Jeff Rosenthal
Co-Founder, Summit
I like saying that leaders don't have followers — leaders create other leaders.
Summary
In this week’s episode of “Leadership Matters,” Summit Co-Founder Jeff Rosenthal joins Alan for a conversation about Jeff’s career, the incredible history of Summit, and the lessons in leadership that Jeff has learned over the years.
Founded by Jeff and a set of friends in 2007, Summit is an organization dedicated to bringing together innovators, entrepreneurs, and leaders from a wide variety of backgrounds and industries through novel events and festivals. Make No Small Plans, a book released by Jeff and his co-founders in 2021, tells the unique story of Summit’s creation and Jeff’s persistence in the face of adversity. Today, Summit continues to grow and has developed new lines of business from unexpected sources, including through Powder Mountain, the ski hill owned by the organization in Utah.
In their conversation, Jeff and Alan discuss Jeff’s early life, how he maintains a partnership model with his co-founders, and the importance of market-based solutions to some of society’s most pressing challenges. Jeff emphasized how the ideation process for Summit has changed over the years — as the organization grows, it has had to adopt new models that can accommodate its growing strengths and changing circumstances.
Mentions & Resources in this Episode
Guest Bio
Jeff is the Co-Founder of Summit, a cutting-edge organization best known for hosting global ideas festivals and events, and is the co-owner, principal designer, and developer of Summit Powder Mountain and Powder Mountain ski resort in Eden, Utah.
Jeff currently serves on the Leadership Council at Conservation International, and on the boards of Beyond Conflict and Street Soccer USA.
Jeff is Co-Director of the Summit Action Fund, a venture investment fund making investments in startups that drive innovation and positive market disruption. He is a Founding Partner of the Drawdown Fund, and Senior Advisor to TPG Rise and TPG Growth.
Jeff serves as a Senior Advisor to many for profit, and non-profit organizations, including Inspire Energy, Calm, Scopely, Seed Biosciences, Learn Capital, GivePower Foundation, Arabella Advisors, a leading philanthropy and impact investing consultancy, and Laurel Strategies, a global business advisory and strategy firm.
Jeff is on the Leadership Circle of the Conservation Lands Foundation, the Advisory Board of Whistleblower Aid and Save the Waves Foundation, and a Senior Advisor to One Community Films.
Jeff was a founding board member of the Summit Institute, the Summit Fellowship, and founding board member of the Anti-Recidivism Coalition.
Jeff is a member of the Pacific Council on International Policy, and the recipient of the Tribeca Disruptive Innovator Award.
He is also the co-author of Make No Small Plans, released in 2021 by the Crown Publishing Group.
Clips from This Episode
On the evolution of the organization and how its various endeavors have expanded
On Jeff’s advice for young entrepreneurs just starting in business
Episode Transcription
Alan Fleischmann
You're listening to “Leadership Matters” on SiriusXM and leadershipmattersshow.com. This is Alan Fleischmann, your host.
My guest today is an inspiring and visionary entrepreneur working to convene thought leaders from across the globe. Jeff Rosenthal is co-founder of Summit, an innovative company on the cutting edge of global ideas, festivals, and community-building events. Since its formation in 2007, Summit has held over 250 high-powered events with prominent speakers ranging from Bill Clinton to Jeff Bezos. In addition to its trademark speaker series, Summit also operates the Powder Mountain ski resort in Utah and the impact-driven Summit Action Fund. Jeff and his co-founders recently published a book, Make No Small Plans, about the company's history that also serves as a guide for young entrepreneurs in the modern era.
Jeff's leadership extends far beyond Summit. He serves on the boards of numerous companies and nonprofit organizations, including Inspire Energy, Seed Biosciences, the Anti-Recidivism Coalition, and many more. I have the privilege of working closely with Jeff in many areas where our paths intersect and it is truly one of my great joys, my great pleasures. He's a good friend — a great friend — an admirable leader, and a brilliant entrepreneur. I think he's one of the most optimistic, and pragmatically optimistic, people I know. I'm really looking forward to our conversation and to dive into his life, his career, and get a little bit about his vision and best practices so we can share with all of you on “Leadership Matters.” Jeff, welcome.
Jeff Rosenthal
Thank you Alan. I like that, “pragmatic and optimistic.” I appreciate it.
Alan Fleischmann
I think of you as being someone who always finds the silver lining. But when you say that about people, often people think that you're not in reality — the reality with you is, you get things done.
Jeff Rosenthal
Saul Alinsky wrote a great book on this, Rules for Radicals. The term he coined in the late ’60s and early ’70s — which is pertinent today — is this idea of practical radicalism. So you want to be radical, you want to change things, but you’ve got to do it in a way that actually gets them done. It's not about what you say, how you look or the team affiliation: it's about the scoreboard, it's about what ultimately changes and what happens.
Alan Fleischmann
I also think of you as somebody who understands how to make partnerships work. And that's really hard, that doesn't always work.
Let’s start by going back in time a little bit. The world knows you — and those who know you, know you — as a first-class convener of executives, leaders, and celebrities. But you have far more humble roots. I'd love to hear a little bit about your early years in Texas. What was your family like? I’ve met some of your family members, so this is interesting to me.
Jeff Rosenthal
Well, I grew up in Dallas, Texas. I graduated from high school in 2002. I have a great family, in Dallas, that that's been in Texas for five generations. I just grew up middle, middle-upper class. I certainly was born in field goal range, so I don't want to give the impression that I was from super humble beginnings. My family is certainly successful. We weren't mega rich or anything — there's no trust funds — but I wasn’t without.
I definitely credit the large family gatherings. Grandma was this real matriarch and she would host aunts, uncles, and cousins. On like a weekly, bi-weekly basis, I would have like a sixty or seventy person gathering, some big meal or some big party. So I always had this sense of this large extended family being the greatest luxury in life.
And I played soccer, I was a soccer player growing up. I went into a residency program at IMG Academy my senior year of high school in Bradenton, Florida. Where US Soccer is based, or their youth program. Then I went to American University, I got a soccer scholarship. But, you know, my talent really stopped right about there, maybe 16, 17 years old, people got much bigger, much faster, much stronger, and I kind of peaked. I was an entrepreneur without really knowing what the word meant. I had never heard the word, I didn’t know the definition. But I started little companies, I was throwing parties. College is actually where I met my co-founder of Summit, Brett Levy, we threw parties together. He went to George Washington, I went to American University. We combined forces and the rest is history.
Alan Fleischmann
So tell me, how transformational was American for you?
Jeff Rosenthal
American was incredible. Because Texas, at least at that time, was very conformist, it's a smaller world. I live in Austin now and there's so many cool people. Dallas is a nice place to grow up, but I couldn't find the examples of the lives that I wanted to lead around me in my community. It is a bit sheltered, you know — you know one culture, you know a couple of different groups of people. Luckily, I had sports, so I opened my network much further — my understanding, my aperture.
B\ut going to American is incredible, because it's kids from hundreds of different countries, you're just making friends from all around the world. And I think that, again, was incredibly foundational for what I ultimately ended up doing and building at Summit. And DC was incredible. I played soccer, I quit my sophomore year, and I started throwing parties. I started a couple of companies, little side hustle things. And then I worked in Congress. I started as a congressional intern, and I ended up becoming professional staff and floor staff for the Rules Committee when I was like 19 years old. So DC had a tremendous, tremendous impact on me.
Alan Fleischmann
And did you want to be in DC? You got a sports scholarship…
Jeff Rosenthal
No, I thought I'd play pro soccer, man. I was naive. I was getting recruited by, perhaps, better soccer programs — South Florida or SMU — but I went on a visit to American, I went out in DC and met the people. And I was like, “this is me.” It's just something in me — even though I was a punk at 17, I knew that going to a remote, rural school in the middle of America wasn't going to be the most service to me as a person. But yeah, I really, honestly thought I'd be an athlete.
Alan Fleischmann
And do you still play?
Jeff Rosenthal
No, I have a game here I play like once every two or three weeks. It's an all-Israeli pickup game. There's a cardiologist on my street, it's his game, and I don't speak Hebrew. So it's great, because they just yell at me, I don't know what's happening. But it's nice.
Alan Fleischmann
You assume they’re praising you, they're probably cursing you.
Jeff Rosenthal
No, they’re definitely not praising me. You get the heat when you when you make an errant pass out there.
But no, I don't really play. I’m a skier now Alan, as you know.
Alan Fleischmann
You are a skier, which I want to hear about.
Going back to your AU days, did you already get a sense of the power of convening even better, or was that something that started to come into your life afterwards?
Jeff Rosenthal
I had this moment when I was a kid, where I was pretty… I went through some childhood depression stuff when I was really young. I have a pseudo-photographic memory, so I skipped a grade and went to a special learning school. I just had general trouble relating to other people. I didn't make friends easily, I didn't feel like I was well understood.
And I remember, I had this moment where I woke up one morning and I had these dual realizations my freshman year of high school. One was, life is too short to be unhappy, so you have to choose happiness. And two, you can learn something from everyone. It just totally changed my approach. It didn’t matter who you were — you can be, you know, a friend of my parents, a classmate, or the janitor. Somebody had some life perspective, some experience, some way of being that I could incorporate into my own life.
I think that American and DC were an accelerator of that. When I was a young entrepreneur, when we were in our early 20s, if you had pedigree, we would kind of write you off and be like, “oh, your dad owns the dealership, get out of here.” We would immediately not be interested in what you had to say. And what we realized rather quickly was that there comes some credible wisdom from just being around brilliant people. I think that having that internationalization of my network and perspective, having experience in politics at a young age — so I could get jaded quickly and focus on market-based and philanthropic solutions, and influence and sentiment as opposed to… it’s a longer conversation, I know that you're quite active in proper politics. But yeah, it was just huge. So if I had to do over again, I would run it the same route.
Alan Fleischmann
I love that. When you say you chose happiness, I think that's a very profound thing and a difficult thing to do.
Jeff Rosenthal
I was like 14, dude. I didn't choose anything, I said this to myself in my own head.
Alan Fleischmann
Did you start reading things that made you inspired?
Jeff Rosenthal
Honestly, not until I was literally graduating from college, because school was really easy for me to get by — I was a solid 2.5, 2.7 student who never had to study. But really, leaving school was when I was exposed to this idea of like intellectualism, of personal growth and intellectual growth of my own volition versus what my school was teaching me. I already was an entrepreneur, I was starting events and starting these companies, but I didn't know that that was a learning safari as well, that that was like an infinite game that I was playing. It was just me expressing the extra energy that I had.
I left school, I moved to New York City, I traveled for about nine months and spent what money I made in college. But there was maybe a year and a half period where I just kind of sent myself to the college I didn't have in the four years I was an American. While I loved it and I love DC and it was formative, I didn't really learn a lot inside the classroom.
Alan Fleischmann
That's awesome, I love that. The kinds of things that you did right after college, tell us a little bit about that time and whether you got to go out into events and planning at that point.
Jeff Rosenthal
Well, while I was in school, there was some promoter on my campus who was like, “you're friends with everybody, you know everybody, you should throw parties.” I was like, “that's a horrible idea, you're an idiot.” And then of course, six months later, I was like, hey, I’ll throw parties! And I really loved it. I just always enjoyed seeing my friends enjoy themselves. I like being in the center of the action without being the center of attention, and being the host is a great way to do that. And from an insecurity perspective, the greatest and easiest way to make sure you're invited to stuff is just to throw it yourself.
Over time, we gained this incredible skill set of how to really build remarkable global events and surreal experiences, but after school, I moved to New York. I traveled for about eight months around the world. I went to Asia, primarily, in and I went to ESADE University in Barcelona for two months. In a Spanish business class, in Spanish, when I don't really speak — it's just all lost boy stuff. I interviewed in maybe 10 different industries when I got to New York City, and no one hired me: advertising, finance, you name. They were just like, “you definitely are not an assistant account executive material here at XYZ.” Hot Jobs didn't hire me. I went to try some Yahoo Hot Jobs, and they were like, “this kid's going nowhere.” I ended up getting into the buyer development program at Macy's. So I was a planner in lingerie at Macy's at like 22 years old — they placed me, it wasn't a passion. And you're essentially just buying for 156 doors, tens of millions of dollars of intimates. You're allocating that based on the sell through and turn ratios. It sounds a lot more complicated than it was. It was very much a job an AI could have done better than I did it.
Around that time, I had started another website called whatyouneedif.com. I started a little clothing company called Line Design, nothing worked, it was all the little tiny projects. But Brett called me one day, my co-founder at Summit who was my college promotions partner. He's like, “hey, I met this guy Elliot in DC, we put together this little event for 19 people, we're gonna do another one for 60 and it's all young entrepreneurs. And you know, we want help to bring in some sponsors or some people or something.” I was like, “dude, that's the greatest idea I've ever heard.” Like, I woke up this morning, I had no reason to reach out to anybody. I remember going to like the TED event in New York, randomly like walking into some office to watch, just to try to find anybody that was into intellectual self-improvement in this way. I couldn't find it. It was just so… not even nerdy. Nerdy people were doing deep stuff, focused work. This was, again, very much on an island. And I was an entrepreneur, but I wasn't a particularly talented entrepreneur. And then I heard these words, and it was like the skeleton key for me to reach out to whomever I wanted to in the world.
And within the next two or three months, I had made my decision that I was going to join this Summit idea full time. I gave away my furniture, I paid my rent, but I left my apartment and I moved onto Brett's couch in DC, where he and Elliot were based. Our fourth co-founder, Jeremy, who was Brett's high school best friend, was on the work tour with his rock band. He went to Berklee School of Music and they were, like, the most technically talented music nerds that just played like slot-metal emo, whatever Warped Tour was in 2009. He was the most creative person we knew, so we convinced Jeremy to join us as well.
That was the genesis of this thing. The time from the first event Eliot put together, the first 19-person Summit, to us hosting our first event at the White House, was 270 days. So it was this unbelievably exponential growth curve. I'll in my 10 minute answer to a simple question with saying that, because we were so clearly the youngest, dumbest, least experienced people in the room, it made us real servant leaders. We were absolutely wrapped with interest in what everyone around us had to say, what their perspectives are, what their life experiences were. We really wanted to provide value to them. We knew we had this like once in a lifetime opportunity, as some perhaps fifth-round draft picks, to really be in the game.
Alan Fleischmann
That's amazing. I love Summit, I love what you're doing and I think you and your partners have done phenomenal things. It's quite extraordinary, because you get government leaders, you get people at the presidential level, you get iconic business leaders, you get iconic artists. When you think about it, you truly transcend public, private, civil society, music, arts, culture, global, and you bring this really eclectic group of people together, who then draw in other eclectic people who are not necessarily onstage, but are right there sitting in the room with you.
And I'm curious, was that the original vision for this, was there a void that you thought you were filling? In those 270 days where you were figuring out how to scale and to scale so quickly, what was it that you realized? That there may be a generational shift, or even a new paradigm?
Jeff Rosenthal
from the very first time we gathered a group, it was evident to us how valuable this would be, to everybody involved. I think that the relationships that we have determine the future course of our lives, including people in our trusted, close circles — it is the greatest gift we can give them. Literally, our greatest punishment as a society is separating people from people. So it can't be overstated how deeply valuable we think what we do is. It's not as quantifiable, because it's not like… If you start trying to quid pro quo it or get paid for an introduction, that kind of thing when you're not really giving unselfishly, you're not really trying to create an ecosystem of goodwill, a community. You're trying to, you know, game-of-trades it. You're trying to extract value. So I think that we naturally — myself and my co-founders — we get a ton of pleasure out of helping people who we admire and respect, whether they're on the way up and they're young founders, or they're people that are luminaries that we have the great pleasure to be a part of their story. We get to gain wisdom, experience, friendship.
And certainly, there is incredible value that those relationships can unlock for you. But I think that for us, the moment was right. First of all, because it was sort of this moment of web 2.0: the social web, and iOS, Apple’s ecosystem for building apps. And so you had all these like twentysomething entrepreneurs that could stand up a company overnight. There was no Dropbox, there was no Gmail, there was no iPhone in the generation before us. So you all, of a sudden, had this generation of twentysomethings that can start a company, build a company, and get a product out there in the world, maybe faster than ever before. I think that, simultaneously, all sort of the silos between those different industries and disciplines really have broken down. Arbitrage between silos has always been how great fortunes and power has been created. The spice route of the 1400s is like the innovative, silo-jump of today, in a sense.
But if it was 20 years ago, Summit — this interdisciplinary, intergenerational community and set of experiences — would make no sense. You would really get the most value out of gathering with people in your particular discipline. I think that because we're seeking innovators in their field regardless of the discipline that are also kind, open-minded, nice people, it creates an incredible culture that's very open-minded. People do your networking for you and you find people that truly share your passions. That's really what it's all about. I don't care about your stature; I care about the dynamism of our conversation, the enjoyment, the laughter, the friendship that we get to experience together. And by not being in each other's fields, we actually share tremendous perspective that we otherwise would never see.
So for Summit, that's our scorecard, our key performance indicator: what great relationships do you leave our experiences with? Now we host talks and music. We have great chefs and performances, we have immersive art programs as you mentioned, We create this social sculpture, this Ideas Festival, this three-day, choose-your-own-adventure flagship model. We also, of course, own Powder Mountain, the ski resort and Eden, Utah, to build a town really dedicated these generational ideas on top of that mountain over the last eight and a half years.
Alan Fleischmann
Tell us about the mountain, because that also shows your incredible innovation. You can go back to it too if you want, but I definitely don't want to miss that.
Jeff Rosenthal
Yeah, I guess we'll go to 2013. And this is a big part of our book, Make No Small Plans, which is from 2008 to 2013. So it's this moment from when we started summit to really buying Powder Mountain. It’s the largest ski resort in the US. Around 2012, we were really starting to master on medium, in a small way. We were chartering ocean liners, taking over mountain towns — having Questlove DJ on the mountaintop, John Batista on piano in the lounge, and Alice Waters cooking the farm to table meal. We started blending all of these fields, all of these generations in a way where everybody was so appreciated. To your point, at that base camp event in 2012 in Squaw Valley, there were 18 Secret Service members because of the heads of state that were there. We also had Diplo, Questlove, and the founder of Burning Man, Larry Harvey, leading a talk.
So this is this is 10 years ago. Some of the great entrepreneurs of our time have really been foundational in Summit — I don't mean to be so superfluous, but it's true. These are the luminary entrepreneurs in our generation, they were part of Summit from the beginning of this. So we thought that, if this community is going to last over time, it really needs roots. If you look at Black Mountain College, if you look at the Bauhaus, if you look at some of these movements, they had at home. We were so naive and so on our Blues Brothers mission from God… We had so much confirmation bias because of our early successes, we thought, “hey, we can do anything.”
When we heard that Powder Mountain was quietly for sale, we flew out the next day, on a whim. Because we had heard of it; we're all big skiers and snowboarders and we'd known about Powder Mountain as this backcountry haven. We flew in from LA, we were living in Malibu at the time. It's an hour drive from Salt Lake City and then you drive up the mountain and you actually ski off the top. It's a kind of a plateau at the top, you look out over four states, the Great Salt Lake, the mountain ranges in the foreground and the background. There's a lake at the bottom, in this green valley with the Snowcat Mountains. We were like: this is our destiny, this is absolutely worth it. We have to do this. Should we do it? No way. Of course not; we were like 27 years old, we didn't have enough money, not to the point that we could buy a mountain.
We ultimately, over about a year and a half period, not only ran the transaction, ran 160 point due diligence checklist, purchased the property, hosted thousands and thousands of people out there, and then essentially crowdsourced the money from the Summit community to buy the mountain — we've since build five neighborhoods and five and a half miles of roads and infrastructure, and we've run the ski resort for nine years now.
Alan Fleischmann
Do you have a house there?
Jeff Rosenthal
I have land there. I'm still waiting on my Alan-sized liquidity event to build my second home. But you know, perchance one day.
Alan Fleischmann
That's pretty cool. How often do you go?
Jeff Rosenthal
I live there at the beginning of the pandemic with my family. We did four months in Eden, it was amazing over the winter. We only did a couple of weeks out there this year. My kids are at primo preschool-after-school-activities age. At the mountains, it's funny because you think they're gonna love it, but they're ultimately outdoors for what, an hour and a half a day max? So when you’ve got the really, really little kids, it’s either surgical strikes or you’ve got to just live out there. It's one of the other.
Alan Fleischmann
That's a very smart thing. Has the mountain lived up to your and your partners’ expectations?
Jeff Rosenthal
It’s funny, because we ultimately built a town, but one of these quotes that we love is “gardening, not architecture.” We had no expectations. We didn't think we're going to buy a mountain or build a mountain town. What did we think it was gonna be? I'll tell you. It's far, far beyond my expectations from when we started the project.
I think that there's these naive visions that are more values-driven about the culture or like the vibe or the feeling of a place or a project. You need those, because that's the North Star. But you don't land on the North Star; you land on the planet adjacent to the North Star. You have to sort of formalize and actually refine that visionary concept. What I never could have imagined, that I'm so grateful for, is that after 15 years of hosting events, large and small, over most of my most of my adult life… It used to just be very singular. Summit hosted everything. Every weekend, we hosted an event. Every couple of months, we'd host the bigger event. It had to be different — we’re always having to outperform ourselves, it's all on us to build the vibe and the body heat of the place.
Now, there's a really thriving community of neighbors and community members that love Powder Mountain and host their friends there. So it's more like a solar system. I can drop in, just selfishly, and I can go to other people's experiences, I can meet their amazing friends. It's not all reliant on the work that I did that season, right? So as I'm getting older, I'm deeply appreciative of that phenomenon.
Alan Fleischmann
I love that. You know that you’re scaling when other people are living within their own definition of the values, and the value, that you were bringing forward. But they're doing it their way, they're doing it at scale, and independent from you. That is true success.
Tell me a little bit more about where Summit is today versus where it was in 2008, and where you're taking it. Obviously, I'm going to want to ask questions about the social responsibility part that you're doing, because you guys have been doing a ton as well. But where are we today versus where we were in 2008?
Jeff Rosenthal
Yeah. So Summit is a family of enterprises and foundations. I’ll end with the impact side and then we can expand out my personal work and Summit’s in these categories.
So Summit hosted its flagship events, Summit Series. There's Summit Powder Mountain, which is the community we've been talking about. During the pandemic, we launched something that we talked about building for years, which is something called Summit Junto. Junto was Ben Franklin's gathering for a mutual betterment outside of Philly, where public hospitals and volunteer fire departments come from. I imagine they had a fair amount of fun kicking it in the woods with their friends.
Alan Fleischmann
It was his version of salon dinners.
Jeff Rosenthal
Exactly. But what really emerges through things like this is forum. Forum, in our opinion, is a slept-on human technology — experiences and events at the dinner table, and you know, a whole other slew of things that we overlook in their power and their capacity to help you make change. Ultimately, we launched this network, which is almost like a modern day YPO. It's the six-person Leadership Council Advisory Boards. We built a great team and a great product, and, have hundreds and hundreds of members now that are in their groups.
And then we have Summit’s foundation. So we have the Summit Fellowship Program, which is really focused on up-and-coming social entrepreneurs, both for profit and nonprofit. It's very global, I'd say the vast majority of them are under 30 years old. They get the a whole fellowship program and access to Summit. Then we also have something called the Summit Impact Foundation, which functions like an accelerator on behalf of exceptional leaders in a given discipline. The idea being that we have this incredible platform and network of entrepreneurs and leaders. We help the leadership councils around a particular organization or leader in a field, be it the environment, or voting rights, or criminal justice policy reform. And then we help those organizations accomplish a few exponential outcomes and 105-minute favors over a two year period. The idea being that, we have sort of the seedling stage, the garden stage with our fellowship program, and then we have the, how do we sight and scope the bazooka of our platform to have the maximum impact on behalf of those that have the greatest capacity to lead change.
Outside of that I sit on the boards of Beyond Conflict and Street Soccer USA. I’m on the leadership council at Conservation International. But if I'm being honest, I direct most of my time and attention towards market-based solutions on behalf on behalf of the environment. So looking for things that are typically for-profit ventures that have the capacity to scale in food, power, ag, energy. And I think that there is a profit model to replace the extractive and the environmentally damaging. And without it, we frankly won't scale the solutions to the level that we need, in order to avoid the trouble that awaits us on the other side.
Alan Fleischmann
The problems that are created by humankind and the way you go about your life is that we got to figure out, with our own ingenuity and urgency, how we solve those problems that were created by humankind. And private industry, entrepreneurship, and creativity is the way to do it in an urgent way.
Jeff Rosenthal
Well, even if you believe policy is the solution, sentiment drives policy. So you need an exemplary example. You need an exceptional example of how you can approach one of these intractable issues — like the grid, like power generation, like sustainable agriculture and infrastructure in home improvement. There's all of these areas, these hundreds-of-billions-dollar industries that are going to continue to churn on in the same way that they have for the last 100 years unless there is a scalable solution on the other side. So, I think that you can affect positive change at small level, you can build a little business. But in order to really make no small plans, it requires a lot of people, a lot of time, a lot of wisdom, and a lot of action.
When you talk about us and me in particular being really practical, but really optimistic — that's our one-two punch, man. It's got to be a big enough dream to where great people are interested. And then you have to be willing to do the brick laying, coal shoveling that every single enterprise requires for longer than it should to actually see that thing come true.
Alan Fleischmann
I love that. You and I have had great conversations about something that you and I both share, an urgency to make capitalism work. We're not shy that we believe in the market. We believe in capitalism, we believe in entrepreneurship. But it has to have that social impact side of it in order to solve our biggest problems. And you’re right, policy matters. Byou need to have it come from the outside in rather than from the inside out if you want to make sure that it has support, and frankly, impact.
So you're big on that, that's a big part of why I think of you when I think, how do we make capitalism work. Am I right?
Jeff Rosenthal
I don't know, that's over my paygrade; I'm not smart enough to talk about the function of capitalism. I recognize that that's the fishbowl that I swim in. And I think sociologically, it affects us, whether or not we want it to. It’s just the this the world we're in today.
I think a great example that gets made fun of is TOMS Shoes. It's easy to be like, “oh TOMS, what did you really do? If you bought a pair of shoes, it gave a pair to a kid that may or may not have needed it. That's not a good way to build sustainable economies, just giving away a shoe. Now there's a shoemaker who's out of business.” Two things that I think — and this was so early on, this is foundational to us. There's organizations today that are changing the face of you know, electricity and energy production and agriculture. They're just incredible, incredible businesses. But the reason I mentioned TOMS is because it was kind of the first external identity brand that people could throw on themselves to communicate to another that they thought it was cool to care about other people. Whether or not that was like honest, whether or not they actually carried that out — it's not what they were into or what they actually did — it started to create a bit of a new scorecard for how we measure each other in our generation in our society. It wasn't like, “I'm going to post my private jet pic.” It was “I'm going to post a pic of me on a charity-well tour.” I think that it's a gateway drug. You can think of it as like the first thing to where now, you have people wanting to make sure that all of their investments are negatively screened and that they're investing only in things that have like the world impacts that they care about.
For the last 50 years. I'm pretty sure that number one owned stock is McDonald's. McDonald's didn't have a nonprofitable quarter for 30-plus years. That's a consumer sentiment, that's them providing a product the market wanted. I’ll tell you what, I guarantee you if we say “hey, we only want plant-based, organic farm-raised foods, we won't eat anything else anymore,” Walmart and McDonald's are going to be the organizations that sell the most of that stuff.
Long story short, I just think that the market responds to the wants and needs of people really quickly. And if you can shift sentiment, you can shift policy, you can shift behavior, you can provide the interest in the capital for the change that we need to see at the speed we need to see it. That's just that's just our little wave. I wouldn't say that we're gonna fix capitalism, Alan.
Alan Fleischmann
No, I hear you. But I think you are. When you bring these people together, I see great partnerships being forged, creative ideas being discussed and shared. Some ideas happen at Summit, for example, that wouldn't happen elsewhere. And the Summit Action Fund has a lot of really socially responsible investing as well. So there's something about all the things you're doing.
I spoke earlier about you being all about partnership. Talk to me about your three co-founders for a moment and that relationship. Because you're known — you Jeff, but also you as Summit — are known for forging enduring partnerships. But I don't think that would happen if that wasn't something that was proved at the at the founder level. Tell us a little bit about that and the book, because I want people to read the book.
Jeff Rosenthal
Absolutely. It's infinite game, man, we play the long game always. We're always trying to build lifelong relationships, and that's the priority. That's where our actions come from in those relationships.
Me and my Summit co-founders, we've never had anything come to a vote. We've literally never had to use our governance structure as a group of co-founders. We've always been able to get to consensus through healthy debate. On the way up, we really sharpen each other like swords. It was a real team sport, building Summit and building ourselves to arrive at the personal capacity to meet the needs of the time. Because we were on an exponential growth curve, we had to grow exponentially, and you couldn't let your friend, your co-founder, live with their excuses or live with their lack of development in a particular space.
So it was very much like our liberation is bound up together. There's great Beatles quotes there from John Lennon, “the dream you dream alone is only a dream. A dream you dream together is reality.” We got that early taste of success and we were like, “this is possible and we can do this. And we have to ride this as far as and as high as we can.” And frankly, we got so much pleasure and joy. The learning safari we've gotten to go on and the level of mentorship that we've gotten, it's just so profound and tremendous. Even when there were moments where we were offsides with one another in ways that aren't going to be cool. People screw up over 15 years, you're going to make mistakes, you're going to do things that you're sorry for. But you know, you have to be able to have forgiveness. You have to be able to stack and plow, in the sense.
I love the word compromise. It's a dirty word now, a dirty political word. But it's actually this tremendous accomplishment of humanity. You and I can vehemently disagree on something. But we can agree to something that's lightly disagreeable enough to both of us to where we can move forward to the next issue and continue to, you know, build on top of where we've been. So I think that always being open to compromise, always being open to you not having the answer… Just because you have strong conviction doesn't mean you're right. So we ultimately would acquiesce to the enthusiasm and passionate, informed knowledge of our partners. If somebody said, “hey, I'm willing to put my name on the line could this because I know that this is the way it should be.” Okay, I could be wrong here. You can be right.
A lot of this is why we wrote the book, Make No Small Plans. We were at our LA ’18 event and Ray Dalio spoke. We were hanging out with him after one of his talks and he was like, “guys, this event is great, you should write a book about it.” We're like, “that's very flattering, thank you. You're here to talk about your book Principles, which you built over a lifetime of being an absolute thought leader in your space and all spaces. We'll wait until we're at your stature to write our book.” He goes, “that's not true. You have principles that guide your decisions. And those principles are filled with wisdom. And people could really be benefited by those principles.” His whole idea is there’s a first layer of decision making that you have, and if you reflect on why you made that decision, you can almost elevate to second-level decision making. Because you don't have to think about any of the things that you've done before and the reasons that you've done them.
So it was just inspiring for us. We said, “you know what? We think there's some truth to that.” And we essentially just told our story, from the founding of Summit to buying Powder Mountain, but there's some 30-odd vignettes in the book. First the wisdom, the quote that we kind of live by. And then the stories that we thought that were most pertinent to that wisdom. So if you're in the market for such brilliantly written, wise, fun reads like Make No Small Plans, maybe it might be good.
Alan Fleischmann
It's a great book, because it really does give you a sense of adventure, wisdom, and camaraderie. Again, I'm big on the fact that you're all about bringing people together in uncommon ways, and you guys are living it out. You are four distinct individuals doing different things, but have a common mission that builds Summit. That's really amazing to see and to watch. The book is filled with wisdom, actually.
Jeff Rosenthal
Thank you. We also wrote it more in narrative form. We wanted to make it more like a Ben Mezrich or Michael Lewis book than a traditional business book.
Alan Fleischmann
Was it hard to write when you have four authors coming together?
Jeff Rosenthal
Well, we had a great writer and editor — we had a great team, a number of people that helped us, but Cal Fussman, who wrote What I've Learned for Esquire for all those years, really helped us executive edit the book. Ryan Holiday helped us a lot with the early drafts, and Georgia Frances King was an incredible editor on the book. Again, this is the secret to our success: we get people who are better than us at doing the thing to hold our hands through the process. It's written in the third person, but it shares all four of our experiences and perspectives through these times.
And it was just so fun, because this is a long time ago for us. It's been eight years, nine years, ten years for the stories that we're reliving and talking about. There's perspectives that we didn't have, or experiences that happened to our co-founders that we weren't privy to until we had to relive these moments. And it's such an intimate thing, it's something that's going to live on beyond you, in most cases. Whether it's music, or a book, or a film, or whatever.
Events are very ephemeral, we do it and then it's gone. So it gives you a little bit more leeway, a little bit more flexibility for mistakes. Whereas things like books, they take on a serious posture by the end. You think “oh whatever, it's okay, it's all good.” Then when you're faced with… We delayed the publishing, actually, and rewrote the book to many degrees, just because we ultimately felt that it wasn't good enough. So it took us two years to write the book. But that's also our process; we will typically do something, kind of fumble our way through the dark as first timers, and then be like, “okay, here's all the things that we screwed up, here's all the best people.” I's maybe a little more expensive and it takes more time, but at least we get it right and we can keep a wide breadth of interests.
Alan Fleischmann
That's really cool. Most people who write a book also use it as a time to reflect and then think about their next chapter. Was it that? Did you find that as you were thinking about tomorrow, you were thinking differently because of the process of writing the book? And do you find that your partners or co-founders of Summit are thinking differently or the same themselves?
Jeff Rosenthal
No, I don't think that. Because we were in the middle of the pandemic, of shifting our business, of launching new businesses. We're still building our careers and building our companies, we're not in the reflect on the next chapter phase. So you know, it was kind of a crazy time to write this book.
But I'll tell you what it did do. It made us more comfortable through like the big wave. The world changed, again. We started Summit in 2008, it was the Great Recession, right? So we've had this happen a number of times over our journey, where we had what we would call Final Fridays. A Final Friday is the last day you can send the money to the bank, or to the account, or to the debt holder — whatever it is — because the banks aren't open on the weekend. And then the next week, it's the next week, the game is over. So we've stared down intractable, unsolvable problems enough times now to where we have some grit and we feel like we can figure it out. Because if we think we can, we can, and if we thought we couldn't, we wouldn't. And that might sound a little ‘the secret’ to you, but you know, check the tape: we made it work a number of times because we are humble enough to know that we are not fantastic CEOs. We don't have the answers to everything, we don't trust our own biases. The great gift of Summit, you know, is this multi-generational, interdisciplinary, diverse group of thought leaders. It did take us some time to realize that that was also our greatest resource for building Summit.
So that was the big lesson from the book. It was like, “look, we did it before a bunch of times. It seemed like the music was gonna stop, and it didn't. This is just another one of those moments where you have to be ingenious, you have to have ingenuity, you have to find the solutions.”
The way that we would do it back in the day is very different than the way we do it today. We used to just throw out crazy ideas until one was not that crazy and actually achievable, and then we'd work backwards. Now we're trying to come from wise places. We have years to reflect on. For instance, Junto — we thought about building that business for four years and it took the pandemic to sort of force us into action. That's not like, ‘ready, fire, aim,’ which is where we were in 2009. That's very much thoughtfully planned, capitalize, recruit great people, build the program. We now aren't naive, we aren't going to think that we're going to throw together a company with some paperclip and bubblegum.
Frankly, when you're a startup and you’re doing something really novel and new, you get more leeway. when you're a 15-year-old organization and you're like a baby institution, like us, that has come and gone. You don't get that permission anymore to screw up little things or to have an eight out of ten product. People expect a ten out of ten product from you.
Alan Fleischmann
You're listening to “Leadership Matters” on SiriusXM and at leadershipmattersshow.com. This is your host, Alan Fleischmann. I'm here with my good friend, Jeff Rosenthal, and we're talking about his journey. We're also talking about his book that he co-wrote with his co-founders of Summit, called Make No Small Plans.
Jeff, that that book tells the history of Summit. It's very personal. It talks to me, as a guide to young entrepreneurs, young leaders in particular. What would you hope readers would get out of it from a key lessons point of view? Or even just in general.
What I love about you, you're very humble, but you have a lot of wisdom. You've observed people, you’re beautiful at observing people. What are the chock-full of kind of wisdoms that you would share? Because the people who are listening to this show, we've got CEOs, we've got investors, we've got inventors, we've got aspiring leaders. All of whom really love to learn from those who come on the show.
Jeff Rosenthal
A few that come to mind. And we literally name the chapters in the book — even if you don't read the book, you can look at the chapters and know pretty much 90% of the things that we know. But one that comes to mind, just because it’s leadership: I like saying that leaders don't have followers, leaders create other leaders. That's indicative of our philosophy and how we handle our relationships with the Summit community, but also how we think about the Summit team. Nothing would make us happier than working for our direct reports. That's on them, not on us. Where it's on us is, can we help them grow? Can we encourage them to feel that ownership over what we are doing and building? Our dream is to have more talented people than us grabbing the reins of all the things so we can continue to grow and do new things for the organization.
One of the things early on was shared with me by a mentor and friend of mine named Michael Hebb — who in many ways created the pop-up restaurant as we know it today, the underground restaurant movement out of Portland. The first time we met at Blade in the Conversation, he was like, “hey man, do you keep it real?” I was like, “Yeah, of course, I keep it real.” He was like, “don't do that. Everybody keeps it real. What you have to do is keep it surreal and go just a bit beyond everybody else's imagination.” And that is genius, because then you're talking about being delightful and surprising. And you can really consecrate your experiences. You can use narrative, ritual, and experience to create a different texture of reality. So that person remembers what you provided for them in a different way than they ever would have.
When people relax, when their parasympathetic nervous system relaxes, they're more open to new relationships and deeper friendships. They're more open to new information. And so, you can really start talking across the aisle on different issues, if you can get people into a milieu, a vibe, or a state where we don't feel attacked, where we do feel comfortable and relaxed. I'd say that we're so ridiculously lucky because of the people who invested their time, their energy, and their relationships in us. We never found fanboy-ed the big timers and we never snubbed the startups; we always had mutual respect in both directions from wherever our position was at Summit. And a lot of those people that were earlier in their careers became absolute luminaries, and a lot of those luminaries got deep joy out of helping us. If we were just like, “everything's cool Alan, let's just be friends!” You'd be like, “that's pretty boring for me, Jeff. I actually want to know what your challenges are so I can help you with them.” That's what mentorship is.
So I think many of us think about relationships like it's quid pro quo, there's an exchange. You help me, then I owe you. But in reality, if you help me now, you're more invested in my success than you were before you did me the favor. So actually, you're now committed baby — you're gonna help me more! So long as you hold in respect and deeply appreciate those relationships, you cherish them, then you're not going to take advantage of them, you're not going to utilize them for your own upside without telling that mentor, that person. And if you hold them in that way, then they'll always be able to help you achieve whatever it is that you're trying to get done.
Alan Fleischmann
That's great. How much does culture play a role in this? Ultimately, that's what you're creating.
Jeff Rosenthal
Culture is everything, man. I mean, it's almost an overused word at this point. But I can answer that in two ways. One, if you employ all white dudes, if all you have is white men, you’re 90% white men in your company, what people of color or women want to join that culture? The game is already over, you are who you are and everything else is an approximation. You can throw out messages and try to communicate, but if you're not made up of the people that you're looking to represent on behalf of, it's just never gonna work.
And then, the most foundational advice we got, maybe a good one to go out on, was from Tony Hsieh, who passed away last year, the founder and CEO of Zappos. He was a huge patron, supporter, friend, and mentor of ours. When we threw our White House event in 2009, after the event, we threw a little dinner thing that night. He came over to us and was like, “Hey, guys, are there people here who you wouldn't be friends with if they didn't have any professional or personal success? Are there people here that you wouldn't have to your parents’ house for dinner if they weren't personally successful?” We're like, “yeah, of course. There's a couple of people here that we don't exactly find agreeable. But that's not what our mandate was. The White House asked us to bring the top young entrepreneurs in the nation who are changing, blah, blah, blah.” And he's like, “Yeah, well, they can't come anymore. Because if you're building a community, culture is your most important asset. And you need to only be made up of the people that fit your culture.” Here we are in 2022, this is 13 years ago. So we were 24, 23 years old and this was mind-blowing knowledge. We had never heard any of this language before and we were up all that night — we were literally up until sunrise — and we came up with a criteria for Summit that night based on that feedback. Which is, one: are these people innovators in their field, regardless of their discipline? And two: are they kind, open-minded people, regardless of personal or professional success? And these innocuous, kind of loose, optimistic criteria have led to this culture of community that I think is singular in a generation.
Alan Fleischmann
That's amazing. So in our last couple of minutes together, what is it about Jeff Rosenthal you'd want people to know? Because I find you to be really truly one of the one of these great, humble, thoughtful people that I get to call my friend. What is it that I'm not asking you that I should ask about you, or about Summit, or about what you're up to, or what you're worried about, or what you're really focused on? What should we tell our listeners?
Jeff Rosenthal
I don't know how to answer that, Alan. I'm not I'm not really a spotlight seeker — here I am on your podcast saying that, but…
Alan Fleischmann
But you're not, I’ve been asking you for a while to come on this show. I took advantage of the moment knowing that you four wrote a book to get you on. But I really want people to know to get a sense of who you are, Jeff, not just one of four in Summit.
Jeff Rosenthal
We're an hour into a podcast, you probably have a bit of an idea as to who I am at this point.
Ultimately, it's the simple things in life that bring you the most pleasure. Maybe it’s a little boring, but it's family, self-care, adventure, and experiences. That's what I'm optimizing for. I am lucky enough to have these for-profit and nonprofit platforms to help make the small difference that me and my friends will make in the world while we're here. And that is just this unbelievable pleasure. I certainly wake up some days, lots of days, like anybody, and… To know that and then to live that are two totally different things. But when forced to reflect, I mean, we just feel like we're the luckiest people. I feel like I am remarkably blessed to be able to do what I do and to make a living doing it. It's 1pm on a Tuesday and I'm not in a boardroom, I'm here with you. I'm very happy and appreciative for both my life decisions and the people who have invested in me who have empowered this lifestyle.
What I will say is, if you're sort of afflicted by creativity like I am — I have to create, I have to build stuff. The most anxiety I get is if I try to just sit on a beach for a couple of days, it's just a little hard for me. Even on vacation, I want to do a bunch of stuff. So. So I think that there are people who are out there in the world who are totally happy watching six hours of football on a Sunday. There is zen to that I actually admire and frankly, am a bit jealous of. My mind is kind of always going, I'm always wanting to build. But you know, if that is your setting, then being an entrepreneur like I am is just so much fun, because of the challenge. But it's stressful, it's all stressful, it's all difficult. And that's just life.
I love the Hagakure, the 17th-century book of the samurai — recently, that is the new philosophy book I've been reading. One of the things it says is that death is the end of shame. What it means by that is, if you're living on your edge and you're constantly growing, you're trying to elevate, then you're constantly experiencing shame, because you're trying to find the next thing that you're not good at. And that's kind of why I am humble. I measure myself based on what I do, not what I say and not what it looks like, not the esteem of my peers. I know what I did today, yesterday, and tomorrow. And if you can be happy with yourself, when you’re eye to eye, brushing your teeth at the end of the night, you're a lucky person. And if you get to do something that you actually enjoy, you're an immensely lucky person.
When I think about your listeners, I don't think that they should be thinking about me at all. I think they should be thinking about you know them. I just hope that, after an hour of listening to you and me talk, that there is something valuable in there that they can take with them and help build your own awesome life, because that's really what matters.
Alan Fleischmann
That's really brilliant, wonderful, and thoughtful. I'll tell you, we all struggle to live a life of confidence and humility, if we are seeking that. The only way that one can accomplish that is if they know what they're grateful for. It's gratitude that creates humility. I think of you as somebody who is insatiably curious, loving to be with people, loving to learn, and somebody who is grateful.
I'm grateful for our friendship. I'm grateful for the time we had today, and on behalf of “Leadership Matters” and leadershipmattersshow.com, I just want to say thank you, Jeff, for what you're doing. I think people should check out Summit. They should go to your gatherings, meet interesting people, learn a lot, and with us, maybe, change today's norms to do some great things in the world. So thank you.
Jeff Rosenthal
Thank you, and thanks for listening.
Alan Fleischmann
I love our conversations. Look for to have you back on. Thanks so much.