Be Your Best in 2026: The Most Important Lessons from The Knowledge Project (2025)

0:00:05 Welcome to the final episode of 2025. I pulled together some of my favorite moments from the year.
0:00:10 These conversations help me think better, work smarter, and live with more intention.
0:00:17 It’s time to listen and learn. Toughness, kindness, and clarity. All three. But don’t forget the
0:00:22 toughness. Because you don’t want yes people around you. You want people who say, why don’t
0:00:26 we push the boundaries of our thinking? AI makes me get to the answer perhaps more quickly,
0:00:32 but you need someone with experience to know which of those references matter to the business.
0:00:39 I am genuinely concerned that because of different societal factors, because of people who maybe lost
0:00:44 out on some social skills during the pandemic, there is not that rejection resilience that many
0:00:50 of us need in life. You mentioned that we can engineer trust. How do we do that? One is repeated
0:00:56 exposure. Second is establish a set of shared values. Everything is here to teach me and help
0:01:00 me. It’s all working for my good. So we’re going to go look for those moments when you’re
0:01:03 most uncomfortable and remind yourself, this is my teacher.
0:01:09 From when a customer orders something, when it gets through the distribution center, how is
0:01:14 it going to be picked, packed, packaged, and shipped? And when you look at that from a flow perspective,
0:01:15 you start thinking about new solutions.
0:01:21 Getting really, really comfortable with being uncomfortable is magic. And I wasn’t always good
0:01:24 at that. The right entrepreneurs, the best entrepreneurs, they just simply outcare other people.
0:01:37 When you talk about inputs versus outputs, what inputs do you think about in life?
0:01:46 Well, I think the inputs I think about are, you know, it depends on what I’m trying to get
0:01:52 accomplished. But if the inputs are just thinking about hard work, do I get up every day? Do I want to stay
0:01:58 healthy? Do I get up every single day and work out? I hear that you work out every single day because
0:02:01 instead of trying to figure out which days you’re going to work out, it’s always a negotiation
0:02:08 with which days. And some days you don’t feel like exercising. You just work out every day.
0:02:13 I have the same philosophy. You just get up every single day and do the things that are important.
0:02:19 So the inputs I have is I get up every morning, I work out, I look through, I read through my email,
0:02:24 and I try to think about what’s the most important thing that I have to get right today.
0:02:31 What’s the most, and, and think about first order issues. What is the first order issue that I have
0:02:36 to solve? What is the first order issue of a company that needs to get fixed? What is the first,
0:02:46 what is the thing that I need to do to influence an outcome for, um, for a founder? And, you know,
0:02:51 that’s very, very clarifying. Often we can create a very, very long to-do list and then you’ve got to
0:02:55 pop up a level and just look at the to-do list. What’s the most important things I have to get
0:03:00 accomplished? Because if you just list all the to-dos, you probably will not be able to get to all of
0:03:05 them. And the most important thing might be the last one you list. And so you can’t just go down that
0:03:12 list and do them one by one. Often it’s by popping up a level where you sort of look at the whole list
0:03:17 and it’s like, okay, well, most of this is not important. Is that what you mean by first order
0:03:21 issue? I think you mean something a little more nuanced. Some people talk about the most important
0:03:31 thing. Um, and I think, I think about first order. If I get this problem, I have a problem on my hands.
0:03:37 If I get to the first order issue and get to the root cause of that, usually that helps solve that
0:03:46 problem. And there are other issues that are not first order. Um, and that concept is quite important.
0:03:54 We also sort of navigate that into other, uh, situations where, um, where they are crucible.
0:04:03 So as an example, like you, you have, you have situations where the website’s not working fast
0:04:07 enough. That’s Apple’s. We had a situation where the website’s not fast enough. Is the first order
0:04:13 issue that we have too many pictures? Well, we want the pictures. We have lots of photos. We want to show
0:04:19 those photos. Is the first order issue that we need to, um, just trim the number of search results
0:04:25 while customers want longer search results? It’s like, no, it’s none of that. We need to figure out
0:04:32 how to make the website go faster. And so we start caching the, the search results. We start caching
0:04:38 things. And so you start developing the technologies that solve the speed issue. But the first order issue
0:04:44 is that we need to solve this with technology, not with a bunch of either or solutions. Um,
0:04:50 that’s an example that I learned a long time ago. Another situation is the distribution at
0:04:58 Zappos was not flowing well. Um, and we couldn’t figure out which process was broken. Was it the
0:05:05 picking process? Was the, was the ordering process broken? What was broken about it? And we went and just
0:05:16 looked through the flow and the flow was broken. And so, uh, there was too many handoffs, uh, across all of
0:05:22 these different discrete processes. And so we had to sort of pop up a level and figure out what the flow
0:05:30 of, from when a customer orders something, when it gets through the distribution center, how it’s going to be
0:05:38 pick, packed and, uh, packaged and shipped. And when you look at that from a flow perspective, you start thinking about
0:05:44 new solutions that allowed there to be much better flow throughout the distribution center than been, then to batch
0:05:52 things for picking, batch things for, um, packing, patch, batch, batch things for, uh, for shipping.
0:05:58 So that’s what you mean by first order. Uh, I want to get into more of your experience, not only at Zappos,
0:06:04 but, uh, being on the board of some of the companies that everybody has heard of, um, today are being
0:06:08 involved. But before we get there, I want to come back to the school for a second. Are there any other
0:06:12 experiences that you had during school with teachers that might’ve impacted you?
0:06:19 Um, you know, earlier on in junior high school, I was, um, I was suspended from the computer lab
0:06:25 because I built, you know, this was very old. So they’re a Radio Shack TRS 80s. So we call them
0:06:34 trash 80s today. Um, and there was the computer lab, you know, you had to run time in our computer
0:06:40 lab to, to use the computer. And I built this game and the central server at the time was literally a
0:06:49 floppy drive where all of us saved our programs there. And one day, uh, a bunch of the students,
0:06:54 uh, in the computer lab all found the game that I programmed and then started playing with it.
0:06:59 The teacher and the principal just happened to walk in and saw that we’re all playing this game.
0:07:05 And, um, I was told that computer lab is valuable time and you should be doing something much more
0:07:10 productive than, than producing a game. So I, I was no longer allowed to work in the computer
0:07:18 lab and the computer lab teacher was Mrs. Pitosa. And she’s, she also ran the math team and she
0:07:22 said, well, you’re, I’m sorry, the principal wants you out of the computer lab, but you should join
0:07:28 the math team. And I joined the math team there. And, um, one of the things I was very good at was
0:07:32 math. And she told me that if you want to be a leader and you want the team to win,
0:07:38 it’s not good enough for me to just solve the problems. I mean, figure out how to get the rest
0:07:45 of the team to perform. And so I started teaching the rest of the math team, some of the reasons why
0:07:49 I was able to solve some of these problems more quickly than they were. They’re very talented, but
0:07:55 I had figured out tricks that they had not figured out. And they taught me tricks that I had not figured
0:08:00 out. So we got better and better by riffing each off each other. And so I learned the value of teamwork
0:08:04 by just being thrown into a situation like that.
0:08:10 Such an interesting front row seat into what’s happening. Do you think founders go astray when
0:08:15 they start listening to too many outside voices? And this goes back to the, I’m sure you’re aware,
0:08:20 the Brian Chesky, you know, the founder mode. Do you think, talk to me about that.
0:08:28 I have such a nuanced point of view on this because it is decidedly not simple. Uh, so broadly
0:08:37 speaking, I really like the spirit of founder mode, which is just having deep founder led accountability
0:08:43 for every decision at your company. Um, I think that that’s how great companies operate. Uh,
0:08:50 and when you, you know, proverbially make decisions by committee or you’re more focused on process than
0:08:56 outcomes, um, that produces all the experiences we hate as employees, as customers, you know, that’s the
0:09:01 the proverbial DMV, right? You know, it’s like process over outcomes. Um, and then similarly,
0:09:09 uh, you look at the disruption in all industries right now because of AI, you know, the companies
0:09:13 that will recognize where things are clearly going to change, like everyone can see it. It’s like a,
0:09:18 you know, slow motion car wreck. Everyone knows how it ends. You need that kind of decisive
0:09:25 breakthrough boundaries, layers of management, um, to actually make change as fast as required in
0:09:32 business right now. The issue I have not with Brian’s statements, Brian’s amazing, um, is how
0:09:37 people can sort of interpret that and sort of execute it as a caricature of what I think it means.
0:09:44 Uh, you know, there was a, I remember after Steve jobs passed away and, you know, um, I don’t know,
0:09:48 Steve, I’ve met Steve a couple of times. I haven’t never worked with him in any meaningful way,
0:09:54 you know, but he was sort of, uh, if you believe the story is like kind of, uh, pretty hard on his
0:09:59 employees and, and very exacting. And I think a lot of founders were like mimicking that, you know,
0:10:03 done to wearing a black turtleneck and yelling at their employees. I’m like,
0:10:07 not sure that was the cause, you know, uh, I think Steve jobs, taste and judgment
0:10:12 through, you know, executed through that, you know, packaging was the cause of their success.
0:10:18 And somehow, and then similarly, I think founder mode can be weaponized as an excuse for just like
0:10:24 over micromanagement. And that probably won’t lead to great outcomes either. And most great companies are
0:10:31 filled with extremely great individual contributors who make good decisions and work really hard. And,
0:10:37 uh, companies that are like solely executing through the judgment of individual probably
0:10:42 aren’t going to be able to scale to be truly great companies. So I have a very nuanced point because I
0:10:48 actually believe in founders. I believe in actually that accountability that comes from the top. I
0:10:55 believe in cultures where, you know, founders have license to go in and all the way to a small decision
0:11:00 and fix it. The infamous question mark emails from Jeff Bezos, you know, that type of thing. That’s,
0:11:04 that’s the right way to run a company, but that doesn’t mean that you don’t have a culture
0:11:09 where individuals are accountable and empowered. And, uh, you don’t want, uh, you know, people trying
0:11:13 to decide, make business decisions because of what will please our dual leader, you know, which is like
0:11:18 the caricature of this. And so, you know, after that came out, I could sort of see it all happening,
0:11:22 which is like some people will take that and be like, you know what, you’re right. I need to go down
0:11:25 and be in the details. And some people will do it and probably make everyone who works with them
0:11:30 miserable and probably both will happen as a consequence. So totally. Thank you for the
0:11:34 detail and nuance that I love that too. Do you think engineers make good leaders?
0:11:39 Jeff Bezos: I do think engineers make good leaders, but one thing I’ve seen is that
0:11:49 I think that I really believe that great CEOs and great founders, um, start usually with one specialty,
0:11:57 uh, but become, uh, more broadly, uh, specialists in our parts of their business. Um, you know, I think
0:12:05 the, uh, businesses are multifaceted and rarely is a business’s success due to one thing, uh, like
0:12:10 engineering or product, which is where a lot of founders come from. Often your go to market model
0:12:16 is important, uh, for consumer companies, how you engage with the world and public policy becomes
0:12:23 extremely important. And I think as you see, um, uh, founders, you know, grow from doing one thing
0:12:28 to growing, to be in a real meaningful company like Airbnb or Meta or something, you can see those
0:12:34 founders really transform from being one thing to many things. Um, so I do think engineers make great
0:12:41 leaders. I think the first principles thinking, the system design thinking, um, really benefits things
0:12:49 like organization design strategy. Um, and, but I also think that, you know, uh, when we were speaking
0:12:55 earlier about identity, I think one of the main transitions founders need to make, especially
0:13:02 engineers, uh, is you’re not like the product manager for the company or the CEO. And at any given day,
0:13:06 do you spend time recruiting an executive because you have a need?
0:13:13 Do you spend time, uh, on sales because that will have the biggest impact? Um,
0:13:19 do you spend time on public policy or regulation? Because if you don’t, uh, it will happen to you
0:13:26 and could really impact your business in a negative way. And I think engineers who are unwilling to
0:13:32 elevate their identity from what they were to what it needs to be in the moment often leads to sort of
0:13:38 plateaus, uh, in companies growth. So a hundred percent, I think engineers make great, um, leaders and
0:13:44 it’s not a coincidence. I think that most of the Silicon Valley, great Silicon Valley CEOs came from
0:13:50 engineering backgrounds. Um, but I also don’t think that’s sufficient either as your company scales. And I
0:13:54 think that making that transition is all the great ones have is incredibly important.
0:13:58 To what extent are all business problems engineering problems?
0:14:03 That’s a deeper philosophical question that I think I have the capacity to answer. Um,
0:14:12 what is engineering? What I like about approaching problems, uh, as an engineer is, uh, first principles,
0:14:19 thinking and understanding, uh, the root causes of issues rather than simply addressing the symptoms of
0:14:25 the problem. And I do think that coming from a background in engineering, that is, uh, everything
0:14:30 from process, like how engineers do a root cause analysis of a outage on a server is a really great
0:14:36 way to analyze why you lost a sales deal. You know, like I love the systematic approach of engineering.
0:14:43 One thing that I think going back to good ideas that can become caricatures of themselves,
0:14:49 like one thing I’ve seen though with engineers who go into other disciplines is, um, sometimes you can
0:14:55 overanalyze decisions in some domains. Let’s just take modern communications, which is driven in social
0:15:04 media and, and very fast paced. Um, having a systematic first principles discussion about every, you know,
0:15:11 tweet you do is probably not a great comm strategy. Um, and so, uh, and then similarly, um,
0:15:16 you know, there are some aspects of say enterprise software sales that,
0:15:22 you know, aren’t rational, but they’re human, you know, like forming personal relationships,
0:15:27 you know, and, and the importance of those to building trust with a partner. It’s not all just,
0:15:33 you know, product and technology. And so I would say, I think a lot of things, uh, coming with an
0:15:39 engineer mindset could really benefit, but I do think that, uh, taking that to its like logical
0:15:46 extreme can lead to analysis paralysis, can lead to, uh, over intellectualizing some things that are
0:15:51 fundamentally human problems. And so, yeah, I think a lot can benefit from engineering,
0:15:54 but I wouldn’t say everything’s an engineering problem in my experience.
0:15:58 You brought up first principles a couple of times. You’re running your third startup now,
0:16:05 Sierra. It’s going really well. How do you use first principles in terms of how do you use that at work?
0:16:12 Yeah. It’s, it’s particularly important right now because the market of AI is changing so rapidly.
0:16:24 So if you rewind two years, you know, most people hadn’t used ChatGPT yet. Uh, most companies
0:16:31 hadn’t heard the phrase large language models or generative AI yet. And in two years you have ChatGPT
0:16:37 becoming one of the most popular consumer services in history, faster than, than any service in history.
0:16:46 technology. And you have across so many domains in the enterprise, uh, really rapid transformation.
0:16:51 The law is being transferred, transformed. Marketing is being transformed. Customer service,
0:16:57 which is where my company Sierra works is being transformed. Software engineering is being transformed.
0:17:04 And the amount of change in such a short period of time is, uh, I think unprecedented. Uh, and, uh,
0:17:10 perhaps I lack the historical context, but it feels faster than anything I’ve experienced in my career.
0:17:16 And so as a consequence, I think, uh, if you’re responding to the facts in front of you and not
0:17:23 thinking from first principles about why we’re at this point and where it will probably be 12 months
0:17:29 from now, the likelihood that you’ll make the right strategic decision is almost zero. Uh, so, uh,
0:17:35 uh, as an example, uh, it’s really interesting to me that with modern large language models,
0:17:42 one of the careers that is being most transformed is software engineering. Uh, and, you know,
0:17:47 one of the things I think a lot about is how many software engineers will we have our company three
0:17:54 years from now? What will the role of a software engineer be as we go from being authors of code to
0:18:00 operators of code generating machines? Um, what does that mean for the type of people we should recruit?
0:18:06 And if I look at the actual craft of software engineering that we’re doing right now, um,
0:18:11 I think it’s literally a fact that it’ll be completely different two years from now.
0:18:16 Yet, I think a lot of people building companies hire for the problem in front of them rather than
0:18:21 doing that. But two years is not that long. Those people that you hire now will just be getting really
0:18:28 productive a couple of years from now. So we try to think about most of our long-term business from
0:18:33 first principles, everything from, I’ll say a couple examples in our business, our pricing model is
0:18:38 really unique and comes from first principles thinking rather than having our customers pay
0:18:43 a license for the privilege of using our platform. We only charge our customers for the outcomes,
0:18:49 uh, meaning if the AI agent they’ve built for their customers solves the problem, there’s like a usually
0:18:54 a pre-negotiated rate for that. And that comes from the principle that in the age of AI software isn’t
0:18:59 just helping you be more productive, but actually completing a task. Uh, what is the
0:19:04 right and logical business model for something that completes a task? Well, charging for a job
0:19:11 well done rather than charging for the privileges of using the software. Um, similarly, um, you know, we,
0:19:16 with a lot of our customers, you know, we help deliver them a fully working AI agent. We don’t
0:19:23 hand them a bunch of, uh, software and say, good luck, you know, configure it yourself. And the logic there is,
0:19:31 you know, uh, in a world where, uh, making software is easier than it ever is before and you’re delivering
0:19:35 outcomes for your customer. Um, the delivery model of software probably should change as well. And we’ve
0:19:40 really tried to re-imagine what like the software company of the future should look like and trying
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0:22:04 Do you think we’ve sort of broken dating in a way where, I mean, I’ve been on dates with people,
0:22:08 we all know people who are, I wish people would come up to me and ask me out. I wish I didn’t have
0:22:14 to use a dating app. And my defense of, you know, thinking immediately in this is like,
0:22:19 society has taught guys not to approach women anymore. What’s your reaction to that?
0:22:23 This is something that I’m thinking about a lot, specifically with Gen Z and Gen Alpha.
0:22:29 So I was recently speaking to somebody, she’s a 16-year-old entrepreneur, and she’s trying to deliver
0:22:36 help for teen daters. And she said by far the number one thing that she gets questions about is how to deal
0:22:43 with rejection. And so I am genuinely concerned that because of different societal factors, because
0:22:49 of people who maybe lost out on some social skills during the pandemic, because of people who live
0:22:55 a lot of their lives online, there is not that rejection resilience that many of us need in life.
0:23:01 So if you want your dream job, you need to go out there, get a lot of no’s and go after it. You don’t
0:23:05 just sit at home waiting for a LinkedIn recruiter to message you about your dream job. That doesn’t
0:23:11 happen. You have to make it happen. And the same thing is true with dating, is that you have to shoot
0:23:17 your shot. You have to approach people in public. You have to take a risk. And so I’m encountering a lot
0:23:24 of people who are very afraid of rejection and are not taking those risks. And I think that it’s leading
0:23:26 to fewer relationships.
0:23:34 I’m a make it happen kind of person in work and in life. I also know that that can come off as aggressive
0:23:37 or assertive. How do you deal with that?
0:23:42 That’s interesting. So what’s a scenario that you feel like could come across the wrong way?
0:23:47 Well, make it happen is like you have a great first date or something and then you’re instantly like on
0:23:52 to the next day. You know, you’re like, I want to see you again. How about tomorrow? And then the other
0:23:57 person, I don’t know, like, I feel like we’re just in a society now where, you know, you’re supposed to
0:24:03 wait till tomorrow almost. And I hate personally waiting. I’m sure there’s other people out there like
0:24:08 me too. Or it’s like, no, you’re in charge. You have agency and you can make the world happen.
0:24:13 I love this question because I think it speaks to a really real phenomenon where people are
0:24:17 experiencing excitement about somebody, but they feel like they need to hold it back to seem cool.
0:24:23 And so I love to talk to people about attachment theory. Has that come up on your podcast?
0:24:24 No, let’s go into it.
0:24:28 Okay. So attachment theory is something in the world of relationship science that’s truly
0:24:35 backed by the research. It’s something that first came about around 60 years ago with someone named
0:24:40 John Bowlby. And this research was originally done with children to see their attachments to their
0:24:46 primary caregiver. But now we have an entire field of adult attachments specifically around relationships.
0:24:53 And so there are people who are anxiously attached. What happens for them is their story of love is that
0:25:00 I’m going to chase you. I have to convince you to like me. You might pull away. And we’re going to
0:25:05 have this chase dynamic. And that I’m constantly worried that you’re not going to be interested in
0:25:09 me and you’re going to disappear. So how those people show up in relationships, and I know because I
0:25:14 really was one of these daters, is if you don’t hear back from somebody, you start spiraling. They met
0:25:18 somebody else. They don’t like me anymore. You send a bunch of texts to try to reconnect with them.
0:25:23 And you’re often just in this danger zone where you’re not being the person that you want to be
0:25:27 because you’re trying to have this reconnection moment. You think somebody is going to pull away.
0:25:32 Then there’s people who are avoidant attached. They sort of have the opposite experience.
0:25:36 Their version of love is, I’m going to be smothered. I’m going to lose my independence.
0:25:42 And when they get too close to somebody, they are the ones pulling away. So they’re the ones,
0:25:46 you know, great sleepover on a Saturday night. Sunday morning, they wake up,
0:25:50 the person hasn’t left. And they’re like, damn, should I call her an Uber?
0:25:50 Oh my God, that’s me.
0:25:51 That’s you?
0:25:52 Yeah.
0:25:54 You have that feeling of like, I need my space.
0:25:59 Well, I need my space and I don’t want to get hurt. There’s like an element of vulnerability.
0:26:03 Absolutely. What you’re talking about is complete true. It’s not that those people
0:26:07 don’t want to be in intimate connection. It’s that the fear of being smothered or the fear of being
0:26:13 hurt causes them to pull away. I’m going to reject you before you reject me. And so for those
0:26:19 avoidant attached people who think that they’re going to be smothered and then for the anxiously
0:26:23 attached people who think they’re going to be abandoned, what ends up happening is they often
0:26:28 date each other and they reinforce this idea. So I think that love is a chase. You think that love
0:26:33 is being smothered. So when I go after you, you pull away. That reinforces mine and that reinforces
0:26:38 yours. And anxious, attached and avoidant people keep dating each other in this anxious avoidant loop
0:26:44 that leaves both people feeling pretty unhappy. But there’s a third type of securely attached
0:26:50 people. And these are people who have a healthy relationship with independence and with intimacy.
0:26:56 I want to be close to you, but I also respect and need my alone time. And so often the way that people
0:27:02 get out of the anxious avoidant loop is they either become more secure themselves or they date someone
0:27:08 who’s secure. And so that’s what happened for me after, you know, 10 years of chasing after different
0:27:13 people, being rejected, being disappointed, thinking, well, if only I could prove my value,
0:27:18 then this guy would like me. Instead, when I dated somebody who was secure, it broke a lot of those
0:27:25 patterns. And we formed what I feel like is my first really healthy relationship. What happens is 50 percent
0:27:29 of the population is secure, which sounds like a good thing. But those people are so good at being in
0:27:33 relationships that they often get snatched up and you have the anxious avoidant people dating each
0:27:38 other. But in the example that you described, it can actually be very secure for somebody to follow
0:27:43 up after a date and say, hey, I really enjoyed getting to know you. I’d love to see you again.
0:27:50 When are you free? And in that moment, somebody who’s used to dating somebody who’s avoidant might be
0:27:54 like, whoa, they’re coming on too strong or that’s so obvious. They’re so obviously interested.
0:28:01 that’s boring. But a ton of the work that I do is training people to identify secure partners and to
0:28:07 reestablish them in their heads, not as boring, but as secure and to know that those are the people
0:28:13 to go after. So sometimes that person who pulls away is exciting, that sparky feeling because you
0:28:18 don’t know if they like you or not. But instead, really honoring the person who says, I like you,
0:28:23 I’m interested. When can I see you again? And so the slight tweak that I would have to yours is
0:28:29 not I like you. Can I see you tomorrow? That does kind of feel a little bit intense. But being clear
0:28:33 about like, hey, that was a really great date. I feel like we really connected. I’d love to see you
0:28:40 again. And then like working together to come up with the next date. And a lot of dating that people
0:28:46 miss is that it’s about matching somebody’s momentum and matching somebody’s speed. So it’s a dance where
0:28:51 I take a step forward and then you need to take a step forward. If I take 10 steps forward, you might
0:28:57 feel overwhelmed and take a step back. So just paying attention to are you always the one reaching out? Are
0:29:02 you always the one making plans? There needs to be momentum matching for the speed to feel right to
0:29:08 both people? Well, I think the big thing about preparation and successes is the price has to be
0:29:15 paid in advance. You have to put in the work before you get any results. So there’s no way to honestly
0:29:23 know how good your preparation is or isn’t. That’s why I always try to emphasize keep preparing, keep
0:29:28 working. You don’t know what the other guy’s doing. He might be, you know, working just as hard as you
0:29:33 are. And that preparation, you know, it can’t be after the fact of like, oh, I wish I would have studied
0:29:41 more. It’s too late at that point. You have to do it on the front end. So getting in condition, you know,
0:29:47 studying, preparing on your film and your opponents and all that, like those things are all have to be done
0:29:52 on the front end. And, you know, a lot of times there’s, I would say, a little bit of a tendency to just sort of
0:29:57 let up on the preparation. Well, I’ve watched some film. Well, I’ve done some extra sprints. Well, I’ve done this.
0:30:04 I’ve done that. Well, is that enough? You know, is it really enough? And if you do more, will it make
0:30:11 a difference? Not to the point of diminishing returns, but to the point of, you know, comprehensive
0:30:18 preparation. So that’s really what we try to try to emphasize on that.
0:30:24 The way that I think of it, that is sort of that, you know, the pain of losing is sharp, but it’s over
0:30:29 fairly quickly, but the pain of regret, not putting in the work, not doing the things you didn’t leave
0:30:35 it all in the field that lasts forever. Exactly. That’s exactly it. The pain of regret is much more
0:30:42 than, than the pain of preparation. Absolutely. I think you had a 24 hour rule sort of after winner
0:30:46 losses, you have 24 hours to think about it and then you’re, you move on. Is that…
0:30:51 That’s right. Yeah. You play the game, you go back, you analyze it. You, what do we do well?
0:30:55 What do we do poorly? What do we need to do better? What adjustments should we have made? What coaching
0:31:01 errors did we make? And so forth. And, and then you, you factor all that into, you know, how does that
0:31:06 affect this next week? Sometimes there’s a lot of carryover. Sometimes the play team you play the
0:31:12 following week is completely different. And some of those lessons may not really become applicable for a
0:31:16 week or two weeks or three weeks until you see a, you know, a similar type of opponent,
0:31:21 say like a scrambling quarterback, you know, maybe you play two or three weeks where those quarterbacks
0:31:26 aren’t too mobile. And then when you get up against another scrambling quarterback, you go back and look
0:31:32 at a, how, you know, how, how do we need to, to handle this better against this type of an opponent?
0:31:39 So, but yeah, you look at all those things after 24 hours, win or lose or draw, you, you take your
0:31:45 lessons and, and you decide how you’re going to incorporate any of those things into this week’s
0:31:50 preparation and practice, uh, what we’re going to do differently, or maybe do more of, or do less of
0:31:56 whatever it is. Um, and then you’re done with that and you move on to your opponent and, and spend the
0:32:03 next, uh, five days, six days, whatever it is of just, you know, digging in on that opponent and,
0:32:03 and what they do.
0:32:09 Talk to me about the relationship between the best talent in the world. And, you know,
0:32:13 you’re playing in the NFL, you’re coaching in the NFL and confidence.
0:32:20 Well, again, it’s all relative, you know, Shane, I mean, as good as, um, as good as, as the players
0:32:26 are in the NFL, um, the guys on the other side of the ball are pretty good too. And, uh, you know,
0:32:33 I’d say every team, generally speaking, every team has about, you know, five or six players that
0:32:39 are elite, have elite payments, elite contracts. Uh, and then you might have some younger players in
0:32:45 their first through fourth year, you know, two or three, four, whatever those that are elite players
0:32:50 that just haven’t hit those top contracts yet. Um, but they don’t necessarily match up in the same
0:32:54 position. You might have a tackle. I might have a guard. You might have a linebacker. I might have a,
0:33:03 a corner and so forth. Um, so, um, the way those elite players match up is, is very, um, specific
0:33:09 from game to game and how you want to match them, your, your matches against theirs and how you want
0:33:14 to deal with that is, you know, that’s a big part of it. I think the confidence thing is really,
0:33:21 um, interesting. I think what really separates the great players, um, is their ability to do it
0:33:26 even when the bullseye is on their back every week. Um, like it was with Tom Brady, like it was
0:33:31 with Lawrence Taylor, like it is with Patrick Mahomes, um, like it is with, you know, players
0:33:36 like that Lamar Jackson and so forth. Every week, the, the teams are geared towards stopping those
0:33:41 players and game planning against them or putting their best guy on them or, or however you’re going
0:33:47 to handle them. And for those players to continue to be productive, um, in spite of the game plan
0:33:52 of attention they get is, is what truly makes those players, you know, great and elite. And I,
0:33:59 I think that, um, you know, when we had Kobe Bryant come in and talk to our team, I think it was around
0:34:06 eight, 2018, 19, somewhere in there. And, you know, Kobe talked a lot about evolving, you know,
0:34:13 and he said, um, you know, look at when I was 22, 23, you know, I could just get the ball and drive
0:34:20 by anybody and, and score. And he said, I can’t do that anymore. I still score, but I found different
0:34:27 ways to score moving without the ball, jump shots and, you know, being better in pick situations and all
0:34:34 those kinds of things. Um, that, you know, he said, I found, I found ways to evolve my game, um, because
0:34:40 I just couldn’t do the things I used to be able to do as well. Um, but there are other things I found
0:34:46 that I can actually do better. And I thought that was a great message for all of us to hear that as we,
0:34:52 um, you know, as, as we go through our careers, do the things that are working, do the things that
0:34:57 you can do well, but also evolve, continue to learn, continue to, you know, find ways to, to be
0:35:04 productive that are maybe a little out of your comfort zone or, um, are not, um, you know, habitual
0:35:11 for you now, but if you can become good at them, um, they can be great, you know, great tools for you.
0:35:17 Are there any other people that you brought to speak from sort of different sports that sort of had,
0:35:22 uh, a different message that resonated with you or the team and just stands out in your mind?
0:35:27 Oh yeah. We had a lot of them. Yeah. We had a lot of them. And, and, and it was great because,
0:35:31 you know, just the guys, you know, they hear a lot of football stories, but it’s good to hear all the
0:35:36 ones, uh, one of the ones I thought was particularly entertaining. A couple of them, one was, uh,
0:35:44 Paul Asiante. They won like 14 national championships in a row. They won like 160 some games in a row,
0:35:50 matches in a row. I mean, and at the Patriots, we were favored in almost every game, you know,
0:35:56 not every game, but most every game for quite a while. And so, you know, I brought coach Asiante
0:36:02 and I said, you know, here’s a guy that’s won like 13 straight national championships. They won 160
0:36:09 some matches in a row. I mean, you talk about being favored now, like they’re favored and, and, and like,
0:36:13 let’s listen to what that’s really like. And he was great. He talked about it. It doesn’t matter
0:36:17 whether you are or aren’t, or how many you have or haven’t won every day is an opportunity.
0:36:22 You make the most out of each day and you just get better each day. And you don’t worry about what
0:36:26 you’ve done in the past. You just, you look at today’s opportunity and make the most out of it.
0:36:31 It was great. So one of our coach, one of our players sticks his hand up and said, Hey coach,
0:36:35 I have a question. What’s squash? I thought it was a vegetable.
0:36:42 Jimmy Johnson, you know, we were going into the playoffs and Jimmy came up and he was doing a,
0:36:47 um, uh, you know, a story on somebody. And I said, Hey, would you mind, you know, talking to teams?
0:36:52 Sure. So he said, yeah, let me tell you a little playoff story here. You know, when I was in Dallas,
0:36:57 we were getting ready for the playoffs and we were in a special teams meeting. I’m standing in the back
0:37:02 and I see, I see one of our, one of our players back there kind of dozing off and not paying
0:37:06 attention. And he said, he wasn’t a, he wasn’t a starter, but he played in special teams.
0:37:11 And he said, it just really annoyed me. And so I went over, I flipped on the lights,
0:37:15 turned the lights on at meeting. And I went over to him. I said, that’s it. You fall asleep in this
0:37:21 meeting. Uh, we don’t want you. This is your primary job. You take your playbook and, and go see the
0:37:26 job manager. You’re done. You’re cut. And everybody like, Whoa, you know, that woke everybody up.
0:37:32 And, you know, it was right before the playoffs. So, you know, any questions? Um, yeah, coach.
0:37:39 Um, what would you have done if that had been Troy Aikman? Jimmy said, well, I wouldn’t have
0:37:43 turned on the lights. I probably would have gone over to him and nudged him and said like, Hey,
0:37:52 Troy, pay attention. And the message was, if you have a lot of pelts on the wall, you might have a little
0:37:59 more slack. If you don’t have a lot of pelts on the wall, you don’t have any room. You don’t have
0:38:05 any room. You can’t live on what you’ve done. Cause you haven’t done enough. You better know where you
0:38:12 are. And until if you’re Troy Aikman and Tom Brady, you, you go, but he goes, those guys would never do
0:38:17 that anyway, but you, that you might be able to survive that. But if you, if you don’t have that
0:38:23 kind of resume, you haven’t had that kind of production for this team. So nobody wants that.
0:38:28 You’re replaceable. They’ll find somebody else who will stay awake in the meetings and who will be
0:38:33 more attentive. And, uh, it was pretty funny. I’d just nudge him and say, Hey, pay attention.
0:38:39 As a leader, you’ve called yourself blunt and direct when delivering a message to people.
0:38:43 I’m curious what you’ve learned about delivering a message that gets heard.
0:38:49 You know, it’s a evolving process, if you want to call it that. Sometimes you, people did deliver
0:38:57 messages that are not heard because you haven’t really delivered the message clearly. People
0:39:01 actually come out of performance of praise and say, I think I’m doing a good job. And you’re going,
0:39:06 Oh my God, I hope that’s not what you heard. You’re saying to yourself, because this person was supposed
0:39:12 to have told you the three or four things, areas that you’re supposed to improve upon. And the three
0:39:17 or four things that you did wrong, you’re supposed to have gotten very direct feedback. People don’t
0:39:23 like conflict. People don’t like to deal with issues directly. They like to beat around the bush and
0:39:28 then leave saying, I think I give the person the message. I had the opposite perspective, which is
0:39:34 give the message, do it in a supportive way and make sure that whatever you tell them they have to work
0:39:41 on, you help them get to that. So I chose to write performance appraisals, which said, this is what
0:39:48 you’ve done well. This is where I think you didn’t do well. This is what you need to work on. And if you
0:39:54 were to work on these issues and show progress, this is where you could go. So you see what this letter
0:40:01 did was celebrate them for what they did well, told them what they didn’t do well, told them the three
0:40:07 or four things they had to demonstrate progress on in the next year and how I was going to help them.
0:40:13 And then also told them, if you showed progress, this is your trajectory. Because if we don’t do it,
0:40:15 I think we’re not getting the best out of people.
0:40:17 There’s a kindness and clarity.
0:40:23 Toughness, kindness and clarity, all three. But don’t forget the toughness, because you’re
0:40:28 confronting them and saying, you know, I asked you to really get to know the international markets.
0:40:33 You made two trips internationally last year. And each trip in three days, you came right back.
0:40:39 How could you have learned international markets without getting out of the office in the U.S.?
0:40:43 Okay. And then you write saying, I’d like you to visit the following countries next year.
0:40:47 And when you visit those countries, make sure you go down to this level of detail.
0:40:51 You know, some people would say a CEO shouldn’t be getting to that level of detail.
0:40:57 Yeah, they’re right. But if I truly care about this executive and I think they have great potential,
0:41:03 I will get to that level of detail. And I will monitor it middle of the year and say, hey,
0:41:08 did you make any international trips? Did you follow anything I said? And then they say, nah,
0:41:12 I really don’t want to go. Then you go there. You know, you don’t have the potential to be a CEO.
0:41:18 From the outside, we hear these stories about how CEOs pay attention to the top 50 of the top 100.
0:41:23 How many people inside were you really monitoring and trying to develop and having a personal,
0:41:28 a real one-to-one personal relationship where you’re doing this and you’re in the weeds and you’re in the
0:41:30 performance report and you’re trying to build them?
0:41:36 I think there’s about 300 or 400 that were corporate assets. And one watched them all the time because
0:41:41 these are people who in 15 years could be CEO. There’s something about them that, you know,
0:41:47 you sort of caught your fancy when you were in a meeting or in some project that they were on,
0:41:53 they had brilliant ideas. Not brilliant ideas that reinforced your thinking. Brilliant ideas that
0:41:57 challenged your thinking and took us to a better place. Because you don’t want yes people around you.
0:42:02 You want people who say, why don’t we push the boundaries of our thinking? Why don’t we
0:42:08 approach this creatively? And people who put the company before themselves. I look for that all
0:42:16 the time. And so there were 300 or 400 people that we actually called them corporate assets and we
0:42:21 tracked them to make sure that we game plan them, give them the right assignments. And even if they
0:42:27 couldn’t move, could we give them interesting assignments so that they could get the experiences
0:42:31 without constantly moving? So that’s the number of people that we tracked.
0:42:35 What were the signs that somebody was putting the company ahead of themselves?
0:42:41 They would put their hand up for difficult assignments. And if something went wrong,
0:42:45 they didn’t look for somebody else to blame. They would take the blame and say, hey, you know,
0:42:49 I could have done a different job or I could have led differently or I could have staffed my team
0:42:57 differently. These are people who would come to me and say, you know, whatever’s going on in this other
0:43:04 part of the company, I think may be putting something in jeopardy. And I’m not throwing them under the bus.
0:43:10 Would it be okay with you if I went and worked with them to perhaps write things? And I’d say,
0:43:15 be careful how you do it, but go for it. And I will tell them that I didn’t send you there,
0:43:20 that you were doing it out of your own good nature. Otherwise, people say, oh, the CEO’s got
0:43:25 some pets that she’s sending our way. So you’ve got to be very careful how you deal with organizational
0:43:30 dynamics. But these are people who look around themselves and are constantly looking for ways
0:43:35 to improve the company as opposed to how do I get the next promotion, the next raise.
0:43:39 You said a lot of people don’t read the footnotes or the financial statements.
0:43:44 Is that changing in a world of AI where you can sort of like download the financial statement,
0:43:46 pop it into AI and say, what do I need to know?
0:43:52 I think it’s actually exacerbating the situation.
0:43:53 Oh, spend a few beats on that.
0:44:00 Because now, read the financial statements, Anthony, I just put it into AI. I asked ChatGPT
0:44:06 to tell me, what about this? Look for that, look for that. And there’s all the instances of those
0:44:11 things. And then I just read it and it’s all there. Well, did the AI miss it? Did the AI
0:44:19 understand the linkages between each of those sightings? If I’m looking at, for example, I was
0:44:26 looking at a company recently and I was looking at, it was capitalizing costs. Okay. This is a REIT.
0:44:31 And if it capitalizes costs versus putting them through the income statement, if it goes through
0:44:36 the income statement, it makes their operating earnings look poor, lower, and their net EPS
0:44:41 ultimately. But if they put it on the balance sheet, well, you know, that’s an investment in the
0:44:47 future and everything looks okay. Right. And so there’s a gray area. Was it an operating expense
0:44:53 or was it a capital item? And so I was, first thing I looked for was capitalized interest. And so it gave
0:45:00 me all the quotes and then capitalized costs and gave me all the quotes. So then you think that that’s
0:45:05 enough, but you have to then, and I, and I was showing one of my guys, this is a, so then let’s
0:45:10 go to the income that let’s actually pull up the statements where it told us to go. Cause AI made it
0:45:16 faster. I now no longer needed to flip the 300 pages, but it, it gave me where to go. So now I
0:45:22 went there and now I could say, well, that means if that is what’s happened, then we need to look at
0:45:27 this other note to see what, you know, the implications of that. And then we got to look at the cashflow
0:45:33 statement to see how it’s actually impacting what ends up being reported as cashflow. And so those
0:45:40 linkages come, it, the AI makes me get to the answer perhaps more quickly, but it’s my, if I
0:45:48 don’t already know where I want to go, then AI just gives me information. But that information doesn’t
0:45:54 help my decision. If I didn’t start with where I want to get to. And it sounds like that information
0:45:58 doesn’t help your decision. If you don’t know the second, third, fourth order consequence.
0:46:02 A hundred percent. This is, I love it. If that’s where investors go and that’s where they’re going,
0:46:10 everything’s going to AI. The, the bottom level of being an analyst, the junior analyst is going to be
0:46:14 replaced by an AI. The one that said, find me all the references of, you know, where the company
0:46:23 capitalized costs that the AI can do. I get it, but you need someone with experience to know what,
0:46:30 which of those references matter and to what that means to the business. And this brings about a
0:46:36 number of challenges because, well, if that junior person doesn’t learn, doesn’t get on the in on the
0:46:40 ground floor, they’ll never learn to be able to make all those connections.
0:46:44 And the only way to learn is sort of like being in the weeds and not being in AI.
0:46:50 Yes. In fact, it ties to so many things. I, I, with my own children, I’ve seen growing up
0:46:56 when we went to school and we were in elementary school, we would be, you know, we’d have to do
0:47:01 the math tables and, and recite them. Yeah. Two times two is four and so on. I remember I was
0:47:07 struggled with my, with my nine times table and then my 12 times table. And so I had to memorize them
0:47:12 and get them going. But then my children came along and they were using a calculator and apparently
0:47:18 that was okay. I went bananas. I said, you’re not going to use the calculator. You need to learn it
0:47:23 without the calculator. And then you can use the calculator, which is the same with the AI. You need
0:47:29 to understand how the financial statements are prepared, understand the linkages, develop mental
0:47:35 models so that when the AI gives you information, you can, you can digest it and make decisions.
0:47:40 Reminds me of this funny story. When I started university, uh, I ended up in first year calculus
0:47:48 and for whatever reason, the professor who was supposed to teach that class couldn’t teach it. So the dean
0:47:55 of the math department took over and on the first class in the first like minute, he said,
0:48:02 there’ll be no calculators in this class. Oh, nobody of course listened to him because graphing
0:48:06 calculator. You’re like, Oh my God, this makes my life so much easier. We show up to the final exam,
0:48:13 which is like, I think 80% of your final mark. Yeah. And on the front page, it’s no calculators.
0:48:19 And he did not grade that on a curve and it was not pretty for most students.
0:48:27 I taught at university for about, uh, 14 years at York and, uh, truly one of a very fulfilling time,
0:48:33 uh, in my life. And, uh, I still love doing guest lectures. I remember I, I would always start to,
0:48:39 you know, I would go over the outline and I, and I would tell the students, I said, so assignments are
0:48:48 due at the beginning of class. If they’re handed in after the 8:30 start time, it’s a zero. It’s a zero.
0:48:55 And invariably at some, whether it was the first and usually the first or second assignment,
0:49:01 somebody would show up and hand it in late. And I would say it’s a zero and they would whine and say,
0:49:06 it’s, well, how can you do that? And you’re so draconian. And I said, well, you think in the real
0:49:14 world when an RFP is required and you’ve signed with the contract with a client that they demand the
0:49:19 report by 9:00 AM on Monday and you show up at nine Oh five. How’s that look?
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0:50:24 by cooperators, life insurance company. And somehow it’s okay. So it wasn’t okay in my class.
0:50:29 And, and ultimately I think you, you build respect because people see that there’s a rule and it’s
0:50:35 followed and then people have respect for the rule. There’s this sort of like weird dichotomy,
0:50:39 I think with students right now, and dichotomy is probably not the right word. There’s this weird
0:50:46 path where students are coming out and they’re more powerful and capable than ever because they use AI
0:50:52 by default. And so they can get more output than somebody who’s maybe been in their career 15,
0:50:58 20 years. And I use my 14 year old as an example, you know, in a world where he never had to show up to
0:51:05 work, he’s a mid-level employee at most companies based on output. If you never saw him, he can give you
0:51:10 the, the exact same output that a mid-level employee is going to give you if everything goes right.
0:51:17 But the minute something goes wrong, he doesn’t quite understand all the nuances and all the,
0:51:23 and AI, the, I guess the race for him is like, well, AI catch up quicker, you know, because he uses AI by
0:51:29 default. And I sort of think about this as like making a recipe, right? Like if I pull out a cookbook
0:51:34 and I make a recipe and I do everything perfectly, you wouldn’t be able to tell the difference between
0:51:38 me and the chef, like the food, maybe it’s not plated as well, but it’s going to taste great.
0:51:43 It’s going to taste the same. You’d be like, this is amazing. But if something goes wrong, if the oven’s
0:51:49 too hot, if I don’t stir enough, I don’t put enough salt in, I don’t know why it didn’t go right.
0:51:55 But the minute a chef, the chef who created that recipe, who’s got all the experience, who did the,
0:52:01 you know, who’s made it hundreds of times, they taste it and they’re like, oh, your oven said 375,
0:52:08 but it’s actually 350. You stirred this too much. You let this boil. You, they instantly know what went
0:52:15 wrong. And I wonder if in a world of AI, that’s the nuance. And I was talking to Steve Schwartzman about
0:52:21 this in a different context, but he basically said, you know, a lot of the analysts coming up,
0:52:28 they know the numbers, but they don’t know what the numbers mean. Correct. Experience teaches you judgment.
0:52:33 And you talk about this in your book. It’s all about the mental models. I believe that strongly.
0:52:38 The experience teaches you what the numbers mean, as we’ve spoken about. And when you have experience,
0:52:46 you say, I’ve seen that before. And a lot of the things I see happening today link back to things
0:52:53 I’ve seen when I started my career over the last 30 years. And I think that’s something that the AI
0:52:59 can’t quite do unless you tell it where to look, because it doesn’t know the link that I’m thinking
0:53:06 about. Right. But if I, if I can make the initial stage, it can help me get there quicker and more
0:53:11 accurately. But if I don’t, if I don’t already have a model of what I’m looking for, it’s not going to
0:53:16 get there. So you use the word trust. And I’m wondering, is there a nuance with likability?
0:53:21 Because I had heard before, I don’t know where I got this from, but I remember reading something about
0:53:26 like we’re more convinced by people we like and use the word trust. And I’m wondering if that was
0:53:33 conscious. We’re more convinced by people we like and we like people that we trust. Okay.
0:53:39 So they are related. It is, it is possible to believe someone you don’t like, right? It is like
0:53:44 picture someone that you really dislike and they say they’re going to do something, but you immediately
0:53:48 believe that they’re going to do it. So let’s say that there’s some foreign adversary who makes a threat
0:53:52 and you believe that they’ll follow through on their threat because they usually do. Even if you
0:53:57 don’t like them, that is possible. But there definitely is a link between if you like someone,
0:54:01 you’re more likely to believe them. And if you, if you believe someone, you’re more likely to like them.
0:54:07 And I think that liking is actually really underrated. So have you heard of the affect heuristic?
0:54:11 Yeah. It’s, you know, we have different decision-making heuristics. We have mental shortcuts
0:54:15 because we don’t have all the time in the world. This is like an evolutionary thing that
0:54:20 everybody has this. We don’t train it. It just, it just comes with us, you know, out of the box.
0:54:24 We don’t have all the time in the world to take in every single piece of information and make a
0:54:30 decision all the time. Sometimes it’s like, if you see smoke, you just got to go. Right. And so we make,
0:54:37 um, we take mental shortcuts all the time. And one of the big mental shortcuts is if we like something
0:54:42 and feel comfortable with something, it’s more likely to be real. Someone we like is more likely
0:54:47 to be competent. Someone we like is more likely to be smart. All these things just kind of go together.
0:54:53 And so liking is at the center of that. You mentioned that we can engineer trust. How do we do that?
0:55:00 One is repeated exposure. So in order to trust somebody, first, you have to have a sense of who
0:55:05 they are. You wouldn’t trust a stranger. You wouldn’t trust a mystery man. So one is you have to know
0:55:13 who, who are they? They have to show up enough for you get us, for you to get a sense of you actually
0:55:18 know them and they’re not a total stranger to you. It’s hard to trust a stranger, but it’s easy to trust
0:55:22 even a stranger that you have a parasocial relationship with because they’re not a stranger. There are people
0:55:29 that you’ve never met in your life who would trust you because to them, you’re not a stranger. So
0:55:36 first is just become not a stranger. Second is establish a set of shared values. I wouldn’t
0:55:42 necessarily trust your opinion on a restaurant unless I knew that you and I like the same type of food.
0:55:48 So if you are like a vegan that hates spicy food and whatever, I probably wouldn’t take your restaurant
0:55:56 recommendation, even if I like you as a person. Right. So you have to establish some shared baseline
0:56:01 of values. Here are some core things that I believe about the world. And if you share them,
0:56:08 then listen to what I have to say next. If you don’t share them, that’s okay. Right. Not everybody
0:56:13 has to show them. So they have to get a sense of who you are and you’re not a stranger. And they have to
0:56:18 get a sense of how you think and how you view things such that when you say other things, they
0:56:24 already have ingrained in their mind that they think like you think. And therefore, if you believe this
0:56:29 thing, they’re more likely to believe that thing too. This is how to resolve a debate or an argument,
0:56:35 by the way. The better way to argue, and you see really smooth people like Gavin Newsom does this on
0:56:39 his podcast, maybe a little bit too slick, but he’s clearly very good at it, is he’ll have somebody
0:56:45 who totally disagree with him on a bunch of things. And he’ll always make sure to start
0:56:50 with agreeing with them on something. Even if it’s trivial, I agree with you that that thing was totally
0:56:57 insane. And now we can have a productive conversation because we’ve established that it’s even possible for
0:57:01 you and me to see things the same way, as opposed to your knee-jerk assumption that it wouldn’t be
0:57:06 possible. I wonder if that’s why someone is almost never disagree with you when you are like, oh, I taste
0:57:12 whatever in this wine. They’re like, possibly. Or, you know, like in their head, they’re like,
0:57:17 no way. Like that’s a completely different taste. But they never actually come out and say no. They
0:57:23 always sort of like bridge a little bit of a gap. And then they’ll like direct you or steer you towards
0:57:30 what they want you to notice. That’s interesting. I’m a teetotaler. So I’m the person that if I sniff
0:57:36 a wine, I’m like, I think it’s wine. But what I had noticed, which is related to this, is do you ever
0:57:45 see online when people are insulting someone or dunking on someone, but then that person shows up
0:57:51 and says, thanks for your feedback? The original person who was insulting them or dunking on them
0:57:57 almost immediately folds like a cheap suit. Have you seen this? Yeah. Almost immediately they fold.
0:58:02 Hey man, thank you. No, totally understand. I would be doing the same thing. I got you. We’re like,
0:58:09 what just happened? And it’s because once you’re actually confronted by a person, instead of just
0:58:17 like a concept or some kind of nebulous idea of a person or some representation of a person, like once the
0:58:22 person is there talking to you, even if it’s online, we behave in a completely different way.
0:58:27 And so one of the things I tell founders to do is just to show up and defend yourself or defend your
0:58:34 people, defend your companies. Sam Altman is really good at this. He defends his employees and it’s very
0:58:42 hard, even as much as with any public figure, people like to dunk and hate and insult. And when he shows up,
0:58:48 a lot of the time you see the person immediately fold because they’re just like flattered or they
0:58:52 don’t want to fight with him directly or something. It’s one of the most powerful things is just to put
0:58:57 a human in their way. I have very high cringe pain tolerance, whatever you want to call it. I have
0:59:02 no issue with that whatsoever. I think that there is this, this gets easier also with age, I find the
0:59:07 older I get, the less I really, I really care about that stuff. But yeah, I think most people are not
0:59:12 willing to look stupid for a period of time. I think the other thing is that I think about this all from the
0:59:18 concept of like entrepreneurship. In my office here in Montreal, Shopify office, I have the original
0:59:24 screen print that Ben Francis used to create Gymshark. It was a gift. It’s a super meaningful gift that he
0:59:30 gave me. I love it. I have it hung up in my office. Part of the reason why it’s up there is because I
0:59:36 think that it’s an amazing gift and Gymshark is this homegrown success story on Shopify. It exemplifies
0:59:40 everything we stand for. It’s incredible. But the other reason I have it up there is because what most
0:59:44 people don’t know is that that was not Ben Francis’s first company. That Ben Francis actually had a bunch
0:59:51 of failed companies before he landed on Gymshark. And I think about this idea of this cost of failure,
0:59:55 not just from entrepreneurship perspective, but in general, you have to basically figure out
1:00:00 with any, anything you’re doing, what is the cost of failure here? The cost of failure is really high.
1:00:05 You really have to think about it. It’s, you have to sort of do a little bit of like the math of,
1:00:09 is the cost of, is, is the benefit of success worth the cost of failure? And sometimes it’s just not.
1:00:15 But I mean, for $39 a month, you can build a store and it’s not a pitch for Shopify, but $39,
1:00:19 you can build a store. If it works below it up. If it doesn’t work, try something else.
1:00:25 There are still too many people that are apprehensive that, that, that don’t want to
1:00:32 put themselves out there because of this fear of failure. And I’ve long believed that,
1:00:38 you know, getting really, really comfortable with being uncomfortable is magic. It’s totally magic.
1:00:42 And I wasn’t always good at that. I don’t think you need to be born with that. I think you can
1:00:50 learn that. I think you can learn resilience, but I don’t, I don’t know anyone that I admire who’s had
1:00:58 success, who has not gone through that period of making kind of looking kind of dumb. I don’t know if
1:01:02 you’ve ever watched the first interview you’ve ever done. Me? Oh God. Yeah. Look at that. I
1:01:07 wouldn’t listen to the first, I think like 20 or 30 of them. I wanted to get a catalog and then I
1:01:13 wanted to listen to them. Sure. And then I went for like a really long run and I started listening to
1:01:17 them and I was like, Oh my God. And it’s like, I should have asked this followup. Why did I phrase
1:01:23 it that way? And, uh, like you, I’m incredibly hard on myself, came back, went through every transcript
1:01:28 and like, I was like, I want to get better at this for everybody else. But yeah, there’s no secrets
1:01:34 to why you’ve been so successful in my, in my view. I’ve known you now for a number of years.
1:01:39 you, you simply out care other people. And I think that out caring thing
1:01:49 supersedes IQ, EQ, raw talent. Double click on that for a second. I think that
1:01:56 I will take someone. It’s the reason why I like entrepreneurs so much that I think entrepreneurs,
1:02:00 the right entrepreneurs, the best entrepreneurs, they just simply out care other people.
1:02:05 They are willing to, if you put two people in a room, um, one person that’s 50% capacity
1:02:08 and another person, a hundred percent capacity, but that a hundred percent capacity person is
1:02:15 just not caring as much as 50%. I think I can help that 50% person get more skill. I’m not
1:02:19 sure I can change their level of ambition. I think you can change ambition, but I think like
1:02:27 sheer innate, deep rooted ambition, uh, which call it care, whatever, whatever nomenclature
1:02:34 you want to use. I think that is a superpower. And it’s also the reason why when I meet someone,
1:02:39 they say, what do you think I should do with my life? I often ask them, what do you, what do you do
1:02:45 for fun? Because often the, what you do for fun question ends up turning into, I really want to be
1:02:49 a fashion designer. And I’m like, you should go be a fashion designer. Even though you’ve ever done it,
1:02:54 you may not have the raw skills. You will learn those skills, but you seem to really care about this
1:02:59 thing. You’re probably going to be good at it. Is there a difference between who cares the most and
1:03:04 who wants it more or the, like, how do you see that nuance? I look at them the same in my view. Um,
1:03:13 usually high care comes from high intent or high, uh, uh, an elevated level of desire to succeed.
1:03:19 I’m trying to teach my kids that right now. I, I spent a lot of, you know, this is kind of weird,
1:03:26 but I kind of wish I had kids pre IPO rather than post IPO. Why? I think
1:03:32 whatever success that I’ve had and success of, of, of things I’ve been involved with,
1:03:39 they are more meaningful to me because obviously I know where I come from. I know how hard it was,
1:03:45 but I also see how Lindsay, how my wife sees my relationship with things that I’ve done in
1:03:54 particular with Shopify. Lindsay has great, a wonderful emotional connection. It’s Shopify for
1:04:00 Lindsay. Even my wife is not just a company. She remembers, you know, those early days. She
1:04:05 remembers those like being on top of Tucker’s marketplace in the Byron market. Uh, the office
1:04:13 stunk like the buffet restaurant and, and struggling. This is pre, pre series eight even. And, and I,
1:04:18 I like that. I love that. She knows that she knows how meaningful is because she’s seen the entire
1:04:25 journey. Um, my, my kids were born in the last eight years or so. They kind of only know our life
1:04:32 being pretty good. Our lives changed post IPO. I don’t think that’s a secret financially. My,
1:04:38 my life changed and, and, and I don’t take it for granted, but I kind of wish they knew what Lindsay
1:04:43 and my first department looked like to not in Ottawa, Canada and how gross it was. It wasn’t
1:04:46 gross because it was dirty. It was just, it was a nice apartment because we couldn’t afford anything
1:04:53 else. And so what I often, what Lindsay often tells me is just like, yeah, the kids didn’t see
1:04:58 that, but, but tell them those stories. And so I do, I tell those kids, I tell my daughters the
1:05:01 stories of those early days and how scary it was. And we didn’t know if it was going to succeed or
1:05:06 not. And, and I want them to see that. I think I don’t want them to think any of this came
1:05:13 simply because it was fate or just kind of happened or, you know, uh, I mean, luck plays a role here,
1:05:23 but this was sheer grit and willpower. And it still is. Um, part of the reason why I like starting
1:05:30 these small pros like Big Shot or Firebelly is I want the kids to see that. I want the kids to see
1:05:36 this thing that, you know, that first episode of Big Shot we did was, it was Charles Bronfman.
1:05:40 It didn’t do very well. I wasn’t very good at it. I wasn’t a good interviewer. I didn’t know what
1:05:46 questions to ask. Dave and I were kind of awkward fumbling along together. And Bailey, my eldest has
1:05:51 sort of memorized most of that episode. And now she watches that. She, they love watching Big Shot.
1:05:54 They also watched the most recent episode, Bobby Kotick, who built Activision Blizzard.
1:06:02 We put that out last week. And, uh, and I love watching her see the difference in style and,
1:06:09 and the articulation because I want her to know that like all the things she wants in her life,
1:06:15 she can have, but it won’t be easy. No one’s going to give it to her and it’s going to kind of suck at
1:06:19 the beginning. Whenever you’re in that moment, when you’re nervous and you really want something,
1:06:24 obviously the best performance comes when you have freedom, but it’s easy to get attached to that
1:06:28 because you’re like thinking, okay, this is really important. And so we get attached to it and have
1:06:33 tension. So what you can do is ask yourself, what do I want more in this moment? To be successful
1:06:40 right here this one time or to get better at these moments? In other words, to master my ego,
1:06:45 to not be so caught up in what people think. So what happens to most people is that they come to
1:06:50 these points in their lives where they’re really uncomfortable. Maybe they’re giving a speech or
1:06:54 playing ping pong in front of a bunch of people. It doesn’t matter what it is. If you’re nervous and
1:06:57 other people are watching, they come to those moments where they’re really uncomfortable and
1:07:02 they back away because they’re too uncomfortable. They’re too afraid of looking foolish in front of
1:07:07 others. Whereas the most successful people, they’re willing to look foolish. They’re willing to make
1:07:12 mistakes. And so I think a lot of people know that, but how do we get there? And so in that moment,
1:07:17 it’s asking, it’s realizing that when I’m the most uncomfortable, that’s the moment that’s the key
1:07:20 for you. And it’s, it’s principle number one for inter-excellence. Everything is here to teach me
1:07:24 and help me. It’s all working for my good. So we’re going to go look for those moments when you’re most
1:07:30 uncomfortable and say, and remind yourself, this is my teacher. And inter-excellence is about expanding
1:07:35 what you believe is possible. There’s three pillars of inter-excellence, belief, freedom, and focus.
1:07:39 To be fully engaged in the moment, have freedom to play like a child and expand what you believe is
1:07:43 possible. To become, to do things you’ve never done and become someone you’ve never been.
1:07:50 And to expand what you believe is possible, kind of that crucial pillar, is we need to find those
1:07:56 moments where we’re uncomfortable. And we need to embrace that moment. And the way we do it is we
1:08:02 understand that the key thing here is not the outcome, but it’s my willingness to be in this moment
1:08:07 and not back away. It doesn’t matter if you fail horribly. You do that 10 times and fail horribly
1:08:12 10 times. Eventually you’re going to get comfortable in those moments and then your skills will be able to
1:08:17 match and break through. But people don’t break through because they come to those moments and
1:08:20 they shy away. I mean, this is, we’ve all done it. I’ve done it way too many times.
1:08:25 What do you struggle with today in relation to that? Anything?
1:08:28 Well, it’s the same thing everyone struggles with. When I come to those moments, I’m like,
1:08:30 oh, I’m so uncomfortable right now. And then sometimes I’ve forgotten.
1:08:35 It’s like I had this conversation with my spiritual mentor, Nick Osborne. And he said,
1:08:41 what God does is he gives you a jacket that’s two sizes too big. And that’s what a loving parent does
1:08:46 when you’re four or five years old. You don’t buy them a jacket that’s perfectly fit because they’re
1:08:50 going to grow out of it too fast. So the parent’s going to buy them a jacket that’s a little bit too
1:08:54 big, right? So they can grow into it. And he said, that’s what God does. He gives you this jacket
1:08:58 that’s too big. And then you put it on and you’re like, whoa, this is not good. This is not right.
1:09:00 This doesn’t feel right. What’s happened? And that’s what I felt so much.
1:09:04 It’s like, okay, this is not, okay, what’s happening? I don’t, I don’t get it. This is
1:09:09 uncomfortable. But God did that intensely. He’s doing that intensely because that’s where you need
1:09:14 to, self-reliance is the biggest problem that I face. And because I’ve got very little power,
1:09:18 I’ve got very little ability. I’ve only seen the world through this little lens that I’ve,
1:09:23 I want to be able to see all of reality. And so to do that, I need to surrender my little power.
1:09:29 Is part of this reframing failure into, there’s no such thing as failure. It’s just,
1:09:31 it’s not a verdict. It’s like data.
1:09:37 Yeah. Redefining success and failure for sure. Like the hall of fame linebacker, Brian Urlacher told
1:09:41 me that I asked him, what is the difference between you and the best performers that you’ve ever in NFL
1:09:47 that you’ve ever competed against? And he said, most NFL players, they make a mistake and they get
1:09:53 tentative. I make a mistake and I don’t get tentative. And so that’s, that’s that courage.
1:09:56 That’s that willingness to fail. That’s that relentlessness that’s needed.
1:10:02 So that’s what happens. I mean, it happens with people too. Like if you give a talk at work and,
1:10:06 you know, it doesn’t go quite right, it’s in your head the next time you do it. So you’re
1:10:11 less likely to be successful in a way, but the counterbalance to that would be, okay, well,
1:10:17 what do we do? We do more preparation. We, you know, we go through our mistake, we reflect on it,
1:10:21 we learn from it, and then we sort of like let go of it and move on. So we don’t make the same mistake
1:10:27 again. Yeah. So failure, that’s all obviously a big part of it. And, you know, and there’s one
1:10:33 of the principles, the presupposition is there’s no failure, only feedback. It’s the emotional part
1:10:39 is, is the, the issue. If there’s no emotional aspect to it, then, then, you know, what does it
1:10:39 matter if you fail?