110: 10x World Record Breakers Business Hacks for PEAK Performance – Find your Everest with Colin O’Brady

Today, I’m joined by Colin O’Brady, an endurance athlete, New York Times bestselling author, and a 10-time world record-breaking explorer who became the first person in history to complete a solo crossing of Antarctica in 2018.

In 2008, Colin suffered a devastating burn injury while backpacking in Thailand. Doctors told him he was unlikely to walk normally again. But by March 2009, he was back to winning triathlons. Colin has also summited Mount Everest (twice), rowed across the Drake Passage, and set the record for the fastest summiting of the 50 highest points in each U.S. state.

Colin’s TEDx talk, “Change Your Mindset, Achieve Anything” has been viewed more than 3 million times, while his book “The Impossible First” earned him a spot on the New York Times bestseller list. His most recent book, The 12 Hour Walk, aims to help readers overcome their limiting mindsets.

In today’s packed episode, you’ll hear Colin tell tales of crossing Antarctica, climbing Everest, and leaving billionaire hedge fund managers speechless. You’ll also get insight on how to conquer your mental roadblocks, how to find your purpose in life, and how to unlock a new level of perseverance in both your personal and professional life.

Inspiring Quotes

• “As humans, we all sit on these reservoirs of untapped potential to achieve really extraordinary things. But it fundamentally does come down to how we react to inevitable setbacks.” – Colin O’Brady

• “Massive setback leads to great learning. Great learning leads to more resilience. More resilience leads to all the things that have happened in my life.” – Colin O’Brady

• “Failure + perseverance = success.” – Colin O’Brady

• “Winners lose the most.” – Colin O’Brady

• “The limiting beliefs in our pervasive culture really box people in.” – Colin O’Brady

• “Life is all dictated on how we react to things.” – Colin O’Brady

• “You look at all the research on happiness and fulfillment — from the academics to the anecdotes — and it all comes back to community.” – Colin O’Brady

• “Relationships are such a force multiplier to growth.” – Colin O’Brady

• “It doesn’t matter how peak of condition you are in or how good your nutrition is if you don’t have the mindset to get there.” – Colin O’Brady

• “We are the stories that we tell ourselves.” – Colin O’Brady

• “The top of one mountain is really just the bottom of the next.” – Colin O’Brady

• Adventures of a 10-time world record-breaker
• The transformative potential of major setbacks
• How situational reactions shape your life
• Entrepreneurship and professional adventuring
• How Colin raised $500,000 at age 28
• Why to invest in community
• Is your work aligned with your purpose?
• How to find your “Mount Everest” in life
• Overcoming limitations with your mind
• How to push through roadblocks
• A mental framework for choosing your adventures
• Why do people do crazy sh*t?

Brad Weimert: Colin O’Brady, welcome to Austin, man. It’s great to see you.

Colin O’Brady: Great to be here with you, my friend. Always a pleasure.

Brad Weimert: Yeah. I anticipated doing this remotely at some point in time, and I was pleasantly surprised two days ago to find out that you were in town, and we could just squeeze it in.

Colin O’Brady: I know. It’s perfect. It’s always best to do it in person. Always great to see you. So, here we are.

Brad Weimert: Yeah. And the good and bad points to this or that you are here because you had an expedition cut short with a near-death experience. So, I want to get back to that part of it but for those that have not met you, don’t know about you, you are a professional triathlete. You hold ten world records or have broken ten world records. The Explorers Grand Slam speed record, which is the highest peak on every continent plus each of the poles, faster than anybody else in the world crossed Antarctica alone, pulling your own sh*t, a 350-pound plus sled behind you for 54 days, first human ever to do that, amongst a litany of other things. So, I want to get into a bunch of that sh*t but first and foremost, before we talk background, what of those adventures, or which of your adventures has been the most impactful for you?

Colin O’Brady: Yeah. I mean, each adventure has certainly had its own experiences, lessons learned. I know we’re going to be talking a lot about business and entrepreneurship. A lot of it’s been like, “Hey, I want to go to the North Pole, South Pole. I want to go to the Summit of Everest.” Like, “Sh*t, I don’t have any money. Like, how do I build a brand? How do I create around that to actually go live that and have impact at scale?” I know we’ll talk a lot about that but I think on a personal level, the solar crossing of Antarctica in 2018, I think, for a number of reasons was probably the most impactful one, spending 54 days alone in an empty white abyss. If you don’t come out of that somehow changed, then there’s probably something wrong with you. So, that was a deep cut personally on an internal journey. And that also coincided with that expedition and a lot of the work that I had done leading up to it ended up having a massive effect in the press and the media. I became the first person in history to complete that crossing, something that people had tried for 100 years unsuccessfully.

And as a result of that, sort of perfect storm of press and media and brand and where we positioned the story and things like that, it ended up being viewed by over 2 billion people in terms of media impressions, which was the most widely viewed expedition in modern history. And so, as a result of that, there was a sort of net multiplier effect on a lot of hard work that I put in as a professional athlete, sort of leading to not just my ability to successfully complete that. I feel like I had to pull on every tool that I’d learned as a professional athlete, basically, for my whole life but also, from a business sense, it was this force multiplier and really opening a lot of doors in an exponential way. But it’s kind of the classic we all hear this in entrepreneurship, an overnight success, ten years in the making. It’s definitely that same type of feeling, which it was a huge moment in my life, and it continues to have a ripple effect. But it was built on the back of a lot of hard work that went to finally get to that really apex moment.

Brad Weimert: Yeah. And I want to talk about a bunch of those things because there’s so much to unpack with both the endurance side of it, the adventurer and expedition side of it, the entrepreneurship side of it. One of the things that you just highlighted that I think is really relevant for people to grasp is there was sort of an era of humanity where we were exploring parts of the world that had never been touched, in a lot of the time with no f*cking resources. Like, the initial attempts to cross Antarctica wore wool and dogs with you and eating fat to survive and crazy sh*t. And we’re in a different space where it’s almost impossible to find things that haven’t been done but even more so to get attention for them, right? People don’t pay attention to those things the same way. So, I want to get into that but before we do, I want to talk a little bit about how you started. So, like, what got you into endurance in the first place? Because you started as a triathlete. That was the beginning of the endurance stuff, right?

Colin O’Brady: It actually goes back a little bit further than that. I mean, it goes back to early childhood. When I was five years old, I was running around outside this pool deck and there happened to be swim lessons but also a swim meet happening. And I was a rambunctious kid with a ton of energy. My mom was really looking for the sport that she could put me in, A, that didn’t cost very much, we didn’t have a lot of money as a kid but, B, that would just use up as much energy as possible. And like I love team sports and I actually played soccer at a high level but baseball, you’re kind of standing around a lot or things like that. She’s like, “Swimming? Wait, you’re just like exercising the whole time? This must burn the maximum amount of calories.” So, she put me into a swim race. I won that first little five and under, the little kids swim race, and ended up swimming all the way through college. So, I was a nationally ranked swimmer in high school. I was a Division 1 collegiate swimmer at Yale, which then, of course, as you mentioned, sort of led into triathlon.

But, yeah, the early days were really around swimming but a big shift in my life that I know that you have heard this story before but really happened after college and before triathlon, which was I decided after college to travel around the world for a year. You know, I didn’t have very much money. I saved up painting houses as my first entrepreneurship venture. I was a 15-year-old kid painting houses, and I kept that summer job through high school and college, saving up a few thousand bucks going, “Man, when I graduate from college, I’m going to go travel around the world.”

Brad Weimert: What company was that?

Colin O’Brady: It was just a company that me and my childhood buddy started called Precision Painting.

Brad Weimert: Oh, nice. So, it’s just you guys doing it.

Colin O’Brady: Yeah. So, we spent one year doing what was called like college pro or something like that painting or it’s like basically high school and college kids painting houses. We did that for one summer working for somebody else. And we looked at each other and we’re like, “Dude, barrier to entry for doing this ourselves is not high. Let’s buy a paint sprayer, let’s buy a couple of ladders and things like that and just do it ourselves and not have to give them the cut.” And it worked out for us because his dad was a contractor. So, that gave us a little bit of our first pipeline to be able to get a couple of jobs. But then after that, like when we’re 16, 17, 18, we were able to like, you know, we had enough like, “Hey, we painted these houses in your neighborhood. Do you want to, you know?” I think we were pretty good at it for our age and experience level.

Brad Weimert: Yeah, that’s awesome. A very good friend of mine, who’s also been on the show, Cameron Herold, was running College Pro Painters for years. And that as a business model is fascinating because it’s a summer job. So, they build up this monster workforce across the continent and then they all leave. It’s crazy. And some of them leave and do what you did, which is like, “I’ll just take the model. I can do this myself,” which is the most entrepreneurial of them, right? It’s sort of like franchise versus doing it yourself.

Colin O’Brady: Correct. Yeah. No, I mean, it was a great way to cut our teeth. And then also it was a great way as like it was the classic like your high school college kid, like, “Okay. I get a summer job working in the grocery store or this internship or whatever.” And I was like, “Wait. We can do this.” For us, it was like, “Wait, we can paint a house and make $3,000 or $4,000 or $5,000 ourselves, not like hourly, and then go do whatever we want. Manage our own time.” We’re like, “This working for ourselves thing is pretty great.” Even though it’s hard work, right, it just felt better for us. It definitely was like that was pretty obvious to me as a young person that I wanted my life to end up somehow directionally there. But, yeah, so after college, I took a backpack, a surfboard, and a few thousand bucks I’d saved up and went and traveled around the world. My hope is to travel for a year, barely any money, shoestring budget, sleeping on youth hostels and hitchhiking around and trying to save a little money to have some beers at night so I could have some fun. But, like, even it was like, on the cheap. On the cheap was an amazing experience.

And then I was in Thailand, actually, and I ended up getting severely burned in a fire. So, I was foolishly jumping a flaming jump rope of all things, wrapped that rope around my legs, lit my body on fire completely to my neck. Ended up jumping in the ocean, which saved my life but not before about 25% of my body was severely burned, predominant in my legs and feet. And no proper hospitals on this tiny little island. There’s a cat running around my chest and across my bed in this ICU. And I was in a bad state but worst of all, being an athlete to your question about endurance was the doctor walked in after a couple of days and looked me in the eye and I said, “Hey, man, like, I hate to tell you this but you’re so badly burned around your ankles, your knees, your ligaments, we don’t think that you’ll probably ever regain full mobility. You’ll probably never be able to walk normally again.” And it was just obviously there’s a lot of pain, it was horrible, but like, there’s nothing like being in your body as a person, and that’s sort of like my identity in the world. I have been a Division 1 athlete right before that and it’s all of a sudden like, boom, you made one stupid mistake, kid, and like that’s all over.

And so, that was an incredibly dark period of my life. I just remember that sinking feeling inside of myself. But fortunately, my mother, she arrived over to the Thai hospital. She sat with me for weeks and weeks in that Thai hospital and really wrapped me in this sort of air of positivity, of saying, “Hey, yeah, you screwed up. We’re not going to sugarcoat this. You’re lying here with your legs bandaged in a wheelchair. But what do you want to do when you get out of here? Like, let’s set a goal.” And I think that actually does tie back to sort of those initial phases of entrepreneurship or even in the middle of it where like sh*t’s going to go wrong and you’re going to make mistakes. Like, I made a massive mistake here. And my set point of that as a young person was like, “Man, I screwed up,” just downward spiral of negativity. And thankfully my mother came back to me and was like, “Sure. Yep, this is a tough spot but let’s learn from it. Let’s grow from it. Like, where can we go from here?” And the difference between those two things is really the difference in my life. I wouldn’t be sitting here having this conversation with you with ten world records otherwise.

But long story short, she’s like, “If you could do anything when you get out of here, what would you do?” And I was like, closed my eyes, kind of visualize, and I saw myself in my own visualization crossing a finish line of a triathlon, which is not something I’d ever done before. I was a swimmer, of course, but I never like biked or run competitively. But for whatever reason, that vision was what I upheld is like me being back in my body, able-bodied, strong, etcetera, again. And so, instead of her saying, “Yeah, that’s a ridiculous goal. Don’t go for it,” which again, as entrepreneurs, we’ve probably heard sometimes from our close community of friends like, “Hey, dream small or get a real job. What if that doesn’t work out?” Like, that’s, unfortunately, the limiting beliefs in our pervasive culture really boxed people in. And I applaud anyone who’s listening to this, who’s an entrepreneur who’s fighting against not only their own interior dialog but the dialog of colleagues, parents, relatives who are saying, “No, no, no.”

But my mom, to her credit, in this moment, she’s also an entrepreneur, says to me, “Great. You’re going to finish a triathlon.” I’m looking down. I can’t walk, right? But there is a long road to recovery over 18 months, learning how to walk again, eventually taking a job in Chicago in commodities, trading, and finance, using my education at least to begin my career in that which didn’t stick and then signing up for the Chicago triathlon. And 18 months after I was burned in the fire and 18 months after being told I would never walk again normally, this was back in 2008, I raced a Chicago triathlon and not only finished the race, which was my goal but I actually ended up winning the entire Chicago Triathlon racing first out of 5,000 people. And your question is like when I get endurance, true at five as a swimmer. That was massive all the way through college. That’s a big part of my life. But you’re 21, 22 years old after college, just bad accident and you think, like, “Okay. Like that’s where doing sports like ends.” I didn’t make the Olympics in swimming. I’m not Michael Phelps. Like, that’s the end of the road.

And all of a sudden, I win this triathlon. And it was an interesting moment for me. It wasn’t just like I pat myself on the back of like, “Well, I guess I’m just some world-class athlete. I’m amazing. Like, I’m great.” Instead, it’s like my mind goes back to that Thai hospital wondering what would have happened had my mom not forced me to look towards that future and set this measurable goal, right? Like, what would have happened otherwise? And furthermore, in all my thinking about this over time, this is 16 years ago, like I realized that I fundamentally don’t believe that I have something different than you or anyone else listening. I fundamentally believe that as humans, we all sit on these reservoirs of untapped potential to achieve really extraordinary things. But it fundamentally does come down to how do we react to inevitable setbacks. How do we pivot and evolve? That was such a sliding door moment for me. And had it not been for my mother, I probably would have just been like, “Yep, I’m never going to be the same again,” kind of wallowed, probably bounced around for a couple of years, like aimless and hurt.

Instead, she focused me. I got on that. And then that has obviously led to triathlon, which led to me to being a professional triathlete for six or seven years, racing for the US national team all over the world. And then now here I am 16 years later, it’s all these expeditions and world records and things.

Brad Weimert: Well, there’s a lot in there and there’s also a lot in between that and now in those 16 years. And there are, I think, a lot of questions around mental fortitude, perspective, and given that we are all humans, how we condition that stuff. And I want to ask some of those things, but you hit on it and I think that the curious question is, where did you land in terms of where you’d be if your mother wasn’t there?

Colin O’Brady: Yeah. I mean, I think that, of course, I have some intrinsic motivation within myself. But I think that in deep tragedy or in massive setbacks in this case, like, all of a sudden not recognizing my own body, which is something I’ve been able to count on for so long and backing up for a second. So, I have an economics degree from Yale. That’s where I swam in college. All my friends, it’s Yale 2006, economics degree. I come from like a low-income background. Most of these kids are coming from prep schools or blue blood kind of situations and everyone, 30% of my graduating class in 2006 went and worked on Wall Street. This is pre-credit crisis. This is not to say that Wall Street’s still not booming but it’s like really like, you know.

Brad Weimert: That was it.

Colin O’Brady: Yeah. Like, paved road to riches kind of scenario. And all those investment banks are recruiting kids, Yale, Economics degree. Do you want a job at Goldman Sachs, Morgan Stanley, Lehman Brothers you name it, right? And so, I’m not saying 30% of the economics majors, 30% of my entire graduating class, history majors, English majors, like, they’ll take anybody like at this point, let alone probably 97% of economics majors, which is what I was, were headed down that path. So, when I raised my hand and I said, “No, actually, guys, I’m going to do my summer job painting houses, and then I’m going to take a surfboard and backpack and go, like bum around like Australia and Fiji and like Thailand. Like, have fun with your corporate jobs.” There was a lot of pushback again from my peers. They were saying to me like, “Dude, you’re missing it. Yeah, like it’s going to be hard work in our early 20s but by the time we’re this age, we’re all going to have so much money.” It’s like a secured future in a lot of senses, right?

And we all know from entrepreneurship the numbers can be even higher but it’s far from a secure future. It’s like boom or bust or try a bunch of things and fail and then finally figure something out or whatever, but anyways, me in saying that. So, then I go down that path and for a few months I’ve got like all these epic, like they’re at their offices in New York City like grinding and I’m on the beach with some pretty girl in Fiji. I ended up meeting my wife in Fiji on that trip but very sudden like moments like, “I’m living like I’m living life.” And I was like, “My thesis was correct.” And then I burned myself in this fire. And it was this moment where not only was my own sort of physical mind, body, spirit pretty crushed by the trauma, the actual physical trauma of the event but it also, of course, brought up all those doubts of, “See, I told you so.” All my friends being like, “Oh bro, not only did you miss the onramp to this lucrative career path, but you can’t even walk. So, like, you’re like ten times or 100 times or 1,000 times worse off than you would have been. You idiot. We told you, do the thing that you should do in this moment.”

And so, obviously, the way life has turned out, I feel very, in fact, in a lot of ways, the burn accident was one of the greatest teachers and the resilience from that. But had I not had that guidance from my mother, right, I wonder. It’s an open-ended question but I certainly wouldn’t have raced that triathlon. I certainly wouldn’t have won that triathlon, become a professional triathlete. And if I hadn’t done all those things, I most likely wouldn’t have set ten world records in endurance and expedition. So, that would be drastically different. But moreover, if you go back to that acute moment, like what would have been the ripple effect in the other directions of sliding doors, like one like, “Oh, use this as a growth moment. Massive setback leads to great learning. Great learning leads to more resilience. More resilience leads to all the things that have happened in my life.” Versus massive setback, proves your doubters right. Those doubters have the last say. You start feeling negative about yourself and then you kind of return to the world, the tail between your legs, and some injured banged-up legs and who are, you know.

Brad Weimert: Doing heroin on the street corner.

Colin O’Brady: Right. So, I mean, exactly.

Brad Weimert: I mean, I don’t know.

Colin O’Brady: Yeah. So, it’s interesting and I think that life really is that way, not just for tragedy, but it’s an easy one to point to, which is I believe that life is all dictated on how we react to things. You know, the stories that we overlay on said experience and our own personal reactions to it, which is, you can be a VC trying to invest in a business, right? And you go, “Why would I invest in this guy? He failed at his last business like he failed his last business. This guy’s a loser. This guy’s not going to get it right.” There’s a lot of VCs that have the opposite thesis, right? They would go like, “I’m going to invest in this guy because this guy failed at his last business, but he’s still charismatic, has new ideas in front of me. This is a cogent for whatever philosophy of whatever business this is. And I bet that dude learned so much from this experience, so much so that he’s starting another experience and he can apply that failure or that setback to that.”

Brad Weimert: And he’s got a chip on his shoulder.

Colin O’Brady: He’s got a chip on his shoulder.

Brad Weimert: And he’s like, “Sh*t, I better figure it out this time. I’m so frustrated that it didn’t work. I’m so wound up to prove myself that I’m going to make it happen.”

Colin O’Brady: Right. And so, those two profiles or avatars we’re talking about like that’s really if you really boil that down below the story about my business failing, this is like, “Oh, your reaction to failure was either A or B.” And those two things dictate so much and that’s true in the story that I just shared, as well as many other moments in my life for sure.

Brad Weimert: So, you go from professional triathlete to professional adventurer, really. And you had professional triathlete, unlike despite it being equally or much more difficult than many other professional arenas in sports, it is not rewarded the same way, and it does not have the same fanfare that other professional sports do. So, you can have a career in it but certainly, you’re not getting obnoxiously wealthy like you would in the NBA or NFL.

Colin O’Brady: No, no, no. It’s like I was happy to just have my expenses covered. It’s more like sleeping on friends’ couches, eating peanut butter and jelly sandwiches, trying to rustle up enough money to travel to the next corner of the world. I did over those five or six years race in 25 countries, six different continents. For me, the adventure was worth it as long as I could just, like, kind of like just barely make ends meet. But it is absolutely not like, “Oh, and then I retired with my big house or whatever.” At some point you’re like, “Okay. I’m just literally getting by.” And again, that comes down to belief in process. For me, I was like, “Yeah. I get to push my body.” I was super curious on the other side of that burn accident of like, “Oh, well, what are my limits then? Like, what are my physical limitations? How much more can I push my mind, body, and soul?” And professional endurance sports was a great arena to do that. Like, quite literally, racing against the best guys in the world week in and week out, and of course training. And then also the adventure of the life experience of like going out there.

And I say this to young entrepreneurs all the time, which is one of my favorite groups of people to talk about, which is sometimes people think, “Oh, if I don’t take that well-trodden path or I leave to travel for a year or I find this mentor and he like wants me to work for him for a year.” And I was like, “Yeah, because you’re learning something. Like, you’re making yourself different in some unique way.” And I always felt whether I was going to return to entrepreneurship and I didn’t know that I’d be a professional adventurer in the early days of triathlon. But I had this belief of even though I’m not making a lot of money right now, I am banking so many different life experiences, not just the personal development and growth of pushing my body but I was like, I race in Zimbabwe twice and Estonia and Latvia and places I wouldn’t like ever go to and exploring these cultures and interacting, all those things. It’s like I don’t know exactly how those dots are going to connect. And moving forward, I love the Steve Jobs quote, which is, “You don’t know the dots going forward. You can connect them going backwards.”

And it was this belief is like every day I wake up and I have my bike in Mombasa, Kenya, and I’m riding it around like that’s going to be something interesting in the future and how I apply it. And so, that was always my sort of belief system in the process of that, of those experiences cumulatively unlocking some sort of creative impulse, introducing me to some interesting person or people. And, I mean, that’s true at scale, not just like one or two things. I mean, just like all those things have stacked on each other.

Brad Weimert: Bro, I mean, that is a very insightful approach for an early 20-year-old person. Most people that go down that path do it fairly frivolously. And most entrepreneurs throughout their entire life have a hard time doing that, even in a silo, meaning they have a hard time saying, “Hey, I know that I want to learn business. I even know that I want to learn this industry but I’m not willing to work for free. I’m not willing to just put the time in unaware of what the outcome might be,” instead of the approach that you just said, which is, “Hey, I’m learning, I’m growing, I know that these experiences are going to contribute to the ultimate outcome on a long enough time horizon.” And most entrepreneurs fail to do that, much less humans. The next chapter for you is adventure. Like, real f*cking crazy adventure like things that nobody else in the world has done adventure. Tell me about the – I want the basics here because I know you have an amazing book, The Impossible First. I’m going to highlight that a little bit more, when we get to that chapter of life but some of these stories are in there.

But the introduction into adventure initially, how did you pick? First off, what’s the Explorers Grand Slam? Why did you pick it? And why on earth did you think this was the thing that you should be doing with your time knowing that there’s no paycheck associated? You’re just like, “Hey, I’m going to carve out years to try to do this.”

Colin O’Brady: Yeah. It was an interesting moment. So, I had been trying to make the Olympics in triathlon. That was like my stated goal. And it became clear to me not too long before the 2016 Rio Olympics. I was right on sort of the fringe of that but it was looking less likely than likely. It was like right in the conversation, not like some random person. I was like right in the mix but it was kind of like, “I might not quite get over the hump.” And that is what it is. It was such a great part of my journey. And so, I started thinking like, “What’s next? Like, what do I really deeply, deeply care about?” And it was right around the time that I got engaged in 2014 and I was standing on top of a mountain top where I got engaged with my then fiancée, Jenna, who you’ve met. And I’m sitting there just kind of like thinking about life, like just thinking about kind of the next chapter of life. It’s an interesting inflection point, right? You’re like making this commitment, and you’re like, “So, what do we want to do? What do we care about? What are our values?”

And similarly, I guess, in a lot of ways of my mother’s visualization for me in that Thai hospital, “What do you want to do when you get out of here?” and I have now kind of coined this phrase that I call a possible mindset. I write about it in my book, The 12-Hour Walk, and I define that as a sort of unlocking limitless potential in your own mind, like what could you do if there were no limitations, if you allowed yourself no limitations, essentially. And so, I was like, “Okay. Forget about money realistic-ness of anything. Like, if I could do anything, what would it be?” And as a kid, I’d always dreamed about climbing Mt. Everest. I grew up in the Pacific Northwest staring at Mt. Hood. I always loved the outdoors and loved mountains. And there was this little boy inside of me that was always kind of like, “I want to go to the Himalayas. I want to climb Mt. Everest.” I remember reading Jon Krakauer’s Into Thin Air in like the late 90s when I was in high school and just being, it’s crazy, because the book is about eight people dying on Everest but for whatever reason, I was like, “I got to go there one day.”

So, that was really sort of just in my mind and in the series of this conversation and sort of tapping into like I said, this positive mindset and an empowered way of thinking that unlocks a life of limitless possibilities, I said to myself, “Man, I want to climb Everest.” And right around that same time, I was aware of the Seven Summits, which is the tallest mountain on each of the seven continents, which of course includes Mt. Everest. And then I had heard about the even bigger layer of that, which is, well, then you throw in the North Pole and the South Pole, and that’s known as the Explorers Grand Slam. So, I started like researching this just out of curiosity, and I found out that only 50 people in history had ever completed the Explorers Grand Slam. Now, my biggest even though it’s funny, like I hadn’t done a lot of climbing or mountaineering and of course, to climb Mt. Everest, most people’s initial harder than mine would be like, “Well, sh*t, I better learn how to climb mountains.” Right?

Brad Weimert: Yes.

Colin O’Brady: And that’s obvious. But for me, with a growth mindset, with something I’ve always applied with, even with the triathlons like I hadn’t raced triathlon before and then I won a triathlon. Like, that gave me the confidence to go like, “Oh, I can learn the thing.” Will it take time? Do I need to practice it? Do I need to understand the skills? Absolutely. But there’s no doubt in my mind that I am capable, and I believe, honestly, we are all capable of saying, “Yeah, that skill over there, I’ve never rowed a boat. I want to learn how to row a boat. I’ve never run in a race before. Okay. I’m going to start jogging.” Like, we can learn. Like, those things, we can learn. But I was like, “What’s my actual biggest barrier to doing this?” And this directly ties to entrepreneurship. I was like, “I can’t afford it.” Like, I’ve been a professional triathlete just hand them out paycheck to paycheck. Like, Everest by itself costs, you know, now it costs well over $100,000 but at the time, it was like 50K, 60K to do Everest. Like, who has just 60K rattling around just go climb a mountain for like a couple of months? Like, very few people, right?

Brad Weimert: Particularly if you’re a professional triathlon.

Colin O’Brady: Exactly. Right. That phase of my life like I was in my late 20s and was like, “I have this dream. I believe I can actually do the thing,” which is a lot of people would be like, “Well, that seems the obvious barrier. What are you going to climb Everest? You never climbed a mountain?” but I was like, “No, that I’ve got.”

Brad Weimert: Well, let me pause you on that for a second because those are two different things, right? One is the capability of doing the activity and the other is the fundraising, which, by the way, is just another activity that you may or may not have the capacity to do or a skill set to do, but in terms of capabilities, you gave us one data point of, “Hey, this one time, I’ve never done a triathlon before and then I won it.” Was that enough, the one data point or did you have other? I have a general narrative internally that is, as data points stack up, your confidence typically does, right? The more references you have to something, the more likely you are to be able to execute on that thing. But in negative situations, sometimes all it takes is one reference point that pulls you in the wrong direction.

Colin O’Brady: Totally. I mean, it’s the classic like you get like 100 really positive Instagram comment, “Oh, that’s so cool. Great. Impressive,” whatever, and one like negi comment and you can only think like the negative. It has such a higher compounding effect just on our own psychology.

Brad Weimert: So stronger. Yeah, totally.

Colin O’Brady: No, there’s no doubt about that. I think, honestly, there’s been all sorts of data points and sort of subtle things that I can point to over time, both that I was conscious of in that moment and also unconscious of. When I look back, I was like public school kid from Portland, Oregon. I ended up at Yale like, okay, that’s like against the odds, like figure that out. When I got there and there was a bunch of prep school kids and I was like, “Oh, man, like, these kids are smarter than me.” But I figured it out like how to get through that and navigate that and ultimately thrive I would say, but it wasn’t like, “Oh, I was born for this. This is like my path in the world.” And so, I think that there is, again, there’s tons of examples, but there’s enough examples of like, “Oh, I don’t fit here. Oh, this isn’t like my main thing, but let me figure it out,” which I think is great. I mean, even in the painting example. It’s like we didn’t know how to paint then we learned how to do it for a few months, and then pretty quickly we’re like, “Oh, we don’t have to keep doing this for somebody else. We can just do this ourselves.” We have the confidence to walk up to somebody and be like, “We know how to paint houses now.”

And so, I think that growth mindset says, like, “I might not know this right now but I can learn and grow towards that.” And I think that that is true for almost all things, and that we don’t really have these innate like set points, but it’s easy in our mind to think differently. So, that’s the way that I apply that but it is funny when I really, even now think back into that moment when I was dreaming up this Explorers Grand Slam 2014-2015, I still, in this moment when I bring myself back there, have this like high level of confidence of climbing the mountains. And it’s not that I had a low level of confidence of the fundraising. I was like, “Man, that’s going to be like hard work and like we’ll see. Like, we’ll see if we can pull that off.” But here was my strategy and this I know you guys talk a lot about sales, a lot about marketing, etcetera. My decision matrix went like this, “I want to climb Mt. Everest and like, man, it would be really cool to also go to the North and South Pole and climb all these other mountains. Like that’d be super cool just as a life experience. Okay. Hey, I want to do these things.”

And then I thought to myself, “Whoa. What’s standing in my way?” Well, if you really budget out that project, not just Everest, but you add in all those other mountains, you’re talking about like $500,000. Like, I mean, yes, Everest by itself is crazy expensive but those are like you add those other things like, okay, now, you’re talking about like half a million. I’m 28 years old. I don’t have a trust fund. I don’t think it’s like I’m sitting on like cash. And I’ve just been working a job that didn’t pay me other than just covering my expenses. So, I’ve got like $10,000 maybe to my name, period, like, saved up. So, somebody else is going to have to fund this. Like, that’s the only answer. And this is where most people stop. They’re like, “Okay, cool. You want to do this thing cost half a million dollars but you don’t have half a million dollars? Well, then you’re not going to do the thing.”

Brad Weimert: Yeah.

Colin O’Brady: I thought the other way around. I thought to myself, “Okay. Well, where’s the opportunity here?” If I were to just do this, like, for fun over a course of several years, no one’s going to care. Like, there’s no story in that. There’s no marketing value in that. There’s no product market fit, for lack of better things. However, if I can combine a couple of things that I’m actually authentically passionate about into something, can that actually have value enough in the market to equate to $500,000? So, I said to myself, “Oh, well setting the world record, being the fastest person in an elite way to actually do this Explorers Grand Slam, well, that all of a sudden elevates this project. It is wildly more interesting than, “Hey, can you give me money because I just feel like doing this thing.” Right?

Brad Weimert: Yeah.

Colin O’Brady: And in addition to that, and this is not just tacked on or inauthentic. And you and I have done some work with some schools. You know, you brought me into a charity here many years ago, which I loved working with in Austin.

Brad Weimert: Explore Austin.

Colin O’Brady: Explore Austin. Exactly. And those guys are amazing and derivative of my work, which I’m passionate about, like, “Hey, I as a kid benefited from being in the outdoors, moving my body and had wanted to start a nonprofit at the time around inspiring young people to get outside, move their bodies, and live active and healthy lives.” So, I was like, “Huh.” Now, there’s like in the ether. Explorers Grand Slam, need a half million dollars. Better story if I do it as a world record but if there’s a charitable component, which is really something that’s authentic to me, not tacking. When people tack that on, you can see right through it. But it’s like, “Oh, that’s actually something I want to do anyways. Great. Oh, this could be a force multiplier in creating that.” So, all of a sudden, we have like the beginnings of a business idea. But I’ll share a story here because I was like, “Oh.” Maybe the answer is like, “Oh,” and then it was just so easy. Well, it wasn’t. Then we look at ourselves and go, “What do we have? Not what we don’t. We don’t have 500K. We don’t have a big Rolodex. We don’t have experience.”

And that’s the time that’s Jenna and I doing this together. We have no idea how to start a nonprofit. These are all things we don’t have. But what do we have? Okay. We have $10,000. Okay. It’s not zero. It’s not a lot. It’s not 500K. We have $10,000. So, we can invest $10,000 into something in ourselves, right? And we have Google and the Internet and like a couple of laptops, right? So, there’s a lot of answers that can be found out there. How do you raise money? How do you start a 501(c)(3) nonprofit? Oh, you need this form and that form and all this bullsh*t to create the government hoops to do that. We’re learning. But we decide, we look at it and go, “You want to raise 500K? You better look professional. You better have a cohesive idea, a name, a brand. This needs to look legitimate.” And so, we decide, after all of our research, that the best way to spend our entire life savings is on a website and a set of brand materials and assets. So, that when somebody asks us about our – Jenna actually straight up looks at me and she goes, “You want to raise a half a million dollars? You better look like it. You better look the part.”

And to me, this comes back again, where if we’re talking to entrepreneurs here like this is why brand is important, right? This is why this is important. Our brains, if it’s investors, if it’s customers, if it’s clients, we are seeing so many inputs in our digital world that if you don’t look the part or it’s not professional or there’s no clear idea or thesis or value proposition, we pretty quickly just go like, “Okay, next,” like we just move on, right?

Brad Weimert: Today more than ever.

Colin O’Brady: Yeah. And so, again, I really applaud Jenna for helping me sift through all that. And she was like, “Spend the $10,000 on a website.” And so, we went into a creative agency, which we had never been into before, which was our first foray into that. And, of course, they quote us like, “Oh, we can build this brand and this and this idea and this logo and the website, whatever. It’s $75,000.” We’re like, “Cool, cool, cool. So, we have literally not one penny more than $10,000.” But they looked at us with a wink and a smile and glitter in her eye and decided to help us out, essentially. So, we build this amazing website and we built brand materials. It’s funny because it dates the story, but we actually built stuff that we printed out, like business cards with our logo on it. And we had like a little three sheet, little pamphlet thing that we could hand to people and meetings. We did all of that with no idea how we’re going to raise the money. We spent all of our money on that, and then we thought to ourselves, “Great. Now we can go do the thing.” And what happened? Nothing. Crickets.

We started emailing people or trying to set up meetings, having coffees with like whomever the hell we could talk to, whatever. And this is what we heard over and over again, “No.” “No.” “That’s not going to work.” “You’ve never climbed mountains. What are you talking about?” “You have 300 Twitter followers. You’re nobody,” like just all of the things as to why this didn’t make any sense for any market value.

Brad Weimert: Which, by the way, are really logical responses.

Colin O’Brady: Correct. So, there was definitely a sinking moment. I remember this feeling. Actually, it still rings true for me. I was like I said to Jenna right before we signed the deal with the creative agency, I was like, “Well, what if we build this website and do all this stuff? And like no one wants to give us money for the project?” And she just laughs at me in this. I appreciate the lightheartedness of this because this was like our whole safety net. And she laughs. She goes, “Well, at least we have a cool website.” So, fast forward, it’s a couple of months before I’m trying to leave to go and do the Explorers Grand Slam. We’ve now put 18 months of time of our full-time effort work into this. I was still racing triathlon enough to just keep the lights on, literally like pay my rent but I was transitioning away from that. So, I had a couple of sponsors in that space that were still like, again, base level of my costs. I was training but basically this we’re spending all of our time on and the runway was running out of that. That was about to end. We had no other jobs lined up, and I was supposed to leave in two months and we were still like 400K short.

Brad Weimert: Okay. So, what I’m hearing is that you have architected the whole plan logistically. You’ve said, “Hey, in order to do this and in order to break the record, I have to leave on this date. Here’s when I do this mountain, this mountain, this mountain, this mountain.” The whole thing is framed out but you have no money.

Colin O’Brady: Correct. And not only that, I’m not a big like act as if in terms of like, I don’t believe you should lie to anybody. However, the only way you do the Explorers Grand Slam in world record time is to actually set up like all the permitting and logistics and have things in place. It’s not just like, “Hey, on a whim, once I have the money, let me organize that,” right? And so, yes, we had to do things in parallel to try to raise the money but also plan all the things as if it is going to happen. And then this was the point where I definitely took pause in this moment, which is and we started a nonprofit initiative, which was amazing at the time. Obama was president. And we got actually through a series of ways, actually invited to the White House to present for Michelle Obama’s team, who is doing the big Let’s Move! campaign, which is a massive campaign around health. And also, that was like amazing. We’re like, “Oh, we’re getting some inroads there,” and because of that, beginning to be able to be invited to schools to speak to young kids about health and wellness but through the lens of this thing that I was about to do.

And I remember this feeling, I was actually speaking in front of a room of like third and fourth graders, and I was like, “And in two months, I’m leaving, and first I’m going to start in Antarctica, and I’m going to go to Nepal for Everest.” In the back of my mind, I’m like, “Bro, like, I don’t have enough money to get on like the first plane, let alone these things, and am I lying to ten-year-olds?” like that doesn’t feel good. But I wasn’t lying. It was just like, to your point, we had architected the entire thing. There was a date that we actually – it’s not like you can just, “Oh, you can start at random.” It has to start on a specific day because of weather and timing. It’s a very, very specific thing. So, I get invited by a friend of mine who’s been sort of watching me try to raise this money. He goes, “Hey, man. You should come to the spin class with me at 24 Hour Fitness.” I literally laughed out loud in his face. I was like, “Bro,” this is about ego getting the better of me. “I’m a professional athlete. You want me to go to a Sunday spin class at 24 Hour Fitness? Like, hilarious.”

He goes, “No, no, no, no. Honestly, man, like there’s this woman there. I’ve met her a couple of times. She’s super cool. I just think you would like her. She actually has set a world record. Like, you’re trying to set a world record. You should meet her.” It’s like whatever. And he was like, “Honestly, man, you should come.” And I literally laughed at him in this conversation but I woke up the next day and I was like, “You know what? I am grasping at straws here with my ego get the better of me. I was willing to meet anybody at this point.” And at this point, I swear a thousand people have said no to me. And so, I go to the spin class and he goes, “Hey, Colin. Meet Kathy. Kathy, Colin.” And I was like, “Hi, Kathy. I’m Colin,” and my friend, Angelo, he says to me like, “Tell her about your world record like she has a world record.” And she laughs it off. She’s probably in her mid-50s but she’s super fit. She’s like riding the spin bike already. The class hasn’t even started but she’s like sweating. She’s like, “All right.” She’s definitely hardcore getting after it but she’s like, “Oh my.” She set the world record in the 5K which is very impressive on the track. But she was like, “Oh my God, that was a million years ago. Angelo, that’s embarrassing to bring it up now,” and she’s just kind of like brushing it off but she’s like, “What are you up to? I don’t know anything about it.”

So, I give her this 30-second spiel just like, “Hey, doing the Explorers Grand Slam. This is why. This my nonprofit initiative.” Whatever. I’m not pitching there. I’m just literally just giving her like spin class about to start 30-second, just boom. And she’s like, “Oh that’s awesome. Good luck with that.” And then I get on my spin bike and I start spinning and I’m sitting there. I’m like sweating in the spin class thinking, “What am I doing here? Like, how did I end up here? Where did I go wrong?” And the class ends and as you do in the spin class, you take your towels, you wipe the bikes down or like whatever from your sweat. And this woman, Kathy, she waves me back over and she goes, “Oh, my God, I’ve been thinking about your project. Like, that is so cool. I can’t wait to root you on, like, that’s awesome.” And she was like, “You got to tell my husband about this like he loves stuff like this, too.” And I was like, “Okay. Yeah. Great.” And then she goes, “Oh, he’s here actually.” And she waves over this guy. They hadn’t been next to each other with the bikes. They were like separate in the class.

Brad Weimert: That’s weird.

Colin O’Brady: Doing their own thing, I guess, or maybe he arrived, I don’t know, but like they were not next to each other. So, I hadn’t met him when I walked in. And she waves this guy over. He walks over to me and he introduces himself, “Oh, hi, Mark. Mark, Colin, and nice to meet you.” And she goes, “Tell him the thing like tell him the thing. Tell him the exact same thing you told me.” And I was like, “Yeah, great.” So, 30-second spiel, Explorers Grand Slam. This is what it is. That’s why I’m doing it. You know, I’m excited about it. Kids health, blah blah blah.” And he looks at me and he goes, “Interesting.” He’s like, “That is amazing. Really cool.” He’s like, “By any chance, are you looking for sponsors for this project?” And my eyes like light up, obviously. I’m not thinking I’m pitching at all. I’m like, “Well, well, yeah. Actually, I am. We actually are looking for sponsors for this project.” And he’s like, “Great. You know, the company I work at, I think could probably help you.” And he goes, “Do you have a website or anything like that?” And I was like, “I sure do.” I was like, “Where do you work? Where do you work?” And he goes, “Oh, I work at Nike.”

And I’m like, “Oh my God, Nike.” I mean, I’m in Portland, Oregon. That’s like the dream of all dreams. Like, I obviously grew up in Portland so the shadow of Nike. But that’s on a global scale, if you’re a professional athlete that’s like the one. And he goes, “Let me get you a card and you can email me that website on Monday and then we can have a conversation.” I said, “Great.” And so, he shuffles through his gym bag. He pulls out his card. He hands it to me and I look down. It says, “Mark Parker, CEO, Nike.”

Brad Weimert: Crazy.

Colin O’Brady: And we spent a lot of time on this story but the thing is, yes, that changed my life. Yes, in the end, he saw the website. He invited me in. We had a meeting. Nike ends up sponsoring the project. Once they come on board, a couple of other partners come on board. We just barely raise the money. I pull up the project. I set the world record. And here we are now. But I tell that story to entrepreneurs for a specific reason, which is there are two interpretations of that story. “Oh, wow. Colin, you got lucky. Cool. You met the freaking CEO of Nike in a spin class at 24 Hour Fitness like bravo, like awesome.” That’s one interpretation and I think that’s a cynical interpretation of the story. The point to me in my lived experience is this, is that the 99 or the 999 other times that I failed where someone said, “No, this isn’t going to work,” those were at-bats. If I had been in that spin class on the first day of that, I didn’t have a polished elevator pitch. In fact, when I didn’t even think I was pitching, I was pitching but it was refined. I actually had 30 seconds of passionate, cogent material to share, and I invested my life savings into the website so that when that opportunity arose, I could actually do something with it, right?

So, for me, it’s again, it’s about failure but it’s like I believe that failure plus perseverance equals success. And those 999 nos that I got before the one yes from Mark Parker were all just warm-ups or in the process of getting to that one yes and yes, in business, more often than not, one person or one deal can really shift the potential of your business or where you’re headed. And so, for me, it’s a great lesson in the, I guess, resilience and perseverance, but also going like each one of these data points, each one of these lessons. Yeah, I pitched that guy. It didn’t work out, but it doesn’t mean it was a waste of time. Right? My mom said to me since I was a kid, “Luck comes to those who are prepared.” We were prepared in this moment, not just with the website, not just with this, but like when I went down and met with him in person, he’s like, “So, when is this start?” And I’m like, “It starts on December 26th.” It was like November 10th. He was like, “Oh wow. This is like happening like next month.” And he’s like, “Walk me through the logistics.” Not trying to poke holes, but I’m like, “First, I’m going here, this is the flight, I have this deposit down here, blah, blah.”

And he starts talking. He’s like, “Oh man. Like, this guy has put in a couple of years of work to be ready for this moment so that this meeting and if I write a check, he can go off and do it.” Not a, “Well, I have this idea. If I get funding, maybe I could do this because I was sort of thinking this.” It was like, no, I am doing this. And so, I mean, it’s kind of jump out of the plane and build the parachute on the way down type of mentality but I have found that that work and it certainly did in this instance for me.

Brad Weimert: There are a few big bullets out of that for me. The last one was back to this idea of you need to be taking the action the whole time, whether or not the outcome is guaranteed. And if you’re not doing that, you’re doing yourself a disservice. The second was a sales note, which is not only had you done a thousand reps on the pitch. I think potentially I’m not going to say most importantly because you cannot overstate the value of that repetition of refining the pitch. But in that moment, because you didn’t know you were pitching, you also weren’t loaded with a sales attitude, sales mentality. And the best salespeople in the world are not interpreted as salespeople as trying to get the close. They are consultative salespeople or like there’s a sales model called the challenger model. And it’s this idea of kind of the takeaway, right? If you’re not really asking for the close and you’re just kind of putting stuff out there, people lean into it as the CEO did. And then the third is this idea of, for me, the value of relationships. And so, had you not had a social interaction with him, had you cold-called him, you likely would have gotten a different outcome.

Colin O’Brady: Totally.

Brad Weimert: So, the question for me on this is, today, how do you prioritize relationships and how do you think about them in the scheme of adventure and professional life?

Colin O’Brady: I mean, to me, it is the number one thing. I think that that’s a really– I love that that’s a take home from this because I know you and I, for sure, both share this in our, where we first met on 29029, which is a community of like-minded people doing an experience who also happen to be entrepreneurs and business people, whatever, but like, let’s go have an experience together, build a relationship, and who knows what could come from that? I have really oriented my life more and more and more as I’ve continued to learn this lesson in twofold. One, you look at all the research on happiness, fulfillment from the academics to anecdotally, like it really comes back to community. I mean, all of the research comes back to. There’s no culture, no time in the world, no whatever when people have been like, oh, yeah, people are super happy being in deep isolation or loneliness. In fact, it’s the opposite. It’s like, that’s one of the highest comorbidities for early depression, death, things like that. It’s an epidemic.

And in a connected digital world, people are actually more disconnected than ever from community. So, forget business for one second, there’s just a very strong case to be made for invest in community, invest in those that you love. And you’re going to have a more deeper and more fulfilled life. But overlay that on business, it’s massive. I mean, it is 100% massive for me. One thing that has been interesting in the way that I have built my career over time, and certainly, the story that I just shared sort of early in this phase of my career seven, eight, nine years ago was a great lesson in that, but I have doubled, tripled, quadrupled down on this, which is, I seek out opportunities that are win-win, one. I love having dope incredible experiences around the world with amazing people. I just like that because it’s fun. I know you did that Fiji trip a couple of years ago and if you’re still doing that, or different experiences you have, like, I just like doing that. So, that’s an easy yes, for me.

But it’s also not lost on me. To your point, like in the past year, I went on a trip to Egypt for 10 days with a crew of 150 business people, entrepreneurs, super high-level folks, billionaires, whatever, artists, creatives, highly curated group of people. And I’ve been on a few trips like that in the last couple of years wandering Antarctica, went to Egypt, this past year to Tanzania. And each one of those trips, I did not walk into that trip going like, “Oh, look up the list of all the people.” I mean, if I started listing the names, it’s like the who’s who, very, very impressive list of people. And you can look at that list and you go like, “Oh, I’m going to make sure that on the third day that I’m going to sit down next to that guy,” and like you said, do the pitch of the thing that I want to raise the money for the thing, am like, that could work, maybe you have this opportunity to be in this room. But to your point, I don’t know that that’s the best way to go about it.

And what’s actually, it’s just more naturally occurring is to be like, man, I’m here. We’re having a life experience. We’re on hot air balloons over the pyramid with some of the most interesting people. I’m going to show up as my authentic self, have fun, create real relationships, have meaningful connections with human beings. Sure, they have impressive resumes and my resume’s maybe impressive, whatever. But like, let’s just hang out human to human. And then a year from now, two years from now, five years, whatever that is, there becomes an opportunity because now you’re collaborating with your friends who happen to also be very successful or able to help you or vice versa, people that I can help with what they’re building or creating. And it feels like a just genuine collaboration with the people you love.

And it’s extremely hard to get at that level of trust or depth. And so, I’m making a few different points here. But sometimes, I think the entrepreneur sitting in the proverbial garage grinding on the computer, feels like I need to button share and work harder, harder, harder, harder, harder. And that’s true, you got to put the time in. I put reps in every single day of the “work.” But relationships are such a force multiplier to growth, that investing the money and more importantly, the time to be like, oh, wow, I got invited to this trip to Fiji or Egypt, or, I don’t know, somewhere nearby, doesn’t matter where the little kids have been extreme with extravagant location. People go, “Oh, but I’m going to get behind those emails. I’m not going to do the thing.” And I was like, “Yeah,” but you might meet somebody in that room that can 100x what you’re doing.

But if you go in there with that sales mentality on day one of like, “Oh, let me have this formal business meeting with you and sit across from you at a desk and try to talk about the thing, like, yes, we got to do those meetings sometimes. I have to.” But there’s other times you can create natural relationships with people. And I have found pretty much my entire career has been mostly built on those actual real relationships. And guess what? It’s way more fun too because now you’re doing fun stuff with people that you actually know and care about, have been vulnerable with and have life experience with like, so it’s win, win, win, I think.

Brad Weimert: Yeah. Where my head went with that was a lot of people think that the path to success through relationships is connecting with the right people. And another frame for that is that you don’t build deep relationships with dope people by just meeting dope people. You build deep relationships with dope people by being a dope person so that when you meet dope people, you might have something in common. You might connect, right? If you go and meet a world-class anything and you have not established yourself as an introspective, thoughtful person that’s put in time, you meet that person and you are a fanboy. If you have put in a lot of time in something in your life, it doesn’t matter what it is something and you have shown that you are learning, growing confident, that world-class person sees that. And you have some overlap, something to talk about.

Colin O’Brady: And I love what you said, it can be in something. So, I had this funny– so actually, this is the opening story of my book, The 12-Hour Walk, and it speaks directly to this. And it’s a funny moment in my life, because I make the mistake, and I get pulled into this mistake of what you said. So, I get invited. I’m speaking. I do a lot of public speaking. And I’m speaking for this big Wall Street conference. This was many years ago, kind of not early, early days of speaking, but on the beginning of that. I’ve been doing it a lot now, many years.

Brad Weimert: Before or after the Grand Slam?

Colin O’Brady: It’s after the Grand Slam, but before Antartica.

Brad Weimert: Got it.

Colin O’Brady: Yeah. I can’t remember the exact date. But yeah, anyways, so it’s several years ago.

Brad Weimert: But we had mentioned that Antarctica becomes this pivot point. So, I want to jump there in a minute. But Antarctica becomes this pivot point of fame on some level because there was so much publicity. So, Grand Slam, you’re speaking, which means you don’t have a ton of attention yet.

Colin O’Brady: Yeah, yeah. So, I get invited, and I get invited to this– I’m speaking for this big Wall Street event, the who’s who of Wall Street, billionaire hedge fund guys. It’s not just one bank. It’s like, many different hedge funds and the biggest banks are all represented there. And then they invite me the night before to say, like, “Hey, because you’re one of the keynote speakers at this event, we want to invite you to this little cocktail, intimate dinner.” And I don’t really know that much about it other than it’s supposed to kind of be like the who’s who of like, whatever.

And so, I walk in and I’m in my typical black T-shirt, jeans, Jordans. And I’ve looked at the address, I’m in Manhattan, and I go up, and I walk in and I’m in this ridiculously nice apartment building, right? And I walk up to the doorman, I’m like, “Hey, I’m supposed to have this thing at the penthouse. I’m running a little bit behind.” And that dude looks at me straight up and he goes, like, “Oh, if you’re with catering, you need to use the service elevator.” And I’m like, “Oh, actually, I think I’m a guest,” whatever.

Brad Weimert: I’m the keynote speaker, b*tch.

Colin O’Brady: And the guy’s kind of like, just put off by me, whatever. But eventually, he’s like, “Oh, I guess you are. Okay, go up.” And he puts me in the elevator. And it’s one of those Manhattan buildings where the penthouse doesn’t go to the hallway, goes directly into the apartment, right? So, you go up and you’re in the penthouse, just like opens up and just like ridiculous.

Brad Weimert: And you didn’t know what was happening probably. It just opens and you’re like, “Oh, sh*t, I’m in here.”

Colin O’Brady: Yeah, I’m like, “Oh, here we go. Here we go.” So, I walk in and every single person in this room is tailored suit, $100,000 watch, Rolex, Patek, the whole deal, just looking sharp and crisp. And here I am, like Jordan sneakers, T-shirt, and I’m like, “Oh, man, I may have–” maybe I should have thought about this, whatever but I walk in with my confident-ish vision of self and start talking to people whenever and then they invite us to dinner. And actually, most of the people actually leave. There’s a cocktail hour with 50 people or something like that. And they pull us into a room and it’s like eight people for this dinner. So, it’s like, say goodbye to the dregs. They have been down, like sitting, and I’m sitting at the head of this table.

Brad Weimert: Oh my god.

Colin O’Brady: Just like place cards and everything. And the host, this guy whose apartment it was, starts going like, “Hey, I’d like every–” we pretty much all know each other because we’re competitors, running, and they’re all like good old boys’ club. The average age in terms is like 70 years old, all white dudes, all classic, a lot of Wall Street kind of movie or something like that. And they all start introducing themselves. And it’s just one after the next. I’m not going to say the names, but it is literally like the who’s who, this billion-dollar hedge fund, that billion-dollar hedge fund, this sovereign wealth fund, I mean, just the who’s who of Wall Street and then comes around to me last.

And I’m thinking to myself, this is why I brought this story because I’m thinking to myself like, “Man, what am I going to say in this room?” They’re all like, “Oh, my take on macroeconomic policy is this and that, and bla, bla, bla, and this money, $100 trillion of this GDP is going to move from here to there.” A lot of them make these big claims. And now, it’s me. They’re looking at me, dude in a T-shirt. No, to your point, like, not as established with my notoriety at this point in my career, and I’m like, “Yes. So, I’m Colin, and well, I have an economics degree from Yale. I actually worked on Wall Street as a commodities trader for 10 months.” Like, I’m trying to speak their language back to them, which is laughable because it’s like, these guys are the most f*cking incredible in this and they don’t need to hear about some kid who randomly f*cking traded commodities, like, whatever.

And thank God, the host steps in, and he’s like, “No, no, no, no, Colin. Tell them about the thing.” And I’m like, “What?” And he literally goes, “Do you guys know who you’re sitting with right now? This is Colin O’Brady.” He starts being like, “He just climbed Everest. He’s just in the Explorers Grand Slam.” He said, “This world and that world record.” And he’s like going through this. And all of the sudden, and I’m like, “Yeah, that’s all true. Great.” And I’m assuming, now I’m thinking like, now, we’re going back to the regularly scheduled…

Brad Weimert: Now, let’s talk about economics.

Colin O’Brady: Economic policy or whatever. And these guys all stop and look at me and are like, “Oh, God, we’re sick of f*cking talking about movie. Let’s talk about this, let’s talk about adventure, let’s whatever.” And we end up having this very engaging conversation. And I end up being sort of the core focus of the entire– they want to know everything about Everest. Oh, you’ve seen dead bodies up there? Have you this? Have you that, whatever?

And the closing of this story in the book, The 12-Hour Walk, is I had gotten this point asking people this question. So, what’s your Everest? Because the story for me was like, I was a kid and I was dreaming about climbing Everest. And so, I had this dream inside of me. And I ask school kids this question all the time. But in this room of people, they’re so engaged with it, I just like said to them, I was like, “So, what’s like? I would love to know, is this what you guys always dream? What were you at? What were you like when you were 10, 15 years old growing up?” And they’re super charismatic, really, obviously impressive group of people. It just goes crickets in the room. It just goes silent and, like, kind of people are sort of looking around and no one answers. And it’s an awkward pause until somebody says, cracks some joke, and takes the conversation in different direction. But no one answers the question. And I was like, “Oh, that was weird.” Did I say the wrong thing, whatever?

So, I’m walking out of the room that night after dessert and all this sort of stuff. And I’m getting back in this elevator to go down from the penthouse and go back to my hotel room, whatever. And this guy pulls me aside. He’s probably, I guess, at the average age is probably like 70 years old. This guy’s probably look like his age. He’s an older guy in the room, pulls me aside. And he just says, “Hey, I just wanted to apologize for my friends earlier tonight.” And I was like, “Oh, there’s nothing to apologize about it.” And he goes, “No, no, no, you asked a very important question. And none of us had a good answer to it.”

And he looks at me and he says, “I have made more money than you can possibly ever imagine.” And he goes, “But there’s this summer camp that I went to when I was 14 in Upstate New York. And I have this moment in my mind of being on this rowboat, and the stillness and the calm of that, and being in nature. And there’s not a day that goes by that I don’t go back in my life and wonder, did I miss it? Did I spend too much time in these boardrooms, thinking about finance or whatever?” And he just throws that as sort of like this open-ended question as an old man reflecting on his life. And then he kissed me. He goes, “Promise me this, keep doing what you’re doing. Keep asking yourself that question, what’s your next Everest? What are you actually passionate about? What lights you up?” There’s no right answer other than actually listening to that. And he’s like, “And now I see, I wish I had asked myself that question a few more times throughout my own life.”

And in the moment, I mean, I almost thought he was tearing up and it was an emotional conversation that he was sharing this with me and it stuck with me, hence why I opened my book with that story because here I am sitting in a room of people who are quite literally the pinnacle of what most would consider the highest level of success, certainly financially. And still, as this guy is reflecting on his life, he’s going like, “Huh, where did I go wrong? What could have been different? Where could I have been more deeply fulfilled?”

And it wasn’t a lesson about money is the root of all evil, wasn’t that. It was just like, what do you really care about? How can you monetize that or make that fun? But I think entrepreneurship is born from that, to bring this all the way back to this conversation is the best entrepreneurs that I know, I know a lot of wildly successful entrepreneurs, weren’t only thinking about their exit one day. They were actually like, “Yeah, I’m going to get rich doing this thing. And that’s fun. And I can have this big exit.” But it’s because I authentically actually want to climb this Everest day in and day out. Even when it’s hard, I’m going to get up like, this is interesting. This is creative. I’m solving this problem. I met this person. I’m flying here, I’m going there. Like, the process of doing, it wasn’t a mortgaging the present for the future kind of scenario. And that’s what I took from that conversation with that guy.

But to your point, there is all started is, when you meet a bunch of interesting people, it’s about network and you’re talking about networking or just getting to know other people. It’s not actually saying, “Can I be a mirror of you?” In fact, by doing that, you end up in a competitive space with that person, you have actually less likely to connect with them some of the time, because now you guys are too close in comparison. But it’s the inflection of I’m sitting in a room of hedge fund, high-net-worth guys who have been wildly successful.

And I’m interested because I’m not necessary interested in the crazy opulence. But I’m like, wow, like something inside of you got you to this place which means you are driven in this. And they’re looking at me going, “That’s hilarious that you said you have an economics degree from Yale, but she doesn’t know anything about our world, but you know about the world, Colin, that we don’t have any experience in.” But what’s the essence, passion, drive, grit, perseverance, risks, assessing risks, pushing through when it’s hard or whatever? And there’s that commonality.

And so, to your point, when you meet other really dynamic, interesting people, it’s not, let me be a mirror of your exact same dynamism. It’s like, “Oh, I see that thing in you, but I can also learn from you. I can create. We can create together, we can hang out, we can have discussions,” not about the intricacies of payments or whatever, you know the niche thing that you know super well, but about passion, creativity, entrepreneurship, scale, all the things I just said, I mean, and that is what I think is the juice.

Brad Weimert: Yeah. And I think that there is frequently an area in the Venn diagram where you overlap. And you just highlighted what some of those things are. What I think people fail to recognize is, this is true for many, many, many people, but specifically for the elite, for the high performers in any space. They are far less interested in what they already know. What engages those people, excites those people, intrigues those people are the areas that they don’t know how to perform well in.

Colin O’Brady: Totally.

Brad Weimert: That’s what impresses them, right? To the elite, it’s the things that they can’t do well or haven’t done well, not can’t but haven’t done well. That’s what’s interesting. Oh, sh*t, not only do you do this thing, but you do it at that level. What the f*ck, right? And so, I think that for people that are spending time on whatever they’re spending time on, that’s the ticket. And some people look at that as authenticity, being true to yourself. To me, I think one of the most difficult things in life to find is this perpetual North Star to guide you. And if you are one of the few that has found it, you’re lucky, right? Applause to you. But in the meantime, f*cking work until you find it because through that work, you learn, you grow, you become more dynamic, you become a better person. And that allows you to continue to level up and meet other people that can help you through that journey.

Colin O’Brady: Totally. And I think, I mean, that’s incredibly well said and that question, I do ask that question, people, what’s your Everest? And some people have great answers to your point, “Oh, I’m lit up about this. I always dreamed about this. I’m passionate about this.” And maybe they said, but I haven’t gotten there because there’s some limiting belief of why they haven’t gone towards it, but they actually know what it is. But there is a lot of people to your point that go, that’s the way they ask the question back to me when I ask a question is, “What if I don’t know what my Everest is?” Which is to say like, “I want that purpose drive, but I’m sitting here in stillness of like, waiting it to hit me over the head.”

And it is by taking intentional. The answer, I believe, is not like, “I don’t know. Sit there for a while, you might figure it out.” It’s like, “Try stuff. Mix it up. Take that job, take that risk, try something different.” It might be the wrong thing. But guess what? When you start to think like, I don’t like that is actually a powerful way to get closer towards what you do like or what you are passionate about, right? We don’t know love without heartbreak. We don’t know pleasure without pain, which means like, you’re not going to know what your Everest is or what your North Star is without also knowing what your North Star isn’t. And so, it is by doing that we unlock and discover some of that.

Brad Weimert: I totally agree. And I’m going to pull this back to endurance because we would be remiss to not talk about a couple of these f*cking ridiculous, more recent things that you’ve done. Frequently, you don’t know what you don’t like until you give it enough time to figure it out. And so, in endurance, I’ve done a little bit of endurance stuff, baby stuff next to Colin O’Brady.

Colin O’Brady: I met this guy. I have an event called 29029, where you climb the vertical feet of Mount Everest from sea level. And it is a crazy hard challenge for 99.9% of the people. But Brad shows up on day one, he goes, “Everest, I mean, that seems pretty cool.” But do you think in the same 36 hours that you guys are going to climb Mount Everest, the equivalent of Mount Everest, 29,000 vertical feet? In case, you’re wondering, that is a ton of vertical feet, like 50% of the people don’t finish even after 36 hours nonstop.

Brad looks at us and goes, “I’m going to do it twice. I’m going for double Everest but in the same amount of time.” And we all looked at him like, “Yeah, cool.” Guy with the Mohawk wants to do some crazy thing. Respect. And he has raised a bunch of money for charity too, which was awesome. However, he, sure enough, 36 hours nonstop, I think right down to the minute practically, managed to climb 34 laps of Stratton, Vermont, which is insane. And that was our first inaugural event back in 2017. We’ve hosted dozens and dozens of them. The business is thriving. We have seven events per year.

And still, to this day, nobody has come even remotely close to trying to double up. In fact, someone did try it last year at Utah. It’s 11 laps at Utah. And after like the 12th or 13th, they were like, “Bro, this is insane. Stop. Take my red hat and go home.” So, when Brad says he does the little dirty things, he’s being modest.

Brad Weimert: I appreciate that. That was an experience. And I love that you guys put it on and do it. And there are tons of stories in that, lessons in that for me. And one of them is in any endurance event, there’s, I refer to it as the inevitable suck. It’s not a question of– maybe a fraction of 1% of the time you do an endurance event and somehow you fly through it and it doesn’t suck.

Colin O’Brady: Pretty rare.

Brad Weimert: Pretty f*cking rare. Yeah, you’re right. Pretty f*cking rare if ever. And it’s usually some long training run that just so happens, nothing went wrong, right? But usually, you have to live in that space of sh*ttiness for at least a little bit and usually a long time. And I think there are a lot of things you can get out of this, but to frame Antarctica, your journey across Antarctica, a marathon for normal humans is usually somewhere between three and five hours. Ironman races get cut off at 16 hours. Antarctica, you are going for– how many hours a day roughly?

Colin O’Brady: Twelve hours a day.

Brad Weimert: Twelve hours a day for 54 days straight. And I went for, and it’s what? 932 miles. And I want to highlight the intensity of that for people because the first question and I imagine you get this too, for people that do endurance stuff is they say, “Have you done an Ironman?” And I’m like, “Motherf*cker. And no, I haven’t.” And I’m like, “Sh*t, I should do one just so I can answer that question,” right?

But an Ironman is not anywhere near the pinnacle of endurance athletics, right? It is the one that, I think, and by the way, it’s still a f*cking significant thing, specifically, if you race it, as opposed to just aim to complete it. But it’s a lot of time, 12 hours straight to be pushing and then to do it repeatedly day after day after day. I look at endurance stuff. When people say, “How do you do those things?” I look at it and say there are three things. There’s the physical training component, and people think that that’s the hard part. There’s the mental side of it, and then there’s the nutrition side of it. If you agree with those three things any way, which of those is the hardest thing for you?

Colin O’Brady: So, the mental component, the physical component, or the nutrition component?

Brad Weimert: Yeah.

Colin O’Brady: I mean, they’re all definitely interconnected, for sure. I think, without a doubt, the most important of those three is the mental component. I mean, really, to me, there’s no even close comparison to the other two. I feel like when I look at that sort of pyramid of those three things as it relates to endurance, the physical and the nutrition component are table stakes, which means you can’t run a marathon or walk across Antarctica if you don’t have sufficient calories to fill your body. Like, our bodies can hold 90 minutes of glycogen, essentially, sugar. You can be a Kenyan marathoner running 4:50 marathon pace and get to 90 minutes, you haven’t eaten anything, like literally, your body is going to essentially shut down, you’re going to be running like 10-minute mile pace. That’s just physiology of the body. So, nutrition, super important as a baseline to get, right? And I have spent a lot of time refining that to get as perfect as possible and optimize.

Physical component, similarly, like you can’t pull as I did a 375-pound sled alone across Antarctica for 54 days if you’ve never been to the gym ever. It’s just, you have to have some level of work that you’ve put in to get to all of that. But the other two matter zero, doesn’t matter how peak of condition you are in or how well your nutrition is if you don’t have the mindset to get there. And I will share it in the opposite direction, which is I’ve seen people overcome their physical limitations with the mindset.

We’ll talk about Antarctica specifically because we were just talking about 29029 comes to mind real quick, which is our business 29029 ever seeing fun business, we love it. It’s all about community, inviting people to do this incredible challenge. You’ve been there a couple of times. We love having you out there. What’s amazing is that we have had Olympians and Ironmen and world-class athletes do our event. And it’s not a race, but no one’s really been able to finish it faster than about 15 or so hours, which is still the maximum time as an Ironman, and that’s the fastest people who have ever done it essentially, right? But 36 hours are cutoff.

And what’s more interesting to me is that we have had numerous people show up having never done a 5k, having never done an endurance event, not owning the identity of I’m an endurance athlete and I’ve already done this ultra and that ultra and this Ironman, that Ironman. They were like, “I heard about this. It sounded interesting.” Because it’s hiking uphill, you don’t need a skill acquisition, like, you don’t need to have a bike, you don’t need equipment, you don’t need to know how to do a skill. Most people can walk uphill, at least for some period of time.

So, we have had people show up. And at first, we were like, “Oh my God.” This people, maybe they should do something else first. I have seen those people time and time and again, middle-aged woman in their 50s, never done a 5k, finished 29029 Everest thing. And why? To your question is they showed up. Yes, it isn’t training ahead of time, but they showed up with the mentality of, I’m willing to try this. And I think if I stay out here for 36 hours nonstop and I don’t sleep and I keep moving, I might actually be able to finish this. And that, 100%, I’ve watched it over again, is the power of the human spirit and what we have inside of ourselves when we set our mind to something and have that focus mindset on a problem. And that for me, has certainly made all the difference in Antarctica and other realms of my life for sure.

Brad Weimert: F*ck, yeah, I love that. I get– this is the problem with having conversations with you is then I want to go do sh*t. And the reason that I got to 29029 in the first place because I was listening to Jesse Itzler speak on stage and I was drinking tequila in the back of the room. And I had a visceral response to him talking about this idea, which at that point, you guys had never done before 29029 event. And I was like, “F,” I think I literally said that, “F*ck” and people looked at me and I just knew, I had to go to this thing. And so, I hear you talking about it and I’m like, “Oh, sh*t, I want to go do something.” But it begs the question.

It is easy to give up in general. It is easier to give up when something significant happens that indicates that you should give up – a physical injury, nutrition deficiency, like you bonk, you hit a wall, not literally but physiologically. In those moments, when you realize this is highly improbable right now or borderline stupid to keep going, in the moment, how do you make sure that you as an athlete, as a competitor, as Colin, keep going?

Colin O’Brady: Yeah, I know, we don’t have a ton more time left, but I will share. To me, it’s interesting. A couple of things come up when you asked me that question. One is, I think we have this belief inside of us that things are– we sort of have a bias towards something being linear, which means like, if it was good and then it’s getting bad in the middle of endurance event, it can only possibly get worse, right? That’s where our mind goes. It’s like, I started the marathon out and my feet weren’t sore. And then 10 miles in, my feet were pretty sore. And then 20 miles in, my knees were like screaming. So, at the finish line, I’m going to be able to like not be able to walk, right? And again, that’s a logical thought process. It turns out it doesn’t really work that way. And you know this from doing enough endurance events, which is like, it’s actually not linear, particularly if you can convince yourself in those hard moments to keep going.

So, from Antarctica, I’ll share a very brief, very concise version of this story. I get dropped off in Antarctica, it’s 2018. I’m attempting to be the world’s first person in the history to cross the entire continent of Antarctica, the landmass, solo, unsupported, which means no resupplies of food or fuel and unaided. So, no kites, no dogs, no nothing else that’s going to propel me. Just me, mano a mano, trying to cross the frozen continent alone.

And I’ve trained for it. I’m like, think I’m prepared. I just had this big break in the press, where the New York Times once featured it, like big, like front. I was the biggest piece of press that ever gotten to that point in my career. So, Colin O’Brady, he’s going to attempt to do this thing, like, whatever. And I get down there and I load up my sled, the plane drops me off, takes off. So, I’m alone in Antarctica. And I’m like, “Okay, here it is. I’m going to start beginning.” And I tried to pull my sled. And I straight up can’t pull it, like, I can move it 10 feet. I’m like, “Ahhh,” I’m like, pull 10 steps and stops. It’s 375 pounds. I know, it’s the heaviest it’s going to be at the beginning because I’m trying to have just enough food in there to survive to the other side. And so, each day, it’s going to get a little bit lighter, but I can’t move it on the first day. And I’ve already taken everything out of that sled that I can possibly think to take out of it.

And the reason people had failed time and time again, including someone who had died a few years earlier just 100 miles from the finish, is that the math equation didn’t work. If you took, to your point about nutrition, too little food, some point, 40, 50 days, your body shuts down and you can no longer move. And that’s a very compromised place to be in in Antarctica. But if you take too much, you’re me, at the start line, not being able to move my sled at all.

And I break down, I start crying in that moment. I actually called my wife back on the phone. And I’m like, I’m crying and the tears are freezing in my face. I’m like, “What do I do?” And she says to me, I can see thematically here, I’ve had some great wisdom from the strong women in my life. And she was like, “Forget about the nearly 1,000 miles you have to go. Forget about how far it is or if you can make it. Get through today, get through this moment.” And she knows that I have these waypoints marked on my GPS, like, “Get to the first waypoint. Just get to the first waypoint. There’s 1,000 more miles to go. But today, take an incremental step to getting there.”

And that really did reorient my mind. In that moment, I was like, “Fine, whatever.” I start doing the math of the 1,000. Like, I went a half a mile today. This is never going to like, never going to work. And I just read this article in New York Times, like how embarrassing. She’s like, “Forget about that.” And it’s the same for you. You’re talking about an endurance event, you’re bonking, you’re having a tough moment, or you’re in the middle of an entrepreneurial push and you’re just getting smacked in the face. A bunch of things have gone wrong. Those are the moments where it’s like, “Man, I should just throw my hands up and quit. I’m done here. I should just quit.”

But if you can find it in the middle of an endurance event, or for me alone in Antarctica to be like, “Okay, I did get to the first waypoint today. Can I get to the next one tomorrow? It’s only four miles from here.” Yes, 930 more to go. But can you go four more today? Four more becomes five, five more become six. And fast forward, on my 53rd day alone in Antarctica, when I’m nearly completely out of food, my body is beat up. I’ve got the beginnings of frostbite across my face. I mean, you’ve seen the pictures, like I’m a skeleton. I’m a shell of a human at this point, because I’ve been out there pulling my sled 12 hours every single day, I end up getting this deep surge of energy inside of my body, inside my mind, inside of my spirit. And I actually end up pulling my sled 33 hours nonstop, 77 miles in one continuous push to complete the crossing, become the world’s first person across Antarctica.

And I share that because, again, it’s not linear. Yes, my sled was lighter at the end, but my body was ravaged. I’ve been a bone in Antarctica for 50 some days. But on day one, I’m crying, tears frozen to my face, and I can barely move my sled wanting to quit and give up. But somehow, I found it myself not to give up. And on the day when it should seem, the day when I’m stumbling and can’t walk and can’t move, my body’s broken down, that’s what like logic would tell you, I actually perform at my absolute best. Because the process of going through the difficulty in the challenge and overcoming all the incremental setbacks along the way, actually forged an even stronger version of myself than actually existed in that preliminary part of that.

And so, for me, it’s always a reminder, I said it before, failure plus perseverance equals success. Another thing I’m fond of saying, and it goes back to that Mark Parker story of the Nike CEO, I say, “Winners lose the most.” Winners lose the most. It’s those reps, it’s those incremental failures, it’s those setbacks along the way that eventually do lead to that. But it only leads to that in that equation if you take the incremental failures or the moments and endurance when you’re feeling bad. And you add the ingredient of perseverance. A way of saying, “You know what? I’m going to go one step further. I’m going to make it to one more way point. I’m going to send one more email. I’m going to pick up the phone and call one more, try to close one more sale.” And you just chip, chip, chip, chip away of that. And then it doesn’t get worse, the knees don’t hurt more.

And we’ve seen people almost every marathon who couldn’t walk at mile 20, go to the end of the New York City Marathon, people even finishing five hours, six hours back to the Packers, they sprint across the finish line 9 times out of 10 because there is more inside of you. And it’s not a linear decreasing of your power. There is actually way, way, way more power that lives inside of us if we can keep moving forward.

Brad Weimert: I love that. Okay, so I want to highlight a couple of things because I know we’re coming up on time. But you wrote a book about that experience, The Impossible First. It is, I have a lot of friends that write books. And most of them are trash. Said a nicer way and less for effect. They’re either not well written or not super impactful. And they’re written for the purpose of being a business card or trying to amplify whatever they’re doing. The Impossible First is a really epic journey that we’ve touched on a couple points of that here. But it’s also written incredibly well. And if you listen to it, you read it, so you get to hear the stories from your perspective, which is in this case– in some cases, it’s irrelevant. In this case, really adds a ton to it. So, the audiobook is great. One of the things that I like to ask adventurers and it seems to be a contentious point for some is, is it more about the adventure and the experience of the adventure or the story?

Colin O’Brady: Yeah, it’s a great question. Not contentious at all. I think, it’s both. I think it really is both. And I think that having those things in balance at both, I think, create the most impact. For me, of course, first and foremost, it’s about the experience and I have one simple question that I ask myself before anyone on my expeditions, anyone on my big adventures, is my litmus test very clear? If I could tell nobody about this, would I still want to do it? And the second I answered no to that question, that’s off the books. I’m not doing that expedition, just not interested. So, that’s my first anchor point.

But if I answered the question yes, yes, I would walk across Antarctica for 54 days, but I could tell nobody about it, I can tell you that 100% because for me, I’m just a curious person. I had a deep curiosity, what will happen to my mind, my body, my spirit, success or failure? If I’m alone for that long, like we don’t spend time alone, let alone in a place that’s minus 40 degrees with the wind blowing where every decision you make is of the highest stakes, yeah, I’m down for that. However, beyond that, it’s about the question about the story is, one, yes, I certainly believe we are the stories that we tell ourselves. But the reason we’re having this conversation via podcasts, the reason I’ve been inspired by so many podcasts, I’m an avid reader by so many books, I mentioned a book, Jon Krakauer’s Into Thin Air that he wrote in 1996 that change the trajectory of my life.

We have the ability to ripple out into the world and impact and inspire one another. And so, for me, not from an ego, hey, read my book, don’t read anyone else’s book. That’s not the point. It’s to say, like, “Hey, I think that we all have a responsibility.” Whether you’re famous, not famous, rich, not poor, around a dinner table, in a stadium full of 10,000 people on a stage, when we share stories with one another, we have the ability to inspire, impact positively, have an effect on those around us. And I think that that is a really beautiful part of the human experience. And so, for me, certainly, the business fundamentals of that have been aligned in that. I get to do the things that I love to do. And by sharing those things, I’ve created a number of very lucrative business models for myself, great. But more than anything, it’s a win, win, win, which is we have the ability to inspire each other and have that ripple effect of positivity roll out into the world.

And then I think that bounces off, like there’s people have been like, “Oh, my God, you inspire me. And I did this.” And they tell me their story. And they’re now telling me story now, I’m super inspired to go do the next thing and then, it’s like, “Oh, we’re both giving each other plus, plus, plus, plus, plus energy and uplifting each other.” And I love that.

Brad Weimert: I do, too. And I think that I would like to challenge anybody from an entrepreneurial perspective to think about the things that you’ve done well and that you’re good at and think about how to package those and communicate them to people in your life because it will inspire them. It is likely. And it’s specifically the things that you are so good at or you do so often that you think they’re mundane. And so many people don’t know how to do it, can’t hold themselves accountable, don’t have the discipline or the experience or the reps. And so, hearing the story is enough to inspire.

The other thing that you hit on, and I’m going to say it a different way, is you talked about the ripple effect and going back and forth. Said another way, stories are phenomenal, stories of your experience are a phenomenal opportunity to connect and build relationships with people. And when I think about why, my driver for a lot of things, ultimately, it’s the depth of relationships. One last question for you and hopefully, we can carve out time another time because I’ve got a thousand others, but the one that inevitably, you have to get all the time is you’ve done– now you have 10 world records. You’ve done these death defying– we didn’t even get into your near-death experience as of late in your most recent expedition, death-defying experiences. Succinctly, why do you keep doing all this crazy sh*t?

Colin O’Brady: For me, it is like, I said the word, I think the word curiosity continues to bubble up inside of me. And that’s yes, we’ve talked a lot about the expeditions and those are some of the most rich stories, of course. But to me, it’s across all different spectrums, like the curiosity, not always just of high performance, but of trying new things that I’ve never done before. I appreciate your kind words about my book. And I’ve written two books now, but before I wrote the first book, The Impossible first, I was like, “I’ve never written a book before.” And I was like, “What’s the best, whatever, accolade of writing a book?” Okay, a New York Times bestseller. And I was like, “Great. I want to become a New York Times bestseller.”

Again, not because the ego of that, but it allows me to have like a focus on like, okay, then if you want to do that at that level, well, then, what was that required? Oh, I got to learn how to write super well, I need to learn how to craft story. I need to understand the publishing industry. I need to understand all stuff. That’s just my curiosity going, like, if that goal, which is somewhat of an arbitrary goal and I’m very pleased to say that I did reach that goal, which is like out of every million books written, it’s 10 books out of a million become New York Times bestseller, just a very small percentage, that’s not the point.

The point is, the why question, is the curiosity to continue to just peel back the onions on the human experience and having the goal, I want to walk across Antarctica. It’s not so I can beat my chest afterwards. It’s like actually in the process of doing. Throwing the goal out there, great. If I’m going to write a book, I want to write a New York Times bestseller. Well, okay, then that opens up a series of 10,000 other questions and people I get to interact with through the course of that, of just learning of curiosity.

And so, as I approach other things, yes, other expeditions, I recently became a father. My son is seven months old. That’s a ton. Adventure, a lifelong adventure in itself, publishing, stuff I do in Hollywood, other businesses, whatever, those are all formed from the place of a curiosity of sucking the juice out of life, of really asking yourself, like, what can we experience on this one precious ride and through life? And these goals, so to speak, that they look very like, oh, these very specific linear goals are actually just carrots for me to throw in front of myself to be able to continue to explore. I love to say the top of one mountain is really just the bottom of the next. And I don’t say that in the hamster wheel of achievement of like, okay, the next thing and the next accolade, this. But actually, of deriving purpose through life in a little bit of direction, loose direction to give yourself a life of context or give yourself a context to sort of pursue things in life. And for me, my most meaningful experiences come from having sort of created that context throughout my life.

Brad Weimert: The impossible First, a must-read. 12-Hour Walk is the most recent one, and probably more accessible to a lot of humanity. Colin O’Brady, where else do you want to point people if they want to find out more about you or whatever you’re interested in, right?

Colin O’Brady: Yeah. Come say hi on Instagram or social media @colinobrady. Of course, my website is my name, Colin O’Brady, speaking any of that kind of stuff. But we didn’t get to talk about it a lot, but definitely check out The 12-Hour Walk. Yes, it’s a book. It’s live and full of adventure. It’s a fast and fun read, but it really is prescriptive in the sense that it’s talking about how we can all overcome these limiting beliefs and really strengthen our mindset through a very, very single, succinct one call-to-action, which is an invitation for people to turn their phone off for a day, walk out their front door, and take a 12-hour walk alone, can be in your neighborhood, can be in a trail somewhere. It doesn’t matter.

And it also doesn’t matter how many breaks you take. This is not a race. This isn’t how far you can go in 12 hours. But it is actually a pattern reset because ask yourself, when is the last time that I actually spent 12 hours alone by yourself? And you might be an entrepreneur thinking, I don’t have the time for that. Well, there’s a chapter in the book that’s about that limiting belief. But I will say this, you don’t not have the time for that. I will tell you right now, tens of thousands, if not more than that, have done that, the walk all around the world, people do it every single day. There’s an app that supports it, tracks the app, etc. We’ve had people in 40, 50 countries every continent do the 12-hour walk.

But here’s the thing, taking a day alone in your thoughts, the amount of people come back from the walk, this semi video, they’re crying, they’re cracked open. They have 50 pages in their journals written because of the creativity that unlocks. And even though your task list seems endless right now, I got to do this, I got to send the team, I got to be here, I got to be in this meeting, I got to do whatever, yes, you need to do all those things to do what you’re pursuing right now, but there is so much value in this simple prescription which is free at your front door is stop. Stop for a second. Look inwards. Listen to your internal dialog of what’s going on.

So, The 12-Hour Walk book is about that, but it’s essence. It’s an invitation. I have to read the book. Turn your phone off. Turn your podcast off. Sorry, Brad, not this one walk. It takes 12 hours to walk alone in silence. And there is so much to be gained. I’ve seen it happen at massive scale all across the world for people taking that moment to look inward. You can learn more at the 12HourWalk.com.

Brad Weimert: I love it. Sometimes, at my busiest, I am challenged to remember that the most productive thing I can do is nothing. Colin O’Brady, I appreciate you coming out, man. It’s always good to see you.

Colin O’Brady: Always a pleasure, my friend. Thanks for having me.