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

Hooters filed for bankruptcy in March 2025 after being operated by two very distinct operations

For years before that filing, the restaurant group had been operated by two different companies: one owned by private equity, and the other that includes the original founders.

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.

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.

PetSmart and Hilton are among 10 of the most famous leveraged buyouts in history

Some of the most famous leveraged buyout deals include Blackstone's 2007 acquisition of Hilton Hotels, in which Blackstone took the then-public company private and then returned it to the public markets in 2013. A British PE firm bought PetSmart for $9B in 2014—one of the most expensive leveraged buyouts since 2007.

Pets.com is one of the most emblematic dot-com companies

Pets.com—an e-commerce pet store webpage—is a prime example of dot-com companies burning through investments. Despite being a popular and well-known brand, the company struggled to generate enough revenue to become profitable. After raising approximately $82.5M in its February 2000 initial public offering, Pets.com filed for bankruptcy in November of that same year.

BlackRock acquired Merrill Lynch's asset management division, bringing in more than $500B in assets and pushing the firm's total assets under management above $1T in 2006.

Former Sears CEO and hedge fund manager Eddie Lampert was a reclusive billionaire who was once kidnapped from his home in Greenwich, Connecticut by criminals looking to get rich.

Unlike other franchises, the McDonald's Corporation owns the land and the buildings of individual stores, and franchise owners lease those assets—resulting in McDonald's often being called a real-estate company.

See a database of large companies owned by private equity firms

The Private Equity Stakeholder Project tracked more than 200 companies owned by private equity with more than 7,000 employees. Companies on the list include J. Crew, Jersey Mike's Subs, Barnes and Noble, Panera Bread, and Tropical Smoothie Cafe.

Tom Petty used bankruptcy to change the music industry after resolving a dispute over how a label was treating him as an artist and self-producing an album that racked up $500K in debt.

What is Chapter 11 bankruptcy?

While there are multiple types of bankruptcies, Chapter 11 is probably the one you've heard about the most. Technically speaking, Chapter 11 bankruptcy involves a reorganization of a business's assets and debts under court supervision. Companies such as Red Lobster, WeWork, and Party City have all filed for Chapter 11 bankruptcy in recent years. Learn more about it here.

As of 2024, Macy’s wanted to monetize its store closures through real estate deals

In a 2024 earnings call, Macy’s noted that while it’s remodeling and investing in some of its brick-and-mortar locations, it seeks to shutter other stores in lower-performing locations. It’s estimated that Macy's will close 150 locations through 2026.

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.

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.

In 2023 and the first half of 2024, Berkshire Hathaway bought back more than $12B of its own stock

In the second half of 2024, the company—and Buffett—decided to buy up shares of Domino’s Pizza, Pool, Sirius XM Holdings, and Liberty Media. They also decided to sell Capital One, Ulta Beauty, and Nu Holdings, among others. Learn why Buffett is buying and selling these stocks and what it could mean for the financial conglomerate.

Private equity firms often use leveraged buyouts to acquire new companies

In a leveraged buyout or "LBO," private equity funds finance acquisitions with debt secured by the target company's assets and cash flows. The PE firm aims to improve operations and leverage the company's profile to pay down debt, thereby increasing equity value.

Cheap debt and relatively minimal regulation have fueled private equity's expansion in recent years.

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

Former LuLaRoe vendors have accused the clothing multilevel marketing company of operating a pyramid scheme, resulting in more than 50 lawsuits and a $4.75M settlement.

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.

In 2025, Weight Watchers filed for Chapter 11 bankruptcy after reporting revenue and profit losses for multiple consecutive years, with its stock price losing about 99% of its value between 2018 and 2025.

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.

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.

Sophia Amoruso's company Nasty Gal was worth $100M at its peak

In 2006, Sophia Amoruso started an eBay shop that would later transform into the clothing company Nasty Gal. However, Amoruso’s rags-to-riches success with Nasty Gal didn’t last. After multiple rounds of layoffs and employee complaints, the company filed for bankruptcy in 2016.

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.

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.

Between 2016 and 2023, PE spent more than $200B buying British companies

Between the COVID-19 pandemic and the United Kingdom's official departure from the European Union, the UK's economy struggled to recover. This economic strife led to British companies receiving steadily lower valuations than American companies, prompting a huge increase in PE investment. However, interest rates began increasing in 2022, putting pressure on the numerous leveraged buyout deals that took place between 2020 and 2021.

In 2006, Macy's was worth $20B—but as of 2024, its market cap was just under $5B

Macy's went from roughly 800 to 500 stores within the same time period. Macy’s has spent the recent years since the pandemic closing swaths of stores.

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

In the fallout of the Great Recession of 2008, Barclays bought several assets from the failed investment bank Lehman Brothers in a fire sale and maintained the company's trademark, despite the bank's collapse. Tiger Lily Ventures attempted to launch a whiskey line parodying the name, but the product was rejected in court due to questions over Barclays' maintenance of the trademark.

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.

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.

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.

Although the national chain declared bankruptcy in 2010, a single Blockbuster Video store remains in Bend, Oregon.

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.

Some semi-liquid private credit funds saw a surge in investor redemptions in early 2026

This raised red flags about the state of the private credit market at large. However, experts have cautioned that the idea that private credit is on the verge of collapse is overstated.

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.

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.

Blackstone acquired a majority stake in Bumble's former parent company in 2019 ahead of the dating app's IPO

The New York City-based investment management company paid about $3B for its stake in female-focused dating app Bumble. The app's 2021 IPO that made Bumble Founder and CEO Whitney Wolfe Herd a billionaire at age 31 proved lucrative for Blackstone as well.

Private equity deals sometimes come with layoffs.

11,000 new US dollar stores opened between 2007 and 2017

Dollar store retailers experienced significant fiscal gains during the 2010s, which were then accelerated by the COVID-19 pandemic. But in recent years, dollar stores have been closing in large numbers and suffering financial hardship. Experts point to Walmart's strategy of decreasing prices to cater to inflation-fatigued customers, and point out that when Walmart does well financially, dollar stores typically suffer.

Contrary to popular belief, Netflix didn't kill Blockbuster, though it did intentionally position itself as an alternative to the movie-rental store.

North American department store retail groups report sales declined from 2018 to 2023

That's according to a recent report from Bain & Company that dives into consumer sentiment around department store shopping and explores a potential reset for the industry.

Listen to a 2026 interview where Bumble's CEO said its stock is down 96% since its IPO 'for no reason'

CEO and Founder Whitney Wolfe Herd said the company is still performing very well. She added that the business makes $1B per year and referred to it as profitable. She went on to say "who knows what people trade stock on?" and that she believes the stock market has written Bumble off as if it were debt

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.

Digital coupon platform Groupon IPO'd in 2011 at a $17.8B market cap, but as of 2024 was worth just $103M—a 99.4% decrease.

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.

The 2024 Synapse collapse took $90M of people’s life savings with it

In 2024, a banking middleman called Synapse declared bankruptcy. Unfortunately, it also locked roughly 100,000 Americans out of their own money, which prompted a class action lawsuit.

Rent the Runway recently lost over 90% of its value

The COVID-19 pandemic and increased competition post-2020 are just two factors plaguing the designer clothing rental company.

SoftBank lost billions of dollars on WeWork. Meanwhile, WeWork’s founder walked away a billionaire

In the years leading up to WeWork’s bankruptcy, the tech holding company SoftBank invested roughly $16B into the company.

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