Turning Dollars into Dimes: Time-Tested Options Strategies for Losing Money

1 min read

Creating great options strategies is a process of trial and error. This article is about those errors. Bad Strategy #1 — Selling Naked Options: The pinnacle of recklessness. This graph shows that if the market goes up, the trade stands to make a little bit of money. If it goes down, the trade will lose a lot of money. Selling naked puts OR calls (or tail-risk for you fancy folks) never ends well. Having a limited upside with unlimited risk is the antithesis of good trading. Here is a short list of professional traders who have cumulatively lost almost $3 billion with…...

This article is free to read

Login to read the full article


By subscribing to our main site, you will also be subscribed to DDIntel - our regular letter showcasing our featured articles and applications.

Tyler Michalove Tyler Michalove is the Head of Trade Systems and Execution at Blackpier Capital. In this role, he designs, tests, and executes managed options strategies. Blackpier Capital provides managed options strategies for high net worth individuals, family offices, hedge funds, and institutions. Previously, Tyler helped design volatility models for a large investment manager and conduct equity research. He also has taught students at the University of Tennessee about options trading and led lectures on how to use Bloomberg software. Tyler has created fractal volatility models, designed and built trading software, written volatility white papers, and has helped grow Blackpier Capital from a start-up hedge fund into a predominant managed options fund.