How one millennial played the stock market to quit his white-collar job and retire in his 40s

Business Insider

18 hours ago

William Shippey, 44, hasn't worked in about two years.
The former bank analyst says he's confident he'll probably never have to work again, apart from maybe on some side projects he'll consider picking up in the future to pass his free time.
Beyond checking the stock market in the morning — and occasionally, making a trade or two — he describes his life as largely untethered from adult responsibilities, with most of his waking hours spent working in his yard.
Shippey has around $800,000 in his brokerage account and said he expected to make around $7,000 this month in investment dividends, according to financial statements and screenshots of his brokerage account shared with Business Insider.
Besides a Tesla he purchased in 2023, Shippey says he and his wife live pretty frugally, which also helps add to their sense of financial security. The couple lives child-free and rent-free in a garage apartment in South Carolina, which they secured through a family connection.
Each month, he withdraws around $3,500 from his investment portfolio. He hands $3,000 to his wife to handle bills, like their health insurance. The remainder is fun money he can spend on his hobbies.
"I have no rent. I have no mortgage. I don't have kids," Shippey told BI in an interview. "For all intents and purposes, I'm retired."
One in a million
Shippey is part of a tiny group of day traders that have actually made money over time. He's among the wave of Gen Z and millennials who flooded the market during the pandemic stock boom, many of whom were flush with pandemic stimulus and had plentiful free time amid lockdowns and work from home.
But, unlike the majority of retail traders, Shippey's trades have been wildly successful. One 2020 study found that 97% of investors who traded for more than 300 days lost money, while less than 1% earned $54 or more a day.
Shippey says he first opened up a Robinhood account and began trading in 2022, around the time r/ WallStreetBets, Roaring Kitty, and GameStop kicked off the meme stock boom.
He funded his account with around $20,000 in spare cash and tried his hand at trading options and swing trading key stocks. Besides an undergraduate accounting degree and some time working in commercial credit analysis at banks, his knowledge of markets is self-taught, he said.
In 2023, Shippey's investments got an unexpected boost from an inheritance his mother left him, which included her life savings as well as his father's, who died in 2009.
He quit his job at the time to sort out family affairs and sell his mother's home. In between the chaos, he sowed around $400,000 into his brokerage account to start trading on a wider scale.
That's when Shippey says his luck really took off. In 2024, the S&P 500 rallied more than 20%, and Shippey made around $400,000 in profit, his brokerage statement shows.
He attributes his profits to deploying a few well-timed trades at various points in his investing journey.
1. Selling back to options traders.
Shippey says he closely followed Keith Gill, the Reddit user known as "Roaring Kitty" and closely documented his purchases of GameStop during the meme stock frenzy.
Some of Gill's social media posts included the strike price of his calls, which is the price at which the contract gives the trader the option to buy the underlying asset.
Shippey, who knew Gill had a cult following among retail traders, saw an opportunity. When Gill purchased call options on GameStop, Shippey purchased the same ones, but with a strike price $1 below Gill's. That made him a "boatload" of money, he said, as investors were still willing to pile into the trade so long as Gill still held the call.
"I would not necessarily call it gambling," he said, pointing to the retail options investors who jumped into the market during the pandemic. "Those are the gamblers. They're taking very big risks, and I'm trying to buy a slice of risk and then sell all the risk beyond that to those guys."
2. Trading high-interest stocks at strategic moments.
When Shippey was more actively trading, he focused on a handful of large-cap names he believed in — stocks like Amazon, Nvidia, Microsoft, Occidental Petroleum, and Walmart.
GameStop was the only meme stock he ever dabbled in, he says, which he only traded due to Gill publishing his strike price online.
Shippey also said he focused on diversifying his options trading portfolio and purchasing investments at strategic moments. Around the time Elon Musk renewed his fight with Donald Trump in June, he purchased around 200 shares of Tesla, waited for the stock to go up by several dollars, and sold his position. He repeated that several times and made around $1,200 in profit by the closing bell.
3. Betting big on bonds and dividend stocks.
There's one thing Shippey now favors above all else: stocks that pay a dividend.
That's partly due to fears for what could happen to markets and the economy as a result of President Donald Trump's tariffs. In Shippey's view, the US could enter a "substantial" recession in the coming year, and he's looking to wait out the volatility in stocks.
Shippey now rarely trades. Around Liberation Day, he sold most of his portfolio and plowed the majority of his wealth in the iShares 20+ Year Treasury Bond ETF, from which he expects a $7,000 dividend this month, he told BI.
Shippey predicts the ETF could rally around 15%, mostly due to the economy being in a "very iffy situation."
Living stress-free
Shippey says he's enjoying his life now, especially since he doesn't have a boss. Prior to becoming a day trader, he wore many hats, from working as a pizza maker at Papa John's, to an analyst at several financial firms, to a crew member at Home Depot. He stocked medical supplies at a hospital, and, most recently, he worked in the warehouse of a beer company.
"I've had bosses who were saints, and I've had other bosses that were completely just awful people. And no matter how you look at all that, if you didn't have to put yourself through that and you go on with your life and do something that you find fulfilling, would you do that instead?"
The stress of trading does get to him at times, particularly on big days when the market is down. On the day he spoke to Business Insider, his portfolio lost $15,000 amid a broader market sell-off. But, between his large portfolio and no-frills lifestyle, he says he's able to stomach the chaos most days and feel financially stable.
"It'd be great to make more money. I would love to make more money. That would just make you that much more comfortable. But at the same time, if I go sideways from here to the end of my life, I'll be okay."
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