In Silicon Valley, no investment has sparked as much debate as Andreessen Horowitz’s $350 million bet on Adam Neumann, the controversial cofounder of WeWork. Once hailed as a visionary, Neumann’s reputation plummeted after WeWork’s failed IPO in 2019 exposed reckless spending, governance issues, and inflated valuations. Yet just three years later, venture capital giant A16z handed him one of the largest early-stage checks in history to fund his new residential real estate startup, Flow.
Ben Horowitz, cofounder and general partner at A16z, now says the move may turn out to be one of the firm’s best investments — and he has a simple explanation for why the firm chose to back Neumann despite his past.
A Controversial Bet That Sparked Backlash
When A16z announced its Flow investment in 2022, the response was swift and scathing. Critics questioned why one of the most respected firms in venture capital would place such a massive bet on a founder whose last company imploded so spectacularly.
Tech investor Jason Calacanis summed up the skepticism on X (formerly Twitter), writing: “A startup worth $1 billion before it launches a product is probably a scam.”
Horowitz admitted on Lenny’s Podcast that Flow was “the single most controversial investment that we ever made.” He added:
“We got called everything from stupid to sexist to racist for literally just funding Adam. But I think it’s going to end up being one of the best investments we ever made. He’s doing a phenomenal job there.”
Flow’s Vision: A New Kind of Community
Flow’s mission is to reimagine how people experience apartment living, much like WeWork tried to reinvent the office. The company seeks to build branded, community-driven spaces that offer more than just four walls — complete with perks, amenities, and a sense of belonging for renters.
For Horowitz, Flow represented not just a business opportunity but also a chance to bet on a founder who had already proven his ability to scale a globally recognized brand. Despite WeWork’s collapse, its impact on how people think about shared spaces remains undeniable.
“You Don’t Judge a Person by Their Worst Moment”
At the heart of A16z’s decision was a simple principle: don’t define someone by their biggest failure.
“You don’t judge a person by the worst thing that ever happened to them,” Horowitz said. “We’ve all had bad things happen to us. We’ve all made bad decisions. Most of them, they don’t make a miniseries about, right?”
The “miniseries” was a reference to WeCrashed, the Apple TV+ dramatization of WeWork’s rise and fall that aired in March 2022, just months before A16z announced its Flow investment. The show, starring Jared Leto as Adam Neumann and Anne Hathaway as his wife Rebekah, cemented Neumann’s reputation as one of tech’s most infamous founders.
Learning From WeWork’s Collapse
Horowitz acknowledged the many missteps at WeWork but argued that most stemmed from Neumann’s inexperience and poor counsel rather than malice.
“If you really unravel the things that went wrong, most of it was a combination of inexperience and nobody around him that would tell him the truth,” Horowitz explained. “Maybe he wasn’t good at listening to the truth either at the time.”
Even so, Horowitz believes those are not reasons to dismiss Neumann as a visionary. “He built a commercial real estate brand that everybody knows,” he said — something few entrepreneurs can claim.
A Pattern of Betting on Controversial Founders
Backing Neumann is not the only time A16z has chosen to support a founder with a checkered past. The firm has invested in Munjal Shah, whose previous company went bankrupt in 2023, and even hired Daniel Penny, the Marine veteran who was acquitted in the high-profile subway killing of Jordan Neely.
To Horowitz, these decisions reflect a larger philosophy at A16z: betting on strengths rather than obsessing over weaknesses. “Judge people on what they can do. Coach people on what they can do. Help them take their strengths and use them, as opposed to overfocusing on their weaknesses,” he said.
Neumann’s Reflections After WeWork
In interviews since leaving WeWork, Neumann himself has admitted he made mistakes. Two years after his ousting, he said there had been “multiple lessons and multiple regrets,” acknowledging that WeWork’s $47 billion valuation “went to his head.”
While WeWork still operates today, the company is a shadow of its former self. After SoftBank poured billions into a bailout, the company filed for bankruptcy in 2023 and emerged the following year with a slimmed-down structure and new leadership.
The Role of Marc Andreessen
Interestingly, the Flow deal began with A16z cofounder Marc Andreessen, not Horowitz. Horowitz revealed that Andreessen was the first to pick up the phone and ask Neumann what he was working on after WeWork. That conversation laid the foundation for what became one of the most discussed venture capital deals of the decade.
“That’s probably the biggest secret there,” Horowitz said. “Marc called him. Judge people on what they can do.”
Final Thoughts: A Risk Worth Taking?
For Andreessen Horowitz, the Flow investment is more than just a business deal — it’s a statement about second chances, resilience, and the firm’s willingness to embrace controversy in pursuit of outsized returns.
Whether Flow succeeds or fails remains to be seen, but Horowitz is confident: “I think it’s going to end up being one of the best investments we ever made.”
For Adam Neumann, it’s a chance to prove that the lessons of WeWork’s collapse can fuel a more disciplined, sustainable second act.
