How Founders Self Sabotage Dave Blakely On Truth Pressure And Leading Without Losing Yourself

TITLE: How Founders Self-Sabotage: Dave Blakely on Truth, Pressure, and Leading Without Losing Yourself CHANNEL: Not Another Podcast with Brennan Pothetes DATE: 2025-12-09 ---TRANSCRIPT--- The scarcest resource in the business community today isn’t capital, despite what some people will tell you. It’s attention. The wrong wrong way to get people’s attention is to yell successively more loudly and make more and more ridiculous claims that you’re going to be unable to substantiate. CEOs do it all the time. It’s a mistake. It bites him in the butt. Stop doing it.

Meet Dave Blakeley. With 12 years spent growing ventures and supporting founders, now executive adviser at Infinity Constellation, Eric Shinseki, an army general, once said, “I don’t know the sure recipe for success, but I do know the recipe for failure. Try to please everyone.” Being excessively non-confrontational is paradoxically poisonous and destructive. Trying to avoid hurting people’s feelings and trying to avoid being destructive is destructive. I had a good mentor tell me, “You chose all this as a CEO. Like, you chose every aspect of the situation. So, like, why are you frustrated?” Right? Not only did you choose it, you worked really hard to put yourself in a situation where you’re miserable. Yeah. Everything on Twitter is like, “Dave, don’t build a board.” Like, “Don’t build a board.” Like, why would you want that? Like, you’re the founder. You’re in control. Yeah. Look, this is part of a show of raw raw arrogance coupled with certain cognitive distortions that you see on a lot of founders ultimately to the detriment of the uh of the company. Something I look for very very carefully is I want people to be self-aware about balancing internal versus external validation. If I’m working with a young founder of a startup, one of the things I ask is Well, thank you for coming on my podcast. Great to be here. How you doing? I’m doing good. Welcome back to the Bay. I like being here in a sunny San Francisco. Of course you do. 81°. No humidity. No humidity. No humidity. Yeah. Unlike New York City, which is just humid until fall and then it becomes winter. If you don’t mind, I’d love to like open with a little story and then ask you a question. Absolutely. Bring it on. So, I think like one of the hardest things I found over the years building companies is that, you know, I used to build companies for so much external validation. Like I really loved being the founder, I really loved um you know, like when I’d post sales up in a big month or I’d hire a great person or the the business was doing really well or I’d close a big round and then when the business was not doing well, it like wouldn’t wouldn’t do good. And uh you know for one of my businesses I was the main doing founder led sales up to a million dollars and it hit a point where I like couldn’t get off the couch for a week because like I was so burned out from doing sales and then after that I ended up selling my company and my big lesson from that was you know I needed to minimize the external validation on both up and down and then that helped me build a better company. I guess like my question to you is like you know you’ve been this like prolific product builder for for many many years. Can you tell me a bit around um you know just like how you’ve seen founders lie to themselves or like edge themselves in the wrong direction? I’d love to hear your thoughts on that. I absolutely can. It’s a it’s a great it’s a great question because a lot of times when people like we us talk you end up talking about the sort of typical challenges that that startup founders face. You you hear about problems with founders uh getting not getting along well. You hear about problems with product market fit, value prop, you know, screwed up beta tests, whatever it is. And in fact, people lying to themselves and lying to the people around them is a chronic issue. It’s under reportported and I’m glad you brought it up. I think this is something that I have seen my whole career and it’s something I look for in particular as an independent board member um when I’m working with with teams of founders. Um it is the most natural human thing in the world to want validation. You you just acknowledged you want validation, right? Um, in particular, one of the things I love about Silicon Valley is you’ve got people in their early 20s in command of tens millions of dollars of investment money and they really want to be held in positive regard. I get it. They’re super self-conscious. There’s a level of insecurity. There’s a lack of confidence. Something I look for very, very carefully is I want people to be self-aware about balancing internal versus external validation. If I’m working with a young founder of a startup, one of the things I ask is, “Are you very concerned that your board of directors likes you or do you ask yourself, do I like them?” See, I started laughing right when you said that because my very first board of directors um like I had this amazing VC on the board and I like watched his content for years, right? And so then what ended up happening is like I would just defer and I was almost like deferring too much to the board. And I and I sort of like put myself in a hierarchy beneath the board. And I I was subservient to the board. And what I always tell all the founders that I advise or invest in is like this is your game to play. Don’t let anyone else tell you not to play your game. Is that kind of like what you’re getting at? I think that’s I think that’s very well put. Um it’s one thing to defer to a board. It’s even worse to subvert yourself and who you are in the face of a board. Yes. It’s another thing entirely for example for a founder to instead of um to to instead of saying do I like what my board is saying? Do I like what my investors are saying? It’s another thing entirely for a founder to say what can I say that they will like to change their cadence their images their accent you know the their the the the voice itself all with a view towards currying favor with the founders and probably probably the biggest one is you have to ask yourself am I desperately seeking their approval or am I in a position where I grant approval to them. Yes. where the them can be anyone from your co-founders to your investors to your board. And if you find that what you’re doing is subverting yourself in a way that you think pleases the people around you and you’re morphing into a different person depending on the context, you’re not being authentic to yourself. And look, I submit you’re not going to win. You’re not going to succeed. I love the the framing of you’re not being authentic to yourself. Yeah. I I’m a little more intense when I use this description. I say like the army soldiers lots of money to like convince themselves they’re already dead to like run at the machine gun nest and like that’s a little too dramatic startup for me but I like watch a lot of World War II documentaries and I like that’s sort of like the way I think about it is I’m my startup’s already failed my business is already or it’s already succeeded like either way that’s like done but I’m going to play the game my way and like you just have to be very authentic to yourself. So, like I’m going to steal that because that’s so good because it is it’s not about not caring or like you’re already dead like you’re some combat situation. It’s more like people back you because like you’re the authentic founder. Like it’s your game. They want to see you play that game. And I think like a bit of this that I want to sort of pry into is like well what what are the incentive structures that Silicon Valley and venture investing and founders set up to sort of like cause this mechanism and like you’ve seen a lot of it. Like what do you do you think that our system can be improved? Do you think that there’s like bad incentives that cause this? Because I’ve also seen boards completely defer to a hot founder and make like bad investor decisions. Like I think it goes both ways. I think even more than than circumstances that that that boards and that investors and founders set up, I think what you’ve got is two situations that are really really common that I tend to look for again as a board member. The first is a situation in which you’ve got a very focused founder of a of a company who is truly authentic to the vision of that company but is not herself or himself a CEO. So a CEO gets brought in and all of a sudden what you’ve got and you need to learn to to pick this up. All of a sudden what you’ve got when when for example the venture uh team brings in a new CEO that this individual then reports to as you know CTO or or COO or something like that. What you’ve got is a situation where someone is paring like a like a bird the um uh the uh the presentation materials, right? Speaking with great passion, right? Speaking really beautifully and dynamically and so on, but in their heart of hearts does not believe what they’re saying. And I’ve learned to watch for that very very carefully because people become expert posers and they even lie to themselves that they believe the mission that they’ve been handed as opposed to owning it. How do you detect that? Here’s one thing that I recommend. If you show me a founder who’s truly bought into the vision, I’ll show you someone who in everything in her or his life puts it in the context of the vision around their business. When you open up the Wall Street Journal, I’ll bet you that every single article you read, whether it’s about emerging technology or globalization, you know, or supply chain, you are relating in some way to infinity, and you’re contextualizing it in some way to infinity. And as such, what you’re doing is constantly adjusting and tuning your outward-f facing message. You need that. That’s a really strong indication um of of uh of someone who’s truly committed. And the second thing I’ll say that I look for is between someone who is truly committed and someone who just is putting on a show because a lot of people are very very good at this. Brennan is um inevitably building a business is really hard and you’re going to run into these big ugly demoralizing roadblocks. you know, um, an investor who you’re all excited about and you pitch to is going to slap you around and some important partner is going to walk away and you’re going to botch up the, you know, the pilot uh, work that you’re doing with some really critical client. This stuff happens. It’s happened to me many times. It’s happened to you. It’s going to continue to happen to both of us. How does somebody respond right if they’re clearly damaged and and and and set back and thrown for a loop by those inevitable roadblocks that happen? They don’t really believe in the vision because if they really believe in the vision, it will propel them on past those inevitable problems that they run into. Man, I I wish I had you in like a Delorean time machine talking to me about 5 years ago before I did my first startup because I founded um I founded an insurance company and I did it because I love small businesses out of uh like Main Street and I wanted to help them. Yeah. I couldn’t get off the couch and my wife who’s this awesome repeat founder, she goes, “Brennan, let’s say this thing gets super successful. Do you want to be a CEO of an insurance company?” And she’s like, and I was like, “Hell no.” And I was like, “Sure. Oh What do I do?” And I think like I had a founder in my angel portfolio hit that the other day. And I’m like in those situations, I’m always trying to like just coach and be a friend. But how do you so like if you’re a founder listening to this and you’re like I didn’t hit one or two or I like I don’t want to be CEO of an insurance company. What do I do? And like how do you advise those founders when and when they hit those situations? 90% of the challenge is acknowledging that you’ve made a right wrong choice and that you need to pivot. Right. Yeah. You had your wife, you had an you had an external point of view from someone who knows you very well challenging you and saying, “Look, you don’t really want to run an insurance company, do you?” Yeah. So, I think what we’ve got is 90% of the battle is the self insight. Um, here’s something that you might not remember saying to me, but you’ll believe you said it. We we had a situation um a year ago and and it kind of crept up on me for sure and and you mentioned you need to spend the time to quiet your mind and listen to that little voice inside you. Yeah. Um so I think on one hand you cannot be looking purely for external validation, external business frameworks, external ideas about where your market is going, right? You need to have confidence in your own informed intuition and in your own judgment. On the other hand, whether it’s your wife in your case or my private threeperson advisory board on the other, you need people that are honest and uncompromising and unscentimental with you and are going to be really, really straightforward in offering you advice. And I just can’t tell you how valuable that’s been for me. That’s what I would do if I were in my Delorean time machine is I’d go back and I’d get that earlier. And one tip I have for our listeners is this. Um, I have three people, one who focuses on HR, one in tech, and one in business that I come to when I have questions in those areas. It’s just precious to me. They’re my trusted adviserss. I don’t pay them. I’m never going to pay them. I think that puts things on the wrong footing. I advise our listeners to find a small group of trusted adviserss and pay it back in kind. So, one guy I know who’s an extremely uh skillful uh and intuitive uh HR professional who just based on my description of all kind of kinds of weird interpersonal situations I’ve run into has been has helped me through so much. He’s not much of a business guy. I coach him on the finances of his business, right? And so in relationships for these sort of quiet off camera, I think that’s a really valuable thing. Yeah. So it’s just really like getting a group of people to call call you on your BS. Exactly. Right. Exactly. So on the flip side, yes, they’ll call you on your BS. They can’t be overly impressed or overly enamored with you, right? They have to see you as just another guy. Yeah, if if they’re overly if they’re if they’re overly impressed with your title, you’re the chairman, you’re the CEO, you’re an EVP, whatever it is, you’re never going to get anything like the honest and uncompromising feedback that you need in order to succeed. Yeah, that’s such a good that’s such a good take because I think, you know, the the X or the Twitter take for founders is, you know, I always talk to them about building a really great board of adviserss and everything on Twitter is like, Dave, don’t build a board. Like, don’t build a board. like why would you want that? Like you’re the founder, you’re in control. And I think that’s such a huge miss. And like can you talk a bit around just why do you think that’s so prevalent to just say no board or like no like no board of advisor? Maybe like maybe there’s a distinction there between the two. Yeah. Um look, this is part of of a show of raw raw arrogance. um uh coupled with certain cognitive distortions that you see on a lot of founders, right? Um I’m a guy that believes in humility and tolerance and pluralism. I’m a guy that believes that winners in any game, including the business game, um uh have humility and admit that they don’t know all the answers. they have the self insight to um to know what they do well and the honesty with themselves to surround themselves with other complimentary people with other complimentary skills um to uh to help them out. Um so I think part of what you got is is a uh particularly a Silicon Valley culture, business culture generally that sort of rewards arrogance ultimately to the detriment of the uh of the company. Yeah. I think like one of the worst things a founder can be really good at or only good at is fundraising. Yeah. Because if like that’s your main vector, you’re always going to be able to raise a lot more money and then you’re never sitting there building the product. But alternatively, I was I was hanging out with one of my founder friends uh who’s like, you know, growth stage founder and he’s like I tell all my portfolio companies if your VC if you have like a down quarter and your VC isn’t trying to fire you Yeah. that you’re not you’re not important or like you’re not their top portfolio company. And I think that just creates like a really bad incentive because then it’s like why would I want to create a board of adviserss when it’s like I know I’m going to have like one stutter step and then I’m going to try to be fired. Like it’s just this weird it’s this really bad incentive structure. Sure. And if you find that your relationship with your board is the way people who don’t work in in in uh in startups think it is. They they watch Shark Tank and they think, “Oh, it’s like that.” If you find yourself in a Shark Tank position, you’ve signed on with the wrong investors and you’ve selected the wrong board members because it shouldn’t come to that unless you as a founder are having some really, really severe problems. Again, what I love seeing is someone who is really good at something, to your point, beyond fundraising. Without exception, the founders, especially the CEOs that I’ve seen who are incredibly good at what they do, they’ve got a superpower. They’re amazing strategists. They’re fantastic at operations. They’re amazing at marketing and sales. They’re technical geniuses. That’s thing one. And thing two, on the other hand, is they have the humility and the selfinsight to surround themselves with worldclass people to complement their weaknesses. How do you um as a as a founder, CEO, keep raising the bar um within your business and attracting world-class people without creating a really bad culture of like, oh, I’m just going to like layer and push people out. You need to walk the middle path there. Um, if you spend so long on the hiring process that you never made a bad hire, you’re never going to grow at any kind of appreciable rate. You will make bad hires, people will uh the company will outgrow certain people and you will need to let some people go. That is an unfortunate that’s fundamentally that’s if you believe in capitalism, you believe in that unfortunate necessity. Um, that’s that’s just that’s just how things are. What you don’t want to do is to um race ahead so quickly in such a sort of scattered way that um that uh that you that you leave everybody behind. So one of my early mentors, it’s a very simple thing to say, always used to say at any given time have a point of view. Have a point of view about where the market is going. Have a point of view about the dynamics and the and the levers of power both in your organization and in the market as a whole. communicate that to influence everyone around you and continue to stay on top of that and adjust it. That’s great. I mean, I think there’s also uh an issue with with folks around lacking confidence on a point of view. Sure. And you know for me I probably am on the wrong like the wrong end of that spectrum where I let’s say my early 20s had overconfidence on my points of view and I had to like learn to be more uh first principles and and approach things from from like okay like this could be something that changes my worldview right how do you as like a founder or builder of product um have that point of view but also like maintain first principles from your experience sure so I think that’s an incredibly important question and Here’s here’s why. Um, I think point of view increasingly is what gets you noticed in the market. I think as a founder, you should have the following perspective. The scarcest resource in the business community today isn’t capital, despite what some people will tell you. It’s attention. It’s focus. What’s the wrong way to get people’s attention? The wrong wrong way to get people’s attention is to yell successively more loudly about and make more and more ridiculous claims that you’re going to be unable to substantiate. CEOs do it all the time. It’s a mistake. It bites them in the butt. Stop doing it. If somebody listening is acknowledges deep down that that’s what they’re doing right now. They’re just yelling louder and louder and trying to top themselves. Stop doing it. Here’s what I often step small often seed and a- round startups through is there’s this progression I uh I like to go through and you’ll see where this is going and how it comes around to point of view. When you start the business it’s just people. It’s the five Ps. Remember Dave Blakeley’s five Ps, right? When you start it’s just people and then after a while you’ve got people, you’ve got some some beta clients, right? You got some pilots. So you’ve got people and a portfolio. Look, we’re real smart and we’re doing this amazing stuff with this technology for these folks. Then you’ve got process and then in time you have platform which is what everybody’s looking for especially in digital. I don’t think platform is at the top of the pyramid. At the top of the pyramid in my opinion and what gets people’s attention is point of view. It’s a unique perspective on the market where investors, other CEOs, potential partners, people you might invest in hear about your point of view. They read it on LinkedIn. They see you at at giving a TED talk or whatever, and they think, “God, that’s really interesting. Why did I never think of that before? That’s really remarkable.” So you show me a world-class venture, I will show you someone where I will show you an organization where the CEO or or the or other members of of of top leadership and founders have got a unique and distinct point of view on where the market is going or where the opportunities are. The last thing I’ll say is point of view doesn’t equal sales literature, right? It’s not like, hey, here’s my cool value proposition. It’s about where the world is going. It’s about how you know uh global supply chains are fragmenting into regional supply chains or it’s about the profound changes to the education market that will be wrought by gener by generative AI these types of things completely. So I have a founder who uh I’m like mentoring right now and they their business is killing it. Um they’ve got probably some of the strongest revenue traction. They’ve got really good clients. They’ve nailed the processes, but they’re like basically acting as like a COO. Yeah. And they don’t have that point of view. And they’re almost taking a thing of like, oh, I’m minding the store. And I’m like, you’re not minding the store. Like like if you don’t if you don’t come in with a point of view, someone’s going to come in and like put a CEO over you who will just take credit for all this and have a point of view and it’s probably going to be the wrong one. So, like have you been in situations where um people have been so good at the 0ero to one that they’ve actually built something that’s starting to flywheel, but then they don’t have the longer term big point of view and like how can they breadcrumb and get there? Because I think for some people that comes really naturally, but for other people that’s super hard. Yep. Happens all the time. I mean, hell, if it’s happening to someone you know that’s done a that’s built something zero to one. Yeah. Think of how often it happens in family offices. um in uh developing countries which really focus on operational excellence and lowcost um products and services as opposed to product leadership and innovation. This is every day of my life. So express in the negative, what do you not do? What you don’t do is you don’t say have a point of view, find some find some inferences, right? That’s just not fair. particularly if you’re uh working with someone who’s been brought up outside a US or Western European culture in a world of pure tangibles where for example in in in school in testing everything is a multiple choice test. You’re never asked to interpret ambiguous literature. That’s so interesting that because um without going into specifics I see this happen more with um uh black and white backgrounds like people who have more technical backgrounds because it’s like you know the system either works or doesn’t work right like there’s not a gray area between the two. Yes. And I think that that’s that’s just so that’s really really interesting you brought that up. So here’s the important thing to remember. Creating a unique point of view and and getting into the habit of finding inferences and finding implications and finding meaning and direction in the world around you as opposed to just turning the crank and running the operation. Number one, you should demand that. Number two, it is a learnable skill, not some sort of innate talent. And um this is an area where design thinking really has a lot to say. Yeah. There is no stronger catalyst for unique point of view um than open-ended dialogue with a variety of people who are not you. If you were developing a financial services company, a a a a BTOC financial services company for example, and you interview a group of people just with open-ended questions like, “What do you worry about in your finances? What do you hope for? If you had a magic wand, what would you change?” Right? If you do a couple things, if you set up a good open-ended interview script, if you have open-ended dialogue and park your agenda out out outside the door with a proper diverse range of people, right? Different age and life stage, different attitudes about technology, uh different socioeconomics, different state in the US or different country in the world or whatever. And if and then this is most the most important piece. If you ask yourself, what are some common themes I’ve seen across this small number of interviews? And now let me force myself to write an insight statement that starts with the words, I believe. It’s not your guy turning the crank where regulatory people and HR people are just telling her or him what to do and they’re turning the crank. It’s about asking yourself based on what I’ve learned from the market and from my stakeholders, what do I believe? That’s a muscle that can be exercised and people get very very good at it. I’ve seen it over and over. I’ve seen it my whole career. That’s like it’s it sounds like the simplest thing, but I feel like I’m always shouting from the rafters and I’m even doing this with myself where um just like get out of your Zoom box or get out of your office and go out and talk to your customer or go go talk to people in general. And for me, like it’s been a little too long since I’ve been here in San Francisco. And I I was having lunch today and like two people sitting next to me at lunch, I was just easedropping and they had they had just moved here from another country and were like, “Oh, I’m just getting into the startup community and this is what I’m building and this is how I’m thinking about building AI and and I’m like, man, I need to just like be here a lot more because the learning cycles for me, like meeting founders is is part of what I do. The learning cycle around that is is so much quicker. Is that really like what you’re talking about is like getting in like slipstreaming yourself into a place where you can have a lot of learnings for language market fit. I’m talking about having a lot of learning and in even more than that taking that learning and coming up with actionable insights and actionable conclusions. And yes, I mean I I mean uh I’m I’m happy to hear that the way I described it, it sounds like a simple thing. It’s actually devilishly difficult. Yeah. Right. And I’ve been doing this for decades. And every single program I work on, I mean, right now we’re working on some on some programs related to um improvements in mining and some others related to distributed energy resources. Every single program I work on, including those two that I’m that I’m involved with right now, another one that’s that’s really exciting about uh about modular housing, um I’m always incredibly nervous that we’re not going to come up with any kind of worthwhile insights and we’ve got nothing worthwhile to to move forward with. We’re not finding meaning. We’re not finding direction. We’re not finding a go forward path out of all this complex and contradictory information that we’re taking in. So I don’t mean to make Dave Blakeley’s rule of just is if somebody says the word just, you know, about any phase of building a business, they’ve never done it. You should disregard what they’re saying because they don’t know what they’re talking about. There is no just like, well, we just need to or you just need to apply this process. But it is learnable. It is not an innate talent and it should be valued and demanded by folks like you, by people on boards, by investors. I think that’s so interesting. I um Winston Churchill said, “America always does every every wrong thing first before it does the right thing.” And I’ll out myself right here is I think as a founder, I try to do I try to do everything but sit down and talk to a group of people and then come up with the statement that I believe. And you know, I’ve just learned to like force myself to do this over time and and just make it part of like my ongoing conversation, but I think it’s it’s just so critical. How often do you think people should go back and you know, the market’s moving really fast, AI is moving fast. If you’re a founder and you’re building an AI, how many times should you go back out to the customers and like update that belief statement? Is that like a monthly, quarterly, annual thing or like Yeah, like when you’re at a high velocity, same cadence as your as as the major updates in your product line. Okay. Right. I wouldn’t set up a cadence for gaining market insight. What I would do is I would I would set up I would build it around the cadence by which you plan to release, you know, updates to whatever you’re putting out. So if you see if you’re putting out pretty significant updates every 3 months, every four months, whatever it is, um then I would back calculate out of that some time to spend with customers and some time to spend on synthesis, the art of finding meaning and finding direction in what it is you’ve learned. and as appropriate, adjusting your mission statement, adjusting who you’re going to talk to next, deciding what you need to learn more about, deciding who you might need to partner with, this sort of thing. That’s awesome. You know, I I was talking with another founder over coffee the other week and um their culture uh is very non-confrontational. So, I was trying to like advise them on how to build their own company culture. So, like where they’re from is non-confrontational. And how that was showing up in their business is they would tell, you know, uh, Brennan employee, hey, everything’s great. I trust you. You’re good to go. And then actually be really frustrated that Brennan didn’t show up at this time or didn’t do this at this point. And and I gave them the advice that that’s creating, you know, a culture in the business that’s inauthentic and that it’s actually incredibly toxic because what it’s doing is it’s saying your word doesn’t matter and you also don’t know where you stand from the CEO’s perspective. So like let’s say you’re in that track and you’re from a different culture and you’ve kind of created that culture as a a founder or you aspire to have a really like honest direct culture. Yeah. What are does is there a Dave Blakeley rule on on clear and honest or transparent culture and how to hold people accountable? Sure. So look based on a two-minute description you gave the founder you’re describing uh good advice. Um, being excessively non-confrontational is paradoxically poisonous and destructive. Trying to avoid hurting people’s feelings and trying to avoid being destructive is destructive. That’s one of the weird ironies of business and any, you know, any number of other any number of other group activities. Um, Eric Shinseki, an army general, once said, “I don’t know the sure recipe for success, but I do know the recipe for failure. Try to please everyone. Here’s what happens. You’ve seen it. I’ve seen it. And if anyone listening h admits to themselves that they do this, they’ve got to stop. What happens is um uh your employees, your colleagues, they see a leader who says and does entirely separate things for different people, right? Yes. Um, if I’m watching you as a CEO say one thing to your investors, one thing to your board, and one thing to your team, and those things don’t add up, you’ve lost my trust forever, and it’s very, very hard to gain it back. Right? Wow. What you’re doing is you’re avoiding discomfort. Your brain your brain is incredibly finely tuned to avoid things that make it uncomfortable and unhappy. And so what you’re doing is you’re doing an amazing job improvising on the fly, improvising different narratives for your board, for your team members, for your brand new employees who you’re onboarding. You’re telling them all something different. You’re blowing it with every single one of them. And you will and you will never ever succeed. So look, um I think that I think that it’s very important um to to ask yourself early in your career as a business person, what do I believe? And to the point you made earlier about cycles of self-learning, you know, ongoing cycles of learning, it’s really embarrassing to ask yourself and to write down, you know, I’m Brennan. What do I believe? because it’s it it reads like, you know, here you’re this you’re the CEO and yet it reads like a badly written high school civics essay or something like that, but you have to start right or it might sound really cliche. I often tell people um what do I believe? I believe that um that democratic capitalism provides globally the best path for upward social and economic mobility. Well, that sounds like some boring thing out of a textbook, but the fact is it’s a starting point. It’s what I believe. Ask yourself as a leader in all sincerity. Don’t lie to yourself. What do I believe? Right. And then share those beliefs and share that honesty at every level with every group that you speak to. Like I think what you’re saying is dead on, but just to clarify to the audience to um like I know you need to have a different message for your board, a different message for your co-founder, a different message for your new employees because they all have different levels of context and it’s your job as a CEO to provide the appropriate level of context to the right person at the right time. And so can you elaborate a bit more on like different levels of context and messaging? Yes. um versus like I’m feeding someone a bunch of and I know I’m feeding someone a bunch of because I’m lying to myself. Right. Right. Look, here’s the difference. Of course, you need to respect confidentiality and non-disclosure. You can only say certain things to certain people. And of course, the dialogue you’re going to have with your board is different in specific inspecific with the dialogue that you’re going to have with your people. M what’s inexcusable is when rather than taking what you believe and and examining what in all sincerity you believe right now to be the case with your business where it’s doing well where it’s not doing well and positioning that in ways that is appropriate to your audience. What’s inexcusable is when you invent completely different narratives that have nothing to do with the truth. Right? expressing different angles of your authentic belief. That’s just good communication, right? I’m talking to you in a different way, you know, than than than than I would talk to my three-year-old grand niece. I mean, it’s a silly example. Um uh it’s it’s it’s inventing a narrative to suit your audience as opposed to um coming up with suitable ways to convey the same truthful beliefs that worries me. I like that a lot. Um so how let’s call out some companies as an example. Um around different cultures. So like um the Colisons at at Stripe they uh they had a completely open culture. Yes. So like at one point in time and I don’t know if this is still true but at one point in time you could like log in and search any conversation any meeting anywhere in Stripe and that was one way like trying to just nail the transparency and the context thing. Are you a fan of that or like have you seen I think that eventually broke at scale and also them being a financial institution like I don’t think they’re still doing that but like there’s been some crazy innovative things that different startups have done like everything from everybody like Square for instance um I think no one has a job title like VP or SVP or in in the old days like I think they were a very flat or so then it was like similar information. Can you talk a bit about what you think about those two things as well as like maybe systems CEOs or founders can design um to promote this context and transparency? Sure. Sure. So the edge cases get a lot of press, right? Um the radical transparency at Stripe where anybody could get access to, you know, other people’s salaries, for example. Um Ray De Leo’s approach of of of screaming and swearing at people and calling them stupid, right? uh in in in front of their in front of their colleagues at Bridgewater Associates. These are the edge conditions that get a lot of press. I think two things. First of all, I think there are any number of appropriate levels of candandor and transparency, all of which can work as long as they’re applied um consistently. The other thing I think you need to do is you need to take a page from the uh say from the SpaceX playbook and inform people as soon as they start to interview what they’re getting themselves into. Right? People at SpaceX work every day, all day, every weekend. They get called in the middle of the night. I don’t feel sorry for them at all. Why do I not feel sorry for them? They opted in. They opted in. As soon as you sit down for an interview at SpaceX, they say, “You can never be sure of a vacation. You can never be sure of an evening. You can never be sure of a weekend. They make that so abundantly clear. You know, that’s one of my favorite things to do with I I do that actually with definitely all my executive hires, but I try to do this with everybody where I almost like reverse sell. Yeah. And it’s like if I was bringing you on, I’d be like, Dave, these are all my problems like that are keeping me up at night. These are the things that are the most messed up or effed up in my business. And then what’s so funny is I’ve recently started um 30 days after someone starts I go I in the past I had to join these companies and they’d be like everything’s amazing we’re a rocket shipper to come in and then you like come in and it’s like that scene where you know every you know the the meme where it’s like this is fine everything’s fine and you’re like in the fire like I’m just like what did I just walk into and it’s like you’re just paying me a ton of money it’s like I could actually help you know and so that’s that’s something like I always do where it’s like I I call it reverse selling, but to me it’s just like it’s like radical honesty. That’s that’s a really interesting takeaway for me that I I’m going to I’m going to remember this and and and think about where I can apply it and think about where I can apply it with some of my some of my portfolio companies. Let’s talk about where you know organizations at the extreme. Your stripes, your Bridgewaters, your SpaceX, your Teslas, your Nvidia, right? With with Jensen Dwang being really tough on people. Let’s talk about where they can go too far. This is a very qualitative call. But the fact is if if um borderline psychotic or sociopathic personalities on the part of the leadership use radical candandor as an excuse for lousy behavior, that is not okay. Right? For me to say, “Look, Brendon, you need to understand, I wear my heart on my sleeve. I’ll say anything to anybody.” That’s not always acceptable. No, that may be me using using cute and cliche business language to justify really unhealthy behaviors. That’s like me saying, you know, you know, Brandon, you know, once a day at most, I’m going to take out a 2x4 and hit you over the head with it, but it’s okay because I’ve been completely transparent and I’m about to clock you with a 2x4. No, it’s not okay. It’s pathological behavior. It’s not acceptable. I’m using, you know, trendy business speak to justify pathological behavior. You need to keep an eye out for that. There are sociopathic and pathological CEOs out there who absolutely do that crap. I think you also can like develop bad habits from bad culture. So like I’ll I’ll I’ll open share here. Um I I have clinical anxiety. Yeah. And so the way that that used to show up in my 20s and I came out of banking and I would just like feel the success or the failure of the business like really strongly and I would roll into a meeting room and I would just start being really tough on people, people who had no context or anything. and it’s because I’m taking on too much in the business. And there’s a bunch of good reasons for it, but like end of the day, it’s like wrong and not right. And the the takeaway from that that I learned really strong is like people don’t remember all these little interactions with you. They remember that one and they remember how you make them feel. Yep. And people always remember how you make them feel. And I think that’s so important. And that was a huge really tough lesson for me to learn um as a as like a CEO and as an operator is that you can do good work but if you’re if you have anxiety or you have spikes as a leader don’t take that out on the people in the room and don’t take that out on the team and like that’s not right. And you know an executive coach of mine later because I’ve developed a bunch of skills around this was like you know I was so mad because um I forget what like I don’t remember why I was mad. I was just really frustrated with the team. And I think with like most CEOs and founders, there hits moments where you’re just like so mad at the team. All of us. And you’re like, I’m gonna have them go and like fix this and like grind to get it done. And she was like, why are you like why? And I’m like, because like you know, they need to learn and like D. And then she was like, you’re just trying to make them like why would you want to make your team feel bad? Like it’s learning, but like why are you not abstracted from this and being like, hey, this is learning. These are my expectations. And it was just unlock I love that you called out the psych the psychotic and the sociopathic behavior that I think the system encourages and I would encourage founders like especially to like work on themselves because like there are moments and times when you can just like show up not like yourself cuz like we’re doing stressful stuff you know but it should not be like I don’t think radical cander should be tolerance for like treating people poorly you know it’s not and and and look if you get the idea that I haven’t been victim to this. There were years in my life where I really felt like there was a black cloud following me around all the time. I’m on vacation. I’m home playing with my little kids. There’s that black cloud raining down on me, you know. And it and it and it had to do with with problems. Some that I couldn’t have avoided and some of my own making of of of of avoiding risk unnecessarily, of avoiding difficult conversations, of stalling too long on making decisions. I mean, you name it, I’ve made the boneheaded mistakes. You know, the one thing I will honestly say is I learn from those mistakes and I do I can’t say I don’t make them twice. I do everything possible not to make the same mistake. I had a good mentor tell me um you chose all this like you cho as a CEO like you chose cuz I was having a particularly bad day and they were like you chose every aspect of the situation. So like why are you frustrated? Right. Right. not only did you choose it, you worked really hard to put yourself in a situation where you’re miserable and you also are like doing too much or whatever. Um, and so another fun thing that I tell founders um is, you know, if they’re complaining or they’re having a really tough day, right, like in that tough week where like you lost an executive or you lost a key account or the investor passed on you, I go, “Well, this will be the easiest day of this business.” Yeah. Cuz like it it only gets harder from there, right? And and I think that that’s that’s so funny. I’d love to talk to you a bit about like how founders can ensure that their uh their actions align uh with their stated values, right? So like we talked about some stuff and I would say that like in the past like I’ll be the first to own this on this podcast. Like I haven’t always my actions have not always aligned to what my stated values are or the culture I want to create. So like when you’re in the trenches and you’re feeling all these feelings, how do you how do you check yourself on that? I think self-insight is a a lot of this, you know. Um it’s so dramatic and there’s so many ups and downs to starting a business that there are people that just get uh they just end up almost in this permanent state of um of uh hypervigilance and hyper awareness. And there’s no easy answer to what you’re just describing. There really isn’t. But I think there’s a fundamental difference between being tense, being unhappy, being pissed off, in general, being hypervigilant or in an in a in an enhanced state of arousal. And even though you can’t control it, because we can’t control what we feel, at least being aware of it, right? Because we’re both anxious guys. At least you or me saying, “Yep, there’s my anxiety welling up and yelling at me again.” At least being aware of it. And it’s this amazing ability we have um uh uh as humans to comment ourselves on our own minds. Yeah. Right. What I found over years and years and years and it really is the work of a lifetime is mindfulness over your own mental constructs and over your responses and realizing that at the end of the day things are just thoughts. Yes. you know what what you’re experiencing is just thought that in a you know in a cognitive behavioral way has revved up into this really intense emotion and is having physical manifestations in your body. Being aware of that makes a huge difference. Have you ever read the book The Body Keep Score? You’re like the third person to recommend it to me. I need to pick that up. I need to pick that up. So uh like I have trauma like lowercase t traumas like in my childhood and um the like so much of that ch like transitions into how I’m a leader and so like you know anxiety can feel like there’s a tiger in a bush but sometimes there actually is a tiger in the bush like your your business could be running out of money like it actually could be very existential and so I would do a lot around awareness and but then I’d still be really really anxious and then um I basically like this book is incredible like you you should definitely read it. Um because it’s also around like you can do a ton of meditation to to do that out. And then I also use a lot of like fitness now to to get that. And my big thing is the minute that um like I had uh a blip on like a cap table this morning and I found myself getting pissed off at my at my lovely finance guy who’s amazing and he’s like worked with me for like 15 years. And I sat there thinking to myself and I was like, “Okay, like I probably am just like why am I feeling emotion on this?” And then that’s that’s like my biggest trigger now. It’s like if I’m feeling any sort of like charge around a response back out to my team, I immediately go, “Okay, I need to either meditate, sleep, or work out.” Yeah. And like that’s the thing that I’m always working on because when I take action when I’m overly charged, that’s when I cause damage. Yes. And I don’t know if you have a similar thing too, but absolutely. both both the value of exercise and meditation and also being aware of those triggers. I was pissed off this morning, too, because a guy that I’m working with had to do something really important and he didn’t do it. And when people don’t do what they say they’re going to do, you know, it helps to be aware of this, it gets me really pissed off because because I really pride myself on being responsible and on and on delivering to my commitments. I don’t make commitments unless I’m confident I can deliver on them and then I stay up as late as I need or or do whatever is required or commit whatever resources are necessary to live up to my damn commitments. That’s just really important to me. I know it’s a trigger to your point. Um, everybody’s busy. It’s it’s also very trendy to talk all the time how busy you are and how backtoback your schedule is. Sitting meditation is so important. Um, I I’m still bad with it. Like I still have such a hard time like taking the time to do it. Everybody’s bad. Everybody has a hard time finding the time. Everybody Everybody experiences monkey mind, right? Everybody thinks, “Oh, they’re good at it. I’m not good at it.” No, no, no. Not only does sitting meditation do wonders to help you understand and get to know yourself better and and to help you to respond rather than reacting, which is a lot of what we’re talking about here, right? Along with other healthy habits, everyday stuff, eating well, exercises, getting exercise, getting enough sleep, right? But the other, you know, uh, uh, fantastic thing about meditation is it’s a pretty wellproven fact that to be creative, you have to have episodes in your day or in your week where you do nothing. If you are truly pulled from thing to thing by your Outlook calendar, your Google calendar or whatever it is, there is, no matter how clever or creative you are innately, there is very scant chance that you’ll ever be creative. committing to sitting down to 20 minutes of of uh sitting meditation. I am absolutely convinced and there’s some neurological evidence that it opens up pathways in your head towards creativity out of the box thinking and you think of things that you simply would not have thought of over the course of your normal busy day. my co-founder Francis who set us up and you know very well he actually was like this is literally what we’re paid for is to like take that time and be creative and I think it’s so easy to fill the day with reactivity especially when your business is taking off like if your business is taking off or if your business isn’t doing well like it’s really hard to find that space well you say it’s easy to fill your day with reactivity for me it’s impossibly difficult not to fill my day with reactivity so I mean yeah look I mean it takes so much effort and also I find comfort in reactivity. I find comfort in email browsing. Feels so easy. That’s easy. So productive. Yeah. But but hold yourself to hold yourself to a higher standard. Right. You’re not meditating cuz your brain doesn’t want to do it cuz it’s uncomfortable and hard, but you know it’s good for you. I turned off all the notifications on my phone with Slack and email until I’m intentional going in. And that was like one of the biggest game changers I did. Yeah. I have to ask Dave, like you’ve worked with some violent extremists and even worked on a nuclear submarine. Um, and and you’ve just had a really varied career. Um, what’s the story there? And did those extreme experiences teach you anything about leadership or honesty under pressure for that like people like startup founders like me or others could like take? I just treasure the extreme experiences that I’ve had really. um the program you’re you’re mentioning which was with Google ideas the um the market segmentation for violent extremists was you know uh religious violent extremists, racists, um uh uh street gangs, political violent extremists and so on. We interviewed them. We did what we were talking about earlier in the podcast. We looked for common threads. We looked for countermeasures to violent extremism. And your question is a timely one. I just got back um uh from a tour of South Africa with a group of Stanford students who are who are Knight scholars. It’s the Phil Knight Foundation, Phil Knight from Nike. A very clever history professor named Dr. Jim Campbell um asked to teach these these incredibly high potential Stanford students about leadership said let’s bring them to South Africa and let’s show them how people like Mandela and Tutu rose above seemingly intractable problems from racism to poverty to you know grinding aparthide to things like that. some of the things I’ve learned about true leadership and you know uh um I mean we could talk for the next 5 hours about this but again I feel like when you show me someone who I feel is a remarkable leader I’ll show you someone who’s humble as opposed to arrogant. I’ll show you someone who’s tolerant as opposed to single-minded and exclusionary. I’ll show you someone who yes they’ve got a vision but they’re a pluralist. True leaders believe that there are multiple valid conflicting perspectives, each of which is valid, and they’re very good at listening to those. And finally, you show me, show me a good leader, I’ll show you someone not who just barrels forward, you know, with their own initiatives, but who’s a really good, really active listener. They’re not someone who’s like phrasing the next thing in their mind even as they’re listening to you or trying to multitask. they’re wholly engaged while they’re listening to you. So again, I would say tolerance, humility, pluralism, um, and, uh, and and an active listening are hallmarks of some of the most impressive leaders I’ve ever met. That’s so great. Um, I love I love all the stuff you’ve picked up from different backgrounds. So, I have some specific quick questions that we can hit. Let’s do it. Um, lightning round. Lightning round. Lightning round. Let’s go. Uh, what’s the most common mistake people make in your industry that you wish you could fix just overnight? People still fail to understand their stakeholders honestly and empathetically. They still hide behind market research. They still just glom onto an end user as opposed to understanding the whole complex uh ecosystem of stakeholders s that are that are important to their business success. That’s got to change. What’s one thing you think all successful people do that no one talks about? And I know you hit some of that in that answer before, but you heard this from me before. Self insight, right? The knowledge of a what you’re really good at, what your superpower is, and b how you can bring in other people around you and develop relationships of deep trust to augment those areas where you’re less where you’re inherently less strong. What’s one decision that completely changed your career career? I’m older than you are. People didn’t used to talk about pivots, right? I studied electrical engineering and physics. I wanted to go into space science. I got a job at the space sciences lab. Was supposed to be my dream job. Most boring thing I ever did. Everything was scheduled. I was working on the kek telescope. This majestic, amazing vision. It was like 20 years out. It was so deenergizing. I was so bored. And I thought, “Oh my god, have I chosen a completely wrong career? Am I ever going to be happy?” I was panicked. It was stupid. I didn’t understand the importance of a pivot. pivoting away from uh uh astronomy and and you know and and and deep physics into much more actionable shorter time frame uh mechatronics was a really important step for me. Dave, we could have had like a 4hour podcast on all the things I want to talk to you about. Been a pleasure. So great having you on.