$100 a month to $37 million, Bear markets, Bogleheads and a free education

Today I’ve got a lot to share: my recent trip to Western, new educational tables from Daryl Bahls, a must-read article by Ben Carlson, a fantastic free resource called Rebel Finance, and some takeaways from the latest Bogleheads meeting.

Last week, I spent two full days at Western, meeting with students, faculty, and staff. I gave presentations to graduating seniors, a personal finance class, and the Financial Management Association Club. These students were eager to learn about building a strong financial future, and it was inspiring to see so much enthusiasm.

To get students excited, I sponsored a $1,000 drawing—no strings attached. If the winner wanted, I offered to personally help them set up a Roth IRA and invest the money for long-term growth. The goal was to show how even a single investment can grow over a lifetime.

That brings me to two new tables created by Daryl Bahls. These tables make the power of compound growth real. The first table shows what happens if you invest $1,000 at age 22 in a Roth IRA and let it grow at 8%, 10%, or 12% annually. At 8%, that $1,000 could become $30,000 after 45 years—and even more when you factor in distributions and inheritance. At 12%, the total benefit can reach over $3 million! The second table looks at saving $100 a month for 45 years. With steady returns, this strategy can result in a retirement nest egg of hundreds of thousands—even millions—of dollars, plus generational wealth for your heirs.

A key lesson: with lump sum investing, the sequence of returns doesn’t matter much. But with regular monthly investing, buying more shares when prices are low can significantly boost your long-term results. This is especially true in volatile markets like small-cap value stocks.

Of course, many people face hurdles getting started—thinking it’s too complex, not having enough money, or fearing loss. My advice is: start small, stay consistent, and use the resources available to you.

Speaking of resources, I want to highlight Rebel Finance, a free 10-week course led by Alan and Katie, a couple who retired early and now teach others how to manage money and invest. Their sessions are interactive, practical, and archived on YouTube. If you—or someone you know—needs a supportive, step-by-step introduction to personal finance, Rebel Finance is a fantastic place to start.

I want to highlight the Merriman Financial Literacy Program at Western. This initiative is close to my heart and is designed to give every student—regardless of their background—the tools and knowledge they need to make smart financial decisions for life. Thanks to the program, all graduating students at Western receive free access to iGrad, a comprehensive suite of financial education tools and courses.

I also want to mention Ben Carlson’s article, “On the Inevitability of Bear Markets.” Carlson shows that bear markets are unavoidable—there’s a 77% chance you’ll experience one in any 5-year period, and a 95% chance over 10 years. But the longer you stay invested, the greater your odds for positive returns. Historically, holding the S&P 500 for 20 years has always resulted in gains.

Finally, I had the pleasure of attending a Bogleheads local chapter dinner. It was inspiring to meet others interested in index investing and financial education. We shared ideas, discussed financial planning tools, and talked about helping our families build wealth. I’ll also be speaking at the Bogleheads Conference in October—check the show notes for details.

Before I sign off, a quick note: AI is changing how we learn and teach about investing. I’m using it to organize my thoughts and create better presentations. If you have thoughts or experiences using AI in your financial journey, I’d love to hear from you.

Thank you for listening! If you found today’s episode helpful, please like, subscribe, and share it with someone who could benefit. Your support helps us reach more people and make a bigger impact. Good fortune, and happy investing!