top of page

Sign up for our mailing list

Thanks for signing up!

  • Timothy Iseler

The Worst Trade I Ever Made

(FYI - I wrote this post in early 2020. All the numbers are out of date, but the concepts are still valid. Thanks!)

Everyone makes bad investment choices now and then. It just happens, even when the reasoning is sound. Sometimes a purchase is made right before a disappointing earnings report that sends the price plummeting. Other times the information used to select an investment turns out to be incomplete or misinterpreted.

Likewise, everyone occasionally falls into the trap of thinking that he or she is smarter, better, or more clever than other investors. Other investors make simple mistakes like selling too early, overestimating risk tolerance, or not properly assessing the finances of a certain business, but never me! If only it were true.

In late 2017, a friend of mine told me about an app that would automagically round up transactions and use the difference to buy cryptocurrency. Bitcoin was in the middle of a crazy run and, like a lot of people, I thought ‘why not’.

Feeling like I didn’t want to miss out on the opportunity and flush with cash, I decided to invest close to $1000 in the number two cryptocurrency player at the time, Ethereum (ETH). My reasoning was that Bitcoin was already over-bought, but the number two player still had room to run.

Of course, the market for cryptocurrency peaked within a month of my purchase and then fell off a cliff. It has not recovered as of the publish date of this article. My initial 17 Dec 2017 investment of $985.32 in ETH stands at about $359.77 for a total return of -$625.55 or -63.5%. Woof.

That, however, is not the worst trading mistake I have made. Looking back a little further, on 09 Jun 2016 I bought 1 share of Chipotle Mexican Grill (CMG) for $423.81. The price dipped shortly after that because of a new food poisoning scare (they couldn’t get enough of that in 2015-16) and I bought another share on 14 Jun 2016 for $395.17. Buy while it’s cheap, was my thinking. I then owned 2 shares with total cost of $818.98.

The rest of 2016 wasn’t spectacular for Chipotle, and neither was 2017. By 23 Mar 2018 I decided to cash out my 2 shares of CMG, selling for $679.46. That represented a return of -$139.52 or -17%.

However, since then CMG has gone on to set new all-time highs and recently closed at $921.94 per share. The two shares that I sold for a loss of $139.52 would now be worth $1,843.88, a difference of $1,983.40.

My biggest trading mistake was not in choosing an investment that would lose 63% of its value. It was walking away from a position that was down, but would eventually return over 225%.

My error was one of the most common, and the most costly: selling a long-term winner out of fear in order to cap short term loss.

If you are considering investing and have a potential holding period of 10+ years, try not to pay attention too closely to what happens day to day, quarter to quarter, or even year to year. Instead, at the time of purchase write down exactly why you think you are making a good decision and how long you believe your thesis will remain solid.

Review that statement as you watch the price bounce up and down. If the original thesis holds, hold your investment through thick and thin. If new information or a change in the business makes your original thesis invalid, consider selling.

Timothy Iseler, CFP®

Founder & Lead Advisor

Iseler Financial, LLC | Durham NC | (919) 666-7604

Iseler Financial helps creative professionals remove stress while taking control of their financial futures. As both advisor and accountability partner, we help identify current strengths and weaknesses, clarify and refine your long-term goals, and prioritize understandable, manageable, and repeatable actions to bring long-term financial well-being. Reach out today to take the first step.

104 views0 comments

Recent Posts

See All


bottom of page