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

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 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.

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.

This podcast episode chronicles the complete rise and fall of WeWork—from its founding in 2010 to its eventual 2023 bankruptcy.

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

WeWork has been through a lot since the office space company was founded as a startup in 2010. From its failed IPO in 2019, to the various leadership antics of its founder, Adam Neumann (some have claimed that he acted like a cult leader at times), to how it navigated remote work trends during the pandemic, this video tells the full story of WeWork's growth, failures, and more.

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.

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’s story is colored by the times it just couldn’t make its numbers work. Its competitors in the coworking industry, such as Industrious and Convene, seem to be prioritizing slow and stable financial growth instead.

WeWork isn’t only known for how it revolutionized modern work, or its spectacular financial rise and fall. It’s also known for its former cultlike company culture under former CEO Adam Neumann, complete with a charismatic leader and “summer camp” company retreats that blurred the lines between work and personal life.

In a new era of work where many millennials wanted to work for themselves in offices with exposed brick, cold brew on tap, and casual dress codes, WeWork realized these entrepreneurs and startup workers didn’t want to do it alone.

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.

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.

Former WeWork CEO Adam Neumann has attempted to purchase WeWork before, although, thus far, he hasn’t been successful. Since leaving the company, he has founded a residential real estate firm, among other projects.

Step inside one of WeWork’s “summer camp” retreats full of drugs, alcohol, and exorbitant company spending.

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.

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.

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.

In March 2023, Silicon Valley Bank—the nation's 16th largest bank at the time—collapsed after a rapid run on its deposits. Among other factors, the bank had placed more than half of its investments into long-term bonds, leaving it without the necessary cash on hand as its clients, largely start ups, panicked and withdrew their money at the same time. This visualization lays out the timeline and impact of the collapse.

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.

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.

Combined, the top seven companies by market cap in the US as of December 2024—Apple, Nvidia, Microsoft, Alphabet, Amazon, Meta, and Tesla—were worth more than $16T at the time.

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.

A third of US billionaires inherited much or all of their enormous fortunes. It can be tough to determine the exact net worth of billionaires given that much of their money is often tied up in company stocks, which fluctuate significantly in a given week.

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

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.

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.

This podcast episode, which includes a telling interview with one of WeWork's first employees, tells the origin story of WeWork—from Neumann's drinking and disheveled clothing, to WeWork's first "summer camp" company party weekends in New York.

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 level of startup funding around the world broke all previous records in Q1 2026 by a significant margin: Only $118B was raised in the previous quarter, and Q1's haul outpaced every full year of global VC activity before 2019. The increase was partly due to the enormous funding rounds from AI companies such as OpenAI and Anthropic.

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.

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.

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

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.

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.

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.

In early 2026, the company joined major tech companies Nvidia, Apple, and Meta (among others) as one of the rare firms with a market capitalization beyond $1T. See the latest top companies here.

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