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

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.

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.

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.”

Sophia Amoruso reflected on the girlboss movement 10 years later

It has been more than a decade since 2014, the year Sophia Amoruso published her book "#Girlboss," which became a New York Times bestseller. Since then, Amoruso has more or less journeyed through the seven circles of the corporate underworld, and the "girlboss" has been declared dead. This podcast episode lets listeners hear her thoughts on the legacy of the girlboss phenomenon 10 years after she started it.

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.

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.

The Girlboss TV show is generally regarded as a failure

Sophia Amoruso’s memoir, “#Girlboss,” spawned more than just a cultural movement—it also inspired an ill-fated television show that is remembered as one of Netflix’s first major failures.

Girlboss founder Sophia Amoruso doesn’t use the word 'girlboss' anymore

An article dives into not only the origin of the term “girlboss,” but also the quotes from the woman who coined the term about her thoughts on the word and the movement around it. In the piece, she explains that she doesn’t identify with or claim the word "girlboss."

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.

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.

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.

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.

More than 650 companies went public in the US in 1996

As the dot-com bubble reached its peak, most dot-com companies went public with little proof of being profitable and were often overvalued. In 1999, the Nasdaq's price-to-earnings ratio (a tool used to determine a stock's value that divides its price by earnings) hit 90.2, signaling that many companies were operating at a net loss. Startups promised investors that more time and money would help scale their businesses and become profitable.

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.

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

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.

Many female-founded companies were branded with the color 'millennial pink.'

Theranos and Pets.com are among some of the biggest startup failures ever

You might have heard of Theranos, Elizabeth Holmes’s one-time blood testing company that landed the founder in prison for more than a decade after she was charged with fraud. The rest of the startups on a list of five of the biggest startup failures ever might not be as famous as Theranos, but they were met with similarly disastrous fates.

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.

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.

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.

The 'big bang' of the dot-com era: Netscape's stock price doubled on the day of its initial public offering

The company behind the browser that revolutionized search went public on August 9, 1995. Just before the IPO, the company increased its initial opening price from $14 to $28. On the day the company went public, shares traded as high as $71 before closing at $58.25. The company's market capitalization exceeded $2B. The eye-popping IPO is largely considered the beginning of the dot-com bubble.

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.

The dot-com bubble burst in 2000 when the Nasdaq dropped more than 76% in roughly 2 years

Between 1995 and 2000, the Nasdaq Composite index jumped from roughly 1,000 to 5,000 amid excitement over new internet companies. As venture capitalists dumped money into startups, those same companies struggled to turn a profit, leading to a bubble. The Nasdaq wouldn't reach its former high until 2015.

Around 60% of female billionaires in the US are considered self-made—meaning at least some of their wealth comes from a business venture launched on their own.

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.

Yahoo acquired Paul Graham's former startup Viaweb in 1998

Viaweb was the web app tech startup that Paul Graham, Robert Morris, and Trevor Blackwell cofounded before they started Y Combinator. The company sold for $49M and Viaweb was rebranded as the Yahoo Store.

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

What happens when a hedge fund grows too big, too fast?

Dmitry Balyasny, who heads what has become one of the top US hedge fund firms, got a crash course in finance as a teenager, when he started trading stocks—and started losing money. Balyasny went on to lose a whole lot more money. But, this time, it wasn’t his to lose. To find out more about his firm’s remarkable comeback, read this article.

23andMe declared bankruptcy in March 2025

The consumer genetic testing company, which offered detailed genetic profiles from users' saliva samples, suffered financially after they suffered a major data breach affecting almost 7 million customers in 2023. Its flagship product was a one-time genetic analysis which also made retention of users challenging.

The Marc Jacobs grunge fashion collection

After Nirvana's breakthrough, the grunge aesthetic became a marketable commodity. Fashion designer Marc Jacobs created a collection for Perry Ellis that featured grunge fashion, incorporating thrift store clothing typically worn by grunge bands onto the runway, accompanied by the music of Nirvana and Sonic Youth. Jacobs sent samples of the collection to Kurt Cobain and Courtney Love, but the couple burned them. "We were punkers," Love said in 2010, "we didn't like that kind of thing."

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.

The Black Lives Matter movement coincided with the fall of the girlboss

It’s no coincidence that the white women who were seen as the faces of the girlboss movement (founders such as Audrey Gelman of The Wing and Christene Barberich of Refinery29, for instance) stepped away from their companies around the same time that America stepped into its era of racial reckoning with Black Lives Matter.

Tiffany & Co. was among LVMH's most expensive—and complex—acquisitions

Three years after LVMH acquired Tiffany in 2021 for $15.8B, the jeweler's profits doubled to over $1B per year.

How Martha Stewart became the first self-made billionaire woman

Through her cooking shows, cookware, and media empire, Martha Stewart ascended to billionaire status in 1999, becoming America's first woman to achieve that number on her own. Despite a conviction in 2004 and time spent in prison, Stewart rebounded and continues to develop product lines and media, with an estimated net worth of $200M. Read more about her story here.

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.

Famous scammer Anna Delvey lied about having a $67M trust fund

Delvey conned New York City’s elite with her lies, saying that she was a German heiress and defrauding the city’s banks, restaurants, and more out of more than $275K in just 10 months. Her story was even turned into a Netflix series while she was in prison.

In 1994, Amazon was founded as an online bookseller

Books were just the start, as founder Jeff Bezos' ultimate goal was to create an "everything store," using the internet to transcend the physical limitations of brick-and-mortar retail. The Seattle-based Amazon gradually added CDs and consumer electronics, becoming a dominant e-commerce player in the late 1990s, and one of the few dot-com companies to make it through the bust.

The dot-com boom sent tech stocks soaring before a historic collapse

A look at the dot-com bubble, when investors poured money into unproven internet startups, driving the Nasdaq to dizzying heights before it crashed by more than 80% after 2000, showing how new technologies can detach markets from reality.

Hermes once usurped LVMH as the world's most valuable luxury company in April 2025

At the time, Hermes's market capitalization surpassed LVMH's after a tough earnings report for LVMH in Q1 2025. The news came roughly fifteen years after LVMH tried to quietly build a stake in Hermes.

GameStop stock began a meteoric rise in January 2021, rallying from a low of $2.57 to as high as $438 when Keith Gill helped mobilize retail investors to drive prices higher

Keith Gill was a financial advisor who posted on social media under usernames including "Roaring Kitty." Backing from Chewy founder Ryan Cohen, who became GameStop's CEO, took things up a notch.

PayPal was started in 1998 by Peter Thiel

By the year 2002, PayPal went public for the first time—but that was far from the end of its business story. eBay later bought PayPal, then eventually spun it off. PayPal IPO'd for a second time in 2015.

Caroline Calloway: The influencer who botched two six-figure book deals

The daughter of a real estate mogul, Caroline Calloway was an Instagram influencer who leveraged her "Cambridge captions"—young adult novel-esque descriptions of college parties—into a six-figure book deal in 2014. After having failed to produce...

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.

'The Million Dollar Homepage' is a snapshot of a dead internet

In 2005, 21-year-old Alex Tew set out to make $1M by selling $1 pixels on his website, effectively creating a standalone internet billboard. The gambit worked, and because the advertisements were one-time payments, the site looks the same as it did in 2005, despite many of the advertised sites going defunct since.

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.

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.

In the 1870s, a woman from Boston ran a Ponzi scheme disguised as a bank by women, for women that promised 8% interest.

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.

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