Why did WeWork fail and why it's still around

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.

The full story of WeWork, one of the most dramatic startup journeys of all time

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.

WeWork’s competitors in the coworking space include Industrious and The Malin

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.

‘I realized after I got there it was a cult,’ one former WeWork executive said

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.

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

In the years leading up to WeWork’s bankruptcy, the tech holding company SoftBank invested roughly $16B into the company.

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.

WeWork filed its first S-1 in 2019

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

WeWork marketed itself on community

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.

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.

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.

WeWork held controversial ‘summer camp’ retreats for employees

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

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.

The Wing was a coworking space and private members club before it closed down

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.

Adam Neumann started another real estate company after WeWork

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.

In the beginning, there was Adam (Neumann)

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.

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 can't we just turn the empty offices into apartments?

As both rent prices and mortgage rates rise across the US, many companies have simultaneously continued operating hybrid or remote workforces post-pandemic. A podcast episode dives into why city dwellers aren't all living in their prepandemic break rooms just yet.

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.

In 2025, Weight Watchers filed for Chapter 11 bankruptcy after reporting revenue and profit losses for multiple consecutive years, with its stock price losing about 99% of its value between 2018 and 2025.

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.

WellHub is a startup serving roughly 4 million people in 11 countries, providing broad wellness benefits to employees

Valued at $2.4B in 2025, the company helps workers get gym access and meditation apps, in addition to basic healthcare. Listen to the founder of the company, Cesar Cevalho, explain how he scaled the company with Jeff Berman.

Remote work offers a way for companies to save money on office space

Before the pandemic, real estate costs were between 3% to 9% of the typical S&P 500 company's budget (with the exception of companies in the energy industry). Eliminating some or all of a company's expensive office leases is one way that companies can save money by adopting work-from-home models. (Some users may experience a paywall.)

Explaining the collapse of Silicon Valley Bank

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.

Airbnb's Brian Chesky explains 'Founder Mode' and how he took back control

The short-term rental CEO learned hard lessons through the pandemic, specifically around a culture focused on management and not building products. In the fall of 2024, Chesky gave a well-received speech at a startup conference that prompted debate in the startup world. He summarizes the talk here.

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.

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.

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 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.

A Wall Street Journal podcast examines allegations inside the WEF

In this episode of "The Journal," WSJ reporter Shalini Ramachandran investigates claims from current and former employees that the organization behind Davos fostered a toxic workplace, sparked by an anonymous whistleblower letter in 2025 and internal accounts.

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

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

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.

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.

Understanding TikTok-owner ByteDance's business model

ByteDance has ridden TikTok's major success to become the world's most valuable startup. This deep dive showcases some of the company's smartest moves and tactics, and where it's headed next.

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.

FTX, one of the world's largest crypto exchanges, collapsed in 2022

As crypto markets declined during the post-pandemic slowdown, Sam Bankman-Fried propped up the markets with billions he'd earned leading FTX, one of the largest crypto exchanges. Then, in one of the most rapid financial implosions in modern history, the exchange collapsed as investors rushed to withdraw money.

The evolution of X, from startup to Musk-owned giant, reflects rapid tech shifts

Twitter began in 2006 as a side project and grew into a major global platform, widely used for news, activism, and political discourse. Despite mainstream success, it faced ongoing management turmoil, business struggles, and rising concerns over misinformation and user safety.

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.

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.

Visualizing the financial troubles of FTX at the time of its bankruptcy

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.

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.

2023's worst performing US IPOs

While an IPO is a huge milestone, it isn't always a total success in the long-term. This data visualization shows some of the worst-performing IPOs of 2023, based on their percentage returns at the end of the year, It includes an NFT gaming company and a Chinese EV battery company.

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.

The Failure Museum is a curated collection of over 1,000 items representing failed products and companies

Sean Jacobsohn, a tech investor and founder of the Failure Museum, uses items from failed businesses to explain the six primary forces behind their flops, from a Theranos mug to a Blockbuster membership card.

Bezos has frequently cited a 1999 article titled Amazon.bomb to illustrate how dire the early predictions about Amazon got

Over the years, Amazon founder Jeff Bezos often recalls how wrong the predictions in the 1999 Barron’s cover story were. Among other things, that article declared Amazon’s entire business model to be unsustainable and destined to fail, noting its lack of profit and dependence on a massive amount of capital to fund its growth.

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.

The overnight collapse of Ello, a beloved, decade-old social network

Ello launched in 2014 with big dreams to avoid advertising and retain a user-friendly, simple style. But in 2023, the hip social network suddenly shut down, removing nine years of posts with no warning. Artists, writers, and other creators lost nearly a decade of work with no explanation. Read the troubling story here.

The 1929 stock market crash is a defining example of a financial bubble burst

Fueled by margin speculation and intense optimism, stock prices soared to unsustainable levels before collapsing in late October—erasing billions in market value within days.

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.

Surviving the crash: a personal story of burnout

Jennifer Moss founded a tech company, had a baby in the middle of the start-up process, and crashed after months of rising exhaustion and disconnection from a career she once felt passionate about. She shared her story of burnout and the techniques she used to turn her life around and repair her relationships in this piece.