Multiple business choices may have hindered Sears’ financial success

A reclusive billionaire ran Sears before its bankruptcy

Former Sears CEO and hedge fund manager Eddie Lampert was once kidnapped from his home in Greenwich, Connecticut by criminals looking to get rich. Some argue that the incident colored Sears’ history.

Sears failed to evolve in a changing economy

At its peak, Sears was the largest retailer in the world, making elite objects accessible to the middle class. But in 2018, the company officially filed for bankruptcy due to massive debt and losses.

Inside one of the last Sears stores in the US

Sears was once one of the most successful businesses in the US. Today, there aren’t many Sears stores left in the nation, and the ones that are still around feel more like ghost towns than meccas of retail history.

Explore America’s top companies by revenue in 1994 versus 2023

America’s top companies by revenue have changed a lot in the past few decades. Sears, for instance, isn’t on the 2023 list, while Amazon isn’t in the 1994 edition.

Claire's has filed for bankruptcy multiple times

Between competition from online retailers such as Shein and Temu, and too many physical stores for today's retail climate, Claire's has had a difficult time modernizing.

The Sears catalog sold some weird products before it folded, including drugs

At various times in its existence, the Sears catalog sold everything from heroin to tombstones. But by the 2000s, the catalog was no longer in publication.

Macy’s announced a series of pandemic-era store closures in January 2021

Specifically, as mall foot traffic declined, Macy’s sought to grow elsewhere (as did many other retailers around the same time).

Bezos has frequently cited a 1999 article titled Amazon.bomb to illustrate how dire the early predictions about Amazon got

Over the years, Amazon founder Jeff Bezos often recalls how wrong the predictions in the 1999 Barron’s cover story were. Among other things, that article declared Amazon’s entire business model to be unsustainable and destined to fail, noting its lack of profit and dependence on a massive amount of capital to fund its growth.

A private equity firm led the leveraged buyout of Toys 'R' Us before the company's bankruptcy

After being acquired by two private equity firms and a real estate company for more than $6B in 2005, Toys 'R' Us filed for bankruptcy in 2017. Many point to the $400M a year the company had to pay to service its debt, as well as increased competition from online retailers like Amazon, for draining its profits and ultimately dragging it under.

See which companies folded and which survived the dot-com crash

Companies that primarily used the web as a platform for doing business were more vulnerable than companies that created technology. While hardware and software companies managed to make it to the other side, most e-commerce companies took a brutal beating and share prices plummeted.

In its famous catalog, Sears sold $600 DIY house kits from 1908 through the 1940s, resulting in an estimated 100,000 'Sears and Roebuck homes.'

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.

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.

Why private credit has faced challenges in recent years

The factors that some experts say are driving what could be private credit's most challenging era since the 2008 financial crisis include global economic uncertainty around trade and tariffs, investor fears about the amount of money being spent on artificial intelligence, and more.

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.

The story of Boeing's unraveling

Long lauded as one of the world's greatest aviation companies, Boeing has taken a nosedive in the last decade after major mass casualty crashes of its planes and high-profile scandals, which have led to numerous investigations, the temporary grounding of some of its planes, and a huge hit in its value. Listen to this first episode of a series telling the story of Boeing's fall.

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.

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.

Contrary to popular belief, Netflix didn't kill Blockbuster

Blockbuster was definitely the loser in its years-long battle with Netflix, but the conventional wisdom that the streaming giant killed the established video store chain is incorrect. Blockbuster’s large debt load—and an activist shareholder who didn’t fully appreciate the threat Netflix posed—led the chain to squander its advantages.

Tesla short sellers benefited from the company's poor performance in 2025

Tesla was widely considered the most-shorted stock until 2024, despite consistent short-seller losses. Between 2016 and 2020, short sellers reportedly lost more than $11B as Tesla's stock price continued climbing. However, long-held short positions began paying out in 2025 as Musk's foray into politics and his eventual feud with President Trump hurt Tesla's stock performance. In 2025, Tesla short sellers made more than $10B.

How Amazon operates a 'flywheel' business model, a self-reinforcing cycle that drives continuous growth

Starbucks operates more than 38,000 stores on six continents

The brand started with a single Seattle cafe and grew into an international sensation, thanks to former CEO Howard Schulz’s bold move toward “reigniting the emotional attachment with customers” rather than focusing on expansion.

The financial crisis in 2008 had a major impact on many 401(k) plans

Amid the 2008 financial crisis, stocks and bonds cratered as the broader market floundered due to the subprime mortgage crisis. Investors with so-called "target-date" funds—which shift allocations based on the maturation of a fund—shared in the slump, with some funds declining by 20% or more just a year or two away from maturation.

The 'Seinfeld' characters would likely be financially successful today

Even though Kramer probably doesn't have a 401(k) plan, he also probably struck gold as an investor with many side hustles.

Standard Oil's predatory business practices included temporarily operating at a loss to drive competitors out of business

Rockefeller's oil monopoly had a dark side, including cutting oil prices so low that Standard Oil was sometimes temporarily operating at a loss in order to drive competitors out of business.

Trader Joe's breaks every rule of modern retail

The successful grocer doesn't do e-commerce, delivery, or coupons. And yet Americans are still obsessed with Trader Joe's.

Discover the catastrophic consequences of a failure of the US electrical grid—something that is more likely than many Americans think.

SpaceX's S-1 or 'prospectus' revealed many previously unknown details about the company, including its unprofitability despite doing $18.7B in revenue in 2025, exactly how many voting shares Elon Musk will have in the company (roughly 85%), and more.

US consumers collectively owe more than $1T to credit card companies—almost as much as they owe in auto loans.

Up to a million Girl Scouts sell about 200 million cookie boxes every spring, generating $800 million, largely because refusing a child is frowned upon

A vending machine run with Anthropic's AI went out of business after it was convinced to give away items for free and sell a video game console.

When a Paris department store hesitated to sell Estée Lauder's perfume, she 'accidentally' broke a bottle, causing the smell to spread throughout the store and shoppers to start asking to buy the scent.

Hedge funds, the private investment firms that trade a wide swath of financial assets, make money by imposing steep fees on investors and from the fund's investment performance.

Netflix profits when you're not watching, and its movies are designed that way—read a detail-rich critical essay exposing lesser-known Netflix takes

The Beatles' US label rejected the band's first two singles, 'Please Please Me' and 'From Me to You,' with one executive calling the band 'dead in the water.'

A Yale student wrote a profound essay about the consulting industry's influence on elite college students that was published in a book of her writing after she died in a post-graduation car accident.

Mark Twain spent decades feuding with the US Postal Service, convinced its costs and regulations were bureaucratic overreach.

The Nasdaq's 'Magnificent 7' companies are responsible for roughly 40% of the Nasdaq 100 index's gains, while the remaining 93 companies account for the other 60%.

See a ranking of the best (and worst) Federal Reserve Chairs since 1914 out of the 16 men and women who have held the office since.

Domino's Pizza's 30-minute delivery guarantee was responsible for the chain's 1980s surge, but it was discontinued after the company was found liable for delivery driver accidents.

Firework or sparkler burns, even if they cover a relatively small area of skin, can significantly affect our range of motion.

Indefinite cloning of some endangered species may not sustain their longevity because cloning success rates decrease as genetic mutations accumulate.

Search a massive database of over 4 decades of clues from the TV quiz show 'Jeopardy!'

Volcanic activity may have triggered the Black Death by spewing gases that led to crop failures in Europe, thus forcing the import of grain ships with plague-infested fleas.

Many legends about George Washington, including his supposed wooden teeth and the story of cutting down the cherry tree, lack evidence.

Comedy legend Catherine O'Hara, star of 'Schitt's Creek' and 'Home Alone,' quit 'Saturday Night Live' after just one week to return to her old job.

Explore chaos in this simulation of two double pendulums, where small differences in the release angles produce wildly different outcomes.

To reduce wrinkles in clothing, research recommends gentle wash cycles with more water and tumble drying with smaller loads and longer times.

Watch a 1934 short film starring jazz legend Cab Calloway, a major figure in the Harlem Renaissance's music scene