Dave Ramsey says he never bought single stocks

In a recent conversation with Theo Von, Dave Ramsey shared his unfiltered opinions on real estate and investments. Ramsey was blunt, saying, "I hear this stuff on social media that real estate's passive income – bull crap. There's nothing passive about it, dude. You're either involved or getting screwed. One of the two."

Theo Von also chimed in with his own real estate issues, mentioning unexpected problems like Airbnb complaints and incidents like someone starting a fire because they didn't want to use their unit’s heat. "Just crazy people doing fires. Stuff like that," Von said.

Ramsey agreed, noting the many hassles that come with real estate. He contrasted this with T-bills, which he described as much less stressful. "You buy it, forget it, and they send you a check. It’s not as big a check, but there’s no hassle," he explained. While mutual funds carry more risk, they're still less stressful than real estate and can yield higher returns.

Von mentioned the stress of constantly checking stocks, which he found counterproductive: "I'll check them too much, and I don't like it, and then it's like I spent 30 minutes of my day checking stocks, and that's time I could have just had him doing my work."

Ramsey responded that he buys mutual funds and forgets about them, focusing on long-term gains. "I don't even know what the market has done this year, and I do this for a living. I don't keep up with it," he said.

For Ramsey, investing is all about the long-term perspective. "You know, look at what the stock market has done since 1980, since 1990, since 2012. Look at what I would have made if I’d have put in $10,000. Since 1992, $1,000 would have turned into $5,000," Ramsey explained to Von.

When Von asked if Ramsey ever regretted selling a stock too soon, Ramsey admitted he never bought a single stock. "The only dumb thing I did was buy gold once," he confessed. He lost $5,000 on a risky options bet that didn't pay off.

He called it "uber high-risk" and likened it to gambling: "This buddy of mine was making money, and he had this gold guy that we could buy gold options. We didn't even buy the gold. You're just buying the right to buy the gold, and he said he put in 5,000 bucks, and if it goes up, the option goes from $5,000 to $50,000, and I'm going to 10x my money. This guy had hit 14 times in a row, and he said, 'OK, we need to go in right now and put $5,000.' Unfortunately, after Ramsey invested his $5,000, the person didn't predict how it would go for the 15th time. 'It's all or nothing, so I lost the whole $5,000 and no sign of $50,000, right? So I'm done,' said Ramsey.

Von then shared his experiences with pyramid schemes, recalling a childhood scam and a failed investment in glitter mining. Ramsey added a humorous anecdote about the 1980s emu farming craze, which he managed to avoid, laughing about the absurdity of it all.

"I remember in the 80s, everybody decided that emus would be the new meat, and many people decided they would sell everything and open an emu farm. I managed to stay out of that scam. That was one of those fad things that didn’t work," Ramsey described.