David Gebbia knows there are easier places to make a bet than Los Angeles right now. He doesn’t seem particularly interested in easy. Alongside his twin brother and co-founder, Richard, David is planting a flag on Sunset Boulevard, taking over a penthouse space with a sprawling balcony, with plans to turn it into a cultural hub. “We’re staying put and trying to really help the city out,” Richard says.
For David, Gebbia Media is less a departure from the family business than its latest evolution: the same instincts he learned on Wall Street, now applied to music, media and culture. Learn the business from the inside, bet on relationships and keep building.
From The Ground Up
David Gebbia grew up inside a Wall Street dynasty, but nobody was handing him a corner office. His twin brother, Richard, got the same treatment. Their father came to the United States from Sicily at 9 years old without speaking English. He began working as a teenager, eventually found his way into finance and built his career through the kind of schedule his sons still talk about with a mixture of admiration and disbelief. “He worked 14-, 15-hour days back then,” David says. Richard quickly corrects him: “Still does.”
As teenagers, the brothers sat quietly through business dinners, listening and learning. “We didn’t say much,” David says, “but I promise you we learned more at those meetings, and at a faster pace than any college will ever give you.”
When David officially entered the family business, he started at the bottom. He remembers the exchange floor as a kind of “baptism by fire.” Richard’s experience was much the same. “We rolled our sleeves up. We learned the business from the ground up,” he says. “The traders didn’t want to give me a desk. So I actually had a fax machine as my desk.”
Football Pads And MTV
David came out of that upbringing with Wall Street in his blood and rock and roll in his heart. Richard took a different route through SEC football before joining him in finance.
Richard played at Ole Miss and spent time around the Jets before entering the family business. “You learn team,” he says. “Team is number one. Nothing happens without the team.” For him, the transition to Wall Street felt surprisingly natural. “A lot of athletes, they get lost because they lose that team. I rolled right into another team.”
David’s obsession was different. Another world was constantly flickering in the background—MTV. Later, after moving to Los Angeles and spending time around Sunset Boulevard, that interest turned into something more serious. “I think both of us got addicted to rock,” David says.
They met and partied with musicians, and David saw how hard successful artists actually worked. The brothers eventually began looking at music catalogs as investments, then had an opportunity to buy a label from friends exiting the business.
“We had that mindset that we could always do things better,” David says.
Too Rich To Work, Too Restless Not To
That instinct had already been tested once before. After the family sold Kennedy Cabot, David and Richard were around 30, flush with money and bound by a five-year non-compete.
David recalls the brothers prowling Rodeo Drive like the characters from A Night at the Roxbury, money in their pockets and no clear idea what they were going to do next. “I think what we both realized is that we will never retire,” David says.
Once they were able to build again, many former employees returned. Richard sees that as proof that what they had built went beyond the balance sheet. “We really built not only a firm, but we also built a family,” he says. The companies changed, but the relationships carried forward.
Rock Stars, Athletes And Money
David sees music, finance and influence as increasingly interconnected. “People follow people,” he says. Richard has a more colorful way of describing the same overlap: “Every athlete wants to be a rock star, and every rock star wants to be an athlete.”
The point is more than a punchline. Athletes and musicians both need financial guidance, and both command loyal audiences. For David, that makes music a natural extension of a business already built around trust, relationships and money.
On the music side, he is particularly bullish about being hands-on. The label isn’t just uploading tracks and hoping an algorithm does the rest. David talks about helping artists with everything from image to production and distribution. “You need people that actually have the expertise,” he says. It is a new industry, but the approach is familiar.
The Human Bet
For all the talk of media, culture and technology, David’s larger wager is oddly old-fashioned—people still want to talk to people. He sees it among clients who receive stock grants and suddenly need real guidance. “As much as there’s AI, people do like talking to somebody still,” he says.
Richard reinforces the point from the service side. “Our company prides itself on the fact that, with our 300-plus employees, we pick up the phone,” he says. “You’re not talking to a machine.”
The brothers aren’t rejecting AI, but neither believes software makes human judgment obsolete. Richard puts it simply: “We’re also betting that the world still needs the human touch.”
From Sicily To Sunset
David can already see the next generation entering the picture. His daughter Destiny is Creative Director at Big Machine Rock (BMR) and models and acts, while his daughter Mysteri is a music artist preparing to release new music. Richard’s son, Tristan, and other children, as well as the twins’ nephews, are beginning to learn the business.
Three generations ago, their family’s American story began with a Sicilian immigrant finding his way into Wall Street. David learned the business in mailrooms, at business dinners and on exchange floors before carrying those lessons somewhere different. Now the classroom is Sunset Boulevard, populated by musicians, athletes and dealmakers. The industries keep changing, but the family playbook doesn’t.