Gunslinging Gambler or Cautious Investor: Which One Are You?

On this week's Stansberry Investor Hour, Dan and Corey welcome Herb Greenberg back to the show. Herb started out as a financial journalist and now publishes On the Street, a newsletter that offers observations, insights, and opinions on various stocks and the broad market. Herb has spent 50 years researching and writing about the markets, and he joins the podcast to impart some of his wisdom.

Herb starts off by reintroducing himself, his opinions on market risk, and his history with long-biased research. He emphasizes that knowing yourself, your psychological makeup, and your skill set are crucial components to success. Some investors thrive under the pressure and enjoy the gambling nature of stocks, while others prefer to sleep well at night and take a more cautious, long-term approach. Either route is OK. And the same principle applies to specifics like when to sell a stock... "There's no one size fits all," Herb says. But the upside to every mistake is that you'll quickly learn more about yourself. (1:22)

Next, Herb discusses a recent post in his On the Street newsletter about home-furnishings company RH. Not long ago, RH's CEO made comments concerning debt that raised many red flags. This leads to a conversation about software company MicroStrategy, which has been using debt to buy bitcoin. "It's a pyramid atop a pyramid," Herb quips. He also shares his thoughts on bitcoin itself, talks about the 2021 market mania where "everyone was a bag holder," and dives into how retail and institutional investors differ in risk versus reward. (19:27)

Finally, Herb evaluates today's market optimism and the potential for an inflection point. He notes that many garbage stocks have gone from deep in the red to in the green this year for no reason other than hype. Herb then urges investors not to get complacent with their portfolio holdings and to always consider differing opinions on stocks, in case the setup has changed since you first bought in. "You lose sight of the ones that have not been problem children." Herb rounds things out with a discussion about short selling and market inefficiencies created by passive investing. (38:29)