Kevin Hart has always been funny, but his business misadventures prove he’s even funnier when it comes to investing in friends.
In a resurfaced 2022 clip from “The Late Late Show with James Corden,” the comedian and entrepreneur revealed that his generosity toward pals’ ideas once turned into what he jokingly described as an “endless pit of bankruptcy.”
Hart’s business empire has grown well beyond comedy stages and Hollywood films.
He founded HartBeat Productions, which merged with his Laugh Out Loud Network to manage comedy, film, and digital media projects. His tequila brand, Gran Coramino, has its own investment arm, the Coramino Fund, which has supported more than 100 small businesses. And his stand-up tours continue to pack arenas worldwide; his recent “Acting My Age” tour alone hit the U.S., India, Australia, and Saudi Arabia.
With Celebrity Net Worth estimating Hart’s fortune at around $400 million as of September 2025, it’s clear he knows how to turn laughs into serious cash.
But even a multi-millionaire comedian has to navigate the pitfalls of friendship and finance.
On Corden’s show, Hart admitted, “The worst business investment that I’m currently involved in is the business of investing in your friends. You never want your friends to feel like their ideas are not good ideas, but thus far, these ideas have been an endless pit of bankruptcy.”
He singled out one particularly ambitious venture: headphones that could open into speakers so anyone nearby could hear the music when asked, “What are you listening to?”
The product flopped — perhaps because commonly available open-back headphones already achieve the effect Hart’s friend was seeking — marking Hart’s most regrettable investment and offering him a humorous cautionary tale about mixing business with friendship.
Despite the occasional flop, Hart’s generosity extends far beyond ill-fated gadgets.
In 2022, he launched an AI Illumination Grant in partnership with the Fifteen Percent Pledge, Hartbeat Ventures, and A16z’s Cultural Leadership Fund, both of which support the community.
Through his Coramino Fund, he offers $10,000 grants to selected entrepreneurs and supports them with hands-on AI training and educational resources, helping them responsibly integrate emerging technologies into their operations.
Hart’s philanthropic streak is visible in smaller, more personal gestures as well. Three years ago, Hart made headlines after a trip to Sapphire 39, a well-known Manhattan gentlemen’s club, turned into an opportunity for him to help a fellow comic down on his luck.
He noticed Julio, a comedian performing on the street near the club for spare change. Struck by his talent and stage presence, the “Jumanji” actor gave him $500, roughly the price of one of his premium show tickets, turning a casual street performance into a moment of opportunity and recognition.
And in the past, he helped Tiffany Haddish when she was homeless early in her career. When he heard about her plight, he sent his “Night School” co-star $300 to secure motel lodging.
Such actions underscore that Hart’s heart remains as invested in people as his portfolio is in business.
In 2022, Kevin Hart’s mix of entrepreneurial ambition and friendship-driven generosity may have led to a few missteps, but they also reveal the comedian’s willingness to take risks and support others.
While investing in friends might once have felt like an “endless pit of bankruptcy,” Hart has been able to build businesses, nurture talent, and impact communities — sometimes with hilarious results. Just look at his “Prank Wars” show with his best friend, Nick Cannon.
