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Meet the Real Estate CEO Who’s Betting Big on NFTs

Chris Okada has bet big before. In 2005, he put his entire life savings of $30,000 on the line to create his own firm, Okada & Company. You could argue that he didn’t have to since he had a chance to take over his late father’s real estate firm (Okada International Corporation) when his father was gearing up for retirement. But no, Okada wanted to strike out on his own. Since opening Okada & Company, he turned his initial $30,000 investment into an enterprise that’s conducted over a billion dollars in real estate transactions. Okada is no stranger to diving headfirst into a new venture, whether it’s music or a real estate documentary. Now he is pioneering a new frontier in real estate by being the first broker to list an office building as an NFT.

Unlikely influences

Chris Okada

For a CEO, Okada certainly looks the part. The stamp left from his short-lived tenure in the fashion industry was very apparent when I met him. All of his clothing was made-to-measure, his shoes shone from an immaculate polish, and not a hair was out of place. If I told you that this guy started out as a 90’s hip-hop DJ, you likely would not believe me. 

You can talk to him about music for hours. He’ll gush about the grungy reverbs of Nirvana, Mary J. Blige’s lyrical storytelling, and Linkin Park’s lasting legacy for as long as you will let him. The same can be said about his reminiscing on his DJ heydays. “I used to mashup hardcore nineties hip-hop with gangsta rap, which was hilarious because a lot of the time I was performing for wealthy prep school kids,” said Okada with a smile. “But hey, they loved it, and so did I.” 

Like the genre-bending influences of the 90s that he drew from, Okada is hard to pin down, but his zeal for music really set the stage for his career in commercial real estate, albeit indirectly. Growing up, real estate was always on his periphery since his family was so ingrained in the business, but he was too consumed with his musical passions to take much notice. I asked him how his stint in such a wildly different sector shaped his lens for the commercial real estate business, and it turns out that DJ-ing gave him an intense appreciation for the grind of selling office buildings.

“I thought I gave it my all when I was a DJ. I had business plans and I reached out to a handful of venues, but I never really took action. Taking action in the world of real estate is making thousands of calls, getting in front of people and giving a presentation, and just getting out there to find a deal.”

Resilience of Real Estate

Okada & Company came into fruition in 2006, just in time to see one of the worst financial crises in history, but they leveraged the market meltdown by pivoting to dealing with distressed debt in the final quarter of 2008. As Okada tells it, there had been prime corners of Manhattan real estate that developers had overpaid for at the height of the market. The best example of this was a $500 million mortgage that Lehman Brothers had on a building in Times Square, which Okada managed to sell at a discount of around 60 percent. 

As the market began to recover, Okada began investing in property developments in Midtown Manhattan. It’s a story Okada & Company has touted time and time again to attribute their success, but Okada himself believes that it’s the resilient nature of New York City real estate that’s propelled his business forward. So much so that he made a documentary about it. 

The Resilient: A New York City Real Estate Documentary was Okada’s deep respect for New York City while paying homage to his music idols. The first episode of the documentary series opens with overlapping images of the September 11th attacks with Linkin Park’s Crawling in My Skin blasting in the background, before commencing a series of interviews with some formidable figures in NYC real estate. One of them just so happens to be Okada himself. “I wanted to do something that was a creative project that honored what this city has managed to pull itself up from,” he explained. “And as New Yorkers, we’ve been through September 11th, we’ve been through the financial crisis, Hurricane Sandy, all of that, just within the past few years. Resilience is the one characteristic of any person that wants to make something of themselves, and that’s NYC to a tee.”

“I wanted to do something that was a creative project that honored what this city has managed to pull itself up from. And as New Yorkers, we’ve been through September 11th, we’ve been through the financial crisis, Hurricane Sandy, all of that, just within the past few years. Resilience is the one characteristic of any person that wants to make something of themselves, and that’s NYC to a tee.”

When I initially spoke to him, Okada was wracking his brain on how else he could make NYC’s real estate stand out from other markets. He initially tossed around the idea of starting an event on par with the Met Gala, but that hadn’t taken shape, nor did anything else he could think of. “We have 43 buildings, right? So is there something fun that, you know, that we could think of or do that would sort of highlight those buildings?” He slumped a little in his chair as he sighed. “I don’t really have an answer for that right now.” 

But it looks like his Eureka moment finally came to him, because sometime after our meeting, it was announced that Okada & Company made headlines by putting the very first office building in New York City as an NFT on the market. 

Tales from the Crypt-o 

For those still unsure about what digital assets entail, NFTs (short for non-fungible tokens) are immutable digital assets that are purchased with cryptocurrencies. These assets grant secure ownership via the blockchain, a decentralized public ledger where digital ownership can be tracked and sold. NFTs can be used to transfer ownership rights to physical goods as long as the object’s title or ownership contract is connected to the NFT in some way. Usually, NFTs come in the form of digital artworks, but Okada’s listing for an office building is the first of its kind, at least in New York City.

I was initially surprised to hear the news that Okada was jumping on the bandwagon of digital tokens for real estate since he had lamented how much his crypto portfolio had taken a hit at the end of our interview. It was an aside, a quick comment on the volatility of the cryptocurrency market. But even so, if there’s one thing to know about Okada, it’s that he loves putting unconventional things together to see what melodies play out. 

Digital real estate is definitely a new wave in the market, but listing a property as an NFT is dicey, to begin with. The Securities and Exchange Commission (SEC) has yet to define whether or not NFTs are a security. Even so, the majority of NFTs, as the public currently uses them, are unlikely to be considered securities. So when it comes to the property in question, Okada’s team needs to be extremely careful in how they carry out the transaction. 

109-111 West 24th Street hit OpenSea, an online non-fungible token marketplace headquartered, for $29.5 million or 15,105 Ether, (the cryptocurrency used to purchase said NFT). The listing quickly garnered a lot of media hype as a revolutionary turn for the metaverse. But then, the value of Ether plummeted, taking the dollar value down with it.

I reached out to Okada about the price drop, and he told me the dollar amount would not change, but the cryptocurrency used to purchase the NFT did. The property has since been re-listed at 26,500 ETH, but it’s has also been listed at $29.5 million USDC, a cryptocurrency that’s known as a “stablecoin” as its value is pegged to that of the US dollar. In an exclusive statement to Propmodo, Okada also had this to say: “As the old adage goes, ‘what got you here, ain’t gonna get you there.’ The One Eleven NFT is one possible investment strategy of taking high-growth money created in crypto and converting that to a steady stream of monthly passive income, with NYC commercial real estate’s historic appreciation. We left the listing up to see what happens, to learn from it, analyze it, and then tweak our NFT strategy using that information. Real estate is a much larger and slower-moving ship, and those strategies should not move as fast or shift as fast as one would want in the Web3 world.”

As of now, the property is still on the market, but Okada is not viewing that as a loss. The world of cryptocurrency is such a messy, speculative sphere, but “crypto” is a powerful buzzword. Some could speculate that this is a mere marketing ploy. After all, who else knows how to play up hype than a DJ? But Okada’s sitting back, and waiting to see how the world of real estate will respond to his latest mashup. Whatever the case may be, Chris Okada is willing to take big bets, whether that’s more of a testament to his character or his business ethos is up for debate, but the result is the same.

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