Are Your Goals Motivated by Joy or by Fear?

Let me just get this up. Okay. What are you doing?

I thought we clapped before the episode.

That's only in the Brew studio. Now that I'm home, I don't have to do that, but you can still clap. That's cool. What's up, everyone? I'm Alex Lieberman.

Yo, this is Jesse Pujji.

And this is The Crazy Ones. This is one of my favorite episodes of The Crazy Ones yet. And that's because rather than talk about theory or case studies of other businesses, we have 2 of the best CEO coaches in the world giving real-time coaching and real-time feedback on our businesses and our challenges. Matt Mochary, founder of Mochary Method and author of Great CEO Within, has coached some of the most successful startup founders in history, from leaders of AngelList and Coinbase to Sequoia, Plaid, Brex, and Reddit. And Alexis Damacourt is head of coaching at Mochari Method with Matt. He's coached leaders at OpenSea, WME, General Catalyst, Accel, and many more. This episode gets vulnerable, it gets actionable, and it's unlike any episode we've done before. So let's get into it. Matt and Alexis, thank you so much for joining The Crazy Ones.

Thanks for having us here.

So I, I'm going to start with a selfish question that I was wondering before this, and I just can't get it out of my head. So I need to clear space for the other questions, which is, how did you decide that coaching was for you? And I'm going to— I'm going to share some of like the preconceived notions I have of coaching, which is, you know, they say in like— I remember from School of Rock with Jack Black, it was like Those who don't do teach. Those who don't teach teach gym class. How did you guys decide?

Like, it's meaner than that, Alex. It's those who can't do teach.

Yeah, that's right.

Yeah. Way meaner than your version. Yeah.

And so how, how did you guys decide that this fit what you wanted for yourself in your life?

Yeah, let me, let me tell you how it is. I'm not sure I picked coaching. I think coaching picked me. And I like to say to actually my people I coach, I'm like, you know, I've been a founder. I know what it feels like to wake up at 2 in the morning and check out my phone to see if the term sheet has dropped. That sounds all exciting, but here's the other part of it. I tell people I've successfully founded 3 companies and driven them off cliffs. So, I've learned a hell of a lot. From what I've learned from those moments when you go, oh, it's, it's not going great. But I always came through the other side. And I think since I was a kid, I've always gravitated towards coaching. And so yeah, coaching picked me.

Matt, what about for you?

Not dissimilar in that I was a I'll get a little more tactical in that. I had sold my first company when I was probably early 30s, and that was it. And then, I went and had fun. And then, I had so much fun, I didn't want to have fun anymore. And then, I said, well, what else is there? I guess I'll go do good. And so, I went and did social good, and I went and did so much good. I was like, actually, that part was awesome. I wanted to keep doing it. But then, I moved back to California. And we, my, we started a family there, wanted to raise our kids there.

Wow.

And when I was there, I wanted to get back connected to my, my peers, my friends. And they were all working hard in the tech industry, and none of them wanted to join me in, like, helping ex-convicts. And so they all thought I was crazy. They thought I'd get killed. So I realized, ooh, if I want to hang out with my buddies, I got to go back into their world, which is the tech world. But I don't want to start another company because that just makes more money, and I don't want or need that. And so is there some way I I could enter into this world and just do the fun stuff. And then I heard about this guy, Bill Campbell, and I thought, wow, what he's doing, that looks really fun. He's getting to do all the fun stuff and none of the hard work. I'd love to do that. But of course, I wasn't a coach. And so I thought, well, who would want me to coach them? And I thought, well, the only people that would want me are the people who can't get anybody else to coach them. And so there's a student at Stanford that came to me and said, hey, would you coach my roommates? And I was like, okay, that sounds right. Students, 18-year-old kids at Stanford, that sounds about my speed. And so, that's what I did. And it turned out to be way better than I even imagined.

What a great story.

I wish I had said all that.

I was coaching my wife and yeah.

Matt, for you, I mean, you'd had a successful exit. Some people do that, then they go for something bigger next or they go They built something out. Like, I'm curious how that fork in the road for you or how— why you didn't end up starting another business or buying businesses or— because I think, you know, Alex and I are part of a lot of these post-exit. Both of us have sort of been— we've been through that. And I think it's very here and now for both of us as to how we spend the rest of our time because we're in that same boat. So I'm curious how that— the thought process for you.

Hmm.

That's a really good question. Like, why not? Why not just go create more? Well, oddly enough, now Alexis and I both are, so that— but it's coming from a different lens. You know, before it was— I felt the first time I made money, it was fear-based. It was, I will be a failure if I don't make X million dollars. And so every day— and it fueled your fear. Fear is a great motivator. It's toxic. But it's it's very compelling, and so now of course joy is equally compelling but non-toxic. So that's like a way to succeed and have a great life is to be joy-based. But I wasn't back then; I was fear-based. And after I sold or sold my piece of that first company, it was just a relief. I just want to take some time off. I just wanted to go surf. There was no more thought than that. And then once I started surfing, I was like. Oh, this is actually really good. And after about 2 years of that, I realized I hadn't spent a penny and I had just— my net worth was just as much as it was 2 years before. And then I thought, wait a second, I don't have to make more money. Like, it's literally over. And of course, that was pre-kids. So, the story changed once I had kids.

Adjust for child inflation.

Exactly. And then, so that was really, I don't think it was really sort of a, hey, I'm going to do something better than everybody else. I'm not going to go make more money. I'm going to go have fun. No, it wasn't conscious that way. It was just coincidental. But now, having made money, then having gone and had a ton of fun, then having gone and done social good, I think those are, and maybe there's a 4th piece of the wheel, which is getting conscious, understanding how the mind works. And realizing that my amygdala, when it gets triggered, takes over when I'm in fear, anger, and just like makes me into a crazy person. And sort of understanding that more and more and being able to shift out of that when it occurs more and more. Not perfect. I'm not perfect by any stretch of the imagination, but I'm getting better each, each day. I think those to me are sort of like the 4 pillars of a life well lived. And so now the challenge is, can Alexis and I do all of those? At the same time. Because for me, before it was serial. I'll do— I'm only focused on making money. Now I'm only focused on having fun. Now I'm only focused on doing good. Now I'm only focused on consciousness. And now it's, well, let's see if we can do all those at the same time. And the making money part isn't off of coaching. It's that we're coaching people to build $100 billion businesses. But unless we have built a $100 billion business, then we don't actually know all of the step-by-step mechanics. We know them theoretically, but not practically. This goes back to the Jack Black comment. And so there should be— I mean, there's a system by which you manage a scaled company. Amazon has it, Google has it, et cetera. We've written that in Google Doc form that you know about. We share that with the CEOs that we coach. We implement it in one-on-ones where We coach the CEO and the CEO after 3 meetings goes, oh, wow, I feel more empowered, more engaged. And then we say, oh, great, if you like that system, now you can implement it in your whole company. But it's in Google Doc form. And the CEO says, well, it took you 3 meetings with me and I've got 1,000 employees. Does that mean I have to do 3 meetings with each person? I mean, that's like thousands and thousands of hours. And they say, well, can you just please write software so we can just press a button and have it run the whole company? So, that's what we're engaged in now. And of course, if that works, That should clearly be a $100 billion company. If Salesforce is a $200 billion company and it runs the sales team, an entity that runs the entire company should be worth more. But we're also, by doing this, by building the software, we're now engaged in company building again. And so Alexis is running a product team, a new product team, and he has absolute insight because he gets to experiment. with how to— what makes a new product team successful. And then he can share that direct knowledge. It's not theoretical anymore with the CEOs he coaches, because also creating new product in a scaled company is very difficult. And now Alexis has direct knowledge about that as well. And so it basically creates a laboratory for us where we can test our own most radical ideas And see whether or not they work. And by the way, they don't all work. And our most radical ideas, no one else will test. Like, we can share with our CEOs, hey, I think you should try blank. And the first question they ask is, well, who else has done this? And if the answer is, well, nobody, you'd be the first, then usually they go, eh, I'll pass. I'll do something that's tried and true. So if we really want to be innovators as coaches and as teachers of how to build companies, we have to have our own—

Yeah.

Laboratory, which now we do.

Love it. That's awesome. I want to go back to one thing you talked about, kind of this shift from fear to joy. And I mentioned to you, I work with a coach who you work with also. So we're coaching cousins. And the first time that the concept was introduced to me, I had never heard it and it really kind of blew my mind. I didn't appreciate how much I was using fear to motivate myself. And gone through this whole journey. Took me a year plus to kind of give it, give it up. And, you know, you obviously sold your company. I talked to a lot of entrepreneurs about this. You know, this show is called The Crazy Ones. It's sort of the ode to the Steve Jobs quote of like the people who are crazy enough to kind of, you know, so it's all about entrepreneurs. A bunch of people listening, I think, are in the same boat. The biggest pushback I get, Matt, is like easy for you to say you sold your company, you made a pile of cash. Easy for you to say that you shouldn't use fear to motivate yourself anymore. And of course you don't have to because now you've got all this money and you don't really like— like you said, there was still that amount of money. What do you say to people in that situation? Like, you know, how do you approach that conversation? Maybe, Alexis, we can hear from your version of it. But because I think it's— I have my answers, but I'm curious how you guys respond because it's a fair— it's a fair pushback, I think, for the— for the post-exit entrepreneur to go, yeah, you're so in fear. You know, you entrepreneur, like you stop being so fearful, be joyful. And like, yeah, uh huh. Because I was the same way. I ran that whole business in fear as well.

I think from taking on this product role internally, where I work with a team, and then I'll go and speak to Matt about it. And it gives me this kind of perspective of, hey, I'm not the CEO of a company any longer. I'm here.

And so.

My point is with CEOs now is I know how your team thinks. I know how this, how we build up a company again from those who are in it. And then the fear part is saying, hey, I know what this is and it's not always just a perfect outcome. Like, use this framework. Oh, it's going to work awesome. And then say thanks a lot and walk away. It's given me the insight again and the reminder that a lot of these things we can say, Fear, but if you don't go through it yourself, if you haven't come through to the other side, right? It's very hard to go and just say, "Hey, use this framework." I read it in a book. So I use this with people, which is I know exactly what you're going through. And at times I'll be like, "I'm literally working with a product team right now." And you see my my the CEOs I work with their eyes open up. They go, "Oh, so you know what this struggle is day to day." Right. I'm like, yeah, absolutely. And so, when I say it's fear-based, I tap into where that fear is coming from me and I fall below the line and then I go back up and I bounce along. But again, the story to me is like I won't recommend something to one of my colleagues or one of the CEOs I work with if I haven't been going through it and if I'm not using it at that time right now. So that to me is the most important thing.

I mean, one of the pushbacks you get is, is some people even say this on Twitter and stuff is like, chips on shoulders put chips in pockets. Like, I have friends who will even— they'll acknowledge they're using fear, but they'll say, no, I can't. I, I want my fear. I want— that's my edge. That's how I— and, and so, yeah, I'm just curious, how do you— I don't know, Matt, what do you say to people in that situation?

Um, 2 things come to mind. One is that, um, yeah, it's a fair criticism of me. That it's easy for me. Agreed. You know, guilty as charged. But what I usually do is I'll make a bet with someone. It's like, okay, I perceive you to be in fear around this situation. And I say, let's make a bet as to what the outcome actually is. Let's see. First of all, yes, fear is motivating you, but is it causing you to make good decisions? So let's take a thing that you're feeling concerned about. You predict what you think will happen. Like you do A. and then you predict that B will happen. I'll listen to what you say. Dollars to donuts, I'll predict that C will happen, which is like the opposite of B. And then let's just test it. Let's just see who's right. And then people usually say, okay, I'll make a bet with you. And then they do. And then I've made those bets hundreds of times. I have yet to lose. And it's nothing magical. It's just that, again, their brain isn't working as well. So now they realize, oh, when I'm in fear, my prediction skills Aren't as good. So then that's usually a moment where they go, oh wow! Now I'm really into this coaching. You know, now please share point out other places where I'm in fear. But in terms of motivation, yeah, it's pretty darn effective, and it gets you up in the morning. It gets you working each day. You know, 18 hours if that's what's needed. And there are many times when people say to me, Matt, I would like to get rid of this fear, and there are ways to do it. There are literally techniques. to quiet the amygdala and through meditation, through breathwork, through plant medicine, all kinds of ways. And they're effective, they work. And the warning I give to people is before you do that, let's actually start building in actual joy into your day-to-day because I have had the experience of CEOs that I coach effectively turning off their fear and then going, yeah, I don't want to run this company anymore. I don't want to show up at work anymore. I'm like, whoa, no, wait a second. That wasn't what we wanted to do. And then, we have to build joy back in. And there is a technique for building joy in, and it's the energy audit, which is incredibly effective at building joy into the day-to-day by removing the things that are painful. And, of course, what will fill that time is things that are more joyful or certainly not painful. And it usually takes about 60 days to really build that joy in. But for now, I say if someone wants to go through the technique of, removing the fear, at least the people I coach, I say, let's build in joy first. So there isn't this canyon of demotivation. And instead, if we get you to be joyful and fearful, then when the fear drops out, the joy keeps going. You keep showing up to work excited, et cetera.

But I also see— I've got clients who've been like, I'm fear. Absolutely. But it's not like they're calling me from Yosemite and they're like, a grizzly's chasing me. I'm going to go attack it. It's not like, hey, I don't have fear for this. It's fear in the corporate setting. And I often find like today I did an energy audit with somebody and they were like, I've been thinking about this for years. How can I feed this up? And we just moved a meeting and we put some colors in the meetings and we said, oh, don't worry about this. I have Tuesday meetings all day. What do I do on Wednesday? I'm worried about my email. And I was like, just set aside an hour. in the morning. And it was like, it was like this guy was like, here we go. This is such a simple, easy solution. And the thing is, I'm like, now we're speaking the same language to each other. And it was this kind of cathartic moment for him. And I loved it. I love seeing this kind of awakening within that it was a simple solution. And we were speaking the same language.

So the big thing for, for me, actually, in talking about fear versus joy is actually the consciousness of which one is motivating me, because to me, at times it's very, very difficult to decide or to know, because I think sometimes we're so good at masking what is fear-based versus what is actually done for joy. And so I'm just going to play out a story for you guys, and I'd just be interested to hear how you would react to this.

So, Alex, is this live right now? I say we do something. Yes, that's present right now.

Yes, it is present. It's going to provide a little bit of backstory and then come right into the present of like a present question I'm asking myself. So, excellent. October of 2020, we sell the majority of Morning Brew to Axel Springer. April of 2021, I step out of the CEO role, out of being— after being in the role for called 5 and a Half Years. The moments after stepping out of that role were some of, I would, I would say, the most difficult times of my life. I felt purposeless. I felt directionless. I didn't know what I was going to do with my time. I felt like a lot of the things that had motivated me prior for Morning Brew, namely money being, I would say, 70% of what contributed to my drive with Morning Brew, was no longer there. And I also had a lot of guilt of feeling like I was inadequate in the CEO role. I told myself the story of that is why I'm no longer in the role, because I wasn't good enough to scale with the business. I told myself that I was only good in 0 to 1, but I didn't have enough focus in order to like actually continue to build out as an operational CEO versus just a builder in chief. And I had the story of myself that it was a lot of luck and my co-founder just kind of pulled me along for the ride. And so then push the story forward. You know, I am basically staring at the sky for 6 months straight, reading a lot of books on stoicism, doing everything that a cliché exited founder does. And ultimately I say to myself, okay, I'm going to start a startup studio because the things that I've told myself that I love and that I'm very good at are ideating, building products, taking them to market. But like everything after that, the company building part, I'm going to outsource that to someone else. And one of the other justifications of that story of why building a startup studio was right for me is I think the two things I'm good at are sales and starting businesses. And because when I think back to the early days of Morning Brew and the lack of life that I have, I am no longer where I am at my am in my life going to be willing to make that trade-off again? And so the story I've told myself is building out a studio is going to give me the balance I so desire and lean into the things that I believe I'm good at and outsource the things I'm not good at. And I'm asking myself the very question right now, which is this idea of building out a startup studio, how much of it is driven by the joy I have in building early-stage businesses and getting my hands dirty? And how much is driven by fear? The fear of becoming irrelevant, the fear of losing my network as an entrepreneur and a startup founder. How much of this is driven by I have to build something right now to keep my relevancy and keep my— call it social currency and value in this space versus it actually being driven by the joy of building businesses and my ability to answer that question right now. I would say I don't have that ability.

Okay, that, that's a little bit theoretical, Alex. We're gonna— we're gonna— I'm gonna box you into something very practical and very real. And so, a few questions. One, are you having fun?

I believe I'm having fun.

Then there's no problem. I want to find a real problem. I want to find— I don't want to— I don't want to talk about some Academically is this. I want to find something that where you're not having fun, where you have— where you're like, holy shit, I've got— this person is not performing. I don't know what to do. They're screwing up.

What do I— how do I—

but they're key.

If I lose them, like, I want to give them feedback, but if I— they're so sensitive, and if I do give them feedback, then they're just going to rage quit, and then I'm screwed. Like, that's a problem.

Larry— The one thing, if I may, for on Alex's behalf, since I know him pretty well, like I would say that, and again, using my, my limited coaching knowledge and experience, like he is below the line about— he's not like 100% into what he's doing because he has these, like, he's, he's creating a problem like that, which is he's not— he doesn't trust his own motivations around why he's doing what he's doing. So he doesn't let him show up fully. to be this venture studio. Like, he's been— since I've known him, he's been a little in neutral with this thing. And he talks to me and he asks me questions and I'm doing it a little further along. And, and there's something in his head that's telling him he's a charlatan for doing a venture studio. I'm putting words in your mouth, Alex. Yeah, but like, but I think that's actually the big problem, which is he feels like a charlatan by not being a CEO and founder versus a studio guy or something like that. I'm making that up.

Yeah. And I totally respect that point. Like, if I'm having fun, why even ask the question? My thought is I was having fun for a lot of the period of building Morning Brew. But I would say in retrospect, a lot of that fun was driven by the fear of the business not succeeding and not making a lot of money with the business to take care of my family. That was the story in my head. And so I guess the question is, is I'm worried that while I may be having fun today, do I— am I motivated by an actual love for building businesses that will make me want to feel like I'm having fun a year from now, 2 years from now? And maybe your answer is, well, worry about that shit when it happens in the future.

No, no.

But that is my feeling.

Yeah. So what I'm hearing is, Alexis and Matt, I feel fear that a year from now I'm going to wake up and I'm no longer going to be having fun. And I feel fear that, that I don't really enjoy this studio stuff. That I'm not really good at it, and that one day I'll wake up and go, what the fuck? I just wasted X years of my life doing something that I'm crappy at, and that was totally pointless, and I just lost all of those years. Is that close?

Yes.

One of the key things of allowing people to be open to hearing other thoughts is making sure that the person that they're talking to actually understands them. If I feel like you understand me, then I'm open to hearing what you say. But if I think that you don't understand what I'm— my position, and then you start giving me advice, then it just sounds like canned advice for like the masses. So, a key thing in creating trust is reflecting back what the person— the situation the person is in until they say, yes, that's it, which is what I did with you, Alex.

Yeah.

And you can use this in sales, you can use this in fundraising, you can use this in In employee management. You can use it with every human being that you interact with. If you acknowledge back what they're telling you, you'll notice a much deeper connection much more quickly. But let's now jump in.

For the formulaic founders listening, Matt, because I'm a formulaic— like, I need, I need to be spoon-fed. In your book, it's like the 4 words or 5 words, what I hear you saying is, and then literally repeat back word for word what that person is saying. And I've been practicing that with my wife and I've been practicing that with each other to make sure that we're actually hearing and being like, but that, that just like for anyone listening, don't share your opinion after, say what I hear you saying in first. And by the way, the second thing I'd add to it as someone who's learning it still and getting better every day at it is it actually does make me consider more of what they're saying than I think I otherwise would.

Right.

Because I have the other dialogue in my own head. So then I say it, I'm like, oh yeah, okay, that's what they're saying. And anyway, it's a great hack for every part of listening.

Awesome, Jesse. And I love that you're practicing it. And I would say that the repeating back word for word is sort of like the entry-level version.

Yeah.

And the advanced version would be now putting yourself— imagine the emotion that person's feeling. Let's say they're feeling fear or anger, whatever it is. Sort of feel that emotion and then imagine what thoughts you would have if you were in that same position, and then share those thoughts, which are going to be much more explicit, much bigger, And then when you— that's the advanced version. And when you do that, the person, instead of saying, yeah, that's right, they'll say, whoa, yeah, that's it. Because then they see that you understand their emotion, their— and you're also able to say things that they didn't even think about. But when you say them, like, yeah, that's actually true. So let's come back now, Alex, to your situation. So this is a perfect— I mean, anytime there's fear, And you're just saying explicitly, I worry. Worry is the same thing as fear. It's something that will happen in the future, and I'm making a prediction about it that is negative. By the way, fear is the sister of excitement, which is also making a prediction about the future, but is predicting that it will be positive. You don't actually know what's going to happen in the future. Could be negative, could be positive. So your fear could easily be turned into excitement If you start thinking about things that good that will happen in the future around the same issue. But let's see which it is. And the problem with predict— being fearful of something that's years out is that you won't know for years what the result is.

Yeah.

So, let's pick something a little bit shorter timeframe and let's see if you are— one, we could sort of play out theoretically what it would be like if it turns out you're crappy at this. And we can say, well, is that really a bad situation?

Yeah.

Before, before we play out the theoretical with me, I guess, Jesse, is there anything that feels like super topical for you right now that's like a real problem that you're open to discussing? If not, we can play out mine.

No. Yeah, let's do yours. I'm good.

Okay.

Do you have fear about something?

I talked to Dave yesterday.

What's your fear about?

For the next 48 hours, I'm good.

Then I'll— So coming back to this, I just like to— again, I'd like to go back to this, the baseline of making a bet with you. Let's just see if generally your fear is making good predictions, Alex. But let's pick something shorter. Can we pick something that you fear is going to happen this week? And again, this is a proxy. If we can test it this week, then we can apply it to this, the fear that you have over years.

Yep.

But there's no way to really test the year-long prediction. So let's test the 1-week prediction.

Yeah. So, and what would an example be of a 1-week prediction? Just—

Anything that if you— that you don't want to do, because if you do it, you think something bad will happen, and then you'll get the results this week.

Okay, I'll just take one of the businesses right now that I'm building in the studio. Which is my, my dream. Something I know I love is being playful and playing games. That is something I know I love. And so one thing that I'm building with a partner right now is the idea is Nerf for adults. What would it look like to have a portfolio of game and toy products for adults so they can take their lives less seriously and The first product we're working on is something called The Plunge. It is quite literally a backyard plunger throwing game where you throw plungers like axes and they stick to the board. And the fear— I have 2 fears right now. One fear is my, my partner today sent me the invoice for the new boards we're getting from China. It's like $1,000 for the boards and the shipping. And I just in my head visualize the amount of dollars I've spent on this game so far before us knowing if this game is actually going to be something that people enjoy. It's at like $37,000 right now. And I feel so much anxiety around the fact that I've spent $37,000 on a product. And it sounds crazy to some people, but I feel so much anxiety for spending $37,000 on a product that doesn't yet have a proven audience. And I don't know if this thing is even going to sell. At the same time, my fear is that we're going to be launching this thing on Kickstarter in the next, let's call it month for— or if we want to say week, week, but in the next month. And my fear is that it's not going to succeed in the Kickstarter campaign. And all of the people who hit me up on Twitter basically saying, you're a schmuck, you haven't taken a nearly big enough swing as your second business that you're building. What are you doing with your time? 18 months from now, you're going to regret having spent time building a plunger throwing business. My fear is that they are going to be right, which then induces my own fear of like, this kind of half foot in, one foot out of, am I actually spending my time on the right thing? Like, are they right that like I am not using my time wisely? Like, this is what I'm doing with my abilities. And so those are kind of a number of feelings I feel around building this product right now.

Okay, sounds like 2 fears. One is I'm spending— I've already spent $37,000 and I haven't seen one person interact with this game yet, not with any prototype, not nothing, not with like a stick, you know, duct taped together with a piece of foam, nothing. So, and I'm gonna only see the results 30 days from now. And I predict that people aren't gonna like it. They're gonna fucking hate it. Is that right? Is that one?

Only clarification is the game has been built. We have ambassadors who are actually hosting games in their cities. So people have played the game, but no one has actually paid the full dollar amount for the game yet. So I don't have I don't— there's a difference between playing the game and someone actually putting their hard-earned money down and buying the game, and that hasn't been validated yet.

Okay. And so I needed— I have people who've used it who said, oh my gosh, this is so much fun.

Yep.

But they haven't paid any money. In fact, I may even be paying them to go and spread the word. And now we're making a run, uh, we'll build 1,000 of these things, and then we're going to put them up for sale. And my prediction is No one's going to buy them.

Yep. And if that happens, my fear is I won't have, I guess, enough money or it will have been a really stupid way for me. If my goal in life is to not be an idiot and keep myself rich, this is a really good way to not commit to that goal.

Mm.

Got it. So if I keep doing things like this—

Yes.

This one, $37,000 isn't going to break the bank.

Yep.

But I have other overhead and expenses around this startup studio. And if I keep doing potshots that all fail, Then the whole expense of the studio will have been gone. I can probably afford that, but it will degrade my lifestyle a bit.

Yep, that's the fear. And it's the fear that this validates the story I had that I'm actually not that great of an entrepreneur and that I was just lucky with my first at-bat.

Okay, I'm ready to make a bet with you right now.

Okay.

What do you predict will actually— actually, actually predict will happen around sales, of this first toy and around not what people will say, because people are going to say negative stuff on Twitter no matter what. It's how you're going to feel when it gets said about you on Twitter.

Yeah.

So my prediction on sales is that we're going to sell at least $50,000 worth of The game.

Wait a second, that's more than you paid for it.

Yes, but I haven't paid to manufacture those boards yet. So, so yes, like there will be— so really, but what I'm making from those games, if I sell $50,000, I'm not making $50,000. I'm making whatever the difference is between the cost of making those games and what people paid me. I don't fully know if that will— that first run will actually pay back my full investment. But yes, but yes. So I think it's 335 games. The game sells for $149. I think that we'll sell $50,000 worth of games.

Yeah, but, but, but Alex, that feels like a win to me. If you sell $50,000 worth of games in your first run, that feels like you at least got people to test it. You got people curious enough to buy it. Now, if they go and recommend it and say this sucks and no one else should buy it, okay, it didn't work. But I'm missing where the failure prediction is.

Can I take a crack?

Yes.

I think that the failure worry is people will say, great, you were a success at this, but you made a plunger game.

Yeah.

And the plunger game, and by the way, I can't believe both of you have not used the word plunge or pun.

So look, that's the name of the game is the plunge. Oh, I love it.

I'll be buying one.

Love it.

But here's the thing, and I know Matt will because he loves games, but here it is, is that I think you're actually saying is, yeah, it's great. It's going to be a success, whatever, $37,000. Yeah, that's significant. But I'm afraid on Twitter, people are going to be like, you sold your company in 2020 for X. Wow. But wait, your follow-up is a plunger game?

Yeah.

And even if it made $10 million, they'd be like, great, it's a plunger game.

I think, I think as we're talking through it, that's like, I think the money thing is like, is just an anxiety of mine, like a, you know, based on years of just like nurture. But I think as we talk about it, yeah, this, this fear of Basically being judged for not, not taking a big enough swing, which I internalize to myself as Alex. What you're, you're shorting yourself of your potential. I think that's how it gets translated to myself.

I think it's also a story you're telling yourself of, hey, so this one time I sold this company, it was because someone dragged me along and it was a miracle.

Yeah.

You know, I could have been doing something else. And here I am, I don't have that person with me. And my next venture is the Plunger Game, which is great because I really believe in playfulness for adults. Who, what? I mean, that's great. You said Nerf for adults. I'm like, yeah, I would play that. But you're also, I think, this real deep concern, which is, oh man, this is my follow-up. And if I'm not with my co-founder from before, people are just going to validate my own fear that, you know what, I lucked into this. And fear's telling you that right now.

Yeah, I think that is pretty spot on.

So by the way, this is why Alexis is better than I am. And so there's proof. But I still do want to make a bet with you. And so Alexis nailed it. So your prediction is that it will work and then people say it's irrelevant and you'll feel like you are irrelevant because people will say it's irrelevant. Yep.

And then I get mad. Yeah. And then I get mad at myself for even giving a shit of the fear of being irrelevant.

Inception level right now.

We're like 6 levels deep. Yeah. Alexis is glitching out right now.

So I'm gonna, I'll make a bet with you on that.

Okay.

And this is so subjective. It's how you feel. You're going to predict again that it's going to make some amount of success and that you'll feel stupid because you'll realize then how irrelevant this game is. Is that right? Or this entity, this project is.

Yes. Okay, great.

I'm going to predict the opposite. I'm going to predict that it will have whatever amount of success it has, whether I'm actually going to even within the realm of total failure, like no one buys it. And my prediction is your feeling will be, I'm glad I did it. I'm glad I did something from start to finish, A, on my own without my other co-founder who I attribute all success of Morning Brew to, because now I know what I, at least on one situation, which is not always, it's not always going to be the case, but at least one situation, what the outcome was. And money here doesn't matter to me. I'm doing this for my purpose is something completely different. It's to create fun and also to see whether or not to learn, to understand what it's like for me to do this on my own. And I achieved all those things. I learned it was a great experience. Now, I may get to go do something different, but I'm glad I did it and I don't feel like an idiot for having done it. That's my prediction of how you'll feel. You can game that bet. Because you can, like, a year later, whenever it happens, you can say, no, Matt, I feel stupid. Okay, but I believe you'll tell me the truth. And I believe that you'll look back and say, that was worth trying. You ready to make that bet with me?

Yeah, I have my calendar up. I was going to put down a date to remind myself to hit you up on the result of the bet.

Now, here's the thing. The reward for this bet is pretty steep. The reward is whoever wins, The next time you're in fear or perceived to be in fear, that person gets to decide what you do. So if I in the future say, hey, you know what, Alex, I think you're in fear now, and if I've won that last bet, then whatever I recommend you do, that's what you got to do, because we are— we'll know that your brain isn't working well at that time. Now, if you win and you feel shitty and stupid and feel like an idiot for having done this, great. You can make all the decisions going forward.

Yeah, I'm willing to take that bet.

Okay, great. Let's reconvene in a year.

Oh wait, is this the first time Matt has given you guidance, Alex?

We were talking about this before, before the conversation a little bit, and you know, I'm trying to remember what the exact conversation is, but I— if I remember correctly, I I spoke to one of Matt's clients or people. Can I say he's a client?

Sure. Alex McCaw, but close friend.

Yeah.

Everyone I coach is a close friend.

Yeah, a close friend of Matt's. And the reason was I actually— I had moved into the executive chairman role at Morning Brew and I was like, what do I do now? And Alex was the first guy that I spoke to because he had just moved out of Clearbit. And he gave me a bunch of great advice and he's like, by the way, if you, if you're interested, you should talk to my coach. And Matt and I spoke. And actually, it's so funny how memories come up based on things that happen. I didn't remember a lot of our conversation, but as you brought up the bet, I remember we made some bet back then around like the Morning Brew outcome and me being chairman. I wish I knew today what that exact bet was, but I knew we made a bet. Oh man, we should have had the results already.

All right, you got to write this one down.

Exactly.

So the commonality here is every time you talk to Matt, you do really have a great outcome with your business.

Yeah, as we were saying before, you know, Matt should be asking me for the finder's fee on the Brew deal. But no, I think that You know, what I find interesting is like, obviously there's a lot of value in what you just said around like the, like the not just the bet you made, but like your quote unquote conviction in the bet, given that there's a lot of power given to the person who wins the bet. But to me, I almost find like as helpful as like making this bet and calling out the fear is actually just like the articulation of these thoughts that stay within my head. And then just like a few good questions causing this flow of thoughts that kind of just clarifies my own thinking. Because I've even found for myself, like, they're like my co-founder, other people I know, they're very good at thinking through things within like their ears, whereas for me, I have to talk through everything to figure it out. And so I think just that in itself is such an amazing provider of value.

Yeah. Well, I think what happens is the brain wants to remember these thoughts that are swirling around in the head. And if you don't say it out loud, then they just continue to swirl because the brain's literally trying to remember them. But once you say them out loud, if you either— if you write it down or you say it to another human, the brain kind of goes, okay, that information is stored Externally, I can always access it again. Now the brain gives itself permission to go on to the next level of thinking. And of course, if you get it reflected back to you, that's when the brain really goes, yes, like, this information is out there. Now I can keep moving. And so, yeah, I completely agree with you. Allowing your— giving your brain the construct to know that that first level of thought is somehow documented in the world. So you can go on to the next step is super valuable. Can I do a little logistical thing? I— this was put on my calendar and I've got literally something in 1 minute and I so apologize. I wish we could just keep going. Alexis, hopefully you can keep going. I unfortunately have to jump off.

No worries at all. Yeah, no worries at all.

Awesome.

Great talking to you guys. Okay. Thank you.

See you, Matt.

Right on. Bye now.

So, Alex, I want to tell you what you're— I want to share with you what your tell was when you were recounting everything from, hey, this playful and playing games, everything. You said a bunch of times, and this is your tell, I told myself. So when you, you know, there's no coach with you, nothing. But when you tell a story and you say, I told myself, that's the fear talking. That's that moment when you're like, oh, I was telling myself. This thing, and you said those three words like four or five times. I told myself. I told myself. So that means some voice in your head is telling you this, and it's that voice that says, "Watch out! Watch out! I bet you're gonna fail. I bet those things I've told myself in the past are true." And that's what I picked up a bunch of times when you said, "I told myself," and that's why I was like, "It's not about the thirty-seven k." Yep. It's something else there.

Totally. Well, this was awesome, Alexis. It was awesome to meet you and just get a glimpse into the wisdom that you and Matt have and just like the power that coaching and honestly just intentional conversation can have. So, we're super appreciative of your guys' time. Yeah.

Thank you, guys. It was really nice to meet you. And, uh, hope to see you guys again. And, uh, this was fun.

Yeah, man. Thanks so much for the time.