Matt Mochary, Coach To Silicon Valley's Leading VCs & Founders on How To Deal with…

Well, thank you so much for having me. This is fun for me.

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 out of business school at a growth equity fund. And that was in the late 90s when the Internet heyday 1.0 began began and it just went crazy. And then I became a partner, but a very junior partner. And I realized if I want really participate in this wave of value creation, I have to start my own company. So I did. I left that firm, which is a scary thing to do because I 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, it was ’99, It was just insane. We raised $130 million, 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, was phenomenal. Once we came back here, I wanted to be part of the community again, but I didn’t want start another company because starting a company is a lot of work. and and the result is more money. And that’s not what I needed or wanted. But I really wanted get involved. I thought, well, maybe I can become a coach. That way I can be involved in all the fun stuff, which is the decision making and the strategic thinking, but I don’t actually have to do the work.

So that’s what I started doing. But I thought, but I’m not a coach, so therefore, who’s to want me as their coach? Well, only the people who can’t get a coach. To me, that was students who were still at Stanford because no one wanted to coach them. They were students, and YC wouldn’t even accept them into their class. So I started coaching some students at Stanford who created real companies, and it was super fun and created a ton of value, it seemed. And they started recommending me to other people, people who had graduated a few years earlier, and I sort of walked up the ladder from there.

Yeah, Well, at the time, it was just I felt the blinding need to do it. I think it was a fear of not taking advantage of the wave. Fear is an incredible motivator, and I think that most people, including myself in my earlier days, that was my main motivation. Now in my later years, I’ve learned to replace that with joy, which is an even greater motivator and certainly much more pleasant. But at the time, it was fear. I just feared missing out. That’s all.

So this really comes from our brain physiology as humans and our history that has created how we behave. And so Robert Sapolsky wrote a phenomenal book called behave. I won’t go into the detail, but if anyone’s interested, they can watch his videos or read his book and explains the entire brain physiology. But the basic is is that we have a prefrontal cortex where our creative thought occurs and we have an amygdala where when we’re in fear and anger, our brain activity goes. And when we’re in fear and anger, our brain activity is primarily fight or flight.

There’s a thing in front of me that is a threat. Am I either going try to kill it or run away from it? And as you can imagine, those are not very creative thoughts. And in the world of I’m being chased by a saber toothed tiger, yes, those are effective thoughts to have because they keep me alive. But in the world of business, modern business, those thoughts don’t lead to optimal actions. And so the key is to recognize when am I in fear and anger. And that’s not an easy thing to do.

And there are some who meditate day after day, year after year, and eventually become self aware enough to notice when they get triggered and go into fear and anger. But most of us don’t have that ability. I don’t have that ability. And so I use a hack, which is a lot easier. I just tell the people around me, can you please let me know when you notice me in fear or anger? And if anyone around me ever says, Matt, fear, Matt, anger, I just go, oops.

And I stop and I wait until that feeling passes because I know the thoughts associated with it are basically Neanderthal thoughts.

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 than 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.

Let’s take a real situation. What is one that has really made you feel fear or feel anger? juicier, by the way.

So in the way you described it is someone did this, someone created a term sheet. They did this to you. almost They were trying to bully you. And that’s the external perspective. Now let’s go to the internal perspective. What did you do to help create that situation?

And now what can you do to unwind it?

What about also the option of being blunt with the founder saying, listen, I feel fear and the thought I have is I do not understand all these terms. I would like to invest in you, but I would like to invest you in terms that I understand. And therefore, would you be open to making this simpler and making this more something that I’m used to seeing?

I think just the opposite. I think in my experience, when I or others that I coach have shared their vulnerability and their true thoughts and their true feelings, that people have become more connected to them and felt closer to them. I mean, the master of this is Peter Fenton at Benchmark. He within five minutes of any conversation, he will tell you a weakness that he has. And it’s not he’s not joking about it. He tells you a real weakness. And my God, it makes me love him.

But I’m not unique in loving him. Everybody I know loves Peter Fenton and that’s why I think.

I’m 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.

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 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, 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 it’s all centered on me, centered on my feeling, my thought, my request. You don’t have any responsibility here. There’s no fault. There’s no blame. And then the person receiving can hear it. And if they want act on it, they can, but they don’t have to.

No, absolutely. There has to be. You can’t force this upon someone in the middle of them being stressed about another situation or being in the middle of another task. So the key is to simply reach out and say, hey, I’d like to clear something with you. Is now an okay time for you? And they’ll answer you and they’ll say, nah, now’s not really good. I’m under the gun. I’ve got a deadline. But how about, you know, Tuesday at 2:00? Okay, great. So allow the timing of this needs to be agreed upon.

If you force someone into this, you will not get a good result.

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.

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 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 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.

So what you’ll find is, is, that almost all of these thoughts got created when you were less than five. They probably all got created before you even have memory in 2, 3, 1 year old. So I don’t know any that have gotten truly created post five or six years old.

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? look 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 can stop doing them altogether and have no one else do them. They may not even be necessary. Or three, if you really believe that you have to do them and they have to get done, then you can find out ways say, well, it would be acceptable to me.

It would be actually energy raising as long as the following things happen and you sort of write out what a criteria for an exquisite experience would be and then try to make that happen. Those are your three choices. And what I find is it’s a very simple exercise. It usually helps to have a thought partner do this with you because often they sort of push you to think of options that you don’t think are possible yourself, And then implement that. days later, do the same thing.

Look at your calendar again, mark how many greens and reds. Hopefully there are more greens this time, less reds. And then you go through the same process. And then do it again days after that. What you’ll find is usually by month three, once you’ve done this three times, your calendar will be mostly green, mostly energy raising, and you will find yourself, I believe, feeling tremendous amounts of joy. And that fear will likely have dissipated a lot, if not entirely.

So first of it’s not about whether they’re good at something or bad at something, is whether or not they love it. Now, typically, if they’re bad at something, it’s because they hate it and therefore, they don’t to do it. They don’t to invest in studying how to do it. They don’t 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, hours, not hours. And so they obviously don’t get good at it because they don’t want 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 named CEO needs to do all those things. It just means that the named 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 has a cofounder 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 meeting. And it turns out that one is an extreme extrovert and one is an extreme introvert. And so the extreme introvert loved all the internal meetings and hated all the external meetings. And the extrovert loved all the external meetings and hated all the internal meetings.

And so when I asked this question of what do you love and what do you hate, it became very obvious how they should rearrange their responsibilities. And then they did. And now one is external only and the other is internal only. and the results have been palpable.

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, 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 give. So simply ask them, how can I be most helpful to you? And they will tell you. And usually it’s not strategic thinking because you have very little information about the company. They’re at the company days a month, 12 hours a day.

They have so much more information than you do. But what you have that they don’t is you have a network, and they need introductions and warm introductions to customers, to other investors, to recruits. That’s the most valuable thing to most CEOs.

Yes.

That’s okay. I’m not saying I’m right. No, that’s a thought in my head.

So for me, there’s one tool and one tool only which has brought me this, and it’s an easy one. I’m going share it with you and everyone listening. And that is in every single interaction that I have, whether it’s one on with someone or in a group, at the end, I always ask for written feedback, not just verbal feedback. I 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 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 to do. And they realized, oh my God, this guy actually walks the talk. He doesn’t just talk about it. He actually does it. And that’s what for me, I think creates the trust and like so quickly.

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 cocreate 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 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.

So right now, I’m not taking on any new coaches, 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 implemented the roadmap and problem completely solved. And so he came back and me, said, Matt, I know all the coaches and you are the best coach in the world. 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? He says, yes, I know one person. I know Brian Armstrong at Coinbase. Great. Can you please introduce me? So he did. And then coached Brian for a while until there was deep trust there. And I said, Brian, I showed him the list. Do know anyone on the list? I said, yes, I know Sam Altman. I said, great. Can you please introduce me? He did. I then started coaching Sam again. when Deep trust was created, I shared the list with him and I said, Sam, do you know anyone on the list? he said, yes, I know them all. he introduced me to them and not all of them said yes.

About half of them said yes. I’m coaching about half of those folks. And that’s how it happened.

Sounds great.

Perfect.

Oh, High Output Management, Andy Grove. That’s the bible for me.

Right now, balancing. In 2019, I was a glutton. I love coaching so much that I took on more and more and more and more and more and I ended up being coaching from eight in the morning till eight at night, five days a week, and that was just too much. I stopped seeing my family enough. So now it’s almost like I’ve got back off the addiction because I do really enjoy spending time with my family. So balance is the biggest challenge for me right now.

I don’t find them to be challenging. I find them to be energy raising. So, no, I gain energy with every coaching call and coaching meeting that I have.

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 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 a 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.

If you wait till you get your shit together, it’ll never happen. So no, you start with them and they’ll help you get your shit together.

Well, this is just a signal of respect. If I don’t respect you, then I don’t care about your time. And so if I’m late, then I won’t even tell you about it, and I’ll just make you sit there and wait for me. And the person on the receiving end, you know, they hate it and they won’t tell you, but they will probably hate you for it. And so I just don’t do that. I am either on time, but that’s actually not the important thing. The important thing is letting someone know that I’m not going be on time.

So if I’m even to be one minute late, as soon as I realize that, I just sent him a text saying, hey, sorry, No. I’ll be there at 9:01 instead of 9:00am and that allows them to not wonder what’s going on when I’m to show up. It also allows them to keep working and being productive in the interim time, not stop their work and sit around twiddle their thumbs waiting for me. And so the key is not being on time. The key is just letting people know when I’m not going be on time.

You were indeed.

Well, funnily enough, I become very close friends with the people I coach. and so they end up becoming. And they often say, hey, Matt, you’ve coached me so much and helped me so much. I’d like to coach you a little bit. I go, great. And so they do, and they’re the ones who support me. You know, Sam Altman and Enrique and Alex at Clearbit have helped me tremendously in my life.

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 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 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 1% is a very easy way to start, and I think all companies should do it.

I have no idea because I don’t have ambitions or goals anymore. I simply live in the moment of am I feeling joy? And if I am, I keep doing it. And if I’m not, I stop. So that’s a good question, but one I don’t have an answer for.

Awesome, Harry. It was really fun for me.