How and Why I Became a Trading Mentor

How and Why I Became a Trading Mentor

Posted On September 3, 2021 2:17 pm

As the old saying goes, “those that can’t do, teach.”   While I’m sure this has been an irritant to teachers ever since George Bernard Shaw coined the 1903 phrase, it certainly has some validity; especially in the investing/trading world.  As your Twitter feed and email inbox gets filled with advice and seminar offers for newsletters and trading systems, it’s completely understandable to ask, “If these people are such successful traders, why do they need my money?”

So, why do I run the Options360 trading service, write this column, and host the Options Academy? 

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Simply put, it’s a labor of love. 

As a trader and person, my origin-to-growth story boils down to three components; practicality, selfishness, and altruism. 

The practical element came about in 2001 when I got married.  As I’ve written, I basically grew up in the business, becoming a Chicago Board of Options Exchange (CBOE) member at the tender age of 22 — already had been trading for over a decade.  During that period, I had several years where I made more money than I deserved. However, I also had two occasions where I blew up my account, which I also didn’t deserve; damn you naked option selling! 

The timing of my marriage coincided with a shift from physical trading floors to electronic trading, the explosion of financial websites, and the impending birth of my first child.  From a practical standpoint, it would no longer be responsible for me to have my family’s well-being solely dependent on the volatility of my trading. 

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I got a call from an old college friend who had become an editor at TheStreet.com asking: “You were an English major, right? And still trade options? Want to write a column for us?”  Yes, yes, and yes.  And I loved it.  My role quickly expanded to working directly with Jim Cramer and launching an options-based newsletter.  I continued trading for my own account. But, I now had a predictable and reliable paycheck. The pressure of needing to “pan for gold” every day the opening bell rang was lifted.  I was now an upstanding citizen with a real job.  

This leads to the selfish part: I found my writing about the markets, and providing trade recommendations was helping my own trading.  It forced a discipline on me in terms of research and a shift to a more managed risk approach to trading. There was no more mere wandering onto the floor, or flicking on my screen — seeing what was moving and flinging some options around.  Defining my risk/reward, harnessing time decay, and using spreads became the bread and butter of my trading strategies. 

Which ultimately leads to the altruistic element of my current career choice.  I used to be fairly cynical about trading with little redeeming social value, even as I was making good money; I can live and continue to support my family on my own trading.  But I saw all the misinformation, intimidation and downright lack of true education in the world of finance and trading advice, especially with regard to options. I am now a proselytizer for options.  I want people to use options the right way, allowing them to take control of their own financial well-being so they aren’t dependent on a job they may not love. 

I’m lucky, I get to labor at what I love.  Here’s hoping everyone has a great labor-less Labor day. 

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About author

Steve Smith

Steve Smith have been involved in all facets of the investment industry in a variety of roles ranging from speculator, educator, manager and advisor. This has taken him from the trading floors of Chicago to hedge funds on Wall Street to the world online. From 1987 to 1996, he served as a market maker at the Chicago Board of Options Exchange (CBOE) and Chicago Board of Trade (CBOT). From 1997 to 2007, he was a Senior Columnist and Managing Editor for TheStreet.com, handling their Option Alert and Short Report newsletters. The Option Alert was awarded the MIN “best business newsletter” in 2006. From 2009 to 2013, Smith was a Senior Columnist and Managing Editor for Minyanville’s OptionSmith newsletter, as well as a Risk Manager Consultant for New Vernon Capital LLC. Smith acted as an advisor to build models and option strategies to reduce portfolio exposure and enhance returns for the four main funds. Since 2015, he has worked for Adam Mesh Trading Group. There, he has managed Options360 and Earning 360, been co-leader of Option Academy, and contributed to The Option Specialist website.