44-year-old William Shippey, a former bank analyst, hasn't worked in two years and enjoys a financially independent lifestyle. With $800,000 in investments generating roughly $7,000 monthly in dividends, he considers himself retired, supplementing his income with occasional side projects. Living frugally in rent-free South Carolina housing, Shippey's success story highlights the potential of shrewd day trading, defying the odds against retail investors
Former bank analyst William Shippey, 44, reveals his early retirement strategy: $800,000 in investments generating roughly $7,000 monthly in dividends. Living frugally and rent-free, he enjoys financial freedom, occasionally pursuing side projects for leisure, proving that consistent profitable day trading is possible
Financial freedom at 44: This former bank analyst traded his corporate job for a life of gardening and strategic investing, generating $7,000 monthly in dividends from his $800,000 portfolio. He spends his days tending his yard, occasionally monitoring the market, and enjoying a debt-free, child-free lifestyle with his wife. Learn how he achieved early retirement and financial independence
Retired at 44: William Shippey's $800,000 investment portfolio generates roughly $7,000 monthly in dividends, allowing him a debt-free, child-free lifestyle. Financial statements and brokerage account screenshots verified by Business Insider support these figures
Financial freedom at 44: This child-free couple enjoys a rent-free South Carolina life, supplementing their $800,000 investment portfolio with monthly dividends, allowing them to live frugally while driving a Tesla. Their smart financial strategies and successful day trading have led to early retirement
Retired at 44: This former bank analyst generates $7,000 monthly in investment dividends, withdraws $3,500 for living expenses—$3,000 for household bills and $500 for personal spending—and enjoys a debt-free, rent-free lifestyle
Financially independent at 44: This former bank analyst quit his job two years ago and hasn't looked back. With $800,000 invested and monthly dividend income exceeding $7,000, he lives a debt-free, child-free life, spending his days tending his yard and enjoying financial freedom. No rent, no mortgage, no kids – he's essentially retired, proving it's possible to achieve early retirement through smart investing
William Shippey, a former bank analyst, achieved early retirement at 44 through successful day trading. Unlike most retail investors, he's among the rare few who consistently profited, joining the wave of Gen Z and millennial traders who entered the market during the pandemic boom. His disciplined approach and frugal lifestyle, living rent-free in South Carolina, have enabled him to generate substantial investment income, securing his financial future
Unlike most retail traders who struggle, William Shippey's day trading success story is exceptional. A 2020 study revealed 97% of investors trading over 300 days lost money, while less than 1% earned over $54 daily. Shippey, however, defies these odds, achieving financial independence through shrewd market strategies
Inspired by the 2022 meme stock frenzy surrounding GameStop and WallStreetBets, 44-year-old William Shippey began his trading journey on Robinhood. This decision led to his early retirement, allowing him to focus on hobbies and enjoy financial freedom
Former bank analyst William Shippey, 44, traded his way to early retirement using a $20,000 investment in options and swing trading. With a self-taught approach to market investing, supplemented by an accounting degree and banking experience, he now boasts an $800,000 brokerage account and monthly dividend income exceeding $7,000. His story showcases the potential—albeit rare—success of retail trading
Shippey's 2023 investment portfolio received a significant boost from an unexpected inheritance, including his parents' life savings. This windfall, coupled with shrewd trading strategies, contributed to his early retirement at age 44
After leaving his banking job to manage family matters and sell his mother's house, William Shippey invested $400,000 into his brokerage account to significantly expand his trading activities
Shippey's financial success skyrocketed in 2024, with the S&P 500's 20%+ rally generating nearly $400,000 in profit. This substantial gain solidified his early retirement, fueled by savvy day trading and a frugal lifestyle
Shippey's financial success stems from strategic, well-timed trades executed throughout his investment career, enabling his early retirement at age 44
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.”
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.
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.”
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.”
Do you have a story to share about day trading, quitting work, or retirement? Contact this reporter at jsor@businessinsider.com.
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