Latest / Success Story with Scott Clary / Mike & Kass Lazerow - From Zero to $745M | The Simple Truth About Growth

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Mike & Kass Lazerow - From Zero to $745M | The Simple Truth About Growth · Success Story with Scott Clary

• 0:00
  There's nothing worse than being an entrepreneur and it's awesome. There's nothing better.
• 0:03
  Best entrepreneurs just love to suffer. When I look at the where people find their purpose,
• 0:08
  where they find their passion, it's an entrepreneurship. They're not just partners in life,
• 0:12
  they're partners in ambition, strategy, and growth. Mike and Cass are the duo behind one of the
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  fastest growing coaching brands in business and lifestyle mastery. You were in a marriage
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  dating whatever it is. You have to have the big conversations. Why are you doing this? You just have
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  to both know why someone's doing this. Co-fronters have the same morals and values. I think are
• 0:32
  real winners. If you want to build a real venture company, you have to have the opportunity to
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  reach billions of people. Together, they've helped thousands turn confusion into clarity and ideas
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  into thriving, predictable income. Their partnership isn't just about success, it's about the journey,
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  the grind, and the transformation that happens when two minds commit to excellence together.
• 0:53
  If you're brutally and radically honest with everybody, including yourself, pivoting is part
• 0:59
  of every entrepreneur's life. If you can constantly explain what you're doing to the teams around you,
• 1:04
  then those pivots become easier and easier. If you do the right thing every day, we
• 1:09
  month quarter, you'll be successful in some way. Money does not come with that. Line something
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  that you really are passionate about and put all of your energy behind that.
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  So Mike, you write that entrepreneurship is awful and awesome, suffering that you wouldn't
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  create for anything. So help me understand why anybody would choose this life.
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  There's nothing worse than being an entrepreneur. Nothing. You get up, you get hit in the face,
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  things go bad, clients cancel, employees go rogue, and it's awesome. There's nothing better.
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  It's why the book is shoveling shit, a love story. It's our love story to each other, but also to
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  entrepreneurs. And the best entrepreneurs just love to suffer. They realize in order to get to where
• 1:59
  they want to do, where they want to go, it's just going to be full of obstacles and shit hit in the
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  fan. And so when I look at the where people find their purpose, where they find their passion,
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  it's in entrepreneurship. So if you talk to an entrepreneur, you say, how's it going? Oh, I'm
• 2:17
  killing it. Then you're like, well, are you really like tell me a little bit more? And it's like, well,
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  no, like I'm stressed. I'm running out of money. I'm doing all this stuff that's not fun. But at the
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  end of the day, you ask, well, would you rather do something else? Would you rather have a job?
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  Would you rather have security? No way. I'm doing exactly what I want to do. And it's miserable.
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  And so we tried to capture that in this idea of shoveling shit, a love story.
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  Did either of you have any idea what you were getting yourselves into? I don't think anybody does,
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  really. You mean becoming an entrepreneur? Yeah, becoming a non-no with yourselves? No, no, no.
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  Maybe that's a whole other part that I'm kidding, but just becoming entrepreneurs because you
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  started working together before you even were married, correct? So you were working together 30
• 3:03
  years married for 25. So something was working out in the business that you said, okay,
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  let's not only be business partners, let's be light partners. But what was that sort of inflection
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  point in when you were dating when you said, let's build a business together? So I had this idea
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  to build golf.com. I was in a kind of recreational golfer, no money, like didn't belong to a private
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  course. And back then, you had to go to these public courses and go to the same machine to
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  enter your USGA handicap. So when I had this idea, there was no one else I wanted to do it with,
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  other than Mike, because I would come home, even from the day job that I had, which was at a
• 3:45
  big agency. And I would ask him questions about like business models and monetization. So he would
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  come home from his job, he actually was running his company, you are and talk to me about like
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  operations and execution. So I think we were lucky that we figured out that we have no overlapping
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  skills, like none. And that's a good thing. It's really important when you're co-founders because
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  you don't micromanage each other. You don't have this like paralysis of decisions. And it just
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  was a natural fit. So obviously I had a recruiting advantage. We were living together. So I just
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  literally said to him, when are you coming on board, when you coming on board? And then finally he
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  did and things went from there. We can talk about business strategy all day, but I think that
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  what's even more important is figuring out like when you build a business with a partner,
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  what are the things that you have to think about so that that doesn't ruin the relationship?
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  We definitely have to have the uncomfortable conversations. Just like you were in a marriage
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  dating, whatever it is, you have to have the big conversations. Why are you doing this? And it
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  doesn't mean that the answers have to be the exact same. You just have to both know why someone's
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  doing this, right? So that there's no resentment that gets built up later on. I always ask the
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  question like, how do you, like what refills your cup? I always want to see founders who know the
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  emotional side of their co-founder so that if they decide I'm going to play golf one day,
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  they know A that they are at their end of the line here and they're getting really stressed out
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  and B, they're not resentful. So uncomfortable conversations. You got to have the same vision.
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  People who have that co-founders that have the same like morals and values, I think are really
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  winners. What do you have to watch out for when you're building with your spouse? Just so that you
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  don't, that you don't let it ruin everything. We think it's a superpower. And what's ironic to
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  us is people will say, I don't want to work with you, but let's have these three kids, right? And
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  kids are so much harder than companies. Primarily because you can't fire your kids. You can't pivot
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  your family into something else, right? And so if you can have first, we had a dog, it went well,
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  you know, cookie and Chicago. Baby steps, yeah. Baby steps. And then we had a business and then
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  it's like, okay, we like this. Let's start having kids. We were young. I was 22 and I met
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  Cass and we were very different, but we had the same foundation. We worked hard. We looked at work
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  as kind of a virtue. It was centerpiece of everything that we did. We had friends and family and
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  everything, but work was like really important. And so it was just felt so natural to do it. We
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  didn't overthink it. I think where you get into problems if you don't think about it enough,
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  or you overthink it and you try to overanalyze it. If it feels good, it usually will turn out well.
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  I'm not talking about good the first time you talk about it. Let it sit. Have conversations. How
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  hard do you want to work? Are you full time? Are you going to want to sell it or play the long game?
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  You know, what's your philosophy on investors? Do we want to bring on money? Do we want to
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  bootstrap it? All these are conversations that we outline in the book. You know, a chapter
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  called Saying I Do, which is a marriage. Once you get, you know, you can change markets. You can
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  fire employees. You can do a lot of stuff. What's really hard is changing co-founders. So make sure
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  that you spend the time early on to do it. And we protected our time as a couple by always having
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  date nights. So even when we had newborns, we had two date nights a week. And I remember in
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  the early days, because we had three kids under five, we were exhausted, and we were working, I don't
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  know, 12, 14 hour days. And even if we didn't go out, we would be there just trying to connect.
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  And I think that helps. I think there's a lot of entrepreneur couples out there that don't do
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  that. And you need to do it. And yes, you're still going to talk about some work stuff.
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  Because it probably will be the only time you're only meeting just the two of you. But everyone
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  always used to say, like, how do you work with them? Well, I never worked with him on a daily basis.
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  That's the key. Like I, so you knew what you were good at. Yes. And we outsource it. Yes, implicit
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  trust. You said that Mike shakes the trees and you pick up the mess. So I like that. I was really
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  true. Who did you? Who did you tell that to remember that? It was on one of the podcasts. It was
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  on one of the podcasts. But I love it. I like that. How do you identify? First of all, what does that
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  mean? But also how do you identify who's good at what? And again, this is talking about you as
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  a married couple, but also this is an important lesson for founders that are just founded with
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  somebody who they're obviously not married to. Right. So I think in those like beginning conversations,
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  when you're like, Oh, I have this idea. Do you want to come work together and do this? You have
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  to decide what you're going to own. And the best founders literally say, Okay, that's yours. This
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  is mine. And I'm never going to pick at it. Right. I'm going to not micromanage you. For Mike,
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  I always knew he was great at sales, client facing, fundraising, money, business models, vision.
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  And it happened to be everything that I'm not good at. We overlap a little bit in marketing,
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  but anything that has to do with a daily grind of like hiring people, operations, finance,
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  accounting, marketing, legal, like I just pick it up and I run. She's an incredible operator.
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  Now I was just going to ask if you agree with that statement. No, 100%. And we've seen it. We've
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  done over 100 investments, primarily tech, but also like liquid death and you know, some CPG
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  companies and she's just the best operator I've ever seen. And when I say operator, it's not only
• 9:49
  how she operates the business and executes the plan, but it's how she lays people off. People
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  get laid off by cast and it's like the best day of their life. Like literally she tells them
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  here your strengths, here your weaknesses, here's where you fell short. Here's why you're not a fit
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  for us, but where I think you should go. And it's kind of like, man, I just got like a life
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  direction. I go to lay people off and they get a raise and more money, right? Like it's just,
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  I'm like conflicted verse. So it's like we've settled into something that works for us, but it
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  really is the model for all businesses that you should bring someone on board who one plus one
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  equals five, right? That you're both moving in the same direction where we've seen a lot of
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  issues is if you have two technical co-founders arguing about stuff that doesn't matter, tech stacks
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  and code that are so in the weeds and they both are the experts and they both have the complementary
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  yes skill sets. It took us a while. So I would kind of chime in on operations and after like a few
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  years and losing like every argument, I'm like, okay, I get it. Like as an entrepreneur, especially
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  as kind of a man, we're not very self-aware. Like we're very optimistic. We don't always listen
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  well. We're not always present. I don't want to like, it's not just a female male thing, but I tend
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  to see men are little less self-aware, less open to talking about emotions and over communicating.
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  And so after a few years, I was like, yeah, I am kind of an asshole. Like I got to like slow roll
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  this. I got to be present. I can't. I got to put my ego aside. And I think that's why the first
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  business was successful. We sold it for 25 million after a few ups and downs. But why we really
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  gotten a groove by the time Buddy Media came where we went from zero to hundreds of employees, 50
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  million annual recurring revenue and basically three years because we had, you know, we were in
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  our lanes. So when you started Buddy Media, you've already sort of figured out how to work together
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  at this point, right? So after sort of going through golf.com, 25 million dollar exit with that,
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  you're starting Buddy Media, like sort of what's the what's the game plan for for day zero?
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  So the things that you wish that you had known when you're starting golf.com that would be useful
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  for you, but also use for founders that are just starting out. So golf.com was a relatively small
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  market. So if you look at the golf space, yeah, it's like 80 billion dollars. But like most of it's
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  like travel and owning a golf course. So golf media was really small. I saw social media. I say I
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  because a lot of the vision comes from me like the areas we attack, you know, I've been one of my
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  superpowers have been getting there early, whether it's internet, social, you know, AI, you know,
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  whatever we're doing. And so, you know, at this point, Cass is having our third kid. She's in the hospital,
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  you know, delivering a C section. And which means just means I'm it's an operation. I'm on my
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  blackberry. And Facebook launches. And I just thought it was a huge thing for the internet.
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  Internet up to that time was a one person player game, right? You would shop search for information.
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  There wasn't really a social layer. I saw this as the opening of the social layer. And so Facebook
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  Mark Zuckerberg on stage. And this was May 24, 2008. Yeah, it's his F8 event announces their platform,
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  which basically invites developers to build social applications out of this game Zingha and game
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  companies, right? You could play games against friends first just games against yourself solitaire.
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  And I just knew it was going to be a huge market. And so the biggest lesson we learned
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  from the early businesses is focus on a big market. Focus on something that's like if you want to build
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  a real venture company, you have to have the opportunity to reach billions of people to sell it,
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  you know, to tens of thousands of companies. And so we picked the right market and we got lucky.
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  That's really was the lesson there. How much? Okay. So how much was luck? Because everybody who's
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  listening to this is going to say, yeah, for sure, pick a big market. But then you have the blue
• 14:04
  ocean versus red ocean. Like, so when Mike picks things like any literally things like, okay,
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  this is where we're going. It's not like we didn't pivot five times, right? So if you think about
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  our business model, I think the other lesson is, can you pivot to survive, right? And do you have
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  the self awareness to know when things aren't going well? And you pull the plug, right? Because
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  a lot of entrepreneurs they dig in when things aren't going well. And then they try to convince
• 14:31
  themselves and they think that they tell them so stories like, oh, the board, I sold this idea
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  on, you know, to the board, like I can't change all the employees are going to think I'm a fruit
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  loop if I change now. And the key is that, you know, if you're if you're brutally and radically
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  honest with everybody, including yourself, pivoting is part of every entrepreneur's life period.
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  And so then if you can if you can constantly explain what you're doing to the teams around you,
• 15:02
  then those pivots become easier and easier. So yes, like we jumped at, you know, this social,
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  you know, industry, whatever that was going to be. But we pivoted until we could find recurring
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  revenue. You pivoted until you could find recurring revenue. Okay. So before so you did a four plus
• 15:22
  pivots, um, we started with something called ace bucks. I can't even say it with a straight face.
• 15:26
  It's like the worst idea ever. But she didn't veto for the right. It was a bad idea. Nobody knew
• 15:32
  at the time. No, you just said, I had a baby literally that, you know, two days. Yeah. And then
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  you then you started the ace box. So you went from ace box to the building custom apps.
• 15:42
  ace box was so that you knew I want to it shows how much of a pivot you can actually have before
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  you become successful. So yeah, even the name of the company you, you know, we we sold to sales
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  force, basically the largest social media management system software that helped very large brands,
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  not out of the top 10 global marketers manage all their social media marketing paid earned owned
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  across Facebook and Twitter, which was called at the time YouTube Instagram. And it was a business
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  that was a software business. You never started out called buddy media, right? If you think
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  you're going to get there. So, you know, we launched this web wide currency ace box with the ideas
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  that you earn at playing different applications on Facebook and elsewhere. And you burn your points
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  or spend your money. That's how these things were as Mike's motto. Yeah. Then you could burn
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  for buying like iPods. And we had all these like different like, you know, it's kind of like
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  you're going to chuck each easy. Yeah, I know exactly what you're talking about. Yeah.
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  But just say that we're not economists like massive inflation. It didn't work. It was like stupid.
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  And then, you know, we started talking to brands. And I think one of the biggest things that we did
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  is we got the customer in the room. We said, listen, we got this ace box thing. And you know,
• 17:00
  you could let's take MX points and exchange them. And we're talking to all these companies.
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  I remember with MX in particular, they're like, that's like so stupid. However,
• 17:10
  we've heard about this Facebook thing. Can you help us? Right. And we're like, and you listen.
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  That's a business. That's key. Right. You gotta be able to listen. Okay. They're trying to figure it
• 17:19
  out. So we started with like custom apps. Like let's build an MX reward system on Facebook.
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  And eventually we're building the same types of apps for all all these companies. We productized it
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  in a drag and drop type, you know, no code development system that also let you post your content
• 17:38
  and run ads. It was a, I would say not a difficult decision for you and me. But I think our,
• 17:45
  the sales people were freaked out because they were making a ton of money on custom apps, right?
• 17:50
  They were going to L'Oreal and Unilever and everybody. So you had a business that was working?
• 17:54
  Yes. It was working. Yes. And we had probably two to three million in sales. And
• 18:02
  Mike's like, who's going to tell Jeff who we named co-founder or third co-founder at the end
• 18:07
  because he's just so great or head of sales? And Mike's like, not it. I'm like, okay.
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  And it was the one and only fight Jeff and I ever gotten to. And it was a screaming match because
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  he had so much on the table. He's like, you're going to ruin this business. You, you're,
• 18:22
  you're literally giving up. And I'm like, just watch. Just trust Mike. That's tough, though.
• 18:27
  That's very, I think that also, I think you were fortunate that, that it wasn't as big a deal
• 18:34
  for you because I feel like most founders, their ego and their identity is wrapped up in what
• 18:39
  they've built. And, and this is always the difficult conversation. And I, maybe you can help me
• 18:44
  have like a clear answer for this. There's always two conflicting schools of thought. It's like
• 18:49
  stick with it for an unreasonable amount of time until it works versus to quote Kevin and O'Leary,
• 18:55
  like when you take it behind the barn and shoot it, right? And, and how do you decide which one
• 19:00
  is the right answer? And I don't know. Well, for us, I mean, if you really look at what we did
• 19:06
  over the past 30 years, it's a series of pivots all the time. And those pivots could be many or big.
• 19:13
  And you, we always know now when something's not going well, not only from like customer feedback
• 19:19
  and data, but we can tell that our ego's talking to our gut, right? And your gut knows what's right.
• 19:28
  Your gut knows what's happening. So like Mike loves this V2 mom, you know, we learned it from
• 19:35
  Mark running off at Salesforce. It's the framework by which you can come up with a plan, know what
• 19:40
  your obstacles and measurements of success are. And so as entrepreneurs, we tell ourselves stories,
• 19:46
  right? We're really good at it because marketing is a big deal. That's how you get off the ground.
• 19:51
  And as Mike says, you have to have a big ego, right? To do that. But then you need to look back at
• 19:57
  something to say, okay, am I actually executing and did I hit the measurements of success
• 20:02
  that define what I've already sold to the board or to your investors? And I think that's where founders
• 20:11
  get caught. They're like, well, I did these projections, but they weren't real. And we're always
• 20:15
  kind of like, well, but I'm, but I'm kind of like, well, you said you're going to get 10 customers
• 20:21
  and you have zero. So what are your customers saying? That's, that's the friction right there. And so
• 20:27
  if you can get, you know, entrepreneurs to really focus on, here's my plan. This is what I'm going
• 20:33
  to execute for this quarter or this year. Make sure you also write down the success measurements
• 20:40
  because otherwise your brain's just going to keep saying to yourself, oh, this is working. This
• 20:44
  is working. We got it. We got to wait one more year. We're going to do this one more quarter.
• 20:48
  It's going to be great. Well, it's not if you look at those success metrics and that and V2 mom is
• 20:55
  just a way, it's a framework to figure out if it's working or not because when you're running
• 20:59
  at like two or three million dollars in top line, there's things working. But because you have a
• 21:04
  framework, you know that it's not working as well as it should be working. And also like when you,
• 21:08
  when we thought about like custom apps and we were going and doing this, I start to look at,
• 21:14
  okay, how many teams, how many people, how many resources do I start pairing per custom app?
• 21:21
  And so I start projecting out, wait a second, this makes no sense. Like we can't keep up economics.
• 21:28
  We're going to be an agency and that that's not really where our expertise is because we were
• 21:34
  getting people wanting, you know, very custom, brand oriented, you know, heavy graphic,
• 21:41
  you know, that kind of stuff. It just was in our expertise. It also points to like how to run
• 21:46
  businesses, I think. And I think we've gotten lost as just definitely in this country, but potentially
• 21:53
  everywhere else where a lot of young entrepreneurs think that their democracies, right? They want
• 21:57
  to get feedback and everyone has a vote, everyone has a voice. We believe in this benevolent
• 22:02
  dictatorship because no one has all of the information, you know, other than the founders,
• 22:09
  the people who are looking at everything, who see everything, who know everything, who know the
• 22:13
  investors, know the clients, know what people are working on. And so we would listen, but it was
• 22:20
  always our decision. So when we went to Japan, we said, we're doing this. It wasn't an effort to
• 22:27
  get him over. It's like, we're doing this. And here's why. And we will take responsibility if
• 22:33
  it works or not. So definitely on us, if it doesn't work. But here's why we think it makes sense
• 22:40
  because it's a more scalable business model and compensations everything. And so if you're doing
• 22:47
  two things and you have like this new development platform and custom apps and the salespeople
• 22:52
  make commission on both, but it's easier to sell the custom apps. They'll just sell custom apps.
• 22:58
  And so you have to take that out of their toolkit in order to kill the business. If you let them sell
• 23:04
  it, they'll sell it all day because they just want money, right? And it feels good to close deals.
• 23:09
  I mean, your background sales, my background sales, I love closing deals. And you always wanted
• 23:14
  to sell the easiest thing to close. Exactly. But like if you up level yourself, right, you have to focus.
• 23:21
  And it's what you've done so well with your company now, like your focus, hyper focus. You can do
• 23:26
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• 23:32
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  Scott. SCOTT at Hule.com slash Scott. Use my code, fill out the post checkout survey to help
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  for free, that's NetSuite.com slash Scott Clary. That's NetSuite.com slash Scott Clary. NetSuite.com slash
• 26:12
  Scott Clary. Bringing people on board for the journey is important too. So yes, you have to be a
• 26:17
  benevolent dictator and you know all the information. But sales is easy because sales is driven by
• 26:25
  compensation. So you could make the argument saying, okay, well, this is this is how much money
• 26:31
  you're going to make over here. And I'm going to make sure that you can sell it. But to bring
• 26:34
  everybody over who's not on board with a new vision or the new idea, when you have, you know,
• 26:38
  10, 5th, I don't know many people you had or maybe a few less for two, three million dollars,
• 26:42
  probably not 15 plus, but you had a few people in the organization.
• 26:47
  How do you get them on board with a new vision? Because this is this is investors. If it's not
• 26:53
  working, it's very easy to get them on board with a new vision. You say, if you want to return,
• 26:57
  we're going to go in this new direction. But how do you get everyone else on board?
• 27:00
  So we had this belief or maybe I came up with it that we should share everything with the
• 27:05
  employees that they were just like the board and investors. And every quarter we would have a
• 27:12
  quarterly all hands meeting, fly people in. When we were doing custom apps, I think we were
• 27:18
  growing to 30 people, which is why I said, like, this isn't working. We shouldn't have 30.
• 27:23
  A lot of people, 30 people, you know, like this was too much, too many people. So when we got up
• 27:29
  to even like 350 people, everyone was flying in. They were mandatory. And part of that was getting
• 27:36
  the leadership team to give a presentation to the employees as if they were the board. So
• 27:43
  here's the new logos. Here's who we didn't win. Here's the red accounts that we lost that
• 27:50
  churned, you know, from our head of client success. And you kind of go through that and you
• 27:56
  educate. We also gave out financials, right? And we showed everybody how we were doing. Good,
• 28:03
  bad, and ugly. And because we were truthful all the time, and we never, I never hid anything,
• 28:09
  like whenever, like because you can see it on people's faces, right? And that's what if you don't
• 28:15
  explain things, that's what builds the cracks and companies. And the reason why cracks are awful,
• 28:21
  it's not just because people jump ship. It's that when you have to make a big pivot, they won't
• 28:26
  follow you because they'll panic, right? So if you've always been constantly, you know, truthful and
• 28:34
  honest and shared everything, then when you have to do something difficult, they will believe and
• 28:40
  trust you and they will go along for the ride, especially not especially everybody but the sales
• 28:45
  people, because the sales people like you said, it's easy. You've spoken about creating a cult
• 28:51
  like culture, like a good version of a cult, and within buddy media, a positive cult. So this is
• 28:56
  sort of, this is leading into that conversation. How do you do that? Because I think that's also
• 29:01
  something that a lot, like listen, we're talking about different companies at different sizes for
• 29:06
  sure. But I think a lot of people have a hard time getting everybody on board, not just getting
• 29:12
  everybody on board, but getting everybody excited about what's going on in the company. So how do you
• 29:16
  build this, this cult like culture? I mean, it starts with rituals. It starts with like the very
• 29:22
  first touch points. So I, every time we hired someone, like we did a ton of personal research.
• 29:30
  Like what were their hobbies? What was everything? So when we came on board, we already knew them
• 29:35
  very well. And we made sure they were like a culture fit. And then it wasn't just like, oh, you're
• 29:42
  going to have like a lunch that day when you come on board. There was a whole program that I did
• 29:47
  across the company so that they would really be exposed to what was the purpose of their job
• 29:53
  and their impact. And I think again, you, you, you couple that with radical transparency
• 30:01
  and communication. And then you reward people and you make a big deal about it. And we never
• 30:08
  forgot to celebrate little wins. So if, if we had a little win, like the tech team released
• 30:15
  something, like I had balloons, I had cupcakes, you name it because it was a big deal. And we weren't
• 30:21
  just going to go past it, right? And we had, you know, if you got through a year with me and I
• 30:28
  didn't like fire you, we had you had the biggest trophy I could do, which was a custom bobblehead,
• 30:34
  which if you think about it, even when we were at the very young stage, it was like $400 at that
• 30:40
  point. You can get them a lot cheaper now. But like $400 gift to employee doesn't really scale if
• 30:46
  you think about it. But I wanted to show people that like you made it. You understand why this is
• 30:52
  so important. And you understand that we're always going to take care of you. And it was visual. I
• 30:56
  mean, it would be on their desk. And I think, you know, cast built the culture. I kind of
• 31:03
  participated and watched or do it. And looking back a few things that I'd recommend to others. One
• 31:10
  is like this idea of symbol and rituals. So like what are the symbols in your business, including
• 31:16
  your origin story, right? That people grasp onto what are the rituals, you know, like every religion,
• 31:23
  every like organization has these like, you know, a cadence of like whether it's holidays or meetings
• 31:30
  or get together. And the third is, you know, cults, like real cults that are like bad, right? You ask
• 31:38
  how do these like people join as like crazy, usually guy cult leader. And the reason is because
• 31:46
  it's friends recommending it to friends. You got to come here because it's transformed my life,
• 31:52
  not knowing they've been brainwashed, right? We always thought of that for the good, which is like,
• 31:57
  how do we get our employees to get their most talented friends? And there was our biggest
• 32:03
  growth year we added over 100 employees. The, you know, 70% of them came from referrals and,
• 32:11
  you know, employees, people, they won't recommend their friends if they aren't great, if they aren't
• 32:17
  easy to get along with. And they won't fit if they don't fit. And so it's, you know, when we talked
• 32:23
  about the culture we built, it quickly became in our mind, wow, we created this cult through
• 32:30
  rituals, symbols, recruitment. And we had like that year, I remember, we also had zero people
• 32:36
  leave in a whole year, which is amazing. And when we had this referral system, refer a buddy,
• 32:43
  right? You could make, I don't remember, it was like 1500 or 3000.
• 32:47
  That's the five grand. Yeah. But during the quarterly meetings, I would put up the leaderboard
• 32:52
  of which employee was referring the most. And so there's one employee who made more money recruiting,
• 32:59
  like engineers and friends, then salary, then salary. And we love that. That's healthy. That's
• 33:04
  very healthy. At the healthy set up. Mike, you said that there are three reasons companies fail,
• 33:08
  co-founders fight, they're not focused on the right thing or they run out of money.
• 33:12
  So obviously, that's usually talking about some of the investments that you've done in you,
• 33:17
  and what you decide to put money into or not. But I'm curious, which one of these were the,
• 33:23
  the came, that came the closest to killing buddy media out of those three things.
• 33:27
  So buddy media was, you know, the right company at the right time with the right team.
• 33:33
  And so that was a company that we pivoted, but we do we're in the right market, and we'd never
• 33:39
  doubted that we'd figured out. No, run out of money. No, run out of money, because by that point,
• 33:45
  you know, we're very lonely at golf.com. We didn't raise a lot of money. We had partners
• 33:52
  who we didn't necessarily choose. So like a New York head to New York hedge fund people, like
• 33:59
  one who owned, you know, a big Vegas casino, Phil Ruffin, who wasn't like the nicest guy,
• 34:06
  and I was like scared of him. I set out to put together the best investors I could,
• 34:11
  and I reached out to, you know, Mark Pinkis, who was doing Zinga. He was in the ecosystem.
• 34:17
  Peter Teal was one of our investors. He was on the board of Facebook. I thought that would
• 34:20
  be important. And Howard Linson and Roger Ehrenberg and all of these people who invested before we
• 34:26
  even launched. And so, you know, buddy media went really well. There were no co-founder issues,
• 34:35
  which was awesome. There were focus issues. We needed to figure out what to do. And by this time,
• 34:44
  we knew that we would need money. So we always raised money when we didn't have to. And so-
• 34:50
  And we also pivoted when we had money in the bank. So there wasn't like a really low moment when
• 34:57
  buddy media was operating as buddy media. Correct. But however, like we sold golf.com,
• 35:04
  the company we sold it to went bankrupt. We had to buy it back and then we grew it back. So
• 35:08
  we'd been through like some issues of like losing investor money, losing family members money.
• 35:14
  And we didn't want to make the mistake again. So we kind of, we raised 100 million. And
• 35:21
  eventually and people were like, why do you raise so much? Well, people seemed to employees
• 35:26
  want to get paid cash. Like, and we needed to build software. You have to invest before you
• 35:32
  reap it. But also, I think a big point here is you asked earlier about pivoting. We pivoted
• 35:38
  when we had money in the bank before it starts tanking. So it wasn't like this stressed out. Right.
• 35:43
  Like panic. Yeah. Decision. At what point? Okay. So there was a point where you had hundreds of
• 35:48
  employees. You had over a hundred million dollars raised. And then you hired a business coach
• 35:53
  named Tammy Jersey. Oh man. Oh man. Like, there was just a whole bunch of you getting involved in
• 35:58
  things that even even after this is after a hundred million raised after hundreds of employees.
• 36:06
  So what was going on at that point? Because you had already had early stages in your career
• 36:11
  understood that there was things that you should do and shouldn't do. I think I was ill prepared
• 36:16
  at the time, you know, in my early 30s now to run a global organization. And I was CEO and
• 36:24
  Cass was doing all the work as COO. We now had hundreds of employees. We had offices in Singapore
• 36:31
  in London all over the US. We had customers everywhere. We had to be there because that's where
• 36:37
  the customers were. And what I would learn is that your job as a CEO is like hire the right people
• 36:45
  focus the organization and let them do their work. Right. I would go and talk. I love engineers.
• 36:51
  So I would go down to the engineering floor. Right. We were in which I banned eventually. We were
• 36:56
  in Soho not far from where we are. It's actually like, you know, probably a quarter of a mile from
• 37:00
  here. And I just like shoot the shit. Right. Like, hey, what's up? Like, wouldn't it be cool? And
• 37:07
  all of a sudden one conversation, one conversation where I would say wouldn't it be cool is like
• 37:13
  10 engineers like stimming out and going to build something. And then the head of engineering
• 37:18
  Patrick Stokes getting word of this and being like a fucking asshole. Like he's coming down
• 37:23
  here. He's getting my team on focus. We've all these deliverables. It was happening on the sales
• 37:28
  side. You know, green lighting deals, you know, without talking to the head of sales. And basically,
• 37:34
  I wasn't listening. And I was kind of like a bowl in the china shop and Tammy Jersey cast brought
• 37:41
  in as a coach, as a coach, quote unquote. First thing she did was like interview, do a 360 review,
• 37:48
  right? Like interview all the people who I work with. And what came back was like, it was awful.
• 37:53
  I reread it. You know, it's part of the process of writing the book. And I was like, man, this is
• 37:57
  like, I would have fired this founder. Like if I were on the board, right? And it, it just showed
• 38:05
  how self at lack self awareness, really lack of confidence I had in the team. And you know,
• 38:13
  I wasn't at the same time. I didn't know how to handle this. You know, I had gained 40 pounds.
• 38:21
  I'm not working out. I'm not particularly pleasant at home. You know, I'm traveling to Singapore.
• 38:26
  Like 19 hour flights for like two meetings and coming back. So it's like, I wasn't great
• 38:33
  across the board. But this was like evidence. It's like, oh, I got to change or else.
• 38:38
  The lesson from that sort of period and body media, like when you're working with a new founder,
• 38:45
  how do you make sure they never get to that point? Or is that a, is that a person? Because like,
• 38:50
  I mean, you were successful in spite of that because you had the right people around you. But how
• 38:54
  do you make sure that like somebody was just starting out? Because I feel they don't start out
• 38:58
  micromanaging or losing themselves in the business. But I mean, we, we tend to get
• 39:05
  portfolio companies who want us as investors because they know that we're going to give them
• 39:10
  some of the cheat codes that we share in the book. And one of the biggest things that we tell
• 39:14
  them is radical transparency. Number one, make effort. I don't care if you're a remote company,
• 39:20
  then, then the founders travel. And you should have that as a line item for like expenses.
• 39:25
  So that your employees are actually getting face to face with you. And the third thing is that
• 39:32
  you need to develop in a lot of founders do this the wrong way, but a leadership team. And
• 39:38
  they it's not like 50 people. It's probably like six. And you have a weekly meeting that can't be
• 39:45
  missed unless there's a wedding or a funeral, like period. And that's where decisions are made.
• 39:51
  No where else are decisions made, not outside of that. So when I get wind of like mic going and
• 39:56
  hanging out, the next meeting and Patrick's upset, like we look at it as family, like this is a
• 40:02
  kitchen table, we're going to get everything out. Then we made a rule, Mike's not allowed to go
• 40:06
  down to the engineering floor. I know that sounds really ridiculous. But we also said, here's the
• 40:13
  product roadmap. We're never going to change it unless all six people in the room that represent
• 40:19
  sales, engineering, product and customer service. Because if we change it, even if someone didn't
• 40:27
  vote to change it, we all agreed on it and we know we all agreed on it and we can move forward.
• 40:32
  So we like to coach our companies to do it that way because it's such a great like succinct way
• 40:40
  of having the communication work and decisions so that you don't get to the point of someone's
• 40:46
  walking a hall and saying a great idea and rumors happen. And I would focus on like,
• 40:52
  it's a really good question because we've now seen so many founders, right? And so I'd never
• 40:58
  really thought about it like this, but as a founder, focus on your superpowers. So the reason why
• 41:04
  you raise money is you do something really well, whether you're an engineer, sales communicator,
• 41:09
  whatever it is. And then hire for everything else. And it's why kind of one of the best founders
• 41:15
  you've ever worked with is Mike Cesario at Liquid Death. He was a creative director for Gary
• 41:20
  Vaynerchuk and for some agencies. He's the best marketer we know and the most self-aware founder
• 41:28
  because he realized I'm a marketing guy. Like I don't know how to make like hundreds of millions
• 41:33
  of cans and supply chain and quality assurance and customer service. So he has built an incredible
• 41:40
  team that then lets him lean into his superpower. And I think everyone has those superpowers as
• 41:48
  entrepreneurs realize what they are and just be I'm okay with kind of offloading everything out.
• 41:55
  And when we invest in companies and I start doing the due diligence for teams, it's really like,
• 42:00
  am I going to get one of these founders who thinks he knows everything? She knows everything.
• 42:05
  I want to see founders who know what they don't know and be okay with that.
• 42:09
  Be okay with it and then say like, my next, if I get this money, I'm going to hire the people
• 42:14
  that can fill in my gaps. Let's have a conversation about health because
• 42:20
  something that has been important for me on this show at least is sort of highlight all while
• 42:25
  you're building and while you're trying to achieve some sort of success, right? People are usually
• 42:30
  trying to, you know, a lot of people listen to show our very entrepreneurial. And I don't want
• 42:35
  them to think that they can't sort of maintain not balance. I think balance is the wrong word.
• 42:41
  But I don't want the relationships to go to shit. I don't want their personal health to go to
• 42:46
  shit. I don't want all these other things to really degrade in pursuit of the goal.
• 42:52
  But I know it happens a lot and I know that I was I was listening to an interview with
• 42:57
  I hope this is correct and apology Sam if it's not but Sam par was talking about how when he
• 43:02
  was building the hustle, which he sold the hop spot. He had a really hard time finding time
• 43:07
  for like health and wellness and the gym. And I know that obviously you can talk about your story
• 43:14
  and I don't really know your your health story. So maybe go into that a little bit. But
• 43:21
  is there something you would do different? Is it just being cognizant of it? Is it something
• 43:25
  where for a period of your life, if you truly want to build something remarkable? I don't believe
• 43:29
  this but some people do. It's really hard to have balance. It's really hard to go to the gym
• 43:34
  and take care of yourself and make smart choices because you are all in obsessed with this this
• 43:39
  thing that is your baby that you're building. So tell some stories about your health as you were
• 43:44
  growing but also some lessons. So I am one of those people who believe you can only do one thing
• 43:49
  really great at a time. So it doesn't mean that everything else has to go to zero. It just means
• 43:55
  that the one thing you're concentrating is getting the majority of your focus and energy.
• 44:00
  And that even meant our kids just for the record for the moms out there. That was a little bit of
• 44:05
  a sacrifice. So when we were we were moving, we were we'd hit 50 million in, you know, ARR and
• 44:12
  three years, which was just unheard of. And we had so many different people like Mike said in offices.
• 44:19
  Mike was, as he said, 40 pounds overweight. I was having migraines after migraines. I've always
• 44:25
  suffered it but they were coming two, three times a week. I had gained 30 pounds and it was an
• 44:31
  undiagnosed thyroid issue which I didn't figure out for 10 years actually after that. And what we
• 44:38
  realized now at least I do is if you don't put something on your calendar, it's never going to
• 44:44
  happen. For instance, if I don't today, like I don't have a trainer today, if I don't put a
• 44:50
  workout inside the calendar, I'm going to tell myself stories about why I don't need to go workout.
• 44:57
  Right. And I'm going to say, well, you know what? I'm going to I'm going to say this. This
• 45:01
  meeting and this work I'm doing was a little bit more important than working out or meditating or
• 45:06
  taking a walk outside and getting sunlight. So we also tell all of our founders you have to put
• 45:12
  it on the calendar and it's okay to do it. So I look at wellness as kind of the fundamentals
• 45:19
  and then what you optimize from there. And I didn't understand this and it's hard. Like this is
• 45:27
  still a struggle for us. I've been on the road for the last two weeks. And I know it's a struggle
• 45:32
  for every entrepreneur who hasn't quite, quote unquote, made it, right? Who don't have resources.
• 45:38
  And so it for me, it came down to like drinking. So I stopped drinking because I was going to
• 45:45
  a lot of client meetings. We'd have steaks and like I'd get the we're in the enterprise software
• 45:50
  space. Everybody's drinking all the time. I wasn't sleeping because I felt like sleep was a weakness
• 45:56
  that, you know, if I'm asleep, there are other entrepreneurs up working. And so I didn't sleep
• 46:02
  that much. And that I think contributed to everything else, which is the third not eating well,
• 46:10
  right? So now I'm the time I was drinking. I wasn't sleeping. Big meals, grabbing stuff in
• 46:16
  airports or right, whatever it is. And it then came down to I didn't feel like working out,
• 46:25
  right? If you're like overweight, you're hungover. You're not eating well. You've no energy. Like,
• 46:29
  are you really going to work out little on have? And so I think you need to put on your calendar
• 46:37
  sleep, right? Like I am going to go to sleep at 10 o'clock tonight because I know I have a six
• 46:43
  a.m. flight, which means I'm leaving my place at 330, right? So you're kind of put it on exercise.
• 46:50
  I don't think you have to do it for two hours a day. But if you can find half an hour, 45 minutes,
• 46:56
  three days a week, it'll reset your brain. Like the neuroplasticity that comes from sweating and
• 47:01
  just kind of exerting yourself and you'll feel good. Do it first thing in the morning. You've
• 47:05
  accomplished something before other people wake up and then just make if you can better decisions
• 47:12
  about food, how whatever that means for you. Yeah, but it's like a flywheel to a degree. If you
• 47:16
  start with the sleep and the food and then we're even doing this book. So we did, you know,
• 47:22
  it was released in June. And I would say the quarter leading up to it, we were sacrificing health.
• 47:28
  I mean, I know we were because we were literally flying all over the place for the book. And
• 47:34
  we're very nervous that like a book about hard work would fail because we weren't working hard.
• 47:38
  Hard to ironic. So it was like, I'd be like, how'd you become New York Times best sellers? Like,
• 47:43
  oh, like there was no doubt that we were going to, you know, show up for everything that was going
• 47:48
  to sell 10 books that was going to get us over the top. But, you know, it was tough personally
• 47:56
  because we felt like we were back in the buddy media days. So I think that the issue is not that
• 48:02
  there's like imbalance. I think that if you, like you mentioned before, if you're building anything
• 48:06
  great, there's always going to be imbalance. Smarter choices sort of reduce the negative effects
• 48:11
  of the imbalance. Integration is what I guess. Yes. But it's also like, there has to be seasons of
• 48:16
  it. So if you go hard for three months, that's fine. If you're building something for 10 years,
• 48:21
  that can be a death sentence. If you don't take care of yourself for those 10 years. And that's
• 48:25
  what that was the lesson, the death sentence. Like Mike went after, you know, we were required and
• 48:31
  he started working at Salesforce for the urn out after you went to your doctor and he's like,
• 48:37
  literally, you're going to die. Like you're so unhealthy. So I have an artificial heart valve and
• 48:43
  I've had my heart rebuilt. And I'm my cardiologist. This is I think 2014. I'm now working hard at
• 48:49
  Salesforce. I'm chief strategy officer. I'm like, working probably just as hard because that's
• 48:55
  the kind of company that Salesforce is was definitely and still is. And my cardiologist said like,
• 49:02
  what's the point of like making all this money? I give three kids. Like you will die from if you
• 49:08
  continue on this. And I remember I then, you know, September 2014 called Rico Wesley who I've
• 49:15
  worked with. I'd already worked with as a trainer. And I'm like, I need you to keep me accountable.
• 49:22
  And we started three days a week. You know, he helped me with nutrition and eating and protein
• 49:28
  shakes. And it was also a dinner we had on if you remember this. We dinner with Gary, you know,
• 49:36
  very Chuck and Lizzy and he and there's just the four of us. And he just brought on Mike who's like
• 49:42
  would travel with them to work out and like would hand him like smoothies. And he's like, you've got
• 49:47
  and I'm and I remember he's like, you have to figure this out because you don't look good and you're
• 49:52
  going to like Gary was telling you this? Yeah. Yeah. To me this. And he goes, I have it figured out.
• 49:58
  I will help you like do it. And that's what got me on. I'm like, I need to write the same time in 2014.
• 50:05
  Yeah. It was exactly this time. And you have to there's something about being held accountable
• 50:12
  to things that you might feel are not necessary or like in the stack rank order of things at the bottom.
• 50:21
  And I don't know. I think it's because it's integration. So I think you're right that you have
• 50:25
  to minimize the negative effects of lack of sleep, lack of exercise and eating poorly and drinking
• 50:34
  and all that kind of stuff. But there's something to be said for like it's also a personality.
• 50:40
  Oh, 100% because you're telling me that your cardiologist is telling you this three years post
• 50:45
  acquisition at Salesforce is CSO. I get it. CSO Salesforce, whatever their market cap was at the time,
• 50:51
  very important job. But but I don't know if their whole C suite is having health concerns because
• 50:59
  it was probably you were putting 150, 200% of yourself into this job when you've done that important
• 51:04
  to the company. Like chief strategy officers like go talk to clients and wow them, right? Like you
• 51:10
  didn't have to be in that position. Yeah. Like Salesforce is not like I'm not the founder. I wasn't
• 51:16
  critical, right? But but this was going on. Let's just be clear. We see when when we see our founders
• 51:22
  suffering, I will step in and have a conversation about like mental wellbeing. Yeah, you have to.
• 51:29
  You have to and it's a big deal because it is lonely. I don't like being like, whoa is us like it's
• 51:35
  but it is. It's it's a lot of pressure and so that integration rule putting things on the calendar
• 51:41
  is a big deal. I also never had back to back to back whenever he has back to back meetings. It's
• 51:47
  a horrible day for him. You have to schedule breaks. Indeed is a success story partner. Now if
• 51:53
  you're hiring, indeed is all you need. Let me give you an example. If I needed to hire a new
• 51:56
  editor for this show, I'd go to indeed and be super specific. Not just can you edit audio,
• 52:01
  I'd say I need someone who's edited a conversational podcast for at least three years,
• 52:04
  gets our style and knows our software. Someone who's done this before and here's the thing with
• 52:08
  indeed sponsored jobs. I'd get people who fit that description. I'm not digging through resumes
• 52:12
  from people who've edited one YouTube video. I'm getting actual podcast editors who know what
• 52:16
  they're doing. People who've worked on shows like ours and can prove it. That's what makes a
• 52:20
  difference. You get people who actually are what you're looking for. According to indeed data,
• 52:24
  sponsored jobs posted directly on indeed are 90% more likely to report a higher than non-sponsored
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  and more results now with indeed sponsored jobs. And listeners of this show will get a 75-dollar
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• 52:55
  Just go to indeed.com-slash-clary right now and support our show by saying you heard about indeed
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  on this podcast. Indeed.com-slash-clary terms and conditions apply, hiring, do it the right way
• 53:05
  with indeed. HubSpot is a success story partner. If you're into this show, you're probably someone
• 53:09
  who likes learning from people who've actually done the thing. That's why I want to put create
• 53:13
  like the greats on your radar. It's a great show. It's hosted by Ross Simmons, part of the HubSpot
• 53:16
  podcast network. Ross breaks down some of the greatest creations and creators of all time.
• 53:22
  What they built, how they thought, the actual process behind it, and he's not just talking theory.
• 53:26
  He's been doing this stuff for over a decade. What I appreciate is that he makes it practical.
• 53:30
  Like how do you actually systematize creativity? So you're productive, but you're not burning out.
• 53:35
  So if you like learning from history, understanding how great work gets made, and you want something
• 53:39
  that's easy to listen to, check it out. Listen to create like the greats wherever you get your podcasts.
• 53:44
  I want to talk about the founders you work with and betting on people. And just for context,
• 53:49
  like I know that if people sort of research you and listen to other podcasts,
• 53:53
  they've probably heard this story, but like one of the most famous people that you've
• 53:56
  bet on is Gary Vee, but obviously you can tell that story. It's fun, but then also let's talk
• 54:01
  about what you look for when you bet on people as business partners as now investments.
• 54:06
  I know you've done over 100 investments. You've probably had thousands and thousands of pitches.
• 54:11
  So there's a select few that you've actually decided to work with. So what's the personality
• 54:17
  of somebody you choose to bet on? I think it comes down to first, like do I like this person?
• 54:21
  Like is this someone because businesses take a long time? And in 10 years when things aren't going
• 54:30
  as well as maybe they hope, like will I still want to be in the trenches with them? That comes down
• 54:35
  to like, but I like having lunch with them, but I like having dinner, what I invite them over
• 54:39
  to Thanksgiving dinner if they don't have family in New York City. Which we did often.
• 54:43
  Which we did all the time. I mean, I remember one thing. I don't even know if you remember this
• 54:46
  Walter driver who started coming to called scoply. He was in town. I'm like, yes, come over like
• 54:54
  you know, to our townhouse, you know, in the city and we, you know, he was stressed out. He's
• 54:59
  thinking about around. He went on to and very humble. Nobody didn't know. You know, we provided
• 55:05
  some of the seed capital to that. They sell for $5 billion to another game company. And like
• 55:11
  that's someone who I miss working with. I mean, he's the best, right? So people were always like,
• 55:18
  you know, I remember early on, it's like that they deliver bad news or any news, but don't take
• 55:23
  it personally. And for us, it's like, oh, this is all personal. Like there's nothing that we're
• 55:28
  doing that's not personal. Like I don't know if you've noticed, I'm married to my co-founder
• 55:32
  and my co-investor. And so there's nothing that you can say that is going to stop me from taking
• 55:38
  everything personally. And so it starts with that. And then it's basically like, is it the
• 55:44
  right founder for this like opportunity? And that's where I come in and really dig deep and
• 55:50
  trying to understand who this founder is or the co-founders. And then really separate the co-founders
• 55:55
  in a call to try to see if they know each other well enough. And it's getting harder because
• 56:02
  as investors, we're now the old people and ventures like a young person's game. Yeah.
• 56:07
  And so why do you mean by that? Meaning like reinventing new stuff and a lot of the new stuff
• 56:14
  that's created is created by young people who don't know any differently. And also don't need as much
• 56:19
  as we did. Like we didn't, I mean. And they're just smarter because they've access to the internet
• 56:24
  and stuff content like yours. We didn't, right? And so I look at like, you know, Robert and Gavin
• 56:30
  two Harvard dropouts. They come for the crazy idea, which is we are going to beat Nvidia literally
• 56:40
  a few years ago. Now they invented a chip that's 10 times faster than Nvidia's fastest chip.
• 56:46
  It costs half as much and it saves 75% of the energy. And we're like, this is crazy, but
• 56:54
  I like them. Maybe we do it, right? Fast forward and like etched the company etched.ai is transforming
• 57:04
  the design of like chips, right? And it's now a thing. But when we met them and we, you know,
• 57:12
  like dug deep on them, they had even the, you know, like, okay, they dropped out of Harvard who cares.
• 57:18
  But they had the same, we like that. But like morals, morals and values, right? And they had
• 57:24
  the right foundation and they knew how to work together. Things like that are very. I'm like, I'm
• 57:28
  wondering how these guys like, they're smarter than that. That's where you start. It's like, is there
• 57:32
  like a, can you just enjoy like a coffee or a drink? Do you want to break bread with them?
• 57:37
  Yeah. And are they ballers and they're like, they're as good in like the math world. That's what
• 57:43
  it is. And chip design as Mike is in the creative world or Walter was an entertainment and games.
• 57:49
  And all of these like founders find the synchronicity, right? Which is this intersection of like
• 57:56
  passion, purpose, skill set, which is just great fuel to become really rich. I mean, at the end
• 58:05
  of the day, these are very, now very rich people because they found that synchronicity.
• 58:11
  What makes you, and you didn't tell the, the Gary V story about your, your, your boardroom.
• 58:17
  So I just find that to be funny because he always talks about that story, but I didn't know that
• 58:21
  you were the. Yeah. So Gary came to Mike. What year was this 2008? I think we just started.
• 58:29
  Yeah. We started the company in 2007. We had moved into kind of like a different office,
• 58:35
  which was kind of a big deal, right? Because we were still trying to get our footing. And we just
• 58:40
  had one floor of this kind of brownstone on 60th and Broadway. And somehow Mike and Gary come
• 58:49
  into my office. And Mike says, Hey, like no preface. And I obviously knew who Gary was because Mike
• 58:59
  had been following him on wine TV, wine library. And I was like, God, this guy's outrageous. And
• 59:05
  he's like, it doesn't tell me beforehand, which was a big no no, because I think he knew what
• 59:10
  my answer was going to be that I have, I'm going to allow Gary and his brother and friends to
• 59:17
  work out of the conference room. And I thought he meant just that day. And I was like, okay, okay,
• 59:22
  that's cool. Like I'll rearrange some things. I think I can borrow conference room from Yaxx was
• 59:27
  down, you know, downstairs. And, and then Mike pulls me inside and says, no, they're moving in.
• 59:32
  And I'm like, what? And he's like, yeah, he is incredible. Like trust me.
• 59:39
  Well, no one really knew Gary as a business person. He was like early YouTube. And he basically
• 59:46
  came very vulnerable and said, you know, I'm 34. I have never made more than 100, you know,
• 59:53
  thousand a year working for my dad. He won't give me equity. And we know his dad would love him.
• 59:58
  You know, Sasha, I love you. And I don't have money for an office. But in my mind, I'm like,
• 1:00:05
  this kid has it, whatever it is. And I say kid, he's only like two or three years younger than me.
• 1:00:10
  But whatever it is, he had it. And he also, his pitch was I'm creating an agency to do for brands,
• 1:00:19
  what I did for my dad's store at Wine Library, using social content to grow business. And I'm like,
• 1:00:24
  well, we have social software. But this wasn't really transactional. I just liked him and fast
• 1:00:30
  forward, like just that act of giving. We've gotten so much in return. We did a three-hour live
• 1:00:37
  stream. We created a holiday for the book called, you know, National Shovel Day on National
• 1:00:42
  Garden Day and, you know, the three of us live stream selling the book. But also we get to see,
• 1:00:47
  like the really cool part was to watch a close and personal, like the story of Gary and his
• 1:00:56
  brother, AJ betting on themselves and realizing they weren't going to raise one dollar. They were
• 1:01:02
  going to bring in clients. That's what they were going to do. And they did that. And Gary literally
• 1:01:08
  annoyed me five times a day, running into my office, trying to talk to me about deals, how excited
• 1:01:14
  he was and to play ping pong. That level of like passion and obsession. Do you see that with all
• 1:01:20
  the most successful founders? We see that like Gary, not like Gary, like there's a different level.
• 1:01:25
  Like 70%. You definitely see it in the industry that they're in. So Gary has this love of life and
• 1:01:33
  that energy that's just surpasses anybody. But yes, we see the passion and everything. But his
• 1:01:40
  enthusiasm, like he would drive, I'd be on like with like Amax, like talking about client,
• 1:01:46
  like issues they were having. He'd be like, gas, gas, you got to come in. We're going to play ping pong
• 1:01:51
  right now. I have this idea. And I'm like, oh my god, there's two of you because I would say the
• 1:01:55
  same thing about him. And we also like, what was great is we were young entrepreneurs in the same
• 1:02:02
  space. And I remember going with him, I'm like, hey, the NHL is interested in our software. Come
• 1:02:07
  with me. Let's sell them some shit, right? And that's fun. And I'd go on and he's supposed to be
• 1:02:12
  joining me in this meeting. And he takes it over. Of course he stands up. So he's acting as your best
• 1:02:17
  sales guy. Yeah. And he's like, listen, this is what this is where the world's going. And you guys
• 1:02:22
  you get set up with all the teams on buddy media. And then I'm going to work with everyone to get
• 1:02:27
  the best content. And it was just fun. We come out of the media. I'm like, I don't know what just
• 1:02:32
  happened, but I think we're going to get some money. And then he'd come back and he's like, I think
• 1:02:37
  Gary and I close it a deal. I think we did. Like, he definitely did. We get anything we'll see.
• 1:02:44
  You know, that's something though, there's something to be said for that, like just like the energy
• 1:02:47
  of a founder is so contagious. And if you're like starting out now, like, treat everyone as if
• 1:02:55
  they're the future Gary Vee. Like, ask how could you help? Because the relationship like
• 1:03:02
  the network eventually becomes your network. Like what we've realized is that our network built
• 1:03:07
  over the last 30 years. These are our friends. These are people we would do anything with. And you
• 1:03:13
  know, it's not a surprise. We own a pickleball team with Gary. We did empathy wines. You know,
• 1:03:18
  V friends, which is as latest, he's been supportive of every one of our projects. And there's probably
• 1:03:24
  like maybe 20 others that we kind of continue to just do stuff with. And a lot of the, you know,
• 1:03:32
  we find a lot of younger entrepreneurs are more transactional. Like, why should I spend time
• 1:03:37
  with this person? Like, what are they doing for me? And I would just shy away from that outlook.
• 1:03:44
  I like that. I feel that too. I feel a lot of that. Like everybody's like, what can I get out of
• 1:03:48
  this person? Right. How am I spending my time? It's a gross attitude. It is a gross. It's like,
• 1:03:54
  it's a very short term thinking. But I don't know where that came from. I just feel it. I feel
• 1:03:58
  it a lot. Well, it came from the immediacy that they feel. They want things when they want it.
• 1:04:06
  They don't want to earn anything. And it's just this transactional way of thinking. There's also
• 1:04:13
  when we started out, it was never about money. It was about freedom. You know, you wouldn't have
• 1:04:18
  started an internet company in 1994, which is the first one I started. If you liked money,
• 1:04:24
  you look good for your age, man. That's going back. 51. Yeah. 51 wasn't college. And like,
• 1:04:30
  there were 13 million people on the internet. So like people are like, oh, you got on the internet
• 1:04:35
  because it was like about the money. I'm like, oh, no, this is like pre Amazon. Like, there was
• 1:04:40
  even the Netscape browser forget, you know, like Mark and Jason's working on mosaic at University
• 1:04:45
  of Illinois. And everything we've done that was just for money has pretty much turned out awful
• 1:04:52
  other than just like passive investments, like real estate and stuff. Because like, when you
• 1:04:57
  optimize for money and the money doesn't happen, you just, it's a miserable. You give up.
• 1:05:02
  And you make bad decisions. So like, a lot of the transactional stuff,
• 1:05:07
  I think comes from this kind of keep up with the Joneses that you see on Instagram that like,
• 1:05:12
  you know, if I don't do this, I'm not going to have the Lambo. I'm not going to have. And I'll tell
• 1:05:18
  you that there is no kind of pot of gold at the end that makes you happy. Like you will get,
• 1:05:25
  if you do the right thing every day, week, month, quarter year, you'll be successful in some way.
• 1:05:32
  Money does not come with that. Your happiness will not be found in your pot of gold.
• 1:05:38
  Yeah. I was going to say, do you think that social media is ruining entrepreneurship?
• 1:05:42
  I've, we've talked about this. Mike and I've talked to us because like, we feel like, you know,
• 1:05:47
  we kind of helped like the evil part of social media, right? With our
• 1:05:52
  management system back in the day. I think that social media for entrepreneurs
• 1:05:58
  can help them get their story out and build their own brand. And I think that's a really positive
• 1:06:05
  thing because I think the amount of money you have to spend is less at the end of the day.
• 1:06:11
  In terms of how these young entrepreneurs see themselves compared to others, the FOMO that they
• 1:06:19
  have and the comparison, you know, which is the thief of joy, I think it, it does ruin their
• 1:06:25
  mindset so that they get to a transactional stage, right? Which in turn lost you ruined the
• 1:06:32
  business. The chance of them being successful. Social media has fundamentally destroyed mental
• 1:06:37
  health in this country. And that's proven. You, then it's not going to get any better with chat
• 1:06:44
  GPT and like AI, you know, therapists and agents and friends. And so entrepreneurs are not immune
• 1:06:53
  to that. And all I would say is the good news about entrepreneurs is you're really internally
• 1:07:00
  motivated. Like great entrepreneurs kind of are driven by this fire inside them that could come
• 1:07:09
  from like proving someone wrong or wanting to get somewhere, whatever you have not wanted to
• 1:07:14
  have a job. Yeah. And these social media, you know, sites which, you know, we're guilty as
• 1:07:20
  charged, help popularize. They're all about external validation. And so I would just make sure
• 1:07:26
  that you're optimizing for the right things like you want your employees to like you. You don't care
• 1:07:31
  about getting 100 likes on every post, right? So tune into what, you know, what really matters,
• 1:07:40
  which is personal relationships, what your clients think, what your, you know, is your, are you
• 1:07:45
  good son? Have you called your mom this week, right? Yeah. But also you have you with what you're
• 1:07:49
  doing too. I think that some people just like, they don't even pay attention. Like this is all
• 1:07:53
  the self-awareness thing. For sure, they're not even happy with what like their own life and their
• 1:07:58
  own business. And when they wake up, they're depressed and they have anxiety and they're stressed out.
• 1:08:03
  And which a little bit of that is normal, but you still have to figure out like, okay,
• 1:08:08
  if I'm waking up and I hate the work that I'm doing, why? Well, as an entrepreneur, you, I mean,
• 1:08:14
  that, then you shouldn't be doing it. Period. You've already lost. You've already lost. But you
• 1:08:18
  could be doing it because this is what Instagram says you should be doing. I know. And then that's,
• 1:08:22
  that's just the wrong equation. Things change over time. I mean, there's diversity when you start
• 1:08:28
  out. Like your job as a startup is to become a company. Start up losing money, trying to like
• 1:08:35
  figure something out, company, profitable employees, resources. That's great. Once you get like,
• 1:08:43
  once you're a company and you have like cash flow and you can like get yourself in the right
• 1:08:49
  position, you should be able to have a more, I would say an easier to live in balance life. It'll
• 1:08:56
  still be imbalanced, but you will learn to live with that because it's not, every day's not
• 1:09:01
  existential. And so your job is to go from like where you are today, start up to a company. And if
• 1:09:09
  you're still miserable as a company, figure out how to replace yourself. Like a company should outlast
• 1:09:16
  any one person. If it doesn't, it's just like it's your service provider. What would be the one thing
• 1:09:22
  that is an immediate red flag or a no about working with somebody or an investing in a founder?
• 1:09:28
  I'm turned off by like gross arrogance that every question there's an answer for there's no
• 1:09:35
  vulnerability. There's, you know, we have no competition, right? We hear that again and again. It's
• 1:09:42
  like, oh, you have competition. Like whether you admitted or not. And I love when entrepreneurs
• 1:09:49
  say, I don't know. We don't know what's going to happen. But here is how we know it's going to be
• 1:09:56
  working. Here's what we're optimizing for. The second thing is I ask a very simple question.
• 1:10:02
  It seems simple, but it's hard. Sometimes what are you focused on? And if they're not like
• 1:10:12
  product one sales to like, you know, customer churn third, whatever their version is,
• 1:10:18
  it's like, well, we got to do this. We got to do that. We're thinking about this. It's like,
• 1:10:21
  now they're lost. Yeah, they're totally lost. Yeah. So it's distraction and arrogance.
• 1:10:26
  We're not knowing. They even like a lot of founders are doing work, but they don't know what they're
• 1:10:30
  working on. Like, okay, great. Like, what are you trying to become? Like, even if you do this,
• 1:10:37
  like, where does that get you? So the last thing I want to speak about is something you talk about
• 1:10:43
  called the go gauge. So explain to me what this idea is and why it's important for an entrepreneur
• 1:10:50
  to understand this idea. Yeah. So starting out, we made a lot of mistakes in terms of like how we
• 1:10:56
  spend our time. And we really want to think about like, how do we green light ideas? And this
• 1:11:03
  is for investors also like, how do you green light an investment? And it came down to five or six
• 1:11:09
  things, which are really important, which, you know, I'm not talking about like you want to hang
• 1:11:14
  out the founder like a lot of that stuff is just like you have to figure out, but in terms of
• 1:11:19
  a business. And we write on one piece of paper, like, what's the product? Why is it different?
• 1:11:25
  So if it's not different like, you know, how big is the market, but we define the market by
• 1:11:32
  like how many real buyers are there and how much they're going to spend first like the golf
• 1:11:37
  industry is $80 billion. Great. But you don't own a golf course. So you don't own like,
• 1:11:42
  travel. The most important thing I think we've realized is the fourth question, which is sales
• 1:11:49
  marketing. Like, how are people going to find out about this? Right? Because there's so many good
• 1:11:54
  businesses that are just sitting on a shelf that people don't know about. So many great products,
• 1:11:58
  so many great services. And we're in a world of like information overload and filter failure.
• 1:12:04
  And you're not going to break through unless you have a really targeted way to get to your
• 1:12:09
  customers. How do they find out about it? And how do you sell to them? Is it product-led growth?
• 1:12:14
  Is it enterprise sales? Is it? So we spend I think more than a lot of entrepreneurs like
• 1:12:20
  focus on that. We feel like in a big market, we can kind of figure anything out. But it's all about
• 1:12:26
  like the business. Now we add number we added number five after liquid death, which is all about
• 1:12:34
  distribution, not marketing, but okay, like the whole supply chain and how do you distribute the
• 1:12:40
  product? If we knew what we know about the CPG world, we may not have invested in liquid death.
• 1:12:47
  It was really hard to like take Austrian mountain water, put it into cans, get it into trucks,
• 1:12:53
  to then get it to trains, to get it to boats, to get it to like more trains in the US,
• 1:12:59
  to get it to customers. We're losing money on every can at the beginning. And so we added that
• 1:13:04
  of like, oh, we should probably figure out like the whole distribution supply chain stuff.
• 1:13:08
  And number six is just like on the back of an envelope, do the financials make sense.
• 1:13:13
  We're very big unit economics investors and entrepreneurs, you know, was it take to create
• 1:13:20
  the product? What do you sell it for? Is there enough money left over for just general expenses?
• 1:13:25
  And it's why we've gravitated toward like virtual currencies, software, like stuff that's like
• 1:13:32
  very high margin, you know, telehealth and telemedicine. And those six things like for us have really helped
• 1:13:40
  because businesses usually crater around one of them or two of them. Like one of them you can kind
• 1:13:49
  of talk yourself into a deal. But if you're like, man, it's a tiny market. And even with that,
• 1:13:55
  like there's no way to get to those customers. It's kind of like our weeding, you know, like mechanism.
• 1:14:01
  And it's a filter through which we can really help a lot of entrepreneurs think, not just about
• 1:14:07
  whether they start their company, but any kind of product change or service change. It helps
• 1:14:13
  them to think through that framework. Well, it's interesting because there's like,
• 1:14:16
  there are five million businesses created this year. We think, you know, there's a little more
• 1:14:21
  last year. There are 50 million businesses that are in people's heads, right? So you're sitting at
• 1:14:28
  your desk and you're like, oh, fuck, I'm miserable. I wish I just had the freedom to do my own thing.
• 1:14:33
  You're most valuable asset as an entrepreneur starting out as your time, right? You may not have
• 1:14:38
  money. You may not have a network, but like your time is very limited. And so use the go gauge to
• 1:14:46
  figure out, is this worth my time? And a lot of entrepreneurs, I give that when I see it, I'm like,
• 1:14:53
  I don't think this is worth your time. And I had one entrepreneur recently, you know, came back and
• 1:14:58
  said, I caused her to start drinking again because like, I was really harsh to her. I'm like, no,
• 1:15:03
  like I just told you stuff that other investors would like bullshit you about. Like,
• 1:15:08
  I told you what I thought, if you didn't want to meet, then you shouldn't have met. But like,
• 1:15:12
  you're in a very small market. It's not going to be a big market because your market's been around
• 1:15:17
  forever. And so I was just saying that you're really talented. Is this where you should apply your
• 1:15:23
  talents? And I see so many entrepreneurs, they start a business, they get all excited. And then
• 1:15:28
  they're like, Oh, what did I do? Like, this is not going to end well. Like I, and they don't
• 1:15:33
  have to get out of it. Yeah. So like put the time in, sleep on it, talk to people. Yeah, a lot
• 1:15:41
  of entrepreneurs, I don't want to talk to anyone such as, you know, secret idea, like such a good idea.
• 1:15:45
  It's like, Oh, no, like that's going to be like, it's not about the idea. It's about the execution,
• 1:15:49
  right? It's going to say that's why it's so important to have this like personal board of
• 1:15:53
  advisors around you that that are not sick of us. Yes. Yes. Yes. What's the most common
• 1:16:00
  delusion that a founder has about their ideas? I think, I mean, we see it over and over that there's
• 1:16:05
  no competition. Like Mike said that that like their or their products better, they're going to be
• 1:16:10
  able to do something faster. Any kind of adjective or adverb that they put on things, we just kind of
• 1:16:15
  like, okay. Or it's so good, you know, it's so good that, you know, they'll just find me, like
• 1:16:21
  customers will find me. If like, if I build it, they'll come. I don't know why we love
• 1:16:26
  like creator businesses. Like we love businesses that have built in distribution, right? So
• 1:16:32
  is that a surprise that like V friends one or that prime one or that any of these businesses
• 1:16:40
  with like passionate, and I'm not talking about just like, I don't love businesses where some
• 1:16:44
  of them don't attach as their name. But like, when someone who has distribution really goes after
• 1:16:49
  something that they're passionate about, like, there's a lot of magic that's happening. It's easier
• 1:16:54
  than ever to market because of social media and all these tools. If people want to connect with you,
• 1:17:02
  if they want to, I'm assuming, so your book, shoveling shit, a love story, that's available anywhere
• 1:17:09
  you can get books. Yes. But where should they go? Where do you want to send them? You know, always
• 1:17:13
  DM us like, because we're actually on it. If you can imagine that, but you can go to info at
• 1:17:18
  Casamike.com. Or just Casamike on any social Instagram, Casamike.com. What do you admire most about
• 1:17:26
  each other that you've never set out loud? I think his ability to consume information and know what's
• 1:17:34
  going on. It's just remarkable because he reads, he listens, he networks, and he's able to synthesize
• 1:17:45
  all of that at such a rapid pace. I think it's just very unusual. It was very nice of you.
• 1:17:55
  I would say her smile, love her smile. I love her pace of aging. She's still super hot.
• 1:18:05
  At our advanced age, no one cares more. Like if you are in her world, you feel the love.
• 1:18:14
  And if you're not, you don't because she doesn't spread it far and wide. I think that that's,
• 1:18:21
  you know, it's pretty special. If you could, after all the things you've learned over your
• 1:18:26
  lives and careers, you can only pass on one lesson to your kid. It's the most important lesson. So
• 1:18:31
  what would that lesson be in a way? And both of you can take it too. Mine would be to focus,
• 1:18:36
  find something that you really are passionate about and put all of your energy behind that.
• 1:18:41
  Mine would be to always help those whom you love, to always be there, to lend a hand.