Kass & Mike Lazerow: The Billion Dollar Burnout

Summary

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The Messy Parts with Maryam Banikarim

Episode: Kass & Mike Lazerow: The Billion Dollar Burnout

Date: June 23, 2025

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Episode Overview

In this candid conversation, Maryam Banikarim welcomes Kass and Mike Lazerow—serial entrepreneurs, married partners, and authors of Shoveling Shit—to explore the unvarnished realities behind their headline-making business successes. Together, they discuss the grinding work, high personal costs, lessons learned, and the ongoing quest for meaning beyond monetary wins. With humor and unfiltered honesty, the Lazerows reflect on marriage, parenting, health, and redefining purpose in the "second chapter" after a billion-dollar exit.

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Main Discussion Points & Insights

1. The Unglamorous Reality of Entrepreneurship

• Everyday Struggles:

  • “The messy parts are just every single day, the hard little fights, the annoying stuff, the hard stuff that you do. Because there's very little glamour in being an entrepreneur. There's lots of freedom, but there's little glamour.”
    — Cass Lazaro [00:00]

• Freedom Redefined:

  • The couple highlights the difference between being free from a boss’s idea versus true autonomy: "The freedom is that we're not chained to someone else's idea."
    — Cass Lazaro [03:09]

• Success is Not Always Joyous:

  • Reaching an outcome like selling Buddy Media for nearly $1B left them numb, not jubilant:
    "It should have been the greatest day week of our life...And we were relatively numb."
    — Mike Lazaro [00:16], [21:48]

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2. Transparency and Resilience Amid Failure

• Losing it All — Together:

  • Early in their career, after selling Golf.com to a company that went bankrupt, they lost friends and family investors’ money:
    “We thought before the call that we were very rich...Then it's like, wow...we have lost all of our investors' money. And our investors were...family members.”
    — Mike Lazaro [03:36-04:33]

• Sticking With the Team:

  • Radical honesty saved their company culture:
    "Every single person did [stay]. The crazy part is that we learned that if you are transparent and you share the bad...there's no surprises."
    — Cass Lazaro [05:33]

• Lesson:

  • Transparency becomes the glue holding a company together through crises and pivots [06:04].

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3. Marriage, Partnership, and the Off-Button Myth

• Working and Living Together:

  • They've been business partners as long as they've been married. Division of roles and respect are key.
    “It's our love language, and it's like shoveling shit. A love story...it's miserable and awesome.”
    — Mike Lazaro [06:44-07:09]

• Turning Off Is Hard:

  • "I don't have an off button unless I have to have an off button. Being a mom requires me to not have an off button."
    — Cass Lazaro [07:24]

• Strategy:

  • The cheat code: Regular date nights (Wednesday and Saturday)—sometimes just for crashing on the couch [07:45].

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4. Identity, Suffering, and the Need to Build

• Entrepreneurial Drive:

  • The Lazerows and host ponder if founders are “broken” like comedians, always seeking to prove something.
    "To me, it’s more about suffering...That's really the difference with entrepreneurs, is that we like that suffering."
    — Cass Lazaro [09:10]

• Boredom with ‘Retirement’:

  • Mike tried retirement and painting—fun, until it wasn't:
    “It was fun until it wasn't. There are things called hobbies, which are things you love but aren't good at.”
    — Mike Lazaro [09:53]

• Joy and Misery from Building:

  • “We find our purpose in building...and it's where we find our misery and your joy.”
    — Mike Lazaro [31:35]

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5. Impact of Dysfunctional Childhoods & Competitive Nature

• Origin of Drive:
  • Both Cass and Maryam attribute their relentless drive and competitive edge to challenging upbringings.
    “I believe that you can improve on something every single day, period.”
    — Cass Lazaro [17:38]

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6. Parenting & Passing on Grit

• Modeling vs. Teaching:

  • They note how hard it is to teach resilience, but children do model adult behavior more than obey explicit advice [19:46-20:55].

• Guilt and Trade-Offs:

  • Despite successful careers, their children see them as strong and present when needed.
    “All three of my kids think I’m very strong, very dedicated, and I show up when I need to.”
    — Cass Lazaro [25:45]

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7. Physical and Emotional Health Costs

• Personal Toll:

  • Both suffered after their big exit: Mike was overweight, Cass had severe migraines.
    "It took me a full year to get my nervous system back after we sold the company, like, to get it, like, recalibrated."
    — Cass Lazaro [22:31-22:53]

• Defining a Life Worth Living:

  • “It's not just about how to excel at work, but how do you do it and create a life worth living?”
    — Mike Lazaro [22:53]

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8. Giving Back, The Book, and Lasting Lessons

• Motivation for Writing Shoveling Shit:**

  • “To help as many entrepreneurs as possible...why am I saying the same messages over and over again five to ten times a week to all the entrepreneurs? Why can't I say it more?”
    — Cass Lazaro [28:33]

• Radical Generosity:

  • “The more we give, the more we get.”
    — Mike Lazaro [28:53]

• Scaling Wisdom:

  • The book encapsulates their “cheat codes” for entrepreneurship and life [30:03].

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9. Examining Legacy: Tech, Social Media, and Regret

• Reflections on Social Media's Impact:
  • They candidly reckon with the unintended costs of the tech they helped build:
    “We really believed that when you connect the world...it was going to help democracy...And we didn't know that these platforms were only going to optimize for engagement...they have destroyed democracy and people's mental health, especially kids.”
    — Mike Lazaro [35:09–36:21]

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10. Advice, Favorite Rituals, and Rapid-Fire Fun

• Actionable Takeaways:

  • “Do the right thing. Regardless what the contract says or what the social pressure or investors say, do the right thing and things will work out.”
    — Mike Lazaro [40:34]

  • “Be radically transparent with everything you do.”
    — Cass Lazaro [41:03]

• Rituals:

  • Plan date nights and time with friends—if you don’t, relationships and connections decay [24:08].

• Quirks and Surprises:

  • Mike is a self-admitted crier: “I'm a crier. I'm actually very emotional.” [39:15]
  • Cass loves fly fishing for its meditative, single-focus quality [40:02]
  • Potluck picks: marinated flank steak (Mike), Lipton onion dip (Cass) [37:14–37:38]
  • Karaoke: “Say You, Say Me” (Mike), “In Your Eyes” by Peter Gabriel (Cass) [36:55–37:10]

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Notable Quotes

• “It's miserable and awesome.” — Mike Lazaro [07:09]
• “Transparency becomes a glue, a sticky glue in a company when you’re going through pivots and changes.” — Cass Lazaro [06:04]
• “We find our purpose in building...and it's where we find our misery and your joy.” — Mike Lazaro [31:35]
• "If you don't prioritize things, they will decay and you'll be left wondering." — Mike Lazaro [24:08]
• “The more we give, the more we get.” — Mike Lazaro [28:53]
• “Be radically transparent with everything you do.” — Cass Lazaro [41:03]
• “Do the right thing.” — Mike Lazaro [40:34]
• “We really believed that when you connect the world through these platforms, people had access...and it was going to help democracy. And we didn't know...they have destroyed democracy and people's mental health, especially kids.”
  — Mike Lazaro [35:29–36:21]
• “There's very little ROI on kids... you get these little moments.”
  — Cass Lazaro [20:22]
• “I believe that you can improve on something every single day. Period.”
  — Cass Lazaro [17:38]

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Timestamps for Key Segments

• Entrepreneurship’s Realities: [00:00–03:18]
• Lessons from Failure: [03:22–06:14]
• Marriage & Work Partnership: [06:14–08:16]
• The Drive Beneath Success: [09:10–10:47]
• Mental & Physical Health Challenges: [11:13–13:19], [21:48–22:53]
• Parenting and Role Modeling: [18:27–20:55]
• Selling Buddy Media—Personal Fallout: [21:48–23:04]
• Purpose After Exit: [23:04–24:24], [31:35–32:37]
• Giving Back and Writing the Book: [27:31–30:03]
• Social Media Regrets: [35:09–36:39]
• Rapid Fire Fun: [36:46–40:09]
• Final Advice: [40:34–41:18]

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Summary Takeaways

• Success is messy, even when it looks like a highlight reel.
• Radical transparency and honest communication build trust and loyalty, in business and in life.
• Building and creating, with all its challenges, is often the true source of joy—and sometimes pain—for lifelong entrepreneurs.
• Relationships, health, and purpose can be eclipsed by ambition—prioritize them or risk losing them.
• Give generously: wisdom, time, and kindness multiply.
• Don’t be afraid to openly discuss your struggles—those are the real teachable moments.
• Even after a billion-dollar exit, a life worth living comes from connection, learning, and impact, not just financial success.

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Transcript

[Cass Lazaro]

The messy parts are just every single day, the hard little fights, the annoying stuff, the hard stuff that you do. Because there's very little glamour in being an entrepreneur. There's lots of freedom, but there's little glamour.

[Mike Lazaro]

I think it culminated when we sold the company, the last one, when we sold Buddy Media. It should have been the greatest day week of our life. We sell for close for a billion dollars. It's like life changing money. It's like after all these years and we were relative numb.

[Podcast Host]

I couldn't be more excited to actually share the story of Mike and Cass Lazaro with you. The thing that's amazing about them is that they're these incredible entrepreneurs that have had hockey stick companies that they've built and exited. Right? But what's most amazing about them is that they have a book out called Shoveling Shit. So it seemed appropriate to talk about the messy parts of their journey, which includes all kinds of things, to the difficulties of being a working parent and an entrepreneur, to, you know, managing your health while you're trying to do all kinds of things. You are gonna wanna hear their story, but also you're gonna wanna hear the tips that they have to share to really manage the imbalance that comes with success. So I can't thank you both enough for coming on the show. I know the show's new, so, you know, it's a leap of faith into shoveling shit together, which I really love. So I think we should just dive right in. Right? You guys actually have a book that's out. It's called Shoveling Shit. I love that it came to my house with a, you know, if I look at your career, it's actually not. It doesn't seem like it's full of shit. It seems like it was like, you know, up and to the right the whole way. But clearly in writing the book and a lot of the work that you do with founders who come after you, you talk about the mess. And this podcast is about the messy part. So I thought we could start by you picking one or two moments that were particularly messy that maybe people wouldn't know about.

[Cass Lazaro]

I think it started like, if I had to pick one. Every single company has kind of happened around our kids. Like, we give birth to them and then the next, I guess I give birth to them. She does most of the birthing and then Mike has an idea and then it's like us trying to do stuff with very small children. Our last company, Buddy Media, I had the C section on May 24, 2007, for our last child and wheeled into the recovery room. And he's like, I've got it. And I'm like, oh my God, he got it. Me sushi. Haven't eaten that in like 10 months. And he's like, no, I know the next idea. And three months later, I'm on the floor nursing and then putting her down in her pram while I'm drilling IKEA desks together, like building desks for our new office. So the messy parts are just every single day. The hard little fights, the annoying stuff, the hard stuff that you do. Cause there's very little glamour in being an entrepreneur. There's lots of freedom, but there's a little glamour.

[Podcast Host]

Well, there's freedom when you succeed.

[Cass Lazaro]

Yes and no. I mean, we call it freedom from being behind a desk. So we would say, like the freedom is that we're not chained to someone else's idea.

[Podcast Host]

And Mike, is there a moment when you look back on this journey?

[Mike Lazaro]

Yes. So we learned the most when we failed. And we failed many times. So we launched Golf.com, it went great. We sold it, sold it to a Sequoia backed company in the Bay Area. They went bankrupt in March.

[Podcast Host]

March.

[Mike Lazaro]

Right before the whole market collapse. March 2000. And we got that call saying Sequoia has pulled out of our financing. We've pulled our S1, which means we're not going public and we can't pay payroll. You can buy the company back if you want. This is the CEO of the company that we sold it to. We thought before the call that we were very rich and we were very excited that we were young, we had one child and we were. Then we just got married actually three months earlier. And we were kind of ready to go with our life. And then it's like, wow, like we didn't succeed. We actually have lost all of our investors money. And our investors were what are called family members because we didn't really know VCs at the time. At a time, New York didn't have a VC community. Chicago, where we were living, didn't. What did we do? We just shuttled shit. We went to the West Coast.

[Podcast Host]

But you said you lost friends, like as a result of.

[Cass Lazaro]

Yeah, because we had friends there.

[Podcast Host]

Family.

[Cass Lazaro]

Yeah.

[Mike Lazaro]

We were very upset because we didn't have a culture of like this like investment culture of like seed capital and how risky it was. People didn't understand. They knew we were starting a company, but the investors were, you know, doctors and lawyers and people who had really never done dot com investing. Right. Like we're 1999. This is new. And. And we had to tell them, get the elephant in the room that, you know, you thought that you were going to make, like, eight times your money. We actually aren't going public. You know, what we said about the IPO is not happening. And I think Sequoia pulled out. I don't blame them, because they sensed that something was happening which led to the crash. So we told the investors, and we were transparent with them. Most importantly, transparent with our team, because you can't hide the fact you're not gonna be able to pay them payroll.

[Podcast Host]

But most of your team stuck around.

[Cass Lazaro]

Every single person did was. The crazy part is that we learned that if you are transparent and you share the bad, all of the, you know, information is power to them. There's no surprises. Like, this was new for us. We didn't hide it. We didn't, like, try to work on it behind closed doors for, you know, a week. It was like, this is what just happened. We're going to tell you every step of the way what we're doing, but we can't pay you because we don't have any more bank accounts.

[Podcast Host]

And they all stuck around.

[Cass Lazaro]

Yes.

[Podcast Host]

So, I mean, messy, but kind of also an amazing thing.

[Cass Lazaro]

But that was a big lesson in transparency, that transparency becomes a glue, a sticky glue in a company when you're going through pivots and changes.

[Podcast Host]

So the other thing I noticed in reading the book is that, you know, you've been together for a long time and actually business partners for the entire duration. Really?

[Cass Lazaro]

Yes.

[Podcast Host]

As somebody who's now started working with her husband, probably, I don't know, for five, he might say seven years, I would have thought I would never be able to work with him. There's a lot of messy parts that comes to being partners at work and at home.

[Mike Lazaro]

Tell us more, please.

[Podcast Host]

Well, we can compare notes. How about that? I'm happy to dish if you're willing to dish.

[Mike Lazaro]

Unfortunately, he's not here with us, but we could talk out in the open. It's our love language, and it's like shoveling shit. A love story is the title. And the reason is because, yes, it's hard work. Yes, it's miserable. Yes, it's full of suffering together, we love it. There's nothing we'd rather do. So it's this dichotomy of holding two seemingly different ideas at once, which is, it's miserable and awesome.

[Podcast Host]

But do you have an off button? I mean, I think one of the things that I find now that I work with my husband Andy, is that sometimes he's like, you can never stop. Like, it seems like you guys can also never stop.

[Cass Lazaro]

So wait, let's just be clear on this. I think.

[Mike Lazaro]

Listen to what Cass says.

[Cass Lazaro]

So, like, I already see how this works. I don't have an off button unless I have to have an off button. But I also think that being a mom requires me to not have an off button, right? So it's not like I could be, like, pause. I'm, like, not gonna be a parent. I think men, fathers tend to have that off button that's really close to them. They can turn it on and off. But, you know, one of the cheat codes in there is date nights, Wednesday and Saturdays. And we did that as soon as we could afford it. And we had a babysitter whether we went out or not. Like, sometimes we were just, like, you know, on the couch, like, looking back and sleeping. During those times when you go out.

[Podcast Host]

On date night, do you still talk about work?

[Cass Lazaro]

Sometimes. Sometimes we just want to get it out of the way. Like, I will say, like, okay, I have three things I just wanted to talk to you about. And then we'll just start talking about.

[Mike Lazaro]

Usually not, though. But if there's something on our mind, we don't say, you can't, because that just, like, builds up inside.

[Podcast Host]

So it's interesting. Yesterday, I was at a conference that was a lot of founders here in New York. And I was in a session that they had, which was about chapter. The second chapter, which I think was off of a David Brooks book. Like, you've succeeded. You've gone to the other part. Now what? And a lot of the who had actually done quite well were talking about how their identity was wrapped up in being a founder. It was really hard. Even when they got to the other side and had done quite well. And the phone rang, but not in the same way. And then they also. One of them said, to be a founder, it's like being a comedian. You have to be broken. It's like this drive, which I thought was such a great analogy, actually. He was like, there's this drive that you're trying to prove something in some way. Do you think that's true? Because when I read your story, you both had interesting childhoods. I also had that, which I think is also part of my drive. Do you think there's something to that?

[Cass Lazaro]

I think it's. To me, it's more about suffering. So I was an athlete my whole life, and so I know what it's like to suffer. I know what it's like to get up early, have to train before school, train after school, work things into a very tight schedule and work towards something, towards something that you're always improving on. And I think that's really the difference with entrepreneurs, is that we like that suffering, and we like working towards something that you're gonna get better at, you're gonna try to win. And when we don't have it, we lose our way. We lose our purpose and our passion. I mean, this one definitely couldn't do it. Like, he tried to retire and start painting. That was fun to watch.

[Podcast Host]

Yeah. So how was that?

[Mike Lazaro]

It was fun until it wasn't. There's things called hobbies, which are things that you love but aren't good at. And so I thought I would.

[Podcast Host]

You have hobbies?

[Mike Lazaro]

Yeah.

[Cass Lazaro]

Oh, he has a lot of hobbies.

[Podcast Host]

Like what?

[Mike Lazaro]

I love seeing live music. I play golf.

[Cass Lazaro]

Just seeing live music.

[Podcast Host]

Like, do you follow a band around? Like, is there more to the story?

[Mike Lazaro]

Why does that follow the band Phish? I'm a big Fish fan. It's the only relationship I've had before cast. I've been with them since I was 18.

[Podcast Host]

Oh, my God. I already love that you describe it as you've been with them. Okay.

[Mike Lazaro]

Well, I only say that because it's like, as advertised, right? Like, she knew about this228shows.

[Cass Lazaro]

29.

[Mike Lazaro]

I don't know how many.

[Podcast Host]

Maybe she didn't know quite that many.

[Mike Lazaro]

Yeah, a lot. And it's just a way. It's the me part. Like, you gotta have we and me. And for me, I don't do a lot. But what I do. Excuse me, is you don't do a lot is important to me.

[Cass Lazaro]

You are very social. You're definitely the extrovert.

[Mike Lazaro]

Yeah, I'm more social. Class is like a cicada. She emerges every 17 years.

[Podcast Host]

But I actually noticed that, Right. Like, you're much more the front guy. You do a lot more of the operation. We have that, me and my husband. Right. I mean, it'd be hard, I think, to have two of us.

[Mike Lazaro]

It's the only way to do it, I think.

[Cass Lazaro]

Two of us on the top, you can't overlap.

[Mike Lazaro]

And I can't operate anything. I could barely drive. She's the best operator I know. So it's perfect.

[Podcast Host]

But. Okay, so let's go back, because I know you had a heart issue, like, when you were younger. Yes. 19, I think. And I remember reading you saying that that actually caused you to be fearful and yet in some ways, you leaned into that fear. Like you said, I was fearful to date. I was fearful to eat.

[Mike Lazaro]

I was very driven as a kid. I didn't feel great as a kid. I wanted to be an adult. I wanted to work. Other kids went to these summer trips, and I work and loved it. And I was very stressed out as a kid. And I got an ulcer, a stomach ulcer.

[Cass Lazaro]

At what age?

[Mike Lazaro]

I forget. I think 16, 15, 16. And I was also born with a congenital heart defect, which there's a hole in between the two ventricles, which lets unoxygenated blood to be pumped back to the body, which is not great. It started to expand when I was 19. They went in and fixed it, and they saw some valve damage. They tried to fix the valve. Eight days later, I happened to be at my doctor's office and it burst.0. My doctor looked at my blood pressure and it was zero, which you don't want. That's bad.

[Podcast Host]

That's not a good science.

[Mike Lazaro]

I'm not a science person.

[Podcast Host]

I'm not a doctor, but that doesn't sound good.

[Mike Lazaro]

So I would have been dead if I was at home, because I probably would have gone to sleep, would have passed out. Respiratory depression, who knows? Rush to get an emergency valve replacement. I've had that valve for 32 years. St. Jude's number 25, knock on wood, it's still working. I came out of that surgery, I'm told, and I felt as a changed person.

[Podcast Host]

What does that mean?

[Mike Lazaro]

I was not stressed out. I was very chill. I was happy to be alive. I was like, this is great. I didn't die. What else can happen? I'm alive. Let's go.

[Cass Lazaro]

His mom. I've grilled his mom a lot on this, and he's understating how stressed and anxious of a kid he was. He had massive anxiety.

[Podcast Host]

Do you think that that massive anxiety was related to the heart valve?

[Mike Lazaro]

I think it was related to, you know, it's just the sum of everything.

[Cass Lazaro]

Definitely the ulcer.

[Mike Lazaro]

It's everything, right? Like, I loved my childhood, but it was pretty dysfunctional. So, like, divorced parents. Dad had mental health issues, business issues. A big family, right? Four of us in the house, lots of demands, you know, And I was like a go getter. Like, I wanted to succeed, not in school. I could care less about school. But I applied when I was 13 to be on the board of the Sallie Mae Corporation.

[Podcast Host]

Why not?

[Mike Lazaro]

And I got a letter that said the argument was like, you should have some students on student loan, marketing Associations. And they're like, thank you, but no thank you. I remember meeting our current president, who was a business person at the time, and I'd read the Art of the Deal, and it just seemed, like, cool to run a business. And I studied, like, a lot of these business people.

[Podcast Host]

But you went to journalism school. Just to be clear, you didn't go to business school.

[Mike Lazaro]

I went to journalism school for one reason. It's the only place I got in. I applied to five schools and got in.

[Podcast Host]

But, I mean, did you apply to five journalism schools or five different kinds of schools?

[Mike Lazaro]

No, no journalism schools. The only reason I got in is because I did the high school newspaper. I got rejected from Harvard and Penn.

[Podcast Host]

But did you apply to Harvard and Penn for journalism? No, this is undergrad.

[Mike Lazaro]

This is just undergrad.

[Podcast Host]

I see. Okay.

[Mike Lazaro]

So the last letter I got was Northwestern, and I was like, one for five. But I'm like, I guess I'm going to Northwestern. I thought I was in Seattle. Turns out it was outside Chicago.

[Podcast Host]

And did you think for a minute that you might be a journalist?

[Mike Lazaro]

Yeah, because I'd worked in the summers. I worked for Mort Kondraki, who ran Roll Call and really loved that. Talking to senators and congressmen, writing for the newspaper, Capitol Hill. And they didn't have a lot of money, so they'd have interns that just did stuff. Like, I'd go meet with Ted Kennedy to talk about his financial disclosure forms, and then I would get it wrong, and then he'd yell at me. But it was exciting, right? I was both not a great journalist, and I could see that journalism was going to be impacted by the Internet, which took off while I was an undergrad. So if you think of, like, Netscape going public and Yahoo going public, if you started school in 1992 like I did and graduated in 96, much different than 89 and graduating a few years earlier. And so the Internet, I thought, was gonna be huge. I went down that rabbit hole. And when I went to this wedding right after I graduated, there was this beautiful woman there who also was doing Internet stuff. I knew I was very nervous to talk to her, but I asked her to dance. The rest is history. And that's how we connected. So when we say we work together, it has always seemed natural. The most amazing part, I think, of our journey 30 years later isn't that we love each other, which we do, but we actually like each other. We like spending time, and we've shared interests. Not the fish stuff. I get it.

[Cass Lazaro]

He was always the first person I. We were living together after we, you know, I moved there to Chicago. And he was the first person that I would say, okay, like, this is what happened at work. I can't figure this client out. What do I do? And he gave me the advice, so it made sense that I'd want him on the team.

[Podcast Host]

It's so interesting. It's like you became a team pretty early.

[Cass Lazaro]

Very early, Very early. And relied on each other very, very early. Like, I remember us moving in and do you remember when we were on Lille street and I said, okay, this is the first time moving in. And I came out with like a toilet bowl cleaner. And then I came up with like a mop.

[Mike Lazaro]

And.

[Cass Lazaro]

And I was like, which one do you want? And he took the mop. And so we kind of started dividing from there.

[Podcast Host]

So it's interesting you mentioned a dysfunctional childhood. I grew up in Revolution and had all kinds of pivots and crazy turns along the way. I often wonder. Cause people ask me, what drives you? You could do something else or something less stressful. Or not decide to launch a podcast at whatever age I am, which I can never remember. Like, there's something that drives you, right? Like impact. And you talk about the desire for impact. I mean, I often try and think, like, what is that in me? That, like, is almost not letting me stop in some ways.

[Cass Lazaro]

I know what it is in me.

[Podcast Host]

Okay.

[Cass Lazaro]

I believe that you can improve on something every single day, period.

[Podcast Host]

And does it matter what that something is?

[Cass Lazaro]

Nope. So some people might call that learning, but I actually think, like, I can become a better human. Whether that's listening to my kids, being more present, being more aware, better marketer, better at helping someone, being there for somebody. I can do that every single day. And that's just something that I think I got from being so competitive.

[Podcast Host]

Well, I was gonna say, I totally see that competitive streak from an athlete.

[Cass Lazaro]

At such a very early age. Right. And also having a dysfunctional. You had to fight for your voice and your messages and to get attention.

[Podcast Host]

So it made you self sufficient. Right. I mean, I sort of think about that.

[Cass Lazaro]

Yes.

[Podcast Host]

Now you have three kids and I have two kids. I think about that. Like, in some ways it's been easier for them. I would say.

[Cass Lazaro]

Wait, we've also enabled them.

[Podcast Host]

Yeah, okay. Exactly. Like we're professional problem solvers, so it's hard not to solve their problems. Do you think about that as you raise children? Because that's definitely a messy part.

[Cass Lazaro]

Oh, yeah. And I. Mike and I talk about this all the time. My dad, for good or bad, saw talent in three out of the four of us as siblings and pushed us, pushed us hard because he saw the talent and he thought that was a vehicle to get to better education and that better education was going to be something that we could use in our life. And he specifically said that about sports. But when it came to our kids, I never wanted them to have that. I never wanted them to, like, have the, like, wrestling thoughts that I had of, like, oh, I hate this. I hate what I'm doing right now. And I never pushed them. And so we have three kids who are kind of athletic, but didn't have that grit, resilience, kind of suffering that I did.

[Podcast Host]

I mean, because I wonder, like, you know, you want to pave the way so that it's easier for them, but it's hard to teach resilience.

[Cass Lazaro]

It is.

[Mike Lazaro]

Well, it's hard to teach anything to kids. We talk to them and they don't listen.

[Podcast Host]

Never listen. Never listen.

[Mike Lazaro]

And I think what we've realized now, that our youngest is 18, is that they do model our behavior. So they look at how you're acting, how are you treating people? How are you working? Are you working out? Are you eating well? All that stuff kind of goes into who they are. And so fast forward, they have witnessed how hard we worked, how we treat people, which is we think in a good way. Ethics Foundation.

[Cass Lazaro]

Yes, they modeled. And then what's been interesting is to see the two college kids, the boys, our sons, say, hey, mom, can you just see if you like this response to an email to a potential job offer? And it's one of our tones. It's like hearing our words in theirs. And Mike's 100% right that they model you. It's gonna be a culmination of many years. I always say, my kids know this. There's very little ROI on kids, right? But you get it.

[Mike Lazaro]

23 years, 23 years of work and.

[Podcast Host]

Investors, such business people.

[Cass Lazaro]

It's terrible, you know, and you're waiting, but then you get these little moments. It's kind of like bringing up kids is kind of like golf.

[Podcast Host]

Oh, you're gonna make a golf analogy? It's gonna be totally lost on me. Andy's a big golfer. I know nothing. I wanna dig into that for a second because I wasn't a founder like you, but I had crazy turnaround, shoveled a lot. The building's on fire. I'm your person, right? I run into fire, which meant, like, I was always on. Right? You know, there's probably A picture of me that my, you know, with my firstborn, with the phone to my ear or whatever they like to sort of use as a meme these days about me. But there was definitely moments that things were complicated at the home front and complicated, I mean, always complicated at the work front, where I thought to myself, okay, should I make a different decision? Should I not work for a period of time? Like, where was the message?

[Mike Lazaro]

So I think it culminated when we sold the company, the last one, when we sold Buddy Media. It should have been the greatest day, week of our life. We sold for close for a billion dollars. It's like life changing money. It's like after all these years and we were relatively numb. We had two of the three kids not doing well, One who was goofing off at school, who'd never goofed off, the other who's having some medical issues. And as I said earlier, I was 30 pounds overweight. My cardiologist said, if I don't, like, get that in the water, these are the messy parts, you're gonna die. We had offices in London and Singapore and all over the US we weren't very connected.

[Cass Lazaro]

I was getting migraines probably five days a week. And literally at one point a doctor's like, you have to sleep. I'm like, I literally can't sleep. Can't sleep. So, like, you carry the stress. Yeah. So there's so many messy parts. It took me a full year to get my nervous system back after we sold the company, like, to get it, like, recalibrated.

[Mike Lazaro]

And that's what I mean at the end of the day, like, why we wanted to write this book is it's not just about how to excel at work, but it's how do you do it and create a life worth living?

[Podcast Host]

Because what does that mean, a life.

[Mike Lazaro]

Worth living where you have relationships that matter, where you have health that lets you do stuff, which we lost a lot of relationships, and we weren't in good health. And we were able to prioritize and figure out a way which we share in the book. It's being able to have some freedom to do stuff that you want to do. So our first 50 years is about earning reputations. We graduated, earned degrees, money. Now it's all about impact. We have a duty now. We've made some money, have some knowledge to kind of share and help. And so to us, that's life. Like, that's a life worth living. Like being able to impact other people. I think if we were miserable and had all this money, we'd be like, why? Like, why did we do it? Right? And so part of, like, our discussions with entrepreneurs is like, if you, like, your spouse, plan the date night. If you, like your friends, plan a way to see them at least a quarter.

[Podcast Host]

It's super hard to see your friends. It is. Unless they're your work friends.

[Mike Lazaro]

I said a quarter. Like, I said once a quarter. Like, do, like guys night. You know, girls night. Like, and if you don't prioritize things, they will decay and you'll be left wondering. And it's like you just didn't put in the effort.

[Cass Lazaro]

And we didn't have a lot of friends. You just said it like we had. We had friends in the company, but there's still always a wall there. And we certainly didn't have any friends at any of the schools.

[Podcast Host]

Because I remember you having a story where you said you went to the school and you were like, wait, I don't know who my kids.

[Cass Lazaro]

We didn't. We had sold the company and they were about to take over. So this is September 2012, and we got to the assembly, and it occurred to us, when the principal said, hey, take your child. Each teacher will have a flag. Like a pole with a flag on it, and it'll say like, 3D or something like that, or like, you know, classroom 4A, and just take your child up to your teacher. I looked at him and he's like, looking at me. And I'm like, I got the same email you did, which one's our teacher? And then we just kind of shopped them around.

[Mike Lazaro]

I mean, we were checked out with the kids because we were just.

[Podcast Host]

But who was raising them?

[Cass Lazaro]

Well, we had an incredible babysitter, and her name was Jessica. And then we had that babysitter on Wednesday and Saturday nights named Stephanie. That was her niece. And, you know, we didn't go out on the weekends other than with ourselves. And if sometimes somebody wanted to come with us, we spent it all with the kids. Right. That was our only time with them.

[Podcast Host]

I mean, I had my weekday babysitter and my weekend babysitter.

[Cass Lazaro]

Yeah.

[Podcast Host]

I mean, partly. Cause sometimes I just needed two hours to myself.

[Cass Lazaro]

What I will tell you is that at least from my point of view, being a woman, that all three of my kids think I'm very strong, very dedicated, and I show up when I need to. So their view of me is one of, like, a very strong woman, which I think I wanted to show them anyways. And it's hard to talk through that. You gotta lead by example.

[Podcast Host]

Well, and I think for me, like, having financial independence was a thing.

[Cass Lazaro]

Oh, there's no doubt.

[Podcast Host]

Right? So that was a driver for me for sure.

[Cass Lazaro]

Definitely a driver for me. Me as well.

[Podcast Host]

For me also, it was like, I knew I wasn't going to be really. Like, if I'd stayed at home, I would have just made them nuts. You know, I would have organized everything. I would have been in everything.

[Cass Lazaro]

It's harder to be a parent.

[Podcast Host]

So hard.

[Cass Lazaro]

I mean, definitely a good parent. Than working. There's no doubt.

[Podcast Host]

So it sounds like you guys are also lifelong learners.

[Cass Lazaro]

Yeah, I. I would definitely agree with that 100%.

[Podcast Host]

And so what are you learning now?

[Mike Lazaro]

We're learning how to sell books.

[Podcast Host]

How's that going? Cause it's hard.

[Mike Lazaro]

So people ask us all the time. They're like, why are you doing this? We see you on social media, we see you flying and speaking at events.

[Podcast Host]

We see, like, because you don't need to do this.

[Mike Lazaro]

We don't. But part of it, we ask ourselves why? And we're doing it because we love challenges, we love to suffer.

[Podcast Host]

Like, truly, I feel like I'm doing that with the podcast. So that's fascinating.

[Mike Lazaro]

It's a similar thing, right? Because you can't fake it. You can't fake it. And so. And we said, if we're going to write a book, we're going to sell it. We want people to. Not we're giving away all the money to cycle for survival, but we want people to read it.

[Podcast Host]

Why is the point of writing it if nobody reads it?

[Mike Lazaro]

It's not like an ego thing where it's just like, I'm going to say, I'm an author. I want to get these into people's hands.

[Cass Lazaro]

And this has taken me a while to get Mike here to actually want to write it.

[Podcast Host]

Why not?

[Mike Lazaro]

It's hard. And I was like, the selling parts. The industry is. No one likes their publisher. Everyone says it's ridiculously hard. And I think my vision for how we're gonna impact looked more like a podcast and other stuff. But when we talked about it was on her bucket list. I also didn't wanna write a book. Cause I'm like, the writer. So it's like, oh, no, we're going.

[Cass Lazaro]

Back to journalism stuff.

[Mike Lazaro]

Us writing a book is like, I'll come up with some ideas and you.

[Cass Lazaro]

Kind of write it.

[Podcast Host]

No, no, no.

[Cass Lazaro]

I really did scaffold the book.

[Mike Lazaro]

She did more than half of it. She remembered everything.

[Podcast Host]

You're partners.

[Mike Lazaro]

So it turned out to be great.

[Cass Lazaro]

He just happen Incredible with words.

[Mike Lazaro]

Yes. And she's not incredible at editing, which.

[Cass Lazaro]

Created a lot of. I am great at editing, which created a lot of. You didn't like how I edited it?

[Mike Lazaro]

How she edits is. I'd write a chapter, she'd be like, no, thanks. She's like, I don't think it's. I don't like it.

[Podcast Host]

Okay. Do you have notes?

[Mike Lazaro]

Like how it's just not doing anything for you?

[Cass Lazaro]

It doesn't say what I wanted to say.

[Podcast Host]

What was your goal in writing the book?

[Cass Lazaro]

To help as many entrepreneurs as possible. To give back to everyone. I just felt like, why am I saying the same messages over and over again five to ten times a week to all the entrepreneurs? Why can't I say it more?

[Podcast Host]

So it's a way of scaling.

[Mike Lazaro]

Yeah.

[Cass Lazaro]

It's amplifying our impact and our messages and our giving.

[Mike Lazaro]

Like, what we realized very early on is the more we give, the more we get.

[Podcast Host]

You know, that I totally believe in.

[Mike Lazaro]

We both are friends with Gary Vaynerchuk, Chuck. He shows up to our office and he needs an. This is before he's Gary. Right? He didn't have money for his own office.

[Podcast Host]

Yeah. He took over your conference room and.

[Mike Lazaro]

He said, kai, have your conference room. Like, no problem for a day, for a meeting. For what? He's like, oh, no, I need it for my office. Him, AJ and like four goofballs who I now know, Marcus and these guys, and they grew a half a billion dollar business from that conference room is where it started. And that was just a little give. And then fast forward. We're in his office doing a three hour live, you know, National Shovel Day. We made up a holiday together and we.

[Podcast Host]

Of course you did.

[Mike Lazaro]

Sold a ton of books. And part of this is the same thing. If we just give it, like, put it out there, I think it'll be good for deal flow. It'll be good for our speaking. Like, we speak and we kind of now get paid, which is weird that people pay us to do that and whatever we want to do. We don't have to tell these lessons. Like, everyone we invest in now, we're like, here, like, don't ask me a question.

[Podcast Host]

It's like a shortcut.

[Mike Lazaro]

Yeah, don't ask me a question until you read this and then you'll know.

[Cass Lazaro]

Let's talk about it.

[Mike Lazaro]

You'll have our system. You'll have our 50 cheat codes that helped us create businesses and a life. And you'll have questions. It's only like 250 pages whatever. But this is really what we kept saying over and over, like how to pivot, how to like choose a co founder, you know, the best way to raise money, all these things.

[Podcast Host]

Let me pivot the conversation for a second. You talk a lot about Marc Benioff and how he was really focused. Is focused on philanthropy. You're sort of now in another chapter, like you've written this book. You're giving back in this way. You're still working with founders. Do you see a different hill to climb that may be slightly different?

[Mike Lazaro]

We're definitely going to do different stuff. We think venture capital is broken for a lot of different reasons. We're not out there raising billion dollar funds. We've done great as investors and we're happy we did it. We've started buying cash flow businesses, which is a new thing for us.

[Podcast Host]

I mean media business, staffing firm. Okay.

[Mike Lazaro]

You been around for 25 years. We love healthcare.

[Podcast Host]

Why?

[Mike Lazaro]

Because there's a lot of money in it. We learned very early to put yourself as a business in front of big streams of money. Like it makes it easier if there's a line.

[Cass Lazaro]

So the innovation that's coming with AI is going to be fantastic.

[Mike Lazaro]

We haven't seen the digital transformation in healthcare like we've seen in finance and other places, but these are businesses that are, are very stable.

[Cass Lazaro]

We also like boring businesses. Give us a lawn care business. We love all that.

[Podcast Host]

Ever think about doing something just totally different?

[Mike Lazaro]

I think what we realize is that like many entrepreneurs, we find our purpose in building, building companies, creating. And it's where we find our misery and your joy.

[Cass Lazaro]

Yes.

[Mike Lazaro]

And what was interesting is not only was I miserable as a painter, we were just in LA talking to a group called Chapter X which is post exit founders. And one of them who sold a business for 1.1 billion and took hundreds of millions off the table, basically was very raw and said I would give all the money back to have my company.

[Podcast Host]

Literally. This is the conversation I heard at Collective Features. Like, same thing. Took a billion dollars off the table and said, I've never been more miserable.

[Mike Lazaro]

It's probably the same person, but it's very nameless. It's a universal. And I felt it as a painter. Like, I'm not doing what I was put on the earth to do. And we had a company we invested in go public this week and we are more happy for those.

[Podcast Host]

Are you going to tell them what it is?

[Mike Lazaro]

A company called Etoro. And I'm happier for those founders than we were when we sold Buddy Media. Because we were miserable. Seeing a founder become a billionaire is so awesome. Someone who you've known for 12 years, who've grown a business from nothing, and that. That is the sport we play. It is what we do. We've also realized that we don't have to reinvent the wheel for every business.

[Podcast Host]

Can I ask you a question? One of the things that struck me as I was in this conversation yesterday was whether now that we see the world slightly more broken in ways than maybe when we were growing up, I don't know. I always wonder if it's just cyclical.

[Mike Lazaro]

Oh, no, it's not. This is crazy times.

[Podcast Host]

Okay? So, I mean, where there's things that are broken, where you think to yourself, like, I have these skills. I'm very good at these skills. Should I apply them someplace else? Like, this morning, I heard the mayor of Denver, and I was like, what's his background? He was a teacher. Did you ever think, like, I should take my skills and be like, how should I fix the city? Like, a different problem altogether?

[Mike Lazaro]

I have thought to myself, how do I take Cass's skills and fix everything?

[Podcast Host]

But you're gonna be running for mayor.

[Mike Lazaro]

My skills don't. Mine don't apply to a lot of the problems in the world. Like, no one needs a salesperson or someone with vision or someone who could just, like, raise a lot of money.

[Cass Lazaro]

I mean, I'm kind of thinking about.

[Mike Lazaro]

This is an incredible operator.

[Cass Lazaro]

Some very, very important roles that could take a vision and raising money.

[Mike Lazaro]

Cass is an incredible operator. Right.

[Podcast Host]

Like using your operating skills in other spaces.

[Cass Lazaro]

I have. I mean, like, you know, when Mike was painting, I was on several community boards.

[Podcast Host]

Right, exactly.

[Cass Lazaro]

And I was helping solve lots of different issues doing that. Stephen Gaynor, board, Riverdale board, definitely school boards. I was in the community doing things like that. And I think, was that satisfying? It was, and it wasn't. And I'll tell you it was, because I love giving back to the community which raises our kids. I like being helpful there. And I didn't feel like I was reaching enough people, so it was like smaller problems. And my currency is just being able to help someone.

[Podcast Host]

Okay, so I have one question for you, and then we're gonna do rapid fire.

[Cass Lazaro]

Okay.

[Podcast Host]

I remember a line in the book where you talked about you were really excited that you came of age in the era of Facebook and Twitter, but now as par and sort of in the world that we live in, we also sort of understand, like, the genie that came out of the bottle that we never can put back in do you have misgivings about that or thoughts about that? Because we're sort of seeing another iteration with AI coming up that, you know, I think about the World Wide Web, when that's what we called it.

[Mike Lazaro]

So, yes, I mean, we have thought a lot about that. We helped invent a lot of the stuff that Cambridge Analytica use to impact the election. And I think, think when we write about it, we're very glad we came of age during that time. It was a huge business opportunity. It was full of optimism and fun.

[Cass Lazaro]

It was fun and fun.

[Mike Lazaro]

And we really believed that when you connect the world through these platforms, people had access to education and communication and media, and it was going to help democracy. And we didn't know that these platforms were only going to optimize for engagement. Negative stuff is more engaging and fast forward. They have destroyed democracy and people's mental health, especially kids. And I was very vocal in talking to leadership, really more after I left, saying, listen, it's easy what to do. You have to announce that you're not optimizing just for shareholder value, but wider stakeholder value, and you're going to focus on attacking these issues. And you can't put engagement as the North Star. And they never did.

[Podcast Host]

Right. Because it's growth at any cost.

[Mike Lazaro]

And it only got worse as new owners came into these platforms and changed the names. And where we are is negativity is what drives. We know that if we wanted to attack people, we could have a much larger social following. It's just not who we are.

[Podcast Host]

Yeah, well, I can relate to that. Okay, so I didn't mean to. To bring us to a downer, but it does seem like it is a bit of the messy part that we've.

[Mike Lazaro]

All sort of lived through.

[Podcast Host]

Rapid fire questions you can both answer. You guys ready? Yeah. Your favorite karaoke song or walk on music?

[Mike Lazaro]

Mine is, and I'm happy to sing it.

[Podcast Host]

Say you, say me, by all means, Please do not.

[Mike Lazaro]

I'm not. Say you, say me by Lionel Richie.

[Podcast Host]

Wow, not a fish song.

[Cass Lazaro]

No, exactly.

[Mike Lazaro]

This doesn't go down well at parties.

[Cass Lazaro]

Let's just say that in your eye is Peter Gabriel.

[Podcast Host]

Oh, I love Peter Gabriel. And so. Okay. A food you'd bring to a potluck?

[Mike Lazaro]

The food I always bring is marinated flank steak. And the marination that I use is Worcestershire sauce. Is that how you say it? Dijon? A little honey. Salt and pepper. Garlic. A little garlic.

[Podcast Host]

Nice.

[Cass Lazaro]

I'm gonna go right down to what I was born to do, which is take sour cream. And Lipton onion soup mix. Stir it together and bring some Fritos.

[Podcast Host]

Okay. That's amazing. That's such a working mom. Answ. Um, Alt career.

[Mike Lazaro]

I thought I was going to be a journalist. Political journalist.

[Podcast Host]

Yeah. I thought I'd be a foreign correspondent.

[Cass Lazaro]

FBI or CIA?

[Podcast Host]

FBI or CIA. Love it. What are you listening to, reading or watching?

[Mike Lazaro]

So the Tell by Amy Griffin, who I cannot recommend. Enough.

[Podcast Host]

Read the galley.

[Mike Lazaro]

I just finished.

[Podcast Host]

It takes a lot of vulnerability to tell that story.

[Mike Lazaro]

Just an incredible story. Incredible read.

[Podcast Host]

Oh, by the way, and an amazing leaning into selling a book. Book.

[Cass Lazaro]

Yeah.

[Podcast Host]

I mean, she's a master class.

[Cass Lazaro]

Yeah.

[Mike Lazaro]

Yes. But just, you know, she went through a journey to be able to birth that book. Obviously, a lifetime of, you know, I'm not going to ruin it, but I think every person should read it, especially men.

[Podcast Host]

It's hard not to respond to the marketing piece of that. But anyway. Yeah.

[Mike Lazaro]

No, I agree with you on that.

[Cass Lazaro]

Yeah. I just finished watching Dying for Sex. Sorry, Mike. I know you didn't want me to watch it without you.

[Mike Lazaro]

I'm just finished living dying for sex.

[Cass Lazaro]

And I thought it was just so well done and raw and beautiful and even though there's dying in it, it was. It was amazing.

[Mike Lazaro]

When did you.

[Podcast Host]

When you were.

[Cass Lazaro]

You're on golf or something?

[Podcast Host]

I don't know. When you were. What's your handicap?

[Mike Lazaro]

I'm a five handicap. Oh.

[Podcast Host]

Well, he's not competitive enough to get to the one. Okay. Something surprising that some, you know, people have worked with you or known you would want to learn about you.

[Mike Lazaro]

I think that. And this hit me yesterday, I was talking to someone else about Cass and I started crying. I started crying.

[Cass Lazaro]

I got really emotional.

[Podcast Host]

Are you a crier?

[Cass Lazaro]

He's a crier.

[Mike Lazaro]

So I'm a crier. I'm actually very emotional.

[Podcast Host]

It's totally messy and I love it.

[Mike Lazaro]

I don't love it or hate it. It's just who I am. It just happens. And Cass, you know, of course, we're like.

[Podcast Host]

I was like, wait, what's the story you told?

[Cass Lazaro]

Oh, no, no, no.

[Mike Lazaro]

Well, I'm talking about, like, how lucky I was. I am. I don't want to get into it again. You're just trying to get into.

[Podcast Host]

It's amazing.

[Cass Lazaro]

We're gonna be like Barbara Bark.

[Mike Lazaro]

But I was talking about Cass and how lucky and how lucky we got. But really, I got. So she sees me welling up. She's like, oh, here he goes. He's gonna cry. So it's like, can't you just let it go like, let me cry in silence and try to hide it.

[Podcast Host]

You two clearly like each other.

[Cass Lazaro]

It's great.

[Mike Lazaro]

She's like jabbing me. She's like ice queen over here.

[Cass Lazaro]

You know, something that people wouldn't know is I love fly fishing. I love it.

[Mike Lazaro]

She's really good at it. Also.

[Podcast Host]

No. Okay. We know this about her. If she does something, she only does it to one.

[Mike Lazaro]

She did it when she wasn't good. She's worked on it.

[Cass Lazaro]

She's very therapeutic. And so I think as an operator, when you're constantly thinking about 15 things at a time and going to sleep is very hard for me, I need two hours of shutdown time before my mind can actually go to sleep. Yeah. So it is. It's like that micro focusing. That's what I love.

[Podcast Host]

So we close with one piece of advice. One piece of advice you'd each like to leave the viewers, listeners with.

[Mike Lazaro]

The most important advice that I got from Marc Benioff, which sticks with me today, is just do the right thing. Regardless what the contract says or what the social pressure or investors say, do the right thing and things will work out. And I never really thought about it, but I really believe in that now. Like, just do what's right, and it's just an easier way to live life.

[Cass Lazaro]

Be radically transparent with everything you do. There's absolutely no reason to have distance between people in a company. Just be yourself. Tell everything good, bad, and the ugly well.

[Podcast Host]

And that's actually the whole point of the messy parts. We're going to talk about the good, bad, and the ugly. So I can't thank you both enough. So much for making time to come on and talk to everybody and share all the amazing stories and the mess.

[Cass Lazaro]

Thanks for having us.