A reclusive billionaire ran Sears before its bankruptcy

Multiple business choices may have hindered Sears’ financial success

There’s no shortage of potential culprits for Sears’ death, from hedge fund manager Eddie Lampert, to Amazon, to the 2008 stock market crash.

Sears filed for Chapter 11 bankruptcy in 2018

Although the retailer may have failed financially speaking, some argue that longevity in itself is a success—the brand operated for over 130 years before that bankruptcy filing, after all.

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.

Scroll through a Sears historical timeline, starting in the year 1886

The Sears story starts with railroad worker Richard Sears purchasing a declined shipment of watches for a discounted price. An interactive historical timeline chronicles the history of Sears from then onwards.

Sears once tried to become a tech company

In 1984, Sears arguably created one of the first online retail services, called “Prodigy,” in 1984 alongside IBM and CBS. But it was more of a WeChat than an Amazon, offering a variety of other services to users a few years before the dot com era.

There’s a group of people hunting down the remaining Sears and Roebuck homes

A podcast episode dives into the history of Sears and Roebuck houses, including the people still searching for these real estate relics today. Many of them were destroyed or renovated beyond recognition, so they’re not easy to find or identify.

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.

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.

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.'

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.

In 1965, Warren Buffett took over Berkshire Hathaway, a failing textile company

After buying bulks of its stock, Buffett then flipped Berkshire Hathaway into the most successful and largest holding company in the world, which owns companies like Geico, Duracell, and Fruit of the Loom.

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.

Often dubbed the 'king of bank robbers,' George Leonidas Leslie stole an estimated $7M (equivalent to $200M today) and charged other criminals a $20K fee to evaluate their heist plans

Leslie studied architecture and used blueprints of safes and banks to execute meticulously planned bank heists across the Northeast between 1869 and 1878. Although Leslie was an infamous bank robber by night, he posed as a member of high society by day, providing critical intel on the institutions he'd rob and helping conceal his crimes. Months before his largest planned heist, where he planned to turn on his gang, Leslie's body mysteriously washed up along the Hudson River. His killer remains a mystery.

How to make a billion dollars, with Brad Jacobs

Brad Jacobs is a serial entrepreneur who has launched eight billion-dollar enterprises during his storied financial career. With companies focused in energy, waste, and more, Jacobs has stuck to a roll-up playbook of consolidating small players into one conglomerate within an industry, a common tactic of similar private equity firms. This podcast from Founders summarizes Jacobs' book detailing his approach.

Former US Senator Mitt Romney cofounded a revolutionary private equity firm

Mitt Romney cofounded Bain Capital—a private investment group that manages more than $215B—in the 1980s before becoming a politician. Bain Capital is credited with revolutionizing private equity by focusing on consolidating and streamlining business operations rather than relying on financial engineering to increase company profits.

Nvidia CEO Jensen Huang once saved Nvidia from bankruptcy with a multi-million dollar Hail Mary

Nvidia is now known as one of the top companies contributing to the AI boom, but back in the 1990s, it almost failed. One last-ditch effort conversation that CEO Jensen Huang had with an investor saved the company.

When Tesla died in 1943, the FBI seized his property for national security

Although Nikola Tesla had become increasingly eccentric in his later years, the US government wanted to ensure plans for a possible secret weapon didn’t fall into enemy hands during World War II.

Bed Bath and Beyond’s 20% off coupon had a cult following

The home goods store’s most fervent fans loved these coupons so much that some bought them in batches on eBay. The FBI even reportedly found one of these big blue coupons in famous mobster Whitey Bulger’s junk drawer. (Some users may experience a paywall.)

Some billionaires invest in extreme home upgrades for their estates

Car elevators, spas, movie theaters, bowling alleys, nightclubs and panic rooms are just some of the lavish upgrades the 1% builds in their homes.

Estée Lauder's son, Leonard Lauder, transformed Estée Lauder into a global powerhouse

Leonard Lauder became president of Estée Lauder Companies in 1972 and is credited with much of the brand's expansion. Under his leadership, the company launched new lines like Aramis and acquired luxury brands to bolster its position in the luxury beauty market.

John D. Rockefeller’s father had a nefarious past

William A. Rockefeller Sr. earned his money via various schemes that included pretending to be a doctor to sell “herbal medicines” and posing as a deaf person to peddle for money.

Born to a well-off family in South Africa, Elon Musk left for Canada in 1989 before heading to the US

Musk was bullied as a child in South Africa, and even recalled being punched in the face, per a recent Walter Isaacson biography on the entrepreneur.

A ‘Bored Ape’ NFT was once kidnapped

An art heist in the crypto world plunges listeners of the "Search Engine" podcast into another mystery about why so many celebrities suddenly started selling the public on NFTs in 2021.

The Walton family behind Walmart is the world’s richest family with $432B

The world’s 10 richest families, including the families behind Hermès and Mars, control hundreds of billions of dollars worth of the world’s wealth.

Meet a payday lender who tried to fight the industry

Phil Locke once ran more than 40 payday lending stores in Michigan before walking away from lending in 2012. Locke left because he said he felt guilty about being a predatory lender. He tried to become a consumer protection advocate and influence reform, but ended up returning to the industry. (Some users may experience an email wall.)

Jeff Bezos’ biological father and mother married as teenagers—and had Jeff a year later

His biological father, Ted Jorgensen, was a circus performer at the time. He later gave up custody of Jeff and became a bicycle repairman in Phoenix, Arizona. Ironically, the last time Jorgensen saw Jeff as a child was in a Walmart where Jorgensen worked. This video dives into the relationship between Jeff Bezos and his estranged biological father, who passed away in 2015.

Warren Buffett's former professor Benjamin Graham is known as the 'father of value investing,' a strategy in which investors seek to buy stocks trading below their intrinsic worth.

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.

The idea for the Federal Reserve was conceived in secret in 1910—with bankers donning duck hunt gear for disguise while traveling to a remote country club on Georgia's Jekyll Island

Watch this video that uses Lego bricks to explain how venture capital works.

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.

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.

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

In 2019, a laptop loaded with six of the worst malware in history and described as 'an exhibit of historical weaponry' sold for $1.3M.

In 2025, four executives from large tech companies were given positions in the US Army Reserves—including Palantir Chief Technology Officer Shyam Sankar, which reinforced Palantir's ties with the US military and its role as a leading defense partner.

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.

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

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

Art theft is the third-largest source of criminal revenues worldwide, thanks in part to the subjective nature of valuing a work of art.

Dozens of S&P 500 stocks, including Coca-Cola and Walmart—known as the dividend aristocrats—have increased dividends every year for 25 years

Sony set the standard for cylinder-shaped batteries when it repurposed manufacturing equipment used to make rolls of magnetic recording tape.

The animatronic shark from Steven Spielberg's 'Jaws,' the first modern blockbuster, was a complex underwater apparatus called 'Bruce.'

Before writing 'Walden,' transcendentalist Henry David Thoreau nearly burned down his hometown with a campfire that grew out of control.

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

Fast-casual restaurant Chili's is experiencing a resurgence, with its parent company recently reporting a nearly 32% increase in sales, thanks to passionate Gen Z fans on TikTok.

The tragic Pulitzer Prize-winning image 'The Vulture and the Little Girl' (1993) generated controversy, raised concerns about ethics in photography, and eventually led to the photographer's death.

Legendary architect Frank Lloyd Wright designed the SC Johnson headquarters in Wisconsin, aiming to make a cathedral-like workplace

Against his wishes, Albert Einstein's brain was removed before his cremation, and the pathologist responsible stored it for decades in mason jars within a beer cooler.

Roughly 43 million US borrowers owe roughly $1.7T in student debt, the second-largest source of consumer debt behind mortgages.

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