Donald Trump Said, 'In The End, You're Measured Not By How Much You Undertake But By What You Finally Accomplish' — A Look At His Many Failed Businesses Over The Years

Before entering the political arena, former President Donald Trump was best known for his splashy real estate ventures and for hosting the popular reality TV show "The Apprentice." 

In 1987, he proclaimed in New York Magazine, "In the end, you're measured not by how much you undertake but by what you finally accomplish." 

Now, Trump is embroiled in a civil fraud trial that could potentially bar him from doing business in New York. As he faces a legal reckoning, his credibility is under scrutiny. While he has had notable successes, his business history is also marred by significant setbacks. With his reputation on the line, examining Trump's failed business ventures has never been more relevant.

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Trump Mortgage: A Failed Foray Into Home Loans

In 2006, Trump announced the launch of Trump Mortgage, a company aimed at becoming the No. 1 home mortgage lender in the U.S. However, the timing wasn't on Trump's side. The housing market crashed in 2007, and his mortgage company was shuttered after 18 months of operation. Time reported that Trump had earlier asked on CNBC, "Who knows more about financing than me?"

Trump Steaks: A Taste Of Luxury That Didn't Last

Trump ventured into the meat industry with Trump Steaks in 2007, offering what he described as "the world's greatest steaks." Sold exclusively through Sharper Image and QVC, Trump Steaks didn't last long and was discontinued because of lackluster sales. Trump touted his product by saying in the commercial, "One bite and you'll know exactly what I'm talking about. And believe me: I understand steaks. They're my favorite food."

Trump Vodka: A Premium Drink That Didn't Measure Up

Trump also tried to tap into the luxury vodka market in 2006. Despite initial enthusiasm, the vodka brand ceased production around 2011. Trump Vodka fell short of the required thresholds to maintain its trademark, leading to its discontinuation.

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Trump Casinos: A Gamble That Didn't Pay Off

Trump's involvement in the casino industry, particularly in Atlantic City, New Jersey, also turned out to be less than profitable. Notable ventures like Trump Plaza, Trump Marina and Trump Taj Mahal faced financial difficulties, underwent multiple bankruptcies and closed their doors.

Trump: The Game — Monopoly, But Not Quite

The entrepreneur also dabbled in board games, releasing "Trump: the Game" in 1989. Despite being revamped in 2005 following the success of "The Apprentice," the game failed to become a household name. 

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Trump Airlines: A Sky-High Failure

In 1988, Trump acquired Eastern Air Lines Shuttle for $245 million, rebranding it as Trump Airlines. Despite the luxurious upgrades, like gold bathroom fixtures, the business did not take off as expected. Unable to cover the $1 million monthly interest on his loan, Trump eventually defaulted and lost ownership to his creditors. Yet, Trump remained optimistic, stating in a 2011 interview with TheStreet, "The airline business is a tough business, [but] I did great with it."

Trump University: An Educational Embarrassment

Trump University stands as a prominent example of legal entanglement and controversy. Established in 2005, the institution promised to offer courses in real estate and wealth-building but was not an accredited university or college. Multiple lawsuits accused the organization of defrauding students through misleading marketing tactics. Trump agreed to pay $25 million in settlements in 2016, thereby closing another contentious chapter in his business history.

Where Trump Went Wrong, You Could Go Right

It's worth noting that while Trump finds himself in hot water, being a legitimate business owner and investing in startups still offers a legitimate and potentially successful avenue for entrepreneurs who play by the rules. Risk is an inherent part of entrepreneurship — but so is due diligence, integrity and a solid business plan. One might say that rather than taking a page from Trump's playbook, aspiring entrepreneurs could consider this a how-not-to-do-it guide, sprinkled with cautionary tales that could make even the most optimistic business guru wince. In a world where success isn't guaranteed, it's better to build something you'd be proud to stand by rather than defend in court. 

If you're looking to invest in startups without high drama and questionable tactics, platforms like StartEngine offer a more transparent and straightforward approach. StartEngine is a crowdfunding platform that connects investors with promising startups in need of capital.  

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