lives?

You said my favorite book in the world, which is Man's Search for Meaning, Victor Frankle.

Victor. Yeah. 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, you know, 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, um, 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 um that we believe. And then, you know, 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, like why why I was so excited about coming onto this podcast is that there's so

many people who were trying to do what you're doing who've done nothing. You know, we did so many as part of the book like earlier in the year and there only a few who actually have built real businesses and you could name them probably on both hands, right? And so, uh, you know, we just appreciate the time that you've given us and hopefully first of many conversations.

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.

Well, it's also like who do you you surround yourself with, right? You want to surround yourself with the people that you aspire to be

100%. And uh 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. Uh and we will do a 2.0 uh or a second uh another podcast on this, but uh go ahead Cass. You know, I would say um 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 247. 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's it it actually will cost you many years of your life in the future. So I would add one more book. I'd add Peter's Outlive to the to the list because it really talks about longevity and I think America needs to start rethinking what health means.

I agree. It's so important. Mike, what do you got for us? 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, you know. And I go back to Mark Beni off 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, you know, situations that aren't don't feel as great. Um, and so personally, professionally, just keep that in the back of your mind. Do the right thing

and all will work out. I love it. Well, I appreciate you guys doing this tonight. U, it's a little bit later where you guys are at and, uh, I'll make sure to follow up with you guys and, uh, definitely follow up on a phone call and get to know you more.

Very much appreciative. Thank you so much. Appreciate it. Thanks for having us.

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 Tik Tok. 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. 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 in your own life, make it the best. Watch out you hang out with and keep your commitments and you'll be great. And that's it, guys. We'll talk to you next week.

Questions about this episode

Who speaks in "What It Takes To Build a Billion-Dollar Business with Mike & Kass Lazerow"?

Cass Lazerow (Guest), Tommy Mello (Host), Mike Lazerow (Guest).

What is "What It Takes To Build a Billion-Dollar Business with Mike & Kass Lazerow" about?

Mike and Kass Lazerow emphasize that resilience and the ability to endure challenges are essential traits for entrepreneurs aiming to build successful businesses. Drawing from their experiences in founding notable companies like Golf.com and Buddy Media, which was acquired for $745 million, they highlight the importance of risk mitigation and the need to embrace the difficult journey that often…

What is mentioned in this Tommy Mello episode?

22 people, works and ideas are mentioned, including Cass Lazero, Mike Lazero, Shoveling [__], Tommy (Mellow Millionaire host), Venture Capital, Buddy Media. Each one on this page links to its own page with every episode that mentions it.

How long is "What It Takes To Build a Billion-Dollar Business with Mike & Kass Lazerow"?

The episode runs 46 min; the transcript is about 8,493 words in 85 timestamped sections.

More from Tommy Mello

About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated January 24, 2026.