How Shoveling $h!t Built a $745 Million Startup (And What It Really Cost)

Hey, I want you to listen to me very carefully for a second because what I'm about to say can change the way you look at success. The difference between staying stuck and finally breaking through isn't just talent. It's learning how to fall in love with the hard parts of the journey. And that's exactly what we're getting into. Today I'm chatting with Cas and Mike Lazaro, the powerhouse couple who built and sold their company Golf.com to Time Warner for $745 million. They're sharing the real secrets to success in their new book and prepare for some profanity. Their new book, which is titled Shoveling the Messy Truth of Entrepreneurship. Today they're going to talk about how to have the tough conversations that actually build trust, the mental cheat codes that keep you locked in, and the mindset shift that separates the people who burn out from the ones who rise. And if you've been grinding, pushing, and wondering why it still feels so hard, this conversation is the reset that you didn't know that you needed. I know you're going to get a lot out of this one. So without further ado, let's jump into the interview. Mike, you said something really interesting just now because you said we can talk about difficult conversations and you said Cas is really good at that. And I found that fascinating. So why didn't you say we are good at that? Let's start there.

Well, the key to being a great entrepreneur, which I don't know if I am, but we've had some success, is to be self aware and it's very difficult for me to have those tough conversations. I've gotten better over the years and Cass has really been my rabbi and Sherpa there. The first time I went to lay someone off way back when@golf.com let's just say he made some great arguments and he came away with a higher salary and a bigger title. And so, you know, and I was in, I go back to that meeting and I just listened to what he said. I wasn't present with what I was trying to deliver and I basically got railroaded by a salesperson who was good at negotiation. As you know, I don't know if he was a student of yours. He's 20 some years ago. I don't think so. And what Cass has done is she's given me inspiration and more importantly, scripts and a way to practice. And what I've realized is that you get the elephant in the room, have be very direct and a lot of the conversations start like this. If I was to lay you off, I'd be like, nice to see you. Today is your last day. This is a very difficult conversation, but I want to give you some feedback on why. And you don't bury the lead. You get the news up front and then use empathy and what you've practiced, hopefully, to deliver it in a way that makes the person who's being laid off feel human, at least.

That's great. That is great. And Cass, I see you nodding approvingly as if your student has now become the master.

That's exactly it. I mean, it's taken some time and I think he's much better at it now and has a lot more empathy and compassion. When you go to lay someone off, it's not eas. And I always say that if you are a founder or a business leader or a manager, and you've spent so much time and put so much care into hiring someone so really working on that relationship to bring them on board, and you have that first lunch and that whole week is planned out for them, it's really your obligation to make sure that at the end of the relationship you have as much care. And so my thoughts on this whole subject are we need to help people when they leave because the fault is squarely on the shoulders of the person who hired them. Right. No matter what, the buck stops there. So it's your job to try to help them in their future employment. Because nine times out of 10, if not 10 out of 10, you know, that person went on to do something that was a better fit somewhere else. Yeah, but you know, that's why I talked about skill sets that we needed and you know, tried to give them as much information as possible.

I love it. No, this, this is great. And I, I love the approach. It's a heart centered approach throughout because you're recognizing, all right, it's not so much of a negotiation as much as, as it is delivering bad news as empathetically as possible and helping them with the transition.

Yes, yes, definitely.

That's great. And Cas, one of the things that you talked about was the, the relationship that you have with the team member or former team member in this situation. But I think for me, I. My, my wedding in three days or so. So I am fascinated to see from a relationship perspective, how in the world do you all pull this off when it comes to the, the relationship aspect behind the business?

Well, first of all, happy, congrats. How many years will you be married?

15 years.

Nicely done. Nicely Done that. That is an incredible accomplishment. So congrats there in terms of us working together. We look at, you know, our partnership and business no different than our marriage. And when you look at other great partnerships, co founder relationships, leadership teams, it is like a marriage. These are the people that you text the first thing in the morning, you text when you go to bed and there's no difference. The, the thing that we always say though, and we really, really encourage all people to do this before they get into a serious partnership is to same conversations you would if you were going into a marriage. Right? Except this time it's not about religion, finances necessarily. It's, you know, what's your work ethic, you know, how, how much do you plan to give, what intensity level can I rely on? Right. And then you go to things like, okay, so we do this 14 hours a day. What do you do outside of this that makes you happy and helps you reset?

Right.

And if it's fly fishing, then you know that so you don't get resentful that your partner's going to do that. Same thing happens with us with Mike. You know, we haven't, we don't really work in the same lanes, right. So that's like a big cheat code for us is that we can, we can be married and work together because we're not overlapping in skills. The book was a little harder, I'm not going to kid you. It was a little harder because we were in the same lane. But like everything, we trust each other on our expertise, so that's how we make it work.

Yeah, that was really well said and proud of you, Cas. Way to go. You know what's interesting is both marriages and co founder relationships start with this honeymoon phase, right? There's like this passion, excitement and you're so psyched to do a big dreams. And at the end of the day it's really building the foundation of trust over time that the relationships prosper. And these are very important relationships, marriages and co founders. You're sharing finances, oftentimes you're sharing reputations, mental health. If I'm not feeling great, my co founder hears it. Or in this case Cass, my co founder and wife. A lot of co founder relationships fall apart because of misaligned values conflict that comes up in relationships. How you argue is important. Are you productive, empathetic or does resentment and blow ups lead to kind of passive aggression? Right. And so just like any relationship, we encourage you not only to have the tough conversations but, but be true to yourself and communicate what's important in a way that your partner knows. Don't assume that they can read your mind. If anything, they're reading the wrong part of your mind. So they're reading your fears and not necessarily, you know, your dreams and the exciting stuff.

Cas. I saw, I saw a thought. I saw it.

Yeah, well, I mean, he's dead on. Like fears get. Gets in the way of anybody. I don't. If you're working or you're doing the hardest job in the world, which is caring for children right at home or teachers, I will say that as well. And fear, doubts, insecurities, they all get in the way. That is the baggage that we carry into the world and your job. Mike did this post, I think it came out today where it was about power, that people should pursue power. And he wasn't talking about over people. It was over your mind. Right? It's power over your mind. And so that was a good post, hun.

I don't think it's out yet. So don't like, don't whatever.

But it's, it's like the power over your thoughts, right? And it's the discipline of your mind, you know, that's.

Well, it hit me with. I was talking to a founder who was very focused on money, as founders should be. You don't want to run out of money. But this was basically, I just felt there was. She was too focused on personal money. And the money is how you keep score. And it's the result of doing the right thing. It's not the thing itself. Right. And so I encourage him to really work on how he shows up. And what hit me is that like he was chasing money, but he was ignoring like, you know, taking control of his own brain. Right. And it's that like taking power of your own mental health, your outlook, your habits, that produces results. But you can't just focus on the results. And you know, I'd encourage all entrepreneurs to really drill into like, what do they need to like, succeed at the highest level. And what I would argue is that you're not without ego. A lot of entrepreneurs like, oh, I don't have any ego. When you start a company, you're inviting people to watch you fail in public. No one does that if they don't have some sort of ego. But you have to lead with the heart, right? You have to lead in a different way. If the ego gets in the way and that's how you're leading, it's just not going to turn out well as we're seeing with the country and a lot of our leaders who have lost the point of the story. And so that's where that came from.

Well, first and most importantly, Simone, our producer, I want you to send a message to our copywriter and write a post on power immediately. Power over the mind. It's my idea.

You can taste it. Listen, my ideas are your ideas. He knew isis.

We still have a few minutes, but I love this, because what's really cool about this is we're focusing on the inner game. And of course, from the people looking from the outside in, they're going to see the success, they're going to see the venture fund, they're going to see the acquisitions, everything. But they can't see inside your own mind. And when we think about all of the things that are required to be a good leader and a good partner and a good spouse, we always focus on that external behavior, but we don't talk about the fact that what we're seeing on the outside is simply a manifestation of what happens on the inside. And when you're thinking about this, I want to. I want to think about the process of how you got to this elite level mindset, because I know at this point it's. It's habitual. I don't think it's. It's probably still not easy, but it's habitual. What was it that made you realize, all right, I need to do something about my inner game so I can have that power over my mind so then I could have the results that I want out of life.

For me, it was. It was definitely all of my athletic training, so I always trained as a tennis player. I played in college and some pro after. And it was all about the mind. Because if you think about when you're competing, how you differentiate the top is not by, oh, they have a great serve, they have great forehand, whatever that is. It's the mental game, right? And so I think from early on, you know, my dad, who was mostly my coach and big encourager, was the person who was talking to me about mental habits, visualization, and really showing me things. You know, he's almost 89. So back then they didn't have words like meditation, right, and things like that, but really talking toward the mental side because the tracks that you have in your head, whatever that record is, and you say it over and over and over to yourself, that is manifestation, right? So it's either going to come out as I'm going to be able to take action, or I'm going to be paralyzed with fear.

Yes. Oh, this is great. So I. I have to jump in on that one, Cass, because I didn't realize your. Your tennis pedigree. I didn't know I was in the. In the room with royalty here. So my. I. I love tennis. I was president of the club team at. At Ohio State.

That's amazing.

Thank you. Well, it's not as amazing as pro, but we try in here, you know.

Yeah, different. Different levels, though. I mean, like, you. You're Ohio State. And then I, you know, I played at a smaller D1 school, so.

Yeah.

Oh, that's the. This is great. Because now I'm seeing a lot of this elite mindset here, too, because I had the opportunity one time to. To play at nationals in front of Billie Jean King. And I read her book, the. The Dollar Rebellion, and she revealed the statistics. She said that I believe it's something like 90% of women who are in the C suite are former collegiate athletes. And there is a mentality that can come from sports. That is when you're younger, you just focus on applying it to sports, but we don't recognize just how attributable it is to everything. So let's go deeper into that. What are some of those key lessons that you pulled?

I think it's. I think it's applicable to suffering. Like one of the things that athletes can do, and we call this a massive cheat code that for, you know, startups, when you're trying to hire those first five to 10 people, right, which are very, very important. Pick an athlete, pick someone who was trained in the military, right? Because they also will be okay with lots of messes, lots of punches in the face when things don't go well, and they will know how to get back up in the face of their failures. Right? And entrepreneurs, the ones who succeed. And I think it's the same thing with athletes. The ones who succeed look at their failures as getting one step closer to their victories. Right? And so it's that discipline. And when you're trained, and you know this very well, there is no other option. You're on to the next match, you're on to the next point. So it's that kind of resilience and also not allowing the doubts to creep in as much. Right. I think we. I think Mike and I, for very different reasons, have a. Endure an endurance of doubts. Like, we can say, like, wow, a lot of stuff's happening in us at once and we're not going to let it bring us down. We know it's absolutely affecting Us, it is, and we know we can get through it and it will pass.

This is so powerful. And, Mike, I think this is a great time to shout out your hat. So folks who are on audio, Mike is wearing a hat that says Shoveler, of course. I'm sure it's an ode to the name of the book, Shoveling Shit, because I think this is a perfect transition to talk about that, because I think one of the things that people don't fully appreciate when they see elite entrepreneurs like yourselves is they look at what you have and they. They are jealous of the destination, but not the journey. And they don't recognize that the only way to get from where you started from to where you currently are is by just leaning into and embracing the inescapable pain of progress. And so when you're sitting here at the beginning of your journey, I want us to go all the way back. How did you deal with the pressure and the difficulty when it wasn't 100% clear that you were going to end up where you are today?

So, first of all, your use of language is incredible. I'm taking notes. The inescapable pain of progress is perhaps the favorite phrase I've heard in a long time. And so, you know, when we. It's funny you say about, like, elite entrepreneurs, because we feel like beginners, and there's something about the beginner mind that keeps entrepreneurs going. It's curiosity. It's. We don't know, have all the answers. It takes a team. This book is a great example. We'd never written a book, so we had to, like, reach out and ask for help, try to dissect the industry. What kind of book? Like, where does it fit? How are we going to market it? All that stuff. And I think there's this concept that we've tried to capture in the book, which is called Shoveling Blank A Love Story. I don't know how much profanity you like on. This is a show.

By the time this goes out, we'll be independent, man. We can say whatever we want.

Yeah. So shoveling Shit a love story is this concept that, on one hand, there's no worse way to spend your day. You get kicked in the face, people are saying no, Employees want to quit, customers want to leave. You're running out of money. Name it. And it's like hitting the fan, right? And if you ask any entrepreneur, would you rather do something else? They say, no, it's both miserable and awesome at the same time. Because within these companies is where we find our Purpose, our passion, our humility, our hard work, which is a virtue. And so all these great things that come, that come to entrepreneurs are only because of the misery. If you could start, if you could hamp a shingle, make a billion dollars in a week, it's like, okay, it's not rewarding, right? It's not about the money. It's about that journey. And so when you start out, we have nothing and you want something. When you're a company, you have revenues and profits. When you're a startup, you're just trying to figure it out. You're trying to become a company. And we started young and made a lot of mistakes. And what this book is, is the 50 cheat codes. 50 plus cheat codes we wish we knew early on. They're not shortcuts, so you can't just press a button, but they're learnings that we think will help you as an entrepreneur or a professional executive, whatever you're trying to accomplish, make fewer mistakes, both at the company and personally. Why does success mean anything and matter if you're miserable at life? And so a lot of the cheat codes are how we protected our relationship, protected, built relationships with friends, how we kind of got back to our health after making all the mistakes of no sleep, overeating, drinking, all that stuff. And so it's just as much about the cheat codes to live a life worth living than it is, you know, building a business worth building this.

It's essentially. It's almost like the. It sounds like it's the philosophy of entrepreneurship extrapolated to life to a certain extent.

Yeah, definitely.

It is life, right? All it is is life. Like, you spend more time working than you do at home as an entrepreneur. So if you don't look at your business as your life, you're going to have a life that you wake up and be like, I have no relationships. My health is out of hand. I have burned through everything good in my life, and it's just not going to be worth it. And I think there are a lot of people, at least from the tech industry who are asking them these questions, who have nine figures behind their bank account.

I think this is a great place for us to talk about Buddy Media as a bit of a case study, because you went from idea to $745 million exit. And when you think about the, the, the process of shoveling shit in that business, what are some of the stories that come to mind when it comes to what it took to get to that point?

I think right off the bat, it just Pivots and how important it is to take your ego out of the way as entrepreneurs and leaders, to take it out of the way and actually look to see if your, if your metrics are making sense. Are you actually getting customers? Do customers want what you have? Right. Because as great entrepreneurs know, you have to have, you have to, you have to be able to tell stories. Right? That's the whole marketing side of what you're doing. You tell the story of where you're going with, with your company, but you also have to be careful that you're not telling yourself stories. Right. And you're actually looking at the data. And we did it really, really well. Mike is excellent at pivoting. He's excellent at saying, wait a second, this is not working and we have to move now and then behind him. There I am. And I'm just going to make sure that I execute on everything he says. So I would say like the enormous amount of crap that we've had to shovel is around pivoting.

And another thing, just pointing this out again, this shows self awareness and trusting your team member and partner too, because it sounds like you Cas. You handle the tough conversations really well. And then Mike, you are able to make these pivots strategically really well. I love the amount of trust that you have with each other in this process. And I'm sure vulnerability is a big part of that too. How do you balance trust and vulnerability while still staying focused on the task at hand?

Man, that's a loaded question. Yeah, I think we're, I think we're still working on it, to be honest. The. And a lot of this stuff comes easier to cast. I don't know if it's because, you know, she's cast or. You know, what I have noticed is, you know, all of our companies have been women led, not only cast, but great executives like Susan St. Leger, Dina Hberg. And it just. Self awareness comes easily, more easily, it seems. I learned the hard way in buddy media what not to do. And Cass brought in a coach, an executive coach, because I'd never run a company with 500 people with offices in Singapore and London and throughout the US And I wasn't performing the way I should have. Both personally. I was 40 pounds overweight. My mental health was all over the place because I was like traveling the world and at the same time being put on pedestals. Entrepreneur of the Year, Ernst and Young, all these awards that are kind of bs but it builds up your ego. And what this woman did, the first thing she did was a360review. Tammy Jersey was her name. And she asked all my direct reports and others, and what came back was not what you want. I was getting in the way. I was both distracted and distracting. I'd come into meetings just trying to get my way and not listening. I remember at every point. And she was 100% right. And it took me some time to digest, not be upset, because this was my team who I knew loved me, but telling me the truth. And that was even though Buddy Media was so important to us, our family, future generations, it's those learnings of, like, you know, how I was getting my own way in other people's way, which I would encourage all leaders to seek out that information. You could ignore it, you could bury it, but that's going to be the baggage that takes, that you take forward, not only with other businesses, but your relationships, your kid relationships. Right. We have three kids. I was doing the same thing with my kids. And I can't stress enough. When you become CEO, when you become somewhat successful, people don't really tell you the truth. Find your truth teller. Cass is a, let's just say, radical realist. She's not a pessimist. You can't be an entrepreneur and be a pessimist, but she tells things the way it is. I think there was so much going on with me at the time, it would have been hard for her to list it all out, which is why she made the brilliant move of gifting me this truth teller. But as we wrote the book, that was one of the parts of Buddy Media that really I've taken with me going forward.

See, this is powerful because I appreciate the vulnerability here in telling this story. And I also want to circle back to something we've talked about a number of times here, which is self awareness. And we also talked about ego, because I think ego is kind of like an ingredient in making cookies, for example. It's like salt. You need a little bit of salt to make it work. But if you have too much salt now, you have salty cookies. Nobody wants that. And a lot of times we have too much ego, and it messes up the entire dish. So. So let's. Let's try to get as real and tangible as possible when it comes to balancing the ego, because the ego sometimes, when dialed incorrectly, can be a bit of your edge. But of course, an ego out of control leads to bad decision making and destroys relationships. So how do we balance that?

Yeah, I mean, I think that's the. The tough part. I think in business, you Know, it might be a little bit easier than in. In personal relationships, because in business, if you've done your job correctly as a leader, as a manager, you have metrics that you've written down that are your goals, and hopefully you've also attached what success looks like for those goals so that you can have your ego be checked at the door when you're saying, wait, I think everything's going great, but let's go look at the data. The data says something differently in real life. With personal relationships, I think it's much harder to get your ego out of the way because what are the goals that you're setting for yourself in relationships? Right. I mean, obviously, you know, you could say, like, a supportive relationship. I'm not just talking about marriages, but friendships. Right. I want someone to root for me. Right. No matter what. I want someone who is not intimidated by my success, and I want someone who's, you know, shows up for me, whatever those are, then you've got to try to move that ego aside and really be as vulnerable as you can.

This is so good. This is so good. And what. What's funny again about this is that there's no way to make this easy or feel. Or feel good.

No. Because, you know, you said it. You said something in the beginning, like, there are no shortcuts in life. There are reps. You know, you just do them over and over and over again and practice. Right. I think that's one of the things probably you and I learned very early on as tennis players is you just don't hit the ball, like, you know, a couple days a week, and then just go. Try to see if you could, you know, play at your best. You've done hours and hours of preparation. So, you know, when people come up to us, especially some of the younger entrepreneurs, you know, they say, like, what should I do? How, you know, how long will this take? Like, how long will this take? Like, our Success happened over 30 years, right? 30 years and lots of failures.

Wow. And I remember one of the things my coach said, even when I was like, you miss a shot, and then it's like you take a shadow stroke. And I remember him jumping on me one time. He's like, that's not. That stroke was not good. Okay? So if you. There are no bad reps here. No bad reps here.

Intentional, Right? Be intentional.

Yeah. And what I found. And tell me if this is me just being a bit neurotic and extreme here, but I've tried to extrapolate that mentality to everything so even when it comes to, like, jokes that people would make about what it takes to be successful in business or in relationships, like the passing humor, it's like, I have to say, all right, cool. I'm not even going to engage with such thoughts because it's too familiar to the ways that I used to think in the past that were not leading to the results that I wanted to, like destructive thoughts about marriage and relationships, destructive thoughts about what is required to be a leader. And in order for me to maintain this high level of, like, this elite mentality that's operationalized for leadership in my company and then leadership at home, I had to really protect my mind. Because you recognize that if you're scrolling on social media, you're having idle conversations, a lot of times your mind is under assault by just a constant bevy of bad ideas.

Yeah, yeah, absolutely. 100% agreed.

That's part of getting, you know, taking power over your brain. And it's all, you know, it all comes down to a few simple emotions and ideas. One is fear. So fear fuels a lot of bad decisions. The other is ego that we talked about. And I think a lot of entrepreneurs that succeed, they let fear and ego be an engine for what they're doing. Like, I didn't want to fail. The fear of failure was a big motivator for me, much more than any money. Like the idea that, oh, we've raised 100 million, if we fail, we're the best, biggest flameouts in the history of New York City tech, right? Imagine that they had all this money, they had all this press, and then. And so let it be your engine, not your steering wheel. And what I tell entrepreneurs, we've invested in over a hundred, and leadership is something that we are always working on. You know, there are a few things that you can do to do it. One is just build systems that punch your ego in the face, which is what Tammy Jersey did. So when your ego is out front, make sure there's someone to punch it, because it's going to help you. Second is separate yourself from the company in the sense that you are not the company. You are just a part of this group that is running the company. And let people challenge your ideas without feeling that it's challenging you. And so people. I would share ideas, people would challenge the ideas. And I thought they were trying to battle me, but no, we were just having a healthy discussion of ideas. And then what happens? You start sharing credit. Right. And owning the blame. So praising others and taking responsibility for mistakes. And the problem with Ego and fear is you want to get rid of fear right away. Ego wants you to win. But this is a forever game. This is a much longer. Like if you're building anything that's worthwhile, you're going to be doing it for many, many years. Right. And ego and fear are short term things that get in the way.

This is feeling like a therapy session. I appreciate this. I think this is what so many people need to hear. And again, it's not just limited to entrepreneurs. This is life stuff.

Right.

This is life stuff.

Right.

And I, I really admire both of you for your vulnerability and, and how you're, you're articulating this so clearly because it gives people a bit of an idea of what it takes to be successful in this level. And I know a big part of what it is that you all do now is coaching founders and entrepreneurs and leaders as well. So I think this is a good opportunity for us to shift a little bit and get a little bit more tactical too, because for both of you, you've sat in just about every seat you could possibly sit in in the business context as founder, CEO, investor, advisor. And so you know what it takes to succeed and what often happens when people fail, what leads to that. So let's say hypothetically, if there is a founder who is just in the thick of it, cash flow is tight, team morale is shaky, what would you do to coach them to make decisions without being consumed by fear or ego?

Yeah, I mean, the number, and I did this earlier today and yesterday, and the number one is focus. Like you need to say no 10 times more than you say yes. And it isn't just kind of this idea, it's a discipline, it's a radical violence against distraction. So you're just clearing the way of anything. And the context was an entrepreneur said that they don't know what to do in the morning. So much going on, they've got so much coming their way. How do you prioritize? And I said, okay, what are you trying to do as a company? What's your vision? Silence. Okay, so that's a data point. You don't know where you are going. Right. So the response should have been, I want to be number one, blah, blah, blah in this market. Right. Or whatever their vision was. And then I said, well, what are the top three things that are most important for you to succeed? Whatever you think success is, which clearly you don't really know because you couldn't explain it to me. They're like, well, we got to build product. And then but we have some unhappy customers, and I don't have anyone doing this. And I'm like, okay, so that's why you don't know what to do. You need to have a vision for where you're going. And in order to get that vision, here are the three things you think you need to do. You wake up every morning and say, where am I on these three things? What do I need to push forward? And you tune out the bullshit. You tune out the rest. Right. Or you empower others to manage it. You say, listen, you're ahead of customer success. I trust you. It's why I hired you. You're my partner. Go run your business. I got my own initiatives that I'm focused on right now. If anything is above your. What you think is above your capabilities, please come to me. I'm here to help you. But I trust you. You're a great leader, right?

Yes.

And that focus thing, both personally, professionally and personal projects. Right. Stuff you want to accomplish just personally. Like, for us, it was the book. But everyone has their own projects that may not be just the company. Focus. Create a vision. Figure out what you need to do to close the gap between the vision and reality. And once you have it written down, the rest is easy. You just look at it in the morning and say, what do I got to do?

See, I love this because focus is a word that people say all the time, but so few people understand what it really means. Because we always say, all right, focus, focus. What does that mean? I'm going to pay attention to the right thing. But more of focus is about ignoring the wrong things, right?

Yes, that's it. And especially for creative minds. So for the visionaries out there like Mike, it's harder to ignore the shiny new objects. Right? It's harder to sit there and say, okay, wait, I know what I'm doing. I know what I'm doing. Go back, go back, go back. So again, it comes back to reps and discipline. Because you, you have to protect your time. That's the most valuable resource you have as a leader, a. A and an entrepreneur.

Yes. It's. This is great. I. I love this. And, and one of the things that I started to do is take the things that I've learned in just life and business and try to teach it to my kids as. As early as possible. So my, my son's fourth birthday was just yesterday, and I have another one who's nine. And one of the things that's going to lead to success just in life is discipline and focus. And the ability to pay attention to the right things and ignore the wrong things. And when I started to think about the tantrums or challenges that we've had, which have been minor, but I pay attention to those things, I realized that a lot of times it just comes down to a lack of focus and then an inability to ignore those distractions. And so I came up with this approach. I called it brain training. Kids hate it. They'll appreciate it, though. So whenever I see just like a lack of focus and it's like maybe, maybe once a day, I say, okay, it's time for some brain training. And so I take them up to a wall, and if you have kids, you, there will always be a spot somewhere on the wall. And I say, just look at, look at this spot. We're going to set the timer for one minute. And then once if you look away at all or if you ask a question, it starts over. It starts right over. Right? And when I started this with my 4 year old, I'm telling you, in 24 hours, the amount of tantrums that he's had just decreased significantly. It's incredible.

That's so amazing that you say that because Mike and I, well, first of all, as entrepreneurs, we gave up a lot of their younger childhood because we were working so much in hopes to get back to them when, you know, they were bigger kids with bigger problems. And one of the things that's interesting and I kind of kick myself about is, and I think this might be what people do is, you know, I had a very regimented childhood. I was a nationally ranked tennis player. I had curfews even up until 18, 20 years old. I was in the gym. You know, there was never a day that wasn't regimented around me. And what it did is it gave me massive discipline in my life post being a tennis player, that identity shift. What's interesting about our kids and many kids that I, that I know of, former athletes, is sometimes they don't push them toward that. Right. So I kind of was like, okay, that was a very intense intentional childhood, but let's just see what they want to do. Right? And I see our generation of kids struggling more with the idea of focus. And then they beat themselves up because they don't know what they're supposed to be doing. Right. And they don't allow themselves to work really hard and then pivot to a passion or a hobby. And so it is an interesting concept. I love that you're training on focus. That's so big.

Thank you I'm trying. I'm trying that. I think of it as an investment. I'm like, okay, I know it's. It's annoying for all of us. I don't want to sit here and look at my son look at a wall.

That's not.

I want to spend my time, but I'm like, it'll pay off at the end.

Well, but it's also going to come down to a coping mechanism. I think at the end of the day, it not only will be a skill that you have trained, but it's a coping mechanism. To micro focus on something allows you to not panic and have anxiety about everything.

Yes. I think that that's powerful and I. That's a great segue into the next concept, which is emotional stamina. And when it comes to self awareness, that's the root of emotional intelligence. But the concept of emotional stamina is so powerful and so I don't even want to say misunderstood because I don't think people have enough awareness of it to even misunderstand it. So we need to raise awareness. So when you think about emotional stamina, what is it and how does it apply to the business world?

I think of it as. And Mike, you can go too. Of course. I think of it as distress tolerance.

Right.

Both personally and professionally. How much distress uncomfortableness sitting in the shit can you withstand and still move forward, making the best decisions you can with the information you have at the time without getting paralyzed? That's how I look at it. That's what we need our kids to be. That's resilience, right?

Yeah. I mean, the stamina part is the interesting part, because anyone could get through a hard day. Few can get through a thousand straight hard days, which a lot of entrepreneurs go through. Right. It's not unusual to have three years of like very tough times of you're trying to raise money and you're trying to bridge, like hire someone, but you need bridge financing. You're trying to get product market fit. And success is earned by those who don't disappear at the end of the day. Right. Like, how many people have done 10 podcasts? A lot. How many have done a hundred? Very few. Right. And so it's that consistency over intensity. Right. Anyone can work hard for a day. Anyone can put up with like a hundred punches in the face, but can they do that for a thousand straight days? I've always been fascinated with these ultra marathoners. A lot of people can run the New York marathon, but there are very few people who could do the race where it's one marathon per continent in seven days. So you're running seven marathons, seven days on seven different continents. And that's a real thing. Right? And it's a next level thing that always reminded me of like entrepreneurs that I land from a 19 hour flight from Singapore. I'd have three hours to sleep, then I'd shower and I'd have to be pitching investors in the morning. There's no other option. You just have to keep going. And so it's not only the focus, we talked about it, but it's this delusional self belief. It's somewhat clear thinking. It's a high shit tolerance. And it's. What I love about entrepreneurship is it's a team sport. So you're miserable with people hopefully you like. And as I said earlier, there's no better way to spend your day. So it's like the book shoveling a love story because it's not a negative idea. It's not just shoveling shit. That's shoveling shit. The entrepreneurs who, who fall in love with it, they're the ones who break out and do great things. So it's our love story to each other. But to those entrepreneurs who end up developing a love relationship with hard work, hard work becomes their love language.

In many ways, that's powerful. And you're absolutely right. And when I think about it, the emotional stamina, pain tolerance, these are critical elements of what it's really required to be successful in any element of life. I think about with negotiation, tough conversations, one of the challenges people have is that anybody can ask a good question, anybody can listen effectively, anybody can manage their emotions for three minutes. But can you do that over the duration of a conversation? That's a completely different thing. And I think a lot of times people look at what entrepreneurs do and they look at some of these behaviors or these tools or tactics in isolation. So they say, yeah, I could make a cold call, yeah, I could have a give a speech to a team or whatever it happens to be. But can you do that every single day without knowing whether or not it's going to succeed while still demonstrating resilience and confidence to your team while you want to break down inside every single day? There are few people that have that type of toughness. And this is a question that I've heard a lot of times and I want to get your perspective on it.

It too.

When it comes to emotional stamina, how much of it is learned? How much of it is innate? What's nature, what's nurture? For both of you.

I, I mean, again, I, I think there's two types of people. This is clearly just my philosophy. I think there are people that are visionaries and I think they're operators, right? I think there's two very different types of people. And I think that, that that skill set, you know, whether it's nature and nurture, changes depending on who you are. So maybe all my reps, you know, from all my discipline and training of being an athlete definitely was the nurture part. But I think I was kind of born this way with high tolerance. And I don't know if it's the same for dreamers like Mike. Mike, what do you think?

I think it's innate to everyone and we're in a society that beats it out of you. So this idea that you can be patient, you could focus, you could put up with the hard stuff. We're born and that's life, right? Why do we cry? For the first year, we're just trying to get what we need, right? We're just like, we'll do whatever we can to fight for what we want and we'll cry all night. We don't care, right? When you're like eight weeks old, then you, at some point, the dopamine hits in, you need the quick fix. You're scrolling through your phone, everything's comfortable, right? And you don't have the ability to even stand in front of a wall and look at a spot, right? And I say that because sometimes Cass says, mike, go look at, go stand next to the wall. Go look at the spot. I'm not letting you in bed until you've done one minute without looking away. And it's just, I just think it's hard for us in this world of instant gratification isn't fast enough asking someone to work just an honest eight hour day without a break, without looking at their phone, doing meaningful work. And the breaks you take are great for nourishment and to rest your brain, right? You may meditate for 10 minutes, you may take a 20 minute power nap, but you're doing it in service to focus and hard work. That's impossible. It's easier for them to run a marathon in seven countries in seven days than to work a productive eight hour day. That's just the world we live in. But they weren't born that way. They've been institutionalized by their environment.

I agree 100%. And I feel as I get older, I get on these rants where we're talking about the softness of society. But I think to your point, 100%, there's an addiction to comfort. There's an addiction to distraction that, that I feel like is so ubiquitous that we can't even recognize how pernicious it is. And then the other thing that is sneaky, that is not addressed enough is that I believe this is new. But we're living in a society where you can get an incredible amount of status and social credit for being ineffective and hurt. And in the past, the only way to get status was by conflict, inferring value and being consistent. But now we can connect online with people who are. Who are not doing well and not saying, hey, I'm not doing well and I want to do better. It's like, hey, I'm not doing well.

Haha.

How poorly are you doing? And now we are gaining status by being worse and less productive.

Well, I mean, and it starts in the home. Let's talk about, you know, talk about a soft couple of generations behind, you know, Mike and me. Where I think parenting has been is almost beyond helicoptering. It's just enabling. It's just 100% enabling with no boundaries. Right. There's the yes machine. Because parents want to be friends with their kids. Right. And I think that's gonna impact the economy so much because we're producing kids who come into the workforce who can't handle a little setback. Right. They can't handle the fact that they, you know, have to, like Mike said, work eight hours within boundaries that are required.

Yeah, It's. It reminds me of a story with, with Whitney. And Whitney is a fantastic parent, and Whitney has very, very high standards as well. So when Whitney wants something done, she wants it done the right way. And the thing about children and their brain development at. And dexterity is that they will always do things wrong. They just can't. It's. It's hard. Right. And so I remember there was one. There have been a couple of times where the kids are clearly, clearly doing something wrong, and Whitney's jumping in to tell them how to do it. Right? And I was like, please do not prevent our sons from having the gift of failure.

We.

We need them to feel that. We need them to be able to identify the problem and find the solution themselves. I. Listen, you're a valedictorian. Honors. I know you know the answer. We need to give our children the ability to find the answer themselves. So I. I think it. You're right. It starts early. And then the thing is too. It's. It is not too late, no matter what Age, you are listening to this to, to make this shift because people can change, we have to develop new habits. And it, it's, it is tough. But again, one of the toughest and most important habits we need to be able to develop is pain tolerance. Feeling that pain and leaning into doing the right thing rather than feeling that pain and recoiling into comfort.

There's only so much you can tell your kids, right? Like when you go talk to your kids, you're not Kwame, your dad, they don't care that you're the founder and CEO of the American Negotiation Institute, and you're like the world's leader in, you know, negotiation. And this TED talk that went viral, all this stuff, right? You're just dead. And so there's nothing you can say that they're gonna like. It's gonna stick. It's gonna be in and out, right? And what we've realized now, that our kids are a little older. So fast forward, youngest is 18, oldest is 23rd. They soak in all of your actions. They pay attention to everything you're doing. So how you respond to failure, how you respond to adversity, how you treat people, how you take care of your body, how you take care of your spouse, right? All of these things which we never really thought we were teaching, that's what stuck. All the conversations where I'm like, oh, you should be a good boy, right? It's like, it doesn't even register. It's not even in there like lexicon. And so to me, it's very comforting, that little conversation where you treat the waiter well, that you have a human interaction, you say thank you. That's more important than a two hour sit down on how to be a man in today's world, which is not easy for a lot of these young guys. So just live your life the way you want your kids. And if you're a yeller, if you hate your kids, they're gonna create like they're gonna have kids and do the same to their kids. And you're gonna continue this multi generational trauma. Whereas if you just kind of be the person who you want your kids to be, they will be that person. And we know it because we have three different kids. They seem like from three different parents, but they're all turning out various degrees of okay, good.

That's what I like to hear. And I think that's, it's so encouraging too, because whoever you are listening to this, the change begins with you. And it's never too late. It's like the The Chinese proverb, they say the the best time to plant a tree was 20 years ago, but the second best time is today. You know, and then once we start to recognize that, then we can start to make these changes. And I think this is a good time to transition into part three because we're doing questions from the listener.

Hey Kwame. I'm the founder of a health tech startup. We've raised a modest pre seed round, got a working MVP and just signed our first pilot with a major hospital system. Sounds great, right? Here's the problem. My co founder and I are completely out of sync. We started as friends and we've known each other for years. But since we launched the company, it feels like we're living in different universes. I'm in the trenches with customers, customers, refining the product, pitching to investors. He's obsessed with the theoretical ideas and keeps going off on tangents about features we don't need right now. We've had a few tough conversations, but he's taking things personally. Now I find myself avoiding him and I'm scared it's going to hurt the company, or worse, our friendship. I don't want to push him out, but I can't keep carrying everything alone either. How do I bring him back into alignment without blowing up the partnership or burning out?

So I have a lot of experience in this and I launched a company with someone who's not Cas, who is a friend, and the exact same thing happened. I'm very commercial. I was focused on how do we get commercial applications. My friend is an artist who invented this technology in his art. It's a new way to encode data using 3D objects and the numbers behind it. And he looked at it as a theoretical innovation project to just come up with more use cases and kind of more applications. And I tried everything and if I had a solution that worked, I would share it. In that scenario, there's only one way, which is you have to break up. Because people don't change. And when you're so far apart in terms of work ethic, vision, what you want to do day to day, and where you want the company to go, I've yet to see co founders come back together in a meaningful way. And we've had a hundred investments, some of them have had co founder relationships and again and again. And you just can't force adults to change. You could say, hey, I don't like how you're thinking about this, or I need you to be more practical. I need you to work harder. But oftentimes especially for men, it's taken as a criticism of who they are, not their behavior. So, you know, I think Tyler is his name. It's not that his co founder is a bad person, just the behavior is destructive to the business. And sometimes when you communicate, you have to make it clear that I still love you, but what you're doing is causing us to succeed. We're not succeeding because of it. And then it becomes very personal. And so I think what I had to do at that company, Shape Matrix, because it was his technology and I had budget control, I stepped away from day to day. I'm still on the board. I approve all of the expenses, and he basically has to report to the board, which I'm a part of. It's harder if you don't have control if you just have two co founders who are basically equal. But Tyler, your time is your most important asset. If it's not happening, go do something else.

He's dead. Right? I mean, it sounds like they hadn't had the difficult conversations, the uncomfortable ones, from the beginning. And if his other co founder isn't really listening and you can't break through that wall, they're going to have to take some drastic measures, unfortunately.

Yep. And so I'm a business lawyer by trade, still associated with a firm, but obviously a and I is my main thing. And one of the things that I would do when I would work with founders, like co founders, before they got started, I would put them through my own personal boot camp and I would treat it like premarital counseling. And my explicit goal was to break these folks up. Because if they're going to break up, I want you to do it right now before we get into the weeds here, you know, have like, push them to have these tough conversations, put them in situations to see how they resolve conflict. And if you can survive that now. Yeah. Then, then we can write the operating agreement, we could work something out, and we can write a better agreement. Because now we've thought through a lot of these things, but a lot of times when it, like in this situation, you get to a point where the we've reached irreconcilable differences, where we're just fundamentally incompatible. And, you know, if you've tried to have conversations and you keep running into the same wall, I don't think it's a loss or a failure to come to that. That conclusion. It's far more damaging to try to push this relationship beyond its, its optimal location, because now we're trying to force an incompatible relationship and we're just hurting each other and hurting the company and most likely hurting people in the company and our clients as we go through it. So I. I agree 100%. I think people need to come to that conclusion a little bit more readily and not take it as an indictment of who they are as person. I think that's one of the things that holds them on. So before we wrap up, I want to make sure that we leave our listeners with something that they can carry along with them after the episode. So, both of you, you've seen the startup journey from every single angle. And if our listeners can remember just one thing from today's conversation that could really change everything for them, what would it be? So I want to. I want to hear from both of you.

Mike, you go first.

I mean, number one is you can do anything. You just can't do everything. So less is more. Focus on what you really want to accomplishment, accomplish. Tune out everything else. And if you do that, you will go from feeling guilty about saying no to loving it. You'll go from being very unconfident, not confident in what you're doing day to day, to knowing that every ounce of work is pushing the cart in the right direction. And you'll just be happier because it'll free up time that you're spending doing stuff that's not moving the needle. So all of your wood behind the right arrow, and the rest takes care of itself.

Oh, that's so good.

Okay, I'm gonna say radical transparency with your communication. So as founders, there shouldn't be and business leaders, there shouldn't be a big wall between you and your team. You need to be telling them all of. All of what's happening. The good, the bad, and the ugly. That is the only way you can create glue, especially in the hard times in the pivots and the changes in the many failures that you're gonna have as a leader and as a founder. So if you have, you know, that kind of transparency, you are going to make better teams that are going to stick with you.

So good. I feel like both of those could have been the start of another podcast, but we have to land a boat. I appreciate this, and I know that there are going to be a lot of listeners who. Who want to learn more about you, stay connected, and, of course, get the book. So what is the best place for them to connect with both of you?

You can definitely just reach us at Cassand, Mike, on any of the handles that you want, you know, on any of the social networks, you can also write in@infoassandmike.com and then the books on Amazon. So we appreciate it and would love the support. So thanks for having us today.

Oh, my pleasure. Y' all were fantastic. Oh, this was so good. Okay, Simone, jump in. Simone always asks one more question. There are things that I miss, so. Okay, all yours.

Oh, I just want to share an experience and then a question for Mike. When I saw your profiles, I am in charge of analyzing the profiles. So when I saw your profile, I went online and I found that. I'm going to show you this sticky note that I have here. It says, is fear holding me back? And Kwame changed my life. That's why I'm working with him. But Mike changed my life because I am a newcomer here. I'm in a different country, and I have fear because everything is different. And there are many things happening that I don't know what is going to happen with me, and I have fear. But then I saw that video, and I said, okay, these people have to be in this show. And I want our listeners to get to know that experience that you have with your heart disease and how you overcame it and what. That's that experience for you. And I would like to hear it again.

Yeah. So thank you so much for watching that video. It was for your listeners. After we sold the business for close to a billion dollars, I was sitting in our office in SoHo, and I'd signed the paperwork, but it was a Sunday, and it was just silent, which we had a very young office. We had a lot of energy. And I just went, you know, it's almost like a sensory deprivation chamber. I went into my head because there wasn't anyone else to, like, talk to. And I just felt an overwhelming sense of gratitude. And a lot of that came from this idea that I was born with a congenital heart defect. I was in heart failure twice before. I was 18 months old. I should have died. It wasn't a time because I'm older than Kwame there. It wasn't. It wasn't a time where you would operate at a, you know, in vitro or kind of a baby. And so it somehow, miraculously, the hole in between my two ventricles closed, which meant I can get oxygenated blood to the rest of my body. And I have known a lot of people who haven't made it. Ben Breedlove had a very similar thing that I had ended up having a premonition and a dream about his death. He was dreaming about a Kid Cudi song, and his story went Viral and Breedlove is the last name and he died and it hit me very hard. And our friend Jen Lynn, who started Cycle for Survival, everyone called her fearless Jen. 12 bouts of chemo and 7 years fight, she ended up not making it. And that's really what I started thinking about is how lucky I was, how thankful I was and how it wasn't until I was able to not shed the fear but not be beholden to it. So the fear will always be there, whether it's a shark, fear of sharks, fear of not being in your country, fear of being an imposter. Whatever the fear is, it's hard to get rid of it because that's your mind, right? That's your emotions. It's not an intellectual thing, it's like an emotional thing. Oh, the shark's not going to eat me. Well, I'm still scared of it, so. But it's how do you make decisions? How do you power forward despite the fear? How do you jump out of the airplane not without fear but knowing that you've prepared and you're ready to open the parachute at the right time. And you know, that's something I've just taken forward because I shouldn't be here, I shouldn't be alive, I shouldn't be with cast, I shouldn't have any of this stuff. And once you start thinking that way, a lot of good things happen. There are two ways to be rich. You could make a lot of money or you could want nothing. And I felt like I was very rich early on because I wanted very little. I'm not saying I don't like having money, but money just amplifies your personal characteristics, good and bad, right? It's not what's going to drive happiness or self fulfillment. So thank you. Long answer, but that was kind of the background of some of that.