Inside the Minds of the World’s Top CEOs

In this episode of the Startup CEO Show, host Mark MacLeod shares the findings of a deep dive into the personal habits and leadership traits of eleven founder‑led, market‑leading companies (Airbnb, Canva, Lynda.com, Meta, SpaceX, YouTube, Tesla, Oracle, NVIDIA, Shopify, and Snowflake) whose combined market cap exceeds $6.4 trillion. Drawing on interviews, public data, and his own experience coaching growth‑stage CEOs, MacLeod identifies five core personal habits (sleep, mindfulness, fitness, continuous learning, and intentional downtime) and five recurring leadership traits (relentless focus, direct communication, visionary ambition, customer obsession, and building teams around a founder’s unique super‑power). He emphasizes the outsized role of luck and timing, the power‑law nature of venture outcomes, and the unique challenges of the CEO role (communication‑centric, increasingly isolated, no formal training). The episode also serves as a launch pad for “Limitless,” an exclusive community and coaching program for VC‑backed CEOs designed to help them scale themselves faster than their businesses. Throughout, MacLeod uses vivid anecdotes from each CEO to illustrate the habits and traits, and repeatedly asks listeners whether they are ready to become “limitless.”
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They all question conventional wisdom, right? By definition, if you do what everyone else does, you should expect the same results as everyone else. Nothing should change. They all prioritize speed. They all communicate clearly and often. I tell my CEOs all the time, the bigger your company gets, the more your role is strictly a communications role. And if you don't find you're saying the same things over and over again, you're not speaking enough. Every one of these CEOs recognizes it's a long game, right? Shopify's 21 years in, and so they They prioritize health and they never stop learning. Welcome to the Startup CEO Show. I'm your host, Mark MacLeod. This is episode 75 of the podcast, and so it's a different one. Back on episode 50, it was just me and I shared a bunch of lessons from 25 years in the startup world. And here for episode 75, you're, you're stuck with me again. And on this one, I wanna share with you kind of an insight that's come up recently that has actually become my purpose. And you know, the funny thing is it was my purpose all along, but it's really just all become clear in the last few months. And I've been obsessed by just some key questions, right? Like, why do most CEOs fail? Why do most startup CEOs fail? But some keep going forever, year after year, decade after decade, in some cases, just keep building. What do those leaders do differently that others need to do, right? What could we learn from those CEOs that just keep going year after year? What are their personal habits, right? What are their leadership traits? From a Canadian perspective, there's lots of Canadian listeners and watchers, right? How do we get, I don't know, 10 more Shopifys? These are questions that I think about all the time. I'm guessing probably many of you do as well. Earlier this year, Brian from Turing Fest in Scotland asked me if I would come back again and to give a talk. And as a proud Scotsman, I lived there till I was 11. I will never turn down an invitation to go there. And so I thought about what would make a great talk. And what I came up with was like this notion of limitless leadership, right? How do some leaders keep growing and scaling forever? And what can we learn from them? And thus began a bunch of research and I turned that into a talk., and I'm actually gonna deliver that talk for you today. But you know, really what came out of that, right? I looked at, I think it was 11 companies and they had built collective market cap of like $6.4 trillion, right? Just like staggering. And really went deep on the management practices, personal habits, routines, et cetera, of each of those leaders. But what struck me as I was flying back home from giving that talk was like, this is actually my purpose as a coach is to help CEOs to become limitless, right? To help CEOs always be growing faster than their business. And so this, yeah, this is kind of my purpose, right? And, you know, I'm turning 5, 55, not 5, turning 55 this week and really thinking about, hey, where am I going with myself? What's my purpose? How can I have more impact? You know, I hear from early stage CEOs all the time, you know, looking for coaching and I run the world's least scalable business. And, you know, historically I've only been working with really growth stage CEOs, but this notion, like this purpose or this challenge of making people more limitless and really helping more and more CEOs unlock the limits and just keep building year after year is really, really compelling to me. And so as I thought about that, I kind of needed a different delivery model for my coaching. And so I'm pleased to announce that I am launching a new exclusive community of VC-backed CEOs called Limitless. And the intent here is to curate a group of CEOs who, all of whom have raised capital. It can be at various points in the journey, but people who want to scale themselves and their companies without limits. People who want to build market leaders, but you know, not lose themselves in the process. I talk about this often on the podcast. You know, I've done over a billion in exits and the number one reason why founders choose to sell is because they burnt out. They just can't keep going anymore. And so I've seen that happen over and over again. And I deeply believe that happy, healthy humans build bigger, better companies. And so that's really the purpose of Limitless, uh, is to help CEOs keep going forever, give them the tools, the systems, the support, the peers, all of whom are on that same journey, right? Who want to build market-leading companies but not kill themselves in the process, right? So many CEOs that kind of like the company's happening to them. It's this rollercoaster and they're just like hanging on for dear life, right? And I think there's a better way., and we're gonna find that way together in Limitless. So I'll stop the advertisement, go to limitless.co and check that out. And then without further ado, I'm gonna walk you through the talk that I gave in Turing Fest that actually kind of inspired, uh, the creation of Limitless. And I'll make sure the slides are available somewhere so you can read those later as well. So as mentioned, this whole talk was around limitless leadership, how top leaders keep growing no matter the scale. And, you know, to put this in context, right? The success is not evenly distributed in the startup world, right? If there's like a power law, I mean, you may have heard of a power law of venture capital before, right? Which is where the vast majority of returns from a venture fund are gonna come from a very small number of their companies, right? You know, I used to be a partner in a seed stage fund and the prevailing wisdom was if we did 10 investments, you know, maybe 1 or 2 would be really big winners. 2 or 3 would maybe break even and the rest would be zeros. And I think in reality it's even a bit more polarized than that. And with AI becoming more and more prevalent, I think it's gonna become even more polarized. Still, right? Like Anthropic just raised $13 billion at a $198 billion pre-money, right? Like, you know, these numbers are reasonably unprecedented for private technology companies and kind of that's where we're headed. And so if you've raised venture capital and like, you know, I only coach CEOs that have raised venture or private equity, the focus, focus for Limitless.co is also on, you know, Founders who are on a venture-funded, private equity-funded path, then you've signed up to deliver a really big outcome, right? And an improbable outcome, right? If you read TechCrunch all the time, read BetaKit, you see these different exits. You may think that they're common, but in reality, you know, they're just not that common. That's the reality in which we live, right? Which is as a venture-backed CEO or private equity-backed CEO, You're shooting for an outcome that is, is hard to achieve. And there's a really clear pattern, right? Where the biggest outcomes are actually founder-led start to finish. So 100% correlation between a CEO's performance and the outcome of their company. And so the challenge and opportunity for CEOs is to always be growing faster than their business. And as I mentioned, I, I see that as the purpose of coaching, which is helping them. Stay ahead of the business. But let's talk about that CEO role for a second, right? Like there's no gradual path. Like I was a CFO for 14 years. First of all, I studied a body of knowledge. I'm a CPA. So I started with that and then it was baby steps. I was like a controller, a director of finance, a VP of finance. By the time I was given the CFO chair, I was ready. Many of you here watching or listening, You just started a company and like, now what? Now, hey, you're responsible for everything. You didn't— there isn't a CEO school. You can't get a CEO designation. There's no playbook really, or someone would have written it and I wouldn't have a business. And then, you know, the more success you get, the bigger your company gets, the more kind of everybody wants a piece of you. Now you're dealing with board dynamics. And then, you know, the bigger the company gets, also the kind of lonelier the role gets. And yes, you know, you have a management team, but the difference between you and every other person on your management team is you can fire them and they can't fire you, right? And so super challenging role and one that I'm endlessly fascinated by, and that's why I only coach CEOs. So, you know, I set out in preparation for this Turing Fest talk to look at, you know, some of the most successful leaders. So Toby from Shopify, Jensen from NVIDIA, Elon Musk, some older school examples like Larry Ellison from Oracle, Susan from YouTube, rest in peace, Mark from Meta, and really, you know, just try and dissect it, learn everything I could from them. And, and as I mentioned, so I looked at 11 companies in total, so Airbnb, Slow Snowflake, Meta, SpaceX, Canva, YouTube, Tesla, Oracle, NVIDIA, and another older school example, Lynda.com that LinkedIn bought, and Shopify. And collectively those 11 companies were worth $6.4 trillion. And so what did I learn? You know, that's what we're going to get into that now. One big caveat, right? I cannot overestimate the importance of luck and timing in any outcome, right? You can get everything else right, like amazing team, amazing product, but if you get the timing wrong, you're just not gonna get the outcome right. There were so many companies— I was around for the beginning of the internet and really interesting products were being built and taken to market by great teams., but too many people were like on AOL dial-up modems. Many of you listening might not even know what I'm talking about, but like basically the internet adoption wasn't there. So many companies only took off once there was mobile, right? So like timing's a huge thing and, and luck is a huge thing. So with that caveat, you know, let's get into it. So the first leader I looked at is Brian Chesky, co-founder and CEO of Airbnb. And so we already have this like stereotypical notion with founders, right? Of like, I don't know, bro hustle culture. I'll sleep when I die. Just hustle. I use coffee, sleep at my desk, uh, all of that bullshit. Brian doesn't subscribe to any of that. He deeply prioritizes sleep and energy management. Uh, Brian is actually a night owl. He's, uh, Mornings kind of suck for him and he's most creative in the evenings. And so that's how he manages his schedule. He's not at the office at 9:00 AM. He gets in later, but he stays later. So he's not— he's honoring kind of the natural rhythms of his body and working around that. He has daily mindfulness and reflection practices. He meditates each day. He takes time to reflect, to, to work on his self-awareness, to learn. And of course that requires slowing down, right? Pretty hard to take time to reflect if you're in 10 to 10 hours of back-to-back Zoom calls. He's relentlessly curious. Again, makes time to learn. Many of the CEOs that I've studied here, many of the CEOs that I coach, voracious readers, reading books, listening to podcasts, always learning. And so Brian, Brian's like that, right? And from a cultural perspective, huge customer empathy and just an obsession for the customer experience, right? You know, you look at hotel ratings and we're used to like a 5-star rating. And so he challenged his team to come up with like, what does an 11-star experience look like? Now, we weren't seriously going to implement all the things that would get an 11-star rating., but a really great thought exercise, right? Like, you know, there's no bad answer. Throw out every possibility. It doesn't matter if it's expensive, doesn't matter if it's practical. Like, let's inspire ourselves and think about what an 11-star guest experience looks like. And he's made that kind of a core part of this culture, right? So he leads with culture and values. When people join, they get a memo from him called Don't Fuck Up the Culture. And of course, many of you may have seen that Y Combinator talk recently where Brian talked about founder mode, right? So yes, he does make time for this reflection. He makes time for energy management. He works out. If you see him, he's a pretty jacked guy. He's managing himself and his boundaries, but when he is at work, he's all in and he will go anywhere and everywhere. This is what is meant by founder mode. Founder mode, meaning like, you know, The opposite of founder mode would be, well, I have these people that report to me and if I have an issue, I'll mention it to them and then they'll bring it to their direct reports and so on. There's all these different layers. Founder mode is like, I don't care what the org chart looks like. I'm gonna go wherever I need to go in order to get the answers that I need and solve the problem. And that's how he operates. So he has. A very large number of direct reports. I think it's almost like 50 people that report to him. He doesn't do one-on-one meetings. He's got a very flat organizational structure, but as a result, he moves fast and he's super close to the customer. And so if I were to boil this down into kind of what are Brian's superpowers, it's that relentless empathy. He's just obsessed with the customer experience. And you know, he's a designer by trade, and so they have a designer-driven culture in terms of how they build their experiences. So that's Brian. Next, let's move on to Melanie Perkins, founder and CEO of Canva. Melanie actually burnt out pretty early in the Canva journey, and so learned from that painful lesson and now builds in very purposeful downtime and recharge rituals she walks a lot every day. She meditates every day, talks about having very simple morning rituals. She kind of eases into her day. She'll journal and write and kind of reflect, uh, like Brian, continuous learner. Also somebody who's very humble, uh, right? She doesn't come from Silicon Valley and, you know, she's kind of far removed from all of that. And it was actually pretty hard for her to raise money, which brings up another point that I'll talk about in a minute. Very mission-driven, really, really focused on enabling anyone to create great designs. Their culture is very positive. They talk about having good humans. And so she's got, she, they have lunch together every day. She'll sit and have lunch with individual contributors.. And so she's staying close to them and, you know, they have kind of different systems in place to sniff out anyone who might be a detriment to the positive culture that they're trying to build. And then the big thing, right? She's been at this for some time, is resilience. And she learned this in the process of trying to raise capital, right? She was a single female founder from the other side of the world, and when she went to Silicon Valley to raise money, she was rejected time and time again. I think in total she was rejected over 40 times, but here she is today and she's built a market-beating company worth many, many billions of dollars. And so what are her superpowers? You know, from a product perspective, right? Simplifying the complex. I don't know if you guys have used Photoshop, but I've tried to, and you know, I find the interface really, really difficult to use, but I can figure out how to use Canva. I use it all the time.. So simplifying the complex is definitely a thing. And then just this grit and optimism, right? In the face of all these rejections, all these obstacles, she's a solo founder. She just keeps going. Next, Linda Weimann from Lynda.com. Many of you may not know this. You know, this was an e-learning company that LinkedIn bought for, I think it was $1.5 billion. And she has a lifelong love of learning. She was actually a teacher before doing this. Very grounded. She, she was like the ICP, right? The ideal customer profile for this product, it's her. And so she's basically building for herself, you know, scratching her own itch and, you know, doing a really, really good job of it. As a result, obviously deep customer understanding. From a leadership perspective, not a micromanager, someone who would sort of empower people with a vision. Hey, this is what we're trying to achieve. This is what would really delight our customer. And then giving them space to go and figure out how to make that happen. Right? So kind of a very trusting, very open style of leadership that enabled her to scale and, and leading with integrity and authenticity, right? She was this person. She was just a teacher at heart, and therefore just, you know, enabling learning was just core to, to who she was. Mark Zuckerberg. All right. So there's lots been written about Mark, movie's been made about Mark, so you probably know a ton already. And of course, right, famously, uh, Mark's a Harvard dropout. And has obviously transformed himself many, many times over in the process of building Facebook that has now become Meta. So what are some of the things that he does? He sets yearly personal challenges for himself to grow himself, right? He learned Mandarin one year, set himself like a crazy target for running. He reads, I think it's like a book every 2 weeks or 2 books. It's like a large number. He automated his entire house with robots just to see what was possible. So always kind of pushing himself, always growing. He streamlines decisions. He's changed this a little bit now. He's like a bit more of a hipster look now, but for years, um, he wore the exact same wardrobe, right? The same hoodie, same color t-shirt, same jeans. If I went into his closet, it would have just been like a closet full of the same stuff. Uh, very focused on personal wellness and balance. You may have noticed he's pretty jacked. Perhaps even more so as he was gearing up to fight Elon. I kind of wish that happened. Doing martial arts. So he is very focused on that. He makes time for reflection and self-correction. Same thing with Brian, right? He has this kind of explicit learning loop. Comes from a technical foundation, obviously, and so obsessed with product. And, you know, Facebook famously had this kind of hacker culture. You know, move fast and break things. That's just how, you know, he operates, what he believes. It's a mix of blending like a data-driven decisions with vision, right? So it's kind of coming at direction top-down and bottom-up, right? Like Chamath from Social Plus, right? Was the, the early growth leader there, and that's what kind of pioneered this data-driven decision. Capability, I guess, inside Meta. But then Mark also has huge vision, right? Buying Oculus and what the moves that they're doing now around eyeglasses. You know, these are— nobody's asking for these things, or even just the conviction to pay $17 billion for WhatsApp, which is a company which at the time had no revenue. And I still actually don't think it has revenue. Or paying $1 billion to buy Instagram when I think there were 8 or 12 people at a time at the time. And doing that kind of right before the IPO because he, his intuition told him that this was a threat, you know, making these bold moves, risky moves that have clearly paid off. And, you know, one story that I love to tell, CEOs ask me all the time, Hey, you know, when should I, when should I sell? You know, should I sell my company? When's the right time? And, uh, you know what I tell them is, hey, there's no one right answer. Uh, we have to, you know, you can't A/B test it. And the story I tell them all the time is the story of when Yahoo, rest in peace, wanted to buy, uh, Facebook for a billion dollars. And if he had taken that decision, then the history books would say that he had a big win. He would've returned the fund for Excel. He would've been super rich. It would've been a wild success, but he didn't. And of course they're now worth whatever they're worth, you know, many, many, many billions of dollars. Maybe they're even into the trillions now. I don't know. And so just, you know, again, reinforcing his boldness, right? And the conviction he had, the vision he had, that was a really young company then taking a billion dollars would've been a big deal. A billion's a lot of money. We kind of throw the word billion around these days pretty often, but you know, it would've been a big deal for him to do that. But he didn't. So that's a really big part of his leadership, you know, just having that vision and these, the willingness to make big bold moves. He has a big focus on hiring only the best. You know, he talked about only hiring leaders that he would work for, right? She's no longer there, but Sheryl Sandberg was his chief operating officer for many, many years, and he deeply looked up to her, saw her as a mentor and someone that he would absolutely report to. And then, you know, final thing to say, you know, open communication, very strong, rigorous, direct, and rapid feedback. No layers, no silos, no, you know, I don't know, formal reports, kind of just tying into that hacker culture, you know, very direct and actionable feedback. You know, his superpowers are, you know, that he's got that technical depth as a foundation, but marrying that with, you know, a compelling vision and, you know, big bold bets. There's probably a ton more to be said about Mark, but, you know, Let's move on. This episode is brought to you by Limitless. Limitless is an exclusive community of VC-backed CEOs who want to scale themselves and their companies without limits. The biggest outcomes in the startup world are founder-led. Meta, Amazon, Shopify, Airbnb, Canva, NVIDIA. Behind every one of these companies is a founding CEO who didn't just scale their business, they scaled themselves. Sales. They added one zero at a time and today run companies with billions of dollars in revenue each. That's the goal of Limitless: to give you the tools, strategies, mindset, and community to lead at the highest level without sacrificing your health, relationships, or purpose. Through group calls, an elite peer network, a proprietary AI coaching bot, members-only library, and in-person experiences, Limitless gives its members everything they need to keep scaling themselves and their companies for as long as they want. Go to limitless.ceo to learn more. All right, Jensen Huang, uh, co-founder and CEO of NVIDIA, a company that is in the news very much these days because of their AI chips. I preach balance to my CEOs, right? You know, I don't want them— it's not 9 to 5, you can't be balanced, but I don't want them burning out. Jensen works 7 days a week. He does prioritize, you know, sleep and exercise, but you know, his company is at ground zero of this AI movement and he's in an industry where if you don't keep innovating, you'll become obsolete. Intel's experienced that a couple of times, and so you just have to keep going. So, you know, this dude works 7 days a week. But it's not just kind of letting the job happen to him, right? In endless meetings, he creates time for deep focus and like time blocks. So he's very intentional about how he spends his time. Super transparent communication. He, like Brian Chesky, has over 50 direct reports. He has no one-on-ones. He found— and many of my CEOs say this, by the way, right? Like when I have a one-on-one, I end up saying the same message messages over and over again. And so he's found that, and so everything is a group meeting. What that means sometimes is you're getting pretty harsh feedback in front of a bunch of your peers, right? And so he's built a team that can handle that. Yeah. So that's kind of how he runs the company. He's ruthlessly prioritizing, saying no. Yeah. Radically transparent and really trying to create the dish— conditions for people to do what he calls their life's work, right? He's trying to bring the best people together. The best ideas win. It doesn't matter where you are on the org chart. It doesn't matter your seniority. If you've got the best ideas, that's what we're gonna do. You know, really, really high standards and that shared learning through kind of, like I say, everything happens in a big group environment. And then willing to make, you know, there's a few times in the history where he's made kind of bet the company decisions and they've paid off. He's riding one of those waves right now with the AI chips that they've built. And so if you boil that down into his superpowers, right, prioritizing deep work, he's got stamina. He's figured out how to work 7 days a week and not blow up. Combined with these kind of periodic long-term big bets. All right, Tobi from Shopify. I had the privilege of working with Tobi for a brief moment early in their journey. Another famous dropout. So what does Tobi do? He's continuously learning and adapting. He has no attachment to anything, right? Everything is evaluated through the lens of like first principles and whether they make sense. And if they no longer make sense, he stops doing them. There's a really visible example of that recently, right? They paid $1 billion to acquire a company to get into the logistics space, and so now they're gonna ship product and hold product for customers. Huge decision, right? Spent $1 billion doing it. After doing it, they concluded, you know what, this kind of no longer makes sense. The assumptions we had for doing this no longer hold true. We're not gonna do it. And we're just gonna get outta that business. So many other CEOs would've felt like their identity and their ego were wrapped up in that decision, and it would've been really hard for them to undo it. So I really applaud Toby for just, you know, not letting any of that affect him and just, you know, staying rigorous, staying objective, listening to the data, no sunk costs, and let's just see what that tells us. Toby is deeply technical, one of the original contributors to the Ruby on Rails framework. I had him on the podcast last year and he told me, you know, sometimes he wishes he was the CTO, right? So he just loves product and technology. Now what's interesting there is he's leaned into that. He's the, yes, he's the CEO, he runs the company, but he spends most of his time on product and technology. And so he has designed the CEO role and by extension has designed his leadership around that superpower of his, enabling him to spend all his time there, right? Normally he's publicly traded company. You would expect the CEO to be the person doing the CNBC squawk box and all the quarterly investor relations, but it's Toby's right-hand Harley who does that, right? So that's not a typical way to split up the CEO role. This goes back to his first principles thinking. He's like, This is what I'm best at, is technology and product. This is where I wanna spend my time. Harley, deep extrovert, absolutely amazing storyteller. He's the best possible person to be doing that stuff. So, um, first principles thinking is a thing. Like many of the CEOs, you know, obsessed with solving the problem, right? Making commerce simpler so that anyone with an idea for a product-based business can start and scale., and then building in systems to scale every step of the way. Much more to be said about Toby, but if you boil this down to superpower, it's technical depth with visionary product thinking. All right, next, Frank Slootman from Snowflake. Many of you may have read his book. I thought it was fascinating. So Frank brings, he calls it extreme machine focus to each day. Like every day matters. He's constantly raising standards and speed. He's unapologetic. Apologetic about being unbalanced. He'll work 24/7. And so as a result, he's relentless about talent and culture and eliminating friction or bureaucracy, getting rid of people that he calls passengers, always driving urgency and accountability to get hypergrowth. And his results have been phenomenal. Like, I think this is his third or fourth company where he's just hit escape velocity. So he's got a recipe. He's probably not the easiest guy to work for, but his results speak for themselves. And so if you're to boil this all down to a superpower, it's that relentless focus and execution. All right, Elon. Again, we could do a podcast just on Elon. It still would probably scratch the surface. So Elon, let's set aside all the craziness recently, especially with the political stuff, and focus on his performance as a CEO. All in intensity, right? He's like, I go to sleep, I wake up, I go to sleep, I wake up, I work. You know, I read his biography and of course he's famous for sleeping on the factory floor. So just like intensity, like no one else. Unwavering passion for learning., problem solving and first principles, just like Toby. He literally taught himself rocket science. He literally taught himself, you know, how to build cars and how to build, uh, reusable batteries. Literally the smartest person in the room, right? Sets massively ambitious, seemingly impossible goals, right? Like we're gonna, we're gonna make Humans and interplanetary species, and we're gonna live on Mars. But the funny thing is he does these things that seem impossible and then makes them happen, right? You know, the car industry might be catching up a little bit now, but for years Tesla was further ahead than anyone, even though they were a much younger company. He leads by example. So yes, he sets these standards, but he'll be right there on the factory floor with you. He's working harder than you, right? He's not telling you to work all the time and then going off golfing with his buddies. He's all in completely leading by example. He sees failures as just learning opportunities, right? You think about the cost of a failure of a rocket that didn't work, right? It's not like a piece of code that didn't work. Oh, well, just, I don't know, write a bug fix and upload it and off we go. No, I mean, you blow up a rocket, it's kind of a big deal. He just sees them as learning opportunities. Like several of the CEOs we've talked about here, Brian from Airbnb, Jensen from NVIDIA, he flattens hierarchies.. He wants to go right to whomever has the answer and the person that's closest to the problem. He's willing to make bold sweeping decisions or pivot to invest in the future. I didn't listen to it, but apparently on the most recent earnings call, he talked about the future of Tesla being about robots and not cars, which I'd say is a risky thing for a public company CEO to do because all of the revenue is in cars right now. Unconventional hiring approach, doesn't care about university degrees or anything. He just probes and asks. Really hard questions to figure out who's the smartest person and then hires them. Unfortunately, he views people as expendable, right? Doesn't really care about individual people. He'll churn and burn through people and do whatever it takes to take, to make those impossible goals become possible. Another person that I would not want to work for. So what's his superpower? He's smarter than everyone else and he's relentless and, and, and an optimist, you know, clearly an optimist, right? Like this dreamer who just goes about turning these dreams into reality. All right. We still have a couple of more. I'm going old school this time. Larry Ellison, CEO of Oracle. Larry is in his 70s. If you look at a photo of him, he looks like he's in his 50s. Uh, so huge focus on health so that he can get peak performance. He's fiercely competitive. He's a competitive sailor and he's won what I forget what it's called, but the world's most prestigious sailing competition. I think he's won it a couple of times. He seeks to dominate his industry, uh, makes bold, huge decisions, picks huge fights with his competitors, buys competitors. Um, just fiercely competitive. And combative individual and sees their internal culture as embracing competition as a way of life. That's what he describes it as. Like many CEOs, questions conventional wisdom. And then he is also a CEO with a technical foundation. And so he's very hands-on in product, but he's lighter in other areas. He's had a kind of right-hand person for years, Safra Katz, and gives her room to kind of run everything else., and he goes deep on what he cares about the most. All right. Last but not least, Susan Wojcicki from YouTube. Susan was parachuted in. She was the sponsor within Google that said, hey, we should buy YouTube, you know, very early in their journey. She became their CEO and a big focus on user and community. Lots of time talking to users, getting feedback, sharing direction, kind of a two-way discussion, being very open, big risk taker, buying YouTube. In the first place was a big risk. They paid a ton of money for the company given how much revenue they had then, and it wasn't clear that it would work. And obviously it's worked. It's been a wildly successful acquisition. She's actually a fan— well, she's no longer around, unfortunately. She's passed away, but was a big family person and made huge time for that. She had healthy boundaries between work and family. She had dinner with her family every night. And that forced her to become an extreme delegator, right? The only way she could make those boundaries work is if she really handed off meaningful responsibility to people and had a culture that very focused on openness because she had all these, all these kids, all these family obligations. She had lots of practices to manage her stress and perspective. And yeah, yeah, very open from a communication standpoint. So I just talked a lot and there's so much more that could be said about each of these CEOs. So I've scratched the surface, but if I was to synthesize this down into the top 5 personal habits, and not everyone has them that I've talked about. First is sleep. I tell CEOs all the time, right? Today's performance began last night. Depending on when you went to bed and what was the quality of your sleep. Next is mindfulness, right? As I talked about, many of these CEOs meditate each day, have reflection practices, journal, make time to reflect and learn. And, you know, as a CEO, really your job is to make decisions. And the clearer and more present your mind is, the better decisions you're gonna make. Almost all of these CEOs, maybe the exception is Elon, have prioritized health and fitness. Zuckerberg, uh, could kick my ass. Uh, Toby's a professional race car, uh, driver now. I didn't include Jeff Bezos from Amazon in this list. I could have. Jeff could be a bouncer. Everyone's prioritizing fitness. Everyone without fail. Makes time for learning. They go through explicit learning loops. They make time to read, make time to get whatever external input that they need in order to make the best possible decisions. And most recognize that they need downtime and clear boundaries and a clear kind of psychological gap where I stop thinking about my business for some period of time so I can allow my brain to refresh and then come back at it. And then if I boil down out of all of these leadership traits that we've discussed, what are the top 5 leadership traits that keep showing up? Relentless focus, right? We're not an inch thick and a mile wide. We're doing one thing. We're going super deep, like Facebook, right? Like could have gone broader, but for year, for the first few years, only about Ivy League colleges and then broader colleges. And then it was many, many years before they hit the general population. Huge focus on building the best possible teams that you can. Again, Facebook's a great example of that. Direct communication, right? You know, speed is everything. And one way to promote speed is just to be super direct, A, in what you say, but B, who you say it to. Forget your hierarchy, go wherever you need to go in your org chart to solve the problem and get people moving in the right direction. Every one of these leaders has a huge vision and is working to inspire everyone with that vision and get them moving towards it. And everyone's focused on kind of the customer experience, customer love, et cetera. Yeah, so kind of bringing this down, traits of limitless leaders, right? They're building their role and their company around their unique superpowers. I talked about how Tobi at Shopify does that. They all do that. They're completely in love with the problem. That's the thing that keeps them motivated, keeps them going. They have some relevant technical foundation that doesn't have to be product or technology, right? Like Marc Benioff from Salesforce, his background was in enterprise sales. They're an enterprise sales company. That makes sense. He didn't have to be technical. In that case, that is his technical foundation, but all of them have a relevant technical foundation like Brian From Airbnb, he was a designer, right? They all have high, in the case of Elon, almost impossible standards. They all question conventional wisdom, right? By definition, if you do what everyone else does, you should expect the same results as everyone else. Nothing should change. They all prioritize speed. They all communicate clearly and often. I tell my CEOs all the time, the bigger your company gets, The more your role is strictly a communications role. And if you don't find you're saying the same things over and over again, you're not speaking enough. Every one of these CEOs recognizes it's a long game, right? Shopify's 21 years in, and so they prioritize health and they never stop learning. So my question for you is, are you limitless? Do you want to keep growing year after year after year? And build the Shopify or Meta of your industry? Do you wanna feel like you're always growing faster than your business? You see exactly how you're gonna turn your vision into reality. If so, you got lots to learn from these CEOs. And if so, I definitely invite you to go check out limitless.ceo and become part of our community. Thanks for watching or listening, and we'll see you next episode.
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