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

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.

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.

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.

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

Many of the female-founded companies of the “girlboss era” in the mid-2010s had one thing in common: A certain light shade of pink was core to their brand book. The color—deemed “millennial pink”—was found on the packaging of makeup company Glossier, the walls and logos of coworking space The Wing, and the suitcases of luggage company Away.

The values espoused in 'Lean In,' a book by a female Facebook exec, was part of the girlboss movement's doctrine

Sheryl Sandberg, a top executive at Facebook, published "Lean In," her career-advice book for women, in 2013. The book would go on to spend more than a year on The New York Times Best Sellers list and contribute to a cultural movement.

Nonprofit VC funds invest in startups, but have donors instead of LPs

Examples include Andreessen Horowitz’s TxO (Talent x Opportunity) Initiative and Fifth Star Funds, which allows donors to write “Friends & Family” checks for Black tech founders.

Cyan Banister, once homeless, was an angel investor in Uber, SpaceX, and DeepMind

Cyan Banister has invested in more than 100 companies, building a reputation in the angel-investing world for her unorthodox approach.

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.

Venture capital is a form of funding provided to early-stage companies with high growth potential, typically in exchange for an equity (or ownership) stake

The Recount explains why girlbosses get accused of being 'white feminists'

In a video, a podcaster interviews an expert on the girlboss movement and a separate expert on “white feminism” in an attempt to understand how these two ideas intersect and overlap. It also includes a definition of white feminism and an explanation of how it differs from other types of feminist thought.

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.

Whitney Wolfe Herd is considered the youngest self-made female billionaire

Whitney Wolfe Herd founded dating app Bumble in her 20s after cofounding Tinder. She was inspired to create Bumble partly due to an experience she had with female friends who made fun of her for making the first move with a man she went on a date with.

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.

Y Combinator was founded in 2005 to bridge gaps between founders and investors

In one of Paul Graham’s essays on his website, he took the time to explain how and why he and his cofounders (including his girlfriend at the time, and now wife, Jessica Livingston), came up with the idea of and eventually created Y Combinator.

'The Fund' exposed culture problems and scandals at Bridgewater Associates

In 2023, Rob Copeland—who covered Bridgewater Associates for The Wall Street Journal for 10 years before moving to The New York Times—wrote a book that drew from interviews, company documents, and meeting recordings. "The Fund" highlighted sexual harassment scandals, a company contract to hire strippers, and a toxic company culture. Dalio has criticized the author for being sensational and a gossip.

Cathie Wood is one of the most famous modern figures in ETF investing

Cathie Wood is the fund manager and stock picker behind Ark Invest and its flagship Ark Innovation ETF. Her strategy centers around disruptive technology, and she’s made bold bets on cryptocurrency and companies like Tesla, Robinhood, and Nvidia. Wood has a loyal following of retail investors who watch her daily trades religiously.

One Facebook investor turned $500K into $1B

Peter Thiel was Facebook's first big investor. In 2004, he invested $500K into the social network, long before the company owned Instagram or renamed itself "Meta." In 2012, when he sold off most of his stake, he turned that initial $500K investment into more than $1B in cash.

Sam Altman gave his first-ever startup pitch after dropping out of Stanford

He dropped out of Stanford to start Loopt, which sold in 2012 for $43.4M. You can watch his first-ever startup pitch in a video.

A Nantucket woman helped build Macy’s

Margaret Getchell, an early Macy’s superintendent, was among the first female executives in the American retail industry. Getchell (who was distantly related to Macy’s founder RH Macy, although it’s unclear if the pair knew that when she was hired) helped shape Macy's as an early employee.

Trader Joe's hired a college student to advise on health food lingo

The grocer jumped into the 1970s health food movement by selling granola, fresh juice, nuts, and raw milk. Joe Coulombe, the company’s founder and namesake, hired “a young hippie woman” from the University of California at Santa Cruz to teach employees the language of the health food movement to properly label their products.

'I got my start by giving myself a start.'

- Businesswoman Madam C. J. Walker (1867-1919)

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.

Nike cofounder Phil Knight once taught accounting classes at Portland State University

Before Nike took off, Phil Knight taught accounting classes at Portland State. He met two very important people there: his wife Penelope and Carolyn Davidson, who designed Nike’s logo.

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 woman who made the Met Gala a pop culture phenomenon

The Met Gala began in 1948 to raise money for the Metropolitan Museum of Art's fashion collection. But its current incarnation as an over-the-top media spectacle began with former Vogue editor Diana Vreeland, who shifted the event from a stuffy, high society fair into a celebrity-focused event aimed at garnering publicity. This history of the event and Vreeland’s influence explores how she made that happen.

Up to a million Girl Scouts sell about 200 million cookie boxes every spring, generating $800 million, largely because refusing a child is frowned upon

A Yale student wrote a profound essay about the consulting industry's influence on elite college students that was published in a book of her writing after she died in a post-graduation car accident.

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

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 name 'Silicon Valley' arose from the founding of Shockley Semiconductor Laboratory in Fairchild Semiconductor in 1956-57, founded near Stanford University in Palo Alto

While the first exchange-traded fund (a 'basket' of different assets that can be bought and sold on a stock exchange) in the US only launched in 1993, the global ETF market has grown to more than $10T in the short time since.

One of the most famous portraits ever taken is 'Afghan Girl' (1984) by Steve McCurry, yet the subject Sharbat Gula went much of her life without being identified or benefitting from the image's success.

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.

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.

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.

The Nasdaq's 'Magnificent 7' companies are responsible for roughly 40% of the Nasdaq 100 index's gains, while the remaining 93 companies account for the other 60%.

Children are now three times more likely to say they want to be a YouTuber when they grow up than an astronaut, with some even attending 'YouTube camps' that teach kids how to create content for the platform.

The most expensive ad of all time was for Chanel No. 5 perfume and cost roughly $33M to produce in 2004—about $57M in today's dollars.

The hormonal disorder PCOS was renamed PMOS in 2026, a move designed to improve care and research by shifting the focus to the hormonal causes of this condition that affects 1 in 8 women.

Quincy Jones' 'Big Band Bossa Nova' helped introduce bossa nova—a jazz-influenced Brazilian genre—to the US

American short story writer Flannery O'Connor raised 40 peacocks, which became potent symbols for her fiction's elegant violence

For centuries, Niagara Falls has been a magnet for daredevils seeking to conquer one of nature's most powerful wonders, with its 200-foot drop and water rushing at 32 feet per second with 280 tons of force.

Memecoins are a type of cryptocurrency—a form of digital currency with a wide variety of uses—created around popular 'memes,' or viral internet jokes.

Comedy legend Catherine O'Hara, star of 'Schitt's Creek' and 'Home Alone,' quit 'Saturday Night Live' after just one week to return to her old job.

In 1939, baseball star Lou Gehrig delivered his inspirational 'Luckiest Man' speech after retiring due to the health condition that now bears his name.

Domino's Pizza's 30-minute delivery guarantee was responsible for the chain's 1980s surge, but it was discontinued after the company was found liable for delivery driver accidents.

Graffiti dates back to at least ancient Pompeii, where citizens scrawled messages to one another on public walls

The first robot in literature may have been a 'mechanical man' in 1907's 'Ozma of Oz,' a book in L Frank Baum's 'Wizard of Oz' series.

After her fellow cult members tried to kill her with an LSD-infused hamburger, one member of the Manson Family, the murderous cult led by Charles Manson, decided to testify against the group's leader.