Lost Money in Stocks? Andy Tanner Explains How to Start Investing Again

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 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 of the 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
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Disclaimer: The information provided in this video is for educational and informational purposes only. It should not be considered as financial advice or a recommendation to buy or sell any financial instrument or engage in any financial activity.

The content presented here is based on the speaker's personal opinions and research, which may not always be accurate or up-to-date. Financial markets and investments carry inherent risks, and individuals should conduct their own research and seek professional advice before making any financial decisions.

Cameron Long

Cameron is a seasoned CFO and CPA with 31 years in finance. He created the AI Trader's Playbook to help everyday investors use AI to find high-confidence trades — in minutes, not hours.

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