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Wednesday, August 13, 2025

5 Celebrities Who Remorse the Enterprise They Invested In


Celebrities are sometimes seen as trendsetters—however in terms of enterprise investments, even their fame can’t assure success. Many stars have poured thousands and thousands into ventures that later fell aside, leaving them with extra remorse than returns. Studying about their errors helps us all perceive the dangers behind flashy offers. Whether or not it was actual property, tech, or eating places, these celebrities realized laborious classes the costly means. Listed here are 5 superstar regrets enterprise funding tales—each a cautionary story for anybody with massive ambitions and deep pockets.

1. Kim Basinger and the Failed City Buy

5 Celebrities Who Remorse the Enterprise They Invested In

Picture Supply: YouTube/Web page Six

Kim Basinger famously bought the whole city of Braselton, Georgia, for roughly $20 million in 1988, hoping to rework it right into a movie-themed vacationer vacation spot. Sadly, the plan collapsed, and she or he later bought a lot of the city for simply $1 million—dropping almost $19 million within the course of. Critics say the undertaking was overly formidable and poorly deliberate, missing a viable enterprise mannequin. Basinger finally filed for chapter in 1993 after the flop turned too heavy to maintain. This is among the most putting examples of a star regretting a enterprise funding gone terribly fallacious.

2. Jay‑Z’s $50 Million Lodge Ventures

celebrity regrets business investment - Jay Z - Peacock

Picture Supply: YouTube/Peacock

Earlier than reaching billionaire standing, Jay‑Z invested over $50 million in two actual property developments in New York’s Chelsea and Meatpacking Districts by J Accommodations. Sadly, the initiatives died amid the 2008 monetary disaster, leaving Jay‑Z embroiled in authorized disputes along with his lenders. He reportedly misplaced most of his funding and was compelled to exit the offers at a major loss. Regardless of his entrepreneurial instincts, the timing and financing of the undertaking proved disastrous. It stays a high-profile lesson in actual property dangers for even essentially the most formidable superstar traders.

3. Selena Gomez’s Postcard App That Didn’t Take Off

celebrity regrets business investment - Selena Gomez - CBS Sunday Morning

Picture Supply: YouTube/CBS Sunday Morning

In 2011, Selena Gomez invested $750,000 in Postcard on the Run, an app pitched on Shark Tank that permit customers ship printable postcards. Regardless of preliminary buzz, the app by no means gained traction and was discontinued by 2015. Gomez reportedly misplaced her whole funding when the enterprise did not scale. Whereas she’s since rebounded with profitable model partnerships, this stays certainly one of her lesser-known regrets in enterprise. For a lot of followers, it’s a reminder that even star energy can’t assure success in tech startups.

4. Justin Timberlake’s MySpace Acquisition Gone Bitter

celebrity regrets business investment - Justin Timberlake - The Tonight Show Starring Jimmy Fallon

Picture Supply: YouTube/The Tonight Present Starring Jimmy Fallon

In 2011, Justin Timberlake and a companion agency paid $35 million to accumulate MySpace, as soon as the main social community. Years later, MySpace’s lively person rely had dwindled to just about zero, and Timberlake reportedly bought his stake for simply $1 in 2015. The platform had turn out to be irrelevant within the face of Fb and Instagram dominance. The deal turned an embarrassing footnote in his in any other case savvy enterprise profession. It’s turn out to be one of the vital mentioned instances of superstar regrets about enterprise funding in tech.

5. Robert de Niro’s Pricey Artwork Rip-off

celebrity regrets business investment - Robert de Niro - The Tonight Show Starring Jimmy Fallon

Picture Supply: YouTube/The Tonight Present Starring Jimmy Fallon

Legendary actor Robert de Niro invested roughly $600,000 with artwork seller Tod Michael Volpe, trusting him to handle a set. As a substitute, Volpe bought items and even a shared Aston Martin with out informing de Niro or paying him. The rip-off value him each cash and belief within the artwork world. Volpe was finally convicted for defrauding de Niro and others out of thousands and thousands. 

A Smarter Method to Make investments: What Celebrities Want They’d Recognized

If stars might return, most would vet their offers extra completely, diversify their portfolios, and keep away from placing all their eggs in a single basket. Having a trusted monetary advisor, structuring investments by protections like LLCs, and conducting third-party audits can forestall many pitfalls. Scaling progressively moderately than sinking thousands and thousands in a single go can be a safer route. And by no means underestimate the significance of authorized counsel—contracts matter. Whether or not you’re investing thousands and thousands or saving pennies, these superstar regrets enterprise funding tales underscore the worth of warning.

Have you ever ever backed a enterprise that didn’t pan out—or heard an analogous superstar flop story? Share your expertise or what you realized within the feedback under!

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The submit 5 Celebrities Who Remorse the Enterprise They Invested In appeared first on Plunged in Debt.

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