Sound Investment Insights

I Gave AI a $2 Million Financial Problem. Here’s What It Missed.I recently gave AI a hypothetical planning problem. A 58-year-old has $2 million invested, including $900,000 in one highly appreciated stock. They want to retire at 60, help their children buy homes, and...

The rise of artificial intelligence has sparked excitement among investors, but does that excitement signal an AI bubble? This article explores historical market bubbles, valuation concerns, and the risks of becoming emotionally attached to investment trends.

Why I Share Financial Ideas for Free Someone recently asked me why I keep sharing videos about charitable giving. My answer is simple: I want to help people. Most people I meet, clients and non-clients alike, want to pay the IRS exactly what they owe, and not a dime...

5 Financial Decisions to Review Before Year-End By the fourth quarter, most of the year's financial picture has come into focus. You have a better sense of your income, any gains you've realized, and what you plan to give. That makes this a good time to review a few...

I recently met with a client I've worked with for ten years. They aren't my wealthiest client, but watching their progress over that decade has been genuinely exciting, and not because of investment returns. What stands out is the accumulated effect of making one good...

Donate Your Stock. Buy It Back. Lower Your Tax Bill? If you already give to charity, consider giving appreciated stock instead of cash. Say you bought shares for $500, held them for more than a year, and they’re now worth $1,000. Selling would realize a $500 capital...

You’ve built a substantial portfolio. You understand investing, and you may even enjoy managing your own money. So why pay someone else to help? Honestly, you might not need to. But as your portfolio grows and retirement gets closer, picking investments may become the...

If you’re 70½ or older and regularly give to charity, it’s worth looking at which account you give from. A qualified charitable distribution, or QCD, lets you send money directly from your IRA to an eligible charity. Because the distribution is generally excluded from...

Donor-Advised Funds: A Smarter Way to Give? If charitable giving is already part of your life, it should also be part of your financial plan. A donor-advised fund is a charitable account that allows you to contribute cash or investments today, potentially receive a...

How 10 Years of Saving Can Beat 30 Years Ten years of saving early can be as powerful as thirty years of saving later. Consider someone who invests $500 per month from age 25 to 35 and then stops contributing completely. They would contribute $60,000. Assuming a 7%...

Before You Write That Check to Charity The same charitable gift can produce very different tax outcomes depending on what you give and when you give it. Cash has become the default for most charitable giving, but it isn't always the best asset to donate. Appreciated...

A financial planner recently shared that their family has a rule: no travel sports. The concern was understandable—they had watched families spend thousands on hotels, gas and tournaments while saving nothing for college. But I don’t believe “no travel sports” is a...

What Happens When You Get Rich Too Fast Receiving a large amount of money should make life easier—and usually it does. But whether it comes from an inheritance, selling a business, a settlement, or a professional contract, sudden wealth can create problems almost...

Most people think retiring at 55 comes down to a single number. After almost 25 years of doing this, I can tell you it doesn't. I've worked with people who could retire comfortably at 55 — and others, with even more money, who realized they weren't ready. The...

When people ask me about the biggest retirement mistake, they expect me to point to something financial — not saving enough, claiming Social Security too early, investing too aggressively. But after 25 years of helping people retire, I've noticed something surprising:...

We live in an era of unlimited financial information. CNBC, YouTube, X, podcasts, newsletters, AI—you can consume investment news around the clock. Yet despite having more information than ever, investors don't seem any less emotional. In fact, the constant flow of...

A few weeks ago I hiked the Enchantments here in Washington State — one of the most beautiful trails in the country, and one of the most punishing. Going up Aasgard Pass, you climb nearly 5,000 feet to almost 8,000 feet above sea level. More than once, I caught myself...

Why Investing Never Feels ComfortableMost people assume that good investment decisions should feel confident and clear. The reality is almost the opposite. After nearly 25 years working with investors, one of the most consistent things I've observed is that the right...