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

SoftBank acquired a majority stake in WeWork in October 2019

SoftBank is widely considered the biggest victim in the WeWork story, losing billions of dollars that it invested in the company while WeWork’s CEO walked away a billionaire himself.

SoftBank's founder and CEO had a volatile relationship with WeWork's Adam Neumann

SoftBank CEO Masayoshi Son, as WeWork's largest financier, had been Neumann's biggest champion for years—until he volleyed for Neumann to be removed from his position as WeWork's CEO.

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.

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.

WeWork’s S-1 was full of alarming financial and business information that concerned investors and the public

When WeWork’s S-1 came out, investors were particularly concerned about WeWork’s expenses far outpacing its growing revenue and its complex company structure, as well as a few potential conflicts of interest within the company.

See the small apartment WeWork founder Adam Neumann lived in before he was a billionaire

WeWork CEO Adam Neumann used to share a relatively small apartment in New York City with his wife before he became a billionaire off of WeWork. At one point, the apartment rented for $3K per month.

WeWork makes money via flexible lease options

WeWork makes money by entering long-term leases with office buildings, then providing flexible lease options to its members on a short-term basis. Members get a refreshed, modern space to work in (with consistent coffee on tap, of course), and WeWork gets their consistent membership dues.

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.

Worth more than $14T, Silicon Valley may be getting too expensive for future founders

Silicon Valley, the 1,800-square-mile hub of tech innovation, reached more than $14T in market value in 2024. Home to industry giants like Apple and Adobe, its influence is undeniable. But rising costs and corporate relocations raise questions about its future.

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.

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.

An interview with WeBank’s CFO

Leveraging Tencent's massive WeChat network, WeBank started as China's first digital bank and now serves 340 million users and 2.8 million businesses (as of 2024). Chief Financial Officer Arthur Wang discusses how the company is using AI and continuous innovation to stay ahead of the technological curve.

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.

Steve Jobs saved a nearly bankrupt Apple

Apple nearly went bankrupt in 1997, when the tech company had only three months of operational cash left. Apple's board ousted cofounder Steve Jobs in 1985, but he was brought back as interim CEO to revive the company when Apple purchased Jobs' company, NeXT.

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.

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

7 prominent investors rejected Airbnb in its early days

Airbnb is arguably known as one of the most successful startup stories of all time. But back in 2008, many prominent investors rejected their pitch when they went out to raise money—and Airbnb's founder still has the rejection emails to prove it.

Warren Buffett was famously anti-tech stock during the 1990s dot-com boom

Buffett said that tech is something that Berkshire Hathaway doesn't "understand, so we don't invest in it." This philosophy led him not to invest in Yahoo or Microsoft during this time. (Some readers may experience a paywall.)

Tesla short sellers benefited from the company's poor performance in 2025

Tesla was widely considered the most-shorted stock until 2024, despite consistent short-seller losses. Between 2016 and 2020, short sellers reportedly lost more than $11B as Tesla's stock price continued climbing. However, long-held short positions began paying out in 2025 as Musk's foray into politics and his eventual feud with President Trump hurt Tesla's stock performance. In 2025, Tesla short sellers made more than $10B.

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.

Elon Musk's $100M investment in SpaceX was lost to three failed rocket launches

The attempts with Falcon 1 endangered the company's future but provided valuable information from which to iterate and follow up with the successful first privately funded orbital launch in history and multiple ISS resupply missions.

Dive deep into the numbers that shape each YC deal

Y Combinator invests $500K into each company in any given batch. $125K of that investment converts into a fixed 7% in ownership of the startup, and the other $375K is invested on something called an uncapped MFN safe. YC explains what that means and more terms of the deal in a detailed article on their website

How to make a billion dollars, with Brad Jacobs

Brad Jacobs is a serial entrepreneur who has launched eight billion-dollar enterprises during his storied financial career. With companies focused in energy, waste, and more, Jacobs has stuck to a roll-up playbook of consolidating small players into one conglomerate within an industry, a common tactic of similar private equity firms. This podcast from Founders summarizes Jacobs' book detailing his approach.

Twain was a notoriously bad investor

After becoming a famous writer, Twain invested in railroad stocks, a magnetic telegraph, and a printing press that weighed four tons. Eventually, he founded his own publishing company, which ultimately led to his bankruptcy. “He is, in business,” one lawyer said, “just a big overgrown boy.”

Around 60% of female billionaires in the US are considered self-made

There are 154 female billionaires in America, and around 60% of them are considered at least partially self-made—meaning some of their wealth comes from a business venture launched on their own. Alice Walton, the founder of Walmart's daughter, is the richest woman in the US, clocking a net worth of $138B. (Some users may experience a paywall.)

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.

US consumers collectively owe more than $1T to credit card companies—almost as much as they owe in auto loans.

Watch this video that uses Lego bricks to explain how venture capital works.

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

Before the current East Wing ballroom project, only two White House renovations in the past 100 years cost more than $10M.

Legendary architect Frank Lloyd Wright designed the SC Johnson headquarters in Wisconsin, aiming to make a cathedral-like workplace

In 2019, a laptop loaded with six of the worst malware in history and described as 'an exhibit of historical weaponry' sold for $1.3M.

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

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%.

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.

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.

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.

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

Use this tool to calculate the dollar value of your parental mental load, from meal planning to coordinating after-school care, then see resources that help generate solutions.

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.

See a ranking of the best (and worst) Federal Reserve Chairs since 1914 out of the 16 men and women who have held the office since.

Budweiser stores yeast derived from the original 1800s strain in a secret bunker, which only the Head of Yeast Management can access—not even the CEO

The first image of a black hole was captured by creating an Earth-sized virtual observatory from a network of eight radio telescopes.

Fast-casual restaurant Chili's is experiencing a resurgence, with its parent company recently reporting a nearly 32% increase in sales, thanks to passionate Gen Z fans on TikTok.

The Beatles' US label rejected the band's first two singles, 'Please Please Me' and 'From Me to You,' with one executive calling the band 'dead in the water.'

NBA superstar Victor Wembanyama spent the 2025 summer training with monks in central China to enhance his body and mind.

How fusion—which releases energy when two lighter atoms combine to form a heavier atom—differs from fission

Firework or sparkler burns, even if they cover a relatively small area of skin, can significantly affect our range of motion.

Brandi Chastain, the star of the 1999 US victory over China in the 1999 Women's World Cup, was a last-second choice to take the penalty kick that sealed the victory.

Gerrymandering works through two techniques: cracking opposing voters across districts to dilute their power, and packing them into a few to waste their votes in lopsided majorities.