A Story About Investing — And Lessons Learned

A while ago, I encouraged my son Josh to open his own retirement account. (He’s the one wearing the top hat in our family cruise photo.) To make it fun, I pitched the idea as a friendly contest: we each put about $1,000 into a Roth IRA. My goal was simple — to show him what’s possible, even starting with a small amount.

Josh had spent years watching me teach option trading, so he knew I was serious about investing. I explained that the earlier you start, the more aggressive you can afford to be, because time is on your side. 

Unfortunately, Josh made a small mistake on his very first trade — the kind of mistake every trader has made at least once. He accidentally entered more contracts than he intended.

I suggested he close the extra contracts right away. But like many investors, he hesitated, hoping the trade would “come back.” It didn’t. The position moved against him and the loss stung even more. We both lost money on that same trade, but my loss was not as painful because I was not overleveraged.

I share this story not to embarrass my son, but because it highlights a truth all investors face: mistakes happen, and sometimes they discourage us from moving forward. Josh grew frustrated and stopped trading. His account is still earning interest, but he’s still sitting on the sidelines.

Meanwhile, I continued trading my own “demonstration” account to show him what’s possible. Over about 18 months, as shown in my statements below, I grew that account by 766% without adding any cash to the account. In fact, if you look at the statement from February 2025, you'll see I pulled some money out to start another small "demonstration" account. Otherwise, my returns would show even better. During the same period, the S&P 500 rose about 30% — a solid gain, but one that came with sharp drawdowns due to geopolitical and economic uncertainty.

Here’s the point: by using derivatives strategically, I was able to turn uncertainty into opportunity and achieve far higher returns in that small account. Now, this was a high-risk, aggressive portfolio designed to prove a point — not how I manage long-term retirement funds. But it illustrates what’s possible with the right strategies.

The reality is, even a traditional index fund carries risk. During the 2008 financial crisis, many investors saw their portfolios cut in half. In March 2020, during the COVID shock, many lost a third of their wealth in a matter of weeks. The good news is, those kinds of losses aren’t inevitable. With smart use of derivatives, it’s possible to hedge portfolios, cushion the downside, and even add to positions so you recover faster when markets rebound.

Every investment involves risk — that will never change. But with nearly three decades of experience in derivatives and risk management, my mission is to help clients reduce exposure while still participating in market gains. If you’re looking for ways to protect your wealth and grow it more intelligently, I’d be honored to show you how.

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About the Author Bryan Strain


Bryan is a Senior Investment at Hurley Investments. He has been involved in the investing industry for over 30 years. He's an expert in using options and loves to help retail investors compete with elite professionals.

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