Wondering how to start investing again after losing money in the stock market?

Maybe you bought a stock you were convinced would take off. Maybe you followed someone else’s advice. Or maybe you watched your portfolio fall until you finally decided you’d had enough.

Now you’re sitting on the sidelines.

You know investing is important for building long-term wealth. But every time you think about getting back into the market, you remember what happened the last time.

What if the fear of losing money again is keeping you from becoming a better investor?

In this episode of Rich Dad Stockcast, host Del Denney sits down with Rich Dad investing expert Andy Tanner to explore why stock market losses can be so difficult to overcome—and what investors should understand before putting their money at risk again.

Andy admits something that may surprise investors who know his approach to stocks and options: He loses money on investments, too.

But he doesn’t view every losing trade the way most people do.

Why?

Andy shares an example from his own investing experience that challenges the idea that successful investing means getting every decision right.

He also explains why some investors suffer devastating losses while others learn to manage setbacks without abandoning their long-term goals.

And there’s a bigger question:

When an investor loses a substantial amount of money, is the real problem the market—or something the investor failed to recognize?

Del and Andy explore the psychological impact of losing money, the dangers of confusing basic investment knowledge with actual proficiency, and why understanding risk may matter more than finding the next winning stock.

Andy also challenges conventional advice about recovering from investment losses, including whether becoming more conservative is always the best path forward.

For anyone who has lost money in stocks, struggled with investment decisions, or hesitated to return to the market, this conversation offers a different perspective on financial education, discipline, and rebuilding confidence.

Because your last investment doesn’t have to determine your next one. But what you learn from it could change how you invest for years to come.

🎯 Visit https://bit.ly/3JsRdmj for access to FREE investing tools, including Andy’s “Power of 6” ebook.

00:00 Fear After Losses 03:07 Why Losses Hurt 07:21 Losses Are Part Game 09:05 Click And Get Paid 14:59 First Steps Comeback 16:05 Mirror Knowledge Discipline 21:53 Value Of Education 25:32 Leverage To Catch Up 29:24 Final Takeaways Next Steps