← Going Big! with Kevin Gentry
Going Big! with Kevin Gentry
Going Big with Jeff Rosenthal: No Small Plans, No Limits, and the Power of Bold Vision
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Sponsor Announcer
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Country Farm and Garden Announcer
Plantas plantas y mas plantas and country, farm and garden A key mismo in Yakima and La Venida Washington des de los mimientos mas picantes del mundo asta las flores mas hermosas lot tenemos todo calatisado, jalapeno Roma y super Chile en existencia todo los dias un paquete de cuatro vegetales cuestas solo tres doles conventin, nueve Santabos, vena, country farm and garden para todo tus vegetales, tomates, seboyas, pimientos y pepinos siempre in existencia and country farm and garden and Abenida watchen and Yakima.
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Jeff Rosenthal
My generation. Our problem was hubris. I'm a genius. My idea is amazing. Elon needs to hear about this. Like call Jeff Bezos. Get him on the phone. You know, he needs to know about my, you know, my new subscription shoe company. It's like who cares, man? But. But we all had way more hubris than we should. I'd say the problem facing today's generation, as you mentioned, you know, there's a great book called the Ancient Anxious Generation by Jonathan Haidt. A lot of it is imposter syndrome and anxiety. Right? I think that just know that the hidden truth of the world is that this is all things that were made by people and could be remade just as easily. And the there are the 0.01% of exceptional freak show geniuses like, I'm sure five of my brains fit in George Church's brain or Elon's brain or Peter Thiel's brain, whatever, right? But the vast majority of people who have built all the things that you touch and use are a couple of IQ points away from you. It's not like they're or the. And plenty of people who are not, you know, brainiacs have been the ones that have executed and operated and made these things truly happen all around the world.
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Kevin Gentry
Welcome to the Going Big Podcast. I'm your host, Kevin Gentry, and this is the place where we celebrate bold moves and big ideas. Each week I sit down with inspiring leaders, entrepreneurs, and change makers who are making a significant impact in their careers and in their communities. Whether you're looking to level up your leadership, pursue your passion, or just get inspired to take your next big leap, this is where those stories come to life. Now, if you're listening on iTunes, YouTube, or anywhere else you tune into podcasts, be sure to hit that subscribe button so you'll never miss an episode. Now let's dive in to what it means to truly go big. Well, ladies and gentlemen, welcome. I am really pleased to have Jeff Rosenthal as my guest today on the Going Big podcast because he really exemplifies going big, and you'll see that very quickly in this conversation. Jeff Rosenthal, together with three others in 2008 with no event experience, took on building a global events company that has become renowned for its breadth and magnitude. It's called Summit. You may be familiar with it. It is a community where people exchange big thinkers, creators come together, exchange ideas and insights about the world and the future. It's amazing. So that in and of itself is significant. Then he and his buddies wrote this phenomenal book, make no Small Plans, which in and of itself has become really a guidebook for people who are looking for visionary approaches to tackling new innovations. It's been a big inspiration for me personally, has been for the Going Big podcast and for my company, 10X Strategies. That's why I've wanted to have Jeff on this episode for a while. And then after having done this, Jeff, with his friends, bought and built Powder Mountain, which is the biggest ski community in the United States. But it's more than just a mountain. It also was a community of people coming together to learn and discuss and think about problems in a different way. Really building community. That's something we want to talk about. And now, recently, he just started an investment firm Civ. It's his newest venture, which is focused on investing at the intersection of technology and critical industries. We've got a lot to talk about, Jeff. I'm really pleased to have you here. But first, out of the blocks. What made you all decide to call this book make no Small Plans? And what does that title mean to you personally?
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Jeff Rosenthal
Wonderful, Kevin. Thank you for having me on the podcast. Great to see you. Make no Small Plans is actually a misquote of the wonderful Daniel Burnham quote, make no little plans. And what's great about misquoting people is then you are the original and, you know, so. So make no small plans. The first time we used that line was the first time we chartered an ocean liner back in 2011 for one of the events we hosted called Summit at Sea. We always would be like, okay, what's a big enough idea to actually excite people who are much more senior, experienced, successful, and interesting than us? And we'd say, like, let's rent out the JW Marriott. No, not. That's not worth it. Like, everybody's busy until they're dead, particularly at a certain level, you know, and we would go through this process of, like, what's crazy enough, but actually achievable. And so we were like, you know, could you charter an ocean liner? I think we were 25 years old, maybe 26. And when everyone showed up in Miami for that event and you were on the highway going out to the. To where all the boats were, we had unfurled this giant, you know, I think it was 100 by 100 foot flag, basically, that said, make no small plans on the side of the boat. And for us, yeah, I just always felt like, you know, you live one time, you want to get the best people around you. You have to be focused on things where your reach exceeds your grasp. Like, otherwise, it's just not going to create the excitement and the enthusiasm that's required to recruit, you know, a community around you to do things that haven't been done before.
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Kevin Gentry
Well, thanks for the reference to Daniel Burnham. That quote has always been an inspiration to me. As folks know, he was the, you know, tremendous architect of the 19th century, really, with rebuilding the city of Chicago. But that quote, make no little plans. They have no ability to stir men's souls and otherwise will fail, or something along those lines. It's there on a plaque if you walk into Union station in Washington, D.C. so it's great that you captured the essence of that. And there's so much, again, to talk about this, Jeff, you and I met a couple years ago, different conferences. I remember conversations with you, and I didn't even know really what you were doing until after one of those conversations. I stumbled upon the book, and it was the title that caught my attention. And I started looking through it and saw that you were one of the co authors, which obviously caught my attention all the more so. I gotta say that the idea of stepping out boldly beyond your wildest dreams has a tremendous ability to capture people's imagination, but it's risky and most people are unwilling to take those risks. And you all went big. So early on, if you would, if you could walk us through a little bit about how this came together. My understanding is you were a college student in Washington, dc. You were known for being able to put together some parties on campus, but you were a key contributor in this group, the four of you all to go big. Just tell us a little bit about the early days.
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Jeff Rosenthal
Yeah, absolutely. So in college, I played soccer at American University. I threw parties. I worked in Congress. I worked for the Rules Committee. I was professional staff and floor staff for the Rules Committee and the House of Representatives. I had little clothing companies and startups, and I was just an entrepreneur before I really even knew what the word meant, honestly. My partner in my party business was a guy named Brett Leaf who went to gw and he and I, along with our other co founders, started Summit together after school. I'd moved to New York, had a couple of jobs, started a business, and that business started to scale. And when you're 22, 23, and things start going well, everything falls apart because you have no experience, you don't know what you're doing. And I was like, man, we were all like, we really need to build a peer group. And so, you know, we cold called and Facebook message different entrepreneurs that we had read about. We got 19 people to go skiing with us in park city, Utah, in 2008. Sam Altman was on that first trip. The founders of CollegeHumor, founders of Thrillist, a couple of other really amazing people. Six months later, we threw our second event in Mexico. And it had the founders of Facebook and YouTube and Uber before Uber, but also Change.org and DonorsChoose and Charity Water. And so those first two events we literally put on our credit cards. And our third event was at the White House a month after the Obama administration took office. So we went from this little tiny nugget of an idea to, you know, hosting events on behalf of the administration in like 300 days. Um, and so it was a Very exponential curve. Um, and funny enough at that event, Tony Hsieh, who actually has since passed away, but he was the founder of Zappos, he wrote a great book called Delivering Happiness. He pulled us aside after that event and he said, hey guys, are there people here who, if they didn't have their personal and professional success, you would still, you wouldn't have them to your parents house for dinner? And we were like, yeah, of course there's some people here that like, we don't want to have to our parents house for dinner. But you know, like, that's not what we were tasked with. We were told to bring the, you know, best and brightest founders in America. And he's like, yeah, well they can't come anymore. He goes, when you're building a community, culture is the most important thing. And if people don't fit that culture, you're ultimately not going to go anywhere. And until that moment, we didn't realize we were building a community. And that night we literally didn't sleep and just kept thinking about that. And we came up with our criteria. One, are these people innovators in their field, regardless of the discipline? And two, are they just kind, open minded people that regardless of their professional success, we would be, you know, thrilled to introduce them to our folks. And then, you know, our conferences got more and more sophisticated and you know, we hosted incredible people. We started chartering ocean liners, we started bringing in music and art and food. And now that's pretty, you know, standard. I think at the time, it hadn't really been done before, leading to in 2013, at 28 years old, buying the largest ski resort in the United States. Very much inspired by this idea of, you know, having foundation, having roots, having a physical home for this idea or this community that otherwise would be ephemeral.
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Kevin Gentry
Well, okay, so I think this begs a number of questions. Cause people who are listening, it's like, wait, that is a lot of stuff that happened very quickly. And so how do you go from your early 20s just having this kind of concept, but you truly want to go big because you'll, you'll. Even if you just had 19 people at the first meeting, you had some real players. And, and maybe they weren't as big of players then as they are now, but they certainly weren't a track. I mean, how did just some of this happen initially, conceptually, did you say, hey, look, we want to go big. And I do want to come back to the question about building a community through having the right culture. But before we get there did you initially say, let's go big? How do you, how do you even begin to establish that vision?
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Jeff Rosenthal
Well, I don't think we didn't have a strategy. This was, we would say gardening, not architecture. You know, it wasn't as though we had a strategic plan that we executed on against that ultimately led to us buying Powder Mountain. This was very much like we would reevaluate what we should do next after every event that we would host. It was a revolution, not an evolution. It changed the trajectory almost completely based on the people who we got to come to these experiences and the quality of experience that they had. And that would lead to their willingness to build and partner with us on a go forward basis. So, no, we weren't like, hey, let's go big and that. But I do think it was part of our culture from the very beginning. You know, like, we had ambition certainly, but we were having so much fun. You know, there's this great enthusiasm. The root of enthusiasm in theos, in Latin means with God. And if it's fun for me and it's work for you, I'm gonna run circles around you and vice versa. So, you know, I think that foundationally what enabled us going bid was big was partnership. You know, we would sit around the phone cold calling people more or less, or like, you know, getting on the phone with these folks who didn't really want to spend time with us and ultimately would leave them convinced that they should actually spend money to come to our gatherings. And that really came from sitting with my co founders and us hearing each other articulate, you know, our vision for what this thing would become. We also all lived together, and then we did that for almost five years. Just not just the founders, but the first 20 employees. So it was four and then it was six, and then it was 10, and then it was 20. We would move the whole company to a new city or place every like, you know, four to six weeks, and then once that scale, four to six months leading until we ultimately moved to Utah and bought Powder Mountain. But that meant that like, you know, at lunch, we were ideating at the gym, we were talking about things that we might be able to do. It was just this constant creative process. And so I think that was the conditions that led to us having the ability to shoot for the stars. And when you do that, you ultimately land on the moon. You know, you might not achieve like all the crazy things that you're attempting, but you're certainly going to get somewhere special.
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Kevin Gentry
All right, well, two questions related to that talk a little bit more about partnership. There were four of you. You know, partnership is often defined in this way about shared values and shared objectives. But what. What was necessary in terms of synergy or common principles or foundation in order for you all to work together so productively?
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Jeff Rosenthal
I think first and foremost is character and integrity. You know, friendship is fragile, and my opinion along the family, the most special thing that you're going to experience in Life, right? There's 9 billion people on the planet. There's, if you're lucky, a few that deeply care about you. And I think that foundationally, if you do not share character and integrity and values with the people you're building with, you are doomed. Every single time I've ever worked with anybody in my career where I've been like, well, you know, I don't know that I align on these things, but think about all the value they'll create for us. It never works out that that's the. That's the first and most important thing. There's no greater building block than trust. And, you know, this. This is, you know, built in drops and lost in buckets. And so, you know, I was very lucky to get to partner with guys that, you know, I was very aligned with. In terms of vision, it's interesting. I think now I'm 40. I've been in business for 20 years. We'll run a process with stakeholders where we'll say, okay, what is your vision? Not the company vision, your vision for what we're going to do. And then we'll go to the next person, say, all right, great. What's your vision? And then how do we align those different perspectives and overlay them so we ultimately are all very clear on where we're going as a team? I think that we had the luxury of doing that just in dialogue. And because we were so young, we were 23 when we started this. We were just sharpening each other like swords. I needed my partners to evolve to a greater place today than they were at yesterday. If you were only as good as you were yesterday, that's not good enough. And so all of us held each other to a really high standard. I grew up playing team sports, and as a competitive athlete growing up, and I think that gave me this, you know, addiction to championship ball clubs. Like, I don't know of a better feeling than, like, that feeling of coming together with a group of people and achieving something that was once beyond your reach. And so there was always a culture of exceptionalism and an expectation of performance. And so while we were all friends and we all worked together. You know, people say, don't work with your friends. I've only worked with my friends. But there is a responsibility that you take in those situations to deliver and to step up and to be there. Certainly there'll be times where you're not at your best or that you need a break. And that's where it's imperative that you have partners that can carry that weight on your behalf and vice versa when they can't perform. But yeah, those were, I think, many of the things that really enabled us early on.
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Kevin Gentry
Wow, what was that line again? Reputation is gained in drops and lost in buckets.
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Jeff Rosenthal
Yeah, you build it in drops and you lose it in buckets.
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Kevin Gentry
Well said. All right, well, related to that, several episodes ago of the Going Big podcast, I had Will Guidera, who had the vision for building 11 Madison park into the greatest restaurant in the world, this concept of unreasonable hospitality. And he often goes back to a quote from his father that said, if you knew you couldn't fail, what would you do? How bound were you all by any concept of risk or failure? Or were you at a st. I mean, yes, you put everything on your credit card. I mean, but, but, but tell us a little bit more about the sort of risk taking attitude.
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Jeff Rosenthal
Our reaction to imposter syndrome was to mess with people. Um, and so instead of being like, oh, man, I don't know if I can be in this room. Everybody's so successful, they're so talented, like, what do I. How do I deserve to be here? They're gonna know that I'm, you know, a novice. And that. That sort of can be really crippling. Right. It makes it very, very difficult. Our motion when we would feel that was to just literally mess with those people. And so we would just talk shit and they would have fun. And so it wasn't about, you know, like, the professional relationship first in those. In those interactions. It was like, you know, at a minimum, this is going to be their favorite interaction of the week. Right. Like, if we can achieve that, then there's likely a door that's open for us, you know, on an ongoing basis. And so, you know, I think that that was extremely empowering in terms of, like, if you knew you couldn't fail, like, we didn't think about failure at all. We didn't have anything. Why would we care? Like, we had no reputation, we had no money. You know, we had thrown a couple of cool events. Who cares? You know, like, let's try. And in the worst case, it's not like the people that love us would love us any more or less based on the success or failure of our venture. And I think that enabled us to really go for it. None of us come from mega wealthy families or anything, but we certainly did grow up solidly middle class and have loving parents. And that puts us damn near the end zone in the scale of life. And so I think we really did feel like we had the capacity to do something great, which is totally unmoored from reality. Like, none of us were target students. None of us went to Ivy League schools. None of us were recruited to Goldman Sachs. Like, we were pretty non target guys. And yet we unreasonably thought that we too could build something special. And yeah, I mean, I think that.
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Country Farm and Garden Announcer
Plantas, plantas y mas plantas in Country Farm and Garden, Aqui miso and Yakima in la venida, Washington des delos pimientos must be cantes del mundo as the las flores mace hermosas lot tenemos todo caratisado jalapeno Roma y super chile en existencia todo los dias un paquete de cuatro vejetales cues solo tres doles conventin hueves and tabos vena Country Farm and Garden para todo tus vegetales tomates, cebollas, pimientos y pepinos siempre en existencia and Country Farm and Garden and Avenida Watson and Yakima.
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Jeff Rosenthal
There's a way to perceive failure that's more productive, which is just. It's all a learning opportunity. It's all on the path to getting where you want to go. If you are doing something new, you're definitely wrong. The question is just how far are you from the right answer? Right. So accepting that is key. There's a great book that. The kind of like the graphic novel version of the samurai philosophy. It's called the Hagakure. It's this amazing. It's. I love this book, but one of the things that they talk about is being a shammer. I mean, it means that you're always in shame. You're always in shame because you're always trying to improve beyond the point that you're at today. And therefore you are in a constant state of failure. Yeah. So I think that. That, you know, from a very early, early age was our. Our perspective and allowed us to go for it.
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Kevin Gentry
All right, well, just to give us some perspective, in those early days of Summit, was there a particularly scary moment when you all were like, oh, my Gosh, what have we gotten ourselves into? Or is this gonna work or what?
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Jeff Rosenthal
It started working almost immediately. So there was never like, is this gonna work? Like, it was a bright idea for the right time. Like, you know, these worlds were all wildly disconnected. Nobody's businesses were really relevant to each other's. Right. And so today that's completely shifted, and everything really is connected. But you rewind the clock 20 years, it was a very different business ecosystem. So I think it was the right idea at the right time. The momentum was always there. We would call it Kevin Final Fridays. Have you ever heard the term Final Fridays?
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Kevin Gentry
No, no, please, go ahead.
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Jeff Rosenthal
Final Friday is the last day you can wire the money because the bank is coming.
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Kevin Gentry
Right? Right.
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Jeff Rosenthal
We had plenty of those where it was like, we've all been there. We were like, man, okay, we got a week and a half to figure this out. Like, you know, when we charted the first ocean liner, we didn't have the cash. They let us do it in payments, and we didn't have to show proof of funds. So, like, we could have lost the sailing after taking in millions of dollars. Like, I wouldn't suggest it. Or when we bought Powder Mountain in the time between locking up the exclusive right to buy it and hosting people and raising the capital and buying the mountain, we built a $3 million lodge on top of the mountain to drive to that final amount that we needed, I think we were like, 20 million short. And so we took 3 million of our earnest capital, the money that wasn't in escrow, and built this lodge. Had we not completed the transaction, we just would have built the owner as a nice lodge. So clearly, we have a very, very high degree of risk tolerance, or at least used to. And I think that I don't want to name the partner by name, but I have one co founder who'd be like, dude, if we don't get the money in a week and a half, we're out of business. He'd be like, a week and a half. It's not even a problem. Call me next Wednesday. I'm going to play tennis. You're like, all right, dude. So, you know, we certainly, you know, touched the sun a couple of times.
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Kevin Gentry
Well, I got to tell you, I think I've shared with you that the book came at a critical time for me. I was thinking of starting a new business. I just had too much apprehension about it, and it really gave me the encouragement to go. And I think I shared with you a friend of mine from Santiago, Chile. He and I have been working on different efforts in Latin America for a long time. And we had this idea about bringing together in communities some people who were very concerned about human freedom together in one spot. We picked Lima, Peru, and we just said, let's just do it, and let's just do it in a few months. And it was about three weeks out where we were like, we really probably ought to pull the plug on this. This is crazy. We are in over our heads. It's not going to work. And I'm telling you, it was just like, let's just go, what's the worst that can happen? And it worked. And there's a lot to be said for just going. Well, tell us a little bit more about First Summit and then Powder Mountain. First Summit, in terms of it's not just an event, it's a community. And you and you talked about how cultures is important to that. What's the goal? What are some good things that have come out of it as a result of bringing people together like this?
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Jeff Rosenthal
Yeah, we always refer to it as a mutual aid society. You know, this idea that our liberation is bound up together. And, you know, I genuinely get more pleasure out of being a part of the stories of people who I either care about or am inspired by and supporting those people and the things that they want to achieve in the world. I certainly have my own ambitions that are also equally unreasonable. But, you know, it's what made us real community builders, I think, you know, there were a thousand others that started around the time we did. Ultimately, the reason Summit really lasted and was durable was because the people at the top of that organization truly were doing it on behalf of a community. It was not a scheme to eventually make money. It was really about what we were saying, what it was about. There was no extractive, ulterior motive, and people really felt that. It also leads me to not really wanting to give you the examples of all the things that came out of it. There's 30,000 members around the world, every generational founder, creative policy leader, you name it. There's amazing things that came from this community. Those are their stories. They're really not my stories. And that's another thing that I was always pretty allergic to. And every journalist would ask the same thing, be like, okay, well, tell us about the outcomes, like who partnered with who and what happened here. It's like, you know what? That's really their business. That's not our business. We shouldn't claim those successes because frankly, an introduction, a connection that's 0.01% of what it takes to build anything. And then it's a decade or more of a lot of people's life's purpose and work and just the amount of time and effort and energy. And so I'm very apprehensive to really like claim those successes as our own. What I will say is that there's billions and billions of dollars of companies that were formed and impact areas that were underwritten, and marriages and children and all of these really amazing and wonderful outcomes that came from Summit. But I think that foundationally, that idea of a mutual aid society is not for everybody. There were moments where Summit got cool and people were like, oh, yeah, yeah, yeah, that's me. That's what I want to go and be a part of. And when they got there, they didn't really feel comfortable in that kind of an environment. Right. It's very much self selecting and, you know, for those that love it and enjoy it, there's really still nothing else like it.
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Kevin Gentry
All right, so Powder Mountain, how did that come about as an idea? I mean, were you just sitting around like, hey, let's just go buy a ski resort. And again, it's just like, Summit is not an event. Powder Mountain is not just a ski resort. What were you trying, what have you tried to achieve there?
- [28:33]
Jeff Rosenthal
Yeah, sure. So I'll tell you the story, Powder. So we have amazing mentors. Just our friends and our mentors put us on game again. I can't overstate how non intellectual, how meddling we were as entrepreneurs. We're decent, we're not great. We're not peers with the best in our generation when it comes to like scaling, operating and executing a world class business. But, you know, with, with the friends and the, and the mentors and the people that we had gathered around us, we really had amazing references. And so summits rolling and people are like, man, you really got to learn about Black Mountain College. You got to learn about the Bauhaus was a physical building a place in Austria, Incredible culture. You could be Kandinsky, you know, like building the foundations for impressionism. And you're still gonna teach house painting classes, right? And so their idea was, you know, we're all just blue collar people and we reach moments of exaltation and make great works. And then we come back down and we, you know, make a sandwich and go to bed and take a shower like every other human on the planet. There was, you know, gerTrude Stein in D.C. in her salons, or Catherine Graham, or I'm sorry, Gertrude Stein in Paris, Catherine Graham in D.C. there's just these wonderful examples of these physical places or these communities that came together that had lasting impact. And so for us, we had this sneaking suspicion that for Summit to be able to stand the test of time, or at least a culture, because it doesn't even need to be Summit in name, but the culture of this community, it would need roots. It would need a physical home. So we looked at Soho House type models, we looked at beachfronts, and we were 27, 28 years old. We had never developed anything or built anything vertically. So, you know, a lot of hubris to even consider it in the first place. But we were always like, you know, when it's the right time, in four or five years or whatever, maybe we'll pursue this. Powder Mountain was a broken private equity deal. There was a group called Pranaya out of Japan that had 18 golf resorts and one ski resort, most of which were underwater. And it was quietly for sale. And so one of the members of our community had had a home out there, said, guys, you got to come and see this place. And we're like, you're a moron. There's no way we'll ever do this. And we'll see you on Saturday because we ski. And we had heard about Powder Mountain. It's the largest ski resort in America. You know, it's this legendary place that, you know, people who ski there say they ski at Alta. You know what I mean? It's like just that's the rule. And we get there and we're standing on top of the mountain and we're looking out over the Great Salt Lake and we can see four states from the top. And we're like, this is our destiny. Like, we now have to do this funny story. So we threw an event called Summit Base Camp in Squaw valley. We had 750 people there. And on the last day of the event, about 60 or so of them got a note from us saying, like, hey, change your flight. Meet us behind the hotel tomorrow morning. We're not going to tell you where you're going. And so there was a bus, and everybody gets on the bus and they go to the airport in Reno and there's an unmarked gate with no destination on the screen. Like it's Harry Potter going to Hogwarts or something. Everybody gets on the plane. I get to get on the mic and, you know, do the announcement and we land in Salt Lake, take everybody out to Powder Mountain and do our first event and kind of tell this first group our vision for, like, buying this Mountain and building this community. It took us about a year and a half to crowdfund the money from, you know, people who we had built a reputation of over promising and then over delivering. You know, we were lucky to get some fantastic investors who the sentiment was basically like, guys, today you are not able to succeed at this. But we believe in your capacity to actually learn and grow into this to where we think that you will be able to succeed in it. And so again, very, very lucky that we had these founding members that took this risk on us. And then we built about five and a half miles of roads and infrastructure, five neighborhoods, deployed about a quarter billion dollars of capital. We had an incredible time. We were hosting every weekend over that two year run, hundreds of people, music and food and activities. And as soon as those people left, all of the master planners and architects and land planners would come in and we would run these charrettes throughout the week to figure out how to actually do this right. So it was insane. But we were young and we had the energy. So ultimately, you know, we grew that over quite some time. It was considerably harder than we thought. Again, like just, you know, reckless naivete, honestly. And I think we got pretty lucky, you know, like we did build a plane while we flew it. And we ultimately sold controlling interest about two years ago to Reed Hastings, the chairman of Netflix, who is a long term neighbor at the mountain, who's now the CEO and goes to the office every day and runs the resort and has very generously contributed nine figures of capital additionally to continue the development and the art programs and all that kind of stuff. So I'm still a co owner, albeit a small one. It's now the Reed show, which I couldn't be more thrilled by. And we're still neighbors, we still host events up there all the time. And I think the vision now Reed took what we had done and then he ended up, first of all expanding the resort even further. It was already the largest resort in America. The announcements that you're going to see in the next couple of months are pretty astounding. And he took half the mountain and made it private, and half is public. And so there's a bunch of other fun things that we did out there. There's tons of stories or whatever, but his philosophy is one, he wants to make a more approachable and achievable private resort with powder. And there's 10,000 private golf courses. There's like one private ski resort in America right now. And so this is the way that there's really a financial model to do this. Like, frankly, it was always a struggle. I mean, again, like, we were so naive. We raised the first whatever, 40 some odd million to buy the asset and we're like, oh, roads, infrastructure. That's right. We need more money and, you know, municipal bonds and EB5 financing and, you know, it was a real crash course. But what I'll say is calm seas make for shitty captains. And I couldn't be more grateful for the whole road.
- [34:47]
Kevin Gentry
Well, Jeff, what is the difference between a bold plan and a reckless plan?
- [34:53]
Jeff Rosenthal
You know, these days I, I advise against the build the plane while you fly it metaphor. Like, that's a very dumb way to build anything and nine times out of 10, you're going to crash the plane. Don't do that. You know, these days I measure 10 times before I cut once. You know, I'm 40, I have 20 years of experience in business. I have all of the relationships and network and platform that I didn't have when we started Summit. So the idea that you would just use, you know, endless, like boundless energy to, you know, pave over your mistakes, can't do that at 40. It's just not going to work. And once you start playing, you know, at a higher, say, risk reward level, you don't get the same sort of leeway. Like today if I, you know, we raised our, our firm, our fund, our first fund with our investment firm CIV. It's a $210 million fund. If I deploy it recklessly, first of all, I'm, you know, absolutely betraying the trust that my investors have put in me. But also, if I blow it, there is no fund too. Like, I need to go into a new business. So, yeah, my, my advice would be, you know, foundationally, if you have a big idea, you have a bold vision, stabilize that idea. You know, like, really talk to as many people as you can who will beat up your idea and tell you all the ways in which you're wrong. Sometimes they're right and sometimes they're wrong. You know, if they're a category expert and you want to do something innovative, they're going to be biased to things not changing and not working. Right. They don't. They don't, you know that that tends to be the case also in big institutions as opposed to, you know, your rebel alliance. So, you know, when we started Civ, just to put it in perspective, the first thing we did is met a dozen law firms, which seems counterintuitive, right? It's like, what, what do you mean? Meet a Dozen law firms. It's like, well, they all work with all the other kinds of companies that look and smell and act a lot like we will. They have all the category expertise. They've seen the ways to do it that are right and the ways to do it that are wrong. And frankly, they want to win your business. Right. And so you're going to get some really amazing reference calls with those people who are also experts. And we tend to do this like now at this age. I want to take hundreds of meetings on a topic area and I want to understand all of the different ways that something can be done and then you can really diffuse that and determine what it is you want your version to be. Yeah, so I was a bit. I just didn't have mentors growing up in that way. I didn't know anybody that had built like a big scaled entrepreneurial endeavor Growing up in Dallas, Texas, it just wasn't my community. So I didn't pursue mentors. I pursued peers. I went this way, not vertical with something. Right. And so that doesn't really help you miss the, say, hardest one lessons when we're all kind of learning them together. You certainly had a greater set of resources, but it wasn't like you had somebody with gray hair who had done it before shoulder to shoulder with you. And so had I been able to rewind the clock at Powder Mountain. I wish that I had just given a third of the project to Barry Sternlicht and Starwood and say, hey buddy, you run it. Here's a third of it for free. Make us all rich and successful and all do what I'm great at, which is building events and community.
- [38:11]
Kevin Gentry
All right, well, tell us about your new venture, Civ. You referenced it, but what's your vision there?
- [38:16]
Jeff Rosenthal
Yeah, I am in this really incredibly lucky place where my previous ventures were successful. I've built this amazing community of people. I have kids. I've had a successful outcome in a business. And so my back's not really against the wall as it once was. And I had this luxury of thinking, okay, I'm 40. These are probably my Jordan years. The next decade or two are going to be the most productive years of my life. What do I want to do? How do I want to spend my time? And fundamentally, I believe that nothing great happens in under a decade. That is the minimum it takes to build real wisdom and real scale. And that means that you better love the next thing that you are doing to be intellectually stimulated in a way where you want to show up and drive for A decade. I think the Japanese have this right. Whatever it is that you do, build a business, drive a bus. This is all the rock in which you sharpen yourself against in life. It's just all a path to self actualization. And in this case, I happen to have a best friend, my co founder, Patrick Maloney. Patrick's built and scaled and sold three businesses to Publix in the energy sector. And he and I had moved to Austin right around the same time. He had sold his previous business Inspire to Shell. I had sold Powder Mountain to Reed Hastings. And we were down in Austin during COVID really kind of in a similar space. And so we went on this. First we had to determine whether or not we should build together. Just because you're buddies doesn't mean you should. So we actually wrote each other like pen pals after we'd have these dialogues and conversations because you know, in a conversation there's things that can be lost. And so things as simple as like what time do we get to work, right? Like what level of in office participation is required of all of our employees? How do we both feel about that? What's the culture that we want to create? You know, we then looked at holding company models, incubator and accelerator models and we ultimately arrived at this back end build structure that we're now deploying at siv. So SIV is short for civilization. We both back companies and also will co found companies on platform. So we still get to, you know, exercise our entrepreneurial spirit in a way. It's certainly entrepreneurial building an investment firm like it's a startup, like any other startup. But we also still have this function where we actually can launch things off the platform. In terms of the why, I think that this is a very, very unique time in history. You have this inflecting energy demand driven by compute and reshoring. You essentially have these multi decade megatrends all coalescing at the same time. So first and foremost AI and compute, you have both the immense power needs behind it. You have the whole digital infrastructure vertical. And then you also have how AI will truly transform every single aspect of society and business. We're then reshoring, after 30 years of globalization, critical industries of all types, right? And without deep, deep advanced manufacturing and automation coupled with software enablement, it will not happen. We just fundamentally do not have the assets required to reshore these industries in the United States and build them new. You know, right now we don't refine uranium in the United States, we don't refine lithium. We have one copper mine that's at full capacity on a global scale. Right. So, so ultimately we don't make transformers in the US right now. There's just a thousand of these things that we need to do really for long term prosperity and it will require a real industrial evolution to take place. And then the third is power. You know, we say that we want to electrify everything. We want a 3x electricity consumption in 10 years. This is a physical impossibility. You can't scale power like the Internet. It just doesn't work that way. This is steel and this is rebar. This is concrete and this is like dudes in hard hats and work boots on job sites. Like just does not scale that way. So it's also now becoming clearer and clearer that it's a national security imperative and it always was the greatest input to prosperity. So I think we're energy blind in our society. We just don't really realize how foundational power is to all of our prosperity and how it always has been. If you look at healthcare outcomes, education outcomes. And so we invest across all these things, energy, robotics, AI, supply chain, logistics, manufacturing. We're very founder driven. Like I've just never seen an outlier company that wasn't built by an outlier founder and a remarkable team. I don't believe in hired guns. Like I'm not going to take over that business and run it if that founder who had that vision isn't present. I just fundamentally don't think it can be a venture scale return, which is a very specific thing. Like there's plenty of amazing businesses in America that you can build. You know, you can make millions of dollars, you can sell those for tens of millions of dollars. That is not a venture scale return. This game that we are in is about 20x outcomes, right? So you know, we, we tend to focus on scale tech, not deep tech. Meaning that, you know, we're not doing things that are, you know, with, with significant science or technology risk. If it's in the lab, it's not for us. Not a PhD, I can't help you there. But we do fundamentally believe that the chasm to cross with the vast majority of things is one of execution, not one of pure invention. We then like to test customer demand. So we literally underwrite and subscribe commercial partners through our investment process. Founders love it, right, because they walk with really high trust, high reference customer relationships. And that's the best way for us to know how the market sees that product. Will you buy it on what timeline, at what scale? And then it allows us to back into competitive unit economics. And so this sounds a little obvious, but if you've seen how a lot of these things have been invested in the last five, 10 years, there are a lot of things that people have bet on in huge ways that at the end of the rainbow just do not have fundamentally competitive unit economics. They will not scale. And it's been a blast, man. So this is our first fund. I have one other CO founder named Abijoy Mitra. He joined us from CO2 where he was a general partner and previously was at a firm called Valor Equity Partners. They're the lead directors at SpaceX and Tesla. And we've been building an incredible team here in Venice, California. We actually bought 901 Abbot Kinney, which is the former Charles and Ray Eames office where we've been building like a little innovation campus.
- [44:42]
Kevin Gentry
Well, you are certainly making no small plans. You pack a lot in there. And you know Tyler Cowan, Jeff, you know Brendan McCord. I've had them on recently on episodes where they both talk about with respect to artificial intelligence, we ain't seen nothing yet. I mean, just, it's just going to be mind blowing, the pace of new innovation. So, so good for you. Well, I want to bring this to a, to a close with some, some additional advice that you might give to those listening. The first is what would you share with people who just deal with the psychological barriers of I just can't. Even if I dream this big, I just can't do it. How do you. I mean, it's just easier to listen to those who say, don't do it, it won't work often than it is to that little voice of encouragement. Just go for it. What would you share? What words of encouragement would you offer?
- [45:42]
Jeff Rosenthal
Well, first and foremost, if you think you can't, you're right. Just first principles, start there. If you think you can't, you're definitely right. So changing that mindset, of course is essential. And when I talk to kids these days, like my generation, our problem was hubris. I'm a genius. My idea is amazing. Elon needs to hear about this. Like, call Jeff Bezos, get him on the phone. You know, he needs to know about my, you know, my new subscription shoe company. It's like, who cares, man? But, but we all had way more hubris than we should. I'd say the problem facing today's generation, as you mentioned, you know, there's a great book called the Ancient Anxious Generation by Jonathan Haidt. A lot of it is imposter syndrome and anxiety. Right. I think that just know that the hidden truth of the world is that this is all things that were made by people and could be remade just as easily. And the there are the.01% of exceptional freak show geniuses. Like, I'm sure five of my brains fit in George Church's brain or Elon's brain or Peter Thiel's whatever. Right. But the vast majority of people who have built all the things that you touch and use are a couple of IQ points away from you. It's not like they're or the same. And plenty of people who are not brainiacs have been the ones that have executed and operated and made these things truly happen all around the world. And so, you know, and I think that when you interact with people like that and meet them and humanize them, it really helps you see yourself in that state. Friend or fan is an important early foundational piece of advice I got. It's like you're either going to be a friend of these people or you're going to be a fan of these people. I don't need any fans. I do need friends. I like talking to people who are passionately interested about the things I'm passionately interested in. And if you ask me a good question, I get to reinforce my own knowledge, learning, expertise and enjoyment. I enjoy these conversations. So I'd say truly finding something that you are enthusiastic about so you can build your own expertise and you are worthy in a conversation with someone you admire where you're also adding value. And entrepreneurship's not for everybody. It's okay. I refer to it as an affliction. I'm afflicted by creation. Now, I can say I'm enthused or I can use much more flowery language, but the reality is I'm going to die with my boots on. It's okay. Like, I, I, I know this. It makes me a better husband, it makes me a better friend, makes me a better father. I, for me, it's the fountain of youth. I get, I get energized by this. Plenty of people get drained by this and the risk. I mean, man, if you don't feel well with anxiety, do not do this. Like, it's just not for you. You can work with or for an amazing entrepreneurial company. Like, I encourage that. Like, if you care deeply about a space and you don't feel like you are capable of doing what I'm talking about, go and join an organization that you think has a shot at doing it. I really get annoyed about one of my big gripes with and I'm on the board of Ocean Conservancy. I'm on the leadership council at Conservation International. I do care about irrecoverable climates. I love the earth, I enjoy nature. But a big problem with this movement is just this whole kind of like, oh, our parents generation left us with this legacy and now we're screwed. It's like, dude, then get in the game. Join an organization can solve the problem. Imagine if we talk that way about cancer. Oh, cancer. Our parents generation didn't cure cancer. And now we're stuck with the bag. It's like, no, dude, that's not how that space works. Like, people are inventing the future every day in life sciences in ways that will extend our lives and those of our loved ones. Right? And so I implore people not to put the pressure on themselves to do it if it's not for them. Like, if you, you tend to have a trend line, like, you heard me, I mean, I was like 19, I had like five projects. I didn't even know what entrepreneurship was. It's just like, that's in my nature. It would make me a really shitty employee. Like, I'm, I'm telling you, I promise you, I am a bad employee. Like, I was not good at any job I had. I won't be good at any job in the future. But as like an entrepreneur, as a leader, you know, as a founder, it make it is a skill set. So all it is to say is that, you know, lean into what makes you exceptional. All of us have something, every one of us has a gift. Discovering what yours is and then where to apply it and with whom is essential. I'm also not a CEO. I should specify that like, I know this about myself. I would be a meddling, decent to poor CEO. I'm a fantastic co founder. I'm a really good team member. You know, if you throw me the ball or if you hand me the ball, or if you put me around, you know, the line, I need to stack the quarterback all day long. Not the quarterback, that's okay. And there's no ego around that. And so I guess the only other thing I would say, and this is, you know, run on sentence, but I'm just trying to share some, some, you know, some value here. I'm extremely sensitive to extrinsic motivation. I, I tend to only want to spend time with and work with people who are intrinsically motivated. Um, and so if you're thinking about like the thing that you will buy or how people will view you or any of those things. You're just not going to get there. Like, sure, there's you know, malignant narciss. Get to the greatest positions in society, it seems in this day and age. But if that's not you, which I hope it isn't, and if you're listening to this podcast, you almost certainly are not, you really do need to focus on the intrinsic what truly motivates you. It's going to bring you personal pleasure every single day and assume it's a 20 year run. Like if you don't think you're going to do it for 20 years, don't start. And if you do, if you believe it, then who cares what happens on a day to day basis? Like you're going to, you know, search is in progress. You're going to find it awesome.
- [51:36]
Kevin Gentry
Jeff, I've always enjoyed conversations with you over the years. You have this intellectual curiosity, you have this enthusiasm, it's infectious. Good, good for you. All right, so here's a last two wrap up questions. I always ask this. You're still a young man, but thinking about a younger version of yourself, maybe that 19 year old, 20 year old now, knowing what you now know, what advice would you give to that younger version of yourself that you might have done any differently?
- [52:09]
Jeff Rosenthal
Well, yeah, I think economically I wish I'd bet more on all my friends, you know, like, like the people that inspired me the most generationally ultimately went on and built some pretty incredible things. And if I could rewind the clock like I, I've been investing for a very long time and I've definitely had some of those opportunities early. In some cases I did. And I wish I doubled and tripled and quadrupled down but you know, bet on your friends and I wouldn't really change a thing, man. I mean, I don't know what kind of advice I me today. I mean you gotta remember like at 19, I was still like a jock, I was still, you know, a hustler. I was still, you know, motivated by all the things that like a college kid are motivated by. And to say like, hey dude, you need to prioritize these things versus those. Like I wouldn't have been able to hear it. I'd have been great. I need to learn that, that through experience. So at 19, I mean man, just do your best, forget the rest. Never surrender forever. I don't know.
- [53:18]
Kevin Gentry
Well, you may have summed it up and you've given a lot of great advice, but just the parting words for anybody Listening, who knows the value of casting a big bold vision. And they're hearing from example and they're energized and they're inspired. What do you tell them now? Think of yourself now as coach rather than a member of the team. What would you, what advice would you share?
- [53:42]
Jeff Rosenthal
Yeah, well, well, my job now as a venture capitalist is to do this right. I'm evaluating markets, businesses and people. You know, I'm determining whether or not I believe that there is a real scale to this business or this platform. Like, can this truly be world changing? Right? Then I'm looking at the approach. Like, do you have an approach that is durable? Like, can you build and scale a business in this space that is capturing value and creating value? And then I'd say the most important piece is the people. And is this somebody that I believe is a true outlier? Founder, a 0.1% founder. That means one in a thousand. And a lot of that has to do with leadership. You know, are they coachable? Is a huge piece that we think about. You know, we back people who've built and scaled and won things before. We also back kids that are like straight out of school and they're geniuses with no experience. And the question is, okay, are they coachable? Like, can we work with them? Are they not just us, but anybody? Like, do they think they already have the answer to everything or are they going to be like voraciously pulling in wisdom omnidirectionally for the rest of their lives? People who are idea generators, it tends to never stop, right? Like, if it's somebody who's like, this person could be really good, but they don't really have an idea yet, that tends to not really work. They have ideas all the time. The question is which one to pick and how to refine it and how to make it better, how to stabilize the idea. And then I think the piece that is often overlooked is leadership. Like, can you recruit and lead and inspire a world class team? It's incredible when you see somebody who's like 23 or 26 and it's like, whoa, how did you get like all these rock stars to like leave what they were doing or choose this path to go to work with you versus something more established. Like, that's a real signal. And so I would reflect on, you know, like, do I have those things? Like, am I building into a space that is truly, you know, worthy of my time and other people's time, or is it also ran like, you know, I have plenty of friends that are like, you know, deal brokers, and they're going to make a lot more money than me. I have no interest. Like, I just don't have any interest in just making money off of, like, you know, putting cash and investment together. It's just not that inspiring or interesting, you know, like, is my approach informed by all of the ways that this was done before? Like, the great virtuoso pianists, they didn't just, like, start, you know, playing jazz. They first learned everything foundationally to truly be mastermind masters, and then they started to innovate on top of that platform of what came before them. Right. And so I think that a lot of times people take shortcuts, and that never works out. Like, every time you take a shortcut, you pay for it in the long term. The other example I give is like, you know, what sport do you love, Kevin? What's your favorite sport?
- [56:34]
Kevin Gentry
Oh, gosh, I'd say baseball.
- [56:37]
Jeff Rosenthal
Okay, congratulations, Kevin. You're starting as pitcher. Game 6, World Series. Need you to be in the stadium at 7pm it will be the worst day of your life. Right? Like, you are not prepared for that, and so don't take shortcuts. And then the last is, like, really reflect on, am I a leader? Like, am I. Do I have those qualities where I feel like I could recruit and grow a true team in a culture and a community around this idea? And if I'm not, I either go and work with somebody who has those qualities or I recruit that person as the co founder to build this with me.
- [57:12]
Kevin Gentry
Ah. Lots of great advice, lots of great insights. Those of you who are listening today, check out Summit, check out Powder Mountain, check out Civ, check out Jeff Rosenthal, and definitely get your hands on make no small plans. If these ideas at all intrigue you, you're going to be motivated further by reading it. You're going to get all kinds of ideas. I took notes and it was incredibly informative for me. Jeff, I'm grateful to you and your co founders for giving me the ideas and inspirations to launch my business and even to launch the Going Big podcast, which I attribute its name to you and the book. So thank you very much. And by the way, for the past several weeks, it's been number one on iTunes in the nonprofit category because I wanted to think big from the outset. So thank you very, very much.
- [58:01]
Jeff Rosenthal
Kevin, you're the man. I mean, that's reflective of your efforts. It's very flattering and kind of you to say, but it. It's not true. You're the man, that's why.
- [58:08]
Kevin Gentry
Oh Jeff, it's great to be with you again. Look forward to many more occasions. And ladies and gentlemen, keep your eyes on Jeff Rosenthal for many years to come.
- [58:17]
Jeff Rosenthal
Thank you Kevin. Thank you for listening.
- [58:19]
Kevin Gentry
Thanks for tuning in to the Going Big Podcast. I hope today's conversation left you feeling energized and ready to tackle your biggest goals. Don't forget to subscribe and leave us a review on iTunes, YouTube, or wherever you listen to podcasts. It really helps spread the word and it gets these inspiring stories out to more people. You can also find more content, resources and updates at our website goingbigpodcast.com Remember, the only limits are the ones you don't challenge, the limits that you impose on yourself. Keep pushing, keep growing, and above all, keep Going big. See you next time on the Going Big Podcast.
- [59:02]
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