The Geography of Risk

Steve: Here is the moment every climber knows. You’ve reached the summit and the ropes are being put away, getting ready for the descent, and your partner offers a handshake, but it’s refused. Wait until we get down. That’s exactly what Rob Slater told Kyle Lefkoff at the top of the Sandstone Tower in Colorado many years ago. It was a small moment, but one that became a lifelong principle. Kyle calls it Slater’s Law. The climb is not over until the ropes are on the ground. Kyle Lefkoff has spent 40 years living by that rule, not only in the mountains, but in one of the most unforgiving arenas of modern business capital. Kyle was a member of the 1986 American Expedition to K 2 during one of the deadliest seasons in mountaineering history. He later co-founded Array biopharma and remained chairman for 20 years. Long enough to see it acquired by Pfizer for nearly $12 billion. He helped create the American Institute for Avalanche Research and Education, creating the gold standard for avalanche education in the United States. what sets Kyle apart is not just what he has built. It is how he has built what he builds and who he builds with. He likes to say that he works slowly and deliberately and in one place. He chose Boulder, Colorado, not for the wealth or status or obviously the beaches, but because it was the only place where both of his callings could exist side by side, the climber and the investor. He built a consistent pipeline of business by building bridges to what he calls elite human capital. This episode is not about summit counts or portfolio returns. It’s about geography. It’s about risk. It is about the patience required to build something that lasts and about the wisdom it takes to hold off on the celebrations until everyone is safely down. The outcome is not the destination to strive for. Bringing everyone. Home is the destination to strive for building bridges for others to cross. It’s the destination to strive for democratizing talent, information medicine, education. climber and venture capitalist, Kyle, FK, these are the destinations to strive for. My name is Steve House this is Voice of the Mountains.

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Steve: Kyle, welcome to Voice of the Mountains.

Kyle: you, Steve. Thanks for having me.

Steve: I wanna start with something that you wrote, you said some days that’s the summit on others. It’s failure and a long walk home and every effort, luck and timing play a major role. Most people in either of your worlds, whether it be venture capital or albinism, often try to obfuscate or maybe even hide from that reality.

They talk about their skills, all the preparation they’ve done what great masters they are of their space, but you put luck and unforeseeable conclusion at the center. Why do you do that?

Kyle: It’s unavoidable in both of those spheres, both in climbing and in uh, and in venture capital. You cannot discount the, the luck of the draw. Also the timing. It’s so much easier to succeed when the winds behind you and the skies are clear than it is in stormy conditions.

Steve: Can you give me like an example of, uh, of that in either, either in climbing or skiing or, or in business?

Kyle: Um, you know, my favorite analogy are powder days. Because, because they don’t happen very often, when they’re, when they do, can see ’em coming. If you’re an experienced guide you can be in position if you know your terrain to, to serve up the best day of someone’s life for, for, for a powder day, the same thing happens in business.

As an experienced venture capitalist, you can see the momentum build in markets that you’re very familiar with. Um, you can see the stars begin to align. no certainty, but you at least have the opportunity to have the wind at your back, and that’s when you charge and, and to succeed with your entrepreneur in favorable conditions. Is, is one of the great joys in the venture capital business.

Steve: So let’s talk about your sort of origin story for a minute. Take me back to growing up what you described as being an intense kid, quote unquote, uh, in Atlanta, Georgia. And at some point you discovered that mountains and climbing were the place where which, which fit you, where you fit. Tell me about that.

Take me back to Georgia all those years ago.

Kyle: I, I believe that, that there exists a, a mutant gene in rock climbing that we’re all born with, and that appears early in your life as rock climber. You don’t know it till you experience it, but once you’ve experienced it, lost, you’ve been lost to rock climbing. often the case here in Boulder that parents of of children who are friends of mine will ask me to, guide their 11-year-old daughter and. You know, will you take, she, she loves the gym. She loves, she climbs on everything she’s obsessed with, with going to, to, to the rock gym. And like you, Kyle, to take her outside and climb on real rock. Would you do that? And my response is, I’ll be happy to do that and I’ll be happy to guide her. Um, are you prepared to accept the consequences if she has the mutant gene? Because then you’ve lost your child to rock climbing for the rest of their lives. There won’t be anything

Steve: There’s no, yeah. The, the gene is switched on and there’s no switching it off. They’ve, it’s, it’s activated.

Kyle: It’s not a phase they’re going through.

Steve: Hmm.

Kyle: to report. It’s the rest of their life. You possess it too, so you know exactly what I’m talking about.

Steve: A hundred percent.

Kyle: child growing up in Atlanta, I knew early on I was really in the wrong place. know why it was a, was disconnected from, from my peers and my surroundings as a child.

Steve: Hmm.

Kyle: and, uh, I was pretty precocious and I, I read extensively, um, from my earliest ages, but I didn’t know I was a rock climber until I went to summer camp at age 11 and was introduced to the sport by, uh, an Outward bound instructor there as part of the camp program. back from that summer, turned 12 years old, immediately began climbing on every rock in Atlanta. Um, found a group of young peers at age 12 and 13 and 14, most of whom I, I got to meet because I was a gymnast and our gymnastics team was filled with climbers, and those are a natural, a natural, um, connection.

Steve: Yeah. Yeah, sure.

Kyle: And then, and then when I was 15, I, I didn’t have a car and getting to a lot of the crags in North Georgia and North Carolina required a vehicle in those days.

Steve: Yeah.

Kyle: I was fortunate to meet Rich Gottlieb, one of the great rock climbers of his generation, who was 21 at the time and had a truck and a rack. And he wasn’t afraid to use either of. And I went on a campaign with him uh, to dis on a journey of discovery of the crags of Georgia and North Carolina.

These were unexplored, unknown places in the, in those days, every climb we did was the first ascent. Every, every, every thing we did ventured into the unknown, and it was, in retrospect, one of the most exciting times of my young life. So that’s what really hooked me on the whole thing. Um, I also, uh, I also read extensively in the, as you have in the literature of mountaineering in, in those days, this is the, the early 1970s. Um, you know, I, I took my Bar Mitzvah money and rack and a copy of Royal Robbins, advanced Rock Cle and devoted myself to, to trying to, to become a rock climber in what, in what was in those days, a, a really, nichey dangerous sport.

Steve: Mm. Absolutely. So what year are we talking? 1970.

Kyle: Yeah. 1973 to 75.

Steve: Okay. so what was the state of the art in rock climbing in 1973 to five?

Kyle: Uh, you still had a hammer on your, on your will and sit harness. Your,

Steve: Okay.

Kyle: your ebs and your, and your, uh, your, uh, your brand new pearl on rope. Kind of a new, new idea.

Steve: Right.

Kyle: Uh, were proudly displayed on your, on your rack. Uh, you didn’t wear a helmet

Steve: Yep.

Kyle: and, uh, you had a rack of stoppers. And any place that you couldn’t place a stopper, you placed a pin,

Steve: Aton.

Kyle: a peon.

Steve: So, and ebs, as, as some people may know, they’re, that was like the very first shoe specifically designed for rock climbing. And it was a pretty big departure from the mountaineering boots that people climbed in prior to that, which had like the classic lug soles with the lifted heel and the deep lugs in, in the tread, and they were completely smooth on the bottom and they had these big rans that went up the side.

They’re, in hindsight, they’re, they’re very like boxy. They look like a, a Volkswagen bus from the similar era, right? They’re like very kind of square and tall. But it was a, a huge revolution to have footwear specific to rock climbing. And of course it’s evolved immensely to what it is today, but the basic concept hasn’t actually really changed if you think about it in what’s at almost 50 years now.

So pretty amazing.

Kyle: It really was, they were exceptionally, uh, uncomfortable as well.

Steve: Yeah. Yeah. I, uh, did ha I never owned a pair, but I borrowed a pair for a while. Uh, when I was traveling around, when I was in my, when I was 18, 19, and I was in Slovenia, uh, I borrowed a pair of, uh, rock shoes from a guy and they happened to be ebs. So I had a little experience. They were probably from 1972 ’cause they’d, they’d been worn a lot, uh, by the time I got my hands on them.

That’s classic. So, uh, and I think you’re maybe even representing some of the, some of the fashion of the era for rock climbers.

Kyle: My heroes were, were Royal Robbins and,

Steve: Sure.

Kyle: Henry Barber, both of whom, both of whom were in their phase at that point, Royal, kind of at the end of his career. But Henry absolutely in the thick of it

Steve: Absolutely.

Kyle: climbers in the world. and both were mountain guides. Both, both were, you know, meaningful rock guides in their careers. So, um, the way they dressed, the way they acted, the, the, the. The, the seriousness with which they took their responsibilities and their sport were really influential on me, and I, I tried to emulate those at every opportunity.

Steve: And I would like to call out the, the beautiful toe colored cap you’re wearing and how that is like a, a dead, we talked about this before we started recording, but that is just a dead on ringer for Henry’s classic cap. And I know it because I’ve seen so many pictures of him all his famous roots that, that, you know, hot Henry, as he was known at the time, was, was doing these first ascents of all these. still difficult actually. Rock climbs all across, primarily the northeast, but as well as out west. Um, where he, where he traveled often. So, you know, you’re looking, you’re holding up the, you’re holding the torch here today, Kyle, I wanna, I want to commend you for that. You’re looking good. So, you know, you talked about, uh, stone Mountain, like in your book, and I, I wanna call out, I, because since I’m gonna mention the book again, that have a new book and it’s called High Exposure.

I have a copy of it sitting here, uh, in the booth and Beautiful. Everybody should, uh, check it out, but we’re not necessarily here to promote your book. But it’s, it’s been a lot of. A lot of the thinking and thoughts that went into the book when I received a copy. It was just all these same thoughts, like a lot of the conversations we’ve having and it felt a lot of, it felt very voice of the mountains to me. And you did talk to guys like Henry Barber, who’s, who’s still alive and kicking and, and uh, telling his stories and so on. So that’s, uh, but I want to take me back to Stone Mountain. Also. The Stone Mountain has a bit of a historical cultural significance. You wanna tell us about that a little bit.

Kyle: Stone Mountain is a, is a large granite Monadnock and just outside Atlanta, 20 minutes from downtown. It’s got a 800 foot north face

Steve: Huge.

Kyle: One of the biggest in the Southeast. And there’s a lot of big, granite domes in the southeast it’s easily accessible from Atlanta was 20 minutes by car from my home. uh, you know, in, in the early seventies it, it, it had only been climbed a couple of times and only by us some pretty torturous aid climbing. Um, but there’s quite a lot of free climbing down at the base of the North face of Stone Mountain. There’s some cracks and chimneys and corners that, free climbable for a pitch or two. But, know, it could have been one of the greatest granite crags in America. So close to an urban area. I mean, where else is, is there anything like that on

Steve: Yeah.

Kyle: Right. but there was a, uh, there was an. major sculptural project on the north face of Stone Mountain the, starting in the late seventies.

That that went all the way through the, I’m sorry, late sixties that went all the way through the mid seventies, in which a group of, of the, the racist owners of Stone Mountain Park in those days before it was a state park, uh, chiseled, a sculpture of the, of the, the three losers of the Civil War, Robert E.

Lee, Stonewall Jackson, and Andrew E. Davis, riding on their horse giant sculpture that

Steve: Really? How giant, how big is this thing?

Kyle: I, you know, a hundred meters across and, and

Steve: meters. Oh man.

Kyle: it dominates the thing out with the power, you know, I mean, just totally deface the mountain to, to celebrate these traders, these, these, these men who had betrayed their country and fought a brutal civil war. In defense of slavery.

Steve: Yeah. Hard to, hard to wrap your head around that these days, isn’t it?

Kyle: both culturally as a rock climber, you know, as a human being, a student of history, as a, as a person who thought deeply about, you know, these forces that had, had, had surrounded me as I was a child growing up in Atlanta. This was a, there could not be a strong, a, a bigger contrast between my worldview and, you know, this, this giant, giant sculpture of the three losers. and when they, and when they finished the sculpture, uh, I had done quite a lot of rock climbing with my friends on the base of Stone Mountain on either side of the sculpture. So we weren’t at risk of, you know, of any falling debris and basically surreptitiously under the tree line so that the, you know, park rangers weren’t, you know, bothering us. Um. when they finished the sculpture, they shut down Stone Mountain for rock climbing forever, and it’s never been allowed since then.

Steve: Wow. Wow.

Kyle: That was, to me, both a, you know, that happened when I was, when I was, uh, I was 16 years old and when, to me that was both, both. A physical assault to me is a climber that, that you would, you would, uh, you would take this terrain away from, from all the people who, who really enjoyed it. And also a cultural thing that, that demonstrated, know, what a, what a racist to antisemitic culture. Atlanta was, it was the most progressive place in the south in those days, in the seventies. But

Steve: Mm

Kyle: it was, but it was, that was the culture of it. so when I was 16, I got my driver’s license in Georgia.

Then you got your driver’s license and you were 16 years old and I got my father’s car that summer after I finished rock guiding in North Carolina for my job, that and I drove to Boulder, Colorado. It was an epiphany for me to come to Boulder, Colorado. There was no racism, there was no antisemitism here, climbers, the whole culture was built around climbers, and the climbing is everywhere here.

Steve: mm.

Kyle: weather is fantastic. are no giant bugs on the route that you’re trying to climb through. You know, it just, it just blew my mind how great it was out here, and I realized that, that this place and this culture was where I always belonged. It was where I really should have been my whole life.

Steve: Yeah. Yeah. I, I want to go back to that for a second. ’cause one of the things I wanted to ask you about is like, how that felt as a Jewish kid growing up in, I mean, I, I’m not going out on a limb here, I don’t think to say that, uh, you are in a minority, you know, cultural and religious group in Atlanta at that time, and so that, that must have also affected you, right?

Like, that could like, kind of, did you have that f feeling like, oh, that could be me. Yeah.

Kyle: race, uh, racism and antisemitism were the background noises of my youth. You’re

Steve: Mm-hmm. Mm-hmm.

Kyle: You know, and it’s in that society and you, you, it makes you feel an outsider. And climbers are very much outsiders in most of the places that they, that they exist,

Steve: Mm-hmm.
Kyle: most of the places they live.

Steve: Yeah.

Kyle: feeling, don’t you think amongst climbers that you’re an outsider to the culture you’re in?

Steve: Yeah, I think that that is true, but not, but you know, you’ll notice, and of course there’s places like whether it’s Boulder or Shaman or even here in ATO, where I’m living right now, I always make the analogy like if you, if you go to Shaman or Zerat or calls on Ner the Village up the road here, that’s the base, the highest mountain in Austria. You, you know, if you go to the Central Square, there’ll be two buildings there. One’s gonna be the Catholic Church, and the other is gonna be the Mountain Guide office. And those two things are, are the bo the like two most important cultural institutions in those villages. So if we go to a place like, you know, shaman or Boulder, I mean, Boulder’s obviously, you know, doesn’t have a Catholic church in its maid square, but, or probably about guide office.

But they, um, there’s instead what, what do you have, I guess, I mean, I get, I gotta make a Okay. Yeah, there you go. That’s it. That’s, yeah. Detune mountaineering in the, in the brewery. What’s the name of the brewery again? It’s got like a sun for the logo. I can’t remember. so, so that would be the, that would be the replacement. But if you get to one of these places, you, you aren’t the minority, uh, you’re not the outsider or you’re like part of the core group.

And I think that’s part of what attracts us. Uh, you know, I don’t have so many friends that live in, as do you that live in Shaman or Andmore Alberta or like, you know, it could be Reto where you, where you are, like mountain guys are, are part of that. And, and that I have to say, you know, you’re a generation ahead of me, but you know, that, but for sure wasn’t that way. You know, 50 years ago where, where Mountain Mountaineers of any stripe had any kind of, uh, what’s the word? Like, um, social. Social haft, social like, uh, importance. I mean, maybe in, in Europe. I think maybe that was a, came around a little earlier. You had of course, like, you know, Maurice Herzog and, uh, the gr the great heroes of the first descent of the 8,000 ERs, all that, that race through the, the twenties, thirties, forties, fifties. But those were, those were exceptions. Those were the, those were the, that was the, was the beginning, the old times.

Kyle: When I came to Boulder in the summer of 1975, I think it was the only place in America where there was a true city with a climbing culture. And, and as I said, that had a just a profound effect on me. As a young climber. I mean, and, and there was no, as I say, there was no racism here. There was no antisemitism. What there was was elitism. Boulder’s always been an elitist place, and it’s the two things that have characterized Boulder are elite human capital and elite human performance. And as a venture capitalist and a, and a and a mountain guide, I’m down with both of those.

Steve: Right, right, Yeah, I hadn’t thought of that. That is, that is true. All of those things you say are true, whether it’s the, you know, city with the climbing culture and all the, the elite performance, you know, um, I, I’ve never, never met him, but, uh, Jim Collins talks about that. Quite a bit like his books, or even in his speaking that I’ve listened to where he’s talking even about his wife and her, her decision to get into triathlon and some of that story.

And it is, I think, part of the culture. Like we just going to, we’re gonna, we’re gonna do this thing we don’t know, you know? And of course you start off like everybody, like, I don’t know if I can do this, but if I’m gonna do it. I mean, that’s the mindset in Boulder, I would say, if I’m gonna do it, I’m gonna be the best I can be.

Absolutely. And maybe I’m gonna be the best in the world. Actually. Being the best in the world is gonna be my goal, and I’m gonna find out if I have the genetic potential to achieve that. that’s sort of the starting, that’s a starting gate. Is, is that, I mean, not everyone, of course, but like that’s, that’s not uncommon in a place like that. Yeah.

Kyle: absolutely. The, the, the, the interesting thing in Boulder is that there are so many elite athletes in each of their respective sports that no matter how good you think you are, it’s your, it’s your thing. There’s a thousand guys you’ve never heard of in Boulder that’ll kick your ass every single day.

Some
Steve: A hundred percent. Yeah.

Kyle: for some people that’s a, that’s a devastating ego. Blow, blow. They can’t handle it. You know, they just can’t handle not being the best of their thing. Where they came from, they were the, they were the elite, right? And here they’re just another schlubby guy who does the thing.

Steve: Hmm.

Kyle: for others like me, it was in inspirational to be surrounded by a community of, of of world-class thinkers and world-class athletes who are, who are devoted to both of those, both, both their intellectual development as well as their, their, their sport.

Steve: What goes into creating, I mean, that’s like a question. Nobody knows the answer, but I’m gonna ask it anyway. What goes, what makes, how does that happen? What does the perfect storm.

Kyle: It’s partly geography that brings to a place. You know, it has to be an attractive place and there has to be a concentration of the elite human capital. As Jim Collins says, gets the flywheel going, you know, but then you know, a lot of it is luck and timing. There has to be some successes that feed on themselves. And here in Boulder, we had some early successes in the 1970s in the tech industry. IBM moved to town. Storage Tech became a large company. Amgen was started here. There were some meaningful early successes. Celestial Seasonings was the foundations of the national foods business

Steve: Hmm.

Kyle: Um,

Steve: The lab there, the university there.

Kyle: university of Colorado is here and is an excellent public university.

The National Laboratories, nist, NOAA, and Carr were formed here in the sixties. There was a generation elite human capital that came and got the flywheel going so that when I first

Steve: Hmm.

Kyle: in the seventies, I could see it happen and I realized that this is the place I wanted to be. And then when I finished business school and came back here full-time for my. For my career to start my career. There was no question that this is where I was gonna do it.

Steve: Did. If, if, so you had that, you were able to recognize that. Are you able to help people recognize those other places? Maybe boulder’s not their jam, but maybe like, what do you say? What would you say to like a younger person who’s looking for their version of, of Boulder? Or is there just a list and there’s only like, I don’t know, three places on it?

Kyle: I, yeah, I, I think the latter. I mean, I, there’s really, it, this, this phenomena of a elite human capital the flywheel in a, you know, in a, in a, in a segment or in an industry or in a certain thing. It only happens in a couple of places. In the venture capital business, it’s Silicon Valley for, for technology and Boston for life sciences,

Steve: Okay. Mm-hmm. Mm-hmm.

Kyle: still kind of a frontier in those, in those markets. But it’s an important one. It’s, it’s, you know, it’s in the top 10. By investment in both of those, both of those segments, and it’s a city of a hundred thousand people. So on a per capita basis, it’s, it’s multiples of those other spots.

Steve: Yeah. So I wanna go back to your childhood for a second and, you know, I wanna drill in a little bit on this, something you wrote about, and it’s something I’ve experienced too, but you, you said you, you didn’t feel like your, and I may be paraphrasing here, but you didn’t feel that your intensity was welcome, that you were an intense kid.

You used this phrase often, and you also said precocious earlier, a few moments ago, a few minutes ago. How did, did that, how did, what was your experience of that as a kid? And, and did it make you feel like an outsider? Um, were your, you know, you were reading a lot, then you discovered climbing.

You could go deep into that. Were these, did you just sort of find like these niches where this intensity was accepted and you could kind of relax and go into those things?

Kyle: I had a lot of, I think in retrospect as a kid. I had a lot of physical and intellectual energy, and I had to expend those on something. And fortunately for me early on I found my climbing gene was active, and, and, and I could, put all of that into the, my, into my climbing

Steve: Yeah.

Kyle: that was a good place for me to expend my energy.

Steve: One of the things that I think I want to, I’m curious if you agree with this, but I would venture to observe that. Back then, and I’m just gonna say it was much more complex to become a good climber than it is now. And now you can become a good climber in the bouldering gym with no more investment than a, you know, through wear, wear out five pairs of shoes and go through gallons of chalk.

And I can guarantee you’ll be like a pretty good climber. Back then, it was like ki it was really hard to figure out all of the, art climbing and whether it was, you know, even just guidebooks were completely different thing then. The roots didn’t have often anchors. You didn’t really know how you would get down. Uh, forget about like, photos with lines drawn on them, like, you know, placing gear. Like, you know, mean we both remember the advent of camming devices. I mean, that was that long ago. And now it’s just, you know, second nature to all of us, right? Like, um, not that all the safety equipment that you mentioned earlier, like we just all routinely wear helmets.

They’re so light and an intrusive now, you know, we don’t hardly think about it. Um, in just every way. It’s so much easier. Do you think that that’s cli changing, climbing for the better, for the worse, for the neutral? Like how do you see that, how people go into, into climbing now? Because one of the things with mastery that you have to be really obsessed to become really good. And the, in the old days, like had to be obsessed to even get started. And so you were more likely to become good. ’cause you started off as a intense, obsessed person. And now I think a lot of different personalities come into climbing. Am I off base?

Kyle: I, I think you’re right. I think, I think climbing and, and Alpinism in general have been democratized.

Steve: Hmm

Kyle: accessible to people now. They’re not as dangerous. Mountain guiding is a form of mentorship that’s available to everyone.

Steve: mm-hmm.

Kyle: my generation, mentorship was the only way to become a good rock climber. There wasn’t really a lot of rock guiding going on, and, and, and there were no climbing gyms. So the way people entered the sport is they had a friend who was in, who was a good rock climber and taught them how to, how to climb.

Steve: Yeah.

Kyle: And, and to a large extent, you were self-taught until I went to do my guide training in Shamia in 1980.

I had never really seen, uh, you know, what High-End Mountain Guides did in terms of mentoring and teaching their clients. I didn’t understand any of the pedagogy around, Alpinism,

Steve: Yeah.

Kyle: that was kind of an epiphany.

Steve: Yeah.

Kyle: thing was true in those days of, of, of powder skiing. I mean, you know, the skis were skinny. it was really complicated to learn to be a powder skier. It was painful to learn to powder ski. And you only had a few days to do it, and you really, the backcountry thing was, was unknown. The, the avalanche information was, was obscure and there were only a, a couple of people in the country in possession of real expertise in that area.

Steve: that’s true.

Kyle: you can take an area class, you, you’ve got these nice big fat skis and all this high tech gear and, and it’s been democratized. It’s available to people who, who maybe don’t, aren’t completely obsessed with it the way you and I were

Steve: Yeah. Yeah. I wasted a good 10 years of my life learning to ski telly. That was, that was completely unnecessary. A waste of time. I mean, I wouldn’t say I did enjoy it in sort of a somatic statistic way, but, but, but I’ll never tele ski again in my life. I could absolutely promise that. But that was the only way to ski in the back country because you couldn’t, you couldn’t go, like you couldn’t walk otherwise.

’cause it was just alpine gear or tele gear or cross country gear.

Kyle: I bought my pair of, uh, of, uh, Fisher Air Carbons with the silver Atta bindings in

Steve: Uh,

Kyle: Shay, you know, for my guides course. uh, and the guy at Snell says, oh, you buying some Rendez skis? I said, R, what does that mean? He goes, that means you can’t tell he ski.

Steve: friends for, cant tell. I think that’s great. Oh man. Um. The, so, you know, I, I do think it’s important that these things become democratized because I truly believe, I mean, that’s what the whole mission of Uphill Athlete is around, and I mean, it’s been around some, and we’re gonna get to these, some of your contributions you’ve made through Air and am American Mountain Guide Association and so on. It’s, we both believe so, uh, passionately in the, like the good of, of being in the mountains and, and, and being in the mountains with friends and, and doing these things and climbing and skiing and all of this that, that we want, that we both actively participated in developing that, that for others. So, I, I don’t want people to get the idea that we’re gonna pull off, try to like go into some off on some elitist tangent and talk about how, how back in the good old days, Kyle, you know, we’re not gonna do that because I actually. I, I think it just self-selected for a certain kind of person that was a very narrow person, uh, like personality type. And we were all, I was definitely and still am in many, in many metrics, uh, kind of a fringe person. Like I’m not, not in the middle of the bell curve and that’s okay. I’m just that way and that’s partly why I got into climbing.

And I think it’s partly why you got into, into climbing.

Kyle: You exemplify elite human performance, Steve, and that’s been a, real theme in your life, you know, and what you democratized with your uphill athlete training books was something that, again, I had to find through other and there was no information

Steve: Yeah.

Kyle: do I train for this sport? How do I get better at it? was a lot of, when I was a gymnast, there was a lot of information about how to become a better gymnast. There was this long history of how do you train specifically for these movements and using these apparatus in a way that maximizes your. ability to do the trick, right? And all these to learn the trick. But there was no way to learn the trick in rock climbing. You know, you had to go do the trick.

Steve: Yep.

Kyle: And, and the only, the, the way I learned to do these boulder problems was watching John Gill and Jim Holloway do the problem to duplicate

Steve: Yep.

Kyle: to understand how, how I could, how I could climb the problem as well.

And it was really hard.

Steve: And interestingly, I only learned this about, I don’t know, it was within the last 10 years when Josh Wharton told me that he just watches tons of YouTube videos of Adam Andra and Chris Sharma. And he is like, I’m just, I study their, uh, he like, is analyzing. I was like, oh, of course. Why did I never think of, of that?

You know, of course I’m not watching Adam Andra. ’cause I could never climb at that level. So it sort of doesn’t apply to me, but I need to, I can find people closer, you know? I,

Kyle: but not.

Steve: yeah, yeah. Exactly.

Kyle: Yeah.

Steve: Exactly. I can’t, I can, it doesn’t, yeah, it doesn’t apply here, but I can find people who can climb just a little bigger, higher than my level and, and learn from that, just from YouTube, which is amazing, right?

Like, again, democratization of information and, and it’s not there necessarily to, to teach people how to certain movements, but it certainly can.

Kyle: in my early climbing days. And, and when I went to college in the Gunks, you know, I would, I would, I would take every opportunity I had to watch Henry Barber climb in the gunks in the mid seventies just to watch him climb. I learned so much from his footwork and his body positions,

Steve: Hmm.

Kyle: addressed the rock with his shoulders and his hips. the kind of, the kind of, you know, he was, he, he had incredibly f he had great hip flexibility and he, he could step. highly on steep terrain, and how could he lever himself using his feet and his hips into certain positions on steep terrain? I, I could only learn that from watching him,

Steve: Mm mm

Kyle: devoted myself to watching and climbing with him. One of the great things in those days were there that there weren’t that many great climbers. There weren’t, you know, there

Steve: Right?

Kyle: a few people at his level, and it was like playing golf with Arnold Palmer. You could just go up and say, Henry, I’d really like to belay you on this thing. Can I you a catch? Um, because I’d been a, because I’d been a, um, a successful gymnast. I knew a lot about spotting and catching

Steve: Ah-huh.

Kyle: and so for, and we didn’t have any pads in those days. So for bouldering or for, for rock climbing. I was a good belayer. And a good spotter.

Steve: Yeah.

Kyle: Yeah.

Steve: yeah. That makes sense.

Kyle: I was, and I was, you know, a big, beefy kid. So, so, you know, Henry, let me blame him sometimes

Steve: I actually think that you and Henry would have similar body types. You’re both pretty tall and Yeah. So I can see how that would apply well to, to, to you. Yeah. Mm-hmm. When you moved to Boulder, what did you sacrifice in that choice? I.

Kyle: Uh, I sacrificed nothing from the standpoint of being a mountain guide or my aspiration to be a mountain guide, and a rock climber and an alpinist. In fact, I enhanced my opportunities to climb every day, which I have consistently done for the last 40 years. Uh, I gave up in my venture capital career was a chance to be on the main stage in Silicon Valley or Boston or New York, um, to be the center of attention and the center of, of, of the action. and to, uh, pursue the highest levels of wealth and status that venture capitalists about. Um, but those things weren’t, that, that wasn’t really what mattered to me. So, so I was, I I, it was a good trade off for me. It was a happy medium,

Steve: What, what mattered for you then?

Kyle: uh, early. What mattered was climbing and skiing and being able to have a career and use my intellectual gifts at the same time, I, pursue my guiding aspirations.

Steve: Mm-hmm.

Kyle: as I progressed in my career, what became important to me were the quality of the relationships and the of, of, of the companies that I was involved in and trying to achieve mastery as a venture capitalist. I had some great mentors in that world who, who had done so in Boulder and I wanted to emulate them.

Steve: Can you tell who was that? Who would’ve, can you name names?

Kyle: uh, for my first job after business school in 1985, um, before the K two expedition. It was a guy named Mercure, who was a great entrepreneur here in Boulder. He was a physicist from the University of Colorado Climber and a skier. And, um, uh, he founded Ball Aerospace, which is the largest company here in Boulder. He was kind of the Elon Musk of his generation. He invented the satellite business.

Steve: I sure know Ball Aerospace. I don’t, you know, my, my little secret is I wanted to be a aeronautical engineer when I was a kid. ’cause I wanted to be an astronaut. Like, that was, so, I was really into everything around flying and flight and aeronautical engineering and stuff. So I, I learned a lot about those, but I’m, so I didn’t know his name, but that’s super interesting.

And so he, so how did, how did that come to pass? How did you get that job?

Kyle: I, I, you know, I’d been coming to Boulder for a long time. Iraq lived here, so, you know, I felt like this was my home since that summer of 75 and after business school I had, I had, uh. had on Merck many times, uh, offered my services, had done a little consulting forum, had myself in some projects.

I guided him on the third Flat iron. Um, uh, you know, I tried to make myself useful and when I graduated from business school, I had some offers to go to Wall Street to work for investment banks, which was the typical thing you did with a University of Chicago MBA in 1985. Go to be an investment banker. Um, and, and, you know, I liked climbing in the Gunk, so it, you know, that that might have worked for me. But really, I, I, my guiding at that point was at a stage where I really wanted to be guiding as much as I was working. And Merck offered me the opportunity to do that. He, he, you know, he said If you come to Workforce, we can’t pay you like Wall Street, but, um, you can prove that you can make money and we’ll give you that opportunity and. We’ll give you April off to go to Shaman and and ski tour and you know, do the ski touring program in the Alps and we’ll give you July off to go rock climbing and rock guide wherever you’re going, which was mostly in Europe as well. And so, um, I don’t know that there were any other opportunities available to me that, that had that much flexibility in that opportunity.

Steve: But you had, it’s, it’s, you had a significant relationship with him that he even knew that those would be the carrots that would really motivate you. Right? Like

Kyle: And, and when I graduated business school, I told ’em I’m committed to this, uh, expedition to the north face of K two in the spring of So I’m going on that expedition. so I’m not gonna really start my job until until I come back in the summer of 1986. And he said that was fine. And when I, and

Steve: I.

Kyle: I came back to Boulder after the K two expedition, I showed up for work on August 1st and he said, oh, you’re here. I said, yeah. I said, you know, we loff, we thought you had low survivability potential. We didn’t know we were actually gonna give you this job.

Steve: Okay. Yeah. Yeah. I mean, a little morbid, but yeah. Uh, so tell me about this 86 expedition. Who was there? What happened?

Kyle: Uh, I was invited along, uh, support of a group of elite climbers, uh, by my friend George Lowe. George and I had done some rock climbing together, and he was a hero of mine. And for his, as you know, one of the greatest alpinists, alpinists who’s ever lived. Um, and.

Steve: could I just pause for a quick bit of context? George Lowe and his partner Chris Jones, climbed a boot on the north face of North Twin in 1972. Which I a variation and repeated with our mutual friend Mark Appraisal years, years, years, decades later. The first ones to repeat that, don’t remember what year that was now, but what I wanted to say about George is in 1972, that was the most difficult climb ever done in the mountains anywhere.

And it’s at a fast paced, two days walk from the nearest road. Really, really, really, really impressive. And he is involved in so many other things, and he’s such a great, wonderful human and guy in, in so many ways, and I admire him in so many ways. So shout out to George, if you ever listening. Uh, so much.

Kyle: to this and, and now he’s moved to Boulder and, and, uh, he is in an apartment here and I’m hoping to go climbing with him next week. I mean, it’s just, you know,

Steve: Cool,

Kyle: with your heroes is one of the greatest things in life, isn’t it?

Steve: isn’t it? Mm-hmm.

Kyle: Anyway, George, George organized this expedition, uh, and, uh, uh, it was really some of the greatest alpinists of, of my generation that he brought along.

You know, it was, it was Alex Lowe, uh, Chuck Quinn, uh, Dave Cheesmond. Catherine Reer, who was a fantastic woman, alpinist of that generation. and they all, and, uh, and Steve Swenson, another great climber, another great climber and, and, uh, alpinist of, of my generation. So very much the elite, the, a team of, excuse me, the, the, a team of American climbing at that point to try the north face of K two, which, uh, up until that point, you, you had to go through China and no one had gone, through China.

All the, all the people who had climbed K two had gone through Pakistan Bal Trench, so there are no porters available. There was a long march up the K two Glacier. It was gonna require a lot of logistics and a lot of planning, and there was no guarantee you could even get to the base of the thing across.

Nobody had tried to get across the two Glacier,

Steve: Yeah. Not to mention a bunch of river crossings where there’s no bridges and

Kyle: camels and, and Kiki tribesmen and, and you know, the Te Lamican Desert and I mean, it just. It was an adventure and, and, uh, and they needed, you know, they needed worker bees who were competent alpinists, but who weren’t at their level to come along and help schlep all this stuff, you know, put ’em in position so they could climb the, climb the north face of K two.

So that’s what I signed up for. I’d never been on a Himalayan trip. I thought it’d, you know, it’d be interesting to see how a big expedition like that would go. And, uh, I was at a point in my life after business school, but before I started my career where I had the, the space to do

Steve: Mm-hmm.

Kyle: um, and it was, it was an interesting, actually, I, I mean, I learned the, the key takeaway for me really is that I’m, I had just, I, I, it.

I’m glad I did it, but I have no interest in, in Himalayan Expeditioning,

Steve: mm

Kyle: Um, there was no concept of your style of climbing in the, in the, with Marco and, and Vince in the, in the high mountains where you’re fast and light and climbing an alpine style in these big peaks. That was not what was going on, man.

It was spools of fixed ropes. Moving stuff up the mountain and

Steve: Yeah.

Kyle: a construction project and I just wasn’t, it wasn’t that, in that part of it was not that interesting to me, you

Steve: Yeah. That was starting to happen with some of the polls. You know, some of the Brits, you know, you had, you know, Borman Tasker, you know, you had, uh, uh, you know, EK Tica, um, Christoph Licky, some of these, uh, some of these

Kyle: a Reinhold Nest and Peter Haer climbed the, the,

Steve: yeah, of course. Camp

Kyle: climb the hidden peak fast Alpine style,

Steve: Yep, yep,

Kyle: were starting think that, but

Steve: yep.

Kyle: going on

Steve: Right.
Kyle: the six.

Steve: That was the exception to the rule.

One thing I wanna say though, ’cause my first expedition to the MLA was similar. It was like I was with a big expedition. There was 18 of us, and I signed up to be a worker bee. I was, I had my 19th birthday in base camp. I was really young. And uh, it offered, it, it offered an on-ramp to that world where, I mean, I had no, like you, I had no illusions that I would go anywhere close to the summit.

It was a nunga parbat. But I was like just so happy to be there and be, I was just, I was so excited to just carry a tent up for somebody that needed to take a tent up to the hike camp or I don’t know, whatever. Like I was just beyond excited to do all that. And I think that we, now that so many more people climb out. All the private alpinists, climb al Alpine style and the commercial guided groups all climb expedition style. And I, I feel like there’s this vacuum where there aren’t many, at least from the West, aren’t many, you know, expedition style trips going where, where you can take 18 people and half of them can be, you know, relatively inexperienced and, and learn a lot.

I mean, I remember just sitting around like hearing so many stories. I mean, we had guys on that expedition that had climbed five 8,000 meter peaks in 1990. You, I mean, that was like a major accomplishment. Anyway.

Kyle: really looked at it as an opportunity for mentorship too, because I wanted to see Lowe making decisions under conditions of uncertainty. You know, how, how does he think about when to go and when not to go, and how to position people and when to climb and what not to climb. He’s so thoughtful and so successful in the mountains so, so of all the, all the summits he’s gotten, but also so, such, such a durable, survivable guy that he, he clearly was a great decision maker in the mountains and I was interested in observing that and, and hoping for some mentorship though.

Steve: Had, had you sort of intellectualized it to that degree at that time

Kyle: Yes.

Steve: you had, what did you find? What were your notes? What was in your, what was in your journal?

Kyle: The guy, the guy was, thought deeply about everything he did from the micro motion and movement around a rack in which direction to take the, the route of travel to the big picture, how to, how to, how to keep the, the train going to make sure that the supplies all made it to the next place so that everyone was positioned. Um, a lot of the, a lot of the deaths that

Steve: I.

Kyle: on K two were Al Raus and Julie Tellis. They were, they were, they were pinned down by a storm, unnecessarily by their own group because they weren’t coordinated in terms of the, the, the package of stuff that needed to arrive.

Steve: Yeah, yeah,

Kyle: George was, was, was brilliant at that.

Steve: yeah. When you’re sitting around with your VC friends, do you tell them stories about like George and his decision or like, you know, how much of that kind of crosses over into those other conversations? Or does that live totally separate in your,

Kyle: For most of my career as a venture capitalist, my partners were pretty uncomfortable with the idea of talking about any of this stuff. Such a fringy thing. And I’m so actively doing it, you know, as a,

Steve: your partners or your climbing partners?

Kyle: VC partners, climb partners. We talk about this stuff all the time, know, you know, Slater for instance, Rob Slater, was, was, was, we did a lot of climbing before he went on his K two expedition.

’cause he really wanted to know what it is that I learned and what could he take away from that. He was going for a fast and light.

Steve: Yeah.

Kyle: style expedition. But what could he, you know, what could he take from my experience and could I tell him That he, he was a voracious, like you and me, he was a voracious reader of the literature, and he was anxious to interview everybody who, who had some experience on that mountain. but my partner, my venture capital partners, my investors and my, partners at the time, they, they thought it was kind of a fringy thing, and they’d have a hard time explaining it to people this stuff was about. So I, they actively discouraged any mention of the, you know, this kind of stuff, this, this, you know, devotion to Alpinism and to,

Steve: Interesting.
Kyle: skiing and to,

Steve: Is that changed

Kyle: yes,

Steve: and what’s a conversation now? Are they actively interested in it?

Kyle: Because, you know, there, there was this, you know, as, as outdoor sports generally, and backcountry skiing, guiding and rock climbing became democratized. You had sort of, it entered the popular imagination, it became much more an interesting thing for people to hear about the, the, the risk management lessons that we learned from, from mountain guiding and how those applied to venture capital.

And I started writing the blog about 10 years ago talking about how being a mountain guide and being a venture capitalist we’re in many ways the same, same job. And, and some of those lessons that we learned from those two things, how do they, how do they apply to each other and what, and, and, and how, how those are effective, uh, effective tools in your, in your, in your arsenal of, of, of, uh, things you do.

So that became a more accepted and a more, you know, sort of, sort of out in the open idea. But that’s only pretty recently, Steve, I’d say since sort of 2010. And now with publishing this book, which is sort of a, a book about mountain guiding and venture capital and the culture of Boulder Ventures. I, I would say we’re completely out in the open now.

Yes.

Steve: Right, right, right. Yeah. You’re, you’re openly giving away your quote unquote secrets in a, in a sense, right? Because that’s how you, you know, we’re gonna get, I think that that’s super interesting, but I want to get to that a minute. We gotta, you mentioned Rob Slater and, you know, I talked to who interacted with Rob, you know, obviously he, he died in, in K on K two and it’s, so, I never had the, had the honor or the luck to meet him, but everyone I talked to who interacted with him just had. Like these incredible stories about him and his energy, and his climbing and his intellect and all these things like when you go through your VC life, do you meet Rob Slater’s?

Kyle: Yeah.

Steve: And how do you know, like, what’s a Rob, like a, in, in the name of Slater? May he rest in peace? What? What is that? What is that?

What is that of, of being in that?

Kyle: I mean, Rob, Rob, like all of us had had a bad gene.

Steve: Yeah. He had it bad.

Kyle: He had it bad. a bad gene, and he had to go rock climbing every day.

Steve: Yeah.

Kyle: But he also, he, he had a desire to, to do things at the cutting edge that I’d never really seen before. You know, I, he, he, he not, he would not, he was a fantastic free climber, one of the best of my generation.

I mean, just, just as solid as any of the, the, the best elite rock climbers were. Um, he took that to the mountains occasionally because for him, ice climbing and mixed climbing was pretty trivial compared to the level of rock climbing he was interested in.

Steve: Yeah,

Kyle: He also, he also in rock climbing, was very interested in pushing the standard ascending any piece of rock by any means necessary.

And he was really the greatest aid climber of his generation. I mean, some of his roots on, uh, El Cap, uh, Wyoming Sheep Ranch and, and uh, you know, see a dream set. There was, there are pitches up there that still are un repeat and people just, or, or, or if they are repeated it’s ’cause people have added lots of bolts to them.

Steve: yeah, yeah.

Kyle: And Rob would just hook his way up El cap for 30 meters on unknown terrain

Steve: Look.

Kyle: else would ever do. Right.

Steve: Yeah. And if, and, and, and to put so people can understand that a hook is like a, literally a, a metal hook. And you, you clip an, it’s got a little sling on it and you clip a rope ladder to it called an eighter or an atria. And then you, you place it on top of an edge or a flake on a piece of rock. And you know, a flake is sometimes they can break or kind of pry off, or edges can be small.

But the thing is like when you’re doing that and you fall, there’s no to stop your fall, to rest your fall. So if you’re doing this for 30 meters, you’ve just gone 30 meters and there’s nothing to keep you from falling. Now 60 meters plus rope stretch, which is a massive fall, and you have no idea if the little edges that you’re hooking on are ever going to continue. sometimes they just stop. Right, right. It’s like it’s, who knows what happened. Some, the glacier came down Yosemite Valley, you know, million years ago, and it left some edges and some places are just polished as as a sheet of glass and you don’t really know. So to be up there just hooking his way into, towards some other crack system is incredibly bold. it’s, I don’t, people don’t really, I mean, outside of maybe Alex Huddle, like, I mean, nobody really operates in that head space anymore.

Kyle: Exactly, and, observing him and his risk management and his decision making was really, was really interesting for me. that that was not who I was. I, I felt the analogy is more, Rob was more of an entrepreneur and I was more of the venture capitalist in our

Steve: Hmm.

Okay.

Kyle: really ready to hang his ass out in space. You

Steve: Hmm.

Kyle: go for the objective where I’m more circumspect and wanna. Wanna manage the risk at a, at a higher level. The other thing is he’s one of the first base jumpers in America, you know, jumping off the sides of the cliff. And I, I climbed with him a bunch of times where we got to the top of the objective and he jumped off with a parachute, you know, that was a new idea then.

Steve: Yeah.

Kyle: now, but that knew what the equipment and the, and the techniques and stuff. But he really, that was interesting to him. That was, what he liked

Steve: Mm-hmm.

Kyle: risk management at the absolute edge of elite human performance.

Steve: Yeah, I will by the, the episode that’s gonna air before this one is actually with Randy Levitt, and so he was ba number, I forget, like 50 or something, like really early. He was right there. I didn’t, Rob Slater did not come up in our conversation, but I know for a fact that those two, uh, did some base jumping together and some climbing in Yosemite.

Kyle: at

Steve: percent. A hundred percent. And they climbed in the valley together. Yeah, they were there at the same time. They’re the same age. So, um, you said a couple of things I wanna try to follow up on. One was that, uh, you know, Rob was interested in the edge of performance or something to that effect.

Like how did you know that, what did, what does that mean exactly? Who, who

Kyle: was interested in decision making at the edge of elite human performance

Steve: decision making.

Kyle: making. Do I jump today or not do, can I, can I stretch this, this hook pitch all the way to the next crack system where no one’s ever gone before.

Steve: you describe yourself as a sort of risk manager at the, at a higher level. Talk to me about the difference between someone who wants to make decisions at the edge of. Human performance or human achievement who wants to part, like, partake in the upside of some of that, uh, what unfolds and what can be developed on top of that kind of exploratory mindset. Talk to me about.

Kyle: It is a different mentality. It’s the mentality of the entrepreneur versus the mentality of the venture capitalist. Rob was Rob. Rob was, Rob was trying to, to push the, the, the margin as far as he could and was willing suffer the consequences as he did dying on K two, pushing the margins of what he was capable of or what anybody was capable of in those, for me. and mastery and integrity were the things that I was trying to create in my business and in my, in my guiding that, that that enabled me to have a long view and a long life and a long ability. I didn’t want to die on the north face of K two and I wasn’t willing to, to do what it probably would’ve taken to, to push it to the top. You know, that was not in my nature.

Steve: I know it sounds obvious to you when you say Rob was an entrepreneur and I’m a venture capitalist and what that means, but it, I don’t think it’s as obvious to until you just explain. In that way. So then when you are standing at the, you know, at the onset of your career, I mean 85, 86, looking, looking ahead, this maybe late eighties, you have that awareness at that time? Like it’s a very different game plan to be, have that awareness and be like, I am going to look for relationships. Integrity is important to me. Uh, I get a manage risk. I gotta, I know I have to expose myself to some risk to make progress and gains, but I don’t wanna have too much, I don’t wanna lose everything. Did you have that awareness

Kyle: Yes, Steve. Early in my career

Steve: interesting.

Kyle: I was obsessed with the mastery and there weren’t very many of them out there. There weren’t very many venture capitalists in the eighties who had already proven themselves to be masters of the form. built funds from scratch. It was the first gener that was the first generation of American venture capitalists from Silicon Valley and from Boulder and from coast. And they were accessible to me as a young venture capitalist. I could go to Silicon Valley and, you know, and call up Tommy Perkins or, or, or Paul Ferry in Boston or, or you know, um, Tony Ednan at Venrock. And I, and I could, I, I could call ’em up and go have lunch and ask ’em questions about their deals and tell them what I was doing.

And they were interested in, you know, in, in what, what we were doing in Boulder, Colorado. And, and, and they were happy to do that. don’t think that’s accessible to young venture capitalists anymore. I don’t think that exists. ’cause it’s

Steve: Interesting.

Kyle: institutionalized kind of business now. But in my generation, when I was 27, 28 years old, they were, they were available to me. A lot of them like to go skiing. I mean, it’s always been a thing in the venture capital business. They come out to Colorado, go skiing. So I had an opportunity to guide them, you know, powder skiing or skiing at Vail. Um. And to interact with them in a, in the field in a way that probably wasn’t available to other venture capitalists.

Steve: Mm-hmm.

Kyle: the young venture capitalists of my generation, there weren’t that many, maybe a dozen of us who had good jobs with name brand, Silicon Valley or Boston or New York funds. Um, they all skied and, and they would all come ski with me and we’d all have a great time together. So there was a, a real comradery.

It, it wasn’t a competitive environment at all. It was, it was a real collegial thing and could learn from each other and use each other’s networks to, to, to, to try to achieve mastery like the guys that we were, that we were emulating.

Steve: Hmm. That’s so interesting.

Kyle: very aware of that at an early age, and it’s something I sought out the same way.

I sought out the best rock climbers of my, of each of my generations to, to see what I could learn from, from observing them and interacting with them in the, in, you know, in the terrain.

Steve: Where did that humility come from that allowed you to see the wisdom of. Pursuing like these relationships with these, with these, you know, a team as we, as I think you said, you know, of the Alex Lowes of venture capital. Did that come from climbing? Because you’d already been through that with Hot Henry Barber and you know George Lowe iii, and, and you, you knew that these giants of climbing were also human beings that needed a spot or a belay or a load carried.

Kyle: I, I had a lot of energy and a lot of intellectual curiosity, and I wasn’t intimidated by the reputation either in the venture capital world or in the climbing world of these, greats because frankly, as a rock climber, I, you know, I was a pretty good rock climber for my generation. I. You know, I was a solid five 11 track climber.

And
Steve: Yeah.

Kyle: you know, in those days, in the seventies and eighties, that was a,

Steve: Yeah.

Kyle: elite level. I wasn’t, I wasn’t Alex Lowe or, or Rob Slater, but I could climb with them, know, I could play around with the golf with Arnold Palmer and not, and not, uh, and not embarrass myself. I could, I could, you know, I had the chops to go because I’d been trained by mert MCC Cure in Boulder.

I, I had the chops to go hang out with Tony Evan, who was the greatest biotech venture capitalist of his life, and manage the Rockefellers Fund, or, or Paul Ferry, who is the greatest tech venture capitalist in, uh, at Matrix Partners in Boston, or Tommy Perkins who started Kleiner Perkins in Silicon Valley.

I, I, I was not intimidated to call those guys up and tell them about a deal I had in Boulder. I would never go to visit them I had a deal to show them. I have an opportunity to show you, and that is just the currency of our profession. Yeah.

Steve: Right, right,

Kyle: I wouldn’t, I wouldn’t call up, you know, I wouldn’t call up Henry unless, you know, I wanted to go climbing.

Steve: right.

Kyle: Let’s go climbing Henry,

Steve: Yeah, and the weather’s good and you have a route you want to do, and.

Kyle: route. I wanna do, I’ve never done this thing before and I’ll hold the road for you on it if you wanna, if you wanna lead it. ’cause you’ve gotta dialed and I don’t wanna see how to do it properly, you know? Right. I think, I think a lot of, you know, a lot of that was just intellectual curiosity on my part and, and, and not being intimidated by the reputation of these people. know, and, and let’s face it, in those days in the eighties, the only reputation they had was amongst practitioners. As you say, nobody would know in the airport who these people were. Right. Henry could go anywhere he wanted in the world. Nobody knew who he was except for rock climbers. know, he was on a, b, c wide world of sports.

That was like, no one had ever seen anything. Like, it was a great segment too. I’ve got on one of my blogs and, you know, but he could still be completely anonymous outside of the rarefied atmosphere of, of international rock climbing. Um, he, you know, today, these young entrepreneurs, the guy who runs OpenAI or the guy who’s the, the, the CEO of a, of a, of a successful tech company, they’re in Silicon Valley.

They’re, they’re celebrities, you know,

Steve: Uh, I mean, if Sam Altman shows up right now, I’d for sure know who he is. There’s no question I know what his voice sounds like.

Kyle: well, and he’d have an entourage of 30 people around him who were managing him and, you know, right. and these young venture capitalists who are so successful in Silicon Valley, they’re the same way. they’re all just obsessed with money and status in their own thing. And my generation of venture capitalists who learned and was fortunate to have been mentored by this group of foundational venture guys inculcated their philosophy in their culture, which was. what we are doing is nobody’s business but our own. us and our entrepreneurs, and we’re building these businesses. And that’s not about or, or, or the public information. There’s no value to exposing to the public what we’re doing here. ’cause it’s so cutting edge and so wacky that, that people just, you know, people, people PPO us and the entrepreneurs were not Elon Musk.

They weren’t, you know, attention seeking, attention seeking, you know, cutting edge individuals. There was no attention to ’em at all. Well, they appeared on the Forbes 400 list as one of the richest guys in the world.

Steve: Yeah.

Kyle: it wasn’t until Bill Gates and, and Steve Jobs sort of the prototypical founder, entrepreneur, billionaire

Steve: Celebrities.
Kyle: were the ones who kind of that persona.

It

Steve: Hmm.

Kyle: until them, you know, nobody knew who Andy Grove was at at Intel, unless you were a venture capitalist, you know.

Steve: When did it become about money and status and why? I.

Kyle: the bubble of the, the tech bubble of 99 2000 is what changed the industry. The money got bigger. Silicon Valley, clearly out distance every other place as a, as a, as the terrain, the best terrain for this activity. uh, you know, a generation of venture capitalists got, got really rich and, and the press kind of, it captured the imagination of people. The rise and fall of the internet bubble. And of course, the internet changed society and changed technology and, you know, change the world. there was a recognition, I think, that these, uh, that these wacky ideas and companies from Silicon Valley really had a major impact and that America is clearly the leader in the world in this stuff. combination of all that and the Bill Gates built Steve Jobs kind of personality thing. that that changed the industry. That’s when it became a, you know, a public thing. Much like, I think the free solo movie kind of changed people’s perception of, of rock climbing. Now. It became sort of a mainstream thing, don’t you think?

Don’t you think Free Solo was kind of a watershed moment for, for rock climbing?

Steve: a hundred percent. A hundred percent. And nobody’s ever asked me about this before, and I, I do have a lot of thoughts about this, you know, but, um, I don’t think we have enough. for all of that. Uh, but let’s, let’s pick that up another time or another date. ’cause I think you’re abso absolutely right. again, it’s like, you know, it’s, it’s not to judge, is better then, or it’s it’s worse now or I don’t know any of that. What I, but what I’m curious about, and I don’t think in climbing it’s about money and fame because obviously climbing roots doesn’t scale the way, like, I don’t know the next best or the next LLM is going to, just not even, not even the same. We’re not on the same sheet of paper. So, so let me get this straight.

So the, the bubble happened, I mean the bubble burst too. So that’s why I’m a little, where I’m a little confused because of course a lot of people got paper rich on the way up. But then the bubble burst and they got paper became paper poor. But it came, it became about money and status, at least in society’s mind.

Kyle: everyone’s imagination. It was front page news,

Steve: why, what I, I, I almost wanna say, what I wanna ask is what went wrong? Like, know, because you’re, you’re, you’re not a person and we haven’t even gotten to AIE and a MJ directorship and that stuff. But you, you’re not a person who has been out there for money and you know, or fame like I know that because we’ve known each other for a very long time, and we’ve skied together and we’ve climbed together, and we’ve had lots of conversa, we’ve slipped whiskey together and had lots of conversations.

So. That’s, I think the, that’s the, that’s I think the, the heart of it, right? Like, I mean, and you know, when I talk to people like you or when I talked to Greg Penner a few, uh, weeks ago, like it’s the same, same message. Like he’s also, like, he, he also like had, I don’t think he’d ever done a podcast, so chairman of the board of Walmart, he’d never been on a podcast before. So Interesting. Right? Like compared to, I don’t know, people going on, you know, Joe Rogan every chance they get and five hour episodes, which is also interesting, like part of me loves the transparency and I, and I do get sucked down the rabbit hole of hearing these wild kind of trains of thought that some of these minds go down.

It’s, it is sort of fascinating from sort of a, but I still wanna understand where why it became about money and fame or money and status status. I’m, I’m, yeah. Sorry, I was con Um

Kyle: I don’t think venture capitalists, even to this day, are famous,

Steve: hmm,

Kyle: Silicon Valley it’s about status and relevance.

Steve: hmm

Kyle: have lots of money now, so it’s really about status

Steve: hmm.

Kyle: and where are you and, and that’s a, a human, you know, a human characteristic. This kind of within the context of elite human performance and elite human capital, people are competing with each other

Steve: Mm-hmm.
Kyle: to be, to see who’s the best, right?

Steve: But what you described from like the beginning of your career, you could describe like a, um, you know, a, a collaborative environment and now it’s, you’re describing a competitive environment.

How do we get back to collaboration or do we

Kyle: no going back. There’s no going back.

Steve: Why?

Kyle: It, it’s too big and too important. And these centers of venture capital like Silicon Valley and Boston are too well organized. Too many people trying to, trying to climb their way up the pyramid, we’ll never see the eighties in rock climbing or in venture capital.

Again,

Steve: Hmm.

Kyle: I was a moment in time and I’m, I’m really grateful now in my life to have experienced it.

Steve: hundred percent. Yeah. Are you a little sad, melancholic?

Kyle: Nope.

Steve: Why?

Kyle: the, uh, do you ever seen the, the, the, um, documentary about, uh, Jimmy Iovine

Steve: Mm-hmm.
Kyle: Dr. Dre and their partnership,

Steve: Mm-hmm. Great movie. I’ve seen it a couple times.

Kyle: fascinating and, and Jimmy Iovine, who I’ve met is, is fantastic entrepreneur and know, one

Steve: Yeah.
Kyle: of the inventors of the music business,

Steve: Yeah.

Kyle: music business.

Uh, and Dre says they’re, they’re asking him about his gangster rap days, you know, and all the. the violence and, and stuff that went on death, you know, in the gangster rap. And Dre looks at the interview and he says, you know, what’s behind me does not matter. only interested in the future. And I, I, I completely embrace that.

Steve: Hmm.

Kyle: of a venture capitalist and a mountain guide. I, yeah, I’m happy for all the things that I’ve done, but what matters is the future. How can I use all the, all the information that I’ve got, all the good decision making and bad decision making that I’ve done, that informs my efforts?

How can I use those to, to, to maximize my opportunities in the future?

Steve: What is it that you, um, learn or pick up over your years just working in vc that that accumulates? You said good decisions, bad decisions, and how does it accumulate and how do you recognize it and how does that. How does that show up in future in the future?

Kyle: Well, it’s, it’s immediately evident, experienced venture capitalists. can immediately detect their mastery from the quality of the companies and the management teams that they field. You can just see, I, I can see when I, I read a, you know, a funding announcement from someone I respect about a new company that they put money into and what’s going on there. And I look at the list of the individuals involved, and this is mostly in the biotech business where people tend to be more experienced than they are in tech, um, in their careers. can, I can see the targets, I can see the, the academic history of the thing. I can read the papers, I can see who the venture capitalists are.

I can see the management team. It’s like that, that’s a pro effort. No guarantee of success, but with a little luck and timing and wind at their back, that’s gonna be a, a very successful company.

Steve: We talked about the analogy of, you know, a powder day to, you know, success in business you just brought it up again, like the wind at the back. Wind. How do you know when you’re too early?

Kyle: Well being early in the venture business is a common mistake,

Steve: Hmm.

Kyle: it’s exactly the same as being wrong. So result is the same. So.

Steve: So, so you know how you’re wrong in retrospect, right? Once it’s gone up in flames. Okay. No questions about that, but, but how do you know when you’re too early? Like.

Kyle: doesn’t work. There’s no product market fit, you know, or that you can’t make the drug, the drug works, but you can’t make it. Or, you know, no one’s willing to, even, even, I’ve had the experience of having developed a drug company with experience management. The drug works doesn’t understand how a drug like that can work and turns it down, you know, says no. ’cause we were too early. No one had a genetic medicine for heart disease before arca, 20 years later, they’re all genetic medicines. You know? So there’s lots of ways, there’s a million ways to fail a venture capitalist. And it’s only in retrospect that you, that you have, you know, that you have the, the, that you gain the wisdom and the perspective. try to do better the next time. And it’s the same, I think, in mountain guiding. You know, you want to try to cover the same terrain over and over and over again to become expert at it, to avoid those mistakes. And that’s really the value you bring to a client is, is knowing how not to fail.

Steve: I wanna talk a, I wanna hear from you a little bit about, you know, and a la carte, your choice. you, you take me through a story of a, of a company? You talk about a number, a couple of them in, in your book, but can you take me through sort of a lifecycle story? It could be a success or, you know, like the one I mentioned in the intro, or it could be one I don’t know about. And just talk to me, talk me through how that went down and how that works.

Kyle: Hmm.

Steve: Particularly as like what you were just talking about, that, that putting together a, board, uh, the management, the, the idea, the academic backing. I wanna understand that’s an alchemy of sorts. Like go, what’s in that potion in a, in a real world example.

Kyle: Well, let me, me contrast two of them that are in the book, because it’s often the case that, that, you know, you, you’re in our, in, in our model at Boulder Ventures, it’s always about the serial entrepreneur. We’re, we’re focused on our relationship with that entrepreneur and what we can do together. It’s not as if we pick a fast growing market and we assemble the team and point ’em with our host full of money and try to, and try to light it on fire.

Steve: so you said serial entrepreneurs, so you don’t fund people that it’s their first company.

Kyle: No,

Steve: Okay.

Kyle: we’re fortunate because we have this long history with Merck. It’s at Colorado Venture Management, the predecessor fund, and now 30 years with Boulder Ventures. We have this large and devoted following in Boulder of, of, of entrepreneurs who’ve come up being mentored by other entrepreneurs through these successful companies.

And we have this, this group that we can depend on to, to, to develop new ideas and who are subject matter experts. a big advantage for a venture capital fund.

Steve: Yeah,

makes sense.

Kyle: we are not, you know, you, you know what Y Combinator is

Steve: Yeah,

sure.

Kyle: Valley. We’re not Y Combinator. You know, we’re not, we’re not investing in Nubes.

There are no nubes around here. They’re all very experienced entrepreneurs and, and we have. Exceptional confidence in our authentic relationship with those individuals and their capabilities. And so that takes a lot of the management risk off the table.

Steve: Mm-hmm.

Kyle: Okay. what we’re, we’re, we’re focused on are, are, you know, big markets in the future that we see coming can we point entrepreneur and our money and our capabilities and this team at that problem because the product itself is gonna change and, maneuver over time.

It’s not, not about funding a product for us, it’s about, you know, a, a large market opportunity and an experience, CEO and, and, and the people around him, they, they always come with a team, that can, that can together make something really interesting there.

Steve: Hmm. So in, you know, small business people talk about the pipeline of, from the people discovering you to the people who are buying from you. And it sounds like you’ve sort of built your, your in a way as a company that’s going to become successful in the ways you described. you’ve built this pipeline because you have these people just cycling, like, do this company for 10 years and they’re gonna go do another one with another person, and in your pipeline and they’re just coming through.

Kyle: One of the great advantages to doing this in Boulder is that none of the people we invest in here, Steve, none of these entrepreneurs, uh, have any ambition to sell their company and go somewhere else. This isn’t the end for them. They live here. This is their lives. They, we’ve raised our families here.

We’re committed to this community. all, we all are at some level elite human athletes. and that’s a big part of why we’re here. we’re all skiing and climbing and biking and running together. So, so, you know, unlike Silicon Valley where, you know, a lot of the time the goal is make a lot of money on my deal and retire to Jackson, spend the rest of my life having fun. That’s a different mentality. I’m not gonna, I’m not gonna criticize that, but it’s a different mentality than the mentality in Boulder where we’re committed to each other over our lives to work on the future and we’re not going anywhere. And if we’re successful in the future, great. And if we’re not, we’re still gonna do lots of climbing and skiing.

Steve: You know, I think that you picked up an interesting point where the, I’m gonna sell my company and retire somewhere suits my fancy, that’s more of like a, a gambler mentality. Like, I gotta, I gotta, I’m just going for the big payout. Like, and that’s, that’s the goal. And then to do nothing afterwards.

And what you are talking about when you keep using this word mastery as well, which ties into this where you’re talking about just iterating. Just doing reps and you’re not going anywhere ’cause it doesn’t get any better than where you are now and you love what you’re doing and you’re continually getting better at it.

This is one of the things I love about my little small business is ’cause I’m, I’m so, I have so much growth and I can continue to get better at this for so long. Whereas I can’t, my, my window to get better as an athlete ended already a long time ago, 15 years ago. Right. And that’s just age. But you guys are just committed to the process and are just there.

And that’s fundamentally different thing than the, I don’t, maybe don’t like this term gambler mentality, that’s not the right term. But I’m gonna win big and cash out and go like sail around in my yacht or whatever. You are like, yeah, you’re just gonna stay in Boulder. You’re gonna go climbing with your friends, you’re gonna, you know, go out for dinner and downtown and some new great restaurant that just opened up and. You’re gonna wake up and do it again tomorrow and the next week and the week after that. That’s what I love. Like, that’s like when you talk to people like yourself and, and you know, a lot of the people I’ve interviewed in this series, exactly how they’re wired. And I find maybe I need to find someone who’s wired the other way and try to understand that perspective.

Kyle: I don’t think it would be very interesting. You know,

Steve: could,

Kyle: goes into that office in, in, in, uh, Bentonville, Arkansas every day

Steve: yeah.

Kyle: tries to get better at

Steve: Yeah,

Kyle: business in the world.

Steve: yeah.

Kyle: interesting problem,

Steve: Yeah. Super interesting.

Kyle: guy,

Steve: Yeah,

Kyle: think about things at that scale and how to be better at ’em, you

Steve: super fascinating. Yeah. yeah. so much room for error and, and such big consequences if you get, you know, for so many people like the responsibility.

Kyle: It’s mind blowing what the, the, resources and the risks that, that guy, that guy deals with on a daily basis.

Steve: Incredible. Right.

Kyle: I was a great conversation. I, I was, I was enthralled by it.

Steve: well, thank you. I, he’s a great conversationalist and a super interesting guy.

Kyle: And a great owner of the Broncos too, by the way. So, you know, clearly that guy has some capabilities outside of just the, the, the boardroom that are, that are relevant.

Steve: Well, we’re recording October 13th and there was a really good football game, like, uh, on, I think it was Sunday night or just, just recently, where they, they they pulled it out.

Kyle: they beat, they pulled it out and beat and bone X looks like a great new quarterback, so.

Steve: Yeah, that was in, that was incredible. I was, I was watching that and I haven’t watched a football game in years, and then I heard that was on, I was like, oh, I wonder, I’m, you know, I just had talked to Greg and Greg was in my mind, so I tuned in and man, what a finish. Anyway. So one thing I heard is that early on you were able to get in touch with these, ’cause it was such a small world and you’re not intimidated by people and you’re just able to call people up and they’re coming out to Colorado, they’re going skiing or taking ’em up to veil. Oh, by the way, I have this, uh, powder skiing operation. Uh, and uh, I could take you out the veil backcountry. We can ski have some of the best turns of your life. that’s ostensibly not a bus, not about business, but it’s absolutely about a relationship. I mean, we’ve shared some great powder days and we know what that, and, and not just with each other, but with other people.

And we know what that bond is like at the end of the day, after everybody’s just been on cloud, literally on cloud nine for the whole day. How does that, how does that, I find that very brave, Kyle. I gotta say like, I find that very personally, I find that very hard to do. To, like, to do. I like, it’s, there’s a lot of bridges in between that first phone call and that powder day.

There’s a lot of little connections and points of contact and, ’cause I, I know this about you and it’s certainly true about me. I don’t go powder skiing with just anybody you know. And, and, and I, it’s somebody I know, somebody I trust, somebody I care about somebody who could dig me out if the, if the snow starts, you know, slides and ends up on top of me, there’s a lot of qualifications that have to come in, into be a lot of boxes that have to get checked before I go powder skiing with somebody. I find that very brave and very impressive that you can pull that off. And me how, like, did you, did you that whole path from the beginning or did it organically unfold? You’re like.

Kyle: Yeah, I brought a guiding mentality to it and, and, and throughout the venture capital, everybody in the venture business, everybody in the venture business knows that I’m a mountain guy because they’ve all come skiing with me in Vail in the wintertime. And that’s a place where venture capitalists come to ski in the winter and, and if they go to Zuma or they go to Shamini, they call me and say, who should I ski with?

And I connect them with, know, a mountain guide in those places who are also lifetime friends of mine. was always the venture capital guy who was a mountain guide, and so

Steve: Okay.

Kyle: would go skiing with me. So I leveraged that expertise and that reputation to foster these authentic relationships with entrepreneurs and venture capitalists and investors in my fund. Together in a setting. I mean the, the Snowcat Operation Vail Powder Guides on Vail Pass that Ben and Jenna Bartow’s own that. That’s the, that’s the ideal setting for those kind of conversations.

Steve: Yeah.

Kyle: this will be our 20th year of operations up there on Vail Pass this year. proud of the, those guys, Ben and Jenna, and the, the business they’ve built, and we’ve used it effectively in our business to develop these authentic relationships.

At Boulder Ventures. You can see it in the book. There’s lots of pictures of

Steve: Yeah, of course.

Kyle: capitalists and entrepreneurs and investors all, all enjoying powder skiing. With, with left off on Bill Pass.

Steve: Talk to me about the bridge between that relationship that is forged there at Voil Path and the relationship that is forged when you call them and say, Hey, I’ve got a, I’m putting together a deal that you might be interested in. What’s the connection? Or is it just seamless?

Kyle: Once you’ve developed those authentic relationships over a long period of time progression with risk that that have resulted in, you know, something, more than just a casual business professional relationship. These are, these are, these are authentic relationships, which I describe in my blog as a, as, as, as a special, your goal as an entrepreneur, your goal as a venture capitalist, your goal as a mountain guide is to, is to foster those and to collect those relationships because you, you rely on them in your business and you rely on them in your guided, um, and, and that’s what is meaningful in life to me.

That’s where I get joy in my. in, in my work. And, and that’s, that’s what you rely on to be successful in both your guiding and in and in business.

Steve: Okay, so let me ask it this way. Have you been powder skiing with somebody and then after that been like, I’m never working with that guy in the VC world. Why? What happened?

Kyle: They won’t be, you know, they’re guidable You’ve experienced this, haven’t you?

Steve: Sure.

Oh yeah. Yeah.

Kyle: meet these people are just guidable, you know, carefully, I’m gonna, I’m gonna ski the left line. Don’t go right of my, don’t go left of my track. That’s dangerous terrain. I’m the left fence here I’m gonna stop down here at the bottom.

And the guy just, off all over the place. Right?

Steve: Yeah.

Kyle: like, what did, what did you hear me say? what he heard me say was, WW wa w wa powder. guy’s guidable. Well, the same thing is true in business. meet. that are guidable and you know, that’s fine. That’s somebody else’s deal to do, not me.

Steve: Okay. What about the middle case? Have you done deals with people and then, or, or worked in companies with people, I should say, and then on the second or third or fifth or 10th year or second or third iteration, they, you find out about a side of them that makes them, as you say, guidable or unworkable. And, and were there warning signs

Kyle: It is a frequent experience that you’re disappointed over time in, in your authentic relationship with somebody. That’s, that’s common. also in, in both guiding and in in business, and it’s often also. Experience that, that the capability of the entrepreneur in a startup is not matched by his capability.

Once a thing has achieved product market fit and the flywheel’s going and it’s taken off, and the guy from zero to $10 million in revenue is often not the same guy who takes it from 10 to a hundred, So you just have to be attuned as a venture capitalist, as a mountain guy, to what are, what are the strengths and weaknesses of your, of your authentic relationship and, you know,

Steve: I.

Kyle: take it and how do you communicate when you know the individuals reach his highest level, we can just stay there and be happy. But if you push forward, you’re gonna, you’re gonna put yourself at risk.

Steve: Hmm.
Kyle: my judgment. I could be wrong.

Steve: You know, one of the things that I think is interesting and, uh, maybe I, I have a very simplistic view of how the VC world works. I’ve never been involved in it in any way, shape, or form. But you raise a fund, you have X dollars, and you go to invest those dollars and, you know, you invest, say, in 10 companies, and I don’t know, two of them do well and eight of them evaporate, those two have to cover the returns of, of the other, uh, eight that went away.

Is that,

Kyle: A sophisticated view of the venture capital business.

Steve: yeah. Real sophisticated. So, so this, so as you said, like this disappointment happens. and you, despite all the reps that you’ve done, despite this incredible pipeline that you’ve built, and these, these long-term relationships you’ve established with countless individuals and you’ve skied with them and you’ve closed deals with them, and you’ve run companies and you’ve boards and you’ve sat on their boards and, and you still are sometimes disappointed.

How does that happen?

Kyle: It’s astonishing how wrong I can be about the future.

Steve: And what are you wrong about? I mean, okay, the future, but what is, what is the detail? What, what’s what wrong about what wrong about whether it was too early or too late, or the right time?

Kyle: Was too early or too late, was it too competitive And there were many other people after the same thing. Were I just, I was wrong about our luck we were unlucky. The thing we tried to do, I was wrong about the individual. And he was at a stage in his life that, that that wasn’t gonna be as prosperous and and productive for him as as it was before. Um, it can, how can I be so wrong about the future? And I am frequently wrong about the future because I’m living in the future. I’m trying to visualize what the future looks like and I have a, a good map of that. I’ve been at it a long time, so I have a, you know, I’ve been right more than I’ve been wrong.

So I have a, a clear view of what I think the future looks like. And the same thing’s true in, in, in ski. I’ve, I’ve seen this powder day on Vail Pass a hundred times and it looks fantastic, Benny. We’re going, this is gonna be unbelievable. And we’re going out to the top of machine gun first when we get out there and it’s bulletproof. Come on. How did that happen? Well, there’s some random wind came up and buffed out the top and blew it all away. I’ve seen that, but that happens, right? You’ve been in that situation many times before too, where you absolutely had it dialed and knew what was coming and then complete, unexpected. I was wrong about the future.

Steve: Do we as humans? And maybe there’s different levels to this, and you’ve talked about the entrepreneurial one, the vc. Are we by nature too optimistic?

Kyle: No. It’s a feature of entrepreneurs and, and climbers that they’re optimistic. You can’t be a pessimist and be a, a, um, you know, be a doubter either in yourself or in the objective and, and, and be successful as an entrepreneur or as a climber. You are by nature optimist.

Steve: Are we,

Kyle: win. The optimists win.

That’s one of the lessons of venture capitals. The the optimists win. They may not win today. They may not win tomorrow, but they will win in the future.

Steve: why?

Kyle: Doomers, the Doomers are always wrong because human nature is is infinitely Human elite. Human capital is infinitely scalable, never bet against elite human capital. America is the center of the world of elite human capital. Never bet against America because that’s where all the smart people who wanna live in the future come. And if they want to come climb and ski, they’re coming to Boulder, Colorado,

Steve: And if they’re in biotech, they’re going to ski with Kyle Loff.

Kyle: to.

Steve: No, I, I agree with everything you say and I think it’s also everyone else in the world is sort of puzzling trying to figure out what is, like what I talked, asked you earlier, whether it was Florence and the Renaissance or or Silicon Valley today, like. Or, or Boulder. What are these, what are these magic ingredients? How much of the magic ingredients, how, how, what portion of the magic ingredients? I know there are probably many and probably some we don’t understand or know about, but how much of that is actually the availability of capital, venture capital specifically, that you can, if you have a good idea, in most cases you can find someone to, and you, and you have a plan and say, Hey, I need $10 million get this off the ground and I think it’s gonna work and we’re gonna, you know, and have a projection and you have a good plan that, that somebody will write you a check for $10 million or at least eight or what, you know, maybe I’m oversimplifying, but how much of it is that?

Kyle: Well, there’s no question that the capital markets in America from the very small, you know, angel network and the local town that funds the guy with his idea to the, the public stock markets and debt markets that can aggregate hundreds of billions of dollars instantly to point at. It’s, there’s no question that that’s an important feature, it’s not, it is not where the causal era starts.

You, it is, you know, we’re not a great center of entrepreneurship in Boulder because, because there’s tons of money here pointing at these entrepreneurs. We’re a great center of venture capital in Boulder because of the elite human capital that draws the money in and, and, and makes it, and points it at the future and makes it successful.

Steve: Kyle Fko of 1975 knows if Kyle Lefkoff of 1975 were to know that Kyle Fko of 2025 right now today knows. What would he do different?

Kyle: I don’t think I would. I, I, I don’t think I would’ve. I, I think I had it. I think I got it I, the first summer I came to Boulder that I, I’ve tried to describe to you how profound that impact was. Me coming from the place I came from.

Steve: Mm hmm. Yeah.

Kyle: I, I, I think I got, I, I, it had such a dramatic impact on my psyche and on my, on my desire and a place to point my energy for business and for climbing.

You know, it.

Steve: and that place you came from is Atlanta, Georgia. It’s Judaism, it’s, you know, you’re in Vassar, uh, upstate New York, the Gunks, university of Chicago. I mean, and then of course the road, all the places the road took you along the way and, and, and, and that all brought you to that point. You know, I think that this is one of the. For younger people and even for older people, especially those that are ambitious are, are looking for that like sign, you know, that, that, that confirmation and to be able to look back, at their lives, you know, however, ready 50 years later and, and be like, yep, that was the right, right thing. So

Kyle: I don’t know if that’s a common human experience, but for me it was.

Steve: hmm

Kyle: me, it was the epiphany was, this was my place where matters. And, and I could develop both of these sets, my human capital and my human athletic potential in the same place, and, and express that in both, both arenas.

Steve: And be allowed to, or be even encouraged to express that intensity, that curiosity, that, that, that who you are, all of who you are. So that’s, that’s pretty, that’s pretty. Pretty amazing. Um, well, I’m, I, for 1:00 AM super glad that, that you were able to find that Kyle, I think you’re a pretty amazing guy and you’ve been an incredible friend and mentor to me.

I don’t know if you realize how much of an impact you’ve had on, not just myself, but a lot of people in the guiding and climbing community who have come into contact with you and you’ve, you know, you’ve brought this other perspective, this other you know, of, of, of your professional career and shared it with us in the levels of the American Mountain Guide Association or the Airy, or in all these ways.

And I found it fascinating and I’ve learned so much from you. I’ve just from, like you said, watching you operate and take people climbing and poor people. Really good glasses of wine and all the other, other things that, uh, that you’ve, you’ve done. One final question. What is the legacy of Kyle Lefkoff?

Like, you’ve written this book, as you said, it’s like kind of the legacy of Boulder Ventures in a way. Maybe it’s even the, blueprint as you see it, you guys are in, I think, your eighth fund now.

Kyle: Sure we’re, we’re going to raise the ninth fund this year.

Steve: You’re, oh, okay. So, yeah, I mean, congratulations. It’s huge. What’s, how do you wanna be remembered?

Kyle: I think that, I think now I’m, it’s a good question, what I’m thinking about for obvious reasons at this stage in my

Steve: Yeah.

Kyle: but, um, I think I wanna be remembered for building bridges that, that, that was really where all this, all this effort and all this energy and all this. Training and iteration led me to building bridges between, between clients and mountain guides, and building bridges between guides in their career and their ability to become successful professionals. Building bridges between entrepreneurs and investors and acting is the essential glue that that creates the opportunity for both. we just this week, uh, built a bridge in El Dorado Canyon across to the base of the West Ridge, and, um,

Steve: Oh wow.

Kyle: Thursday. Have you ever walked across to the base of the West Ridge?

Steve: Yeah,

yeah, yeah. Sure.

Kyle: we built a bridge to

Steve: Amazing.

Kyle: Bridge. I’m really proud of those and that, and those, those are the hardest things to do,

Steve: Yeah.
Kyle: those bridges,

Steve: Yeah,

Kyle: but they’re also the most rewarding. They take a lot of time and effort and experience. Um,

Steve: they do

Kyle: there’s always doubters and naysayers who don’t want the bridge to be built.

Steve: a hundred percent.

Kyle: those obstacles and be single-mindedly focused on the objective with a group of people. when you succeed at it, the results are, the results are really satisfying.

Steve: Um, I love your perspective on the optimist always winning. I, I, I so hope you’re right in every, every possible way. So thank you for this incredible conversation. Kyle, you’ve shared so much with the community. I just, so much gratitude. So thank you for coming on tonight and thank you for doing this one podcast.

I, I had to twist your arm just a little bit. Maybe your wife was involved. Maybe I have to.

Kyle: Steve, I’ve never done this before and I’ll never do it again, so I’m really grateful to you for, for having made that a, a painless exercise. I really enjoyed it.

Steve: Well, I hope you do it again, so I’m sure I’m not alone in that. So thanks you, Kyle, for your incredible contributions and we will be in touch.

Kyle: Thank you.

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