Adam Neumann Says a 30-Minute Car Ride Destroyed WeWork

Adam Neumann attributes the collapse of his $47 billion coworking empire to a single, impromptu conversation in the back seat of a car. The WeWork cofounder says a late-2016 meeting with SoftBank Group founder Masayoshi Son derailed a board-approved strategy designed to slow growth and push the company toward profitability.

Instead of raising the $300 million to $400 million WeWork’s directors had authorized, Neumann walked away from the encounter with a commitment for roughly $4.2 billion. Son, rushing to meet then–President-elect Donald Trump, invited Neumann to continue their discussion inside his vehicle after spending only about 12 minutes in WeWork’s lobby. The two men signed terms on an iPad before Son exited near 54th Street in Manhattan. Neumann said he walked the remaining 36 blocks back to headquarters at 18th Street having entirely abandoned the company’s original mission.

That injection of capital accelerated a trajectory that ended in one of the most notorious corporate failures in modern venture history. SoftBank ultimately poured $4.4 billion into WeWork following the 2017 announcement. Flush with cash, the company adopted a structurally flawed business model: signing long-term commercial leases in expensive global markets while renting desk space to members on short-term commitments. Neumann acknowledged the mismatch publicly, noting the inherent risk of pairing extended liabilities with transient revenue streams.

The financial consequences compounded rapidly. WeWork disclosed a $1.9 billion net loss for 2018. By March 2019, Forbes estimated Neumann’s personal net worth at $4.1 billion. Corporate funds underwrote a lifestyle that included a roughly $60 million Gulfstream G650ER jet used extensively by the founder, a residential real estate portfolio amassed with his wife Rebekah Neumann valued at approximately $90 million, and WeGrow, a for-profit private school led by Rebekah.

When WeWork published its initial public offering prospectus in August 2019—a document that famously declared a mission to “elevate the world’s consciousness”—public market investors rejected the valuation and Neumann’s concentrated voting power. The IPO was shelved. Neumann was forced out as CEO the following month, dropping from overseeing 13,000 employees to three within a week.

The subsequent pandemic-driven evacuation of office spaces in 2020 sealed the company’s fate. WeWork filed for Chapter 11 bankruptcy protection in November 2023 carrying nearly $19 billion in debt. Neumann attempted a comeback in early 2024, assembling a reported financing package exceeding $500 million to repurchase the firm, but creditors rejected the bid. WeWork emerged from restructuring later that year without its founder.

Now 47, Neumann is applying those lessons to Flow, a residential real estate startup launched in 2022. The venture secured a $350 million investment from Andreessen Horowitz, marking one of the largest seed-stage funding rounds ever recorded in Silicon Valley. Unlike WeWork’s commercial lease arbitrage, Flow targets the multifamily housing sector, aiming to build a branded network of apartment communities with integrated technology and tenant services. Marc Andreessen personally backed the project despite the widespread industry skepticism surrounding Neumann’s return.

Neumann frames his current approach around mortality rather than metrics. Speaking on The Diary of a CEO podcast in an episode released Sept. 28, he argued that defining success through wealth accumulation guarantees dissatisfaction. He now evaluates decisions based on how he expects to feel at the end of his life, asserting that ego dissolves completely in a person’s final moments.

Flow has spent its first years acquiring properties primarily in Florida and expanding its operational footprint. The company continues to scale its portfolio of managed apartment buildings across the southeastern United States.