As the saying goes, “Every master was once a disaster.” A peek into the entrepreneurial journey of Donald Trump, a real estate tycoon and former president, underscores this adage. He’s had his fair share of towering successes, but buckle up because we’re about to embark on a rollercoaster ride through Trump’s most epic business flops.
Here are the triumphs, trials, and truckloads of Trump’s trials and tribulations, which highlight a critical entrepreneurial lesson: failure is just success in progress.
In 1988, Trump acquired Eastern Air Shuttle, but despite big promises, Trump Airlines never turned a profit. The high debts forced him to default on his loans, and the airline was eventually sold.
Trump’s foray into the alcohol industry tanked. Launched in 2006, Trump promised it would beat “the finest wines and champagnes.” By 2011, production had ceased due to lackluster sales.
Trump’s penchant for casinos resulted in multiple bankruptcies. His Atlantic City ventures—Trump Plaza, Trump Castle, and Trump Taj Mahal—all filed for bankruptcy numerous times.
Promising success in real estate, this venture was mired in lawsuits and accusations of fraud. It was forced to close in 2010, and Trump had to pay a $25 million settlement in 2016.
Launched in 2007, these high-priced steaks were dropped by their exclusive retailer, The Sharper Image, after a couple of months due to poor sales.
This lifestyle magazine folded in 2009, just two years after its launch, due to a lack of interest and revenue.
Trump: The Game
This board game was bombed twice, first in 1989 and then in 2005. As Trump quipped, “I thought it would sell… Many asked, ‘Why would I waste my time playing a game?’
Launched in 2006, this venture crashed within 18 months amidst the financial crisis.
Trump’s bottled water brand evaporated with little fanfare.
This online travel search engine lasted just a year after its launch in 2006 before disappearing.
Trump’s multi-level marketing company, selling health products, folded in 2012 after less than three years in operation.
Trump Tower Tampa
This planned residential tower never materialized. Pre-sold units’ deposits were primarily lost, leading to lawsuits.
Trump’s Communication Company
Donald Trump Media’s telecom venture in 2007 was declared lost without a trace.
Trump New Media
In 2011, Trump’s Internet startup also went quietly. With no more than a landing page, it was an epic fail in the digital world.
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