I Got Lucky in the Market. Then I Got Smart.

If you ended up on this blog post, chances are that you’re one of the few people still interested in the story behind a project — and Ctrl-Trade has an interesting one!

Even after coding up my own trading software and making options a daily habit, I still consider myself more of a software developer than an options trader. And like many others, and probably like you, when I moved my first steps in investing I thought I could pick the winning stocks and time the market.

The problem was that I got lucky! As a software developer I naturally started investing in tech companies (invest in what you know!), based on my own assumptions:

• Cloudflare is “under-understood” and is far more valuable than people think — I invested in its IPO
• Shopify is the best ecommerce software on the planet, it MUST explode
• Twilio makes transactional marketing so easy, it’s a winner

And so on… a few other names that actually worked well for me, also thanks to Covid-19 moving our lives online. But this luck had another side of the coin — it was creating a strong bias that I could predict cause and effect in the market, which nobody can.

Now, 5 years later and about 20 financial books later, I laugh at myself for even thinking I could do that. And so:

• Early 2022: Shopify crashed and its value went back to mid-2020 levels
• Mid 2022: Cloudflare crashed and its value went back to late 2020

Twilio and many others had the same fate, which was pretty obvious in hindsight — they are highly correlated assets! I didn’t lose money, mostly thanks to being early in Cloudflare, but the gains were strongly underperforming the market. Something didn’t add up.

In the following years I started building my financial knowledge (not completely from scratch — my dad used to work in a bank), and began diving into the stories of Peter Lynch, John Bogle, Benjamin Graham and other legends of finance.

I transitioned to a “just buy a well-diversified ETF” approach, which worked well for a couple of years. Money was growing steadily, but not the excitement. Never one to stop exploring, I decided to put my nose into options. My first book was “A Simple Guide to Selling Options” by Kevin Smith, which I consider my mentor — I owe my passion for options to that book.

The concept that got me hooked is that, as an option seller, you naturally have a statistical edge in the market. That gave me the confidence to get started, place the first trade, and eventually build my own trading software — one that does everything I believe a good trading tool should do:

• Helps me find good trade opportunities using a statistically valid edge
• Keeps my trading journal organised
• Gives me clarity on my portfolio: how much is invested, how diversified it is
• Helps me read current market conditions and volatility levels
• Tells me how healthy my positions are, when to roll a contract, and how to repair a bad trade (which will happen at some point)

It started as my personal trading assistant. Then I took the courage to make it public — well, actually in private beta at the moment :)

I was struggling to find a name, as I always do with new projects. Then I looked at my keyboard and noticed that the option key is right next to the “ctrl” key. And there it was: Ctrl-Trade!

Not sure if it’s the best name — maybe it’s “too nerdy” — but at least it reflects my journey and it’s authentic.

Thanks for reading and happy investing,

Francesco