Brian Chesky and Wayne Gretzky are not known to be relatives, business partners, or close personal associates. Their documented connection is more personal and influential: Airbnb co-founder Brian Chesky grew up playing hockey, wanted to become the next Wayne Gretzky as a young child, and later cited one of Gretzky’s best-known ideas about anticipating where the puck is going.
Chesky’s hockey background is more than a minor biographical detail. Hockey remained part of his life through college, where running a hockey club gave him early experience in leadership, marketing, community building, and organizing people. Those skills later became relevant to the creation of Airbnb.
What Is the Connection Between Brian Chesky and Wayne Gretzky?
The strongest verified connection is that Wayne Gretzky was a childhood sports hero for Brian Chesky.
In a 2022 appearance on The David Rubenstein Show, Chesky recalled that his father got him involved in hockey when he was five. He said they shared a dream that he would become Wayne Gretzky, although Chesky joked that by the age of six he had already realized that was unlikely to happen. Bloomberg lists Chesky’s appearance as an episode of The David Rubenstein Show, while a published transcript records his Gretzky comments.
That memory fits a broader account of Chesky’s childhood. A detailed Fast Company profile of Brian Chesky described hockey as one of the two major worlds of his youth, alongside art and design. Reporting based on interviews with his family described him skating from an early age and taking the sport seriously.
There is no reliable public evidence, however, showing that Gretzky personally coached, mentored, invested in, or worked with Chesky. The relationship supported by available evidence is one of childhood admiration and intellectual influence, not a documented personal partnership.
Brian Chesky Wanted to Be Wayne Gretzky Before He Wanted to Build Airbnb
Chesky was born in Niskayuna, New York, in August 1981. During his childhood in the 1980s, Gretzky was already the defining superstar of professional hockey.
Chesky has been unusually specific about that influence. During his Rubenstein interview, he remembered having Gretzky posters and wanting to emulate him. In another interview, he described his childhood as partly built around the expectation that being a successful athlete was an important path to recognition and belonging in the community where he grew up.
Gretzky was an understandable model for a young hockey player. The NHL’s profile of Wayne Gretzky records career totals of 894 goals, 1,963 assists and 2,857 points in 1,487 NHL regular-season games. He won four Stanley Cups with the Edmonton Oilers, nine Hart Trophies as league MVP and ten Art Ross Trophies as the NHL’s leading scorer.
Chesky never followed Gretzky into professional hockey, but the sport did not disappear from his life.
The Gretzky Idea That Stayed With Chesky
Gretzky’s influence also appears in how Chesky later discussed entrepreneurship.
In a questionnaire published by Greylock, an early Airbnb investor, Chesky recalled wearing two shirts at hockey camp as a child. One carried the famous Gretzky line about skating to where the puck is going rather than where it has been.
The NHL itself attributes essentially the same idea to Gretzky: “I skate to where the puck is going to be.”
For entrepreneurs, the metaphor is straightforward. Reacting only to today’s market can leave a company behind. The harder task is anticipating where customer behavior, technology, or an industry is moving and building for that future.
Chesky has used similar forward-looking thinking when discussing business decisions, but it would be an overstatement to claim that Gretzky’s quote directly caused a particular Airbnb strategy. What can be documented is that Chesky remembered the saying from his hockey years and continued referring to the underlying principle later in his career.
How Hockey Helped Shape Brian Chesky’s Entrepreneurial Career
The deeper Brian Chesky and Wayne Gretzky connection becomes clearer when Chesky’s college years are included.
Chesky attended the Rhode Island School of Design, or RISD, where he studied industrial design. RISD confirms that he graduated in 2004, later returned as its 2017 commencement speaker, and received an honorary degree.
More importantly for his business story, Chesky became heavily involved with the school’s hockey club.
In an interview published by Sequoia Capital, Chesky explained that he ran the ice hockey club while future Airbnb co-founder Joe Gebbia ran a basketball club. Chesky later viewed the experience of building interest in hockey among art-school students as an early lesson in running an organization.
The Sequoia Capital profile of Chesky’s early career describes the hockey club as an important testing ground for experiential marketing. Chesky and the other organizers had to convince students who were not necessarily sports fans to attend games, so they focused on spectacle, culture, and a sense of community rather than simply selling hockey itself.
Chesky has also said that managing the club required him to establish a vision, attract people, operate with limited resources, and persuade others to contribute. In a 2026 interview with Design Matters, he described the experience as a significant entrepreneurship lesson because the organization was largely self-directed.
That makes hockey an important link in Chesky’s professional biography. Gretzky was his childhood model within the sport, while managing hockey at RISD became one of his earliest practical lessons in building an organization.
Also Read: Lachlan Murdoch and Wayne Gretzky
From Hockey Ambitions to Airbnb
Chesky ultimately pursued design rather than professional sports.
He and Joe Gebbia became Airbnb’s first hosts in 2007, and Chesky went on to co-found the company with Gebbia and Nathan Blecharczyk. As of 2026, Chesky remains Airbnb’s co-founder and chief executive officer and serves as chairman of its board.
According to Airbnb’s official leadership information, the platform has grown into a worldwide marketplace involving millions of hosts. Airbnb reported in May 2026 that it had more than 5.5 million hosts and had recorded over 2.5 billion guest arrivals across its global network.
The path from wanting to become a hockey superstar to leading a travel technology company may look unusual, but Chesky’s own interviews show continuity between the two phases. Competition, community, anticipation, design, promotion and bringing people together repeatedly appear in his accounts of both hockey and entrepreneurship.
Who Is Wayne Gretzky?
Wayne Gretzky was born in Brantford, Ontario, on January 26, 1961. His official biography describes how he learned hockey on the backyard rink built by his father, Walter Gretzky, before advancing rapidly through youth and professional competition.
Gretzky eventually played 20 NHL seasons with the Edmonton Oilers, Los Angeles Kings, St. Louis Blues and New York Rangers. He retired in 1999.
His career was so exceptional that the Hockey Hall of Fame waived its normal waiting period and elected him immediately after retirement. The Hockey Hall of Fame’s Gretzky records archive also records the NHL’s decision to retire his No. 99 throughout the league.
After his playing career, Gretzky remained involved in hockey through executive, ownership and coaching roles, while also participating in business and charitable ventures. His official biography lists work with the Phoenix Coyotes, Canada’s Olympic hockey program, the Wayne Gretzky Foundation and commercial ventures associated with his name.
Did Wayne Gretzky Mentor Brian Chesky?
There is no credible public record showing that Wayne Gretzky served as Brian Chesky’s personal mentor.
Chesky’s comments describe Gretzky as someone he admired when he was young and whose hockey philosophy stayed with him. That is different from a direct mentor relationship involving meetings, advice, coaching or an ongoing professional association.
This distinction matters because online profiles can easily turn “inspired by” into “mentored by.” The evidence supports the first description, not the second.
Did Brian Chesky and Wayne Gretzky Ever Work Together?
No reliable source reviewed for this article establishes a direct professional collaboration between Chesky and Gretzky.
There is also no verified evidence that Gretzky was an Airbnb investor, Airbnb executive, board member or formal adviser. Likewise, Gretzky does not appear among Airbnb’s current directors or executive management listed in the company’s corporate governance materials.
It is always possible that two prominent people have met privately or attended the same event without that interaction becoming part of the public record. A private meeting should not, however, be presented as fact without evidence.
Is There an Airbnb and Wayne Gretzky Business Connection?
There is a small but potentially confusing overlap.
Airbnb has carried independently hosted travel experiences in Niagara wine country that include Wayne Gretzky Estates as one of several tasting stops. One Airbnb experience, for example, lists visits to Peller Estates, Trius Winery and Wayne Gretzky Estates.
That does not demonstrate a partnership between Brian Chesky and Wayne Gretzky. The experience is offered through Airbnb by a third-party tour host, while Wayne Gretzky Estates is part of Andrew Peller Limited’s brand portfolio.
It is therefore inaccurate to use such a listing as proof that the two men are business associates.
Brian Chesky and Wayne Gretzky Compared
| Fact | Brian Chesky | Wayne Gretzky |
|---|---|---|
| Born | August 29, 1981 | January 26, 1961 |
| Main field | Technology, travel and design | Professional ice hockey |
| Best known for | Co-founding and leading Airbnb | NHL career and scoring records |
| Hockey connection | Played from childhood and ran RISD’s hockey club | 20-season NHL career |
| Connection to the other | Wanted to emulate Gretzky as a child | No documented personal role in Chesky’s career |
| Current legacy | Airbnb co-founder and CEO | Hockey Hall of Famer and former NHL superstar |
Chesky’s official Airbnb profile confirms his current corporate role, while NHL and Hockey Hall of Fame records establish Gretzky’s career history and achievements.
What the Evidence Actually Shows
The Brian Chesky and Wayne Gretzky story is primarily about inspiration rather than a hidden business or family relationship.
Chesky has personally recalled wanting to become Gretzky when he was five years old. He continued playing hockey, eventually helped run the hockey program at RISD, and later remembered Gretzky’s forward-looking puck metaphor when discussing entrepreneurship.
There is no reliable public evidence that Gretzky became Chesky’s mentor, Airbnb partner or investor. The most accurate description is simple: Wayne Gretzky was an important childhood sporting influence on Brian Chesky, and hockey itself became an unexpectedly meaningful part of Chesky’s path toward entrepreneurship.
FAQ
Are Brian Chesky and Wayne Gretzky related?
No. There is no credible evidence that Brian Chesky and Wayne Gretzky are related by family. Chesky grew up in New York, while Gretzky was born and raised in Ontario, Canada.
Did Brian Chesky want to become Wayne Gretzky?
Yes, in the sense of childhood ambition. Chesky has said that when he was around five, he and his father shared the dream that he would become like Gretzky. He has also joked that he realized very quickly that professional hockey was unlikely to be his future.
Did Brian Chesky play hockey?
Yes. Hockey was a significant part of his childhood, and he later participated in and helped run the hockey club at the Rhode Island School of Design. Chesky has described running that organization as an early lesson in entrepreneurship and marketing.
Did Wayne Gretzky inspire Brian Chesky’s business philosophy?
There is evidence of influence, although it should not be exaggerated. Chesky has recalled wearing a hockey-camp shirt featuring Gretzky’s famous idea about skating toward where the puck is going, suggesting that the concept of anticipating the future stayed with him.
Have Brian Chesky and Wayne Gretzky worked together?
No documented collaboration was found in reliable public sources. Available evidence establishes Chesky’s admiration for Gretzky, but not a business partnership, mentorship or joint venture.
Does Wayne Gretzky have a connection to Airbnb?
Wayne Gretzky Estates appears as a destination in some independently hosted Airbnb travel experiences. That is a platform-level overlap and should not be interpreted as evidence of a direct relationship between Gretzky and Airbnb CEO Brian Chesky.
Also Read: Steve Cahillane and Wayne Gretzky
