Some founders never manage to keep pace with their own company's growth, while a rare few keep leveling up and build generational businesses. In a venture world where roughly nine in ten startups fail and most exits don't even return the capital invested, what actually separates the CEOs who go all the way?
Mark MacLeod, who coaches venture-backed CEOs, studied the personal habits and leadership traits of eleven founders behind trillions in market cap - from Brian Chesky and Toby Lütke to Jensen Huang and Elon Musk. The patterns are strikingly consistent: prioritizing sleep, fitness and relentless learning, building their role around a personal superpower, staying in love with the problem, and driving speed through focus and direct communication.
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Good morning, everyone. It's it's always a true pleasure to be back in Scotland. When you think about the attributes of Scottish people, pride comes to mind. We're very proud of being Scottish. And I don't sound Scottish anymore, but it's always great to be back here.
Today, I wanna talk about what I call limitless leadership. Why is it that, you know, many founders fail, either can't keep up with the growth of their company or can't even create growth in the first place, and yet other CEOs, other founders go all the way and just build these massive generational companies.
What is it that sets them apart? What are their personal habits? What are their leadership philosophies? That's what we're gonna explore today. We've covered this already, but the summary of the introduction is that I'm old. I've been in the venture backed startup world since nineteen ninety nine.
I was here for I was chatting with someone outside before this. You know, I was around for the browser, the Internet, for mobile, for web two dot o. And of all the changes that have happened, actually, AI both excites me and scares me the most.
And it's the first time in my career where I've been like, wow, I'm glad I'm at the end of my career, not the beginning. Anyway, so been around for a while. And so I wanna I wanna set the context for this talk, which is startups that choose to raise venture capital and kinda go for building kind of a a big outcome.
That's that's all I've ever done, either as an operator inside those startups or as a VC funding those startups or as an investment banker selling those startups. And now as a coach, I only coach CEOs of technology companies that have raised venture. And when you do that, you sign up for a big outcome.
And so I just wanna share some stats with you to set the stage. Right? So in the venture capital industry, returns follow a power law distribution. So the vast majority of returns come from a very small number of investments. And so so some stats for you.
So like, first of all, in general, funded or otherwise, ninety percent of startups fail. Three out of a hundred startups will reach a hundred million euro valuation. Now let's say that you as a VC, you own twenty percent of that. So you're gonna get twenty million dollars when that company exits.
Perversely, that doesn't even move the needle on most funds these days because they're so big. And so you need to chase even much higher, like a hundred million dollar exit doesn't even really get them all that excited, which is kinda crazy because that's a lot of money.
Here's the craziest stat. So since twenty twenty two, seventy percent of the VC backed exits were for a price that was less than the money that was invested in the company. So seven out of ten exits are actually failures where the VCs don't get their money back, and for the founders who were killing killing themselves for seven or ten years, their shares are worthless.
This is truly tragic. And so that's the context here is like when you when a VC decides to invest in a business, it's because they think that you can be one of those outliers. And, like, that's their expectation. That's what they're gonna be pushing you for, and that can be really, really stressful, and some CEOs rise to the occasion, and some don't.
So let's talk about the CEO role and how it differs from every other leadership role. Right? So I was a CFO for a long time. First of all, I studied a body of knowledge. I'm a chartered accountant. And then I took baby steps.
I was a controller, then a director of finance, and then a VP. And by the time I was CFO, I was ready. I I should have asked before. By the way, are there any masochists in the room? Any CEOs? Hands? Hands up? Yeah. What? A few brave souls.
So everyone in this room, unless you're an investor, you're either a CEO or you work for a CEO. And so it's great to just understand this context. Right? Because the biggest outcomes in startup land are are founder led, start to finish. And so there's either a hundred percent correlation be there's a hundred percent correlation between the performance of the CEO and the outcome of the company.
So great to understand the context that either you're facing if you're a CEO or the context that your CEO is facing. And so what is that context? There's no gradual path. You just start the company and like, boom. Now you gotta, like, figure it out.
You're responsible for everything, not just one function. There is no school. There's no CEO school. There's no playbook. If there is, someone would have written the book, and I wouldn't have a coaching business. As your company succeeds, you know, more and more people want a piece of you.
It's really hard to keep up. That's usually when people come to me and be like, dude, can't handle it anymore. Help me out. Board dynamics become a thing. Be sure to come to the fireside chat I'm doing with Fred Destin this afternoon where we're gonna go into that.
And it's a really lonely role. CEOs tell me, like, the bigger their company gets, the more lonely it is. And and, yes, you have a management team, but the difference between you and your management team is you can fire any of them, they can't fire you.
And so at the end of the day, you're kind of alone. So for this talk, I was like, I you know, if I think about the purpose of my coaching, it's to help founders grow faster than their companies, and and really to become limitless.
Right? And so let's look at some truly limitless leaders and see what we can learn. So I randomly picked these eleven companies. They're not the eleven largest companies. This tech startup world is pretty male. I wanted to get some gender diversity in here as well.
But these eleven companies represent six point four trillion of market cap. So some big names here and different sectors. Right? We've got consumer, we've got enterprise, etcetera. And so I set about researching to understand all of the personal habits and the leadership traits of the CEOs of every one of these companies, and that's what I'm gonna present here.
One caveat. Right? I am humble enough and old enough to know that any success that I've seen or been a part of was helped by a very large dose of luck and timing. And so that's not a factor in these slides, but just understand every single company that achieved an outlier outcome was helped by luck and timing along the way.
You could have a really amazing team with a great product, but if you get the timing wrong, it's just not gonna work. Right? It's it might work a little bit or just flat out not work at all. Alright. Let's get into the CEOs.
Brian Chesky from Airbnb. Like many founders, Brian is a night owl. He just thinks best at the at at the nighttime, but he doesn't kill himself by thinking, oh, well, I should be at work at nine AM because that's convention. Right? He starts late, and he goes late.
He exercises every single day. He works out four times a week. He prioritizes eating healthy food. He, meditates. He does transcend transcendental meditation, twice a day. And, you know, you think about meditation, you think about a CEO's job, ultimately, it's to make decisions.
Every day, you're making decisions, small, medium, large. And the clearer or more focused your mind is, the better you're gonna be able to make decisions. He's a a huge learner, relentlessly curious. This is a theme you're gonna see showing up again and again.
He surrounded himself with mentors, from the earliest, days. His superpower is just this massive customer empathy coupled with the fact that he's got, like, a design background. And so he kinda charged his team with what he calls designing an eleven star experience. Right?
You know, you normally think, you know, you go stay somewhere, it's up to five stars. Like, what would an eleven star experience look like? Like, just be impractical. Don't worry about cost. Just think about how you would just absolutely blow customers' minds. And so it's just that leaning into that as a thought exercise just unlocks limits of what's possible.
Huge focus on culture and value. He's got a famous memo called don't **** up the culture that he sends to new employees when they join. And many founders exhibit this, but he's been personified for this thing called founder mode, which is going anywhere and everywhere.
You know, forget the reporting lines. I'm gonna talk to anyone. I'll talk to an individual contributor. I'll look at pixels. I'll think about long term strategy. He has fifty people that report to him. And so as a result, he does no one on one meetings and just massive leverage.
Next, Melanie Park in park Perkins, founder and CEO of Canva. Melanie burnt out early in her career, and so that forced her to prioritize boundaries. She works maybe a little bit in the evenings. She does not work at all on the weekends. Weekends are for recharging.
She walks a hundred kilometers. I don't I think that's, like, sixty miles. I'm not sure. We don't do miles in North America, or in Canada. Every month, she also, like Brian, meditates every single day, and she considers the walks to be like walking meditation as well.
She has a these kind of rituals in the morning. So she'll journal in the morning. That's kind of like her reflection time, and she'll think about big decisions, and she kinda like eases into the day. Super resilient. You know, she was a female founder building a startup out of Australia trying to raise money in Silicon Valley.
She got literally hundreds of rejections, and that just kept her really humble and forced her to learn and figure it out, and now she's got a company worth, I think, forty billion dollars. A core value for Melanie is to be a good human, and they have a vibe team in the company to make sure that everyone's living according to that value.
And despite how big their company is and the expectations that are on everyone's shoulders, they have what is called a sacred lunch hour every day. So everybody stops working, has lunch together. I think that's really cool and completely the opposite of the Silicon Valley culture where we just want you kind of working all the time.
This is a slightly older example. LinkedIn bought Lynda dot com for one point five billion dollars several years ago. Linda actually started this company when she was forty. She was a teacher and was kinda born to do this. Her superpower was to demystify complex things through teaching.
So she basically just turned herself into a product. Because she started at forty, she was more grounded. She was focused on the purpose, which is making sure people had real learning outcomes. So it's guess I guess substance over form, just get it right, delight the customer, and kinda great things will happen.
Alright. Mark Zuckerberg. Lots has been written and said about Mark. Mark sets yearly personal challenges for himself. He learned Mandarin one year. He ran three hundred and sixty five miles another year. He built an AI bot to run all of his house another year.
He reads a book every two weeks. So back to this theme of learning. I wanna just settle on that set on that for a second. Like, think about how big his company is. He's also got a family with two kids, and yet somehow he finds time to read a book every two weeks.
The most successful CEOs I know are all doing that. They're all just voracious learners. He's kind of relaxed, and he's got a bit more of a cooler look going now. But for years, he had the same uniform. Right? He wore blue jeans, a gray T shirt, a black hoodie, just like streamlining decisions.
He has the same things for lunch every day, prioritizes exercise. I really wish he had fought Elon Musk. I would have liked to have seen who won that. But, you know, he does martial arts, and that he's looking a bit more buff these days.
He's known for that kind of hacker culture. He's got a technical foundation. Their ethos for years was, like, you know, move fast and break things. So that's kind of just core to their culture. He's paired the data that comes at like, a data focus that comes out of that culture with a willingness to make big bets.
Right before they went public, he bought Instagram for a billion dollars. Instagram had eight people at the time. Everyone thought he was crazy. Turns out that was the future of their company. Right? So, like, you know, massive bet. And of all the CEOs, he's got the highest bar for talent.
Right? His bar is like, I will only hire someone that I would report to. And she's no longer there, but for years, his right hand, Sheryl Sandberg, was who's the chief operating officer, and that was the bar that he used to hire her.
Okay. Probably the CEO that is most in the news these days, thanks to AI, so Jensen Huang from NVIDIA. This dude is a beast. He works seven days a week. He's up at five AM. He's relentless, but he still prioritizes his energy because he knows the demands he's putting on himself.
Right? So he works out every day. He eats well. He many CEOs would just sort of let the job happen to them, and they're in meeting after meeting after meeting, and it's kinda crazy. He doesn't do that. He prioritizes great big blocks, like two, three, four hour blocks for what he calls deep work.
He's very transparent. So kinda like Brian, he has a lot of direct reports. In this case, he has over sixty direct reports. There's no one on one meeting. There's no, like, one on one communication. He wants everyone to learn. He'll give feedback even if it's negative in a big kind of public forum like this.
So you need thick skin to be able to kinda hang with Jensen. And and that's that culture of radical transparency and learning. Right? He's got very high standards for that, and he's been known to take, you know, some really big bets, and he's reaping the rewards of that now.
Right? He made a focus the company on AI chips several years ago, and now they're their dominant provider of AI chips. Alright. Here's a CEO near and dear to my heart, Toby from Shopify. Another just absolute relentless learner. From the earliest days, even when I was there, he talked about getting one percent better every day.
And he had that could just be like a cheesy poster on a hallway, but he had, like, a process to make it happen, which is he would go home and replay his day every single day. I'm like, I don't like how I behaved in that meeting.
We took the wrong decision in this meeting. And then he would course correct either that same day or the very next day. If you graph one percent improvement per day, that is a thirty seven x transformation in a year. You know, it's really, really powerful.
He his superpower is his technical foundation. He was a core contributor to Ruby on Rails back in the day. He felt like the company was behind on mobile. I was kinda transitioning out at this time, and he decided to run all of Shopify from his mobile phone for a year just to give him empathy for the customer.
And now he's the person who's personally leading the charge on all of their AI efforts. And absolutely customer obsessed. Right? His mission is to make commerce simpler for everyone, to remove friction so that anyone who wants to start a product based business can do so, and is completely obsessed with that problem.
That's why even though he's a billionaire, he works harder than he's ever worked. Right? Because he's not done yet. He completely hates conventional wisdom. When I was there, I was a, you know, a CFO. Everything there's a right way to do things. There's a wrong way to do things.
And I would come in and, like, here's how you should do this, and then he would just, like, make me defend my position and first principles. And if I couldn't, then we weren't gonna do it. So it was it was tough. Alright. Frank Slootman.
I don't know if you have any of you have, read, Frank's book. If you have, then you know that he is relentless. Kind of company after company after company, he comes in, drives up the pace of execution, and creates a massive outcome. He's quoted as saying that the CEO role is insanely confrontational.
He believes that leaders need to push the bar, set the pace, have the the highest standards possible, and dry and this is a quote, drive every second of the day. That's really intense. I don't think I'd wanna work for Frank. That's for sure.
He sets, you know, ruthless, very focused priority priorities, demands, action, huge focus on talent, and he likes to remove passengers. That's what this is his term, and promote front seat drivers. And when you put all that together, this kind of really high bar for talent with this relentless focus on execution, what that results in is speed.
And for a venture backed startup, speed is everything. First of all, speed as measured by the rate of year on year revenue growth is the single biggest driver evaluation for your company. A company that's growing three x a year will be valued more than a company that's growing fifty percent of the year even if they have the exact same amount of revenue.
Speed is also that magnet that attracts ambitious talent. It attracts capital. It attracts customers who wanna choose the market leader, and then ultimately attracts buyers who wanna buy you or who are scared shitless of you. So speed is is everything. Elon Musk, another person who had there's lots written about him.
So many of these CEOs are intense, but he is the personification of intense. All in. Right? Was would famously sleep on factory floors. He was proud of the fact that he would sleep four hours a day. Now he's relaxed that and now tries for at least six hours.
I think that's still not enough, but it's a step in, the right direction. He does he's you know, a lot of these other CEOs take care of themselves, and he exercises. He started lifting weights when he thought he was gonna fight Zuckerberg, but otherwise, he still eats donuts, and he doesn't take care of himself.
But, you know, smartest guy in the room. Literally, you know, we talk about, oh, that dude's a rocket scientist. Right? Rocket science means, like, you're smart. He literally taught himself rocket science, and at the same time, himself these other disciplines. He, you know, he leads by example.
There's no job that's beneath him, and we'll he'll go on the factory floor and uncover bottlenecks and production. He's not sitting here in the CEO's office and, like, telling people to go off and do it. He just go goes and does it. He doesn't communicate through the chain of command.
He thinks communication should go through the fastest path to result in the right decision. So as a result, like Brian Chesky, like Jensen Huang, he has lots of direct reports. He's got a flat hierarchy. The ultimate optimist. Right? You think about all I don't know how many rockets he's blown up in the process of building SpaceX.
All of those are just learning opportunities. Right? They're not failures. They've just figured out what doesn't work, and then they iterate, and they keep going. Obviously, he's made huge kind of bold decisions along the way. He hires in a really unconventional way. He doesn't require university degrees.
He wants to he'll just meet whomever and be like, tell me about the hardest problem you've ever solved. The thing that he's looking for is innovative thinking. Right? And people who think different, people who will challenge the status quo. Larry Ellison, cofounder of or founder of Oracle.
So this is maybe a OG enterprise software company. Larry is a relentlessly competitive individual. He's a competitive sailor. He's won the America's Cup a couple of times. He's a competitive tennis player now. He's eighty years old. This this photo's taken from this year.
He doesn't look like eighty. I wanna look like that when I'm eighty. Now he has invested millions of dollars in, antiaging research. So, he's kinda like that Brian Johnson guy. If you follow him, he doesn't wanna die. But because he doesn't wanna die, he's ruthlessly focused on on health and fitness.
Right? And he thinks that a a clear mind and a healthy body is the foundation for his performance, and he's right. Absolutely. So he's got daily vigorous exercise. He meditates every day. That's the foundation. He's taken that competitive ethos that he has as an athlete into his company.
And so Oracle for years has been famous for just attacking its customers head on, had massive bitter rivalries with SAP and Microsoft, and he'd go and just buy competitors and do, you know, really bold things. His foundation is is that risk taking, and it comes from technical knowledge.
So he's the chairman now. He's got a CEO beneath him, but he's still the chief technology officer of the company, and it's him who makes the big kind of bold bets. And so as a result, he's really deeply involved with product, but maybe less involved with the other aspects.
Last example is Susan. I'm gonna butcher this last name. Wajj Sikhi. Susan is no longer with us, unfortunately, but there's a lot to learn from her. She was a mother of five, and so as a result, she was forced to have boundaries. Right?
So she had dinner with her family every night, was unreachable between six PM and nine PM, and that in no way held her back. You know, she was running a company that had fifty four billion in revenue. But because of those boundaries, because she prioritized, like, I'm not just a CEO role, I have these other responsibilities, it's forced her to delegate and trust in a way that maybe other CEOs did not, and again, in no way held back her performance.
Big focus on learning. She was Google's first marketing manager, but over the years, taught herself all these other different kind of aspects of the business and made big bets. It was actually her who advocated for Google to buy YouTube for one point six five billion dollars.
At the time, YouTube had fifteen million in revenue. For anyone who's good with math, that's a hundred and ten times revenue. So pretty bold bet. And very collaborative. She was famous for writing kind of these she do she practiced a philosophy called build in public.
So they would be share kind of very openly with their community where they were going and seek input, etcetera. So, again, very collaborative, very trusting approach. Alright. So I just threw, like, a lot of blah blah blah, a lot of facts at you.
Let's try and, like, summarize that down to some trends. And these are not universal. Not every CEO practices this. So for instance, Elon Musk could sleep more. But, like, everyone recognizes the importance of sleep. Right? Like, as humans, we're meant to sleep for a third of our lives.
And if it wasn't important, evolution would have gotten rid of it. And I tell my CEOs all the time, today's performance began last night based on when you went to sleep and the quality of your sleep. So sleep's everything. Next is is mindfulness.
And like I said before, the CEO's job is to make decisions. So the more clarity, the more focus you have, the better decisions you're gonna make. Everyone recognizes that health and fitness right? Okay. Here's my brain. Here's my body. Like, you need to kinda move them in proportion. Right?
You need to move your body every day. You need to if you're everyone's here is pretty young, but if you're over forty, you need to actually lift weights, do resistance training a few times a week, and everyone a lot of these CEOs recognize that.
Learning is universal. Again, I'll go back to Toby. They just celebrated their twentieth anniversary. He no longer gets a paycheck, but if he did, he's he's had the same title for twenty years. And if he was paying himself, he'd take a paycheck from the same bank account for twenty years, but it's not the same company, and he's not the same CEO.
He's had to transform himself and what he calls requalify for his job year after year after year. And so learning and self awareness is how you get there. On the leadership trait side, all of them have massive focus, you know, have few big bets, very clear direction.
Slootman is all about kinda compressing timelines. Musk's about a task at finding bottlenecks. All of them have really high bars for talent, like Zuckerberg only hires people that he would work for. All of them flatten communication lines. Like I say, Brian Chesky's got fifty direct reports.
Jensen Huang has over sixty. Elon will go anywhere and everywhere to, like, sort out issues. All of them have big bold visions, and and a lot of them have a, you know, a huge focus on the customer. So, you know, let's kind of start wrapping all of this up.
Every single one of these leaders has some superpower, and they've designed their role, and then ultimately their leadership team and their company around that superpower. Right? So I'll go back to Shopify just because I know it the best. Right? So Toby's superpower is his technical foundation.
If you've ever seen him talk, he's very introverted, And so as a result, he doesn't do the things that you think a CEO like, publicly traded company, a CEO would have to do all the Wall Street BS. He doesn't do any of that. His right hand Harley does that.
He's built his role around the things that are his superpower, his zone of genius, the time where he's in flow and it doesn't feel like work. All of them are in love with the problem. That's actually the only enduring source of motivation that will keep you going year after year after year.
If you start a company because you think there's a lot of money to be made, that won't keep you going. If you've ever gotten a pay raise, you felt good for, I don't know, an hour, and then you get on with the rest of your life.
Money is not an enduring source of motivation. Being in love with the problem is. All of them have some relevant technical expertise. Now technical doesn't mean coding. Not everyone here can code, but they're focused on the product or the core. There's two cores to a business. Right?
There's building product and selling product. The other things are important, but they're in service of those two cores. Every so CEO here has a deep competence and something that relates to either building the product or selling the product. All of them have really high and seemingly impossible standards.
Elon's famous for pushing his team to do things that they considered impossible, and it turns out you could do them. All of them question conventional wisdom and use this kind of first principles thinking approach. All of them prioritize speed and communicate very directly in order to promote speed.
And as a result of all these practices, all of them have unlocked a flywheel of growth in their business. And Warren Buffett, the world's most successful investor who just announced his retirement this week, is famous for saying that the most powerful force in the universe is compound interest.
All of these CEOs have compounded themselves and compounded their companies year after year by following these practices. And they recognize that because they're doing this for a long time that they need to prioritize health and they need to keep learning. So my question for you is, are you limitless?
I think that one of the most beautiful things about humans is we have infinite potential. Toby is maybe the most successful high school dropout that I know. The only reason he started a company is because he didn't have a work permit to get a job in Canada.
And now he leads a ten thousand person company, and along the way, by the way, he's taught himself to be a professional race car driver. Every single person here is capable of that. So that's my question for you. Are you limitless? In wrapping up, I invite you to subscribe to my newsletter.
It goes out every week. And follow my podcast where I interview smart, limitless CEOs. Thank you. Thank you so man.
