Mark: Most business books tell you to have a bulletproof plan. Today, we’re talking about a book that argues the opposite: your greatest successes might come from your most spectacular failures. The secret isn't perfection; it's a glorious, well-intentioned mess. Michelle: Oh, I love that. The pressure to have everything figured out before you start is paralyzing for so many people. A glorious mess sounds so much more achievable, and honestly, more fun. Mark: Exactly. And it’s the central, beating heart of the book we’re diving into today: Make No Small Plans: Lessons on Thinking Big, Chasing Adventure, and Building a Community. It’s written by the four co-founders of Summit: Elliott Bisnow, Brett Leve, Jeff Rosenthal, and Jeremy Schwartz. Michelle: And what’s so wild about their story is the context. This wasn't a well-funded Silicon Valley venture. Mark: Not at all. It's the story of four friends in their early twenties who started this whole thing during the 2008 financial crisis with zero event experience, sleeping on bunk beds in one of their grandmother's condos in a Florida retirement community. Michelle: That’s incredible. They went on to create what people have called the "TED meets Burning Man" of conferences, hosting everyone from Jeff Bezos to Kendrick Lamar. So, let's start there. What does a "glorious mess" look like in practice?

Mark: It looks like their very first event. After one of the founders, Elliott, tried to organize a ski trip and got rejected by all twenty people he invited, he realized he needed a more inspiring idea. So he regrouped and managed to convince nineteen young, impressive entrepreneurs—founders of companies like TOMS Shoes and CollegeHumor—to come on a ski trip to Utah. All expenses paid. Michelle: Okay, so far that sounds pretty good. Where does the mess come in? Mark: Everywhere. He’s never planned an event in his life. He shows up and buys what he thinks is a ton of beer—it’s gone in an hour. The first night is painfully awkward. These are nineteen strangers who are all successful, probably a little arrogant, and they're all looking at each other wondering what this is. The book describes the vibe as deeply uncomfortable. Michelle: I can feel the second-hand cringe. So what happens? Mark: The founders of CollegeHumor decide to break the ice with a prank. They conspire with the restaurant's maître d' to deliver a note to Elliott, the host, on a silver platter. The note says his attire—a simple hoodie—is inappropriate for the club and he needs to change immediately. Elliott is mortified. He turns beet red, stammers an apology to his guests, and runs out of the room to change. Michelle: Oh, that’s brutal. Mark: But when he comes back, the entire room erupts in laughter. The prank completely shatters the tension. Suddenly, they’re not just a room of posturing entrepreneurs; they’re a group of friends teasing each other. But the real bonding moment came later that night. Elliott is driving a few of them back, makes an illegal turn, and gets pulled over by the police. Michelle: No! With a car full of these high-profile founders? That's a nightmare. Mark: A complete nightmare. And his new friends, instead of helping, start making it worse—joking to the officer, "He's been drinking all night!" The book says this moment, this shared, vulnerable, slightly chaotic experience, was a better bonding exercise than anything he could have possibly planned. It was an initiation. The lesson they learned was that authenticity trumps perfection. The unplanned, imperfect moments are where real connection happens. Michelle: That makes so much sense. The polished, perfect version is forgettable. The story you tell for years is the one where the host gets pranked and then pulled over by the cops. But that sounds like a happy accident. What happens when the mess isn't so glorious? When it's just a straight-up failure? Mark: That happened too. Their next big event in Aspen was a catastrophe. They’d had some success, gotten a little cocky, and decided to start charging—three thousand dollars a ticket. They sent out this smug, secretive email with a 'Fight Club' theme, saying the first rule of the event is you don't talk about the event. Michelle: Oh no. I can see where this is going. Mark: The community hated it. They felt like they were being sold out. Someone leaked the email to the media blog Gawker, which ran a story mocking them as entitled party boys. Their reputation, which they'd built drop by drop, was lost in a bucket. Michelle: Okay, that’s not a glorious mess. That’s a reputation-destroying disaster. How do you possibly recover from your own community turning on you like that?

Mark: You recover by cashing in on a different kind of currency. This is where we get to their second big idea: becoming a "favor economy millionaire." The principle is simple: you build a community not on transactions, but on trust and generosity. You give without expecting an immediate return. Michelle: That sounds nice, but a little idealistic. How does that actually work when your company is on the brink of collapse? Mark: The perfect example is what happened right after that Aspen disaster. They were broke and their reputation was in tatters. Then, out of the blue, Elliott gets a meeting with a guy named Yosi Sergant, who worked in the Obama administration. Yosi had a huge problem: he was tasked with putting on a White House symposium for young entrepreneurs to address the economic crisis. His deadline was in one week, and he had no budget, no speakers, and no attendees. Michelle: That sounds impossible. Mark: Elliott, with no money and no real plan, just says, "We'll do it." The Summit team then spent the next four days calling in every single favor they had. They leveraged the goodwill they had built. They called every impressive person they knew and said, "The White House needs you." They co-opted the ultimate brand—the White House—and it worked. They filled the room with 35 incredible founders. Michelle: That’s an amazing turnaround. But I have to push back a little here, because this is a critique I’ve seen from some readers. The book has this very energetic, "we did it" tone, but it's a story about four young, well-connected men. Does this "favor economy" work for everyone, or is it a bit of a romanticized way of describing a boys' club? Mark: That’s a very fair point, and something the founders themselves had to confront. In the book, they admit that their early events had a huge gender imbalance—fewer than 20% of attendees were women. They realized their network was a reflection of themselves. Their solution wasn't just to invite more women, but to fundamentally change their approach. They started by hosting an event exclusively for female entrepreneurs and, more importantly, they started listening. They learned, as they put it, to "create space for others" and realized that informed critique was the greatest gift they could receive. So while it may have started from a place of privilege, their growth came from recognizing and trying to correct it. Michelle: I appreciate that they acknowledge that. It adds a layer of self-awareness. But still, a one-off event at the White House is one thing. Can this favor economy really scale to something huge? Can it, say, buy a mountain?

Mark: That is the forty-million-dollar question. And their answer was to stop thinking realistically and start thinking surreally. They realized that to stand out, they couldn't just host another conference in a hotel. They had to create an experience that was completely different. Michelle: And this is where the cruise ship comes in. Mark: This is where the cruise ship comes in. The idea for "Summit at Sea" was literally born as a joke on a houseboat in Amsterdam. They said, "What if we just chartered a cruise ship?" The more they thought about it, the more brilliant it seemed. A self-contained, floating city where everyone is together for three days. No one can leave. It forces connection. Michelle: It’s a captive audience. Mark: Exactly. And they leaned into the "glorious mess" philosophy again. On the first Summit at Sea, the custom-built intranet they'd spent a fortune on completely failed right after the ship left port. Total disaster. Everyone was furious. Michelle: Of course! People need to be connected. Mark: But after a few hours of panic, something shifted. People put their phones away. They started talking to the person next to them. They were present. The failure became the event's greatest feature. Their new motto became: "There's no Wi-Fi where we're going, but we promise you'll find a better connection." Michelle: Wow. They are masters at honoring the error as a hidden intention. It’s the same principle as the disastrous first ski trip, just on a massive, 14-story scale. Mark: And that surreal ambition is what led them to their biggest plan of all: buying Powder Mountain, the largest ski resort in the U.S., for forty million dollars. They had about a million in the bank. Michelle: That’s not just ambitious, that's delusional. How? Mark: By applying all these lessons at once. They created a "founding member program," a creative financing model where they sold homesite credits to their community. They leveraged the favor economy to get advice from the best in real estate and finance. And they embraced the surreal nature of the goal. As Ted Turner told them at one of their events, in a quote that feels like the book's thesis: "Don't worry about making mistakes when you're making history."

Michelle: So when you put it all together, what's the real takeaway here? It feels bigger than just "dream big." Mark: It is. I think the deepest insight is that audacious goals create their own gravity. A small plan, like hosting a slightly better conference, is boring. It’s safe. But it doesn’t inspire people to help you for free, to invest millions of dollars, or to forgive your spectacular failures. Michelle: Right, nobody is going to rally around a plan that’s just ‘fine.’ Mark: Exactly. A surreal plan, like building a city on a mountain, forces creativity. It builds a tribe of people who want to be part of something legendary. The very absurdity of the plan becomes its greatest asset. It filters for the right kind of people and gives them a story to tell. Michelle: So the lesson isn't just to have a crazy idea, but to have the courage to share it. To not be afraid of the execution, because that’s where the community and the real magic happens. You have to be willing to look a little foolish. Mark: You have to be willing to look very foolish. And to trust that if your vision is compelling enough, people won't just watch you build it; they'll hand you the hammer. Michelle: It’s a powerful idea. It makes you look at your own ambitions differently. Mark: It really does. It makes you wonder, what's the 'small plan' in our own lives that we could make just a little more surreal? Michelle: A question to ponder. Thanks for the amazing stories, Mark. Mark: My pleasure. This is Aibrary, signing off.