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Airbnb Co-founder Joe Gebbia’s “Gym of Entrepreneurship”

From the “trough of sorrow” to an IPO, the entrepreneur, philanthropist, and Airbnb co-founder takes Rich Kleiman through his professional journey so far on the latest “Out of Office.”

Click here to listen to the full episode.

When Joe Gebbia is asked about when he first identified a sense of entrepreneurial spirit, he pointed to two unlikely scenarios:

First, to his second-grade hustle peddling his Teenage Mutant Ninja Turtles art to his classmates for one dollar a pop.

Second, forming the first-ever basketball team at his alma mater, the Rhode Island School of Design: the RISD Balls.

While both endeavors were short-term successes, Gebbia knew early that they were just the beginning of a priceless business training that would prepare him for what was to come, as he explained to Rich Kleiman and Gianni Harrell on the latest episode of Boardroom’s “Out of Office” podcast.

Growing up in Georgia, he watched his parents go through the trials and tribulations of self-employment, and was as inspired by their success as he was curious about their struggles.

“I got to see them forge their own path. I got to see them make their own success — or not… I saw them have good months, I saw them have bad months, and there was something incredibly inspiring about their work ethic and just the way they applied themselves. I just thought to myself, one day, I want to work for myself,” Gebbia recalls.

By the time he got to RISD, where he studied industrial design, he found himself playing with the ideas of possible businesses with increasing frequency. When people think of RISD, they think of its world-class art and architecture programs, but for Gebbia, the school was a “petri dish” of innovation.

“Art school is training to be an entrepreneur. I’ll tell you why: You go to art school, you study design. You have to imagine something that doesn’t exist. And you have to figure out how to make it, you have to figure out how to build it, have to solve a problem.”

It was while working there one summer that he was paired with Brian Chesky, with whom he would completely disrupt the travel industry less than a decade later.

Over those few months, Gebbia and Chesky played endless rounds of ping pong together, which felt like a perfect physical analog to the conceptual back and forths that drove their projects forward.

Though the wild strategic shifts that they proposed to Conair fell on deaf ears, Gebbia reflected on their time together, telling his partner, “‘I’ve just had so much fun with you. The project that we did for Conair, we knocked out the park… I just have this feeling that one day, you and I are gonna start a company together.'”

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Fast forward a few years later. While Gebbia was embedded in Silicon Valley — within what he called a “gym of entrepreneurship” where he got in some early reps on starting business ventures and building up his entrepreneurial muscles — Chesky was in Los Angeles. And after some hearty negotiations, he finally convinced Brian to move north.

For what? Well, that was yet to be seen.

Just days after Chesky left behind LA life, Gebbia’s landlord upped their rent and without any solid income, the two were left in a lurch. Their predicament proved to be a flicker of inspiration that sparked what we know now as Airbnb.

Gebbia shares how opening up their apartment to accommodate a housing shortage during a major design conference inspired the first traces of the business model for the company that now boasts a market cap near $100 billion.

The company experienced more downs than ups in the early days, but it was the passion of Gebbia, Chesky, and third co-founder Nate Blecharczyk that kept things moving forward.

Gebbia recalls several times throughout his career when he had an incredible idea, but lacked the resources to make it come to life. It was that same sense of passion that generated buy-in from those who could help him. More than once, after relaying his ideas, potential collaborators followed up with: “You really want this. Don’t you?”

And together, they made things happen.

For Airbnb, the transition from a feisty startup to a global brand came when the founding team got the chance to pitch themselves to Paul Graham for an opportunity to join the esteemed Y Combinator accelerator program.

After their pitch got interrupted early when Graham called their model “weird,” Gebbia seized the opportunity to leave behind a physical artifact of their digital product: boxes of Obama O’s and Cap’N McCain, novelty cereals that they produced during the 2008 election. Those boxes had funded the company’s first “Visa round,” netting $20,000 in sales to offset the credit card debt that was an inevitable by-product of their early days.

The last-ditch effort — and the fact that they had funded their development on the cereals — left a mark on Graham, who then accepted the fledgling start-up to the Y Combinator.

While a part of the program, Gebbia recalls that unlearning what they thought they knew about business proved to be as important as the formal training they received. One day Graham was looking at their user numbers when he challenged them:

“‘So, your customers are in New York City? But you’re here in Mountain View.’ And we’re befuddled. We’re like, ‘Yeah. We’re here for your program.’ And he goes, ‘What are you still doing here? Go to New York. Go meet your people.’ And in that moment, he broke through the myth of Silicon Valley, which is that you have to do things that scale. Right? Like, you could never go meet your early customers because how is that possibly scalable? But he gave us permission to do things that don’t scale. And it was so freeing for us.”

It was only the beginning of pushing the boundaries of possibility. With that focus on users, Airbnb scaled in a way few other companies ever have and revolutionized an industry along the way. The company went public in 2020 and $ABNB continues to boom on the NASDAQ even amidst uncertain times — the stock is up over 19% year-to-date as of this writing.

Reflecting on it all, Gebbia said, “Field of Dreams is the opposite of starting a company: If you build it, they don’t come.

“Entrepreneurship is an act. It’s a habit. It’s a muscle that you build over time that you can start at any point in life. It doesn’t matter how old you are. But if somebody’s sitting around, waiting for the big idea to come to them it’s not going to happen. You gotta go out into the world and you gotta start making stuff.”

For Gebbia, now 40 years of age, Airbnb laid the foundation for so much more. And for him, it has always been about more than the money.

Airbnb’s commitment to philanthropic work has accompanied its growth. Among countless outreach efforts, the brand paired with the Kevin Durant Charity Foundation to transform the basketball and tennis courts at Hayes Valley Playground in San Francisco.

Gebbia’s belief in making the impossible possible drives everything he does, and the launch of airbnb.org, which connects individuals with free housing in times of crisis, and his upcoming documentary about the refugee Olympic team are just two recent installments that recognize the power of limitless imagination.

All you need to do is build it and go find the right people to help you bring it to life.

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