Capítulo 4
Imperfection: The Beauty of Authentic Experiences
As the entrepreneurs arrived at the Utah ski house, disaster struck immediately. Elliott's rental van got stuck in the snow, and a police officer approached as his guests tormented him with jokes about going to jail. After receiving a ticket, the heckling continued all the way home, creating an unexpected bonding experience better than anything Elliott could have planned.
The next day on the slopes, entrepreneurs like Sam Altman and founders from Vimeo and TOMS swapped stories about their struggles and failures, forming lifelong friendships. Elliott realized his biggest lesson: perfection isn't necessary for success. The most important quality of an event is space for unplanned moments that create genuine connections. It's like the difference between a polished supermarket apple and a slightly bruised organic one that tastes infinitely better.
This philosophy of embracing imperfection would become central to Summit's approach. Years later, during their Summit at Sea event, their carefully planned Wi-Fi system failed five minutes after leaving shore. What seemed like disaster became serendipity - guests approached them appreciating the forced disconnection from technology. This "failure" became their new motto: "There's no Wi-Fi where we're going, but we promise you'll find a better connection."
Similarly, when organizing a White House symposium for forty influential CEOs, they had just four days to arrange everything. Despite the pressure, they focused on creating authentic connections rather than flawless logistics. The result was so powerful that Twitter CEO Evan Williams tweeted about the event, causing interest to explode and even top White House officials to demand invitations.
The Summit founders discovered that polished corporate events often feel sterile precisely because they eliminate the human element of imperfection. By contrast, their willingness to embrace the unexpected created spaces where people could be authentic, vulnerable, and form genuine connections that transcended networking.
Capítulo 5
Partnership: Combining Strengths to Overcome Weaknesses
As Summit began to grow, the founders recognized that their individual weaknesses could be offset by each other's strengths. Brett Leve's background perfectly complemented Elliott's vision. Growing up working at his father's gas station six days a week, Brett developed strong sales skills from an early age. His extroverted nature served him well behind the counter, selling Cutco knives in high school, organizing college parties, and later in land development.
When Jay Baitler of Staples agreed to a call, Brett wasn't nervous at all. He pitched confidently about how Summit Series would connect Staples with influential millennials building world-class organizations. Though Jay seemed skeptical, Brett persisted, explaining how this small investment could lead to valuable business relationships. When Jay unexpectedly offered $30,000-triple what Brett expected-he seized the opportunity, naming the event "Staples Young Leaders Summit."
This partnership approach extended beyond the founding team. After the White House event gave them renewed motivation and credibility, they focused on their struggling Aspen event. Their game-changing connection came through Elizabeth Gore from the UN Foundation. Elizabeth mentored them, introducing female speakers like FEED co-founders Ellen Gustafson and Lauren Bush, and suggesting they auction dinner with Ted Turner to benefit the Nothing but Nets anti-malaria campaign.
Elizabeth saw value in connecting her UN Foundation work with Summit's entrepreneurial network-merging her methodical approach with their "sewing parachutes on the way down" energy. She also introduced them to Mikkel Vestergaard Frandsen, designer of life-saving mosquito nets, creating a powerful collision between technology and social justice that would define Summit's future direction.
The founders learned that true partnership isn't just about dividing tasks according to skills-it's about creating something greater than what any individual could accomplish alone. By bringing together people with different perspectives, experiences, and talents, they could tackle challenges that would have been insurmountable otherwise.
Capítulo 6
Purpose: Finding Meaning Beyond Profit
At Playa del Carmen for their second Summit Series event, Elliott marveled at the resort's beauty while guests were surprised to discover they had roommates-Elliott's intentional "summer camp" strategy for connection. The event began with Scott Harrison sharing his journey from nightclub promoter to humanitarian. After witnessing the devastating health effects of unsanitary water in Liberia, Scott founded Charity: Water, using his promotional skills to raise funds for wells in Africa.
Scott's story challenged the entrepreneurs to reconsider their definition of success-was it making money or making a difference? Tim Ferriss followed, discussing his "4-Hour Workweek" philosophy that inspired Elliott to envision working remotely while traveling the world. The event culminated in a TOMS shoe drop at a local village, where attendees fitted underprivileged children with new footwear. This experience planted a seed in Elliott's mind that businesses could be profitable while giving back.
This focus on purpose became even more pronounced after their Miami event, when Jeff visited Uganda to see firsthand how the money they'd raised for Invisible Children would help communities affected by what the UN called "the world's largest neglected humanitarian emergency." Uganda had endured a devastating civil war that displaced millions, followed by the violent campaigns of warlord Joseph Kony's Lord's Resistance Army, which abducted 30,000 children and killed approximately 100,000 people.
Jeff's experience in Uganda showed him the stark realities of humanitarian work-seeing warehouses of donated food sitting unused while nimble entrepreneurs were making real impact. This insight was reinforced when Ann Veneman, UNICEF's executive director, advised them that money alone wasn't the solution, pointing out that despite a trillion dollars flowing into Africa over thirty years, poverty had increased. She encouraged them to leverage their network's talent rather than just fundraising.
Their perspective was further transformed when they witnessed Haiti's devastating 2010 earthquake firsthand. Despite bringing school supplies and LifeStraws for water purification, they felt helpless against the catastrophic destruction-toppled buildings, tent cities, and overwhelming human suffering. This experience made them reconsider how their community could meaningfully address global challenges beyond traditional charity.
Capítulo 7
Community: The Art of Bringing People Together
After the White House event, the founders established two simple criteria for future Summit attendees: Do they do innovative work in the world? And are they kind, open-minded people with a desire to grow? This clarity of purpose transformed Summit Series from a series of events into a true community with a mission they could articulate and believe in.
Tony Hsieh of Zappos had asked them a transformative question: "Are there people at this event who you wouldn't invite to your parents' home for dinner, if not for their professional success?" His insight that culture trumps everything else in community-building changed their trajectory. They realized that the quality of connections mattered more than impressive titles or company valuations.
This philosophy was put to the test when they made a counterintuitive decision to scale back their event from 1,400 to 800 people at Squaw Valley in Lake Tahoe, calling it Basecamp. This defied conventional event business logic-festivals typically aim to grow, not shrink. But remembering Tony Hsieh's advice about prioritizing community culture, they chose return on community (ROC) over return on investment (ROI).
Their approach to community-building reached new heights when they moved into an 18-bedroom house on the Malibu coastline. Despite its dated interior with orange carpet and chipped paint, they transformed it into their headquarters and began hosting twice-weekly dinners for a hundred guests-an approach that would become their most powerful relationship development engine.
These Malibu dinner parties evolved into a sophisticated art form under the guidance of Michael Hebb, famous for creating unique dining experiences in unconventional locations. They grew equally intentional with their guest lists, organizing each dinner around a theme rather than simply inviting friends they hadn't seen recently. They learned that diverse attendees created more complex conversations and better experiences.
Their "barefoot hospitality" approach made these gatherings unique. Despite hosting up to a hundred guests twice weekly, they had only one chef with no additional staff. They served family-style meals, asked guests to make impromptu toasts about their passions, and created a sense of ownership by having everyone clean their own "box" (the space in front of them) afterward.
These dinners featured extraordinary moments-like when Leslie Odom Jr. sang four years before Hamilton reached Broadway, or when Radiohead's Thom Yorke spontaneously played piano after excusing himself from the table. By perfecting this format, they created a portable community-building tool they could deploy anywhere, transforming ordinary gatherings into once-in-a-lifetime experiences.
Capítulo 8
Vision: Creating a Permanent Home for Ideas
Sometimes a seemingly ordinary coffee meeting can change everything. When Elliott met venture capitalist Greg Mauro in August 2011, their scheduled hour-long chat stretched to eight hours. Unlike most people focused on talking about themselves, Greg genuinely wanted to explore the same question the founders had been pondering: What more could Summit be?
They'd been wrestling with this since moving to Malibu. Their community was connecting between events, and their Tuesday and Thursday dinners showed them the power of consistent gatherings. They sensed they needed something permanent-not just a rented beach house, but a true home for their community.
Greg initially suggested a club in San Francisco where entrepreneurs could meet instead of coffee shops. During their conversation, Greg mentioned he spent winters in Eden, Utah, near Powder Mountain-what he considered North America's best ski resort. Most importantly, he revealed the entire resort was for sale.
When Elliott shared this with the team, Brett and Jeremy immediately recognized the name. Years earlier, Brett had heard about Powder Mountain's legendary status from a fellow traveler. Within 36 hours, they were on a plane to Utah, having no idea what they were getting into or how much a mountain might cost, but determined to follow their instincts.
The mountain had been started by Alvin Cobabe, a doctor who came from sheepherding stock and built the first lift in 1972, maintaining a quaint, magical atmosphere summarized by his motto: "You're only a stranger once." After changing hands multiple times since 2006, the mountain was now controlled by a private equity firm planning to build nearly 3,000 large houses, install high-speed lifts, and add a golf course. Eden's 600 residents were fighting these plans in court, determined to protect their hidden gem.
The founders sketched ideas for a completely different approach-limiting development with small, eco-friendly homes and creating a walkable village for a global community rather than importing thousands of seasonal outsiders. This unique outlook made institutional financing impossible, as they weren't maximizing density. When Greg finally called with news that they could buy the mountain for $40 million, they knew this was their moment to act-despite having only $1 million in the bank.
Capítulo 9
Persistence: Turning Impossible Dreams Into Reality
Oscillating between unbridled enthusiasm and overwhelming anxiety, the founders faced the impossible: their company had only $1 million in the bank, yet they needed $40 million to buy a mountain. If sophisticated investors were throwing in the towel, who were they to think they could succeed?
They developed a "founding member program" similar to those used in golf communities, where members would put money into an escrow account for homesite credits. Only after reaching specific milestones-$20 million in escrow, county approval, and completed entitlements-would funds be released as a down payment, with the remaining $20 million paid over time.
Rather than presenting their plan via PowerPoint at Basecamp, they organized a mini-event at Powder Mountain for sixty core supporters, arranging for a specially built hut on skis (to comply with zoning regulations) and chartering a 737 to transport guests directly from Tahoe to Utah. They invited these supporters on an all-expenses-paid weekend to a "surprise destination," promising an experience that would showcase their vision in a way no presentation ever could.
After their successful Powder Mountain reveal, they felt momentary relief-like turning in a final exam. But unlike high school, they couldn't relax. With their $20 million deposit due in less than six months and having never raised more than $1 million before, they knew they had no time to waste.
They transformed their 15,000-square-foot mountain cabin into their home, office, and hosting space. Building on the success of their initial sixty-person weekend, they expanded to hosting two hundred people every weekend. They'd bring guests to the mountain summit at sunset to share their vision, then return to serve farm-to-table dinners with locally-sourced ingredients.
Despite refining their pitch every weekend, everyone declined to invest. Then Matias de Tezanos, a successful entrepreneur from Guatemala, shocked them by immediately committing $2 million after hearing their vision. "As an entrepreneur, nobody actually believes in you at the very beginning when you need it the most. So I'm going to be that person," he explained.
With seven days remaining before their final deadline, they converted a small room in the lake house into their "peace room"-a 24-hour command center with whiteboards tracking progress across three walls. The process wasn't heroic or smooth-it was messy. People promised to sign documents then announced they were turning off their phones for family trips. They'd receive signed papers only to discover missing signatures on page thirty-seven.
Remarkably, they exceeded their $20 million goal, securing over $30 million in escrow in less than seven days-a testament to their community's trust. On April 24, 2013, Elliott signed countless documents until his hands blistered, and afterward, rather than celebrating extravagantly as they typically would, the four founders simply sprawled across couches in the lake house, too exhausted to speak, silently acknowledging what they'd accomplished.
Capítulo 10
Legacy: Building Something That Outlasts You
As entrepreneurs, the Summit founders faced a fundamental dilemma between capital and responsibility. Bootstrapping means disappointing only yourself if you fail, but raising money means becoming responsible for others' dreams and investments. At Summit, they'd always bootstrapped until Powder Mountain forced them to seek outside investors-forty founding members who believed in their vision of a utopian mountain village.
They severely underestimated what bringing this vision to life would require. Their decade of experience producing multi-day events hadn't prepared them for master-planning an entire town at 8,000 feet elevation. The development process was humbling-like pushing a boulder uphill for years, knowing they couldn't stop or it would roll back down, growing heavier each time.
These challenges became their greatest teachers, improving them as entrepreneurs, communicators, and partners. As Summit matured, they discovered that behind-the-scenes mundane work was just as crucial as high-risk behavior. They learned to slow down, be methodical, trust experts, and admit weaknesses.
Their personal lives evolved too-Jeff, Elliott and Jeremy all met their wives through the Summit community, with Jeff and Elliott becoming fathers. Brett planted deeper roots in Eden, buying a home near his parents. They remained true to their vision, preserving Powder Mountain's small-town charm while building public trails and improving the ski experience without crowds.
By 2020, Summit had reached new heights-hosting sophisticated events, generating record revenues, facilitating their largest donations, and creating innovative plans to scale exponentially. Their community had evolved to include equal gender representation, criminal justice reform initiatives, and fellowship programs for young entrepreneurs. They had created programs for the unhoused and launched a Criminal Justice Policy Lab examining inmate treatment.
When the pandemic hit, it felt like they were back to square one fighting for survival. But drawing on their decade of experience and mentors, they approached the challenge with a beginner's mindset, excited to brainstorm solutions. They knew that no matter what problem might arise, they were only an idea away.
The Summit story isn't just about four friends who bought a mountain-it's about the power of community to transform individual dreams into collective reality. It's about creating spaces where people can connect authentically, challenge conventional thinking, and collaborate on solutions to complex problems. Most importantly, it's about making no small plans-because life is too precious to waste on anything less than extraordinary.
