A baby boomer who retired early turned to trading meme stocks to fight the boredom. Here’s how he’s successfully navigated the market.

Tom Rairdon, 75, began trading meme stocks after he retired early.Courtesy of Tom Rairdon

Tom Rairdon, 75, began trading meme stocks to combat boredom in retirement.
He ended up nearly doubling his portfolio in three years by trading high-volatility stocks.
He told Business Insider his strategy for passing the time while earning “Vegas money” on the side.

Nobody told Tom Rairdon how dull retirement would be.

After working in the radio industry for more than three decades, the 75-year-old officially left the workforce more than two decades ago, flush with savings and ready to enjoy the “country club life,” he told Business Insider in an interview.

Post-work life, mostly filled by rounds of golf with the boys—he played over 200 rounds in one year—ended up being far less exciting than he expected.

Then he stumbled into the market for meme stocks.

“I mean, you can only play so much golf,” Rairdon said of his retirement. “A buddy of mine suggested day trading. I went, ‘Yeah, why not?'”

As far as day traders go, Rairdon is a rarity. He's one of the many retail investors who flooded the market in 2021, back when the stock market was buoyed by a flood of pandemic stimulus and meme stock icons embodied the cultural zeitgeist.

But he's one of the few who's managed to stay profitable, despite waging bets on some of the market's most volatile assets.

Rairdon, who trades a mix of meme stocks and other high-volatility stocks out of his Roth IRA, has seen the value of his portfolio soar 82% over the last three years, with $19,000 in unrealized gains this year alone, according to a brokerage statement viewed by Business Insider.

It's not a life-changing sum. But that's of little importance to Rairdon, whose goal is more to fill his days — and, of course, make some extra “Vegas money,” he says, should the markets swing in the right direction.

“The money has never been the problem,” he said of retirement. “It's what to do.”

Being in the radio business was the best job Rairdon ever had. But, with time, the industry changed so much that it stopped being fun, leading him to quit when he was 55. From there, his dilemma began.

A 2024 survey from Resume Builder found that boredom was the second-most common reason retired Americans said they were considering going back to work in the next year.

Growing bored with the golf course, Rairdon tried his hand at a bunch of different activities. He volunteered for Reading for the Blind. He briefly launched a copier business. At 67, he became a truck driver for Whole Foods and Target, mainly because he wanted to do some sight-seeing around America.

Nothing seemed to stick until he got into the market.

“Day trading is the one lifestyle that I like, because two, three hours a day — and that includes the research — and then you're done,” Rairdon said, adding that he saw the activity as both fun and flexible. “If you want to go to a ball game or you want to go water skiing or sailing or whatever you want to do, you got plenty of time the rest of the day to do it. It's dynamite that way.”

Trading, Rairdon adds, is like a job, though his style is far more relaxed than retail investors who trade full-time. He starts his day at 8:30 am MT— well after most premarket traders — and walks his dog, Lucy. Then, he'll read up on what's going on in markets, and begin trading around 9:00 am. After an hour or so, he'll start wrapping up his positions, though on occasion he'll work “late” if there's a trade that takes a little longer.

“I mean, I treat it like a job, but like, a three-hour job,” he said, adding that he only trades two to three days a week.

Rairdon, who studied chemistry in college and is self-taught as far as financial markets go, said it took a while for him to find his groove. Here's what ended up working for him:

Focus on AI and high-volatility stocks. Rairdon said he focuses on trading high-volatility stocks, partly because the big intraday moves mean there's a higher potential to turn a quick profit.

That's one reason he takes positions on meme stocks. Rairdon got in on both GameStop and Opendoor amid the retail frenzy, he told BI.

Mainly, though, he focuses on the Magnificent Seven, AI-related stocks, and other stocks with a lot of buzz on social media.
Technical analysis. Traders should be paying close attention to a stock's technicals, ideally by having one screen for each stock they're watching, Rairdon said.

Once Rairdon identifies a stock he'd like to trade, he watches its indicators, like a stock's moving averages, and waits for an ideal “setup” or a pattern that suggests a stock could move in a certain direction.

Early in his trading career, Rairdon said he lost “a lot” of money on options because he had eight or nine positions running at a time and couldn't keep track of them all.

“The ego goes, ‘Oh, you can do it.' Well, I couldn't do it. So I backed off and started trading one or two options at a time, and that turned my game around,” he said.
Get out quickly. Rairdon says he tries to sell positions quickly—sometimes, holding a trade for just a minute—in order to minimize the the chance of steep losses.

If the trade goes well, he tries to sell as soon as he makes $100 on the position.

If the trade goes poorly, he follows a practice of immediately selling his position once it's down 8%. In his view, there's no point in averaging down, a practice where stock traders buy more shares of a stock they've lost money on in an attempt to lower their average loss per share.

“It's saved me really a lot more money than I thought it would, because I was letting my losers run too long,” he said of his rule.
Research, research, research. Rairdon doesn't trade daily, but he researches stocks seven days a week, he said, adding that he believed it was critical to be tuned into the market every day. Rairdon says he spends around 20 hours a week reading publications like the Wall Street Journal, Barron's, MarketWatch, and Business Insider.

When it comes to meme stocks, Rairdon admits he's “absolutely” gambling, but he thinks the risks he takes are calculated — and it's all part of the fun for Rairdon, who also plays poker and says he goes to Las Vegas at least once a year.

“Radio business is all high stress, so it's just like, eh, it's no big deal,” he said of some of his losing bets. “When I lose on a trade, I just forget about it and go on to the next one. Because the next one, I may win twice as much.”

To those who want to replicate his lifestyle, he only has one piece of advice: Don't do it unless you're willing to put in the work.

“To be blunt, I would not recommend anybody start day trading unless they have really researched it,” he said, adding that he encouraged younger traders to start with a paper trading account. “Do that and see if you can actually make money doing it. If you can't make money, why do it?”

Rairdon, who still has ample free time in his day, says he has a handful of exciting plans in the near future. At the moment, he has trips planned to see friends and family in Florida, Georgia, New Mexico, and New Hampshire. He's also considering purchasing a boat to go sailing with his dog.

He also says he might even take up golf again.

Read the original article on Business Insider