How a failed investment bank almost became the name of a whiskey line

Before Lehman Brothers filed for bankruptcy in 2008 with more than $600B in debt, the Federal Reserve tried to orchestrate a private deal to save the then-fourth-largest investment bank in the US.

A star investment banker was fired, launching a decade-long court fight

Star bankers are the core of an investment banking firm's business, so when Perella Weinberg let their restructuring guru Mike Kramer go in 2015, he sued, launching a ten-year legal fight.

Investment banking giant Lehman Brothers filed for bankruptcy in September 2008 when it had $619B in debt, making it the largest bankruptcy ever in the US

Nearly all of its 26,000 employees immediately lost their jobs. But in London, a few hundred remained tucked away, working for another decade to wind down the bank’s European business.

American Express briefly owned Lehman Brothers

In 1984, Shearson, a retail banking company and American Express subsidiary, bought the investment banking company Lehman Brothers—best known for its historic 2008 collapse—for $360M. The businesses were then called Shearson Lehman/American Express. American Express spun off Lehman Brothers with an IPO in 1994 that attracted nearly $3B in new capital.

Explaining the collapse of Silicon Valley Bank

In March 2023, Silicon Valley Bank—the nation's 16th largest bank at the time—collapsed after a rapid run on its deposits. Among other factors, the bank had placed more than half of its investments into long-term bonds, leaving it without the necessary cash on hand as its clients, largely start ups, panicked and withdrew their money at the same time. This visualization lays out the timeline and impact of the collapse.

In March 2008, Bear Stearns was the first major bank to collapse in the Great Recession—leading to panic across the entire global financial system.

Some companies like to make their IPO day antics unique.

An article details some of the wildest bell-ringing day stunts in recent history, from Clifford the Big Red Dog ringing the opening bell to one company's employees roasting marshmallows in a campfire on Wall Street as it went public.

The main bank serving Silicon Valley startups and venture capitalists collapsed in 2023

Silicon Valley Bank—the 16th largest bank in the US—served many tech startups in the area as well as many venture capitalists. The bank collapsed in 2023—in a single day, bankers took out $42B.

Red Lobster lost $11M on endless shrimp promotions—but its real estate holdings were what dragged it to bankruptcy

Golden Gate Capital, a PE firm, bought Red Lobster in 2014 for $2.1B. Golden Gate then sold Red Lobster's real estate, more than 500 storefronts, which generated $1.5B in revenue and helped finance the PE firm's acquisition of the company. Analysts say increased debt, high rent costs, and low equity put Red Lobster in an impossible position, leading to its 2024 bankruptcy filing—although the shrimp bill probably didn't help.

Comedian Nathan Fielder opened a store called 'Dumb Starbucks,' which was protected by US parody law.

The strange story behind President Jimmy Carter's brother's 'Billy Beer'

During Carter's 1976 presidential campaign, his brother, Billy Carter, became a sideshow attraction as a country bumpkin. The Louisville-based Falls City Brewing Company decided to capitalize on the attention and hired Carter has a brand ambassador to promote his own "Billy Beer." What followed was a strange, suspicious bit of guerilla marketing and hucksterism, all of it documented in this Mental Floss retrospective.

How one supplement company cost a short seller $1B

Pershing Square, a hedge fund founded and run by Bill Ackman, put short positions on Herbalife in 2012, because it believed the company was a pyramid scheme. Ackman's longtime rival and legendary investor Carl Icahn began buying Herbalife shares, causing the stock price to rise—ultimately hurting Pershing Square's short position.

A Portland dive bar helped drive Pabst Blue Ribbon's early 2000s comeback by selling cans for $1 apiece.

Venture capitalists were once bullish on DTC brands

While a physical store can only hold so many objects, online retailers without the limits of four walls that could sell their products direct-to-consumer could theoretically be great investments. But they didn’t always provide investors with expected returns.

Some argue that investment banking could be a health hazard

Back in 2012, a University of Southern California researcher published a decade-long study in which she observed investment bankers’ health. The results weren’t exactly stellar. Every individual the researcher observed developed a stress-related physical or emotional ailment within several years of working in investment banking.

Anheuser-Busch sold half of its real estate holdings to survive Prohibition

The Budweiser parent company also created and sold out more than 25 different nonalcoholic products during this time, including but not limited to infant formula, frozen eggs, and specialized coffees and teas.

Hear how the Piggly Wiggly grocery store founder attempted to squeeze short sellers by cornering the grocery store's stock

Founded in 1916 in Memphis, TN by Clarence Saunders, Piggly Wiggly was the first modern grocery store with aisles for customers to shop for themselves. In 1922, investors placed short positions, sensing that the stock may be overvalued after several Piggly Wiggly franchises in the Northeast went bankrupt. Saunders attempted to squeeze short sellers by taking out $10M and buying up nearly 99% of all available Piggly Wiggly stock. Ultimately, the fiasco ended with Piggly Wiggly's stock being permanently banned from the New York Stock Exchange and Saunders leaving Piggly Wiggly and filing for bankruptcy.

Explore Bessemer's anti-portfolio of missed opportunities

From Pinterest to Yelp, Bessemer Venture Partners—one of the most well-known VC firms—has invested in many successful companies over the years. But the firm has also kicked itself for passing on a few great opportunities, like Apple and Google. Check out the other companies in Bessemer's "anti-portfolio" here.

Larry Fink cofounded BlackRock with a $5M investment from Blackstone cofounder Stephen Schwarzman in 1988, before officially severing ties with Blackstone in 1994.

BlackRock played an integral role in the Federal Reserve's response to the Great Recession, managing about $30B of hard-to-sell Bear Stearns assets on behalf of the New York Fed.

Ray Dalio considers betting against the US debt load in 1982 among his biggest failures

In the early days of his hedge fund, Bridgewater Associates, Ray Dalio calculated that the US had accumulated more debt than it was possible to repay. He took short positions in the market that backfired when the Federal Reserve cut interest rates and avoided a global economic collapse. Dalio lost everything and even had to borrow $4K from his dad—but often describes this experience as one of the most pivotal moments in his career.

Watch the infamous live feud between Bill Ackman and Carl Icahn from 2013 in the fallout of a billion-dollar accusation that Herbalife was a pyramid scheme.

How ‘vulture’ hedge funds make money

Some hedge funds specialize in snapping up distressed assets, like failing newspaper chains, and further stripping down their operational expenses in a bid to make a profit from the initial capital outlay. Delve into how one secretive firm known for the practice operates—and what’s at stake for the broader economy.

Famed American investor Jesse Livermore made millions when the stock market crashed in 1929

Livermore made his first major short against rail company Union Pacific in 1906, coincidentally before an earthquake in San Francisco, which ultimately tanked share prices. During a financial panic the next year, JP Morgan reportedly asked Livermore to increase his long-term investments to restore hope and restabilize the market—which Livermore did. However, Livermore began betting against the market in 1929, sensing that stocks were too hot, and was one of the few people to benefit from the 1929 stock crash.

Commonly referred to as the 'bank bailout,' the Troubled Asset Relief Program disbursed $443B in an attempt to keep the financial system solvent.

Twain was a notoriously bad investor

After becoming a famous writer, Twain invested in railroad stocks, a magnetic telegraph, and a printing press that weighed four tons. Eventually, he founded his own publishing company, which ultimately led to his bankruptcy. “He is, in business,” one lawyer said, “just a big overgrown boy.”

Theranos and Pets.com are among some of the biggest startup failures ever

You might have heard of Theranos, Elizabeth Holmes’s one-time blood testing company that landed the founder in prison for more than a decade after she was charged with fraud. The rest of the startups on a list of five of the biggest startup failures ever might not be as famous as Theranos, but they were met with similarly disastrous fates.

The Failure Museum is a curated collection of over 1,000 items representing failed products and companies

Sean Jacobsohn, a tech investor and founder of the Failure Museum, uses items from failed businesses to explain the six primary forces behind their flops, from a Theranos mug to a Blockbuster membership card.

How venture capital firms came to be

The venture capital firm that kickstarted an industry.

IPOs that failed

Plenty of private companies fail once they try to go public. Failing can mean shares sell for less than their initial asking price on its IPO date, or it can look like a company pulling out of the IPO process at the last minute. Some companies with failed IPOs include Pets.com, Etsy, and Robinhood. Learn more about these companies and others here.

Just because a big name company is going public doesn’t guarantee a successful stock

A reporter dove into how highly anticipated IPOs can still be risky, and why retail investors should be wary of investing right away.

LVMH's roughly 75 brands are categorized into six distinct business groups

The groups are as follows: Wines and Spirits, Fashion and Leather Goods, Perfumes and Cosmetics, Watches and Jewelry, Selective Retailing, and Other Activities.

WeWork, once a unicorn, declared bankruptcy in 2023

This podcast episode chronicles the complete rise and fall of WeWork—from its founding in 2010 to its eventual 2023 bankruptcy.

Why did WeWork fail and why it's still around

Once valued at $47B, WeWork promised to revolutionize office space—but rapid expansion, financial red flags, and a pandemic-driven shift in work culture led to its 2023 bankruptcy. This overview looks at its rise and fall, and what’s next for the coworking giant.

'The Fund' exposed culture problems and scandals at Bridgewater Associates

In 2023, Rob Copeland—who covered Bridgewater Associates for The Wall Street Journal for 10 years before moving to The New York Times—wrote a book that drew from interviews, company documents, and meeting recordings. "The Fund" highlighted sexual harassment scandals, a company contract to hire strippers, and a toxic company culture. Dalio has criticized the author for being sensational and a gossip.

The dot-com stock bubble taught Howard Marks about markets

Annual investment letters from Howard Marks, the billionaire cofounder of top distressed debt shop Oaktree Capital Management, are required reading on Wall Street. The prolific writer and investor explains the distinction between the folly of trying to time the market and the necessity of paying attention to market cycles. The difference makes all the difference in returns.

Visualizing the financial troubles of FTX at the time of its bankruptcy

Just before Sam Bankman-Fried declared FTX bankrupt in November of 2022, he sought to raise funds quickly to try to save the cryptocurrency exchange. As part of that attempt, he sent around a glimpse of the exchange's current balance sheet, which showed the company had liabilities of $9 billion with only $900 million in liquid assets. Check out the visualization here.

The Beatles sued technology company Apple in 1978 to defend naming rights to their record label, Apple Corps.

London bankers created the first clearinghouse to process checks in 1770

Until that time, each banker was required to bring that day's checks to every other bank for settlement. Perhaps understandably, the first place bankers opted to gather to clear and settle checks was a tavern known as the Five Bells. The innovation gave rise to what would become clearinghouses, key institutions that facilitate payments.

A landmark hedge fund court case once reshaped high finance

Hedge fund traders tied to insider trading by probing prosecutors are relatively rare. When billionaire hedge fund legend Steve Cohen, founder of SAC Capital, pleaded guilty to trading on inside information, Wall Street trembled. The outcome of the case remains a cautionary tale for traders today.

The 2008 financial system unraveled in a wave of speculation

Michael Lewis—author of the bestselling "The Big Short"—explains how a wave of speculation (among other factors) drove the 2008 collapse, from lenders issuing risky mortgages to Wall Street turning them into fragile securities. He also highlights the few outsiders who recognized the bubble and bet against it before the crash.

These famous brands used to have different names

Did you know that Nike used to be called Blue Ribbon Sports? Or that Google was originally named BackRub? Getting a brand's name right is a tough job; there's an entire cottage industry of brand naming agencies to prove it. See which brands got it right the first time—and which ones might be better off with their current names—in this article.

Explore an alternative investments timeline

From what’s known as the first leveraged buyout, when JPMorgan acquired the Carnegie Steel Company, to the creation of the first-ever hedge fund, alternative investments have a long history.

Watch a breakdown of 'The Volcker Rule,' which stopped banks from being able to make trades with client money and is one of the most controversial financial regulations to date.

American International Group, one of the largest insurance companies in the world, received $182B from the federal government—the largest of any bailout in the wake of the Great Recession.

USDC's reserves were held at Silicon Valley Bank when the bank collapsed

One of the world's largest stablecoin's reserves were held at Silicon Valley Bank, which famously failed in March 2023. USDC briefly lost its peg to the US dollar for a time as a result, within investors pulling out billions of dollars.

Many investment bankers work on IPOs

When a company undertakes an IPO, investment banks often buy many of the organization’s shares directly from the company, in order to sell the shares on the stock market. The bank stands to profit after marking up the shares.

Venture capital explained through Lego bricks

Frisbee, Jet Ski, and Dumpster—explore a list of words you might not realize are trademarked

Many products that have become household names started out as first-of-a-kind items. As those products grew in popularity, the brand name became the default name for the product.

Southwest Airlines was profitable for nearly 5 decades, offering free whisky, cheap late-night tickets, and free-for-all seating allocation—despite how hard it is to make money running an airline.