Welcome to the underwearmillionaire.com site. This site is dedicated to sharing my swing-trading story and tactics which allowed me to retire at 54 from a career in Information Technology, (I.T.). The underwear millionaire name originated from my wife laughing at me as I worked my I.T. job from home and trading most of the day in my underwear and a bluetooth headset. (Black boxer-briefs for those who want the disturbing visual or are curious.) The purpose of this site is to share my story, my journey, and my strategies to hopefully prevent others from making my numerous trading mistakes!

One of my first memorable stock trades was in the late 1980s. From a pay phone (yes, a pay phone) at Montgomery College, Rockville, Maryland, I called my broker to purchase a gold mining stock. My analysis said the market was going down and I wanted to buy something defensive. On Monday, October 19th, 1987, I made this purchase. This day was the largest single-day drop in stock market history – 26%! Needless to say my analysis was right and I still lost big! My first clue should have been the 25-minute wait to speak to a broker. I have made countless mistakes: holding to long, riding a stock down 60%, buying to large, buying in down-market, lack of any risk-control, round-tripping, over-leveraged, the list goes on. I have made more mistakes than I can count or remember. However, after 25-plus years of trading, reading hundreds of books, attending all the seminars, and learning some seriously expensive lessons, I have developed my own winning set of swing-trading strategies that match my personality. I openly share these strategies and ideas on this site. After some monster winning trades I retired in July 2021 from my full-time job. I know spend more time with the family, travel, play, trade, and work on this blog site. 

I hope you enjoy the content on this site and learn from my mistakes. Better yet, I hope you have some profitable/winning trades and retire early as well! If you would like to reach out, please contact me at: david@underwearmillionaire.com