Tony Hsieh: The billionaire who didn’t act like a billionaire

It was a million-dollar question, posed by a billionaire.

“Are you happy doing what you’re doing?”

It was kind of a strange thing to ask Zubin Damania in 2009, voiced by his friend, Tony Hsieh.

Back then, Damania was nearing a decade on the job as a hospitalist specializing in acutely ill patients at Stanford, where his wife also worked as a radiologist, having earned one of the more prestigious positions in the field.

To an outsider, he was living a doctor’s dream.

Except that he wasn’t.

And so when Hsieh, who died Nov. 27 at age 46, inquired about his contentment with his career, it was like a mental levee breaking, unleashing a flood of life-changing creativity.

“That question was enough for me to just go, ‘Wait, no, I’m not happy. I’ve reached the limit of happiness here. This is not it,’” Damania recalls. “He said, ‘If you could do anything you want to do, what would you do?’ I go, ‘Well, I’d probably make educational and funny videos on YouTube that teach people medicine.’ He’s like, ‘Then why the hell aren’t you doing that?’

Within months, ZDoggMD was born.

Damania’s wild-eyed alter-ego frequently likened to a “Weird” Al Yankovic of medicine, ZDoggMD would become a viral sensation with his oft-downloaded parody videos, which transformed hits from such stars as Taylor Swift, Michael Jackson and The Kinks into equally tongue-in-cheek, clever and informative clips on everything from the dangers of prescription drug abuse to sing-alongs about Ebola.

They racked up tens of millions of views while earning Damania an online presence of nearly 2.5 million followers on his social media platforms.

And it all began with that conversation during a visit to Hsieh’s then-home in Southern Highlands, not long after Hsieh had sold Zappos and was finishing the manuscript of his book, “Delivering Happiness.”

Damania had known Hsieh since 1999, the year he met his future wife, radiologist Jennifer Lin, who had gone to school with Hsieh at Harvard. They lived in the same dorm and became friends. She knew him long before he was rich and famous.

When Damania met Hsieh, he saw a kindred spirit of sorts, a man who diligently learned the ins and outs of an industry before feeling confined by it — and then attempting to blow it apart.

“Here is this Harvard computer science guy who goes to work for Oracle learning database software. I mean, how in-the-box is that?” Damania says. “But he optimized that. He had to go through that in order to transcend it.

“I actually think that’s a lesson for all of us,” he continues. “For me, I had to do 10 years as a hospital doctor, in the trenches, in order to see how we could transcend the normal ways we do medicine. The only reason I was able to do that is that Tony pointed the way.”

‘He was the real deal’

It was 4 a.m., and there was the celebrated entrepreneur going all Spider-Man on her building.

You still hear the incredulity in Ava Berman’s voice as she recalls walking out of the Fremont Country Club-Backstage Bar & Billiards complex that she owns with her husband, “Big Daddy” Carlos Adley, one night and seeing Tony Hsieh scaling the brick facade.

“Tony was with a bunch of friends and he was, like, rock climbing our building,” she remembers. “He was probably a good 20-feet up. I’m like, ‘What are you doing? You’re going to kill yourself.’”

Word of Hsieh’s shenanigans quickly spread.

“It became a social media thing, like, ‘If you’re in downtown Las Vegas, go rock climb the 601 building,’” Berman says of the property, which is located at 601 Fremont St. “We had to start putting signs up.”

In Hsieh, Berman and Adley found an ideal running buddy: Like him, they launched their own businesses in their 20s, becoming entrenched in the L.A. nightlife scene where both ran various clubs, with the couple opening their Hollywood restaurant and ultra-lounge La Velvet Margarita Cantina in 2004, which Hsieh used to fly out in his private jet to dine at.

“We were very entrepreneurial at an early age the way that he was,” says Berman. “We had a lot of that in common.

“We’d talk about all the side-hustles we had in college,” she continues. “Tony would buy whole pizzas and then sell slices to the dorm and make a profit. Stuff like that.”

When she and Adley relocated to Vegas to launch the Fremont Country Club and Backstage Bar & Billiards, which opened in 2012, Hsieh would drop by, grab a broom, and get to work.

“Here’s our billionaire friend sweeping the floors with us during the build-out,” Adley recalls.

Like Hsieh, Adley and Berman were all about bringing a new, hip energy to the East Fremont Arts District, which at the time, had scant nightlife options other than the now-shuttered Beauty Bar.

“Tony kind of took a shine to us real quick because we were doing what he wanted to create downtown,” Adley recalls. “And we told him that any great renaissance starts with music. We started taking meetings nonstop. We became very close.”

One of the things that Adley and Berman encouraged Hsieh to do was launch his own music festival, which he did with Life is Beautiful in 2013. The fest’s opening party was held at their club.

As Hsieh continued to invest in the area, Adley and Berman warned him of potentially predatorial business deals.

“We would always tell him, ‘Keep your guard up,’ because there’s a lot of people who will take advantage of your generosity — and a lot of people did that,” Adley says. “You see a billionaire, and they have an agenda.”

One of the things the two say they appreciated the most about Hsieh, though, was that he seldom carried himself like a billionaire.

“I don’t think I saw Tony once in a suit. Ever. I’m not even kidding,” Berman says. “What we always cracked up about, is that one night, he could be sitting with dignitaries, and then the next night, he’d be on a bus going to Burning Man with a bunch of stoner people.

“We just thought the dichotomy was so hilarious,” she adds. “He was the real deal.”

Seeing the world through a different lens

It all came down to the Michael Jackson parody clip about testicular cancer.

In 2012, Hsieh invited Damania and his family to relocate to Vegas and launch his own clinic, Turntable Health, as part of Hsieh’s $350 million Downtown Project initiative. While Turntable Health eventually closed in 2017, it was emblematic of both Hsieh and Damania’s shared passion for disrupting the industry status quo, in this case with “transcendent, re-personalized health care,” as Damania explains.

“When you ask him, ‘Why the hell did you pick this guy ZDogg to come to Vegas?’ ” Damania begins, “He’d say, ‘Oh, because he made this music video, ‘Manhood in the Mirror,’ which was a parody of Michael Jackson’s ‘Man in the Mirror,’ and it’s just ridiculous because he rhymed ‘metastasized’ with ‘realize’ and all this crazy stuff, and it’s just amazing.

“He saw in that this idea that you could use humor and disarming people to do something really weird, which is checking your testicles for cancer once a month,” he continues. “That was him. That’s how he saw the world. It was just a totally different lens.”

Damania notes that Hsieh was not without his personal struggles.

“You’ll hear stories about his complexities and his dark sides and the things that he got wrong — and all that is true. That’s the truth of any complex human being,” he says. “But I’ll tell you, on balance, the light he brought into the world was just … you’re not going to see it again just commonly. It just doesn’t happen like that. That’s what he gave us.”

When reflecting on his friend, Damania still speaks in the present tense in numerous instances.

It’s not because he’s reluctant to acknowledge the passing of a man who played such an influential role in his life.

It’s because he believes Hsieh’s presence is still very much alive in the many projects and people he impacted.

“He’s a catalyst, a matchmaker; he’s a facilitator, a connector,” Damania says. “That’s what I say he still is, because his influence is still right there. It’s not dead.”

Contact Jason Bracelin at jbracelin@reviewjournal.com or 702-383-0476. Follow @JasonBracelin on Twitter and @jbracelin76 on Instagram