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.

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.

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.

‘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'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.

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.

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.

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 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 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.

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.

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 held controversial ‘summer camp’ retreats for employees

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

Roughly 10% of US apartments were owned by private equity firms as of 2025.

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.

Citadel founder Ken Griffin has a $1.5B property portfolio

Take a look inside Griffin's real estate portfolio, from a $1B home in Palm Beach to his New York City penthouse on Billionaire's Row.

Steve Jobs founded NeXT while on a break from Apple

While Steve Jobs was on a hiatus from working at Apple, he founded a company called NeXT and helped lead the release of its operating system NeXTSTEP. The operating system was used to create the first app store of sorts, as well as the first web browser.

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.

Mark Zuckerberg credits some of Facebook's success to constant evolution

Before becoming the head of OpenAI, Sam Altman was the president of Y Combinator—a startup accelerator company that supported companies like Airbnb, DoorDash, and Coinbase. In 2016, Altman interviewed Zuckerberg about creating Facebook and its growth over time. Zuckerberg said that, unlike other companies (think: CourseMatch), Facebook kept growing and adding new features, which prevented the app from becoming obsolete.

Prediction market Polymarket's CEO dropped out of New York University

Polymarket CEO Shayne Coplan started building Polymarket when he was 21. Polymarket has been backed by billionaire investors such as Peter Thiel and Vitalik Buterin.

YC was partly inspired by an investor named Julian Weber

Y Combinator Cofounder Paul Graham’s former professor’s husband Julian Weber provided $10K in seed funding to Graham’s previous startup, Viaweb in its early days. In exchange, Weber received 10% of the company. Weber’s involvement inspired Graham to start a program where investors were more involved with the companies they contributed seed funding to.

Real estate investment firms handle enormous, complex real estate transactions

In the large-scale projects real estate investment firms handle (such as huge commercial developments), the parties involved in a sale are more likely to be large corporate real estate developers and investors than individuals.

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.

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.

Amazon founder and billionaire Jeff Bezos' wealth primarily stems from his Amazon ownership stake.

Kanye abruptly left Nike in 2013 and took his Air Yeezys to Adidas for $10M

In 2009, Kanye West became the first non-athlete Nike produced a signature shoe for. However, Kanye left Nike for the company’s rival, Adidas, just a few years later. Kanye said Nike was stifling his creative vision, and he felt like he wasn’t getting enough royalties.

Elon Musk once tried to make himself CEO of artificial intelligence behemoth and ChatGPT creator OpenAI.

Unlike other franchises, the McDonald's Corporation owns the land and the buildings of individual stores, and franchise owners lease those assets—resulting in McDonald's often being called a real-estate company.

Visualize where the first batch of founders from the famous startup accelerator Y Combinator are now.

Andreessen Horowitz is among the most well-known venture capital firms

Also known as a16z, the firm has invested in companies such as Airbnb, Facebook, and Lyft since its founding in 2009. A podcast episode offers a deep dive into how the firm got started and became the industry disruptor it is today.

Elon Musk's first company was an online business directory called 'Zip2'

Musk started the online alternative to Yellow Pages in 1995 with his younger brother. Musk sold the company for $305M in 1999.

A merger between OpenAI and Anthropic was reportedly proposed after Sam Altman's firing

OpenAI's board of directors reportedly reached out to Anthropic's CEO, Dario Amodei, about the possibility of taking over the role left by Altman in 2023. Amodei declined to take over as OpenAI's CEO and to a merger of the two AI startups.

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.

One filmmaker turned an abandoned high school into a film studio

In 2017, Jeremy Garelick purchased a vacant school in Liverpool, New York, and turned it into a comedy production studio aimed at social media. The gambit has been successful, with the studio's two TikTok accounts earning over 1M combined followers.

Investors are buying up land in the Metaverse

Real-estate transactions in the metaverse are reaching record highs. Digital real estate investors share how and why they're spending millions on virtual property.