With Jared Leto’s performance in the Apple+ original series “WeCrashed” still echoing, and the Emmy Awards soon upon us, is it any wonder Adam Neumann remains on the minds of the media?

In 2019, the WeWork cofounder was ousted from the CEO position of the company he launched with Miguel McKelvey. His eccentricities, including a party-all-the-time, spend-spend-spend ethos, played no small role in his downfall, though a golden parachute of $1.7 billion certainly helped cushion the landing.

As it turns out, soon after Neumann arrived in the United States some 20 years ago, he would encounter — via his sister, Adi — another Israeli-American just making his way into the world of wealthy investors:  Guy Oseary, longtime manager of Madonna, whom Variety named Music Mogul of the Year in a cover story out this week.

“I met Adam maybe his first month in America,” says Oseary, who leads the Sound Ventures tech fund with partner Ashton Kutcher. “It was way before WeWork, but he’s the same guy,” he adds. “Adam is a rare breed.”

When it comes to investing, both Oseary and Kutcher subscribe to the guiding principle of “founders first.”

As Oseary explains: “Ashton thinks: ‘Do I want to work with this person? Would I want to leave my job and work for this guy?’ I’m more on the ideas side. Like, do I love this idea enough to want to do it myself? That’s how much I love it. The other thing we look at is: can we help it? Can we really do something here? That’s the foundation. To me, it’s very similar to walking in a room and recognizing an amazing artist.”

Indeed, Oseary views founders as “the rock stars today. … They have their own music; their songs that they want to share with the world. And you have to be one hell of a leader to have people believe in you or your company in that way.”

Oseary saw firsthand some of the early WeWork buildings and confirms that in 2019, Maverick, the consortium of music managers he led — which collectively represented the likes of the Weeknd (via Wassim ‘Sal’ Slaiby), Paul McCartney (via Scott Rodger), Jason Aldean (via Clarence Spalding) and Lil Wayne (via Cortez Bryant) — along with the entity Sound Together, was considering moving its operations into a new WeWork development. Then the pandemic hit.

“If you went to any WeWork location early days, it felt like something special was coming together,” says Oseary. “You wanted to root for its success. It felt like a community of sorts. People were connecting with one other; They were finding each other there for help — ‘Oh, you do websites? Great. Can I use you?’ And, ‘Oh, you’re a lawyer?’ … I was very impressed.  It was much more than renting out space in a boring building where no one ever speaks to anyone else. This was networking in your own lobby if you wanted to. Or finding support for something you’re working on only a few floors down — not in a different city. … The seed of his and Miguel’s idea was really awesome. The potential was there. I saw it firsthand.”

Certainly both Oseary and Kutcher displayed public support of WeWork and Neumann, participating in conference talks with each other and being photographed together on more than one occasion. Was there a sense that WeWork as Neumann envisioned it could go off the rails?

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“At the rate they were growing, even the most seasoned executive in the world would have had a hard time making it work,” offers Oseary. “Unless they changed strategy all together and decided to grow very, very slowly. And slowly is not in Adams DNA.”

It’s worth noting that Oseary has also recently experienced the breakneck speed at which a new idea can drum up interest and value. As a partner in Yuga Labs, home to the popular NFT series Bored Ape Yacht Club, Oseary witnessed the digital collectibles rack up $2.3 billion in sales to date, according to CryptoSlam.io. “Digital growth is a lot different than buying up buildings, being a landlord, dealing with the daily ins and outs,” he says. “From scouting a building; to making a deal on it; to fixing it up; to doing outreach to sell; to keeping everyone happy … It’s very hard to scale all that 100 times a year all around the world with countless different set of rules and regulations.”

So what happens when the so-called cult of the founder overwhelms and supersedes common business sense? Oseary is quick to point out that Neumann is the opposite of your typical capital-seeking Silicon Valley dreamer. “Adam is different,” he says. “Anyone who has met him would absolutely remember him. He’s tall, loud, charismatic and full of energy. Hand him a microphone, a guitarist, a bassist and a drummer and he’s ready to rock. Most founders in tech are problem solvers; they have engineering backgrounds. They live in their own silo. They were not the popular kids in class. Adam was the popular guy. His sister was cool. He was in the army in Israel. He is very social and fun. Go out with him in Tel Aviv where the music is unbearably loud, Adam would ask them to turn it up! What Adam possessed, and others like him, is a level of magic that can ignite loyalty from a community. And look, there are WeWorks everywhere, and they’re still great places to work out of. The original concept was a solid one.”

As for Neumann’s future, Oseary has no doubt the self-described “serial entrepreneur” will be back, which is not something he can say about Theranos’ Elizabeth Holmes, who was also given the dramatic series treatment with Hulu’s “The Dropout” starring Amanda Seyfried.

“They’re not the same,” says Oseary of Holmes, who was found guilty on four counts of fraud in the trial stemming from the collapse of her Silicon Valley start-up, blood testing company Theranos. “Adam had the essence of a really great idea with huge potential, had he gotten to the finish line. In fact, I think Adam just raised $70 million for a new company so get ready to turn up the volume. … Adam clearly has the needed experience on what to do and what not to do the next time. He will continue to build new things. Elizabeth, on the other hand, won’t.”