Claire's has filed for bankruptcy multiple times

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.

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.

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.

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).

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.

After making its US debut in 2015, Shein's sales surged during the pandemic—in 2023, the fast fashion company was valued at roughly $66B.

Chinese clothing retailer Shein accounts for about half of fast-fashion sales in America.

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.

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.

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

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.

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.

Listen to a podcast interview with an industry expert about why abstaining from fast fashion is so difficult for many Americans.

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.

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.

Fast fashion companies such as Temu and Shein often took advantage of the de minimis exemption, a US tariff loophole that ended in 2025.

Financial hardships forced functionality into every piece of Marie Curie's wardrobe

Curie's upbringing in a family that lost its fortune when participating in failed uprisings for Polish independence instilled frugality in her. Much of the clothing she purchased, including for special occasions like her wedding, was repurposed for lab use.

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.

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.

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.

Fast fashion brands sell cheap clothing by limiting how much they pay workers, using cheap synthetic material, and avoiding constraints on production levels and resulting environmental impacts.

Chanel faced major backlash in 2021 over its $825 Advent calendar

Chanel’s $825 Advent calendar drew millions of views on TikTok after shoppers unboxed items like stickers, string bracelets, and a standard dust bag—products many felt didn’t match the luxury price. The viral controversy made the calendar one of the year's most criticized holiday releases.

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.

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.

Despite many influencers having loyal followings, creator-led brands often fail when the hype from first-time buyers dies down and doesn't translate into repeat purchases.

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.

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.

Temu mainly sells off-brand items, while Amazon offers brand names

A personal finance expert breaks down the key similarities between Temu and Amazon in a quick video so consumers can decide which is the better choice for their shopping needs.

Temu was losing an average of $30 per order as of 2024

Some business experts have made the argument that Temu is more focused on rapidly gaining market share and growing its customer base than achieving profitability.

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.

The BNPL industry boomed amid a surge in online shopping during pandemic-era lockdowns

The buy now, pay later industry allows consumers to buy something immediately and pay in installments without the need for lengthy application and approval processes or high credit scores—and fintech companies Affirm, Klarna, and Afterpay are leading the charge by targeting young adults.

Explore a Sears historical timeline

Sears has existed for over 130 years, and is remembered for much more than its 2018 bankruptcy, from the Sears and Roebuck’s catalog to Discover Card and Allstate Insurance.

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.

An exploration of the life and death of US malls

American malls sought to recreate the cohesion of a downtown shopping center but with the indoor, quiet convenience of a rural or suburban setting. First developed in the 1950s, malls quickly took off and became the spine of American retail shopping. In the last two decades, online retail has forced many to close, leaving behind peculiar, vast abandoned spaces. Pick through the stark nostalgia with this fascinating photo essay.

Listen to a podcast episode that explains how the Chinese discount e-commerce retailer Temu became one of the most downloaded apps in the US.

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

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.

More than 80% of New York City's newsstands have closed in the past two decades, in part due to a series of price caps that hurt the stands' ability to evolve.

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.

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.

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.

BNPL has 19th-century roots, but the pandemic made it mainstream

The modern BNPL model didn't take off until the COVID-19 pandemic, when consumers were stuck at home and lockdowns forced them to shop online rather than in person. The number of US BNPL loans grew more than tenfold from 2019 (16.8 million) to 2021 (180 million), according to a Consumer Financial Protection Bureau report.

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 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 2024, the period between Thanksgiving and Cyber Monday saw 197 million shoppers

Some argue Black Friday has gone from one day of the year, to two days of the year, including Cyber Monday sales, to, more recently, an entire week. In recent years, companies have offered steep discounts for a week at a time rather than just one or two days.

Filing for Chapter 7 bankruptcy can be complex

Debtors must know whether their liabilities are secured or unsecured and what type of assets they have. They also need to know what a filing can and can’t help them with.

With the advent of charge cards, Estée Lauder fought to get her products in department stores to benefit from impulse purchases

Because Estée Lauder focused on personal relationships and demonstrations as one of her primary sales strategies, getting her product in front of enough people was an early struggle. Similarly, many customers wanted to buy her products, but didn't always have the cash on hand. One of her biggest accomplishments was earning a retail spot at Saks on 5th Ave in Manhattan, which paved the way for her brand to become a household name and gave customers more flexibility to make purchases on the spot.

Paper coupon suppliers and major newspaper insert distributors are in decline

Given the uptick in digital coupon adoption, sellers who offered coupon inserts or individual coupons for sale online have been closing up shop in recent years.

Sophia Amoruso coined the term 'girlboss' with her bestselling memoir

Sophia Amoruso turned a small eBay shop into Nasty Gal, a $250M fashion empire. Her success sparked the #Girlboss movement after her bestselling memoir, but behind the rise was a rapid fall. Leadership struggles and financial missteps led to bankruptcy in 2016.

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.