In 2017, Steve Oliverez had a hunch.
The entrepreneur had already enjoyed a stellar run during the stock market’s “Trump bump,” but, with the year winding down, he identified what he believed to be an opportunity for reaping next-level gains.
At the time, the Republican tax overhaul was in the final stages of congressional passage, and Oliverez was convinced it would unleash a bull rush that would take the market to new highs — so he began buying up short-term, way-out-of-the-money calls on the S&P 500
Big risk, big reward. Maybe.
“Under normal circumstances, that’s a great way to throw away money, but I was using historical data from 1987, the last time such a huge tax-reform bill was passed,” he said. “With the VIX
in single digits, options were so cheap that if there was even a 1-in-50 chance of me being right and history repeating itself, then the odds were still in my favor due to the outsized potential payout.”
Oliverez was no stranger to embracing long odds. Two years earlier, he garnered 1.5 million YouTube views when he decided to throw his hat into the presidential ring. For a guy with no shot, he made quite a splash across the internet as a contender for the Republican nomination.
According to the Huffington Post, no other candidate’s campaign announcement up to that point, aside from Donald Trump’s, racked up clicks like Oliverez’s.
But he was never really serious about the whole White House thing.
“I filed just for fun … but ended up getting a fair amount of attention,” Oliverez told MarketWatch. “It was a great learning experience, too — from the YouTube comments I learned I was too liberal and that I should go back to Mexico.”
While he didn’t go back to Mexico (having been born in Virginia), the Austin, Texas–based Oliverez did go back to trying to make a killing in the stock market. The inspiration to play the tax cuts led to action, and he posted his positions in Reddit’s raucous “Wall Street Bets” community:
Plenty of Reddit commenters trashed the move. “These kind of posts are the reason 90% of [Wall Street Bets] is turning their $1,000 into $100,” one said.
But that didn’t keep Oliverez from committing to his risky play. “I started buying the options around Thanksgiving, and by the end of December, I’d sunk $100,000 into them,” he said. “If the stock market didn’t see a huge spike up very quickly in the new year I’d lose it all. Turned out to be one of the best Januarys in history. Once the options made it into the money, they started going up real fast.”
Since the 1987 period he used as a basis for the trade ended with a big crash, Oliverez quickly began to unwind his option positions. He acknowledged that he could have timed it better, considering how the rally played out, but, when it was all said and done, he’d made off with a massive profit:
At that point, he resisted the greedy urge to parlay his windfall into an even bigger fortune and basically stepped away from the trading screen.
“I bought a new house with cash, so no mortgage, car was already paid off, no student loans (dropped out of community college), and the kids’ college accounts are funded, so I don’t have a ton of monthly expenses,” he said. “I work for myself, but I was able to take most of the year off to celebrate.”
And, judging from his Instagram account, celebrate he did, living the high life and bouncing around the U.S., Southeast Asia, Japan, etc.:
As his “Wall Street Bets” brethren like to say, YOLO! “I’ve got a huge bucket list and decided it was time to start checking a lot of things off. It worked out, since 2018 ended up being a bad year for trading anyway,” Oliverez recounted. “I’d still check on the markets from my phone, but in Thailand or St. Maarten.”
He does feel the pull to make another bold play, but that won’t happen for awhile. Oliverez, who jokes that he’s an Instagram model now, is satisfied taking the safer route and sticking primarily to passive investing in U.S. equities and real estate.
“Leveraged gambles like buying options are essentially the same as playing against a casino,” he said. “Even if you get a big payout from time to time, the longer you play the more you lose.”
Read: Trader says he has ‘no money at risk,’ promptly loses 2,000%
Oliverez knows a thing or two about being caught on the wrong end, as well.
His misfires include buying $40,000 in S&P puts right before the 2016 election, wagering correctly that Trump would pull off an upset but assuming wrongly a deep selloff would ensue and stick around long enough for him to profit.
‘I learned the important lesson that if you’re right but your timing is wrong, you’re still wrong.’
“I went to bed thinking I’d made $300,000,” he said of the Election Night futures-market whipsaw. “Of course, the recovery happened by the time the markets opened, and that $40,000 was gone. I learned the important lesson that if you’re right but your timing is wrong, you’re still wrong.”
When fortune ultimately smiled on him over the following year, Oliverez compared his $2.4 million stroke of trading luck, or skill, to card counting.
“I saw a big imbalance in the risk/reward in options pricing after what had the potential to be a major market-moving event,” he said. “The thing with counting cards, though, is you spend a lot of time just waiting around.”
And Oliverez said he’s willing to wait.
“Economic growth is slowing outside the U.S., but we’re still chugging along, and with a divided government I don’t see anything major coming up that would change that,” he predicted. “There’s some upside with the trade deals in the works, but even if they fell apart U.S. equities would still be the best game in town.”
So when does he see the count turn in his favor?
“I don’t expect the next big catalyst until November of next year,” he said. “That election will have larger consequences for the future of the U.S. and equity markets than even the 2016 election.”
We’ll check back a year from November.