Building What Lasts: Brad Feld on Trust, Mentorship, and Long-Term Thinking

Hello, everyone, it's Guy Kawasaki. I believe we are in troubling and dangerous times. One of the things that's happening is that privacy is eroding. And when privacy erodes, so does democracy. So Madison Knysberg and I, we just finished a book. It's called Everybody has Something to Hide. This is a jargon free book. It is for everybody to learn why and how they should use signal. They should use signal to ensure their privacy, safety and well being. It comes out on January 28th. For five days, it'll be free and then it'll go to $4.04. I hope you see what we did there. The forward is from Congressman Ro Khanna because he believes, like we do, that democracy is extremely important and signal is one of the tools that can help us preserve democracy. So remember the name Everybody has Something to Hide. It's by Guy Kawasaki and Madison Nismer.

So foundational difference between the two is that Pay it Forward has this transactional component. I'm doing this out of obligation. I'm doing this because somebody once did it for me. Give first is just a philosophy. It's a way of being. It's a way that you approach things. And it's important to recognize the difference, I like to say, in this concept between religion and philosophy. Give first is a philosophy. Religions are. If you do this and you do all these good things, theoretically, some good thing will happen to you.

Hello, everybody, it's Guy Kawasaki. This is the Remarkable People podcast and we have found another remarkable person to inspire and to inform you. Arguably, he is the second most famous person from Arkansas in entrepreneurship. There's another guy who started it with a few stores, but anyway. I would say, however, that Brad Feld, our guest, is the black swan purple cow of venture capitalist because he has a very unique attitude in venture capital about giving first, like his book Give First. And so his concept is that you can create trust and momentum and a strong, strong sense of community by being generous and giving without the expectation of return. And let's just say that generosity is not a term that's usually associated with venture capitalists. Right, Brad and he co founded techstars and the Foundry Group. And he's been a big factor in how people start startups. And as I said, I have his book. His book is called Give first. And this interview will be largely about giving first. All right, Brad, welcome to Remarkable People.

Brad, Guy, it's a delight and an honor to be here.

I wouldn't go that far, Brad, but.

Oh, you don't know. You're one of my heroes. So it's actually a real joy. I got my first Apple computer when I was 13. I was bar mitzvahed and got it from my bar mitzvah. But then When I was 17, I was introduced to the Macintosh and I knew the name of four people at Apple. Steve Jobs, Steve Wozniak, Al Eisenstadt, which is a totally another story, and Guy Kawasaki. Okay.

Al Eisenstadt, of all people. I don't know if I should tell you this, but I used to go out with Al Eisenstadt's daughter, Melissa.

Ooh, that's, that's spicy. I did not expect, I did not expect that. At the lead of this.

There is nobody at NPR who could have started a podcast with that statement, I guarantee you.

That's right. That's right.

Al Eisenstadt had this Porsche 928. It was such a cool car. But anyway, let's not go down that Rabb.

He was wonderful to me. I showed up at Apple. I don't remember. I was 15 or 16 years old. My parents took me on a trip to California. I grew up in Texas and I really wanted to see Steve Jobs. Take me to see Steve Jobs. And my parents are like, all right, we'll try to figure out how to get to see Steve Jobs. And we show up at Apple and I am introduced to this very, very sort of, you know, I'm a small kid, big guy. Al Eisenstadt. Hello, I am Al Eisenstadt. It's nice to meet you. Mr. Jobs is not available today, but I am here to say hello to you. And he ended up sitting with me for about 30 minutes. Like why in the world he spent 30 minutes with his 15 year old kid. And he was so generous with his time and such a delight. And I asked him all these nerdy little questions that a 15 year old kid at the time cared about Apple and he was great.

That so sounds like Al. Now people are wondering, who the hell is Al Eisenstadt? I never heard of Al Eisenstein. Well, Al Eisenstadt was the general counsel of Apple, so he was a BFD pal. Yeah, you might not have been talking to Steve Jobs, but you were talking to the person who kept Steve Jobs out of jail. So, you know, it was kind of a full time job.

He did not take me for a ride as 9:28, but we had a lovely, we had a lovely 30 minutes in some conference room.

Well, if you were dating his daughter, he would have. But anyway, so listen, I'm going to Start you off with a real easy question. Just ease into this interview.

All right, let's do it.

Say yes.

Yes.

Okay.

Okay, Brad. So let's say that if Elon Musk or Peter Thiel or Mark Zuckerberg or any of those people, any of those bros, if they read your book, in my humble opinion, they would be laughing or throwing up. The concept that you should give first is so foreign to those tech bros. So what's your reaction to what's going on in Silicon Valley and tech these days?

For starters, I have a very simple view about this particular book. It's the ninth book I've written and you've written a bunch of books, and my guess is your view is the same. If you like the book, tell the world. If you don't like the book, throw it away. So, you know, at a high level, my view is people can decide how they want to be, however they want to be, and that's their choice. Personally, I'm exhausted with the shtick of Silicon Valley. I've never been of Silicon Valley. I've been there and invested in many companies in the Bay Area. I spent a lot of time physically there over the years. There was about a seven year period where I lived part time in Atherton at my business partner Heidi Roizen's house. So when I would come.

Wait you time out here. You lived at Heidi Roizen's house?

I did. So Heidi had a house in Atherton on.

Yeah, one mile from mine, one mile from Al's.

There you go. Stockbridge, remember?

Yeah.

And I would come to the Bay Area Monday morning. From 1996 to 2006, I was in the Bay Area 50% of the time and not 25 to 50% time. But I'd show up on Monday morning and I'd leave on Monday night, Tuesday night, Wednesday night. And I'd often fly to New York, take a red eye across to New York, but I would stay at Heidi's house. That's where I lived. So I grew up with her kids and her now ex husband, David and Marlena. And at the time their name was Nikki. And it was a wonderful experience, but it wasn't my place. Like, I ran through all the neighborhoods. I was a big runner. So I'd run all around and just it was fine, but it wasn't my place. And I never really got into the vibe of it in a way that sort of hooked me. And when I think about that time period where I was there a lot though, even though it wasn't my place, like There was a. A sort of a style, an approach, an optimism, the cliche that, of course, I think the only person that should be allowed to say it was Steve Jobs. The idea of, I'm going to put a dent in the universe as these things became nonsensical lines that people were saying, I'm going to change the world. Well, what the fuck does that mean? I'm going to change the world, so it's better for me. Okay? And, you know, eventually I just got to the point where I'm like, you know what? That's not my. Everybody's got. Everybody has their shtick, and everybody's entitled to their shtick. That's not my shtick.

They are certainly putting a dent in democracy, but. Okay, and now I'm going to show you my deep knowledge of things Jewish. You have in your book, 18 recommendations that you call the Mentor Manifesto.

You got it?

And I think that there are 18, because 18 is the Hebrew word for life, chai. And chai is made out of two characters. One means 8 and one means 10. And so the number 18 is considered very lucky by Jewish people. So you made 18 recommendations in the manifesto, is that right?

You are the first person out of a zillion podcasts that I've done that. Got that. That is awesome. I keep waiting. Every time I do a podcast of this book, I keep waiting, and you got it, guy. You're like my double hero now. You totally got it. Now here's the really ironic or entertaining. It's not ironic, it's entertaining. Part of that is that was not deliberate. David Cohen, when he came up with the Techstars Mentor Manifesto in 2010, didn't think very hard about it. By this point, we were three or four years into techstars, and we learned the difference at this point, I think, between effective mentorship and ineffective mentorship. So we'd seen a bunch of different things, we'd done a bunch of different things, and we were starting to really understand the difference. And David just came up with these 18 bullet points. They're not particularly grammatically correct, as every time I would open up this document, Grammarly, would put little red lines under all the things that weren't quite right. And I'd have to say, dismiss, dismiss, dismiss. Go away. I don't want this. But there were 18 of them. And one day I realized that I made my own synaptic connection of that. And I'm like, that's cool. But I'm not going to say that I'm going to let people Figure that out. But you're the first one that got that.

So I win the contest, you win.

The contest, you win the chai. I'm gonna make a Guy Kawasaki chai.

You can tack it to your door every time you go outside.

It has touched my little.

Kai.

I was gonna say Guy Kawasaki. Hi.

Forget the mezuzah tap, the hai.

It's Monday morning when we're doing this. The rest of this week, it'd be whatever it is. That made my week.

Maybe I should change my name to Kai Kawasaki.

I like that. But then people would think you're high all the time, and that would just be confusing as somebody from Colorado, and that's where I am. Everybody in Colorado is always high.

Rocky Mountain high. Yeah. All right, so now let's. Let's actually have some content in this episode of Remarkable.

You didn't realize that you'd have to take the first 15 minutes and just cut it out.

I read someplace that one of the high correlations of successful podcasts is there's not a lot of bullshit banter at the start. They get right into it. So that's why my podcast isn't that popular. But okay, so first of all, I got a question. And, like, what is the difference between give first versus pay it forward?

One word, non transactional. So if you think about pay it forward, which is a cousin of give first, you feel obligated to pay it forward. Somebody says, I'm going to pay it forward because somebody once paid it forward for me. I'm going to do this because somebody once did that. Give first is that you're willing to put energy into a system without knowing what you're going to get back. It's not altruism. You expect to get something back. You just don't know when, from whom, over what time period, in what form, or what consideration. So the sort of foundational difference between the two is that pay it forward has this transactional component. I'm doing this out of obligation. I'm doing this because somebody once did it for me. Give first is just a philosophy. It's a way of being. It's a way that you approach things. And it's important to recognize the difference, I like to say, in this concept between religion and philosophy. Give first is a philosophy. Religions are. If you do this and you do all these good things, theoretically, some good thing will happen to you. That's kind of the principle of most religious traditions. Now, it's not how a lot of people behave in a religious context. But take the religious Tradition, principle. And so this idea that you're obligated to do good things so that then some good thing will happen to you. In a philosophy, you don't have rules, not a set of rules that you follow. You just incorporate the ideas or the concepts of the philosophy into the way that you are. And so for me, I've approached Give first as a philosophy. You don't do it all the time. You don't have to do everything about it. You're not trying to get a bunch of check marks or, hey, you did a good job. It's just a way of being.

So are you saying that if you have the give first philosophy, it's not transactional in the sense that who you're giving it to, you don't expect anything back, but if you have a gift Give first philosophy, are you expecting that sometime, some way totally unrelated, the karma will come back to you, or you don't even expect that generalized random thing.

You got it. And karma is a good word for it. And a lot of people have said, oh, that sounds like karma. And I'm like, okay, that's fine. You can call karma. I've tried to flesh it out a little bit more. Karma is like a label people put on things that they don't think that hard about most of the time. And here I was trying to get people to think a little bit harder about it. But that's why I say very deliberately, this philosophy is not altruism. Right? But you have no idea what's going to come back to you in the future. And the interesting thing about that is that you're willing to put energy into things where that energy has substance. And if all you did was give first and you didn't ever expect to have anything come back to you, you'd eventually be like, why am I doing this? What's the value of take a really altruistic type of being. It's not monkish. You're not sacrificing, you're not behaving in a way that's completely unselfish. And in fact, in a lot of ways, the energy that you would put into systems or people can be selfish. It can be things that you think could benefit you in the future, but you just don't know how it's going to benefit you.

So, Brad, how can one tell if a person will be a good mentor?

It's very difficult. And it's very difficult for two reasons. One, in advance of engaging with someone as a mentor, if you're viewing yourself as a mentee you have no idea how that other person is going to react to you. Again, the a priori definition. It's hard now reputationally, seeing how somebody engages with other people that can be helpful. But really, the magic is the second part of this, which is the magic trick of mentorship is when mentorship becomes a peer relationship. The powerful, best, most amazing mentors learn as much from the mentee as the mentee learns from the mentor. And this doesn't take a long time to unfold. This can happen pretty quickly. So as an example, I'm in a mentor situation. Often a lot of people think of me as a mentor or I play a mentorship role in whatever the context is for me. In every interaction, I try to learn something, and I find myself as a mentor often in that first or second interaction I'm having with somebody, learning as much from them as they're learning from me. And that magic trick is what causes people to continue to mentor someone. It's not this selfless. Oh, I just feel like I should. That's okay. There's nothing wrong with that, but it's kind of uninspiring. It gets boring. You know, the meat of it isn't really there. And especially as we get older, I'm about to turn 60, to hit 60 and think, oh, I know everything and I've got all the answers and I know exactly what's going on. That's just full of shit. And somebody who is 20 or 25 or 30 or 35 or 40, somebody who's 15, I have so much to learn from that person by the experience that they're having. That's different than me, right? I happen to be a technology guy. I've been writing software and involved in software and technology since I was a teenager, engaging with people who have nothing to do with technology but use it every day. In terms of what, their businesses, I have a ton to learn from them. I'm a white guy.

I'm Jewish.

I was born in Arkansas. As you pointed out, I grew up in Dallas, Texas. The number of people that are not white guys that grew up in Dallas, Texas, that I can learn from is many. And it's not just lived experiences. It's all the different things that the person's thinking about and dealing with and interacting with and how that integrates into the way I think about things. Looking for that character in a mentor, I think is what makes a great mentor, where the mentor also believes that they can learn.

So basically, you're talking about humility, right?

Humility is a Part of it. But I don't think it has to be that fundamentally. There's no arrogance in a mentor. Just to take the opposite word of humility. I mean, successful people, even if they're not jerks about it, we all have egos. And I wander around, I get all my news now from south park. And so I love characters on South Park. And so my, my ego for me is like a little guy on my shoulder that's whispering in my ear and I sort of say, go away, leave me alone, like bothering me. But it comes back. We all have it. But that's okay. That's part of being a human being. And so I don't think it's that you have to fundamentally have humility that is overwhelming of your personality, but you have to have humility. You have to have some. You have to recognize that you can learn from anyone, you can learn from any context, and that you actually have to be kind of curious about it. It has to be interesting to you. Because there's a lot of people who say they like to learn. There's a lot of people who roll out some cliche again, like first principles or blah, blah. I'm always constantly digging, whatever, okay? There are very few people who are really inquisitive. And if you look at again, long arcs of philosophical tradition and you go back in our species, not tens of years, hundreds of years, thousands of years, and you look for people who are actually thinking about how does the human condition work, what makes us what we are, what makes us better. And I say better with kind of a question mark at the end of it. Because I'm not going to be arrogant enough to define what it means to be better, even though I have a value system of my own and I have opinions about what better means. But there's 8 million people with different versions of that opinion. And so to have somebody say this is the way we should be and give first mentality means blah, blah, blah. And therefore in a give first philosophy, you must, I mean, like, those are the exact opposites of what it means to be a good mentor.

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You're listening to Remarkable People with Guy Kawasaki.

If I'm some 19 year old undergraduate at a school and I'm seeking a mentor from the outside looking in, how can I tell if Brad is a good mentor or Guy is a good mentor or V not is a good mentor or Mark is a good mentor, what am I looking for in a mentor?

A couple things. One, to summarize that last bit, you're looking for a mentor who's interested in you and interested in learning in their interaction with you, which again is hard to know in advance. Next. And you can get a lot from people's reputation, so you can see how they've engaged with other people. And there's not a singular archetype of mentor that works. So you're not in this thing where you're looking for, oh, I need a mentor that has these five characteristics. What you're looking for is someone that you feel like you can relate to as a mentee, somebody who you respect, somebody who you look up to, somebody who you want to engage with. But again, if you go to this magic trick of the mentor mentee relationship becoming a peer relationship as a mentee, you're looking for someone who you hope to have a long relationship with, where you're both learning from each other, rather than someone who you're just trying to get something from in that moment. Again, back to this non transactional idea. If you're like, okay, that person is going to be a good mentor because they're going to help me get introduced to so and so, or they're going to help me figure out how to do such and such. That's helpful, but that's not really the mentor arc. The mentor arc is 30 years from now. You're still engaged with each other, you're still talking to each other, you're still learning from each other, you're not necessarily in business together, you're not necessarily working on things together, but you still have a relationship. And I think at 19 or 25, as you're deep into figuring out how to navigate your way through business, technology, life, whatever, it's sometimes hard to think forward that way. But at our age, it's easy to look backward that way and say, you know, I think about people that I am still learning from 40 years later. I think about people who have, unfortunately who have passed away, who were incredible mentors to me, who at some period of time when I was in my 30s and some had long relationships with them by that point decade or whatever, would say things to me like, brad, I'm learning more from you than you're learning for me. And I'd say that's nonsense. And they'd say, no, no, no. So it's developing a substantive relationship is what you're looking for in that mentor. But the blunt question, how do you find that person? You have to just try. You show up, you engage with people and you're going to have multiple people and you're going to have some people who, oh, it'd be so great if famous Person X was my mentor. But Famous Person X has no interest in being a mentor. And Famous Person X has no interest in really engaging with you, but they'll help you with. That's different than less famous person. Why? Who all of a sudden is really substantively engaged with me around something that is now starting to have a long term arc. That's a great mentor, Brad.

As I think about it, I'm getting very nostalgic about Al Eisenstadt. Al Eisenstadt was my mentor. He was my mentor at Apple. Seriously, he really helped me at Apple.

That's great.

Okay, so now let's flip the question and the question is now you are Al Eisenstadt or Bradfield and all these people are asking you to mentor them. So how do you decide who is worth mentoring?

I think there's a couple of different ways to approach this question. And I'll describe how I approached it, which is not the only way to approach it. I approached it over a long period of time with a mentality that I would refer to as default. Yes. And essentially I would engage with anyone who reached out to me. And again, my little ego sitting on my shoulder, I'm sure was telling me that it was part of, you know, part of the way you are, Brad, is that you respond to all your emails and isn't that a good thing? And so it fed some element of my ego to do that, to be responsive. But I just decided that part of the way I was going to be was just responsive to anyone. And one of the challenges with being responsive to anyone, and I'll give a discreet example, there was a period of time in I don't remember the 2003 or 2004. I've been living in Colorado for about a decade. I was very well known in Boulder and Denver, but I was also investing nationally and well known as a writer and a VC and an investor nationally. And anybody who was coming through Colorado for any reason, I would get an email, can we get together for coffee? And it would be, you know, I'm coming to my daughter's college, friends, roommates, sisters, cousins wedding. Do you have time Monday morning for a cup of coffee? And if all I ever did was say yes to those things, all I'd ever do is have coffee and go to the bathroom. Like, I get nothing done. And so I hit the point where I had to figure out how to create some boundaries. And so I came up with different ways to do that. Part of being accessible was I decided I would be accessible by email. And so I'm an infinite emailer, but not accessible infinitely in person. I'm still very accessible for a long time in person. I started to put up boundaries and I started to figure out how to do it. And eventually I came up with a tool, which is when somebody would email me, hey, can we get together for a cup of coffee on Monday morning or Tuesday morning or Monday afternoon or whenever? I would have a very simple response where I would give the person an assignment. And a lot of it today is, can we do a zoom call? Can we do a call? And, you know, it's easier to say yes to a call than a cup of coffee in some ways, but it's worse because you end up spending your whole time, your whole life, sitting in front of a video conference. And so I give the person an assignment and I kind of respond, usually to force them to tell me why they want to spend time. But I don't say it that way. I say it in a clever, simpler way. I try to be responsive to whatever their email is. Sometimes, if I know who it is, I'll go down the path of what they're doing. If I don't know who it is, I'll look them up on the web. You know, they make this thing called the web. You type into a little box very quickly. The little box brings back a bunch of information about the other person so you can very quickly learn about it. You have to be a little careful which box you type into, because sometimes the box will tell you a bunch of nonsense about the person. Be careful where you type. I asked the person a question, and often that turns into a more substantive email response from them. Which then shifts the conversation from do you want to get together for coffee? To an actual interaction. And then that interaction becomes an email interaction. And I'll stay on the email interaction. I kind of ignore the request for a cup of coffee or request for a zoom conference, because now we're interacting. We don't need to have a coffee or zoom conference. You were just saying that because you wanted to interact with me. So I use this approach of being responsive to anyone, not having any idea where things are going to go. Interestingly, about 50% of the people who reach out to me this way, after I respond to them, they don't respond. I never hear from them again. I have no idea why. I view it as a blessing. Right. Because people are constantly reaching out to want to someone that. If you're busy, I'm sure you have this phenomena. You're in the receiving end of it. You get this endless reach out from people who want to engage. They don't really know why they want to engage. Maybe they want to network or they think that you can do something for them. But when they disappear, okay, so 50% go away, 25%, and these are rough numbers. Not exactly. 25% respond. And now I'm having an email engagement with them. 25% of them take a little time to respond and then come back and say, you know, we don't need to get together. Actually, your question was very interesting to me. It made me think about this, this, this, and this. And so then I went and did this, that, that, and this and that. Well, that's the person I actually want to engage with. That's a person who does stuff. So that would be an example, another example of how you deal with it. Something I did for a while, which is I realized I did want to get together with some set of people. I found that stimulating. It was a good way for me to learn. And so I created this thing that I did once a month for about 10 years called random Day. And so once a month, for a decade, I'd get together with anyone who wanted to get together with me, and I'd do it for 15 minutes. I would usually have 10 to 20 meetings in a day. I couldn't do more than 20. 20 fried me. But somewhere between 10 and 20, I often did it in a public place so that it wasn't. You're, like, lining up outside my office to have a meeting with the king or whatever it was. I'm in a coffee shop and there's people milling around and, oh, yeah, I'm Waiting for my whatever. And people would know. And so then people would show up early because they knew that I was in the coffee shop and I'd sit down and it used to be I used a kitchen time. Remember those kitchen timers when we were little kids that you had to turn and you had to turn and pass some number so that it's kind of like on the pool thing. You have to turn it past 10 so it turns on, turn it to 15, and when it finishes, it would go, ring, ring, ring, ring, ring. And that was the end of the meeting. Eventually, I started using my iPhone because, you know, it has this thing on it called a timer.

And when it ends, you just goodbye, Goodbye.

I'd say, look, the next 15 minutes belongs to you. Next 15 minutes of my life belongs to you. Go. And you know, the timer would go off and people would be like talking. I'd say, look, the timer went off. It's 15 minutes are up. It's time for the next person. And I'd be polite about it. And every now and then somebody be like, blah, blah, blah. I say, look, you got 15 more seconds. Finish up. Time to go. And the next person that was waiting would hear that and they'd be like, oh, I really only got 15 minutes. Most people were respectful of the 15 minutes. And I would do this. And eventually, after maybe a year or two of doing this, I realized I was getting a little bored. And I realized I'm like, if I'm going to do this, I. Okay, I have a goal. I have a goal. And I ended up having two goals for every 15 minute session. Goal number one was I wanted to learn one thing new, just one thing. And what's remarkable, it's trivial to learn one new thing in 15 minutes from someone you've never met before. If your goal is to learn one new thing, it's actually quite easy. Like you, you, I just reframe the 15 minutes is I'm going to learn something. The other was I'm going to do one thing for this person that's helpful to them. And a lot of times I'd learn more than one thing. And a lot of times I'd do more than one thing that was helpful. But in every meeting from that point forward, one of those two things happened. And that became a pretty essential part of this mentorship loop for me, which was this idea of, if I'm going to spend time on this, I want to learn and I want to be helpful. It's kind of that simple.

Well, Brad, I will tell you how much better a person you are than me, because I get a lot of requests to review people's pitch as if I got nothing better to do. And that takes 60 seconds. It takes a long time. So I came up with this practice that I will review your pitch, I will mark it up, I will send it back to you. I'll even have a phone call with you. But you have to donate $500 to various organizations. The money wasn't coming to me. It was going to somebody that needed the money, the hockey club or whatever. And to my utter amazement, I think 90% of the people went away that they didn't value my time at $500. Now, maybe they didn't have the $500, you know, blah, blah, blah. But it was very interesting that if it was free, I'd take up all your time, guy. But if I have to pay 500, you're not worth it.

Well, that's a, that's a. That's a deep insight. And I think it's very similar to the experience I had, which is you don't have to put a particularly high barrier on things. Yeah. But you do have to create boundaries. And if you don't create boundaries, as especially somebody who is creative and doing their own thing in the world, all your available time will be absorbed by other people. The boundary is not a boundary that's so high that prevents people from engaging with you. I'll use the word gatekeeper. Think of all the rich and famous people in the world who have gatekeepers, and their gatekeepers have gatekeepers. And the gatekeepers have gatekeepers who have gatekeepers. And if you're part of the inner circle or you know how to navigate the gatekeepers, or you have some. Whatever, or you're just so persistent, you can maybe get through to the person. I've never had gatekeepers. I don't want gatekeepers. I find that to be inhibiting of randomness. That sometimes is awesome. And in the context of that, though, you do have to create boundaries, because if you don't create boundaries, you don't understand it. You'll have no time for it. Interestingly, I love, by the way, your boundary that you set with the pitches. There was a period of time, and you know this, but there's a period of time in entrepreneurship, probably for about five years, where after you'd written about the 10 slide approach to pitch, I think the number of times I heard your name and I heard that and I saw pitches that used your format after you'd done some stuff around that, you nailed it. You hit a theme that everybody's like, okay, this is how to do it well. But your comment is a really simple one. You could have said, look, you buy my book, read my book, and then I'll look at your pitch. The problem is that that wasn't quite enough of a boundary for a couple of reasons. One, people might buy your book, but then they're going to read the book, they're going to pretend they wrote the book, they're going to turn the pages, and then they're going to say, okay, I want the real work. But by saying, hey, look, if you're serious about it, my time has some value, but I don't need the money, I don't want the money. Help something else. And then essentially you're donating your time right to that. I love that. That's a very powerful approach that has resonated. It has resonance with my value system, which is you do have to create boundaries so that you don't think it absorbed by the infinite number of things at once your time that you know the other person isn't actually taking you seriously.

Yeah, well, God bless you, Brad. It's actually donate to play. It's not pay to play, it's donate to play.

I love it. I love it. I'll use that in the future somewhere. And. And people say, People say to me, will you come do this thing? And I say, you know, here, all I need is this. And 50 again, 50% of the people, if you say to them, you know what, I'll do your thing. No, I don't need a speaking thing. No, I don't need a this. No, I don't need a that. But you know what? If you'll take the speaking fee and you'll donate it to this organization, I'll do your thing. You could imagine that probably still they would do that. But for the people that say, well, I don't have a speaking fee, I can't donate it. Okay. Yeah.

Okay. That's interesting.

It's interesting. I learned there. I learned two things today. Number one, I learned that, you know what the number 18 means in Hebrew. And two, I just came up with a new boundary technique. Thank you.

You mentioned this thing about, well, I could tell people they have to read my book before and, you know, blah, blah, blah, as the boundary. And I'll tell you a funny thing. So constantly, Brad, constantly I meet with people and they said, oh, guy, I read your book. I understand. 10, 20, 20, 30. I absolutely believe in all your principles and Then they open up a PowerPoint.

Pitch, 37 slides and it has 37.

Slides with six point font.

Like what you just told me.

You read my book and you believe in 10, 20, 30, and you have 60, 50, 90, like what is wrong with you? But anyway, okay, so now you have obviously met with thousands of entrepreneurs. And actually Brad, I'll tell you something. I believe that I lost my hearing because I listened to so many shady pitches. But that's another story. So you better be careful about your hearing, Brad. But anyway, so I want to tap into the Bradfield pattern recognition. Like what patterns have you figured out are indicative of a good entrepreneur?

So pattern matching is an interesting phrase that I really don't like. Okay. And I'll, and I'll explain why. There's a bunch of phrases that have become Silicon Valley phrases or entrepreneurial phrases that I don't like. One of them, for example, would be that I really despise is meritocracy. Whenever somebody says it's a meritocracy, my first response is that's bullshit.

Why is that?

Well, you know, everybody has the same ability. You know, all they have to do is work hard and they can accomplish anything. And like, ah, time out.

Like, especially if you're a white male.

Yeah. So I'm like, no, come on. And yet people continue to insist it's a meritocracy. I'm like, no, not, not, not in my experience. Another phrase which I hear VCS use all the time, that just is a great tell when a VC says it, that the VC is full of is I'm value added. And I like to say for me, the tell is when somebody has to qualify what they are. I'm a great investor. I'm a whatever, you don't need to qualify. I'm an investor. I invest. Like you, you, you guy get to decide whether I'm great or not. Not me. And whatever the qualifier is, I'm a authentic speaker. I'm open.

How about I'm open and transparent?

I'm open and transparent. It's like, yeah, okay, you're just telling me that you don't listen to anybo. And so there's a bunch of stuff like that. And I'm sure I have some verbal tics also. Everybody does. But there's these things. So pattern matching is a phrase for me that sort of fits in that category because what it really does is it says I'm not going to think critically about this thing that's that I'm encountering. I'm looking for A thing. It worked for me once before, it's going to work for me again. It doesn't mean that the patterns don't apply. They absolutely apply. And some things that worked once can work again. And I like to believe that they work again until they don't work anymore. And I've had that experience where, like, I did something, I'm like, well, this worked over here. And then I tried again and have a massive failure. And I'm like, ugh. I didn't really actually learn the real thing from the thing that worked. I learned the wrong thing from the thing that worked. And you see that happen over and over again, especially in the world of investing. But you also see it with founders, and you see it, by the way, with experienced CEOs that get hired. This thing worked for me at this company over here, so I'm going to do it again. And what they don't realize is the thing that worked for them at that other company isn't fundamentally what's needed at this new company. So for me, I've tried to, as a founder and an investor, do things that rhymed with things that worked before. For me, I view entrepreneurship as an endless series of experiments. You have a hypothesis, you run an experiment. Most of the experiments fail. You learn from the experiment, create a new hypothesis, run a new experiment, and when the experiment works, you do a lot more of it. But you have to keep testing the hypothesis even when the experiment's working, because over time, things change. The environment changes, the landscape changes. The exogenous factors that have been helping you, you know, things completely out of your control change. People change. So I like to think that the patterns are useful as guides, but not as matches. They're useful as stimuli to test against, not as matches. And I also think maybe it's a little bit get older. I'm not a believer that I'm going to live forever. I'm pretty sure I'll hit a point. I don't know what the age is, but 90 years old or whatever, I'll be sick and tired of the human species and that'll have had enough.

I can tell you I reached that at 71:1. So I'm an overachiever.

The AI might exterminate me well before that. By the way, AIs, my name is Brad. My last name is Feld. I'm nice. I like you. I am a good pet. I will be. I'll be a great pet. I am not threatening in any way, shape or form, if you're listening, but so that's why I struggle with pattern matching for me. But when I think about what are some essential characteristics to me that are interesting around a founder, that makes for a great founder. There's three things that I come back to over and over again. The first is, was this person put on planet Earth to work on this problem right now?

That's a high bar, man.

No, but it doesn't have to be for the rest of their life. It's just right now. And I used to use the word obsessed. I used to say, is this person obsessed about the problem they're working on and obsessed. For some people, it's got positive and negative connotations. A lot of people get confused about what obsessed actually means in a healthy way versus an unhealthy way. So then I started saying, were you put on this planet to work on this problem now? And it's interesting. It's, it's, it is a high bar, but not really. Like, I've met, and I'm sure you have too met so many founders that were like, I just want to be a founder or I just want to make a lot of money or I want to change the world. What?

Or I got three different ideas. Which do you like?

That's right. It's like, I'm not looking for that. I'm looking for this is the thing. This is the thing. And it's not passion. Because I learned pretty quickly that extroverts are outstanding at faking being passionate about. If you're an extrovert, you can fake passion about anything. And if you're an introvert, it's very hard to be passionate. A lot of times when you're not natural at selling or you're not natural at marketing yourself, or you're not natural at explaining an idea that you might really deeply understand, well, that person might have been put on planet Earth to do it. They just don't have the energy or the style or they haven't figured out a shtick around it. So that's piece one. Second, do I have an affinity for the thing the founders are working on? I don't have to be a daily user of it, but I have to care. And the reason I have to care as an investor is that every company I've ever been involved in has had a near death experience. And many have died. Many have just plain out died. But every successful one has had a near death experience. At least one. And when it's going really poorly or when you have something, everything was going great and then something happened, whether it was self inflicted or external, that really shook the potential of the business or really put the business on a downward spiral that you had to survive. If I as an investor didn't care about the business, didn't have affinity for it, it was really hard to keep my head in it, really hard to do the hard work to support the founder, the leader, to get through whatever that miserable time was. And then the last is that the founders have to want me to be a partner with them as much as I want to be a partner with them. The founders have to want me in their company as much as I want to be in the company. If I just really want to be in the company and all the founders look at me and they just see money or they just see, you know what, okay, whatever, that's fine. That could be a good investment. I'm not saying that's a bad investment, but I'm not that interested in engaging with that because even my most successful companies have taken a very long time and they've been really hard. And the overnight success that takes a decade to even turn into something that resembles a success. Well, I'm going to be spending a lot of time with you and you're going to be spending a lot of time with me. If you don't want me really in your company and just want me as an investor, the money, that's not the kind of founder I want to be working with. That's a transactional founder versus a non transactional founder. Somebody who's going to value the other parts of the person. Up next on Remarkable People Ineffective mentorship is the person says to you, we're out of money in a month. And the mentor immediately starts telling you what to do. But this is the problem. The problem's not that you're out of money in a month. The problem is something deeper than that. And if I'm a mentor, I want to get to the root cause of it with you and I want to understand with you what's actually going on so that in our engagement I can be helpful to you.

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Become a little more remarkable with each episode of Remarkable People. It's found on Apple podcasts or wherever you listen to your favorite shows. Welcome back to Remarkable People with Guy Kawasaki. So now let's say you found this person. Things are going along, you know, pretty well, and at some point you come to something and you just believe that the founder is absolutely, positively dead wrong. And the founder thinks he's absolutely or she's absolutely, positively right. What do you do?

Well, a couple of different things. One, I have very, let me put a qualifier. I have very infrequently run into a situation that polarized. And I feel like that level of polarization generally comes from two parties who are unable to think critically about things and are unable to recognize that they might not be right. Now, I've definitely worked with founders who have anchored absolutely on this is the way to do it. And so I then am someone who says, all right, I could be wrong. I'm not going to anchor on this is the absolute. You're absolutely incorrect. Some of the reason for that is in some of those situations where I've really felt like the founder was incorrect, they have been right and I have been wrong. And a starting point for me for it is this recognition that sometimes when I really strongly believe something, I have been wrong. The next is I am okay with having the hypothesis tested by running the actual experiment. So the founder really believes strongly in something. All right, let's try it. And the only thing I'm not comfortable with is when it's not working to not acknowledge that it's not working. The leader who says it's not working yet, but it's going to work. It's still not working, but it's going to work. It's still not working and we're about to fail completely as a business, but it's going to Work. Okay, it didn't work and we failed completely. Well, then, okay, you're done. So there's like a level of, okay, well, let's test it. Now the other side of that, which is very interesting, is there have been situations with a founder or a leader, I should probably say leader versus founder, where I fundamentally disagree with their approach to how they deal with people. Deal with the problem, deal with whatever. And I have an option which is I can opt out. And I can opt out by saying, you know what? I'm gonna get off your board. You want to run the business a certain way, I just don't agree with that value system. I don't want to be part of this. That hasn't happened very much in my life. It's happened once or twice. There's also been situations. The, the opposite is true. As a board member and an investor in a company, I tend to have one framing for myself, which is as long as I support the person leading the company, I work for her. My job is to help her be successful. As, as a board member and investor, my job is to help her be successful. If at some point I get to a place where I don't support her anymore, my job is to do something about that, which is to start with trying to get back to the place where I support her. And I do that by being very direct, by talking clearly, by trying to engage with the person, by explaining why they've lost my support and, or what I'm struggling with. And that occasionally will lead to one of two things. The tool I have as an investor is not to fire the person. The board has that tool. So I'm a participant in a team that can explore that. And there are some boards that, that's not what the board wants to do. I think we need to replace the leader. And the board's like, nope, we disagree with you. I can either can say, okay, I changed my mind, I'm going to keep supporting the person, or I can exit the board, or I can try to influence the board and the collective team to make a replacement. But I, I, I say that in a long winded way to put the emphasis on this idea that, that it's not that I'm trying to agree with the person. I actually think there's a lot of healthiness in leadership and disagreement. I think that the value to your question when you're at polar ends of the spectrum is that one of those two people needs to be able to say, all right, I need to think about your strong feeling in a Different way. I've tried to influence what your thinking is. I've tried to make these from my frame of reference. Strong, thoughtful, rational, authentic, transparent value added comments. And you still really feel strongly about this? All right, let's give it a try.

My last question for you, which I found very intriguing in your book, is this technique of five whys. So can you please explain this to our audience? Because I thought it's really, really interesting and helpful. Helpful?

I didn't come up with the five whys the same way you came up with 10, 20, 30, but I wish I had.

Well, you know, one thing I learned from Steve Jobs, Brad, is, you know, you gotta know what to steal.

Just label it yours. Yeah, that's right. Five whys. Five whys is a technique I've been using for a long time, and I don't remember where I first encountered it anymore. A long time ago, I realized that when somebody says what their problem is, it's very rarely the problem. Often when somebody asserts a problem, they don't know what the root cause of the problem is yet. They haven't gotten to it. They're just asserting what their pain is. There was a guy in my very first company. We were having trouble getting any customers, and I went to a sales seminar. I remember the guy's name because it made such an impression on him. He's a younger guy. His name was Jeffrey Lance. I don't know if Jeffrey Lance still exists on planet Earth. We were living in Boston. He had some seminar in some place near Boston harbor. And I'm like, okay, I'll pay my $500 or whatever, $100 to go to this seminar because we're just having trouble selling. And I'm like, I need to figure this out. And I thought it was going to be like hundreds of people. It's like six. And he has a big book that's self published, eight and a half by 11 hands. And it was a day. And the thing I took away from that was that the problem that most people have when they're selling is they don't understand the customer's pain. And today in entrepreneurship, it's is your product, is it a vitamin or is it a painkiller? Does it really solve a fundamental problem? Is it, you know, the inverse of that is what five whys gets you to. So this notion, what Jeffrey taught me, was if you're gonna sell, find out what the person's pain is and solve their pain. That's what you're doing as a salesperson. Solution selling. Emerge from that sort of thing, five whys are. Somebody says, here's my problem. If all you say is why, first thing they'll do is look at you. You say, no. No, seriously, why? Why is that? Why is that a problem? And they'll go, blah, blah, blah, blah. And that's interesting. You get to, like, another level. You say, why? They look at you and you say, no, but why that? And you keep going. And usually by third or fourth, sometimes fifth time, that you ask why? And you don't have to be that much of. I'm being dramatic in terms of it. The why can have a little bit of substance behind it, but you're getting deeper into the problem. And so somebody says, we're going to run out of money in a month. That's my problem. We're going to run out of money. A month. Why? We only have a month's worth of money in the bank account. Why? Because we've not been able to get our investors to give us any more money. Why? Because our investors are jerks. Why? Because that's not the reason. And eventually you get to. Because we have a product that nobody's buying and nobody believes in it. And as founders, we're not communicating very well, and we just popped on our investors, you know, whatever, Right? But you keep trying to find the root cause of the problem, and you can apply this to anything. My wife's name is Amy. Amy is angry at me this morning. Why? You know, like, off you go. Because she's just in a bad mood. Why? Because she's just mean. Why? But so you can apply it anywhere you want. In terms of. The key is, if you're really trying to solve a problem, you need to get to the root cause of the problem. What is the actual thing you're trying to solve? And this is effective mentorship versus ineffective mentorship. Ineffective mentorship is the person says to you, we're out of money in a month. And the mentor immediately starts telling you what to do. But that's not the problem. The problem's not that you're out of money in a month. The problem is something deeper than that. And if I'm a mentor, I want to get to the root cause of it with you, and I want to understand with you what's actually going on so that in our engagement, I can be helpful to you. And as a founder, you could say, maybe you could say, I'm out of money in three months. If you. A month is dramatic. I'm out of money. Money in three months, or money out of money in six months. And I'm nervous about that. And you went to five mentors and just said, I'm out of money in six months. And the mentor says, how can I help you today, guy? Guy says, I'm out of money in six months. You're going to get five totally different, probably mostly useless responses. Unless one of those mentors does some version of asking you why. To understand what's at the root cause of your fear, anxiety, issue, problem, challenge.

I love that. I love that section. One thing that I learned reading your book, Brad, is I suck as a mentor. My God, I really do.

That was not my goal with the book. My goal was not to make people feel like they suck. It was to give you some tools to be more effective.

Okay, let me word it differently. Reading your book is going to enable me to be a better mentor.

That's awesome. Fabulous. I love it. If I believed in book blurbs, I should have called you up and I said, I should have sent you an email, Guy, will you blurb my book? And you would have responded with the. If you knew any better, you would have gone and said, Brad Feld once wrote a blog post, said, book blurbs suck and should die. And it's this one. Here's the post, and you respond to the person. And then it's amazing to me that still some percentage of people that I send that blog post to, it, they asked me to blur their book, say, yeah, but will you blurt my book? I really don't want to, but okay.

Brad felt it has been an absolute pleasure. And the way that this happened was Buzz, right as Buzz, bro. Yeah, Buzz made that.

Let's call him out, man. I saw Buzz in Seattle at an event for this book. I've known Buzz for a long time. Every time I see Buzz, he gets a huge hug. I get a huge hug. Just a delightful guy. And it was an event with Ben Gilbert.

Oh.

Who you had just had on your podcast. And Ben interviewed me at this event in Seattle, and Buzz said, brad, did you know Guy Kawasaki just had Ben on his podcast? And I said, yes, because I listened to Guy Kawasaki's podcast, and he said, well, I know Guy Kawasaki. And I looked at Ben, and Ben looked at me, and Ben said, I know Guy Kawasaki, too, because I was just on his podcast. And Buzz said, you would love Guy Kawasaki. I said, yes, Buzz, I love Guy Kawasaki. I don't know him, but he's amazing. And Buzz says, oh, you have to meet him. And that was. That was. It was a great it was a great moment in front of about 100 people.

Buzz is my only friend who uses Windows.

He is.

That's how much I like it.

All right, thank you, guys.

This was a blast.

I laughed.

Thank you. Thank you, Brad. Thank you, Buzz out there. I know you're gonna hear this episode. And let me thank the rest of the Remarkable People team, which is, of course, Madison Kner, Tessa Kner, there's Jeff C. Co producer, and there's also Shannon Hernandez. So we're just a bunch of crazy people who want to help others be remarkable. Brad. This is remarkable people.