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[Book Summary] Make No Small Plans: Lessons on Thinking Big, Chasing Dreams, and Building Community

Make No Small Plans (2022) is the inside story of how a group of young entrepreneurs created one of the world’s most exciting platforms for global events and conferences – the Summit Series. This isn’t just a chance for them to recount their company’s history, though. Packed with actionable takeaways and business wisdom, this is a book designed to inspire readers on their own entrepreneurial journeys.

[Book Summary] Make No Small Plans: Lessons on Thinking Big, Chasing Dreams, and Building Community

Content Summary

Genres
Introduction: What’s in it for me? Insights into the Summit story.
Passion sees you over the line when the going gets tough.
Follow your authentic interests but hedge your bets.
Question existing ways of doing things and you might just hit upon a great idea.
If you want to build something memorable, keep it surreal.
Keep an open mind and you might just win big.
Final summary
About the author
Table of Contents
Overview
Review/Endorsements/Praise/Award
Video and Podcast
Read an Excerpt/PDF Preview

Genres

Entrepreneurship, Career Success, Religion, Spirituality, Personal Success, Motivational Growth, Women’s Personal Spiritual Growth

Introduction: Insights into the Summit story.

If you’ve been following modern entrepreneurship, tech, and business culture, you’ve probably heard of Summit.

Summit started with an idea: great things happen when you bring people together and get them talking. That’s not a new idea – it’s why global movers and shakers head to places like Davos and Aspen, after all.

But the guests at those kinds of events are typically already established. They’re presidents and Pulitzer prize winners or the CEOs and CFOs of giant corporations.

What about the next generation, though – the people building the apps and start-ups set to revolutionize tomorrow’s world? What if you brought them together and got them talking?

In 2008, four 20-something entrepreneurs with little hands-on experience and just two college degrees between them decided to find out. Their book, Make No Small Plans, is the story of what happened next.

The short version is that they built Summit, an event company that has become known as a kind of Davos for young entrepreneurs and a hothouse for up-and-coming talent.

Summit’s first iteration, a ski trip in Utah, was a far cry from the kind of events it hosts today. Back then, there were just 19 guests in a poky rented house with shared bedrooms. The beer ran out within half an hour and the shoestring budget barely covered the skiing equipment. But it didn’t matter.

Once those guests got to talking, sparks started flying. They traded ideas, hatched deals, and made plans for the future. Most importantly, they forged lifelong friendships.

After Utah, Summit snowballed. Today, it hosts events all over the world and its list of guest speakers includes the likes of Jeff Bezos, Richard Branson, Al Gore, and many other recognizable names. The scale of the Summit operation may have changed, but the company’s values remain the same. As the founders’ manifesto puts it, “We believe that the more great people you meet, the more great people you will meet.”

In this summary, we’re going to learn about the story and spirit of Summit. We’re not going to try to tell you the long version – that’s best left to the authors of Make No Small Plans. Instead, we’ll be zooming in and focusing on five snapshots that capture the philosophy, ideas, and values of these remarkable entrepreneurs.

Along the way, you’ll also learn

  • why no idea should go unspoken;
  • how to build meaningful business relationships; and
  • why it pays to keep things surreal.

Passion sees you over the line when the going gets tough.

People say, do something you love and you’ll never work a day in your life. It’s an idea that’s been knocking around so long it’s virtually become conventional wisdom.

Thing is, though, it’s not quite right.

The thinking here is that the things you care about – call them passions, or hobbies – are easy because you want to do them. Work, by contrast, is a chore. A slog. Something you have to do which you’d rather not. Time flies when you’re having fun but the office clock turns unbearably slowly. If doing something you loved also earned you money, it follows, it wouldn’t really be work.

But there’s another way of looking at things. The thing about passion projects is that they make you want to keep going deeper. You keep discovering more complexity. More room for improvement. You also become more critical and more attuned to shortcomings. In short, they turn you into a perfectionist.

It’s the same whatever the activity. Tennis. Playing the guitar. Writing code. You want to get better, but improvement is painful. Playing scales a thousand times sucks. Spending hours practicing your backhand is a chore. Building the 100th basic website is boring.

But you persevere. Put in the hard yards. Complete the drills. It’s precisely because you care that you’re capable of doing the work. Put differently, if you do something you love, you’ll work every single day of your life. And that’s a good thing! Because you’ll be doing something that matters. That expresses your values. That moves you toward your authentic goals.

It’s not a question of work versus passion, then – that’s a false dichotomy. It’s care and interest. If you care, you’ll do the work; if it connects with who you are, if it interests you, the hard and boring parts of the process mean something. That’s what sees you through. That’s what keeps you pushing.

This idea isn’t neatly packaged in Make No Small Plans – it isn’t given a chapter or section of its own. But it shines through on every page and in every story the authors tell. Of course, on its own, that caring isn’t enough for success – there’s so much more that goes into something as complex and big as building a global company. But it’s absolutely foundational. Everything else gets built on top of this commitment.

Follow your authentic interests but hedge your bets.

Let’s rewind to 2008. The economy is crashing and the future is uncertain. Elliott, one of Summit’s founders, is in college. He’s not happy, though. Something is missing.

One day, while walking to campus, he finds himself caught up in a large crowd of students. Everyone is streaming in the same direction, toward the library, to read the same textbooks and study the same problems. Problems last year’s students solved. All so they can compete for the same jobs in the same labor market that’s being wrecked by the greatest recession since the ’30s. For Elliott, it doesn’t add up.

He doesn’t want to do that. He wants to work on his own problems, not his professors’. He doesn’t want to study – he wants to build something. In short, he’s just discovered something important about himself: a sense of where his authentic interests lie and what he wants to do with his life.

The word authenticity can sound like a big and intimidating, existential kind of thing. That’s because we often think of it in all-or-nothing terms: being authentic or being inauthentic. But you don’t have to go all in right away. Take it from Elliott.

He’s realized he wants to set and solve his own problems. To work for himself. To be an entrepreneur. His first thought? Take the plunge. Quit college.

His dad, luckily, is a sensible guy. Down to earth. Practical. Here’s what he says. There are risks, and then there are risks. The question to think about is how far you can fall. Dropping out of college and spending all your savings is very risky. If things don’t pan out, you’ll be in a tough situation that’s hard to get out of. So what if you spend some of your savings and stay in college while working on what you really care about? If it doesn’t work out, you’ll have a bruised ego but you’ll still have options and half your savings. Same reward, different risks. Simply put, don’t put all your eggs in one basket.

What was Elliott’s response? He listened. He didn’t drop out of college. He started selling ads in an online newsletter in his spare time. He didn’t spend all his savings. And he didn’t try to persuade his family to remortgage the house to support his business idea. And that, too, is part of the Summit story. It was the cold calls he placed from his college dorm room that taught him the skills he’d need to launch the company.

So here’s the lesson: acting authentically doesn’t mean being reckless. You’re not charging headlong into the unknown – you’re slowly pushing open doors to new opportunities.

That process begins with a single question: What am I interested in? Sometimes, the answer will present itself serendipitously – it just hits you one day, like it did Elliott. But you can also be more deliberate about it. Sit with that question a while and then write your answers down. Maybe it’s cooking, or fitness, or finance, or learning a language. And then? Well, you make time to do those things. You start cooking. Take that class. Get that certificate. Enroll in that course.

So many big journeys start with this shift from a passive wish to active engagement. But remember: it’s not all or nothing. Don’t make small plans, but do start small!

Question existing ways of doing things and you might just hit upon a great idea.

Entrepreneurship isn’t glamorous – especially when you’re cold calling prospective clients from your childhood bedroom. Most of all, it can be lonely.

There were tons of other young entrepreneurs out there, but Summit’s future founders found it hard to connect with them. Back in the late 2000s, the only real bet was to attend networking events.

These events were brutal, though. For a couple of hours, you’d be crammed into the brightly lit lobby of a downtown hotel with hundreds of people desperate to seize this opportunity to make connections. It was loud. It was stuffy. It was chaotic. It wasn’t a get-together. It was a cattle market.

It wasn’t just that there wasn’t time or space for interesting conversations, though. These events seemed to actively encourage soul-crushing interactions. It was an environment designed for that guy who’s always selling something; who’s always pushing his agenda. The guy who’s already surveying the room for his next target while failing to listen to the person in front of him. Who treats others as means to his ends.

Everything was transactional and rooted in short-term thinking. It was about what you can do for me right now, or tomorrow, or next week. But the best networkers are the kind of people who build long-term relationships with people they care about. They understand that relationships need to be nurtured – you have to put work and practice and time into them before they bear fruit.

For the Summit founders, this way of looking at things seemed intuitive – even obvious. But that posed an interesting question. If the secret to building great business relationships was hardly a mystery, why wasn’t there some kind of forum that encouraged that behavior? A space in which better, deeper, more interesting conversations could be held? A place in which entrepreneurs could actually meet each other?

It was that question which launched Summit Series.

The timing was right, too. The first buds of the new digital economy were sprouting from the rubble left behind by the crash of 2008. With the app store, you could build anything. New brands were springing up and reimagining the way everything was sold, from mattresses to shoes to vacuum cleaners.

But all these entrepreneurs were like individual islands. Together, they formed a kind of archipelago, but there was no bridge connecting them. And that’s where Summit came in.

Here was the idea: bring as many of these entrepreneurs as possible together in one place and get them talking. Not just for a few hours. And not in a stuffy hotel lobby. Somewhere nice. Someplace where real conversations could unfold. And that’s how it started. Elliott booked a house near Utah’s ski slopes and started cold-calling potential sponsors and interesting young entrepreneurs he’d read about. In the end, 19 people agreed to come on an all-expenses three-day ski trip.

It was the start of something big. And it all started by questioning the status quo.

If you want to build something memorable, keep it surreal.

Okay, so we’ve talked a bit about following your passions, balancing your authenticity with good sense, and starting small, being brave enough to break tradition and do things your way . . . what’s next?

For Summit’s founders, whether they’re hosting an event with fewer than 20 or more than 2,000 guests – certain rules always apply.

First, the guests. Who do you invite? The Summit take is that status is irrelevant – you don’t have to be wealthy or occupy a prestigious position to be an interesting person. What really matters is passion.

You start by asking: Is this person doing work they love? The second question is even simpler: Are they nice? That’s it. If someone ticks both boxes, they pass what’s known as the Airport Test – they’re someone you’d happily spend four hours with if your flight was delayed.

Those were the questions Summit’s founders asked when they organized that ski trip to Utah, and they’re the questions they still ask when they send out invites to events today.

But interesting and nice guests alone don’t make an event. There’s another factor in play.

One evening – this was around 2010 – the founders were having dinner with an eccentric chef in Los Angeles. He’d pioneered the city’s pop-up restaurant scene and was the star of its underground food movement. His stunts included organizing dinners by the side of highways, or on cliffs overlooking the ocean.

He’d heard about Summit – word had gotten around after Utah and a couple of follow-up events. Thing is, he told the founders, you’re keeping it real when what you really need to do is keep it surreal. It was his way of saying that Summit was a bit boring. That it needed to go up a gear or two.

He was right. And that brings us to that second factor – atmosphere. The staging. The environment. The table by the side of the highway that reframes your dish of tortellini. The thing that makes the event, well, surreal. Memorable. Immersive.

So what if you hired an entire cruise ship, packed it with over a thousand interesting guests, and sailed it around the Bahamas for three days? In 2011, Summit did precisely that. And suddenly everything came together. It was a unique experience with amazing people.

Think back to those stuffy, overlit hotel lobbies and then imagine the exact opposite – that’s what Summit at Sea was. There were meals cooked by young chefs. Live music on multiple decks. Intimate corners with sheepskin rugs for conversations. Meditation sessions. Conferences on everything from cryptocurrency to conflict resolution. Bars, pools, DJs. It was impossible to feel bored.

After 2011, Summit never looked back. Events became larger, more extravagant, and even more surreal. It’s a recipe that works. Tens of thousands of people have attended their events. More importantly, they’ve built lasting relationships. Take just a couple of examples. Qwiki, an iPhone video-sharing app that was sold to Yahoo for $50 million, was born at a Summit event. The $100 million wristwatch health-tracker company Basis secured its first round of major investment at another event.

Great things happen when you bring the right people together and get them talking in the right environment.

Keep an open mind and you might just win big.

So, Summit may have started with one great groundbreaking idea . . . but how can a company stand the test of time and stay innovative? Summit’s answer is that you foster a culture in which no idea goes unspoken. Let’s break that down.

Ideas are egalitarian. Interns can have great ideas and CEOs can have terrible ideas. It can go the other way too, of course. Sometimes relative inexperience and experience do matter. Point is, a great idea can come from anywhere, and the status of the person proposing it isn’t a reliable indicator of its worth.

So that’s the first marker of a culture that’s open to ideas: everyone gets a fair hearing. The second marker is that there’s an emphasis on generating lots of ideas. Put differently, it’s not just that anyone can put forward an idea – it’s that there’s an expectation that everyone will.

That’s because quantity makes quality. It’s only by getting it all out there that you get to the good stuff. If an idea isn’t right, you move on. No harm, no foul. You don’t have to commit to a bad idea just because you’ve given it a hearing, but the more bad ideas you hear the more likely you are to find the good ones.

On one level, hiring an entire cruise ship for more than a million dollars was a crazy idea. But it’s what put Summit over the top. That’s where that culture makes a difference. When you’re willing to engage with crazy-sounding ideas, you often find out that they’re actually workable.

Take another wild idea – getting Jeff Bezos to appear at a Summit event without blowing the company’s entire annual budget on speaking fees. It just doesn’t sound doable – this is one of the world’s richest and most in-demand men, after all. Okay, sure, but let’s give the idea a fair hearing.

What is a speaking fee anyway? Well, it’s a benefit – a remuneration for someone’s time and energy. But does it have to take the form of money? The more they thought about it, the less sure Summit’s founders were that it did. Elliott, for example, remembered a deal he’d struck with a limousine service years earlier. The company wanted to place ads in his newsletter, but couldn’t afford to. So they came to a different arrangement: they got the ads and Elliott got to use their limousines to drive to meetings.

There’d been similar deals with bands who’d performed at Summit events, too. But what can you offer a man who has it all? The answer was a platform.

This was 2016. Bezos had become a household name, but people didn’t really know his story. Who was he? Where had he come from? What were his values? So that’s what Summit offered him: a chance to tell that story to a live audience of 2,500 as well as the millions of people who’d later watch a recording of the interview. That, to him, was a unique benefit that was far, far more valuable than a speaker’s fee.

The moral of the story? Make big plans and give crazy ideas a hearing. You never know – they might just work out.

Final Summary

We’ve just gone through the summary to Make No Small Plans, by Elliott Bisnow, Jeff Rosenthal, Jeremy Schwartz, and Brett Leve.

So what, if nothing else, should you remember from this today?

Summit’s philosophy is that interesting things happen when interesting people get together and start talking. And that’s really at the heart of what the company does: it provides a forum for people to collaborate on big plans. And it’s also how Summit itself works. It’s the founders’ commitment to nurturing ideas, creative problem solving, and – above all – collaboration that’s made Summit so successful.

If you’re feeling a bit uninspired or at a dead end, consider going to a conference, finding or founding a group of people interested in trading ideas, and seeking out those that can open your mind to new ways of thinking.

About the author

Elliott Bisnow, Brett Leve, Jeff Rosenthal, and Jeremy Schwartz are the founders of Summit, a global company that has produced more than 250 events over the last decade, and the co-owners of Powder Mountain, the largest ski resort in the United States. They were early investors in startups including Uber and Warby Parker, and they are actively involved with Conservation International, Beyond Conflict, and the Anti-Recidivism Coalition. All four are sought-after speakers and have been featured in The New York Times, The Wall Street Journal, The Economist, Bloomberg Businessweek, Time, and Fast Company.

Elliott Bisnow, Brett Leve, Jeff Rosenthal, and Jeremy Schwartz

Table of Contents

Title Page
Copyright
Epigraph
Foreword by Jody Levy
Introduction
Chapter 1: There’s No Better Building Block Than Trust
Chapter 2: Your Reach Should Always Exceed Your Grasp
Chapter 3: Ready, Fire, Aim
Chapter 4: Authenticity Trumps Perfection
Chapter 5: Replace Your Weaknesses with a Partner’s Strengths
Chapter 6: Know Your Definition of Success
Chapter 7: If You Want to Go Fast, Go Alone. If You Want to Go Far, Go Together
Chapter 8: Reputations Are Earned by the Drop and Lost by the Bucket
Chapter 9: Opportunities Can Come from Anywhere
Chapter 10: Mystery Makes History
Chapter 11: Culture Steamrolls Strategy
Chapter 12: A Single Connection Can Be Exponential
Chapter 13: When You Know How to Listen, Everybody Is a Guru
Chapter 14: You Don’t Get Chances, You Take Them
Chapter 15: Fortune Favors the Bold
Chapter 16: Throw Off the Bowlines
Chapter 17: You Have Two Ears and Only One Mouth. Use Them in That Ratio
Chapter 18: Cult Classic, Not Bestseller
Chapter 19: Life Is a Giving Competition, and We Intend to Win
Chapter 20: Don’t Keep It Real, Keep It Surreal
Chapter 21: Don’t Worry About Making Mistakes When You’re Making History
Chapter 22: No Idea Should Go Unspoken
Chapter 23: Leaders Don’t Have ; Followers; Leaders Create Other Leaders
Chapter 24: Live the Brand
Chapter 25: Bite Off More Than You Can Chew. You Can Figure Out How to Chew Later
Chapter 26: Honor Thy Error as the Hidden Intention
Chapter 27: It Only Has to Happen Once to Be Remembered
Chapter 28: Change Your Point of View to Change Your Point of View
Chapter 29: The Art of Social Sculpture
Chapter 30: Spaceships Don’t Come Equipped with Rear-View Mirrors
Chapter 31: When You Have the Right Opportunity, It’s Always the Right Time
Chapter 32: It’s Not About the Idea. It’s About the Execution.
Chapter 33: Unite the Core to Move the Masses
Chapter 34: Become a Favor Economy Millionaire
Chapter 35: Find the Tipping Domino
Chapter 36: Pressure Makes Diamonds
Chapter 37: The Road to Success Is Always Under Construction
Epilogue
Dedication
Acknowledgments
Index
About the Authors

Overview

From the founders of the acclaimed Summit event series and community comes the story of their unconventional journey to business success and the hard lessons they learned along the way.

In 2008, with no event production experience and two college degrees between the four of them, Elliott Bisnow, Brett Leve, Jeff Rosenthal, and Jeremy Schwartz became business partners and set out to build a global events company. With passion and tenacity, they began cold calling as many inspiring company founders as they could and tried to convince them to attend their first event. In the beginning, only nineteen people said yes.

Since then, they have grown Summit into a global community with events all over the world, hosting luminaries including Jeff Bezos, Richard Branson, Shonda Rhimes, Brené Brown, Kendrick Lamar, and Al Gore. In 2013, the Summit founders—with help from their behind-the-scenes co-founder and partner Ryan Begelman—acquired Powder Mountain, the largest ski resort in the United States, with a dream of building a mountaintop town of the future.

In Make No Small Plans, they reveal the triumphs, mistakes, and cornerstone lessons from their journey, which began during the Great Recession and continues today. Alongside teachings from some of the most inspiring entrepreneurs of our time, the authors offer takeaways such as:

  • No idea should go unspoken.
  • Reputations are earned by the drop and lost by the bucket.
  • The road to success is always under construction.
  • Become a favor economy millionaire.

Entertaining and empowering, Make No Small Plans shows that anyone can think big and—with a thirst for knowledge, a talented team, and a little humility—accomplish the impossible.

Video and Podcast

Review/Endorsements/Praise/Award

“If you want to succeed as an entrepreneur, Make No Small Plans shows how the Summit team did it.” – Ray Dalio, #1 New York Times bestselling author of Principles for Dealing with the Changing World Order

“[Make No Small Plans] neatly crystallizes the teachings and takeaways—basic truths—from the past 15 years of Summiteering: ‘authenticity trumps perfection,’ ‘no idea should go unspoken,’ ‘opportunities can come from anywhere,’ and ‘when you know how to listen, everybody is a guru.’” – Forbes

“Making big dreams come true starts with learning the principles of those who did it before you. If you want to succeed as an entrepreneur, Make No Small Plans shows how the Summit team did it.” – Ray Dalio

“Elliott, Jeff, Brett, and Jeremy have a singular capacity to bring together leaders and inspire them to do more. I’m grateful that they have paused long enough to put their story, and their lessons, in writing.” – Christina Sass

“Summit provides a unique opportunity for thought leaders from all sectors to come together and exchange ideas to innovate and solve pressing global challenges.” – Al Gore

“I had a great time at Summit. The people and conversation that took place there were inspiring.” – Kendrick Lamar

“Summit changed my life, expanded my thinking, and made me believe in what’s possible. Reading Make No Small Plans will do the same for you. If you’re ready to go after your biggest dreams with all you’ve got, you owe it to yourself to read this book.” – Alex Banayan

Read an Excerpt/PDF Preview

THE WORLD DOESN’T CHANGE ONE PERSON AT A TIME. IT CHANGES AS NETWORKS OF RELATIONSHIPS FORM AMONG PEOPLE WHO DISCOVER THEY SHARE A COMMON CAUSE AND VISION OF WHAT’S POSSIBLE. THIS IS GOOD NEWS FOR THOSE OF US INTENT ON CHANGING THE WORLD AND CREATING A POSITIVE FUTURE. – MARGARET WHEATLEY

FOREWORD

When Elliott, Jeff, Brett, and Jeremy asked me to support Summit, which quickly and naturally turned into a CEO and partnership commitment, I first asked them what their underlying mission had been for the last decade. As a long-standing Summit community member and a multi-hyphenate company founder, maker, and artist, I’d long valued Summit for the camaraderie and community I found at their events—but I was never clear on what they were trying to achieve behind it all.

“Make No Small Plans,” they said.

“But why?” I asked, beginning to apply design thinking to a thirteen-year-old early-stage start-up.

“Because life is precious, and it should be dedicated to doing something meaningful.”

And that, I realized, is what the members of the Summit community have in common: the insatiable desire to create and connect so that we can make an impact on ourselves and on generations to come. Because those are the type of people we are. We work hard and play harder. We want to know that our spirit can ripple long after we’re gone. And we often feel like outsiders, looking for others who work as hard, who care as much, and who take big ideas and turn them into real things in the world.

This book is the story of four friends with a bold vision, who held a belief that was being defined as it was being brought to life. It still is to this day. It will be for decades to come. Such is life for the ever-evolving entrepreneur.

Along the way, Elliott, Jeff, Brett, and Jeremy share their adventures, their mistakes, their discovery of their passion and purpose. The process of getting here was full of humility and heartbreak, success and failure, and all of the life lessons that fill the spaces between. Summit’s story to date is also one of true “maker mind” and the ways human creativity can express itself through the artistic medium of business—my favorite medium of all.

I invite you to enjoy this ride, but more than anything, to see how innately human this story is. I hope you are inspired by the courage it took to get weird, the trust it took to take every leap, the risks barely averted at every turn.

I also invite everyone reading these pages to bring your idea to the surface. To find that part of yourself that will become the conduit of your own maker journey. To reach that place of excitement where you hit your flow and surrender to the people, places, and unexpected things that are drawn toward you and your purpose. Like Elliott, Jeff, Brett, and Jeremy, you can become a force to invent new things that will impact the world around us. I invite you to Make No Small Plans…so that you, too, can live your biggest life!

—Jody Levy, global director and CEO, Summit

Spring 2021

INTRODUCTION

We’ve all been told that big ideas are impossible. Start your sentence with “I know this sounds crazy, but I was thinking…” and you’ll be cut off before you can even explain your vision and why it’s revolutionary.

The purity of our dreams gets corrupted when it meets the reality of other people’s experiences. “It’s not going to work,” they say. “It’s not the right time.” “We don’t have the money.” “Somebody else could do it better.” And if it’s not someone else shooting you down, we often do it to ourselves, dismissing our own ideas before even uttering them out loud. And yet most great businesses, products, and causes were deemed completely absurd and impractical notions at the outset.

We’re here to tell you that there’s never a bad time for a crazy idea. But there’s also never a good time to start a business; we certainly didn’t begin ours during one.

Summit Series was originally a conference series and a community of young, ambitious thinkers trying to begin their professional lives in the aftermath of the global financial crisis, both burdened by the instability of this new world and blessed with the opportunity to create something new in its wake. Over the coming decade, it would develop into a multi-disciplinary festival, attracting international leaders, pioneering entrepreneurs, and creative luminaries. But at the start, everyone told us we were crazy to dream that big.

In our early twenties, we lived in a house belonging to one of our grandmothers in a Florida retirement community, sleeping in bunk beds and on couches. Later that year, we were the first organization to connect a group of entrepreneurs to the Obama administration during a White House event focused on policy changes to support start-up founders. By our mid-twenties, we had chartered a fourteen-story ocean liner—the youngest people in history to do so, we’d later learn—and created our own floating city for a weekend. Before we turned thirty, we had bought North America’s largest ski resort, Powder Mountain, on ten thousand acres of pristine Utah wilderness, and began turning it into a permanent home for our community.

How did four young dreamers with zero relationships, zero experience, and two college degrees between the four of us quickly rise to hosting luminaries like Richard Branson and Quincy Jones? We are not billionaires. We hold no patents. We are not geniuses or household names. We are simply four friends: Elliott, Jeff, Brett, and Jeremy.

Some people are destined to invent. To invest. To run for office. We have always had the burning desire to create impactful gatherings and build a community of entrepreneurs, creatives, and makers. We wanted to introduce them to new ideas. To inspire them. To help them succeed.

Historically, if you were a young writer or editor after World War I, you knew you could find Ernest Hemingway, F. Scott Fitzgerald, James Joyce, and Gertrude Stein at the Ritz in Paris. If you were a young musician in the sixties, you knew that Diana Ross, Stevie Wonder, and Marvin Gaye were setting the world ablaze from Motown’s offices on West Grand Boulevard in Detroit. And if you were a young entrepreneur in the decade of innovation that emerged from the rubble left by the greatest recession in a generation, you knew that the people at the heart of that revolution could be found at Summit Series.

The strength of our organization stems not from its four founders but from the hands of the remarkable community, connected by a common, insatiable desire to create, to share, and to nourish their best selves. Summit Series simply gives them a place to gather, collaborate with one another, and expand their minds, ideas, and friendships.

Over the years, those creators included everyone from Amazon’s Jeff Bezos to actor and founder of the billion-dollar Honest Company, Jessica Alba. Hundreds of thought leaders have imparted their wisdom, such as business titans like Mark Cuban and Ray Dalio, media mavericks like CNN founder Ted Turner, and mindfulness gurus like Ram Dass and Eckhart Tolle.

Our guests were as wide-reaching as former president Bill Clinton and Pulitzer Prize–winning musician Kendrick Lamar. From professor and author Brené Brown to National Farm Workers association co-founder Dolores Huerta. Organic food champion Alice Waters has shared a podium with the late NBA legend Kobe Bryant, along with former Google CEO Eric Schmidt. Futurist Ray Kurzweil has shared wisdom with our community, as has scientist Craig Venter.

We share these names not to name-drop but rather to highlight common themes that all of these people embody: Vision and drive. A hunger to improve society. An eagerness to inspire the same in others. And, with Summit Series, a platform from which to do it.

What you’ll find in these pages is our origin story and meditations on the philosophies that helped us build our community and our company, despite setbacks and challenges.

The truth is, we had some bruising experiences along the way. Some of the pages that follow are embarrassing. But we want to be honest about who we were, and show you the hard lessons we had to endure in order to gain whatever wisdom we have today. We want to show people how not to stumble where we fell, and encourage them to build something great, even if—especially if—they have no idea what they are doing.

Although the ideas in this book are immensely valuable to each of us, we can’t claim them as our own. We’re not the smartest people in the room; we’re simply the ones who put the room together.

We wrote Make No Small Plans to explain how we created this community despite the odds and, more importantly, to help others think bigger and accomplish more. Envisioning change isn’t just for artists and start-up founders, after all. It’s vital for teachers, nurses, mechanics, parents, and every one of us who wants to make the most of where we are, right now.

What follows is more than a story about four kids who were determined to dream big—it’s the story of twenty thousand of some of the most interesting people alive coming together to improve the future of those who will follow them.

Not only did they teach us about building successful, iconic businesses; they also shared their most intimate life philosophies, dreams, and fears. Over the past ten years, we have absorbed the wisdom of these leaders, and now we want to pass that on to the next generation of leaders.

If there’s one bedrock conviction underlying everything we do, it’s that the world needs more big thinking—and needs it right now. It needs more seekers, dreamers, risk-takers, and doers. Don’t wait for the “right” moment to take that leap; if you do, it might never come. And the world doesn’t have time for that. We need people dreaming crazy ideas and pushing past their reservations. Now like never before, we need to be radical creators, to protect the planet and to do exponentially more good.

The world is too big for small plans. So make yours accordingly.

1 THERE’S NO BETTER BUILDING BLOCK THAN TRUST

If you were thinking about starting a company back in 2007, it’s safe to say we wouldn’t have been your first-round draft picks.

Elliott Bisnow was a socially awkward twenty-two-year-old living in his childhood bedroom who’d dropped out of college to sell ads for his dad’s online newsletter.

Brett Leve was working on commission at a real estate brokerage firm just as the housing bubble burst.

Jeff Rosenthal was frustrated in an associate position at Macy’s, while attempting to create start-ups from a cramped shoebox apartment under a Manhattan highway on-ramp.

And Jeremy Schwartz was playing in a punk rock band named after a science fiction novel and touring the country, living on $8 a day.

We weren’t exactly the Beatles. However, like many of our favorite bands who came together serendipitously, our story didn’t happen overnight.

And it all started with Elliott.

He had just dropped out of the University of Wisconsin—the only college to accept him out of the seven to which he’d applied. Not that he wasn’t smart. He just had his priorities in his own order. For example, one day as his sophomore finals approached, he headed to a study group with his girlfriend. While she took her studies seriously, he spent more time thinking about starting a business than he did attending class. But finals were finals, so he promised he’d join her study group for the cram session.

They stepped into the hush of the Helen C. White Library, where everyone in the group reached into their backpacks and quietly unloaded stacks of books onto the solid wood table. Elliott, however, pulled out a copy of The Wall Street Journal instead. The others looked at him like he was joking, but he began to read in earnest. After finishing the front page, he flipped to the next one, and a silence-shattering crinkle reverberated through the hall. Every head over every table lifted and turned.

“What are you doing?” Elliott’s girlfriend whispered.

“I’m studying the world.”

“This is the time to study for exams.”

“But I need to learn about business. I heard that if I read The Wall Street Journal every day, I can learn how business works.”

Her eyes closed and she slowly shook her head. The relationship wouldn’t last, but Elliott’s interest in the mechanics of the outside world would. It seemed to Elliott that everybody in college was working on the same problems that had already been solved by students the year before, and others the year before that. But Elliott didn’t want to solve his professors’ problems. He had his own problems to figure out.

During his freshman and sophomore years, he’d tried to start a T-shirt business that failed to sell any T-shirts. Then he tried to start a creative consulting firm that never attracted a single client. After his sophomore year, he went home to Washington, D.C., and got a commission-only job selling ads for his dad’s online real estate newsletter. He was terrible at it to start. But that hadn’t deterred him in the past.

For instance, Elliott had started playing tennis at age twelve, years after many other kids got their first lesson. He was so hopelessly behind in the beginning that he lost most of his matches for the first four years. Determined to get better, he played for five hours a day, every day, eventually working his way up to ranking in the top thirty-five amateur players in his age division nationwide. He even received a tennis scholarship to college.

Now, he figured, he just needed to apply the same level of perseverance to being a salesperson.

After a few steakhouse lunches, he got lucky and made a couple of sales. From there, he identified three hundred companies to pitch, typed their contact information into a spreadsheet, and took the list back to school for his junior year so he could make calls from his college apartment.

As it turned out, selling local real estate ads was a lot tougher from 850 miles away. The distance gave him his first appreciation for the value of face-to-face connection. Cold calls could open doors—but then he needed to walk through those doors, shake hands with someone, and get to know them to close the deal. Over that semester, he managed to make a few successful sales, and he finally got his first check in the mail. The way Elliott saw it, the reason everyone went to college was to get a job. Holding that check in his hand, he realized he had a job.

When he went home for winter break, Elliott decided to take a semester off to see how he would fare working full-time with his dad. He attended every networking event in the D.C. metro area to drum up leads. He eventually met a young twentysomething who had the innate ability to connect and easily relate to all kinds of people: Brett Leve.

Brett had grown up in the suburbs of Boston. His dad owned gas stations and was the type of business owner who would personally empty the ATM machines at his business. Brett pumped gas and made sandwiches for pocket money as a kid, but a summer job after he graduated high school changed his outlook on working.

He’d received an advertisement in the mail about selling Cutco knives to family and friends. He learned the pitch and can still recite it to this day: “American-made. Full resin handle. Five-A medical-grade stainless steel. Guaranteed forever, not just in your lifetime; you can pass them on. Your kids can call us and we’ll sharpen them forever.”

Brett sold $50,000 worth of knives in a single summer. At eighteen years old, he ranked fifty-second out of eight thousand sales reps across America. The lessons he learned during those few months would eventually help save our company years down the road.

Back then, Brett saw the money he earned as a means to travel—to get away from the gas station aisles he grew up in. He enrolled at George Washington University in D.C. and started throwing college parties at local clubs. After he graduated, he took a job working for commissions at a real estate brokerage firm. Normally that would’ve been a great way to learn the building blocks of land development—if not for the timing. The gears of the housing market ground to a halt in the run-up to the global financial crisis. With no deals to be made Brett was forced to pay his bills by continuing to throw college parties around the George Washington campus. Which, coincidentally, is how he met Jeff Rosenthal.

Jeff grew up in Dallas, Texas, and moved to Washington, D.C., to study international business at American University with a soccer scholarship.

His childhood was shaped by his grandfather’s philosophy: “A large extended family is the greatest luxury in life.” His grandmother Joy—all four feet eleven inches of her—was the matriarch of the family. She held seventy cousins, aunts, and uncles together by hosting family dinners nearly every weekend. Jeff also grew up with learning differences. His ADHD precipitated his bouncing between schools for most of his youth, and he never felt like he fit in.

Growing up, Jeff had been a goalkeeper for elite soccer clubs. His team competed for national championships, and he was admitted to IMG Academy in Bradenton, Florida, a school that develops players for the U.S. National Team, as well as hundreds of pro athletes in a wide variety of sports.

His dreams were stopped short—literally—when he stopped growing. He watched as bigger, more athletic players saved more goals than he ever could.

Because he couldn’t get much playing time in college, he quit the team sophomore year. For the first time in his life, he was left with an abundance of free time. He began making friends outside of sports, many of whom had come to study in D.C. from around the world; this had a profound effect on Jeff’s worldview, personality, and interests.

His new free time led him to take an internship with Congress, which turned into a full-time job as a floor staffer and congressional wrangler for the Rules Committee in the U.S. House of Representatives.

Around this time, Jeff’s entrepreneurial qualities emerged. He started an online vintage clothing company that did moderately well, and began to throw parties for his AU classmates, which is how he met Brett. Years of competition and exposure to a championship team culture had taught Jeff that players sharpen each other like swords. The camaraderie and shared aspirations of a team create a feedback loop where members have to continuously better themselves—and each other—in order to be exceptional.

This created a problem for Jeff once he was no longer on a team. Without a crew around him, Jeff found it difficult to motivate himself.

He spent close to a year traveling the world, spending what little money he had from his college ventures. Afterward, he moved to New York City, rented a tiny apartment, buoyed a couple of small start-ups, and took an entry-level job as a junior buyer at Macy’s, just as the economy faltered and all of retail shuddered.

Without realizing it yet, Jeff was a player in need of a team as much as we were a team in need of players.

Our fourth member, Jeremy Schwartz, was Brett Leve’s closest friend from high school. While he wasn’t a natural salesperson like the rest of us, Jeremy brought his own unique and much-needed skill set to the group.

His band was named Ice Nine Kills, after a substance in the Kurt Vonnegut novel Cat’s Cradle. The group sold out shows across the United States, became popular using guerrilla marketing tactics on social networking websites such as MySpace, and snuck their way onto the Warped Tour, which was America’s largest traveling music festival at the time. Fans went so far as to tattoo Jeremy’s song lyrics on their arms.

The band had built a loyal national following and were selling out major venues coast to coast. Touring would’ve been a beautiful way for a young man to live out his passion—if Jeremy didn’t have to do it on $8 a day.

Illegal music downloads were proliferating. The record industry was in shambles. Major labels were consolidating. The only money the group made was from touring, CDs, and merch sales. Fans offered up their homes as crash pads. They were so supportive that when the band’s van broke down, they housed and fed the musicians for the two weeks it was in the shop.

Jeremy loved performing and was at one with the band’s loyal community. But the grind of touring nine months out of the year was taking a toll. Despite the band’s growing success and popularity, Jeremy decided the lifestyle wasn’t for him. Brett offered him a different path, so he parted ways with his band and joined us.

Our destiny was to build a community—to support a scene of entrepreneurs that would come to define a generation of world-changing businesses. But at the time, we were all just looking for friendship. We were a crew of college dropouts and eccentric creatives who found solace in supporting each other’s wildest ideas. And we figured there must be more of us out there.

So we decided to take a risk. And then we kept on taking that risk again, and again, and again. We repeatedly pushed all our chips into the center of the table, and each time the wins outweighed the numerous losses.

That didn’t make it easy, though. Bold ideas challenge our identities. They threaten what we have and what we know. We don’t trust them, not because they break the rules but because they create new ones of their own.

But the Great Recession had shredded the old playbooks, along with the stock market, and we saw a space emerging where a new trail could be blazed. Take any public figure you admire and chances are they reached success by pursuing a bold and disruptive path—by hatching a crazy idea and sticking with it.

Elliott was the first of us to dream that big.

2 YOUR REACH SHOULD ALWAYS EXCEED YOUR GRASP

Elliott may have had a dream, but that didn’t mean that he had any idea of what he was doing. In 2006, a year before Elliott and Brett would first meet, Elliott finally decided to drop out of college to join his dad’s business selling real estate ads full-time. He had a few early successes closing deals, and figured that he was going to learn more from chatting to businesspeople back in D.C. than from his introductory economics classes in Wisconsin.

Night after night he headed off to events filled with strangers without really understanding how to engage them. Elliott viewed every handshake as a new prospect to convert into ad sales. But with enthusiasm as his only tool, he could come across as a little too eager.

“Hi, I’m Elliott from Bisnow on Business. I just wanted to say hello! What do you do?”

“Hi, I’m Elliott from Bisnow on Business. Great to meet you! Are you looking for more exposure for your company?”

“Hi, I’m Elliott from Bisnow on Business. Loving that shirt! What are you working on currently?”

People who loved him began to call him “Casino-Floor Elliott”; those who didn’t coined less endearing terms. But his persistence paid off, and late in the evening he’d return to his tiny rented office across from the White House and enter the business cards he’d gathered into his company’s database. Then, instead of trekking back to his parents’ house on a cul-de-sac in D.C., where he still lived, he’d often crash on some seat cushions placed under his desk.

While his college friends were out partying in Wisconsin, contemplating their first internships, and deciding on their major, Elliott would wake up in that shabby office and spend much of his day cold-calling potential clients. Elliott had intentionally rented his office space a hundred yards from the White House so he could tell people he was in the center of the action—even if getting to his office meant riding up a creaky elevator and walking past other offices with windows looking into alleys on his way to his own office, which didn’t have a window at all.

He’d pick up the phone and open with “Yes, I’m calling from next to the White House” to try to impress clients. It didn’t work. Nor did cold-calling the other tenants in the building to try to sell them advertising. Eventually, the building’s general manager intervened. “Stop cold-calling our tenants,” he warned Elliott. “Also, I know you’re sleeping under your desk at night. Stop that, too.”

The landlord had figured out that Elliott was crashing in the building because one night, after a Casino-Floor Elliott session, he got locked out of his office—in his boxers and T-shirt. He couldn’t figure out how to get back in, so he had to ask a night manager at the front desk to open the door so he could get back to the safety and comfort of his shoes and pants.

Elliott was making some sales, however, and he was happy to be building a business with his dad. But the grind felt meaningless, and it made him wonder if this was what he’d been put on the planet to do.

The truth was, Elliott had no idea what he wanted to do. He’d met plenty of salespeople and real estate agents since dropping out of school twelve months prior, but aside from his dad, he didn’t know a single person who had started a business.

He wanted to meet somebody wired like he was, but more experienced. Someone who could show him the way. That person wasn’t knocking on the door of his small office—even if it was “next to the White House.”

Snow was falling at the end of 2007 when Elliott heard of relationships being formed on chairlifts and deals being made over après-ski drinks. He realized that networking opportunities weren’t restricted to city streets—they could take place on ski slopes as well.

Elliott had an idea. His aunt and uncle lived not far from a ski resort in Utah, and he’d vacationed there growing up. Maybe it was time to pay them a visit.

The childhood dresser where Elliott used to put away his clothes was now filled with thousands of business cards. He decided to tap into his network and invite a group of people to the mountains in the hopes of getting to know some of them. If he selected the right twenty people, perhaps he could establish seven or eight friendships, and those new friends could show him the way. (And if he made some ad sales out of it, even better.)

He turned to a fresh page in a spiral notepad and wrote: “The Best of the Best.” He listed twenty people he was on good terms with whom he thought he might be able to learn from. The list included a real estate broker, a furniture salesperson, a manager at a construction company, a host at a local restaurant, an insurance risk analyst at AIG, and a college graduate who’d just taken a job at AARP.

Elliott emailed them his pitch: “I’m an entrepreneur. I really want to bring together twenty creative people and build a peer group so that we can connect with each other, meet new friends, and brainstorm. I don’t know most of you that well. What if we went off to a ski retreat in Utah for a weekend to really connect?”

Then he called them one by one to see if they’d be interested.

“Why would I go on a ski trip with twenty people I don’t know?” the first invitee said.

“Not a good idea,” said another.

“My next vacation is in six months,” said the third. “I’m gonna go with my friends. I don’t want to meet your friends, who, it seems, you don’t even really know that well.”

Elliott drew lines through the names of everyone who said no. But he didn’t give up. He kept reaching for his phone. The lawyer wanted to know why he should meet the furniture guy. The furniture guy wanted to know why he should hang out with the insurance risk analyst.

There seemed to be some interest on the next call, with the real estate broker.

“When’s the trip?” he asked.

“April 17.”

“April 17? That’s a terrible time for a ski trip!”

“It’s not about the skiing!”

“So, you want me to go with all these random people I’m not interested in? Why don’t you come by my office instead? We can chat about real estate brokerage.”

“I don’t want to chat about real estate brokerage!” Elliott said. “I want to meet other entrepreneurs!”

Elliott continued to cross off names as he went down the list, and the further down he got, the more adamant the responses became. But he kept on calling.

“You don’t even know how to plan a trip,” said the next. “I know you; you can’t even sell ads! How am I going to trust you to plan my vacation?”

Another line through another name.

Finally, Elliott reached the last person on the list after days of trying.

“Come on,” Elliott said, “I’ve called you twenty times to ask you if you wanted to go on my ski trip.”

“If I wanted to go, I would’ve called you back.”

The last name on his pad was crossed off.

Not a single yes. And still Elliott believed in his idea. He wasn’t bothered by rejection. After all, he made cold calls for a living.

Thanks to all his years as a lousy tennis player with a dedication to the grind, Elliott processed losses differently than most other people. When he reviewed the avalanche of nos on his pad, he had an epiphany: No one he reached out to thought his idea was interesting enough. He was thinking too small, and his intuition now pointed him toward something much larger.

Summit Series was born the moment Elliott realized he needed a more inspiring list of names.

3 READY, FIRE, AIM

Sometimes you can have the right idea and pitch it to the wrong person.

The names on the business cards gathering dust in Elliott’s childhood dresser were valuable if you were selling insurance or couches. But Elliott wasn’t aspiring to be a furniture salesperson. Which people, Elliott wondered, did he really wish he could spend time with and learn from? He started to think about the companies that inspired him and the new generation of entrepreneurs behind them.

He put down the spiral notepad, turned on his computer, and created a new spreadsheet. He searched for people his own age who had seemingly created something out of nothing. The names at the top of the list included:

Blake Mycoskie: Blake had invented an entirely new way of looking at business with TOMS Shoes. With every pair sold, TOMS gave a pair of shoes to a child in need.

Ricky Van Veen and Josh Abramson: In addition to starting Vimeo, one of the world’s biggest video sites, Ricky and Josh assembled the world’s largest repository of jokes and funny videos as founders of the website CollegeHumor.

Joel Holland: Joel had landed on Business Week’s “25 Under 25” list after he traveled around the country as a teenager filming video clips of skylines and city landmarks. The video service he founded, VideoBlocks, saved companies thousands of dollars in fees that were being charged by traditional competitors for stock footage. And he was still in college.

These were the types of people Elliott related to and wanted to learn from—and he figured they might be able to learn something from each other, too.

Joel Holland was Elliott’s first call. Elliott sensed if he could get Joel to come to Utah, it would make the calls that followed easier. By confirming someone on the “25 Under 25” list, he would validate the trip and incentivize others to join.

Elliott first reached out to Joel shortly after Business Week’s list appeared. But Joel was naturally receiving lots of calls at the time—and ignoring most of them. If the calls were truly important, Joel figured, the callers would try again. Elliott called a second time, and again Joel didn’t pick up. But after Elliott bombarded him with Facebook messages, Joel finally gave in.

When they met over lunch, Elliott pitched him his far-fetched idea: to bring together a bunch of young, committed company founders—whom he didn’t know, and who didn’t know each other—on a mountain, to discuss professional challenges facing their businesses and find collaborative solutions.

Joel wasn’t sold. He told Elliott that entrepreneurs tend to be motivated by their singular visions. America’s love of individualism tended to outweigh the sacrifice required for the greater good. He was a no.

So Elliott turned to the next names on his list: the founders of CollegeHumor.

Childhood friends Ricky Van Veen and Josh Abramson had started their company in 1999 while studying at different colleges. Elliott had been captivated by one of their videos and watched it on repeat in his college dorm. Ricky and Josh also caught his attention because, back in the nineties, college students rarely started their own businesses. (Oh, how times have changed.) Elliott dreamed of doing everything that Ricky and Josh were doing.

By the time he called them, CollegeHumor had grown to about fifty employees and moved into a loft-like headquarters in lower Manhattan. Their assistant refused to let Elliott’s calls go through time and again, but Elliott kept trying. Finally, in exasperation, the assistant passed him on to Josh.

Elliott gave him the pitch. Josh thought he was a lunatic and that the ski trip would be a disaster. Why would he fly all the way to Utah with this kid from “next to the White House”? But Josh’s company was founded upon humor, and he couldn’t resist the opportunity to play a prank on his unsuspecting co-founder. He told Elliott he thought the ski trip was a brilliant idea, gave him Ricky’s cellphone number, and encouraged Elliott to call.

When Ricky answered the phone, he thought Elliott was trying to sell him a time-share at a ski resort. But there was one line in Elliott’s pitch that he just couldn’t wave aside: Elliott was offering first-class airline tickets to Utah. Ricky and Josh had been written up in The New Yorker, but they’d never flown first-class. Ricky was curious.

Who was this guy, Elliott Bisnow? Nobody threw conferences or retreats for entrepreneurs in their twenties and thirties; the best they were getting in New York was an overstuffed happy hour in a lavish loft downtown. Was this a scam?

They figured there was only one way to find out. Entrepreneurs tend to have a higher tolerance for risk—and this one came with cushy plane tickets. Ricky was curious about Elliott because, unlike the people on Elliott’s original list, Ricky had no clue who Elliott was. He walked over to Josh’s office with a question.

“Doesn’t Ben Lerer have a house in Park City, Utah?”

Ben was a friend of theirs who had started a website covering food, drink, travel, and entertainment, called Thrillist.

“Yeah, Ben does have a house there,” Josh responded warily, realizing his prank had backfired and Ricky was now actually interested.

Ricky figured that if they went on this ski trip and it was a hoax, they’d at least have first-class tickets to fly out and see Ben. Plus, they could ask this overenthusiastic character to invite Ben on the ski trip, so they’d have safety in numbers.

And just like that, Elliott had his first two guests locked in. Not only that, but he had one of New York’s rising young entrepreneurs thrown in for free.

Except it wasn’t free. Not for Elliott. He had no idea how much all of this was going to cost. He hadn’t priced out the first-class airfares, or figured out how he was going to afford the accommodations, dinners, and ski passes he was promising. He didn’t have a budget—but he did have some credit cards.

Elliott doubled back to Joel Holland. But instead of asking him to fully commit, he posed a different question, one that would later become the bedrock of Summit Series’s strategy for growth: Elliott asked him if there was anybody else he knew who might like to come.

Joel threw out a few names and vouched for them. As he did, he began to wonder: If I’m suggesting that my friends go on this wild, all-expenses-paid ski trip…why am I not going with them?

So Joel was all in.

That was the moment Elliott knew. If he could get four yeses, he could get twenty. There’s a critical tipping point of momentum for anything in the world, whether it’s physics or business. Getting the initial traction is the most difficult part, but once things are moving, it gets easier and easier.

Next, Elliott reached out to Blake Mycoskie at TOMS. Elliott had been fascinated with TOMS ever since college, when he’d first read about them and immediately bought a pair of their shoes.

The company had a simple backstory. During a trip to Argentina, Blake had noticed that many children weren’t wearing shoes. But instead of just buying a pair for the kids he met, he wanted to find a more sustainable, long-term solution. He decided to work with a local cobbler to make traditional Argentine alpargatas that could be sold in the United States to subsidize footwear for those who didn’t have any. When a Los Angeles Times reporter wrote a story about TOMS after the first pairs appeared in a boutique, Blake was immediately overwhelmed with fourteen times as many orders as his available stock. He could barely keep up. TOMS would go on to give away more than a hundred million pairs of shoes.

But back then, Elliott was curious about how Blake would scale a company built on such a humble business model. So he called Blake’s rickety old warehouse in Santa Monica. Fortunately for Elliott, Blake’s assistant appreciated his optimism and persistence. After multiple checks to confirm the trip wasn’t a scheme, the assistant passed along the invitation to Blake, emphasizing that it was all-expenses-paid: “Worst-case scenario, you’ll get a free weekend of skiing out of it.”

Blake was intrigued enough to take the call. He listened attentively, then ultimately asked the same question that everybody else had asked: “Who else is going on the trip?”

Elliott rattled off the names. “Joel Holland from Business Week’s ‘25 Under 25’ list, Ricky Van Veen and Josh Abramson from CollegeHumor, Thrillist founder Ben Lerer…”

Blake was in.

Now Elliott had to figure out a way to pay for it all. Though he still had no idea how much it would cost him, he knew it would be smart to try to get sponsors to cover his losses. So he started making calls.

He knew a guy named Steve who had been a volunteer football coach for his brother in high school and now had an entry-level job as a broker at commercial real estate giant Jones Lang LaSalle. He begged him to use every connection at the company to convince them to put up some money. “You could meet some good clients on this trip, Steve,” Elliott pitched, trying to bite back the desperation in his voice. “What if your firm put up $10,000 as a sponsor?” Then he held his breath.

He didn’t realize just how good that opportunity might have sounded to Steve. It put an entry-level broker trying to drum up business in the position to pitch a creative idea to his boss. Luckily for both of them, Steve’s manager saw the upside, and the company put up $10,000.

Now Elliott realized he wasn’t selling a ski trip—he was selling a new business opportunity. Who else, Elliott wondered, would want to be around the next generation of business leaders? The answer became clear to him: venture capitalists. He rustled through his stack of business cards and called a contact at a VC firm he’d met just once. “This trip is a great opportunity to get leads,” he promised. “And you’ll never guess who else will be there.”

After some wooing, it worked. The VC firm decided to toss in $10,000 as well.

Ideas for other sponsors began to click. It dawned on Elliott that his ski gear was seven years old. What if he could get some new winter apparel for everyone? He cold-called a marketing manager at The North Face and boldly asked: “Are you interested in changing the trajectory of your brand forever?” To Elliott’s surprise, they actually were interested. It turned out that they liked the idea of marketing to a new generation of entrepreneurs. That and Elliott’s ask was actually quite small by their standard. North Face came through with twenty jackets and twenty travel bags.

Then he contacted Fortune. He figured a media sponsor would really give his event some credibility. The magazine declined to give him sponsorship money, but one of their editors was intrigued by the idea and decided to have a reporter call with questions.

Elliott had solved his first problem: getting twenty busy people to come skiing with him. He’d even nearly solved his second problem: The entire event would add up to about $38,000, and Elliott had recouped roughly $30,000 in sponsorships. His credit cards could shoulder the rest.

But he had no idea that his solutions had snowballed into a whole new set of problems.

To start, where would they all sleep? Airbnb was nearly a year away from its launch, and regardless, Elliott had never rented a home before in his life. He’d lived in dorm rooms in college, and now he was back living with his parents (when he wasn’t sneakily sleeping under his desk). In fact, the only vacations Elliott had ever been on up to this point had been family trips. That meant he’d never booked a hotel room. He’d never made a dinner reservation at a restaurant. He’d never even purchased any alcohol, because he didn’t drink.

He needed help, so he called in the cavalry: his mother, Margot. As the parent who had brought all of his childhood holidays to life, she came to the rescue, as mothers often do, and found a ski house at Alta Ski Area in Utah. There was just one issue: The home she rented had only nine bedrooms. Elliott had nearly twenty guests coming. He was going to have to ask nearly two dozen strangers to share rooms.

Still, there was an even bigger problem. Elliott had absolutely no idea how to throw a party.

4 AUTHENTICITY TRUMPS PERFECTION

Elliott landed in Salt Lake City on a crisp, clear Friday afternoon in April 2008—only two hours ahead of his guests. He rented a Suburban and raced to a convenience store to pick up some snacks for their arrival, and proudly bought beer for the first time in his life.

Everything seemed set as he arrived at the house to unpack. He now had a case of beer in the refrigerator and what seemed like a mountain of snacks on the table. And it was a mountain of snacks—for one person. We’ll probably have beer one night this weekend, he imagined, and everyone will have one.

As guests began to trickle in, Elliott graciously gave a tour of the rental home to each new person who arrived.

“There are no plans for this weekend,” Elliott told Joel Holland as they headed for the kitchen. “The idea is for everybody to get to know each other. The entire weekend is one big party!”

Elliott proudly swung open the door of the refrigerator to reveal twenty-four cans of beer.

One case of beer? For twenty people? This, Joel thought, is going to be one hell of a party.

With beer having historically proven itself to be a wonderful social lubricant for young people in uncomfortable settings, those twenty-four cans disappeared almost immediately once the guests found out they’d be sharing rooms with people they didn’t know.

All anybody could feel at this point was a deep sense of awkwardness.

Things only got more uncomfortable when an artist Elliott had invited showed up. He had asked the painter to showcase his canvases, thinking that the display would add some creative energy to the group. Tempted by the prospect of making sales to a collection of highly successful entrepreneurs, the artist had transported his life’s work to the event in a U-Haul. At the time, most of the young entrepreneurs were completely focused on their businesses, and while they were wealthy in start-up stock, not one of them had ever bought art, nor had the slightest interest in purchasing any on this trip. After the artist unveiled his creations, he eagerly moved throughout the room, seeking sales, while all the entrepreneurs deftly looked for ways to avoid him. They opened their laptops at a long table, because “having to get some work done” felt like a reasonable excuse. “Going out on a beer run” also did the trick—and eased the rapidly snowballing tension.

Ricky and Josh from CollegeHumor immediately zeroed in on all the discomfort and decided it would be fun to create some more. When the group piled into a few cars and headed to the upscale restaurant Elliott’s mother had scouted out for dinner, Ricky and Josh were already hatching a plot.

The group convened around a long table, with Elliott positioned at the head. When Elliott got up to go to the bathroom, Ricky and Josh quickly told everyone their plan: They would hand the maître d’ a white card to place in front of Elliott when he sat back down. They asked the rest of the group to play along.

Elliott returned to the table and took his seat, and the maître d’ gave an award-winning performance. “So sorry,” he said remorsefully, delicately placing the note in front of Elliott. He was so sincere that it was obvious there was a problem.

“Elliott, what’s that?” Josh pried.

“I just got the weirdest card.”

“What does it say?”

Your attire is not appropriate to the standards of the club, and we ask that you change immediately.

—Management

“Oh man, you need to go change,” someone called out.

“I don’t have extra clothes in the car!”

“Well, where’s the closest store you can buy some?”

“I don’t know.”

“But you have to change.”

“What’s wrong with my clothes?”

“Look at your shirt. It’s not appropriate.”

“It’s a button-down shirt. The same kind as you’re wearing.”

“It’s not the same. Look at the color of your shirt!”

This went on until every inch of Elliott’s attire had been thoroughly dissected down to the contour of his collar. Elliott’s frustration mounted until everyone burst into laughter.

Elliott shut his eyes and gave a reluctant smile. Then he began to laugh along with the table. In that moment, all the tension that had been accumulating from the time everyone arrived was released. Lively conversations sprang up around the table, and everyone began to relax into the evening and connect on a deeper level. At the end of dinner, everyone was in a jovial mood, and far too many people crammed into the back of Elliott’s Suburban for the trip home.

It was dark when Elliott began driving the rowdy crew back, and there were no other cars on the road. He approached a sign that read No Left Turn. But because the road was completely empty, and the home Elliott had rented was to the left, he took the turn. As soon as he did, a siren pierced the darkness. A police car had been in hiding, and it pulled behind the rental car as Elliott rolled the overstuffed vehicle to a stop.

The patrol officer sat inside his cruiser for an excruciatingly long time. Ben Lerer seized the moment.

“Bisnow, you’re going to jail! Your event is over! And it’s never even started!”

“Stop! I didn’t do anything wrong!”

“Yes, you did. We’re crammed in here like sardines. We’re illegally sitting in the back!”

Elliott was eyeing the patrol car in the rear-view mirror, nearly obscured by the nine people in the back seats.

“Stop it, Ben!”

The tension in Elliott’s voice was an open invitation for everybody in the Suburban to pile on.

“You shouldn’t have been drinking, Elliott!”

“I don’t drink!”

“You’re going to jail! It’s Friday night—you’ll be there all weekend. But don’t worry. I’ll drive the car, take over the house, and run your event!”

Everybody in the car was howling at Elliott just as the officer exited the cruiser.

“Shut up, Ben! Please!”

Laughter was almost bursting through the closed windows as Elliott’s heart pounded and the officer approached the door. And then, suddenly, there was a respectful, almost cinematic silence.

Elliott rolled down his window. The officer took his driver’s license and registration, peered suspiciously into the back of the vehicle, and then walked back to the cruiser. Elliott felt like he was being investigated for an hour, and the guys in the back seats used every traumatic second of it to heap more comic abuse on him. Finally the officer returned and calmly extended a ticket, as he would have to anyone else.

Once Elliott’s window was back up, the heckling flared up again and followed Elliott all the way home. It was an initiation that was a better bonding experience than anything Elliott could’ve planned. Nobody minded sharing a bedroom with others after that. There was so much to rehash and laugh about, most of it at Elliott’s willing expense. It felt like summer camp, except with more snow and less poison ivy.

The next day, everyone hit the slopes. Sam Altman, the future president of Y Combinator, and the founders of Vimeo and TOMS were hanging out and swapping stories of their struggles. They were learning about each other’s best business practices and how they balanced work with their personal lives. Each shed light on past failures and what could be learned from them. By the end of the weekend, everybody was familiar with everyone else’s businesses and the stories that made them. Some of the guests had even begun lifelong friendships.

But perhaps Elliott had learned the biggest lesson of all. So many people are frightened to throw an event, set up a meeting, or even send an important email unless it’s perfectly crafted—as if you shouldn’t put yourself out there unless everything is flawless.

Elliott understood in that moment that the most important quality an event can have is space for the unplanned—room for the spontaneity and randomness that create sparks. It’s the difference between a highly polished apple you get in the supermarket and the slightly bruised organic one that’s fallen from a tree. Brush it off, and the roadside apple tastes infinitely better.

Just as Elliott had relentlessly picked up the phone to call people, he’d followed through and thrown an event that even his friends thought he was crazy to attempt to host—and now he had twenty new friends who didn’t think he was crazy at all.

In fact, they actually kind of liked him.

As his guests left the mountain, they asked Elliott if he’d assemble another get-together for everyone six months down the road. The idea had never even occurred to him; he’d barely managed to pull a single weekend off, and it would take him months to pay down his credit card debt. After he said goodbye to the crew, he soon got a phone call from the Fortune reporter asking how things went. As the call was wrapping up, the reporter posed one final question.

“So, what’s your event called?” the reporter asked.

It didn’t occur to Elliott to have a name for the ski trip. Why would he give the trip a name? He didn’t have a name for hanging out with friends on the weekend, so how was this any different?

“What do you mean?” he asked.

“You organized an event. What’s the name of it?”

“Right. Of course it has a name…”

“Well, what is it?”

Elliott glanced at the North Face jacket he was still wearing from the weekend and read the words right off the sleeve.

“Summit Series.”

5 REPLACE YOUR WEAKNESSES WITH A PARTNER’S STRENGTHS

Suddenly people were returning Elliott’s calls.

Apparently, you get a warmer welcome when you actually have a track record of flying people first-class, introducing them to people they wished they could meet, and hosting them for an exciting weekend, all expenses paid.

After hearing how amazing the ski trip was, those who’d declined Elliott’s first invitation wondered what they’d missed. They apologized, left him voice messages, and asked him when he’d be organizing the next one. And where? The snow was melting in the mountains, after all, and a year seemed like a long time to wait.

So Elliott decided to swap the snowboards for board shorts as he started dreaming up the next event. Sixty promising entrepreneurs. Six months down the road. Sunny Mexico.

He could practically feel the sun on his back just thinking about it: a long weekend spent trading business tips, while his guests sipped margaritas by the pool and swam with tortugas. It was a welcome daydream—he was still living with his parents in his childhood bedroom and working in an office with no natural sunlight.

Elliott also couldn’t afford to take time off work—that credit card debt wasn’t going to pay itself off—and he wasn’t going to ask his mother to scout the location for him a second time. But a friend who was feeling stifled by his corporate job leapt at the opportunity to help.

Ryan Begelman was working in a prestigious private equity firm in D.C. Most of his job focused on buying and trading real estate, but part of the position entailed downsizing companies that had been purchased in large acquisitions. In other words, he fired people.

After several years, Ryan grew tired of crunching spreadsheets all day in an uncomfortable suit. So, unbeknownst to his boss, he began looking at small real estate projects to buy in the D.C. area. He figured it might be his way out.

Eager to learn the local real estate market, he discovered a witty email newsletter about local real estate produced by Bisnow on Business. He became obsessed with it. With the desire to meet the newsletter’s creators, Ryan tracked down Elliott at a real estate networking event, and cornered him on a rooftop overlooking the D.C. skyline. Upon meeting Elliott, Ryan was blown away. Who is this kid? Two years younger than me and already living my dream of being an entrepreneur.

Ryan started going to Elliott’s office daily to talk business ideas and learn how Bisnow on Business worked. The two became fast friends, so when Elliott reached out to Ryan asking for help planning the Mexico event, he was happy to plug in.

Ryan was a skillful planner and organizer. He hit the phones, calling every resort in Mexico to figure out a location and accommodations that wouldn’t bust the bank.

He chose a location near Cancún. It seemed like an exciting getaway, and Cancún had direct flights from most major cities. Within a few hours, attendees could be on a white-sand beach surrounded by crystalline water. He found a hotel at Playa del Carmen that could accommodate everyone. It wasn’t a five-star place—and yes, people would need to room together (again)—but Elliott had realized that intimacy was part of what made the first event so successful. Sharing rooms had created the summer-camp vibe that broke down barriers in snowy Utah.

With Ryan on board, Elliott no longer had to worry about logistics, something he wasn’t very good at. That left Elliott with the time to do what he did best: cold-calling strangers.

The guests on the list he began putting together may not have known each other, but as post-dot-com business owners, they shared common aspirations and struggles. It was like the Ten Thousand Islands chain off the southwest coast of Florida: When you were on one of those islands, looking out at the expanse of water all around, you felt alone. But if you looked down from a great height, you would see how all those islands seemed to be linked in a chain.

Elliott’s goal was to build a road that bridged all of these lonely islands. He wanted to show entrepreneurs who felt isolated how connected they actually were.

Facebook started in 2004. YouTube launched in 2005, Twitter in 2006. And the iPhone dropped in 2007. It was now the summer of 2008. Start-up culture was flourishing, and the Internet was allowing young people both in and out of college to market and sell their products online. With Summit Series, Elliott wanted each of those businesses to feel like they were connected to a burgeoning community, and that lessons learned by one could help lift another.

With all of Elliott’s new connections, there wasn’t a shortage of people to invite. His first list of names contained some of the brightest young business leaders in America.

Tim Ferriss: Tim published what became the modern manual for founders called The 4-Hour Workweek in 2007, and agreed to speak at the event in Mexico.

Scott Harrison: Scott started Charity Water, a nonprofit that brings clean water to parched areas around the globe. He also agreed to give a talk.

Catherine Levene: Catherine ran DailyCandy, one of the most popular email newsletters in the United States, which would eventually be sold to Comcast for $125 million.

Chris Sacca: Chris jumped in even before he’d begun raising money for Lowercase Capital, which would become one of the most successful VC firms of all time.

Garrett Camp: Garrett would go on to co-found Uber.

Caroline McCarthy: Caroline would become a marketing strategist for Google, connecting the company with the most influential minds in social media.

Tony Hsieh: Tony was revolutionizing customer service over the Internet through the online retailer Zappos. A year after the Mexico event, he’d sell the company for a billion dollars.

Besides their obvious business accomplishments, the attendees possessed something even more meaningful: Each was driven by a passion, a powerful curiosity, and the will to succeed and push the world forward. This was the deeper bond that connected everyone. All of these entrepreneurs said yes. The more that other young business owners heard who was coming, the more momentum the list gained.

It wasn’t all good news, though. Expenses for the Mexico trip were much higher than what Elliott had racked up in Utah. He knew that he could no longer afford to fly his guests to Mexico first-class, so the invitation let attendees know that it was up to them to get to Cancún. Once they arrived, however, everything would be covered. While the guys who heckled Elliott from the back of the Suburban in Park City couldn’t resist poking fun at the disappearance of their first-class plane tickets, everyone understood that he couldn’t fly in sixty guests internationally.

Even so, Elliott was going to have to raise roughly $130,000 in sponsorships to balance his costs—and he had to bring in this money while also working his day job. Fitting it all in was no easy task. He bounced between responding to emails about ad pixel dimensions, making cold calls to prospective new clients, and trying to confirm the attendance of the co-founder of Facebook. There was only so much time in a day, and he’d need some help selling sponsorships to the Mexico event.

Meanwhile, Ryan Begelman was cold-calling the ad agencies of Mercedes and Nike, trying to persuade them to contribute, and striking out left and right. That’s when Ryan made a suggestion.

What about Brett Leve?

Of course. Brett Leve.

Elliott had first met Brett at an Urban Land Institute event that the two had attended to network. Elliott was there to gobble up business cards to help him sell more ads. Brett was there as a broker looking to meet people interested in developing real estate. But when the crowd that night filed into an adjacent room to listen to a lecture, the two of them were left alone at a table of crudités.

“Hi, I’m Elliott from Bisnow on Business!” Casino-Floor Elliott chirped. “Nice to meet you. Looks like you’re the only other young person here.”

“It does, doesn’t it?” The casino vibe didn’t really go over well with Brett.

“What do you do?” Elliott asked.

“I’m in real estate.”

“Amazing!” Elliott said. “I’m in real estate, too! I have two seats to a Washington Nationals gala tomorrow night. You should come!”

Elliott assured him there were great connections to be made, and even though Brett felt something off-putting about Elliott, he couldn’t help but be intrigued by his awkward exuberance. Something compelled him to say yes.

The following night, though, Brett didn’t feel well. As he watched Elliott run circles around him snatching up business cards at the gala, he decided to leave. He thanked Elliott for the invitation, said goodbye, and headed home early.

“No worries,” Elliott said, immediately pivoting to the person next to him. “Hi, I’m Elliott!”

Over time, Elliott continued to reach out to Brett. (In fact, Brett had even been one of the names on Elliott’s original list of twenty local businesspeople. He had declined, just like the nineteen others.) Elliott eventually introduced him to Ryan, and it turned out that they lived a few blocks apart and went to the same gym. Brett and Ryan started to hang out every day and became close.

Less than a year later, after the successful Utah trip, Elliott felt confident he could handle the invite list for the Mexico event. He knew that Ryan could take care of logistics. What he needed was somebody who could make a party come to life and bring in sponsorship money.

Ryan reached out to Brett. “Remember that guy Elliott? Well, I’m spending a lot of time these days working with him,” he said, “and I think you might want to get involved.”

Brett hesitated. “Yeah, I’m not so sure about that guy.”

“Look, he’s…different,” Ryan said. It was true. Elliott had spent nearly his entire adolescence obsessed with tennis and simply didn’t know how to converse with people in a work setting. Brett, on the other hand, had casually learned social dynamics by selling knives and throwing parties in college. “But that’s what makes a strong team, having people with different skills. You could really help us out.”

Brett certainly knew everything Elliott didn’t know about entertaining people. But he didn’t want to help throw another party, as he did enough of that on weekends. If Brett was going to join, he was only interested in selling sponsorships. He figured if Elliott’s concept didn’t work out, he could at least use the sales opportunity to make some money for himself and also to make new connections that might benefit him down the line.

Brett met with Elliott and offered to bring in sponsorships on commission. To Brett, working on commission was not only the best indicator of people who are confident in their abilities and willingness to work, but not asking for a salary took all the defensiveness out of the negotiation.

The deal was done over a handshake. Brett would receive 20 percent of the money he brought in, and if that total exceeded $30,000, there’d be an opening for Brett to join as a partner.

It was not an easy time to sell sponsorships, though. Brett called every VC and law firm he could think of and only got two bites. After two months of work, he’d pulled in only $9,000.

Finally, things took a turn. Staples, the office supplies retailer, had just acquired a company called Corporate Express as a way to expand its business into servicing corporate accounts. Brett’s dad knew a guy at Staples who’d worked on that acquisition, Jay Baitler.

Jay was the ideal referral. Brett knew he’d only have one shot at convincing Jay to come on board, but Brett was ready. In fact, he had been preparing for this call with Jay since he was seven years old. Brett’s work ethic had been forged at his dad’s gas stations. His dad worked six days a week, and took off Sundays only because Brett’s mom insisted. Brett figured out early on that the best way to spend time with his dad was to go to work with him. That put him on top of milk crates behind the gas station counter when he was in second grade, and over the years he scrubbed the bathrooms, pumped gas, cleaned the bays, and grilled up steak-and-cheese sandwiches at the station’s sub shop.

His extroverted nature worked well behind the counter when he was young, and it worked even better years later selling cutlery for Cutco. When he went off to college and needed some cash in his pocket, Brett gravitated toward throwing parties—basically selling college kids on the idea of an unforgettable night. His style further evolved when he graduated, fusing what he’d learned selling knives in high school with what he’d picked up in college. He headed into land development, convincing property developers to build their condos on his boss’s land.

In short, Brett had been selling one thing or another almost every day for nearly six years leading up to his call with Jay Baitler, and he wasn’t nervous in the least.

“Staples is a world-class brand,” Brett said to start the call, “and Corporate Express is an amazing acquisition. You have billions of dollars in annual revenue.” He explained how the workplace was changing, that millennials were growing organizations that rival the biggest companies in the world, and that some of the most influential members of this new generation of leaders were going to be at this Summit Series event in Mexico. “This is an opportunity for Staples to get in on the ground floor with these people and develop relationships that will turn into massively valuable channels for sales and revenue.”

Brett couldn’t tell if Jay believed what he was saying. Jay’s tone gave the impression that he was thinking: Okay, kid, your dad’s a nice guy. But are you sure you can play in this league, or are you just talking a good game?

The price of admission was small enough to find out. What’s $15,000 or $20,000 to a brand like Staples, Brett thought, when it could be in a position to gain fifteen or twenty key accounts?

“Just being around these young people,” Brett pressed, “is a huge opportunity.”

“Okay, I’ll do it,” Jay said. “But all I can give you is $30,000.”

Thirty thousand? Brett held his breath. Did I really just hear that?

“Jay, if you cut me a check for $30,000,” Brett said, “we’ll name this entire event after your company!”

And that is how the event in Mexico came to be called the Staples Young Leaders Summit.

As it turns out, that sponsorship would be instrumental in getting the fledgling company through a particularly tough time. By October 2008, only a month before the event in Mexico, the Great Recession had shredded the housing market and cratered stocks. In September, Lehman Brothers, a pillar of the financial community for 158 years and the fourth-largest investment bank in the United States, had filed for bankruptcy. There were deep concerns that the Big Three auto companies would be taken down, along with the city of Detroit. Layoffs immediately began through every region of the country, affecting nearly eight million jobs.

The recession would have given Elliott, Ryan, and Brett every excuse in the world to pull the plug on the second Summit Series event.

But, as we’d soon learn, it’s times like these when we need community the most.

6 KNOW YOUR DEFINITION OF SUCCESS

A few months later, Elliott strolled around the hotel grounds at Playa del Carmen with Ryan and Brett, admiring the swimming pool, thatched huts, and quaint cabanas cascading down to a pristine white-sand beach. He explored the activities center and learned about the coral reef and nighttime snorkeling with flashlights and stingrays. Look at this. It’s all ours!

His guests, however, had a very different reaction when they arrived at the hotel.

“Elliott, there seems to be a mistake. I just checked in and somebody else’s stuff is in my room.”

“Oh don’t worry, it’s definitely not a mistake. I know exactly who your roommate is and you’re going to have the best connection ever.”

“But I want my own room.”

“Trust me. Your roommate’s incredible. That’s how it is at summer camp, and that’s how it is here!”

There was almost no time for this strategy to backfire. Once all of the guests had arrived under the thatched roof of the indoor-outdoor hotel restaurant, they were greeted by the first speaker: Scott Harrison. As soon as Scott began sharing his life story, the room grew very quiet.

Scott had lived a very conservative upbringing before he became a nightclub promoter cavorting at the height of extravagance. Vodka bottles in blocks of ice. A model for a girlfriend. The shiny watch he purposely checked every so often so that everyone around him would notice. But after ten years, the lifestyle had started to feel hollow, and Scott decided to join a humanitarian organization doing work in Africa called Mercy Ships. They sent doctors and nurses on floating hospitals to care for those who lacked sufficient access to medical care.

Scott was dispatched to Liberia after a bloody civil war. He was traveling with a group of much-needed volunteer doctors; Liberia itself had only one doctor for every fifty thousand people. The volunteers only had the time and resources for fifteen hundred operations, but seven thousand Liberians showed up in need of surgery.

Some of these people had tumors the size of cantaloupes in their throats that prevented them from breathing comfortably. Many wore towels over their faces because villagers thought the visible tumors meant they were cursed and so they threw rocks at them. In many cases, a forty-five-minute surgery could remove the tumors, but many patients would have to wait several months before receiving treatment.

When Scott asked how the tumors had developed, doctors pointed to the water. Many people were drinking from a brown swamp filled with leeches that stuck to the back of their throats. One remedy to remove these leeches was to drink diesel fuel—strong enough to kill the leeches, but not strong enough to kill the person doing the drinking.

Scott discovered that 80 percent of all diseases in the world were caused by unsanitary water. He learned that in parts of Africa, women were walking eight hours a day with pots filled with thirty pounds of water on their heads, just to have safe water for cooking and washing. He discovered that, for $65, a sand filter could make water drinkable. For $5,000, they could dig a freshwater well.

Scott returned to America, invited seven hundred people to a club using his old party promotion tactics, and raised $15,000—enough to build three wells in northern Uganda. Then he told everyone he didn’t want presents on his thirty-second birthday; rather, he asked his friends to donate $32 to his new nonprofit, Charity: Water. The response was overwhelming. Scott not only began to bring clean water to places in need, but with his massive Twitter following, he was able to reach a large audience and significantly scale his impact in a short period of time.

Scott’s story provoked the highly successful business owners in the room to reconsider their definitions of success. Was it making money? Or was it making a difference? Everybody who heard Scott speak was forced to look within themselves and question how they wanted to live their lives.

The next day, another speaker under the thatched roof continued to shake assumptions about life and business. By this point, most of the attendees had heard the premise behind author Tim Ferriss’s bestselling The 4-Hour Workweek: If you could free up your time and work remotely in a place where your dollars stretched a long way, your money would automatically be worth much more. While that extra cash was great, the real value was the ability to live as you wished.

Listening to Tim in person started to tear Elliott out of his childhood home and office in Washington, D.C. From that moment on, he knew that he wanted to travel the world. He wanted to explore. He wanted to grow Summit Series remotely. He looked over and saw the same reaction on Brett’s face.

Without quite knowing what he was doing, Elliott had created in Mexico what he had been looking for in college. When he had first arrived at the University of Wisconsin, he had loved the camaraderie of walking to morning classes, feeling the momentum of thousands of students moving in the same direction. It was the sort of energy a marching band tapped into as it headed into the stadium before a college football game.

But one day, on his way to class, Elliott turned and realized he was going exactly where everyone else was headed—to the same classes just to compete for the same jobs—and that thousands of students at other universities were doing the same thing. In that moment, Elliott realized he wanted to walk in the opposite direction.

In Mexico, he was surrounded by a community of people who were united by their values yet walking different paths. Scott and Tim were the teachers Elliott was looking for, and their stories were the classes he desired.

The event ended on the third day with a TOMS shoe drop at a neighboring village. TOMS had partnered with a school district that had a hundred kids wearing beat-up, torn footwear. A group of attendees set up stations, sat on milk crates, and measured the kids’ feet. Then they’d grab the right sizes and put the new shoes on them. Elliott looked at the faces of these kids receiving their new shoes and knew right then and there that he was not going back to his windowless office in D.C. to sell digital media space.

A seed was planted in his mind when everyone returned to the hotel. Lively conversations ricocheted around as attendees recounted the inspiring afternoon they had just experienced. The shoe drop had shown Elliott that there was more to business than the bottom line. That building a profitable company and giving back could coexist. He heard the same realization in the conversations around him and began to wonder if Summit Series could one day be the bridge that inspired company founders to want to do more good in the world.

There was no time to dwell on this thought as the energetic buzz of conversations among attendees continued through sunset and into a starlit night sky. Bonds were forming across the pool deck as guests told stories of their trials and tribulations, shared advice, and laughed with one another late into the evening. Finally, the dialogue came to an abrupt halt when Elliott shouted out the idea for a night snorkel. He had masks and fins waiting nearby on the beach, and soon attendees were running as fast as they could to dive into the water. As everyone floated under a vibrant full moon, they finally experienced the first quiet moment of the night.

The next morning, as the event came to a close and everybody checked out of the hotel, the goodbyes were filled with encouragement to take Summit Series further.

“I didn’t know what to expect, but I’ve gotta say, I had an amazing time and met some incredible people.”

“Let me know when the next one is—I have some friends I’d like to bring.”

It was all the encouragement Elliott needed to take the final leap and go all in on Summit Series. Back home, his dad’s company, Bisnow on Business, was going through a transition. They were hiring new employees and establishing a more professional-sounding name: Bisnow Media. Elliott sensed that it was time for him to evolve, too.

He knew that the life he was returning to would not be the same as the one he’d left. Brett knew he wasn’t going back to try to sell real estate during a mortgage crisis. And with Summit Series and Bisnow Media taking off, Ryan was ready to leave his day job.

To consider quitting your job in the middle of the global financial crisis would have seemed insane to most people. General Motors was about to go through bankruptcy and there were mass layoffs around the country. The economy was only getting bleaker, and any job seemed better than no job at all.

But Tim Ferriss had been quick to point out that Apple, FedEx, and Microsoft had all launched in a recession when the economic downturn produced discounted infrastructure, a sudden pool of talented freelancers, and bargain prices. There was no time to lose.

“Someday,” Tim loved to say, “is a disease that will take your dreams to the grave with you.”

This was the moment to think bigger.

Elliott, Ryan, and Brett were ready to double down and throw another event twice the size of the Mexico gathering.

But before they could go all in, they were going to need more help.

7 IF YOU WANT TO GO FAST, GO ALONE. IF YOU WANT TO GO FAR, GO TOGETHER

Over time, trust builds through actions and becomes sturdier, like wet concrete curing. But even after someone has proven to be honest or to give good advice, how do you know if they are the right partner for your company?

After the event in Mexico, Elliott was ecstatic about developing a company of easygoing yet purpose-driven people. It was the first time in his life that he was able to assemble a team, and as a way of helping him figure out who would be a good fit, he came up with a strategy that never would have lasted at a major corporation. The method came from the CollegeHumor guys who’d pranked him with that sartorial note in Park City.

It was a nineties throwback MTV video filmed with a cast of about fifty of Ricky and Josh’s young employees. Their team jumped up from their work desks, lip-syncing and dancing to the song “Flagpole Sitta” by Harvey Danger—I’m not sick but I’m not well / and I’m so hot / ’cause I’m in hell—ultimately falling to the floor en masse. It was a high-energy, overly dramatic pop punk spoof, but most of all, it gave the impression that there was no place CollegeHumor’s employees would rather be working than in their office.

“That’s what I want,” Elliott told himself upon watching the video. It became a tool for him to get a reading on anyone who saw it. He wanted to form a company where the work culture was just as important as the work they were doing. If someone loved the video as much as Elliott did, they were in.

Brett was also on the same page about the video—not to mention that he had over-delivered on sponsorship sales for the Mexico event. Brett had also realized that Summit Series gave him the opportunity to recruit friends he’d want to work with and be around all the time.

When Brett told Elliott he knew two people who’d be great additions to the team, Elliott immediately wanted to meet them. He trusted Brett implicitly because Brett had no filter or hidden agenda. On top of that, Brett had developed the ability to read other people through a simple philosophy:

Lead with generosity.

Generosity creates trust.

Trust creates productivity.

Brett’s litmus test was to watch and see if someone reciprocated the same level of generosity they had received from him. If so, he knew he could trust them.

This philosophy attracted the right kind of people to Brett, while his experiences in the college party scene allowed him to quickly detect shady characters. A recommendation from Brett meant a golden seal of approval, and Brett told Elliott that he had trusted Jeff Rosenthal from the moment they had met.

Brett was in college at George Washington at the time, and Jeff was less than four miles away at American University. Brett liked to say there are two priorities for college students. One is grades. The other is a social life. As budding entrepreneurs, Brett and Jeff had both figured out ways to make money off the latter.

They were throwing $10 cover-charge parties at clubs in the D.C. area when they met and combined forces to work on one of Brett’s events. Brett picked up on how Jeff genuinely cared for others and how that seemed to put him at the center of everybody. Jeff also noticed this trait in Brett.

The two had a phenomenal night, hitting the club’s capacity and bringing in a good chunk of money for themselves. Brett was so impressed with the way Jeff operated that he paid him way beyond their agreed-upon percentage in hopes that Jeff would want to partner again in the future.

And he did. Throughout their college years, Jeff brought American University students to Brett’s parties on Thursday nights, and Brett directed GW students to Jeff’s parties on Tuesday nights.

But their friendship soared beyond weeknight parties. They started to hang out on weekends and became close with each other’s families. They shared a similar thirst for life, but they were also different in many ways. Brett was a showman: high-energy, boisterous, clever, and funny. Jeff was more of an artist: laid-back and articulate, once taking a shot at the designer jewelry business. There was plenty of overlap, though, and they both felt the same initial reservations when they first met Elliott—though Jeff’s were more pronounced.

“That’s the guy?” Jeff had asked Brett after his first interaction with Elliott.

“That’s the guy,” Brett reaffirmed.

Brett vouched for Elliott because he’d realized that the qualities needed for success aren’t surface-level. So what if the guy didn’t seem to have an off switch? He delivered on what he said he was going to do, and he worked harder than anyone Brett had ever met.

In fact, during one of his first meetings with Elliott, Brett arrived at 8:00 a.m. to find Elliott already wrapping up a session.

“Impressive,” Brett said. “Nice to know I’m your second meeting of the day.”

“Actually,” Elliott pointed out, “you’re my third. I started with a coffee chat at six-thirty.”

Brett had seen what he needed to see in Mexico. Elliott had pulled together a gathering unlike anything Brett had ever experienced—and he was the one known for throwing semester-defining parties. He trusted Elliott.

Jeff had faith in Brett, but it was tough to extend it beyond that. Luckily for Elliott, Jeff saw a personal advantage to joining the team—one that allowed him to benefit from his superpower.

Jeff has the aural version of a photographic memory: He can remember things that were said to him in great detail—that is, if he’s paying attention. That’s because this blessing comes with a catch: ADHD. If Jeff was sitting in a classroom and didn’t care about the subject being taught, he couldn’t remember any of it; if he did care, he could quote the professor word for word months later. Even though he was smart, he struggled in school in subjects that didn’t fascinate him. He was a paradox: a solid C student who’d once skipped a grade.

Because he couldn’t learn traditionally, Jeff was almost completely reliant on taking in information through interactions with friends and mentors. His mind could replay the conversations that engaged him, almost verbatim, years later. He recognized that he needed to surround himself with people who could inspire him. And according to Brett, the Summit Series community would be filled with them.

Brett recounted the Mexico event to Jeff, highlighting all the amazing people he had just spent three days with—all the amazing people that Jeff could have an opportunity to talk with and learn from.

“So it sounds like,” Jeff asked Brett, “this is a skeleton key to reach out and call all the people I’d love to meet?”

“That’s right,” Brett assured him.

That was a lot better than his current job and start-up projects, which left him feeling alone and unfulfilled.

Next, Brett turned to Jeremy Schwartz.

Jeremy had been best friends with Brett since high school. He had a free-flowing, low-key, humble nature, and his rapport with Brett was similar to Jeff’s. He was also, in his own way, one of the most successful young businesspeople Brett knew.

Some people wouldn’t think of a band as a business, but Jeremy, along with his bandmate Spencer Charnas, had turned Ice Nine Kills into a much-loved commodity. They were not only writing music and running a music publishing company but had also built a loyal fan base around America, created a consistent brand that their generation identified with, and worked out how to make a band their full-time gig. What if Jeremy could apply the same lessons he’d learned touring the country to Summit Series?

Jeremy’s band was on the road when Brett reached out. He gave Jeremy a rundown of Summit Series’s next phase of growth and showed him press from the Mexico event. That piqued Jeremy’s interest. In the music industry, it felt as though everyone was trying to claw their way to the top, while at Summit Series, people were connecting, sharing, and collaborating with one another.

They had long joked that one day either Jeremy would join Brett’s future company or Brett would sing for Jeremy’s band. So in lieu of a traditional job interview, Brett flew down to Tallahassee, Florida, where Jeremy was playing a sold-out show, and they decided to see who would win out. Brett had been practicing the songs for a couple of months, and in the middle of Ice Nine Kills’s set, Jeremy pulled him onstage. Brett grabbed the mic and launched into a highly energetic performance, the crowd singing along with every word he belted out. While he definitely didn’t embarrass himself, it was clear to both of them that Brett wasn’t going to be a front man. Jeremy joining Summit Series seemed to be the more viable option.

Eager to learn more, on the next break from their tour Jeremy drove from his and Spencer’s recording studio in Boston to D.C. to stay with Brett. He wanted to give Summit Series a go.

When Jeremy arrived, his hair was falling past his shoulders and his left eyebrow was pierced. Brett looked at him and told him straight up that he couldn’t go into their meetings looking like that; he liked the look, but their less-liberal potential investors might not. If Jeremy wanted to join, he was going to have to cut his hair and lose the piercing.

Jeremy felt his stomach clench. He wasn’t prepared for this moment. It said: Your old life is over. A part of him wanted to say no. Wearing a suit and tie was counter to all the values on which he’d built his punk rock career. But Jeremy was tired of the grind of touring and was ready for something new.

The two went to the barber together. It was a rite of passage. Jeremy sat down in the chair with his hair looking like Jeff Spicoli’s in Fast Times at Ridgemont High. When he got up—well, his hair was still covering his ears, but hey, it was a clear sign of commitment.

Jeremy’s second test was joining Elliott for a meeting with a prominent magazine publisher with the hopes of getting press coverage for their next event. Even though Jeremy and Elliott had never met, Jeremy figured they would have to give the publisher the impression that they had a long-standing relationship.

“Elliott, great to see you,” Jeremy said as he walked into the room, patting him on the back affectionately. “How good was that dinner last night?”

“Oh my God, that grilled brick chicken was unbelievable,” Elliott fired back, playing right along.

They nailed the ruse—and the meeting. Elliott left the room immediately sold on Jeremy’s ability to think on his feet.

“But,” he said, “you’re gonna have to cut that hair.”

“But I just did!”

The team was formed. Everyone was excited to hit the road—all except Ryan.

Ryan had graduated from Northwestern, worked at Deutsche Bank, and landed a job at a top private equity firm. He wanted to be an entrepreneur and part of Summit Series—but he also wanted to run a business from a fixed office with an established home. So Ryan began to straddle two jobs: running operations for Summit Series and being Bisnow’s CEO, which was expanding from D.C. to New York City, soon Chicago, and eventually twenty-eight more cities.

This actually ended up working out in everyone’s favor. Elliott gave up his position at Bisnow Media to Ryan. In doing so, it liberated Elliott to head out into the world with Brett, Jeff, and Jeremy to grow Summit Series.

There was just one question left: Where would we go?

It was the dead of winter in early 2009, and D.C. was miserably cold. We were fantasizing about sunnier climates around the world, but at the time we could barely afford to shell out enough for dinner, let alone four international plane tickets. Then, in yet another stroke of luck, Brett stumbled across the perfect alternative.

“I have some great news that’s going to change our lives,” he said. His grandmother was offering us her two-bedroom condo on a nine-hole golf course in Boca Raton. It was in an age-restricted community, sure, but as long as we pretended like we were her guests, everything would be golden. “That means that the four of us can get out of this cold weather and have our own home in sunny Florida for the next four months to do whatever we want.”

Never mind that we’d be the youngest people in this community by a good fifty years—it was a chance to downsize, live cheaply, and pour ourselves into our new business, all while living poolside. The four of us celebrated, and, with a final nod to Tim Ferriss, decided to reduce what we owned down to one carry-on suitcase each. We donated our furniture to Goodwill. There were only a few remaining pieces in Brett’s D.C. apartment when he ceremoniously karate-chopped through a flimsy desk. The chop felt like breaking through an old way of life. Bye-bye, desk. Bye-bye, office. Bye-bye, city.

We were four guys in our early twenties with no big-business experience, no savings, and no fear. The recession might have demolished our chances of stable, traditional careers—not that we would have been satisfied with day jobs anyway—but it also gave us the chance to create a new kind of community out of the rubble. This kind of naive bravado is the type of lucid insanity many start-ups need to get themselves off the ground—to deny the sensible option and choose the most outlandish one instead.

And quite often, with that kind of a giant leap, you’re ripe to make a big mistake.

8 REPUTATIONS ARE EARNED BY THE DROP AND LOST BY THE BUCKET

It felt like we were gaming the system. We were supposed to have jobs, but instead we were building a company while sitting poolside in the subtropical Florida air. Granted, it was a pool at a retirement community, and the four of us had to share two beds. But we had our own house, it was sunny, and we had a body of water to jump into as we planned our future.

The community we moved into felt like a scene out of Pleasantville. We were surrounded by perfectly manicured lawns, gnomes in front gardens, and quilts on porches. There was a hushed silence by the pool while octogenarians played backgammon—a serenity we broke when we began making phone calls.

We wanted the next Summit Series event to show a level of sophistication that we definitely didn’t embody. So we pushed ourselves to elevate the experience.

We landed on a ski weekend in Aspen at the stately St. Regis. The luxury hotel is part of a renowned chain spanning the globe that was started in New York back in 1904 by John Jacob Astor IV, one of the wealthiest men on the planet at the time. At the Aspen St. Regis, the bathrooms were all marble. The linens had a thread count of four hundred. They used a saber to open bottles of champagne. There was even butler service.

No more summer camp. That vibe may have worked at our past two events, but we felt it was time to step it up.

Truthfully, we didn’t even have the money to go to Aspen to check it out. So we booked the hotel’s ballroom and some restaurants in town, sight unseen, from our poolside cabana. We didn’t gut-check any of this with our former attendees—we were excited, so we figured they would be, too.

The problem was, there was simply no way we could continue to offer a free event, especially with the global economy plummeting. Based on the crowd we’d pulled for the last two events, we got GQ to put up a little money to co-host Aspen, but because we were now in the middle of a recession, there were very few sponsors willing to chip in. We were on the hook for hundreds of thousands of dollars and could no longer cover losses of that scale with credit cards.

For any business, there’s a critical point when founders must decide to monetize their company. Many organizations establish a revenue model right out of the gate and start charging for its product from day one. The downside of this strategy is the risk of turning away your customers before they’ve even had a chance to experience what you’re offering. Another effective strategy is based on the concept of “try before you buy.” It’s why the “freemium” model works so well for many digital products. It’s why Costco doles out free samples of pizza rolls in front of the frozen food section. Summit Series was no different. We had given people a taste of what we were offering, and they had liked it. So we figured we could now start charging people to attend, and establish our revenue model based on ticket sales.

We figured that most of our audience could afford a $3,000 ticket. After all, they were some of the most successful young business leaders in America. They’d gotten great value from the earlier events, and they trusted us to deliver on our promises. We assumed they’d find the value of the relationships they’d forge well worth the ticket price.

What we didn’t realize was that it’s hard for people to be critical of your product when they’re getting it for free. Elliott had received nothing but hugs and high fives at the close of the first event in Utah. Brett had heard only praise in Mexico. And Jeff and Jeremy knew only what they’d been told—that nearly every attendee was thrilled with their experience.

Because we assumed that everyone loved what we did, we didn’t feel like we had to seek out advice or get feedback from past attendees on if they would be willing to pay to attend. We decided to push forward without consulting anyone.

Elliott drafted an email with complete confidence that we’d sell out in a few days. He sat by the pool, shirtless, tapping away on his laptop. “All right, are you guys ready to watch hundreds of thousands of dollars flow into our bank account as soon as I hit send?”

He glanced at his email one last time and smiled.

We’ll have 125 of the most influential people in America under 35 years old.

We are not releasing a list of people who are booking or have booked due to the high profile of attendees on the trip.

Elliott liked an invitation he’d seen to a party in Washington that came with three rules as an homage to Fight Club, and he’d lifted the format. It was the perfect formula to bury the fact that attendees would have to pay for their own tickets.

There are 3 rules for Aspen 09:

1. Don’t tell anyone about Aspen 09.

2. There are no comped tickets.

3. Don’t tell anyone about Aspen 09.

“See ya in Aspen!” the last line read, along with a link to the website where attendees could purchase their ticket for $3,000.

Elliott looked up. “Ready, gentlemen? Here’s to a bold future!”

Then he hit send on his computer and let it fly.

Elliott’s enthusiasm was contagious, and the four of us, feeling satisfied with ourselves, decided to celebrate by hitting the golf course for the afternoon. But before we could even pack up from the pool, we got our first call. We picked up the phone fully expecting it to be an excited invitee ready with their credit card details.

We couldn’t have been more wrong. The person on the other end of the phone was so upset about our terrible communication that he felt compelled to call us rather than type an email.

“This is offensive. You traded on our names for your own profit.”

We thought that maybe this was just one outlier, a single disappointed customer in a sea of happy campers. But then the emails started rolling in.

“You should really evaluate how you do business.”

“Thanks, but no thanks. I’m definitely not coming.”

And those were just from the folks who felt compelled to tell us how badly we’d screwed up. Many didn’t bother to respond at all.

Maybe they hated the smug tone. Maybe they hated our Fight Club reference. Maybe they felt we sounded entitled or tone-deaf. We quickly realized they mostly hated that we’d sprung such a big change on them without explaining why. The last two Summit Series events had been free, and here we were demanding that everybody pay $3,000 for the privilege of continuing to attend.

Some people in the community saw the email for what it was—a novice mistake. But perhaps our most egregious offense was making people who cared about us feel like they were the victims of a bait-and-switch after they’d turned over the personal contacts of their closest friends.

As waves of guilt and anxiety crashed down upon us, we scrambled to send a follow-up email to try to smooth things over, explaining why we could no longer sustain Summit Series events without charging. But it was too late.

The situation only deteriorated. One of the recipients leaked our email to Gawker, which put us on the front page of their website under the headline “The $3,000 Invite for Startup Founders’ Ski-Bum Party.”

We moved through our own stages of grief: from disbelief to panic, and then to anger, devastation, and finally acceptance.

We decided to push forward, but after many days, we’d sold only ten tickets—which was miraculous in its own right—and we were running out of time to cancel our contract with the St. Regis. Our fear that we had lost our community’s trust was now turning into financial fear, too.

Ryan called in from D.C., pragmatic but not pleased. “Look,” he said, “we’re going to take a bath on this thing. We should exercise our attrition clause with the St. Regis to reduce our exposure.”

He took it even further, suggesting we consider the possibility that the business model might not be viable. Offering a free party was one thing. Selling $3,000 tickets to an event was entirely different. He recommended a sensible retreat for all of us back to Bisnow Media.

“My sister in Westchester County just got a black Labrador and they have extra puppies,” he said. “If we exercise our attrition clause, we’ll all have money to get some dogs.”

None of us in Florida were ready to concede. But we had to consider Ryan’s view. Our community (if you could even call it that at this point) was upset. They felt betrayed. They felt we had pulled a fast one on them. Maybe this just wasn’t going to work.

Elliott felt so guilty about the email that he seriously considered shutting everything down. If he’d been the only founder, there’s a good chance he would have. But that was the beauty of partnership.

Brett looked over at Jeff and Jeremy. He’d recruited them. He’d asked Jeremy to ditch his aspirations as a musician and join the team. And what was Jeff supposed to do now, go back to Macy’s? And where was Brett going to find real estate work in the deepening recession?

The more Brett thought about it, the more adamant he became. This is what I’ve wanted. I’ve wanted to make it on my own, not spend my days working for a corporate entity. I put myself on the line to recruit the people who I wanted to spend my time around. We’re all in this together now. This is what I want to fight for.

“Fold this epic business idea with so much potential just so we can go get some puppies?” he asked.

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