This Week in Startups - E1020: CEO/Investor Coach & Author Matt Mochary shares insights on developing his coaching method, understanding & overcoming primal fear, addressing imposter syndrome & more

Episode Date: January 21, 2020

0:01 Calling all writers! Apply to be the first TWiST Archivist at twistarchivist.com 2:42 Jason intros CEO Coach & Author Matt Mochary 4:49 How and why did Matt decide to become a CEO coach? 8:32 What is the secret to being a great coach for investors & CEOs? 12:12 Drawing feedback out of employees 19:27 How to differentiate healthy fear from paralyzing fear? 32:06 How is Matt's method structured? 34:52 Understanding & dealing with imposter syndrome 40:27 Differences between coaching Gen-X & Millennials 42:33 Starting the Mochary foundation helping formerly incarcerated people get & keep legitimate jobs 48:19 Understanding negative motivation and transforming into purpose-filled motivation 52:39 What is Matt's "Shadow CEO" Method 54:04 What does Matt charge? 54:52 Matt coaches Jason live on air

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Thanks for tuning into this week and startups. I'm your host, Jason Kalakanis. And if you're listening, you're either an investor, a founder, or you're considering being one of those two things at some point in your life. One of the hardest things to do in this world is to be the CEO of a company. Why is it so hard? Well, you have the weight of the world on your shoulders and the knowledge that seven out of ten times startups fail. And they fail hard, and it's brutal on the founder because the founder has gone out in the world, put themselves at risk and told everybody, I'm going to change the world through this startup by creating this product or service. And I'm going to complete this mission.

And you convince investors and you convince yourself. And you convince your friends and your family, perhaps your spouse, your parents. and a ton of employees to go on this crazy journey with you. And then you crash and burn. And it is brutal. And sadly, it throws people into depression. It throws people into anxiety. And so what's the solution to this?

Well, the solution to this is to talk to people. And to realize you're not alone in this journey, in these feelings. This is common. The good news is, like a video game, if you fail, you can just start again. at least here in America, the cost of failure is that you earn the right to try again. But that doesn't help people in the moment. That doesn't help imposter syndrome. It doesn't help anxiety.

It doesn't help the grinding of the teeth that you yourself may have experienced, staring at the staring at the ceiling every night going, am I going to run out of money? Are people going to think I'm a fraud? Am I going to embarrass myself in front of the world? Well, Matt is here. Moshari, I got it right. Got it right.

Welcome to the program. Matt Moshari is the second coach to ever appear on this week in startups. Jerry Colonna was on the pod. And I love talking to coaches. Alex McCaw from Clearbit was on episode 996. And he mentioned you. And he said he had a big unlock. He said he didn't know what he was doing.

He felt a little lost. And you coached him. When did you become a coach? And why did you do you do? decide to become one. Great question. So I've been an investor. I was a partner in investment firm here in the Valley. And then I became a founder myself when I started a company. I sold it about 18 years ago. So I've been on both sides of the coin. And then I took a bunch of time off just because I monetized and didn't need to make more money and moved to Brazil, New York. And then an

Avenger ended up coming back to Silicon Valley and realized that I wanted to sort of get connected to the community again. But I didn't want to start another company because the result. of starting another company is one, it results in more money, which I didn't need or want. And two, it's a lot of work, which I also didn't need or want. So I thought to myself, how can I connect into the ecosystem, but only do the fun part? And I thought, well, wait a second, if I just coach, that's all the fun part. And that's none of the work. So let's see if I can do that.

But I also assumed I'm not a coach. So therefore, who's going to want me to coach them? Well, it's only the people that no one else will coach. And so who will no one coach? Well, no one will coach students while they're still students at university. So YC famously will not accept students into the YC cohort. So I went on to Stanford campus, a guy named Chris Barber, who was then a student, invited me on. He said, listen, I've got five roommates.

They've all started companies. They're all real businesses. But no one will coach them? Will you coach them? And I said, okay, I'll try it. And so I did. And it was just super fun. It was everything I imagined.

It was all the fun, none of the work. They did all the work. but they thanked me and gave me credit or part credit for all the success that they had. So that's really where it started. And is there some training you went through to coach, or is it just the school of Hard Knocks and being a great listener? What makes for a great coach in your experience? And now, how long have you been doing it and how many people have you coached? So about six years probably coached about, it's called 100 people.

Okay. And the, so in terms of schooling, in terms of the business side, no. No, that's just my own experience. Right. In terms of the softer, I call that the hard skill side. Right. Tactical stuff? Exactly.

In terms of both strategy and tactical implementation. Got it. And we can get into more detail about what that means. High level and then on the ground. Exactly. And but then on the softer side, which is what you were talking about in your introduction about the emotional awareness, the depression, the anxiety, not acting on the fear and anger that appear, that I did take courses on.

And I took, I sort of immersed myself in it. I took courses from conscious leadership and Hendricks Institute and coaches training workshop. I don't even remember what the name institute or something like that. And like basically every course I could see and think of. And I just enjoyed it. I just sucked it up because I had never had any awareness of that emotional side. And so I think that I, you know, there are different types of coaches. Most, so you either get that soft skill side or that hard skill side.

I may be one of the few that sort of blends both. I don't know. I don't really sort of look at what other people are doing, but I just sort of hear anecdotally. And in the tactical side, I think we get that. People give a lot of advice. There are mentors out there doing it. Yeah. And so I wouldn't say it's a commodity, but it's freely available.

Yeah. It's even in blog posts. It's on podcasts. There's courses, et cetera. But the human side, the emotional. emotional side, that seems to be the big need, the acute need from founders. They can ask other founders, how do I monetize my product? How do I get new customers? All that stuff's out there. What is the secret to being a great coach? And what do most of your clients need? What are the common themes, in other words? Yeah. So the biggest thing that I see, and by the way, you mentioned that it's CEO. So I coach both CEOs, but also heads of investment firms. Oh, wow. Yeah.

So benchmark and Sequoia and General Catalyst and Felices and Greenos. Well, those are the top firms. Why do they need coaches? Aren't they have the big winners? Benchmark and Sequoia? How do they need coaching? Because they all want to get better. Ah.

And they see. So even if you're at the top of your game, those are people who should get coaching or who will elect to get coaching to get even better. Well, they see how effective it is for their CEOs. So they've just gotten wise and said, well, I want some of that too. And they're taking it. And the big difference is that companies, CEOs know that they're running a company. Heads of investment firms grew up as investors and think of themselves as investors.

Their first instinct is not I'm running an organization. It's that I'm going out to find deals and make investments. Right. So there's actually, and there really aren't any books or blog posts written for how to run an investment firm. Plenty of books on how to run a company. So the first, there's much more low-hanging fruit in the investment firms. Just causing them to realize first that they are running an organization, whether they want to, whether they want to do that or not. On the CEO side and in any organization on both sides, what I find is that there is fear is sort of, there is fear in the organization that the head of the organization may not see or realize.

And that fear is causing team members not to give the head feedback on how that person can perform better or what the real problems in the company are. And then even more insidious, peers are not giving each other feedback. Like say, hey, JC, you know, you introduced me as a blank and I really wish you would have done it as the other. Right. And if I never tell you that, then you're going to keep repeating that same action because I never gave you any feedback. But the problem is is that if you're my boss or if you're my peer and I don't have any, if I say this to you, you might react negatively. You might get triggered because I might just say it and I don't know how you react to feedback. Right.

And if you react negatively, now you hate me. And so that's like a minus 100. Right. And I have to live with you now in my career. And I've got a peer who hates me or even worse, a boss who hates me. Right. That could destroy my career. Whereas if you do take it well, okay, then you no longer introduce me.

that way and maybe it's a positive one. So it's an asymmetric bet in the wrong direction. So people just don't do it. They just don't say what they think or give feedback in any way or point out the negative. So these organizations are running blind. And that's the first thing that I do when I go into an org is to help the head of the org realize that if they're not getting feedback from their, if they're not hearing bad things, it means that their people are withholding.

It doesn't mean that their company is perfect or they're perfect. because that doesn't exist. It just means their people are afraid to say anything. And some managers like it that way, don't they? Oh, sure. Those are not good managers. Can they be successful? If they learn to appreciate and want the feedback, yes.

Got it. If they don't learn to do that, no. They can't be. So you can't just be a dictator and power your way to success. I've never seen it. Yeah. Short term, perhaps? Yes.

But not long term. Yes. Long term, you need to be open to feedback. Absolutely. People are scared to give feedback if I'm understanding you correctly. So you have to give them explicit permission? Yes. You've got to literally pull it out of them.

And if you do, on first try, my experience is they will still not give it to you. Absolutely. So how does one get the truth? Do they use a mediator like yourself to go collect the information or these 360 reviews or type forms or forms that get filled? that, how do you actually get people to get real? Yeah. So you can use those steps. I don't like those steps.

I prefer baby steps that's direct. Okay. So I prefer getting people in a room. And first of all, I will have people tell me what they think really. And then I'll say, okay, but I'll ask, let's say we have an exec team. I'll talk to all eight of the exec team members. You all tell me what the issues are. They open up to me because I'm going to anonymize this.

I then say, okay, now I'm going to show you how this works. Let's test. Let's see if the CEO can handle this, how they were. react to the feedback. And then I give them the feedback, but this is all live in a room. And either the CEO gets angry or the CEO goes, wow, I really appreciate that. Thank you. And I accept that. And now I'm going to take the following action. And once the team can see that the CEO took the feedback well, then I say, okay, now you try. And I point to someone in the room and they start giving direct feedback. And the CEO takes that well too. Now we start to have a loop that continues,

that has momentum, and people then start to get into it and they see just how far they can go. But of course, once someone is good at accepting feedback, the more feedback you give them, the more they like it. What feedback is worth getting and what feedback is like, let's you say, complaining, vicarious. Yeah, like complaining, whining, not productive. I, you know, we should have another type of milk in the refrigerator, seven type of milk. Because I know that in my career, I've always been, you know, a very, let's say, brusk leader. Like, let's be serious and do the work. And I really don't like discussing nonsense.

I like to discuss, like, the part of the issue. I can take feedback, but I want to focus on what matters. Right. How you should. It's from becoming like the complain fest, the whining fest, because that is a risk, isn't it? Of course. Absolutely. It's a great question.

So it can't be that if I give you feedback, you must accept it. That would create tyranny of the feedback giver. Tyranny of the feedback giver. I love it. And that is not allowed. Right. So first, I'm going to appreciate you giving me feedback at all. I'm just going to thank you for it.

Yeah. Thanks for that. Then I'm going to repeat it back just to make sure I understood it. And that's actually probably the most important part, is acknowledging it. Exactly. So that you know I actually heard you. And then third, I'll declare whether or not I actually accept it. And I may not.

This is the only part of the process that's optional. But if I do accept it, then I'll tell you what action I'll take to satisfy it. But there's no requirement to accept it. If you tell me, here's a real example. In this past two years, I gained probably 60 pounds just because. I decided I want to, I care about today. I don't give a shit about, you know, some mythical future. And so I'm just going to enjoy myself right now.

And I'll, I become very close with the people I coach. And they want me to be around forever. Right. And they felt fear. And they thought, oh, my God, Matt might die early. Right. And so I got, for many people, I got the feedback. Matt, I really wish you would eat healthier and live healthier.

And I said, I appreciate it. I think you told me that you want me to eat healthier and live healthier. said, yes, this exactly right. Great. I acknowledge it. Third, I do not accept it. And the reason I don't accept it is because this is actually a conscious choice on my part. And again, I don't believe in this mythical future. I believe in today. So I'm not going to act on it. And they went, okay, we gave the feedback. You heard us and we were fine that you don't accept it. And they now have a choice of accepting that you heard them, so at least they feel heard. Now you've relieved the burden of them not saying something.

That's right. That's right. But they don't get to control your destiny. Exactly. When we get back from this quick break, I want to talk about fear. Because it seems to me that one of the jobs of leadership is balancing what I would call healthy fear and paralyzing fear. Yes. And when we get back, I just want to dive into when fear increases.

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And Alex McCaw told us about him, episode 996. He is the founder of Clearbit. And as you know, we had Jerry Colon on episodes 944 and 945. He was also on five years before that. You know, Jerry? I don't. I know of him, of course. You know of him, of course.

Yeah. Let's talk about fear. Yep, great. And when, how should a leader or an investor think about the value of fear, healthy fear, motivating fear,

versus paralyzing fear. Yeah. Yeah, great question. Because these are two different things, aren't they? Yeah, totally. Absolutely. So I want to go down two different alleyways on this.

We'll start with one. I think it's not just investors and CEOs and founders. It's all humans. Humans. We are fearful. Absolutely. But that's kept us alive.

Yeah. And so we- It's a feature, not a bug. Exactly. And so, you know, Sapolsky wrote this book called Behave, which goes deep into the physiology of the brain and where emotions come from and thought patterns and creativity and fear, et cetera. And so I'm not going to try to recreate that. If, you know, if anyone listening has interest, they should read that book or watch the videos that he has, which are phenomenal. And, but he basically describes the brain as the prefrontal cortex, the hypochalmus and the hypothalamus. and the amygdala.

So just make it real basic. Our creative thought occurs primarily in our prefrontal cortex, and fear and anger and thoughts associated with it occur in our amygdala. And amygdala is basically called our reptile brain. It's where when we go into fear and anger, basically the only thoughts we have are fight or flight. Am I going to destroy this threat by killing it, or am I going to run away from this threat and avoid it?

And those are obviously very limiting thoughts. Yeah. And so we don't, the challenge is to notice when those are the kinds of thoughts we're having and recognize, oh, I'm in my amygdala. That's really, it's a primitive brain. These are not my best thoughts. And basically not to act on those thoughts because they're so limiting. Once fear and anger pass, my thought processes go back into my prefrontal cortex.

And now I see all kinds of possibilities and solutions. Those are the thoughts I want to act on. Now, of course, it's very difficult to know when I'm in the amygdala state. You can do lots of meditation and sort of do a lot of practice on how to recognize when I'm feeling fear and anger. Or my preferred solution is just literally empower the people around me. Say, hey, if you ever notice me in fear or anger, just let me know. Just say fear, anger. And I'll know exactly what you're talking about.

And then I'll just stop. I won't act until it passes. So that's one thing to think. The second thing is that fear itself is a healthy response to an unknown situation where there is risk involved. So that it's simply cautioning us to operate with care. The problem is our amygdala is so powerful that it is trying to prevent us from do anything at all. because if we do nothing, we won't die. If we don't eat that poisonous berry,

if we don't go into that dark cave, the, you know, the saber-toothed tiger won't eat us. This is all from millions of years ago. This is programmed into our bodies, into our brainstem, into our spinal cord. I mean, this is the core operating system, is paralyze yourself to survive. That's exactly right.

And a million years ago, 100,000 years ago, that was a very good idea and a very wide, move. Today, it just has tremendous opportunity cost. Especially in business. I mean, freezing is the worst thing you can do. You have to take action. That's exactly right. That's exactly right. So what our brain does is our brain tries to reinforce, tries to get us, trick us to not do anything. So it creates thoughts that are very powerful and seem very real, which say if you do this, it predicts consequences that are dire.

Like in the example I gave before, if I give you feedback, hey, Jason, you introduced me that way I didn't like it. I'm predicting that you're going to get pissed off and hate me and then spend the rest of your life trying to destroy me. Obviously, that's an insane thought, but that's the thought that occurs to people when they're actually in a crisis or fear situation. It might have been a rational thought if you knew me when I was 30. Fair enough. Because I did, I did have an approach of destroying people. Well, that was a slightly different thing. But it is interesting. The, the ability to pause when in fear or when in a fearful or let's just call it an intense situation that is something that you can curate you can you can work on absolutely and i you know having

worked on an ambulance you pull up and the immediate sense of dread when i was working on the ambulance in brooklyn led me to the people i worked with would go into like this incredible Jedi samurai mode where we were just all business. We would walk in, we'd open, we'd knock on the door, we'd go inside, there'd be somebody laying on the ground. And there wasn't the ability to be scared. You had to take action because if this was an asthma attack or a heart attack, we were talking about a minute or two. I always felt like that prepared me for entrepreneurship. Are there ways for people to become good at, let's say, embracing the feet? you're embracing the moment and knowing if this is an intense, fearful moment, it's an opportunity

to deploy skills and to grow and to win. Because whenever I'm in that scary situation, like companies are running out of money, I look at it and say, this is when I do my best work. This is when I can be of service as an investor or when I'm a founder. Every time I've been backed into a corner, I'm like, okay, this is what I'm built for. I tell myself that in my mind. That's my mantra. I'm built for this situation.

Yeah. And I've deluded myself into thinking that. No, it's not a delusion. I think that's right. Yeah. And so you've had the benefit of having lots and lots of iterations on fear still need to move forward anyway. Yeah. Can't turn around and run away.

No. Forced into the situation. Yeah. And then see the result. Right. And then realize, oh, it was fine. Yeah. Then it happens again.

Next call. Fear, go to the apartment in Brooklyn. Oh, my God. Forced into the situation. Oh, it's fine. Yeah. So you're very fortunate. That's a very rare situation that people are forced to go through that loop.

But that is the answer for getting out of the fear-based loop, is to have someone or something force you to say, okay, you predict that if you do that, this dire thing will happen. Okay, do that thing anyway. And then when you do that thing anyway, nothing terrible happens. You go, oh, shoot, my fear gave me bad advice. Yeah. And that's what breaks the cycle. So what I do when I'm coaching folks is whenever I see them in that situation, I make a bet with them.

And I try to take, we try to pick a situation that's not, doesn't have such dire consequences. Right. But something that's sort of low level we start with. And they think if they do X, then A will happen, which is terrible. And I say, okay, I think B will happen, which is the exact opposite and which is great. And so we'll make a bet. And but I say, but if I win, then you've got to listen to me from now on whenever I say you're in fear. Yeah.

And I've made this bet. I don't know, 50, 60 times, I've won every time. Yeah. But it's not hard. Yeah. And so if you ever do think you're in fear, another thing to do is just go talk to somebody else who's not emotionally wrapped up in the situation and trust whatever their brain says. Right.

Because they're not vested in it. That's right. Right. So if you said, if you called another EMT and said, I'm going into a room there's a cardiac arrest, they'd say, okay, step one, check the airway, step two, check the breeze. thing, step three, check the circulation, and then act from there, you know the protocol. That's right. You'd be like, okay, great.

And now I'm diffused. Even just saying it out loud, I'm diffused. It's defuse the fear for me in that situation. And the first couple of times, I will say, oh, it's scary as hell to do CPR on a dead person. Yeah. Like a person you know is not coming back and you do CPR on them for 20 or 30 minutes. It is terrifying. Until you realize, like, I did the best I could, right?

That's right. And there's something about, I think, and I don't know if it correlates with your experience, but the act of going through the fear that kind of makes you as an individual, right? I always feel like my big advantage when working as an investor with founders is I made it through 2001. I watched the Twin Towers Fall. I made it through 2008. I made it through the dot-com bust of 2000. I made it through the crash of 1987.

I've been through so many of these unbelievably brutal moments in business and life and tragedies that running out of money in a company and not missing payroll or having to lay off the staff, it doesn't actually move my pulse all that much. Life goes on. It always goes on. And, you know, when you gave that example of you think A is going to have a piece is going to happen, the first thing that came to my mind, and I'm curious what examples you used in those 60 times was when a founder has to fire, their co-founder or somebody.

they always think it's going to be the worst experience of their life. And almost universally, they go in and say, listen, it's not working out. And the person says, I was thinking about leaving anyway. And I agree. And they're like, oh, wait, this is a relief for you too? That's right. You were going to leave? Oh, my God, let's work this out.

Yeah, good luck in your next company. Yep, that's it. It's almost universally that. Absolutely. What other situations have you had that happen? It's almost always with, that's the big one where people, people are too scared to move. So we have to go to a lower level one, which is there's ex-employee in the company who's much lower down. And I'm also having, you know, strife and

conflict with that person. Let's start with that person. Yeah. And then again, the results for that person as well are, yeah, I'm not happy here either. Right. And I'm glad you noticed. Thanks for pointing it out. Great. Let me find a place. Let me help you find a place that is better for you. Right. And it always works out well. when we get back from this quick break, I want to get into imposter syndrome. This seems to be something that all founders go through. And I even see it after they win the prize. They get the brass ring.

They sell their company. They get the money. You did this. And they still feel like they got lucky. They can't manifest it again. I want to know how often people that you coach have imposter syndrome. and what's the methodology for letting them sort of release that tension when we get back on the business sort of.

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thanks for supporting independent media like this weekend startups. It means a lot to us and the listeners. And thanks for the Hyundai. I mean, everybody could use the Hyundai and everybody needs a little marketing some more customers. All right, let's get back to this amazing episode. All right, my guest is Matt Moschari, Mochari, M-O-C-H-A-R-Y. is the author of The Great CEO Within. How many people you coach concurrently?

A dozen, two dozen? No, right now about 20 CEOs, I'm about five investors. Okay, so 25. 25, which is a lot. That does seem like a lot. You meet them weekly, monthly, biweekly? That's a good question. It's staged.

Okay. So I try to meet them four times quickly up in the beginning. And the reason is because when I coach someone... In a month. Oh, no, four times in a short period of time. I try to do it ideally once a week. Got it. And the reason is is because when I coach someone, I tell them that there are a lot of people that report to you.

You don't report to anybody. Yeah, you report to your board or if you're the head of investment firm. You report to your LPs, but not really. They're not holding you accountable. No. They're checking in. Exactly. But your people that report to you perform better because of the fact that they report to you.

So now you report to me. Got it. And if after four times meeting you feel more empowered, more successful, more engaged, more just everything positive, then you know that my system works and then you can just literally copy it. It's all written out and you can paste it and use it with your direct reports. So instantly there's a system that they can use if they like it. And then we do things beyond that. But that's sort of like the core. That's like 80% of the value is right there in the first four meetings. My intention is not to be a dependent or create a dependency. I like just to help people. And then that's it. And after that we're friends. Interesting. And then what is the ongoing maintenance? like texting, calling, walk and talks, have a lunch. What works best? So for me, I forget everything within six seconds of saying it. So I have to write things down.

So for me, there's always a dock that we share. And therefore, unfortunately, it's not a walk around. It's sitting down either on a video call or in person. Video call actually usually works a little bit better because it focuses more on the dock itself. Whereas in person... So you open up a dock, what is this a master plan of... How to succeed and how to manage yourself? It's sort of, yeah, it's got three sections.

So at first is, you know, where are you trying to get to and what steps you're going to take to get there? And then from our last session, did you actually do those steps? Huh. So that's what I call accountability. Second piece is now what problems have you run into? Okay. And so let's unpack those issues and let's come up with an action plan. Got it.

And then the third part is, how can I be better? We talked about feedback. I do feedback in every single meeting I have, whether it's one-on-one group. It doesn't matter, whether it's one person or a thousand people. And so I model the feedback, both giving and receiving. So we just give each other feedback at the end. Let's talk about imposter syndrome. And then after the other break, let's do it together.

Let's have you mentor me and do the three doc. We'd love to. After the next break. But imposter syndrome, is that a real thing? Does everybody feel it? Are some people delusional and immune from it? How often does it come up? And how do you manage it with?

your clients. Yeah. Almost everyone experiences it. I've known maybe a small handful of people that don't and they scare me. I think they're sociopathic or like they lack self-awareness or something, delusional. Yeah, a little bit. Yeah. I kind of get that from some people.

And now there's two ways. There's those that, I guess what I mean, the few that I've known that haven't had it from birth. Whereas those who sort of get to that place through sort of consciousness training, those are fine. But it's the ones who grew up without that imposter syndrome that's scary. But imposter syndrome is simply that it comes from our childhood. It comes from oftentimes the firstborn has it more than others because the firstborn oddly, almost everything gets created in our childhood and it's from traumas. But those traumas aren't necessarily negative.

So typically imposter syndrome comes from I'm the firstborn. My parents got really excited when I walked. So they cheered. They got really excited when I talked. So they cheered. They got really excited when I had my first bite of food. So they cheered. So I learned to really enjoy those cheering moments.

Yeah. So now I seek achievement and I constantly feel that I'm less than unless I'm in the moment of experiencing an achievement and a reward, et cetera, that dopamine. But the vast majority of the time, I'm not experiencing some public reward and therefore I'm feeling less than. And this is a voice in our head. And frankly, it's very effective in moving us forward. It causes us to work hard. It causes us to learn. This is a little bit related to the healthy part of fear, the motivating part of fear.

The problem is that it eats us alive inside and it allows and it makes it that we can't actually enjoy the life that we're building neither in the present nor in the future. And so unfortunately, I just don't think that it's, it may be good temporarily for the company you're building. It's not good for the individual. And I find that replacing that first recognizing there, the, excuse me, that there is this voice, that's the first step in going, you'll never get rid of the voice. But at least if you recognize it and where it came from, when you hear it, you can go, oh, I hear your voice.

Thank you very much. I don't need you anymore. I'm going to move on. That's sort of step one in the healing process. And then the step two is starting to replace all the actions I do that I don't enjoy, but I think I have to do them with things that truly energize me. Because as a CEO or a head of investment firm, there's 20 things that need to get done by my sort of my role. But it doesn't mean that I have to do them. This is so accurate.

It just means that I have to make sure that it gets done by somebody. Right. And if I don't love doing it, I'm sure. sure almost positive there's someone within the organization who does love doing it and frankly if i don't love doing it i'm not going to be great at it yeah and the person who does love doing it will actually be great at it so it's taking sort of an audit of what i love and what i don't love and then mapping what i don't love to someone who does interesting that you bring this up because i did this a couple of years ago because i you know you start to make a little bit of money and you're you know i was

very driven by not i had a fear an irrational fear of not having money because we ran out of out of money when I was a kid. And it was very traumatizing for me as a young person to just constantly be running out of money and not knowing if we could go back to school or college we paid for groceries. We lose the house, all that kind of stuff. And then once you start, you know, the dog catches the car. You're like, oh, okay. Now what? And I looked at all the things involved as an investor. And I was like, I really don't like talking to lawyers. Nothing personal. I love my lawyers, Wilson Sincini, Fenwick. I love you all.

But going through the documents and going through these details and signing the documents. And then I deputize somebody in our organization, Ashley, and she's incredible at it. She's one of the most amazingly organized people I know. And I just said, I trust you. Here's just the standard documents we want to do. And I also don't like negotiating with people over things that make no difference in the ultimate outcome. You know about these like negotiations that mean nothing. It's incredibly frustrating to negotiate over something that's meaningless.

So I said, I don't want to ever negotiate with anybody again. Will you just talk to everybody and just tell them this is the standard deal? And then if they want to change it, you'll go to Jason, but it's probably better that we just resolve it ourselves. And I haven't had to read documents or negotiate anything except maybe once a month something comes up and people are out of roadblock. And I'm just like, Ashley, what do you think? She tells me what she thinks. And I say, let's go with that because it's a coin toss anyway. Exactly right.

And that is so freeing when you examine the things you don't like and remove them from your life. And then you find somebody who does love doing them. Oh, my Lord, what an unlock. And that's part of being a coach, right? Is letting people know what their superpower is and what actually is dragging them down. Yes. Well, as a coach, I can't tell them what their superpower is, but forcing them to go through the questionnaire. Inventory it.

Exactly. Yeah, you've got an inventory. All right. Is there a generational difference in coaching a millennial versus a Gen Xer versus a boomer? You must have had time with each of them. It seems to me, having worked with folks, the millennial generation, the Gen X, I mean, you're in a self-selecting group of CEOs and investors, so that does change things. But I do very acutely see a different motivation between the Gen X and millennials.

when the Gen Xers want success and the millennials want purpose. And is that an evolution that's happened in our society here in America that is noble and important? Or are we losing our edge because we're not as rabid capitalists as we once were? And can you remind me again about the age groups we're talking about? So Gen X would be born before 1995, like 85 or before. Probably our age, like 40s, 50s, boomers would be over 60, and millennials would be under 35 right now. Great. Yeah.

Well, the reality is most of the people I coach are millennials then. Yeah. And so I may not have as much for a perspective. I don't coach any boomers. Right. But some Gen Xers, some 35 to 50-year-olds. Absolutely. Yeah.

And there is this among the millennials. So, again, rather than notice the differences, I'll talk about the purpose driven of the millennials. Yeah. And yes, that's absolutely, absolutely is there. I don't think it necessarily matters whether it's success driven or purpose driven. Whatever the pull is, the carrot, it gets people to engage in an activity until there's enough momentum that they're actually passionate about it. I think that's all that really matters.

Frankly, purposes, I think we dilute ourselves that we're making the world a better place. The world just is. and whether there's a better iPhone or not does not make the world a better place. And even those who are, you know, I actually, I help ex-convicts get and keep a legitimate job because I think that the mass incarceration in this country is an economic issue and nothing else. But even I don't delude myself that I'm making the world a better place. You're making those individuals world a better place. Yes.

Fair enough. For them. For them. But that's not even why I do it. I do it because I enjoy it. It gives me energy. Why? What is it about you that got you there? Is there something in your childhood? No, actually, the act to opposite. I grew up in a wealthy neighborhood and I grew up thinking that, by the way, this is in my foundation, the Mashari Foundation. I thought that I grew up thinking that all convicts are guilty and that they're sociopaths because anybody can get a job at McDonald's. So you had a stigma. Sure. And I think that's a very common view. Sure. And it was just coincidence that after I sold my first company, I needed something to do.

And so I decided I was going to go make a movie just because that seemed like it was challenging and fun. Yeah. And so I decided I took a little film course and I decided, well, I'll go make a documentary in Brazil because I want to learn about Brazil. Right. And who wouldn't? And so I went down there. And the big thing there is that, you know, in Rio, the slum, the worst. Slums are literally right on top of the wealthiest neighborhoods right on the beach.

And so I made a movie about these slums. And I spent a lot of time in about a year in the slums. And I realized, oh, my God, there are no schools here. And so kids don't have any skills. They can't get a job. So they still have to eat. So the only thing they can do is join their drug gang so they can make might eat. Well, thank God, I live in a country where there's public schools everywhere.

So that's not the case in my country. So I came back to New York, made a second film. This one on amateur boxing, which it turns out heavyweight, boxing turns out the best amateur heavyweight boxers all live in the south bronx they basically congregate there so they can train against each other and so i spent and that's also one of the poorest neighborhoods in new york i end up spending a bunch of time there and realizing oh my god there's schools here but they're so bad they might as well not exist and again if i'd been born in this neighborhood i would join the drug gang as well right and then i thought oh my god is it possible

that everything i've thought is completely untrue that guys who commit crimes are actually just acting rationally. They're just trying to survive. So if that were true, then I know this is going way off course from approaching. No, no. This is incredible. Right on. This is what the show is about is tangents. Okay. The best stuff happens in the tangents. As you know. Right. That's true. And so I said, well, is it possible that if I took the hardest core criminal and taught him how to get and keep a legitimate job, would he? And I thought about for a little while, I thought, well, wait a thing. That doesn't sound like a fun thing to do. And what if I'm wrong? Yeah. And what if I'm then dealing with a, you know, a known killer in my presence? Who you've invited into your life and you've tried to

basically do an intervention with. Exactly. Yeah, now you're in it. Exactly. But I also had the thought that who else at 30 years old is independently wealthy, has lived in two of the worst slums in the world and is available. Right. There's nobody else. So if I don't do it, who will? Yeah. So I did. I went to, I went to Rikers Island and I talked to the warden there and said, listen, I want one of your hardcore guys that's getting out. And he laughed and said, they're all hardcore. And so you end up introducing me to one. And turns out I went through this experiment. I taught the guy how to, he looked like a thug, act like a thug, talked like a thug. And I taught him how to dress like me, talk like me, act like me. And instantly got a job. But two weeks later, he lost it. Because

they did the background check, had a criminal background, said, we can't keep you. And that went through several cycles and after about six jobs like this, we realize, oh, wait a second, we've got to get you a job where they don't care that you have a criminal record. And it turns out there's very few of those. It's only skill-based jobs where there's a massive shortage of the skill itself. So if you show up with the skill, there's no other applicant. I don't care whether you've murdered somebody, you get the job. Plummer. Exactly. It's the construction trades and it's truck driving, having a commercial truck driving license. It turns out that truck driving is easier to teach the construction trades is is an apprentice trade, which I wasn't able to do, but I could pay

for a guy to go to trucking school. So that's what I ended up, I ended up doing. And now I, it cost me about $4,000 to train a guy to become a truck driver. And once he takes about 60 days, and once he's got that, he then is making starting salary, 50 grand. And within three years, he's usually making $100,000. And after that, all the problems disappear. And so I do this together with Jason Green from Emergence Capital and Andy Bromberg. We've created something called Join Free World run by a guy named Jason Wang. This year we trained about 80 guys. 2019, 2020, we'll probably train about 300 guys.

And so far, we've only had one guy go back to prison. And that was very temporary. You already got out again. Amazing. Yeah. So it works. And for you... I have no idea how we got in that subject, but I'm glad.

No, I mean, talking about purpose, I think, is what got us there. and you know you talked a little bit about whatever the motivation is you in order to succeed in the pursuits that you're coaching a requirement is the resiliency um and the motivation that that's sort of combination of the resiliency to not give up when things get hard and the motivation to do your best work in a in a very dynamic hard you know area i mean and if you are not truly motivated, like being an athlete or a musician, like you have to want it. Yes. Yes. You can't make somebody want it, can you?

No. Except that you can take, well, people want it, but again, do they want the, they want to avoid the absence of it or do they want the thing itself? I think most people that I encounter anyway, their motivation is fear. Their motivation is fear of failure, fear of not, fear of not having the money. Like you described, fear of not being viewed as successful, fear of not being liked. So it's a negative motivation, which is very powerful. What I try to do, though, is change that into a joy-based motivation, which is, I think,

equally powerful, but much more enjoyable along the way. And the short-term fear is a very base level. Like competition, fear, these things are base. They will motivate you without having to think too much. But to get to purpose, to get to joy requires some effort, does it not? It requires some enlightenment. Absolutely. And it takes time too.

Yes. Yeah. Well, there's two ways, I think, to get to joy. One is the direct approach saying, well, what makes you happy and try to go do that? Unfortunately, I've never found success going down that route. because most people I don't think we don't really know what makes us happy. Why not? I don't know.

Yeah. But the other route I've gone down has turned out to be very successful. And that is what we talked about before. Let's identify the things that you don't like. And let's simply remove them. Exactly. And then you have a whole bunch of empty space. And then you're going to end up filling it with stuff.

And then let's do the clean out again. Until finally, all we've got is stuff that you live. like that you're doing. And when that happens, boom, this light goes off. This magic appears. And all of a sudden, I feel like, yeah. This is why I'm here. This is what I'm good at. Exactly. This is what I enjoy. That process of elimination. Knowing what you love is about knowing what you don't love. That's right. What you don't want to do. That's right. When we get back from this final break, you're going to coach me. You take me to that first session? Absolutely. Oh my God. Here we go, folks. Get your chairbox. I might start crying about my childhood when we get back on this week in Snarnoz.

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Matt Moschari is here. Yeah, he coaches investors like me and CEOs, like the ones I invest in. You do the mid-level managers at all, like the VPs, the managers, or is that a different type of coach? I have coached executive teams, like I clear a bit with Alex. I basically went in for two months and said, okay, Alex, I'm now going to act as CEO. And I'm going to run the company. You're going to sit next to me during every meeting.

And I'll show you what it looks like. That's that shadow CEO method. Exactly. Unpacked now. What is it? Well, it's literally that. It's one day a week. It's one-on-one with every VP and then the exec team meeting and then in all hands and then an open office hours. I mean, it's a 12-hour day. It's brutal. And, you know, the CEO just sits next to me the whole time to see what it is that I do. And it usually takes about four weeks to sort of implement what I call the system. Another four weeks for good results to start happening and another four weeks for the company to really just take off. So about 12 weeks total. And then at that point, the CEO is like, this is amazing. but the CEO may also say, it's amazing, but I don't want to run that because it's just like a bunch of, it's like a checklist, just process, process, process, process. And oftentimes the CEO is a big thinker and a product person and not a process person, in which case we just slot someone else in.

The problem is, it's very effective. The problem is it takes a ton of my time. So I actually don't do that anymore. And, you know, oh well. Oh, well. Yeah, that's like to really roll up your sleeves. Yes. What does it cost to have a coach? Like $25 grand a year, $50,000 a month?

I have no idea. A couple thousand a month. Wait a second. You coach 25 people for free? Yeah. That's not logical. You should get paid. Did they give you equity or something?

Sam Allman had a great line. He said, we all should be doing things that we would do for free. And I just took that line one step further and said, well, why not actually do it for free? Wow. And for me, it's actually very selfish because it forces me to put on that filter of, do I love this? And I mean love it. So if I'm not loving it, it stops right then, right there. Like even in this situation, if I weren't loving this, I just get up and walk out. Wow. But I'm loving this. I'm loving it too. All right. Here we go. We're in our first session. We got the document open. We're video chatting. You got referred to me by Alex. from Clearbit. He said, J-Cal is this incredible investor, but he wants to be even better. Yeah. What happens now? Take me through it. Let's do it as if there's nobody else listening. Perfect. So Jason, there's three parts to this, but it gets increasingly interesting. The second part is

more interesting in the first and the third part is more interesting in the second. So I'm actually with you, I'm going to go in reverse order. Okay. Because I don't know how much time we actually have. About 15 minutes. Yeah, we won't get through all three if we go chronologically. So we're going to go reverse order. Okay, here we go. So the first thing is feedback. This is the absolute most important thing. All right. Get ready, Charles and Nick in the control room. Well, for now, it's going to be me. Okay, great. And so we've already had a little bit of interaction here. Yeah. There's already be something at some point that you kind of went, uh, I didn't love that about Matt. I didn't love that Matt did that. I don't know what it is. I don't want to tell me. I just want you to think it.

Okay. You have that thought? Yeah. And also, by the way, something that if you told me, you think that it might actually upset me and that I would then not like you. So like what's the edgiest thing? Okay. Okay, perfect. I got it. You got it? Yeah.

Now can you please tell it to me? I think you not taking to heart what people told you about your weight was a bit callous and that you might want to think about the impact you're having on them worrying about you and that it would cost you nothing to, you know, just fast and maybe eat 500 or less calories and drop 10 pounds. And I'm really speaking to myself in this regard because I just lost 15 and I'm trying to lose the last 10. So we're a sympathetic on this. But when you said that, it triggered me as well because I feel like I need to lose the weight because I have people tell me the same thing and I've been trying. Perfect.

So first of all, thank you for being willing to say that. Right. Second, I think what I heard you say is that when I got the feedback from all my cochees that I should lose, way. I just said, nah, that was callous, and I should really think about the impact on them and on others. And it would be so easy for me to act on it that in the, in the grand scheme of things, why not? Why not? Because they care about you and they want you around. And for you to say, like, I don't care what you think. I want to eat my brisket and I want to have a double serving. That's my priority. I don't believe in living forever. They do want you to live forever.

Yeah, and my family as well. Oh, and your family too. So I don't know if that was an actual situation or a hypothetical. No, that's a very real situation. Right. So I'm with your, your, the people who gave you that feedback. Perfect. I'm on their team. And I, did I, do you think I understood what you said?

You understood it. You reflected it back perfectly because you actually used the same words. Awesome. So I've appreciated, I've acknowledged it. Now, let's see if I accept it. Right. So I don't want to seem like a flip-flopper. Right.

But now I accept it. Here's why. About 30 days ago, I decided maybe 40 days. days ago, I decided on my own, just for fun, I would stop eating carbs and sugars and alcohol for a three-day period. And after that, I'd play in a weekly Sunday soccer game. And on that third day, I went and played the soccer game. And I scored three goals.

I never score goals in this game. And it was a lot of fun. Wow. And I thought, wow, I really enjoyed that feeling. Yeah. So I decided to keep going with it. And so, like you, I've lost 13 pounds in the last 30 days. And I'm great.

But I'm enjoying it now. So I do accept it and I'm going to keep going in this direction. Again, I'm accepting it because it's now resonating with me. Two, three months ago, it didn't resonate with it. Was it not resonating with you because you felt a little bit of critique and it was too personal, do you think? No, no, not at all. It was literally, it was a conscious choice. I want to be doing this.

Right. Now I want to be doing something else. I love it. So I will act on it. And if you even want to, I will report back to you in a month. to make you so you can see that I actually acted on it. Fantastic. Now I feel great.

Not that I need you to report back to me, but I just feel good for your friends who care about you and who must have been a little frustrated by you dismissing them. Awesome. Thank you. All right. So that's the first part. Got it. That was good. That felt good.

Right on. So that's half. It felt productive and it felt like so personal because weight is such a personal issue. Right. That it felt particularly cathartic. Awesome. To use a word. Awesome.

Yeah. And that, so we did half of the feedback. The other half would be me giving you feedback. Go ahead. And by the way, I'd also tell you what I like that you've done and what I wish that you would do differently. Go ahead. Because it's important to validate the things that you're doing well.

Yeah. And also validate the fact that I value this relationship. Because you're not going to take feedback from someone who like just hates you and sees nothing but negative in you. It's not worth trying to. Yeah. No. It's biased anyway.

Exactly. It's loaded. But let's not do the second half. Okay. actually go into what would normally be step two, which is the issues that you're facing. Right. And let's unpack them. Sure.

So, and this is, I mean, this is going to be more vulnerable for you than for me. Let's do it. Okay. So what's a challenge that you're facing in your life? And a way to think about this is what, when you think about anger or fear, what thoughts come to mind in your life? Anger and fear. I have, I try to think about fear. It's very hard for me to put my finger on fear.

I fear some of my investments that I'm very invested in and I want to see succeed failing. It would be heartbreaking for me to have put years of work into them and to watch the founder fail and think maybe I didn't do enough to support that founder. That to me is beyond my own personal failure, which can't happen. happen now because like you on post money and I've already hit you know three or four home runs it's not about me anymore it's about that feeling of gosh I I told the world that I think that this could be the next Uber or Robin Hood it could be the next com and it went to zero yeah to me it's just you know it's like striking out or or just sending people to a restaurant and telling him this is the greatest one ever and it failed right yeah yeah that to me if I have

a fear of anything or anger, I'd be angry at myself that I didn't get it over the finish line. And maybe I could have. Okay. What didn't I do? All right. Or why did I pick that one? All right. And bet everything on it.

So this is almost like you're anticipating the sadness that you're going to feel. And have felt when things failed, because I felt it before too. Okay. Yeah. But is this really keeping you up? Let me ask you a different way. Yeah. I'm happy to unpack this one.

but this is very future. No, no, this is keeping me up right now. There's a... So you didn't sleep well last night, and this was a thought you had when you woke up. Over the last couple of weeks, I have been dealing with a couple of companies that have struggled and could face imminent failure.

Yeah. I wouldn't say it's keeping me up all night, but I wake up and I think about it when I'm having my coffee. Yeah, and I go to bed, I think about it, yeah. It's the first thing and last thing, for sure. Got it. All my mind. Okay.

Yeah. So there are several things we can do here. But before I give my feedback, I'd like you to tell me, what do you propose? If you were giving yourself advice, what advice would you give yourself? Yeah. Ask for help. From what? Let's get specific.

Well, ask my peers, other investors, like, how do I save this company or how do I shut it down gracefully? Or how do I deal with something I made a big bet on not working? out. Yeah. Perfect. Yeah. Okay. And I started doing that.

Okay. I started calling people and saying, hey, I need help on this one because I don't think this one should die. This one should survive. But originally the problem you're telling you was fear of what's going to happen, the feeling you're going to have when you have to let people know that these companies die. So that's preventing some of them, maybe helping some of them. Maybe.

It's really the fear of, I just watching the founder fail. It's even more. Like, I know the investors can lose their money. and I've made so much money for other people that it's no big deal. They can afford to lose it. It's the failure of me being able to get the founder to victory. Perfect.

Because I basically gave them the jet fuel to go on the rocket. Perfect. And now the rocket's coming back down and they didn't make it to orbit. Got it. To use a metaphor. Let me ask one other question. What did you do to help create this situation?

I mean, you basically just said it. I gave them on the rocket. I told them they could do it. I told them, here's the fuel. Hit the button. Let's go. Yeah. Let's try.

Yeah. What else did you do and what do you have to believe for this to be a problem? It sounds like you have to believe that failure is going to be terrible for this founder. Yeah, it's almost, I know the founders will succeed into a second company and I'll invest in them again. Yeah. Which is always my commitment to the founder. Like if we if we do our best, I'll be there for the next company. Yeah. And I'll help you find a job if you want to do something in between. You can be an entrepreneur. or in residence. It's a lot of options like that. But it's more the, I fear the regret that I didn't do enough. Like waking up one day and saying, fuck, what if I did this? You know, like you, you go back to the game and you're like, I should have thrown the hell Mary or I could have run this play. I could have made this phone call. Did I do enough? Almost like if I am the coach, did I coach the player to success enough? You know what I'm saying? Yes. And did I give them the right direction? Did I give them bad advice? You know? That to me falls on me.

This is freaking beautiful. Okay. Because Jason, you're bringing it full circle. Yeah. This is you. Yeah. Experiencing imposter syndrome. Right. And this is you also being gripped by fear. Yeah. Because in the very beginning of this podcast, you introduced it by saying, hey, failure is a part of being a founder. And you know what? You move on. You'll succeed in your next one. Right. You get the right to start again. And you painted a very rosy picture of failure and it sounded very compelling to me and it sounded very true to me because that's the experience I've had and I've seen with others. And yet now in this situation, you're thinking, oh my God, it's this big tragedy and it's really all about me not doing enough and me not being good enough. And whereas that is fear gripping you and taking

you literally from 30 minutes ago when you weren't gripped by fear to now in a place where you are gripped by fear in the same situation describing completely differently. So I would ask you to vision with each of these companies. Let's imagine that it actually does fail. And you're going to have to do this on your own. We're not going to have time to do this now. But I would take a good 30 minutes and go slowly. The next thing, the first thing to do is they run out of cash. And then they have to lay off the employees. And then the founder has to send out an email. And then you have to have the conversation with the founder. The founder really calls you. and then and walk through each step along the way and what you're going to do to go help that founder start again.

Right. And walk it all the way through till the end. And when that founder either comes back or doesn't come back and then come back to me and see how you feel. Right. But my guess is just experiencing the reality. Right. It would be like you walking into those houses in Brooklyn, apartments in Brooklyn and go, I feel fear, but I can't stop. Now I'm in it.

and it's fine. Right. It all works out. It all works fine. Would you be willing to do that? Absolutely. Absolutely. You know, and I've had moments where I told myself, like, hey, listen, you're built for this.

You're the Jedi in this situation. You're the Jedi master. You can just walk into any situation. And you got the lightsaber and, hey, you may lose an arm. But they can put one of those, you know, Luke Skywalker got that metal arm. So I have the metaphor in my mind of how to deal with it. So that's why it's not keeping me up at night. But, you know, the fear of them just me not doing enough makes me want to do more.

And I, you know, I try to channel that fear into just doing a little bit more. So I feel like I gave it my all. Okay. Because to me, that is my always my regret, you know, when I look back on my career. Did I actually give it my all? Did I actually leave it all out on the field? Right? You know what I'm saying?

Yeah. Like even after this interview, there'll be a moment in time when I'll say, I'll be driving home and go, fuck, I had a great question. I didn't ask it. You know? And that always burns me a little bit. And so what then I'll leave you with is there's always two ways we can look at any situation in life and in the world. It's all about the question we ask.

If we ask what's wrong with this situation, what didn't I do well enough? Right. What could I have? How was I inadequate? Right. We will always come up with an answer. And then we will focus on that answer. and then we will drive towards sadness and negative feeling.

But if we simply flip the question, say, what's right about this situation? What's right about the fact that I had this great question that he didn't ask? Right. Oh, now I get to ask it later on. Right. I get a follow-up. Exactly.

Back on the pod. To reach it back out to Matt. Yeah. And there will also always be answers to the question of what's right with this situation. But if we ask that question, then all of a sudden we think about what's right, and all of a sudden we start feeling joy and exuberance and. and bliss. So it really is back to what question do we ask ourselves. So I would encourage you to ask every situation that you encounter that frustrates you, angers you, you feel fear about, ask yourself,

what's right about this situation? What's good about it? And so I ask you right now, what's good about some of your companies are going to fail? What's good about that? Well, there was such a big prize and such a meaningful potential victory that to not have tried would have been worse to have tried. So that to me is always something that I think about because so many people I know talk but don't try. So many people I know meet with the company but don't write the check. And I always take pride in taking my own counsel and backing the companies that to many

people seem like a fool's errand. You know, Com was one of those where they met with 80 investors or something like that. They got 80 knows. And I was maybe the 81st and I said yes and it worked out. So for me, those are the most rewarding is when I make the contrarian bet, when I make the bet that everybody else is afraid to make, I introduced Uber to 22 investors at that Open Angel from the event where Travis pitched and only three of us said yes. And I get to see those other 19 investors and all 19 when I see them say, I should have listened to you. I was an idiot. Oh my God. How did you see it? I couldn't see it. How did you see it? And that risk taking is kind of my skill, I think, is to take the bet to gamble, you know? And it's, it is the good in it is

that if you take that risk, if you consistently take that risk, man, does it pay off, you know, the ones that do succeed are such outliers that the contrarian bets are the ones that make your career, right? My two best now are a cab company and a meditation app. You know, like if I told you as investors, like, you know, in 10 years, my cab company and my meditation app are going to define my career. It's like, are you delusional? Like, it's not enterprise software. It's not a search engine. It's not a social network.

It's not a e-commerce site. No, it's a meditation app. and I can't have company. Right. And that's what's good for you in this situation. What's good for the founder who fails that you backed and gave the jet fuel to and made them feel like he could succeed or she could succeed? Oh my God. Now they have all those battle scars and all that experience.

Next time they're going to just run up the hell and crush it. They can't make those mistakes again. They've been burned in. Perfect. Yeah. There's more good than there's bad. That's for sure. Right on.

And so that's the way to process. That actually makes me feel a lot better. Awesome. All right. Thanks for the free session. This is my way of scamming myself into a free mentoring session. How do you pick? They're all free.

I know. I can't believe that. How do you pick who to coach? Yeah. And how do you, who do you fire? Who do you not take on? I'm just curious. Maybe an example would be good.

Yeah, the longer story is that I was coaching again these young guys out of Stanford. And that's what I thought that I only could coach. And then one day, one of them introduced. me to my first sort of celebrity CEO guy named Naval Ravi Khan, who started Angelist. You were Naval's coach? Yeah. Oh, that's a good friend of mine. Yeah, Naval's a great guy.

Amazing. And he came over to my house, we sat down, we spent about 90 minutes together. And there's this problem that had been sort of plaguing him for a decade. And in that 90 minutes, we not only unpacked it, but we came up with a roadmap and six weeks, he implemented the roadmap, and six weeks later, a problem completely solved. Wow. And life, you know, magically better, amazing. And he turned to me and he said, Matt, I know everybody.

I know all the coaches out there. you're the best in the world. I thought, that's crazy. That's impossible. But I thought, okay, well, if it is true, then I should be able to coach whoever I want. So I made up a list of 20 people, and these are the people that I like to coach. All in San Francisco, all the people that sort of, I admire, respect. And I said, well, do you know anyone on this list?

He said, yeah, I know Brian Armstrong from Coinbase. I said, great, can you please introduce me? He did. I started coaching Brian. After a few months when I created trust and like with Brian, I said, do you know anyone on the list? He said, yeah, I know Sam Altman. So he introduced me to Sam. I love Sam.

Sam and I play cars together sometimes. Right on. And after a few months with Sam, again, trust and light created. I said, Sam, do you know anyone on this list? He said, I know all of them. Yeah. And so he introduced me. Now, I don't coach all 20, but I coach about 10 out of that 20 person list.

You made the list. See, you did what you're doing with me. You said, hey, make the list. Absolutely. And then you executed on the list. That's exactly right. You weren't afraid to ask for help either. That's right.

That's critical. Yeah. Yeah. And that's it. I feel bad about my relationship with Naval because I left Angelist because he he doesn't like to negotiate. Right. Like he just wants to have one deal with everybody.

And I'm like a hardcore negotiator. And we were like real partners and friends and I was the first syndicate on Angelus and then I left and kind of feel like, you know, we never really hung out after that. And I kind of felt bad about it because I kind of like him a lot. But he's a little bit reclusive and like introverted. And I'm like way out there and extroverted. But we used to have these great. conversations where he talked and then I'm like, hey, come on the pod and he's like, I'm not doing

podcast anymore. That's true. And he's not doing podcasts anymore. I know. I think the last one he did was Joe Rogan. Joe Rogan. Yeah, he did Tim Ferriss or Joe Rogan. But that doesn't mean he doesn't like you or want to hang out with you. And even if he doesn't have time, because most time he's in Bali or Toul or, um, but here's my recommendation. Yeah. But you just ping him and just say hello. Yeah. I should do that. I'm thinking. You know what? Your name came up today, Naval. I was thinking about you. And it brought back. It was fun for me to. It was fun for me to. think about you. That's it. Let's see how he responds. All right. I bet you this is, well, what's your prediction? How will you respond?

Good question. I think he would say, I hope you're doing well and your family's great. Because, you know, we've had dinner, our wives and stuff like that and, you know, but, you know, he's a busy guy. I think everybody wants to get, you know, it's one of the things with these busy guys and gals is everybody wants to get something from them. I don't want to get anything from anybody. Like I'm good friends with Tim Ferriss. He and Tim did a podcast with Jerry and he was just like everybody wants something for me I can't take it anymore

there's just too much inbound and I texted him and I was like you know I rattled my brain because we've friends for a long time I hope I've never asked you for anything I don't think I've had other than to invite you on the podcast

which you did which I was grateful for but I'm not one of those people and he was like no you're not can I call you I need help with these three things and then we talked on the phone for three or three hours

over the last two or three months and I kind of rekindle my friendship with Tim talking about a couple of things that we both have in common that we both needed to kind of, what's the word? We had to like sort of game theory, a couple of issues that we both were in Sympotico on. And it was nice to kind of like rekindle it and also realize that I'm not a burden to him. Like I hate to be a thing. I hate to be a burden to important people. Like like you, I have a lot of people who've become very successful in my orbit.

And then you become a super router for people who want to get something. So everybody wants me to introduce them to Elon or more Cuban or Travis or. Tim or whoever or Naval. I don't want to invite any. I don't want to interrupt those people from their work, you know. But you can always do the double opt-in method. I do. I do reach in saying, hey, you know, Tim, here's an email.

Do you want to meet this person if you ask creative? I don't even like to do that. Because I feel like it takes up cognitive energy of like a Tim Ferriss or something like that. But anyway. I get those emails all the time and I don't mind them. As long as it's double opting. Here's what I hate. Oh, yeah.

Hey, Matt. See me on the email with the person who wants the intro. Exactly. Now I've got to go through mental gymnastics of how to say no. And yeah. Yeah. Nice to meet you. Right. All right. Well, I've got 200 investments. But half of them need a coach. Unfortunately, Nileo. This is what happens. So good coaches get filled up. Their dance car gets filled so quick. That's exactly right. But one last thing on the ball thing. So there was a little bit of your prediction is he'd be like, yeah, you know, how you doing? Great. Good to hear from you. Sort of a neutral response. Yeah. That is, I think, I think. your fear talking. Fear of rejection, the sort of the sadness that you have about the relationship you have before. Yeah. And I predict the opposite or I predict much more positive. Oh, okay. I predict that he will go, wow, Jason, great to hear from you. Thanks so much for reaching out. Just wonderful to hear you and think about you. I'm going to give a shot. So that's our bet. Okay. I got the bet. Yeah. I said A, you said B. You're always right on these things. So maybe it's my

fear talking. I'm not. And I of course could gain the system and tell Neval to give you that reaction, but I'm not going to. Don't do that. Let's actually do it. Let's do it as a real AB test. Well, listen, Matt, thanks for coming on the pod. I know you're busy. And there's no reason for you to come on because you're not looking for new customers

and you don't charge. But I just thought, you know, 200,000 people listen to every episode and founders are going through this stuff and giving them at least a little, you know, idea of how to release the pressure and understand that none of this is fatal. You know, we see suicides of entrepreneurs. And that is the craziest thing, isn't it? For a founder to kill themselves over the failure of their business is the biggest tragedy in the world. Absolutely.

It's crazy. We've had two founders who've been on the podcast. I don't know if it's a law of big numbers, but we've had probably 1,400 guests on this podcast and 1,100 episodes. And the founder of EcoMomom and the founder of Cambrian Technologies, both of them committed suicide when their business is failed. And it haunts me to this day, having sat across the table from them and heard their vision, that these two beautiful souls would just, Jody Sherman and founder of Cambrian, Analyptych, Cambridge Analytica, no, not Cambridge Analytica, will come to me in a minute. But to just think that a founder in this despair would kill themselves.

Well, to feel that much pain. That much pain, that much shame, that much, you know, You know, self-hatred. I don't know. I never, that is one thing I can never understand is suicide. Right. And I talked to a friend of mine about it and they said, listen, it's a disease. You can't understand a disease.

You understand cancer? You understand why cancer kills people? Right. Kind of don't. Right. Nobody really does exactly understand it. And it's just, yeah. But you see people get pushed to that point, I'm assuming, like that level of despair.

And also the sort of this. Austin Hines, yes, thank you. The suicide is actually, the thoughts are very common. I ask this often in a group. How many people here have thought. thought at one point about suicide because I do this thing also in groups to to create connection. I ask people to tell a and to get over this fear is to tell a thought that or an action or thought that they've had about which they feel shame.

Ah. And to share it with the group. Yeah, that'll create a bond. And to see how the group reacts. Of course, they're predicting the group will hate them. Right. But of course, that's not what happens. No, then they get massive sympathy.

Exactly. And bonds them forever. One thing that almost always comes up is I've thought about killing myself. Yeah. And so then I asked the right. wrestler group who Harris thought about killing himself. It's always between 30 and 50% of the group has had suicidal thoughts, including me, by the way. But I was 20 and 21 just got out of college and I got fired for my first job and had no idea what to do and was drifting and

felt completely useless. After having graduated from, you know, one of the best universities in the world, I thought, I'm an idiot. I'm broken. And but then life goes on, as you say, and life doesn't It's amazing how people think is important when they're young. They get so caught up in thinking that that job was important and that job was the least important thing that ever happened to you. In all likelihood. That's exactly right. It's just insane.

Tim Ferriss on this podcast just confess because I was like, you know, you seem like such a positive person. He said, yeah, no, that's not correct. And he said, actually, you know, I have depressing thoughts and I get melancholy and I actually thought about killing myself. And he says this in a live episode of, this week in startups. And then he wrote a blog post about it because somebody who was in the audience came up to him and said, I was thinking of killing myself. And then I saw you on the podcast and I talked

to, you know, whoever about it. And it kind of saved my life because at that moment in time, I was having this moment that you had when you're 21 and Tim Ferriss wrote a blog post about it. And now if you Google suicide thoughts or whatever, he's in the first page of Google explaining when he had suicidal thoughts when he was in college. and how he got through them. Yeah. All right, Matt. I'll see you.

We'll do some brisket. We'll do the brisket off. Or maybe you make the brisket. I'll make the beef ribs and we'll just, we'll pound it out. Sounds great. Add five pounds and then we'll fast for three days and go play soccer. Perfect. This has been an amazing episode.

Thank you to Charles and Nick on the ones and the twos. And thank you to Matt for ringing the bell and making sure the money comes in for the advertisers. Thanks to the advertisers and sponsors. And thanks to Alex McCaw of Clearbit, episode, 996 if you missed it for suggesting we have Matt on great job everybody go read the great CEO within you can get it on Amazon and thanks again for coming on the pod thank you Jason this is fun see you all next time bye bye