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

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.

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.

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.

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.

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.

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.

Every year, nearly 500,000 bankruptcies are filed in the US.

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.

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.

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.

Chapter 7 and Chapter 11 filings can impact common stockholders

Publicly traded companies don’t file for bankruptcy out of nowhere—there are typically warning signs in a stock’s performance, quarterly earnings calls, and US Securities and Exchange Commission filings.

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.

The most common types of bankruptcy filings are Chapter 7, Chapter 11, and Chapter 13

However, there are actually six types in practice today. These less-common options can be lifelines for foreign businesses operating in the US, local governments, and farms and fisheries.

WeWork filed its first S-1 in 2019

When WeWork prepared to file for its initial public offering in 2019, its S-1 revealed its poor financial state to the public.

The Wing was a coworking space and private members club before it closed down

The Wing was supposed to be more than a woman’s answer to the popular WeWork coworking spaces. Founder Audrey Gelman envisioned The Wing as a private members club where women could feel empowered and dignified—if they had a few thousand dollars a year for a membership, of course. However, after racism scandals and widespread employee criticism, The Wing ceased operations in 2022.

Bumble went public with an IPO in 2021

That year, Bumble Founder Whitney Wolfe Herd became the youngest female CEO to ever take a company public. The company pivoted during the 2020 COVID-19 pandemic lockdowns, focusing its marketing strategy on promoting social-distanced dating and its video chat features.

Budget airline Spirit announced its shutdown on May 2, 2026

After filing for bankruptcy twice, there were a multitude of reasons for the airline's shutdown, including an increase in jet fuel prices due to the conflict in Iran in the first half of 2026.

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.

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.

A post-game interview with Sophia Amoruso directly after her 2016 Forbes cover

This article from 2016 is a time capsule of sorts. It includes an interview with the person who coined the term “girlboss,” Nasty Gal founder Sophia Amoruso, that took place just after she appeared on the cover of Forbes magazine. We now know that her company would go on to file for bankruptcy the next year.

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.

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.

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

Bankruptcy is a legal way to manage overwhelming debt, whether for individuals, corporations, or even local governments

Chapter 7 is for liquidating personal assets to clear debts, Chapter 13 allows a repayment plan for individuals, and Chapter 11 lets businesses reorganize to stay afloat.

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.

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.

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.

The first private equity fund was launched in 1960

At the time, the industry—and the public's understanding of it—was rather limited, and few private equity firms existed until the 1980s. The first leveraged buyout is thought to have taken place in 1955.

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

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.

Many of the 2010s girlboss-era founders experienced a public fall from grace in 2020

In the 2010s, dozens of female founders were celebrated on the covers of business magazines like Inc. for their recent startup success, from Emily Weiss’s Glossier makeup brand to Steph Korey’s Away luggage company. But many of these companies were also the subject of large takedown articles around the year 2020.

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.

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.

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.

Explore the differences between private equity, venture capital, and hedge funds

Private equity firms focus on buying and improving private companies with the intent to sell them for profit or take them public. Venture capital is technically a form of private equity in which investors focus on startups and generally don't seek majority control of the company. Hedge funds are pooled investments for sophisticated investors that pursue a wide range of often complex strategies.

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.

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.

The woman who coined the term ‘girlboss’ now has a VC firm called Trust Fund

In 2006, Amoruso founded the clothing company Nasty Gal, then later wrote a memoir called “#Girlboss” about her company’s meteoric rise. Later, she launched other ventures, including her “Business Class” business coaching series and the venture capital fund “Trust Fund.”

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.

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.

Bumble's origin story includes a Russian billionaire, a Tinder cofounder, and a private jet.

The collapse of Archegos Capital Management drew scrutiny to family offices

Archegos, which managed the assets of Bill Hwang, wasn’t subject to the same oversight as traditional investment firms when it collapsed.

Bumble's valuation peaked at roughly $13B around the time of its 2021 IPO

As of April 17, 2026, its market cap was roughly $550M. Experts attribute the decline to a multitude of factors, including slowing user growth and increased competition from Match Group-owned dating apps like Hinge.

The funeral home industry is increasingly consolidating via private equity firms

A growing share of the funeral home industry is being acquired by private equity-backed firms. A 2022 article states that about 20% of this $23B business is owned by funeral home chains, and private equity-backed firms own about a quarter of those.

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.

The history of bankruptcy in the US dates back to the signing of the Constitution

In 1787, this founding document gave Congress the right to establish nationwide bankruptcy laws. Legislators took advantage of that power in 1800 when they passed the Bankruptcy Act of 1800, the first comprehensive bankruptcy law at the federal level.

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.

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.

The legend of Pittsburgh’s fake Burger King

Years ago, a Burger King in Pittsburgh lost its franchise due to repeated customer complaints about food quality. However, the franchise-holders continued to operate the restaurant, switching to generic packaging but keeping the signage and uniforms. Customers eventually caught on and raised suspicions, leading to Burger King's corporate leaders' involvement. Learn more about the bizarre establishment and how it managed to continue operations for months.

Robinhood's mission of democratizing finance included its IPO

In 2021, investing app Robinhood went public—and decided to go about its IPO process differently. Unlike other companies, it opened up its IPO for the general public to purchase right away. A podcast episode explains what made Robinhood's IPO so unique prior to its launch date.