When Brian Chesky first landed in Silicon Valley, he did not look like anyone’s idea of a startup founder. He was a former college hockey player and competitive bodybuilder, a guy who packed protein powder in his luggage and scheduled his days around the gym. In a tech scene dominated by rail-thin coders living on caffeine and takeout, Chesky’s physique felt less like an asset and more like a liability.

He has described those early years as a kind of culture clash. The unwritten dress code of the Valley favored hoodies, dark circles under the eyes, and a body shaped more by all-nighters than by deadlifts. Chesky, by contrast, arrived with broad shoulders and the habits of someone who had spent years under a barbell. That difference made him self-conscious.

On a recent livestream conversation, Chesky recalled deliberately hiding his body to avoid being dismissed as a “meathead.” He worried that if investors or peers saw his muscles, they would assume he was unserious or unintellectual. Long sleeves became a kind of armor, a way to blend into a culture that equated brilliance with a certain kind of physical neglect.

“People just didn’t really lift weights in 2007, 2008,” he said, reflecting on those early days. The Valley’s mythology centered on the mind, not the body. Founders were supposed to be monomaniacal about code and product, not macros and training splits. In that environment, Chesky’s bodybuilding background felt almost subversive.

Yet the same discipline that made him stand out physically would become central to how he built Airbnb. Long before fitness became fashionable in tech, Chesky was already thinking about startups the way a bodybuilder thinks about training: as a long, incremental grind where consistency matters more than any single heroic effort.

He often returns to a simple analogy. You do not get in shape from one workout. You get in shape by showing up, day after day, improving by a tiny fraction at a time. In his view, companies are built the same way. There is no single meeting, product launch, or stroke of genius that creates an “overnight success.” What looks sudden from the outside is, in reality, the visible tip of thousands of days of work.

Chesky has said that Silicon Valley’s so-called overnight successes actually take “thousands of days.” That framing mirrors the slow, methodical progress of strength training. You add a little weight to the bar, you refine your form, you recover, and you repeat. The results are invisible for long stretches, then suddenly obvious. Entrepreneurship, he argues, rewards the same stubborn willingness to keep going when there is no immediate payoff.

Over time, the culture around him changed. The Valley that once side-eyed weightlifters now obsesses over VO2 max scores, continuous glucose monitors, and longevity protocols. Fitness, which once seemed like a distraction from “serious” work, has become part of the founder identity. It is no longer unusual to see venture capitalists comparing deadlift numbers or CEOs posting their workout data.

Chesky has watched that shift with a mix of surprise and satisfaction. The habits that once made him feel out of place are now closer to the norm. He has said he is excited to see more people in tech embrace serious training and nutrition, not as vanity projects but as tools for sustaining high performance over decades.

Even as the culture has caught up to him, Chesky’s approach to fitness remains grounded in fundamentals. He does not outsource his workouts to algorithms. Instead, he trains with a human coach, a former Mr. Universe, who designs his routines and pushes him in the gym. For Chesky, that relationship underscores another lesson he has carried into business: the value of expert guidance and honest feedback from people who have already done the hard thing themselves.

Where he does lean into technology is on the nutrition side. Chesky has spoken about using artificial intelligence to interpret his bloodwork. After uploading his lab results to an AI system, he learned he was deficient in vitamin D and adjusted his supplements accordingly. It is a small example of how he blends old-school discipline with new tools, using data to fine-tune the inputs while still relying on human judgment and effort for the work itself.

The same blend of intensity and personal connection shows up in how he runs Airbnb. Chesky has become known for what he calls “founder mode,” a hands-on management style that cuts against the grain of traditional corporate hierarchies. Rather than limiting his direct reports to a small executive circle, he personally manages dozens of people across the company.

He has acknowledged that this approach is “a lot of work,” but he considers it necessary. In his view, a founder’s job is not just to set strategy from a distance but to build real relationships with the people executing that strategy. He has said that leaders should have direct connections with as many employees as possible, not just filtered updates through layers of management.

That philosophy echoes the same themes that run through his story as an athlete and entrepreneur: show up, do the work yourself, and do it consistently. Just as you cannot delegate your way to a stronger bench press, you cannot fully outsource the culture and direction of a company you founded. The reps matter, whether they are in the gym or in one-on-one meetings.

Chesky’s early discomfort in Silicon Valley reveals something deeper about the tech world’s evolution. The Valley once celebrated a narrow archetype of the founder: brilliant, disheveled, physically indifferent. That image is giving way to a broader understanding of performance that includes sleep, nutrition, and strength alongside code and capital.

For Chesky, the journey has come full circle. The traits that once made him feel like an outsider now look prescient. His bodybuilding past is no longer a quirk to be hidden under long sleeves, but a lens through which he explains how Airbnb survived its most difficult years and continues to grow. The same patience required to add five pounds to a lift over months, the same willingness to grind through plateaus, is what he believes separates enduring companies from the ones that burn out.

In retrospect, the bodybuilder in a land of insomniac coders was not out of place at all. He was simply early.