Episode 39 · Ian Adamson

How to Build an Extraordinary Life Without Following One Path | Ian Adamson

Parallel Entrepreneur with Mark Cleveland · Episode 39

0:00 / 59:09
How to Build an Extraordinary Life Without Following One Path | Ian Adamson
0:00 / 59:09

Episode notes

What do engineering, world championship sport, product innovation, television production, and the Olympic movement all have in common?

In this episode of The Parallel Entrepreneur, Mark Cleveland sits down with Ian Adamson, Chair of the World Pentathlon Multisport Obstacle Commission, to explore a career built on curiosity, continuous learning, and saying yes to opportunities most people would never consider.

Ian has spent decades moving between engineering, elite sport, business, product development, and global leadership. From designing products for Nike and competing as a professional adventure racer to helping guide obstacle sports into the Olympic movement, his career is proof that the experiences we collect often become our greatest advantage.

Along the way, the conversation explores parallel entrepreneurship, decision-making, resilience, innovation, engineering thinking, AI, adventure, leadership, and why living an extraordinary life often begins by embracing the unexpected.

In this episode

• Why Ian believes your greatest superpower is the ability to learn
• How engineering shaped his approach to leadership and problem solving
• The mindset behind managing multiple careers at once, what Ian calls "multi-switching" rather than multitasking
• Walking across China... twice
• Why saying yes creates opportunities you could never plan for
• Lessons from building world-class sporting events and international organizations
• What innovation looks like when you're too early for the market
• How AI is accelerating discovery and changing the way we learn
• Why the Olympic movement is about creating better humans, not just better athletes
• The importance of curiosity, legacy, and leaving the world better than you found it

Whether you're an entrepreneur, leader, engineer, athlete, or simply someone who enjoys learning from people who have taken an unconventional path, this conversation offers practical wisdom and a refreshing perspective on building a meaningful life.

Links & Resources

Join the Parallel Entrepreneur Network, and explore more founder conversations on The Parallel Entrepreneur Podcast.

Connect with Ian Adamson

Follow Ianadamson on LinkedIn · World Pentathlon Multisport · World Obstacle

About the Host

Mark Cleveland is an entrepreneur, investor, and advisor who works at the intersection of multiple ventures. As the voice behind The Parallel Entrepreneur, he explores how founders build aligned businesses, strong teams, and sustainable momentum, without forcing themselves into a single path.
Follow Mark on LinkedIn

Related conversations

The AI Skill Every Working Adult Needs to Learn — Spencer Handley on learning how to learn and working alongside AI
The Power of Curiosity — Carla Bailo on engineering, mentorship, and the joy of embracing the unknown
Start Paralleling — Mark Cleveland on why the future belongs to parallel thinkers

Subscribe for more conversations with founders, investors, operators, and creators building extraordinary lives across multiple ventures.

#ParallelEntrepreneur #MarkCleveland #IanAdamson #Entrepreneurship #Leadership #Innovation #Olympics #Engineering #AdventureRacing #ObstacleRacing #BusinessPodcast #PersonalGrowth

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Full transcript

Accumulation of knowledge, experience, and education. We all have that superpower. The question becomes: How much do you get on your journey through this life of ours to then leverage into other things? Well, you walked across China, and then you walked across China again. Like, who does that? Why did you do that? "The Chinese wouldn't let me out." What would you say to your younger self?

Nothing. Not going to tell you anything. You've got to figure it out, because that's the fun part. You know what the regrets are? What you didn't do. You know what you never regret? It's the thing that you did do that turned out to be a catastrophe or a really weird thing, but at least it's a story. I've got plenty of those.

Welcome back to The Parallel Entrepreneur. Some guests you introduce with a list of accomplishments. In this episode, Ian Adamson— his accomplishments are so extensive, the list would start to feel like its own endurance event. So we'll spare you the full rundown. Check it out in the show notes. The CV— the résumé—will blow you away. But what I can tell you is that today's guest has moved seamlessly between engineering, elite sports, television production, product innovation, and global competition leadership—the entire landscape.

From working with brands like Nike to helping shape the future of obstacle and multisport racing at an international level. It's a career that doesn't follow a straight line, and that's exactly what makes it so interesting. There's a lot more behind that story, so stick around and discover some more. I'd just like to say, welcome, Ian Adamson, to The Parallel Entrepreneur, brother.

My first question is really around how you manage energy. Give the audience a sense of what you're trying to accomplish today, and then I'm interested to hear you weave into how you manage your energy levels and productivity on this multiple-paralleling thing that you're doing. It's not multitasking, which I actually don't believe in.

It's multi-switching. Your ability to concentrate on something and focus on it, uh, to the exclusion of everything else allows you to do something really well. I don't believe it's possible, certainly not for me... opinions for a legal case and then get distracted by my phone pinging about something in Olympic sport. It just won't work.

So, I have an ability which has its own challenges, to switch everything off, focus on that one thing, and then, when I'm done with that one thing, immediately switch to the next thing, which could be completely unrelated. The energy part is interesting because I think most humans probably require some level of downtime. Let's call it a quiet space where you can think about other things or just kind of let your mind go blank-ish, or not think about whatever the job at hand is.

For me, it's manual labour. I love building stuff, so, fortunately, it does kind of get into my actual work in Olympic sport, where I'm often out working on events, obstacles, and Ninja Warrior kind of stuff. So, that's me with my hands. Most recently, my wife and I got really into saunas. So, in the last couple of months, I built two saunas.

Really nice ones— the kind you'd expect to find in a Western hotel spa. With all the bells and whistles, and for me, that would be switching off in the evening. I'd switch off my "chair job" and switch into building a sauna. And for me, that includes opening up walls in the house to run 240-volt electrical, and then trenching for conduit to get to the solar stuff, right? So that's manual labour—framing, everything you would do to build a house, which I can do, by the way.

I've actually built houses, so I can actually do that. That's the engineering side. That's my engineering brain going, "Oh, this is great. Now I get to wield a hammer, dig a hole, connect some electrical things, hopefully not blow myself up." And that's, you know, this other part of energy management. Where does the energy go? The energy could be physical, mental, emotional, or spiritual, and for me, downtime comes from switching between things.

Switching from, say, concentrating on Olympic sport to legal forensic work, to building a sauna. or riding my mountain bike. There you go. I call that context switching. I think it's a superpower of parallel entrepreneurs. Let's just delve in for a minute into your accomplishments— your gold medals, your world champion status in different sports. I'd like to help set the stage by asking the question: How many medals have you had around your neck, and which one are you most proud of?

I have three X Games medals— gold, silver, and bronze in the X Games. That was in the beginning of my career as a professional multisport athlete with Nike. That involved many events, mostly multidisciplinary sports. At the time, adventure racing was a big deal as a televised, big broadcast, big-money sport that lasted until about 2006, which is when I retired.

So, that was one of a swag of world championship wins. I think our team won about 30 over that period. I won 23 medals, including 11 gold, during that time. How does training for an athletic event in your career, and building media and entertainment strategies around it, and then trying to build an international Olympic alignment around this becoming a new Olympic sport— those three things are an astonishing set of accomplishments that seem almost routine for you, Ian.

But there must be a superpower that you've uncovered. What do you think it is? The ability to absorb information and use it for some purpose. If you look at the formal education system, that's part of it. We go to kindergarten, elementary school, grade school— it goes on and on, right? The further you go, the more you accumulate.

Now, that's the academic side. But accumulation of knowledge, experience, and education is exactly what you're describing. We all have that superpower. The question becomes: How much do you get on your journey through this life of ours to then leverage into other things, which makes it easier? Another example I think many people appreciate is language.

Understanding one language, or speaking a language fluently, as a kid—or learning multiple languages as a kid— makes it much, much easier to learn more languages. And the Pope—Pope Leo, I believe— speaks 12 languages fluently. I've heard him speak French, and I couldn't tell he wasn't French. Not that I understand French that well, but I'm listening to the guy thinking, "That's extraordinary that he can do that." On the other hand, he's dedicated his entire life to doing exactly that, which is what you're asking about. He did it.

Leonardo da Vinci did it. Michelangelo did it. It's not that they were extraordinary people, although they became extraordinary. We can all do that. We can all be extraordinary, should we choose to do it. I think most people just don't have the will or the desire. And that's not wrong. Maybe you like sitting on a beach drinking Mai Tais. If that's your goal, then do it. You've achieved it.

That's just not my goal. So, little Ian Adamson, at seven years old, was looking through the Guinness Book of World Records, trying to find interesting, challenging things, and then you set yourself a goal of becoming a Guinness World Record holder. Yeah. You asked about Olympic sport. It all ties together, by the way. All these things we do— you do it, I do it.

I've seen your remarkable career through many things, and they're all complementary. Whether it's making socks or running a hobby store— whatever it is, all of that matters, because all of it becomes part of you. You are the sum of your experiences. If those experiences include knowledge and education, then the sum of who you are includes a lot of valuable things.

Ian, you're the President of the international governing body for obstacle sports... Big vision—what's been your biggest challenge? The biggest challenge with, uh... building an international multisport federation, which is technically building a sport—or sports— is dealing with people. But I think that's the same in any business.

It's the people. Humans can be terrible people, and there can be lots of challenges around people management. People management. We believe—without hard data— there are at least 20 million people doing obstacle sports around the world, in about 140 countries. So, building an international organization is a bit like the United Nations. Each country has a national governing body.

That national governing body is then a member of the international governing body. The international governing body then manages all of that, and it's a scalable system. Directly within the federation system, it's about 800 people. That's not insignificant. I'd guess that's a medium-sized company by most standards. A medium-sized, small multinational.

But now, as of today, it's been formally announced, I am the Chair of the Obstacle Commission for World Pentathlon. On March 15 this year, our organization voted to dissolve itself as we integrate into World Pentathlon and the Olympic Movement. So all of our sports are being aggregated into one international multisport organization, which is World Pentathlon Multisport.

That organization has been part of the Olympic Movement for 100 years. It was created by Baron Pierre de Coubertin, who created the modern Olympics, so it's a really interesting history. to house the most complete athlete, or identify the most complete athlete. The story goes that he based it on a courier on a battlefield, taking a message from one general to another general on the other side.

So, he would run out of the tent, grab a random horse, gallop across the battlefield, use his pistol to defend himself, run out of bullets, draw his sword, and his horse would get shot out from under him. He'd then have to swim across the river and run away. So those are the five disciplines: shooting, fencing, running, swimming, and riding.

So, you've also produced a lot of television content, starting with adventure racing, right? And then moving into American Ninja Warrior. I went to the set and met Travis McDaniel, the owner. He passed away tragically from cancer, but Travis and I had a chat, and I did what we often do in television for impossible projects, which is to say, "Hey, this hasn't happened yet, but let's just say, hypothetically, we managed to get an event into the Olympic Games.

Would you be interested in collaborating to get there?" And Travis was like, "Yeah, that sounds great." We've stuck together ever since, and the current— or rather, the most recent CEO— was actually on my board for World Obstacle. I had to keep people close. on my board. Joe would call me every now and again, and he'd say, "I've got this new event.

It's fantastic. It's called the Death Race." "That sounds great, Joe. That's a great idea... ...until it happens." "I know, right?" And it's still going. The Death Race is still going. So I said, "That sounds great, Joe." Then, by 2009 or 2010, he had started Spartan Race. Same thing. He'd say, "Hey, Ian, I've got this. This is going to be the best one yet.

This is going to be amazing." So he started Spartan Race, and I was like, "Yeah, whatever, Joe." Not really interested. It's huge. It's unbelievable, right? It became maybe the biggest endurance event producer in the world. They have more people doing their events in one year, in one country, than Ironman does worldwide.

That's how big they are. They're massive. And here's your answer, right? You get something out of the blue, and you go, "That sounds great. Let's do it. It's an adventure." Exactly. Exactly. I think that’s a common thread in our conversation: some unknown, unexpected thing will always put an opportunity in front of you, and you get to say yes or no. I think a lot of people say no to a lot of stuff they should just be saying yes to. You know what the regrets are? What you didn’t do. For sure. It’s like, “Duh, I wish I’d done that.” You know what you never regret?

The thing that you did do that turned out to be a catastrophe or a really weird thing. At least it’s a story. I’ve got plenty of those. Yeah. With some of our experiences, most of them are failures. But that’s the truth. People go, “Oh, you did all this stuff. It looks amazing.” And it’s like, “Yeah, what you haven’t seen, and what I don’t really talk about, is all the stuff that went wrong.” Right, because most of it goes wrong most of the time. You just have to accept it and roll with it. The attitude, for me anyway, is: “Okay, that didn’t go as expected.” That’s usually what actually happens. It didn’t go as expected. But you know what?

That was a really, really good lesson, and next time I’m going to do it better, because I just learned how not to do it. Now I know a much better way to do it. Or, if it didn’t go as expected, there’s an opportunity that was better than you’d hoped. Exactly. This whole thing is about whoever said, “You’re the sum of your experiences.” We are the sum of our experiences.

And if the journey is an unexpected one, and it is the journey, because what else are you going to enjoy? If you don’t enjoy the journey, which is life, you may as well not live. So enjoy whatever you’re doing. I

asked you a question in one of our many catch-up calls, because on the podcast I’ll ask, “Knowing what you know now, with all these experiences, what would you say to your younger self?” Nothing. Nothing at all? You feel like you’d walk up to your younger self and say, “Hey, dude, nothing”? Yep. No. I’m not going to tell you anything. You’ve got to figure it out, because that’s the fun part.

You had a lot of experiences in China, and I think one of them that still leaves my jaw dropped is when you walked across China, and then you walked across China again. I mean, who does that? Why did you do that? I had taken a year off in 1983 after high school to travel and sail. That was a sailing thing. I did two years of school, then went back out for another year. But it was more than a year, because Australia’s school year, like most school years, is actually about 15 months. So I had a bit of time to poke about. I flew to Hong Kong, then took the ferry over to Macau and went into China. At that time, you were officially

allowed to visit, I think, Beijing, Guangzhou, Shanghai and maybe some tourist spots. That was it. You had this sort of permit thing, a little paper book that allowed you to go places. But when I was younger, I looked quite Chinese, so I just bought local clothing and took off. I ended up going out to Kashgar, far western China.

I started out on a steam train, ended up getting out there, and then tried to cross into Pakistan. Pakistan was a Commonwealth country, so at the time, with an Australian passport, I did not need a visa for Pakistan. But the Chinese wouldn’t let me out because they said, “You need a visa for Pakistan.” I said, “I don’t need a visa. I’m a Commonwealth citizen.” They said, “You do need a visa.” I finally went back to Beijing. This was like the second crossing back to Beijing. I went to the Pakistan embassy and camped out there for a week trying to convince them I needed a visa, which I didn’t. They didn’t want to give me one because they said, “You’re a Commonwealth citizen. You

don’t need a visa.” I finally convinced them, so they gave up and said, “Okay, here’s your visa stamp.” I got the visa, went back to Kashgar — that was my third crossing in China — and then I was standing at the border to Pakistan. It’s no man’s land. It’s like 100 kilometres of no man’s land. I was standing there in a high-altitude desert. There was nothing there. There was actually a sentry with a little pillbox, a boom gate in a vast empty space, and his rifle. That was it. I thought, “Okay, now what do I do?” In the far distance, as I was standing there, this little cloud of dust appeared and got bigger and bigger. Then there was a white Toyota Land Cruiser with a

whole bunch of French journalists. They said, “We’re the first people to cross the Karakoram to Kashgar and into China in 100 years.” I said, “You are from south to north. I’m going to be first to do it from north to south. Can I use your car?” They said, “No problem. We’re out of here.” So I jumped in their vehicle with a friend of mine and we went south. We believe we were the first people to have done it in 100 years, on 19 May 1986. Then I got really sick, and there’s a whole other story around that. But that was part of my tooling around on foot

in 1986. When you decide you’re going to do something, what’s the next step for you? How do you break problems and challenges down into winnable parts? I switch my brain to the engineering side. I go into project-management mode, and that means creating a schedule with goals, dates and action items. Sometimes it’s mental; mostly, I put it out in the calendar. But everybody, I think, has to have some kind of way to reach down deep and pull in that extra ounce of motivation, whatever that is, in order to accomplish and overcome some significant challenge. What would be an example of that from your experience? The motivation while we were racing changed over

time. In the early days, it was to see if we could finish. It started as fun and new and exciting. Then it became professional and exhausting. Then the races became, “How can we make this enjoyable?” So it would be: “Let’s just get ahead of the other teams as far as we possibly can, then sit down and look at the view.” That’s what it ended up being, because at that point it was coming full circle. What made this great to start with? It’s an amazing place. It’s beautiful.

It’s this pristine forest. It’s gorgeous. There are jumping whales in the Arctic Circle and rainbows. That was the fun stuff. I just wanted to do that. I didn’t want the other stuff. I just wanted that stuff. We talked about the experiences you’ve had, and I’m gathering this sense that it’s not just that you know what to do, but that you know how to handle the unexpected. Is your experience knowing what to do most important, or is your experience knowing how to handle the unexpected most important? Let’s say you have a fine arts degree, but you end up being a TV producer. It doesn’t matter what the degree was. What you learned at school was how to

learn. That’s ultimately what it was. Most people going to school have no idea what they want to be at the end. They probably switch majors twice. I guess it’s not uncommon. Why? Because we’re finding our way. School is a journey, and that journey teaches you all sorts of stuff that you need later. So go to school. Why? What do I do? It doesn’t matter.

I’m not going to tell you what to do. That’s like my former self. Would I tell my former self what to do at school? Hell no. Go figure it out. Do something and figure it out. I remember you teaching me about running barefoot and the mechanics of running. I was training for some triathlons at the time, and you were saying it’s impossible to run with bad running mechanics if you’re barefoot. My mind was short-circuiting. I put some Swiftwick socks on and went out and started running barefoot, which was actually spectacular.

It was very, very weird. It’s crazy weird for people who wear shoes, and most humans on Earth really don’t, by the way. If you’re wealthy enough to afford them, you do. That’s a whole other conversation. You should have Mark Cucuzzella on this, Mark. I’m sure you know Mark. You built stuff for him. We went through that whole compression thing with Mark.

That’s right. Developing the compression socks, which I still use. They’re spectacular, by the way. We were trying to develop the world’s best compression sock, and they arguably were. I still use them. I still have them. I only use those ones. They last forever. They were medical-grade compression socks. When I retired from the company, leadership ultimately decided to abandon that particular initiative. What I find in my own professional life is that I’m going to push the edges, push the boundaries, and try to figure out why something cannot be done. I don’t have preconceived notions about why something I don’t know how to do can’t be done. So

I’m going to go figure it out. I wanted to make a medical-grade compression sock that was not going to wear out. Boy, we got some balloon-toe stuff going. You and I were like, “We literally innovated in that space.” But then the company decided to stay focused in a different area, and we were never successful. Actually, that’s a failure of mine. We had the world’s best medical compression sock, and I priced it too low. This is a lesson. I priced it too low. The market thought that a great medical compression sock had to cost $80, and I thought that was ridiculous because it should be about $35 or $40, and we

could produce it profitably for that. If you’ll remember, we were out there building the world’s best sock, and at $40 a pair, people didn’t buy them. The medical community didn’t buy it because of preconceived notions about price points and value. Market forces have come to bear, because I was in the pharmacy at the local hospital just the other day, and they have racks of medical compression socks now which are at a reasonable price — the price you had originally. You were too far ahead of the game. I mean, this is a common problem: being too early.

Lia suffers from the same thing. She’s always too early. Her business suffers a bit because she was too early into the business. The good thing is she got the patent, so that’s not too early. She did it with online fitness programming. When I first met her in 2004, we went down to a studio of a friend of ours in Denver to produce a Fit Tip of the Day: fitness workout videos for mobile devices. Motorola said, “It’s never going to happen.” AT&T said, “Nope, not a chance. No one’s ever going to do that. No one will ever look at a phone and do a fitness workout or have anything to do with that. It’s just a stupid idea.” Lo and behold, that’s probably the

only thing people do now, because it’s right here. Whether it’s on your spin cycle or whatever, it’s going to be on a tablet. It’s going to be right in your face. Lia had produced a whole series of these things. We were the crash-test dummies. We were the cast in it. It was good. Fit Tip of the Day. But the same thing: too early. People were like, “No, people aren’t going to do that.” Until someone does. We don’t really know what we want until someone shows us what’s possible, and then many people, most consumers, have their eyes opened. It’s not like you’re looking at a market and everybody wants this, so you’re going

to deliver it. It’s more like, “I’m going to create this, and the market exists, but the timing is off, or the capital formation is off, or the reason we fail is that we don’t have the right team.” What do you think the antidote is? You just keep after it, or then what? Yeah, you do keep after it and apply pressure. Constant pressure. I call it just applying constant pressure. Inevitably, you are not the first — maybe not even the best — but if you’re the guy who applies constant pressure, that’s the one that’s going to stick.

Here’s a parallel for you on this exact topic. In the 1890s, there were four Olympic Games. There was an American one, a French one, a Greek one and a British one. The Hellenic Games, I think, are still going. The one that we know today has its own history, but you get to write the history if you’re the winner. You have a hard time finding these other Olympic Games, and one of them was around for at least 60 years before what we know today as the modern Olympics. Baron Pierre de Coubertin, the founder of modern pentathlon and the founder of the modern Olympics, won. That’s the one we know.

The only games we know today are the ones we know because he won. He was smart. He went to Rugby School in England to learn how to do sport, because Rugby School in England — the British, really — invented modern sport as we know it. All the football codes came from Rugby School in England: American football, Australian football, rugby union, rugby league and soccer. They all came from Rugby School in England.

So did the modern Olympics, ultimately, because Baron Pierre de Coubertin was an educator and he understood school and education. He went to Rugby School. Over the gate to this day is “Faster, Higher, Stronger” — Citius, Altius, Fortius. It’s on the gate to this day and has been there since Baron Pierre de Coubertin went there. That’s the Olympic motto. So Rugby School has a lot to answer for.

These games died out in competition with one another until there was an emerging winner. They were all there at the same time. It’s kind of like humanity. Our species walked the Earth at the same time as the Cro-Magnon — or wait, no, Neanderthals. I think there’s fossil evidence that Neanderthals were walking and existing on Earth at the same time as what we would consider modern humans.

Bigger, stronger, smarter, but not more successful. There’s a difference. What’s the secret? It really goes back to the title of this show, which is Parallel Entrepreneur. I think what humans can do quite well is that they have a capacity to do things in parallel. If you are single-minded, single-focus — bright light, narrow focus — you can get something done really well, but you might fall off a cliff doing it because you’re not paying attention to what’s around you. What humans have a capacity to do, not that they always do it, is to have awareness of other stuff. Some people do it way better than others. Survival studies show, I think based on airplane crashes,

that about 10% of humans will probably survive when something unusual happens. I would probably class you in that. You would be that person, because you’re thinking outside the box. You’re thinking, “What else is going on?” That’s curious. Most people aren’t like that. They’re stuck to their phone, or they’re single-focus.

They’re not paralleling it. They don’t have the awareness of the other stuff. If you don’t have that awareness, you’re probably going to fail if something really goes wrong, because you didn’t realise there was an exit on your left three steps back. In a plane, you might be like this: do you know where the exit is? I pay attention to the exits. I absolutely do. Exactly. In front, behind. Not only that, you know the people around the exit.

The exit on the left has a big guy in the middle. I’m not going to go to that one. The exit on the right has a couple of kids. Help them out and then go out that one. It’s kind of like that. I guess the military calls it situational awareness. I think some people innately have that. You also know the semi-trailer in the right lane coming at you from behind. If you don’t know that and you’re driving, you’re an idiot, because that’s what’s going to get you. But most people are like this: they just focus on the road, tunnel vision down the road. Terrible idea. There’s a certain numbness that I think we

can observe. I find when I talk to people about paralleling and parallel entrepreneurship — my careers overlapping, my companies overlapping, some of them being obviously synergistic and some of them not obviously synergistic, from short-sea shipping to sock manufacturing — they’re all opportunities to learn for me. They were all things that interested me, and I never thought I couldn’t do it. But I do hear, when I start talking to people who don’t make the show, that they’re not the right fit. Why? Because they’re great entrepreneurs, but they really just think they can only focus on one thing and that’s what’s going to make them successful. I’m sure it does in most

of those cases. No question, they’re successful. But there is some form of self-limiting belief there. I want to pull on that thread in this world of parallel entrepreneurs. From the outside, it would be, “Oh, you’re really successful doing stuff.” From the inside, it would be, “Yeah, parallel entrepreneur. That makes complete sense to me.” Lia won Entrepreneur of the Year for EY, some major award for Ernst & Young, a few years ago. Then she got to go to the EY annual shindig over in Palm Springs or Palm Desert, which is astonishing. The way it works is that the top couple of hundred people in the world

— leaders in their fields, in innovation and startups — get to be those people. It’s not the Fortune 500. It’s the cream of the crop. It’s the top of the top. Every single person there has this parallel entrepreneur mindset. They use many different terms to describe it, but every conversation is going to be like this conversation, for days. It’s exhausting because it’s so engaging and incredibly insightful. You leave and you need a year to recover because you learned so much in such a short time and made so many connections. You can also see how it’s so perpetuating, because

every conversation ends with an unexpected outcome: “Oh, you do Olympic sport? Oh, you do this? We should do this, and I do that.” It’s exactly what you want and expect, but also unexpected at the same time. The expectation is that every conversation will be fascinating and there will be an unexpected outcome. Everyone knows it, and everyone’s there for that. Ernst & Young, which a lot of people don’t know, is one of the top four accounting firms in the world. Their success is not only that they’re an accounting firm, which they are staggeringly good at, it’s that they are connectors. They don’t ask for anything, ever. They are not promoting themselves at all.

They don’t need to, by the way, because they’re that good. Being associated with EY at any level is a big deal. It’s like having a PhD from Harvard, or whatever you want. It’s like, “Oh, you’re an EY alum? Let’s have a chat.” My friend Brandon shared a piece of advice recently: dress so that if someone dressed up as you for a costume party, everyone would know it was you. Now, that’s not entirely about clothing. That’s about identity, about showing up fully.

My wife, Jenny, and I are leaning in on this concept, both in our personal lives and now in a little startup we call Happy Overall. We’re making overalls. Each one is made to order as a wearable canvas for art: overalls that are comfortable, durable and expressive. We’re sourcing soft 100% cotton. We’re partnering with designers and with local seamstresses who love the artistry of a well-crafted piece of clothing. We’re launching in summer of 2026, so check out happyoverall.com to see pics and see if anything resonates with you. Fully you, and it’ll happen every time you reach for them. If you want

to be part of the first run, join our waitlist at happyoverall.com. I was watching a show. When I can’t sleep, I watch something odd with Neil deGrasse Tyson, or something on YouTube that is research and is going to expand my mind because I’m curious. I started watching something the other night about sperm whales and the AI decoding of their language: 9,000 recordings and how they set up the audio, almost like a TV production. They showed how they went about laying out the sonar and the audio recording devices, and how they placed them on the pod —

the female leader, the male leader and the kids — and how they were able to triangulate in order to know which whale was talking to which whale. They made the assumption that they could figure it out, and then they had this massive amount of data. The conclusion fascinated me: they are speaking a fully developed language with vowels.

They’re addressing one another and communicating in the same way that humans communicate, and they’ve developed this over their own millions of millennia. We just think they’re clicks, but in fact we’re wrong. It’s a complete language that we can decode and communicate with. Now, have you seen a whale that would coach you on where to stay, straighten up your sailboat and fly right? Strangely, cetaceans sometimes do assist humans on craft. In fact, I think there was something in the news recently about a whale or a dolphin or something that helped someone. It’s not uncommon. I’ve seen it before, and that actually doesn’t surprise me. That clicking thing — the Maasai language

has clicks, so it’s not that different from whales. How did that develop? Who knows? That’s probably not a connection. It’s a random coincidence. That brings up AI. I imagine AI had a hand in that because it would be able to process that data quickly. Yes, it’s about data processing. I’m not really into AI that much. I’m not allowed to use it for legal work for lots of reasons, but it’s fascinating. Lia paid a company to predict how many uses are in an eyelash container. These little tubes don’t have much liquid, but you don’t need much. We were questioning it, and then Lia said, “Hey, let’s just have some coffee and do the evaluation ourselves.” So we got a bunch of

the containers of eyelash and eyebrow serums and started measuring uses. The company had done it on paper towels. They got the little wiper out, which is like a spoolie brush you use for mascara, and they were wiping it on paper. Lia said, “Well, that’s not accurate because it’s not an eyebrow.” So we did it on our eyebrows. We spent a morning going through hundreds and hundreds of uses of these things to create the data to see if it was correct.

We scratched the hell out of our eyebrows because the little spoolie brushes are kind of abrasive. Then our eyebrows went crazy, because when you scratch into them and expose blood vessels, now the stuff is going right into your system. That’s a really good way to get the stuff active. We found that out later. That was incidental. What ended up happening was we had a notepad and we were writing by hand in columns: time, amount, weight. We had a little microgram weighing scale, so we’d weigh things and write it down. We did this for a whole morning, and by the end, we had thousands of recordings. Then Lia took a picture with her phone. She has one

of the commercial-level AI programmes, just for her. She took a picture and said, “Now what do we do?” I said, “Well, you want to run a statistical analysis. Get the standard deviation, the mean, the mode, the average, the variation, and predict what it’s going to do.” Basically, do all the stuff we do as engineers. I was there doing it by hand just to check it, with my calculator, old-school, pressing buttons and writing things on a piece of paper.

AI did it in about 30 seconds. Then Lia said, “Oh, I’m putting it into a format that’s acceptable by the regulatory authorities in the United States and in Europe.” This thing spat it out so fast. I sat there for an hour checking it, and it was on the money. I went, “Holy shit, this is good.” It was so much work. I didn’t even run all of the stats.

I did a few basic things. I didn’t do the standard deviations, but I did some of the basic stuff just to check it. It was on the money. It was just amazing. That’s been my experience, although lately, unfortunately, some of my AI-centric projects feel like there’s just constant context rot. Keeping it framed in and remembering the progress we’ve made to this point feels like it always wants to start over again.

I’ve been focusing on accountability and isolation, and on how to make sure I’m building upon a previous factual success. Like that hour you spent trying to validate the numbers — it was right on. If you kept doing that analysis, would it get less accurate over time? It’s been frustrating and enlightening at the same time for me. That conversation about AI — and I didn’t think we were going to go there, but lots of us do today — my observation is that I think we’re afraid of the discovery. I think the pace of discovery is going to completely surprise us.

If we want to learn, we’re going to learn a whole lot really quickly, really fast, in a society that sort of likes things not to be so fast: “Slow down, junior.” I’m not so concerned about the

job-loss kind of stuff as I am about how we absorb new facts and new discoveries. Things like whales communicating in full sentence structure and addressing one another the way you and I are right now on this podcast — is that going to blow some people’s perspective, or are they just going to ignore it and move on as if they’ve got blinders on? It feels like a huge opportunity for discovery and curiosity to really take root with humanity. I’m not afraid of it. I’m frustrated by some of the learning curves I still have to overcome, but it’s exciting. It’s a very exciting time. The thing I find

exciting about it is that it’s unexpected. We don’t know. We can’t predict it. It’s moving quickly. That’s fun. I love progress. I see the spectrum of mindsets in things like construction. Behind our place in California, they’re building housing for academics. It’s about 100 homes on a big, nice piece of property that the university owns. Some of the neighbours are like, “This is a disgrace. We can’t have this progress. This is going to wreck the neighbourhood.” There’s that NIMBY thing. I look at it and go, “This is fantastic. This is really interesting.

I love how they’ve figured out the traffic on this. I like the process.” I like change. I don’t like the fact that we’re overpopulated by 80% of the humans on the planet, but that’s another discussion. People keep saying we need more money and more people to create more money. It’s a death spiral. I hear that a lot from economists: “We need higher birth rates so we can generate more people to pay for more people, to get more people.” It’s a terrible idea. What they’re actually saying is there will never be enough people to pay for the people who are here, so you just can’t keep making more people. It causes all the problems we have. It’s fighting for space.

It’s all about humans fighting for stuff, and that’s a terrible idea. Japan is doing just fine, and their population is declining, so do that. Quality of life might be a better focus, right? Quality of life. We can’t support this. We have exceeded the ability of the planet to support humans. We exceeded the ability of the planet to support humans decades ago. Why do we not believe that?

Who is feeding us this line of shit? It’s money. It’s all about the money. Look at the idea that you need a higher birth rate to have more people to create more money to support the people. No. That’s an absolutely disastrous idea. That’s a false premise and one that is completely flawed. There’s nothing valid or rational about that at all. We’ve talked a lot about adventure today, and recently this trip taken around the moon was an imagination-capturing moment in time. It reminded me that those astronauts are athletes. They’ve been training for 4

Gs and more for a long time. What perspective do you have on the athleticism of our astronaut population? Everyone should train to be an astronaut, and then we’d be way better off. Astronauts are mentally, physically and emotionally capable and competent humans. That’s what we need. We need those people. We want less thoughtless, mindless robots and more thoughtful people. I’m told that if you look down at the Earth and see the blue marble, it completely changes you, which I believe. Being on the ocean is the same. When you cross an ocean slowly on a little boat, you get a completely different

perspective of the planet, and then you realise how incredibly large, delicate and complex it is. Maybe this is the last thing I’ll say. In 1974, a gentleman sailed from Sydney to Tokyo on a little sailboat and wrote a book about it. The book was about sea life, the birds, the whales, the fish and the abundance of the oceans. Many decades later, I’m going to say 2004, he repeated the journey. The thing he wrote about the wildlife was that there was none: no whales, no schools of fish, no birds, didn’t catch anything. Nothing. It was a

desert. I’ve seen it in person. I was sailing in the late 70s and the 80s, and my memory was the same. It didn’t take long. In 2013, 30 years after I’d been on the Great Barrier Reef, I went back and went sailing again to places I thought I knew. I had my wife and a couple of friends, and we went out and said, “We’re going to go to the outer reef off Cairns, and it’s the most amazing thing you’ll ever see in your life. It’s indescribable.” I’ve actually dived off Port Douglas and done the Great Barrier Reef, which was astonishing to me. It’s been the benchmark. That was 35 years

ago. Back then, it was astonishing. In 2013, 10 or 12 years ago, I couldn’t recognise it. It was a desert: a white, bleached, dead desert of death. Now 80% of the largest organism that’s ever grown on the world is dead. That’s just the tip of the iceberg, because that’s one of the foundational pieces of the entire ecosystem of the oceans, and it’s basically dead now.

That was in 2013, and that was when I really paid attention to what the hell we were doing, because I was seeing it. I had sort of been seeing it over time: “These reefs don’t look so great. This reef doesn’t look so great.” That was from Malaysia, the Philippines, Indonesia, the Mediterranean — all over the world. I’d been seeing little bits and pieces and wondering why it didn’t look so great. I thought, “This reef isn’t so good,” or, “That island isn’t so good.” Turns out, it’s the entire ocean. The entire ocean has been completely decimated. What are we going to do about this?

What should we be teaching ourselves from this lesson called a dying ocean? Well, to get rid of the humans would be a start. We’re the problem. What we’re doing is the problem. Being here is the problem. It’s one reason we don’t have kids. Not the primary reason, but one of them. We could have had a kid, I suppose, but bringing a human into a place already overpopulated with humans is a bad idea. Not that biological drive isn’t going to drive more humans to have more humans, but there are ways to do it properly. We do not need 8 billion people, or soon 9 billion, on the planet. One billion is plenty. That’s

sustainable. Every biologist will tell you the same thing. Every real scientist will tell you the same thing. I grew up with parents who were biologists, so we were schooled in this before it was a thing. They saw the signs. They saw what was happening in the 70s and 80s. But now we know. Science is so slow in confirming because you have to disprove your theories. People don’t know this, but you have to try to disprove your ideas. That’s good science. Good engineering is the same thing.

I have to prove that I’m wrong. I’m going to do everything I can to prove this is wrong. Most people are trying to validate why they think it’s right, and that’s a terrible thing to do, because it’s confirmation bias. You say, “I’ve created this thing. It’s the best thing in the world. It’s amazing.” That’s a terrible idea.

If I build an obstacle for obstacle racing, which I do a lot of, I’m trying to figure out how it can be wrong, how it can break, how it can create a problem, or how it can be dangerous. Most people don’t look at it that way. You are really focused on safety. I am, especially because my day job as a legal forensic expert is about risk, identifying risks, hazards and dangerous conditions.

I get this answer a lot: “This obstacle is fine because we’ve never seen something happen on it.” It’s like, how many times have people used it? How many users do you have? They’ll say, “We’ve been using this for three years, and we’ve had hundreds or thousands of people on it.” I’m thinking six, seven, eight Sigma would be better. Six Sigma is one in a million, and one in a million is still a bad idea when you get to a million, because something is going to happen. What if you get to 10 million? What if you get to 100 million? In obstacle racing, we’re way over 100 million obstacle completions. You have to start thinking in eight Sigma numbers. Do you ever

want a death? No. If you have 100 million people doing something, and one person could die, do you want that to happen on your watch? It’s going to happen. That’s what I’m doing. Most people say, “I’ve been doing this for 10 years and I’ve never seen it, so it must be okay.” No, it’s absolutely not okay. You’re looking at it wrong.

That’s the same logic. I had an opportunity to sit with an FAA administrator once, and they talked about the level of perfection required for flight to be safe. It wasn’t six Sigma. It wasn’t eight Sigma. It was a big number. People don’t really appreciate all the thought that goes into safety at scale in massive systems. I never really thought about how many hundreds of millions of people are participating in obstacle sports until this conversation. Put a number on it. The way I look at the numbers for safety is obstacle completions. Use

Spartan Race as an example. Let’s say they have 400,000 finishes a year — people finishing an event — and on average they’re going through 30 obstacles. Do the math. That’s 12 million obstacle completions a year, and they’ve been doing it for over 10 years. That’s 120 million obstacle completions. When you get to numbers like that, the data you have is significant. That’s good data. The standard deviations are low. The averages are good. You start to understand what can happen. We work very closely with Spartan. Joe is a friend of mine. He’s the owner, and Giles is the CEO. He’s on my board, so we work constantly together and have these exact discussions. Giles and I

will be in meetings where we hear things like, “But we’ve never seen anything happen.” We’ll be in a group of people who maybe have had thousands, maybe even tens of thousands of obstacle completions, and Giles and I look at each other and go, “Not 120 million.” It’s a different number. We’re talking about different things here. My job — my now job, my future ex-president job — is partly that. It’s to help guide some of the things that matter for people.

It’s about the humans. What’s going to hurt someone? We need to address that. What’s going to excite someone? We need to do that too. What’s going to motivate someone? The fundamental premise of this whole thing, which is a good thing for everyone, is sort of the Olympic purpose. The Olympics is a movement. Most people don’t know that. It’s the Olympic movement. It’s not a company, not an event, not a games. It’s a movement. The purpose of the movement, paraphrasing it, is to make better humans through sport. If you do that, you actually make a better planet, because a better human is going to be

doing things. A better human is going to be looking after everything, including the planet. In my world, making better humans through sport has a wider implication. The good thing about the Olympic movement is that it’s big. Five billion people will be watching the Games, maybe six billion will be watching LA. That’s most of the human population. You can influence a lot of people by doing good things. People get motivated during a Games. You remember from Torino. It’s an incredible experience. It’s like, “This is amazing. We should do this every year.” Paris was incredible. LA is going to be as good in a different way, and maybe better in other ways. We

have this platform to do amazing things and make better people. If we make better people, we make a better planet. That’s why sport matters, and that’s why I find sport incredibly useful for creating a legacy of good. That’s a bigger question: what do you do at the end? We know what the destination is, but what happens after that? We’re gone. What happens now? If we can leave a legacy for good, we did something.

We changed something. Do something. Don’t do nothing. We have to do something. I think the question is also how we experience being. Just doing something isn’t always enough. Sometimes we have to be better, which could mean doing less, changing less, consuming less, thinking about how to produce better humans in educational systems and physically improving our world. I like that legacy. Let’s do that. Let’s do more of that. Let’s do it, and let’s remember the humans.

Eighty percent of humans have not enough of anything: not enough food, not enough stuff, not enough shelter, not enough water, not enough anything. Eighty percent of our population — when I say “us,” I mean us as a species — most of our species are destitute and have terrible conditions. We are the ones who have the opportunity to help make that difference. They do not. They cannot get enough water. They’re walking eight miles a day to get water, and not enough of it. We don’t have to do that. I can walk one foot, turn my tap on and get drinking water that I can shower in, which is a stupid thing to do, by the way. We shower

in drinking water. How crazy is that? Wow. I guess I haven’t given it any thought, which is part of the purpose of a conversation like this: to cause us to think. I can’t tell you how happy I am to get on a conversation with you. This has been a great conversation about life, performance, dedication, curiosity, the Olympics, the movement that makes better humans and your part in it. I’m grateful that there are people like you communicating, collaborating and building a better world. Thank you. All of us.

Thank you, Mark. Hey, thanks for listening to The Parallel Entrepreneur, and thank you to our sponsors, partners and the amazing team behind the scenes who help make these conversations possible. If today’s episode sparks something for you, be sure to follow, subscribe and please share it. Learn about our growing community at parallelentrepreneur.com, including details on our mastermind and companion programmes designed to help you align, grow and thrive across multiple ventures. And of course, gratitude to every visionary guest who trusts us to share their story. Until next time, keep building in parallel.

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