The Exchanges

Q Can I ask, once you then realize that they're Neanderthal thoughts, and you've recognized kind of your state of consciousness, be it Fear, anger, or both at the same time. How do you then react? Is it then a case of act fast? Is it a case of deliberate slowly? What's the right subsequent path post recognition of feelings?

A If I have to act immediately, I outsource my thinking to someone else. Someone who's not in fear or anger. So I share the situation with someone who's not part of the situation, and their brain, therefore, is not triggered because it doesn't matter to them, and they tell me what they would do. And almost always, it's far better. What I was thinking of doing. That's method one. Method two is if there's no urgency, I simply wait. I simply wait until the fear and anger dissipates. Now there are some mental exercises I do. Byron Katie has a thing called the work, which is a series of questions that lead me to realize that my anger is not necessary, that my fear is not necessary because I have this view of the world, but the opposite of that view has merit as well. And maybe just as true as the perspective I am in at the moment. And so that allows my fear and anger to dissipate as well. Once it does, then I trust my thoughts.

AI assessment note: “If I have to act immediately, I outsource my thinking to someone else.”

Q Can I ask, once you then realize that they're Neanderthal thoughts, and you've recognized kind of your state of consciousness, be it Fear, anger, or both at the same time. How do you then react? Is it then a case of act fast? Is it a case of deliberate slowly? What's the right subsequent path post recognition of feelings?

A If I have to act immediately, I outsource my thinking to someone else. Someone who's not in fear or anger. So I share the situation with someone who's not part of the situation, and their brain, therefore, is not triggered because it doesn't matter to them, and they tell me what they would do. And almost always, it's far better. What I was thinking of doing. That's method one. Method two is if there's no urgency, I simply wait. I simply wait until the fear and anger dissipates. Now there are some mental exercises I do. Byron Katie has a thing called the work, which is a series of questions that lead me to realize that my anger is not necessary, that my fear is not necessary because I have this view of the world, but the opposite of that view has merit as well. And maybe just as true as the perspective I am in at the moment. And so that allows my fear and anger to dissipate as well. Once it does, then I trust my thoughts.

AI assessment note: “If I have to act immediately, I outsource my thinking to someone else.”

Q This is probably why I need coaching. I'm so emotionally detached. Um, so tell me, I spoke to Henry there at Brax. How do you feel about the rise of chief of staffs?

A Oh, I think it's brilliant. It is the answer for extending oneself when no other hack remains. So once you've done inbox zero and you've automated everything you possibly can, but the world is still asking for more from you and you want to respond, unfortunately it requires another human. And the key about a chief of staff, however, is the way that you train them. And the best way to train chief of staff is to give them full access. They have complete access to your email, to your calendar, to every meeting that you're in. So they literally sit beside you, listen in on every call and sit in every meeting. And that lasts for probably one to two months until they fully grok how you think, because they see the information you take in and they see the decision you make. And now they can start to correlate and pattern match. And then they can start to act literally on your behalf as you would. So that's the key though. The key is giving them full access.

AI assessment note: “Oh, I think it's brilliant. It is the answer for extending oneself”

Q for first time founders on the flip side is in terms of obviously for me now sitting on boards and for founders who have to do board management effectively. I'm interested having worked with some of the best CEOs of the last five to 10 years. What would you advise me in terms of being the best board member I can be having had the incredible experience that you have?

A First of all, know that boards are the death of every great investor. So Be wary. If you sell to founders that when they take your money, you will join their board and be on their board forever. Know that you have just ended your career eventually. And the reason is boards take up a tremendous amount of time. And so, you know, there's at least four year, if not more, they're usually half a day to a full day. Often you have to get on a plane to go to them. So there's travel back and forth. And now you're on four, but imagine when you're on 10 and then 15 and then 20, and you've made this commitment to be on them forever. So you can't get off, or at least you think you can't get off. And now, 40 to 50% of your time is spent attending board meetings. And you have to, of course, spend, if you have partners, you have to have 20 to 30% of your time doing internal meetings, you know, investment committee, et cetera. That leaves another 25% of your time to just simply support your portfolio companies or do other sort of random things. And now you have zero time to look for and make new investments. So be very wary. Don't sell a lifetime commitment on a board. Sell, support. That's what's valuable. And what's valuable to CEOs is the support they want, not the support that you want to give. So simply ask them, how can I be most helpful to you? And they will tell you. And usually it's not…

AI assessment note: “Don't sell a lifetime commitment on a board. Sell, support. That's what's valuable.”

Q Not at all, but I, I do want to kick off with a little bit on you. So over the last few years, you've become really the Oracle coach of the leading Valley CEOs. So how did you make your way into the world of startups, Matt? And how did you come to the position you are today?

A Well, I, I made my way into startups three different ways, three different times. The first as an investor, when I was quite young, just had a business school at a growth equity fund. And that was in the late nineties when the internet heyday one point O began and it just went crazy. And then I became a partner, but a very junior partner. And I realized if I want to really participate in this wave of value creation, I have to start my own company. So I did, I left that firm, which was a scary thing to do because that was sort of a guaranteed track to success. And I founded a company with a friend. And again, at the time it was the late nineties was 99. It was just insane. He raised hundred and thirty million dollars, hired 280 employees. It was just crazy. And luckily that worked out financially. We were terrible operators, but at that time it just didn't matter. And so that was a great financial event for me. And then I decided I wanted to do other things, but eventually I came back to Silicon Valley. Once my wife and I started having kids, we decided we could live anywhere in the world. And we decided that Silicon Valley was to us the best place to raise a family. I know that sounds odd, but to us, it was phenomenal. Once we came back here, I wanted to be part of the community again, but I didn't want to start another company because starting a company is a lot of work and th…

AI assessment note: “I made my way into startups three different ways, three different times.”

Q person is? I spoke to many of the people that you've worked with before, and it was actually quite a few of them that said, you ask very provocative questions, and they said you'd get away with it. My question to you is, how do you do that? And are there commonalities to the questions that you ask that are provocative, pressing to really determine the nature of the person?

A Well, I'm going to try to think of what these provocative questions are. I think one that probably feels provocative is when I have a group together, it can be two people or more than two, I want them to be transparent with each other about their most negative thoughts, because if they withhold those negative thoughts, then they simply just resent each other. And so whether I'm asking for feedback to me or asking them to give feedback to each other, I ask them not to say anything, but to think of the thought they have about this other person, again, me or someone else that would hurt that person's feeling the most, not to say it, just to think it. And then once they have that thought in their brain chamber, do you have it? And they say, yes. Okay, great. Now I'd like you to say it. And then they do. And then what we usually discover after that is that the person who received it is really appreciative because they don't want anyone else to be walking around with negative feelings. And so once I receive that information, I can do something about it. But if I never hear that information, then I'm just walking blind and I'm pissing people off and not even knowing that I'm pissing them off and certainly not knowing how to fix it.

AI assessment note: “I want them to be transparent with each other about their most negative thoughts”

Q If we think about kind of the more negative perspective and the not good results, if it works, it works brilliantly well. If you have that transparent conversation and the person reacts negatively, how do you see those situations playing out? And how do you look to conflict resolve in the situations where the person really takes it almost offensively and the negative situation then ensues? What's that next step?

A First of all, for me, that's when it gets fun, but yes, that does happen on occasion. And the key is when someone gets triggered, when they're in anger, The key is for them to release that anger, and they often don't know how to do it, and so I'll help them. And one of the easiest ways is to simply have their anger named and their thoughts named. So I will simply say, hey, I sense that you're feeling a lot of anger right now, and my guess is that some of the thoughts you're having are blank, and then I'll really go for it. I'll say some thoughts that are just laden with F-bombs and every expletive you can think of, And they're all focused on me and saying just the worst things about me I can possibly think of. And that usually has the person visibly release and relax. First of all, you try to go beyond what they were actually thinking. So now it makes it okay for them to have these thoughts, which are actually less than what I said. And it sort of gets it out in the open and they feel heard. And when people feel heard, both for their feelings and for their thoughts, they're able to relax and let them go.

AI assessment note: “one of the easiest ways is to simply have their anger named and their thoughts named.”

Q suck at this. That's often a situation where I have where it could be, you know, something that I love and I, you know, hopefully I'm good at being kind of network people, relationship building, and then stuff that I suck at, legals, transactions, you know, financial models. How do you determine whether someone should get good at what they're bad at or double down on what they're good at?

A So first of all, it's not about whether they're good at something or bad at something, it's whether or not they love it. Now, typically, if they're bad at something, it's because they hate it, and therefore it They don't want to do it. They don't want to invest in studying how to do it. They don't want to practice it. So they do it just the bare minimum required, which of course no one talked about bare minimum equals phenomenal. People talk about 10,000 hours, not 10 hours. And so they obviously don't get good at it because they don't want to do it. To me, the key is their whole series of actions that need to occur within any one job function. But it doesn't mean, for example, CEO. There are a whole bunch of things that a CEO role needs to take care of. But it doesn't mean that the name CEO needs to do all those things. It just means that the name CEO needs to make sure all those things get done and get done well. So there's an example of someone I coach who luckily had as a co-founder who is very symbiotic. One is an extreme extrovert. The other is an extreme introvert. And originally they had split up their tasks. 50, 50 half the team reported to one half the team reported to the other. When fundraising, one would take half the meetings. The other would take half the meetings. And it turns out that one is an extreme extrovert, and one is an extreme introvert. And so the extr…

AI assessment note: “it's not about whether they're good at something or bad at something, it's whether or not they love it.”

Q like creating a real relationship of trust and intimacy. And it's something that, as I said, so many of the people that we mentioned before have mentioned you being excellent at. How do you think about creating that relationship of real intimacy and trust and a safe environment where I can bring anything to you and I know that actually it's going to be a warm and a receptive environment?

A So for me, there's one tool and one tool only, which has brought me this and it's an easy one. So I'm going to share it with you and everyone listening. And that is in every single interaction that I have, whether it's one-on-one with someone or in a group at the end, I always ask for written feedback, not just verbal feedback, ask everyone to write down on a doc. Can you please tell me what happened in this interaction with me that you like and what happened that you wish that were different? How could I have been more effective? And of course I encourage people to get as brutal as possible. And when they do get brutal, I appreciate it. I repeat it back to make sure that they know that I understood what they said. And then if I accept it, which I almost always do, then I declare what action I'm going to take against it. And when that happens, people realize, wow, I can actually change how Matt behaves with me. And therefore now any discomfort they have, they can eliminate just by telling me about it. And then it's gone. And in fact, oftentimes trust gets created the quickest, When there actually were real discomforts that people had in their first interaction with me, and then they shared those with me, and I went, that's awesome. Thank you. Here's what I'm going to do. And they realized, oh my God, this guy's actually walks the talk. He doesn't just talk about it. He actually…

AI assessment note: “there's one tool and one tool only... I always ask for written feedback”

Q This is probably why I need coaching. I'm so emotionally detached. Um, so tell me, I spoke to Henry there at Brax. How do you feel about the rise of chief of staffs?

A Oh, I think it's brilliant. It is the answer for extending oneself when no other hack remains. So once you've done inbox zero and you've automated everything you possibly can, but the world is still asking for more from you and you want to respond, unfortunately it requires another human. And the key about a chief of staff, however, is the way that you train them. And the best way to train chief of staff is to give them full access. They have complete access to your email, to your calendar, to every meeting that you're in. So they literally sit beside you, listen in on every call and sit in every meeting. And that lasts for probably one to two months until they fully grok how you think, because they see the information you take in and they see the decision you make. And now they can start to correlate and pattern match. And then they can start to act literally on your behalf as you would. So that's the key though. The key is giving them full access.

AI assessment note: “Oh, I think it's brilliant. It is the answer for extending oneself”

Q Not at all, but I, I do want to kick off with a little bit on you. So over the last few years, you've become really the Oracle coach of the leading Valley CEOs. So how did you make your way into the world of startups, Matt? And how did you come to the position you are today?

A Well, I, I made my way into startups three different ways, three different times. The first as an investor, when I was quite young, just had a business school at a growth equity fund. And that was in the late nineties when the internet heyday one point O began and it just went crazy. And then I became a partner, but a very junior partner. And I realized if I want to really participate in this wave of value creation, I have to start my own company. So I did, I left that firm, which was a scary thing to do because that was sort of a guaranteed track to success. And I founded a company with a friend. And again, at the time it was the late nineties was 99. It was just insane. He raised hundred and thirty million dollars, hired 280 employees. It was just crazy. And luckily that worked out financially. We were terrible operators, but at that time it just didn't matter. And so that was a great financial event for me. And then I decided I wanted to do other things, but eventually I came back to Silicon Valley. Once my wife and I started having kids, we decided we could live anywhere in the world. And we decided that Silicon Valley was to us the best place to raise a family. I know that sounds odd, but to us, it was phenomenal. Once we came back here, I wanted to be part of the community again, but I didn't want to start another company because starting a company is a lot of work and th…

AI assessment note: “I made my way into startups three different ways, three different times.”

Q Advice here. You should definitely invoice me for this session as well. Um, but it's like often I'll have angry thoughts and then there's this kind of negative cyclicality around the angry thoughts because I'm angry at myself for having the angry thoughts in the knowledge that it is unproductive and potentially unfair. How do you think about self-resolution when you're kind of cyclically angry at yourself for being angry?

A Well, first of all, you've already gone deeper than most in that you've recognized there's a cycle. What's interesting is you're identifying, you get angry at someone else and then you get angry at yourself. I posit that really you're critical of yourself first, and it's those things about yourself that you don't love that you're critical of other people for. So a way to start resolving this is to start thinking, when did I first in my life, when did I first notice this anger appearing? And where in my childhood was this triggered? Was this created? And once you can see that early formation of the self-critical voice, you can realize, oh, as a five-year-old boy, I can completely understand why a five-year-old boy Would start to criticize himself when someone else was criticizing me. I completely get that. But as an adult, do you still want to operate in that same way? Is it still serving you now? No, it's not. So now you can sort of say, thank you. That old way of being, which by the way, helped you get to where you are. So it was very valuable for you. The voice is never going to go away, but you can stop acting on the voice and you can start replacing it or adding another voice, which is complimentary of yourself and appreciative of all parts of you, even the parts that you don't necessarily wish you had.

AI assessment note: “start replacing it or adding another voice, which is complimentary of yourself”

Q That's amazing to hear. I mean, I think that's the sign of like the truly special relationship that you build in that relationship itself. Tell me, what would you most like to change about tech in the Valley today? You have this incredible perspective in the role that you sit in. What would you most like to change?

A I think that the tech world has received many benefits and I don't think that we've yet shared those fully enough. With the country that we sit in or the world that we live in. And so YC has started to do this. They've started to create and support entities that solve social ills in the country and in the world. And I think the rest of Silicon Valley needs to follow suit. I'm going to be pushing all of my coaches to follow suit. And one, it just feels good. And two, I think there's a matter of self-preservation here. We're already seeing the backlash of Senator Warren saying, hey, rip apart the The tech world. And there's a reason for that. There's a reason because the tech world is seen as sitting apart, sitting above, not being interested in helping the United States solve the social ills that face it today. And I think we need to get involved, get our hands dirty and start solving them. I mean, pledge one percent is a very easy way to start. And I think all companies should do it.

AI assessment note: “I don't think that we've yet shared those fully enough.”

Q interesting that you asked for the kind of written feedback, and I love it. But, you know, often founders, especially founders with large cap tables and big boards, get a lot of feedback. And you know, I get a lot of feedback too. And my question to you is how do you advise founders and how would you advise me on the feedback to take versus what to respectfully disregard?

A It's whatever resonates with you. So if you hear something and you think, oh yeah, you know, that did happen. And now I can see how that made you feel negative. And I really wish that hadn't happened. Then that resonates with you. So you accept that feedback and you co-create actions to mitigate it going forward. But if the feedback is something that does not resonate with you, Then no, you do not need to accept it. I think you do need to say thank you, and you do need to reflect back what it is that they said so that they know that you've heard them, but you don't then need to accept it. If you had to accept every bit of feedback, that would be tyranny of the feedback giver, and it would be a terrible world that we'd be living in.

AI assessment note: “It's whatever resonates with you... if the feedback is something that does not resonate with you”

Q suck at this. That's often a situation where I have where it could be, you know, something that I love and I, you know, hopefully I'm good at being kind of network people, relationship building, and then stuff that I suck at, legals, transactions, you know, financial models. How do you determine whether someone should get good at what they're bad at or double down on what they're good at?

A So first of all, it's not about whether they're good at something or bad at something, it's whether or not they love it. Now, typically, if they're bad at something, it's because they hate it, and therefore it They don't want to do it. They don't want to invest in studying how to do it. They don't want to practice it. So they do it just the bare minimum required, which of course no one talked about bare minimum equals phenomenal. People talk about 10,000 hours, not 10 hours. And so they obviously don't get good at it because they don't want to do it. To me, the key is their whole series of actions that need to occur within any one job function. But it doesn't mean, for example, CEO. There are a whole bunch of things that a CEO role needs to take care of. But it doesn't mean that the name CEO needs to do all those things. It just means that the name CEO needs to make sure all those things get done and get done well. So there's an example of someone I coach who luckily had as a co-founder who is very symbiotic. One is an extreme extrovert. The other is an extreme introvert. And originally they had split up their tasks. 50, 50 half the team reported to one half the team reported to the other. When fundraising, one would take half the meetings. The other would take half the meetings. And it turns out that one is an extreme extrovert, and one is an extreme introvert. And so the extr…

AI assessment note: “it's not about whether they're good at something or bad at something, it's whether or not they love it”

Q Advice here. You should definitely invoice me for this session as well. Um, but it's like often I'll have angry thoughts and then there's this kind of negative cyclicality around the angry thoughts because I'm angry at myself for having the angry thoughts in the knowledge that it is unproductive and potentially unfair. How do you think about self-resolution when you're kind of cyclically angry at yourself for being angry?

A Well, first of all, you've already gone deeper than most in that you've recognized there's a cycle. What's interesting is you're identifying, you get angry at someone else and then you get angry at yourself. I posit that really you're critical of yourself first, and it's those things about yourself that you don't love that you're critical of other people for. So a way to start resolving this is to start thinking, when did I first in my life, when did I first notice this anger appearing? And where in my childhood was this triggered? Was this created? And once you can see that early formation of the self-critical voice, you can realize, oh, as a five-year-old boy, I can completely understand why a five-year-old boy Would start to criticize himself when someone else was criticizing me. I completely get that. But as an adult, do you still want to operate in that same way? Is it still serving you now? No, it's not. So now you can sort of say, thank you. That old way of being, which by the way, helped you get to where you are. So it was very valuable for you. The voice is never going to go away, but you can stop acting on the voice and you can start replacing it or adding another voice, which is complimentary of yourself and appreciative of all parts of you, even the parts that you don't necessarily wish you had.

AI assessment note: “So a way to start resolving this is to start thinking, when did I first”

Q interesting that you asked for the kind of written feedback, and I love it. But, you know, often founders, especially founders with large cap tables and big boards, get a lot of feedback. And you know, I get a lot of feedback too. And my question to you is how do you advise founders and how would you advise me on the feedback to take versus what to respectfully disregard?

A It's whatever resonates with you. So if you hear something and you think, oh yeah, you know, that did happen. And now I can see how that made you feel negative. And I really wish that hadn't happened. Then that resonates with you. So you accept that feedback and you co-create actions to mitigate it going forward. But if the feedback is something that does not resonate with you, Then no, you do not need to accept it. I think you do need to say thank you, and you do need to reflect back what it is that they said so that they know that you've heard them, but you don't then need to accept it. If you had to accept every bit of feedback, that would be tyranny of the feedback giver, and it would be a terrible world that we'd be living in.

AI assessment note: “It's whatever resonates with you.”

Q of self-doubt and often feel this kind of intense imposter syndrome, be it through the show and kind of the size of the show, and then also kind of through the fund and investing. I'd love to hear your thoughts. You work with some incredible young first-time founders. How would you advise me? How do you advise them? When it comes to really handling and managing this intense imposter syndrome.

A So again, imposter syndrome is fear. And so you're feeling it. And the way to, I think, overcome fear is to start recognizing where you feel joy and then taking the pieces of the things that you do that you don't enjoy and removing them. So I may not be answering your question directly, answering it indirectly, but I think it's going to work. And so this is the energy audit. This is where you print out your calendar for the past, let's say two weeks and hour by hour, you take a red marker and a green marker and you mark each hour, whatever activity you did during that time, did it create more energy at the end of the hour? Did you feel energized or did you feel depleted? And it's one or the other. If you felt neutral, that's a red. So either it gave you energy or it didn't. And if you start marking those, you'll find there are a few and you then go back and look at all the reds. You'll see there's some patterns. So maybe having LP meetings doesn't energize you. Or interviewing people who you end up not hiring. That is an energy drain for you. Or having difficult conversations with team members. That's whatever it is. There are instances that are energy draining for you. Then there's three possibilities for you. One is you can outsource those tasks. Two is you can just stop doing them all together and have no one else do them. They may not even be necessary. Or three, if you rea…

AI assessment note: “the way to, I think, overcome fear is to start recognizing where you feel joy”

Q person is? I spoke to many of the people that you've worked with before, and it was actually quite a few of them that said, you ask very provocative questions, and they said you'd get away with it. My question to you is, how do you do that? And are there commonalities to the questions that you ask that are provocative, pressing to really determine the nature of the person?

A Well, I'm going to try to think of what these provocative questions are. I think one that probably feels provocative is when I have a group together, it can be two people or more than two, I want them to be transparent with each other about their most negative thoughts, because if they withhold those negative thoughts, then they simply just resent each other. And so whether I'm asking for feedback to me or asking them to give feedback to each other, I ask them not to say anything, but to think of the thought they have about this other person, again, me or someone else that would hurt that person's feeling the most, not to say it, just to think it. And then once they have that thought in their brain chamber, do you have it? And they say, yes. Okay, great. Now I'd like you to say it. And then they do. And then what we usually discover after that is that the person who received it is really appreciative because they don't want anyone else to be walking around with negative feelings. And so once I receive that information, I can do something about it. But if I never hear that information, then I'm just walking blind and I'm pissing people off and not even knowing that I'm pissing them off and certainly not knowing how to fix it.

AI assessment note: “I think one that probably feels provocative is when I have a group together”

Q for first time founders on the flip side is in terms of obviously for me now sitting on boards and for founders who have to do board management effectively. I'm interested having worked with some of the best CEOs of the last five to 10 years. What would you advise me in terms of being the best board member I can be having had the incredible experience that you have?

A First of all, know that boards are the death of every great investor. So Be wary. If you sell to founders that when they take your money, you will join their board and be on their board forever. Know that you have just ended your career eventually. And the reason is boards take up a tremendous amount of time. And so, you know, there's at least four year, if not more, they're usually half a day to a full day. Often you have to get on a plane to go to them. So there's travel back and forth. And now you're on four, but imagine when you're on 10 and then 15 and then 20, and you've made this commitment to be on them forever. So you can't get off, or at least you think you can't get off. And now, 40 to 50% of your time is spent attending board meetings. And you have to, of course, spend, if you have partners, you have to have 20 to 30% of your time doing internal meetings, you know, investment committee, et cetera. That leaves another 25% of your time to just simply support your portfolio companies or do other sort of random things. And now you have zero time to look for and make new investments. So be very wary. Don't sell a lifetime commitment on a board. Sell, support. That's what's valuable. And what's valuable to CEOs is the support they want, not the support that you want to give. So simply ask them, how can I be most helpful to you? And they will tell you. And usually it's not…

AI assessment note: “simply ask them, how can I be most helpful to you? And they will tell you.”

Q Can I ask what environment and tone are the right environments and tones to do it and have those very hard conversations in?

A Well, the challenge is, of course, is that there's a reason most people don't share negative things, and it's because in their experience, if they deal with conflict head on, it usually ends negatively. So their experience growing up in the school ground is they said something to someone, and it ended up being a fist fight in the playground. Or later on in relationships, they shared something with their spouse, and it ended up being a screaming match. And so their experience towards conflict is negative. And so the key, of course, is to teach people how to share difficult subjects and In a way that doesn't trigger the person who's hearing. And so that's where I come in. And this is not stuff that I've invented. This is, you know, there's a book called difficult conversations, radical candor. Those are just two. There are many more that describe effective processes for sharing information. Basically it's instead of saying, Hey, you did this, you shouldn't have done that with a finger pointed in their face. That will make them feel very defensive. If on the other hand, it's simply, Hey, this is my perspective. I feel anger. Okay. That doesn't trigger anybody. It's just a feeling I have. And my thought is this. I'm not saying this is right. It's just a thought in my head. Okay. That's a thought in your head. Great. And by the way, I have a request and here's my request. Great. So …

AI assessment note: “instead of saying, Hey, you did this... it's simply, Hey, this is my perspective”

Q Can I ask what environment and tone are the right environments and tones to do it and have those very hard conversations in?

A Well, the challenge is, of course, is that there's a reason most people don't share negative things, and it's because in their experience, if they deal with conflict head on, it usually ends negatively. So their experience growing up in the school ground is they said something to someone, and it ended up being a fist fight in the playground. Or later on in relationships, they shared something with their spouse, and it ended up being a screaming match. And so their experience towards conflict is negative. And so the key, of course, is to teach people how to share difficult subjects and In a way that doesn't trigger the person who's hearing. And so that's where I come in. And this is not stuff that I've invented. This is, you know, there's a book called difficult conversations, radical candor. Those are just two. There are many more that describe effective processes for sharing information. Basically it's instead of saying, Hey, you did this, you shouldn't have done that with a finger pointed in their face. That will make them feel very defensive. If on the other hand, it's simply, Hey, this is my perspective. I feel anger. Okay. That doesn't trigger anybody. It's just a feeling I have. And my thought is this. I'm not saying this is right. It's just a thought in my head. Okay. That's a thought in your head. Great. And by the way, I have a request and here's my request. Great. So …

AI assessment note: “it's all centered on me, centered on my feeling, my thought, my request.”

Q of self-doubt and often feel this kind of intense imposter syndrome, be it through the show and kind of the size of the show, and then also kind of through the fund and investing. I'd love to hear your thoughts. You work with some incredible young first-time founders. How would you advise me? How do you advise them? When it comes to really handling and managing this intense imposter syndrome.

A So again, imposter syndrome is fear. And so you're feeling it. And the way to, I think, overcome fear is to start recognizing where you feel joy and then taking the pieces of the things that you do that you don't enjoy and removing them. So I may not be answering your question directly, answering it indirectly, but I think it's going to work. And so this is the energy audit. This is where you print out your calendar for the past, let's say two weeks and hour by hour, you take a red marker and a green marker and you mark each hour, whatever activity you did during that time, did it create more energy at the end of the hour? Did you feel energized or did you feel depleted? And it's one or the other. If you felt neutral, that's a red. So either it gave you energy or it didn't. And if you start marking those, you'll find there are a few and you then go back and look at all the reds. You'll see there's some patterns. So maybe having LP meetings doesn't energize you. Or interviewing people who you end up not hiring. That is an energy drain for you. Or having difficult conversations with team members. That's whatever it is. There are instances that are energy draining for you. Then there's three possibilities for you. One is you can outsource those tasks. Two is you can just stop doing them all together and have no one else do them. They may not even be necessary. Or three, if you rea…

AI assessment note: “So I may not be answering your question directly, answering it indirectly”

Q the people you work with, it is the most incredible list from the last five years. I'm super interested, and actually, Emily Choi asked this one. And she said, when you think about the incredible people you work with, and the many, many people now that asked to work with you, how do you select the CEOs you choose to work with, and who do you opt into, and why?

A So right now, I'm not taking on any new co-chiefs, but in the past, when I have, it really was just sort of a one-time thing. I was introduced to Naval Ravikant of AngelList about two and a half years ago, and this is when I was sort of still in my Stanford days, and he met with me. We sat down from my house for about an hour and a half. He had this big issue that had been Plaguing him for a decade. And we unpacked it and figured out a roadmap to solve it. And six weeks later, he'd implemented the roadmap and problem completely solved. And so he came back to me and said, Matt, I know all the coaches and you are the best coach in the world. And I thought, that's crazy. But then I thought about it for a bit and said, well, let me test it out. If that's true, then I should be able to coach anybody I want to. So I made a list of the 20 people that I'd be interested in coaching. And I shared it with Naval. And I said, Naval, do you know anyone on this list? And he says, yes, I know one person. I know Brian Armstrong at Coinbase.

AI assessment note: “So right now, I'm not taking on any new co-chiefs”