Twelve years ago I was absolutely obsessed with Tesla. The stock was pretty volatile, but trading in the $20 range for a while. So I took $5000 out of my wedding fund, bought the stock and watched as it took off like a rocket ship for years to come. Today that investment is worth $526,201.
This is what I would have said if I’d done what I wanted and looted a portion of my wedding fund to invest in Tesla back in 2012. Of course this is assuming I didn’t sell when I was up 100%, 200%, 500% (which I would have) or that my soon to be wife didn’t throw my body in a river.
We’ve all heard the stories. Maybe you’ve been the star of a story. Someone puts a relatively small stake in a longshot company and makes a killing. I actually happen to know the one guy who legitimately paid off his house and cars with Bitcoin. There’s a place for this in your portfolio for sure, but it should make up maybe 1-2%. For me, the majority of my moonshot investments have been more moonshit. Time will tell, but I don’t see Hylion recovering from a 97% loss. At least there’s good news, a stock could lose 97% every day indefinitely.
I am a big believer in index and mutual fund investing. It has served me incredibly well the past fifteen or so years and kept me from making a lot of stupid mistakes. When I get the urge to get more granular and start picking stocks, more often than not I look to see if there is an industry index I can buy instead. For example, in 2020 airline stocks absolutely cratered when nobody could, or wanted to fly. I decided to put a significant investment into airlines, but instead of focusing on individual stocks I instead bought the JETS index fund. While JETS has returned over 80% since then, it’s not quite the return of individual airline stocks in the same time period. Yes, I could have thrown all my money into United Airlines, but in buying the index (which is heavily weighted towards United and Delta) I spread my risk around and still got a significant return.
Whether it has been stocks, funds, or crypto I’ve had both good and bad outcomes. However they all pale in comparison to the single greatest stock trade I ever made.
Nine years ago I was working at the best job I’d ever had. I had a great team, a great boss, great pay and even a decent commute. I was a very happy guy. There was a dark side, though. Our company stock was crap. It had been crap for over a decade. The long term employees I worked with had options packages from the good old days when the stock wasn’t crap and they couldn’t even sell them without losing money. Getting equity in a crappy stock is fine if you’re going to sell it, but it’s not very motivating. And living in fear that the crappy stock would go down a few points and cause layoffs just sucked.
So despite my contentment with my job, I set out to find a new company to work at. After submitting applications with big name companies that I was working with, I decided to try my network. As it happened, a friend was on a team in search of someone like me and I could interview right away. Maybe you see where I’m going with this.
Below is the stock chart of the company I currently work at. I’ve been here for the eight years pictured, and I’ve gotten equity and leveraged our ESPP the entire time.
My company stock has increased 12x in the time I’ve been here, and continues to rise. What’s more, this time I didn’t invest $5k, or $50k…I went all in. I made it my job, and I made my job a huge part of my life. My pay is 4-5x what it was at my previous company, mostly thanks to the equity in this company. Working at my last job gave me a great opportunity to get into the software industry and to pay off my debts. Working where I am today made me wealthy.
A few years back my old company was bought out and my former coworkers received a nominal fee for any outstanding shares and options, but nothing life changing. In that time I’ve had life changing moments multiple times a year in the form of large windfalls and career opportunities. I’m grateful for my time and experiences at both companies, but trading one for the other was the single greatest stock trade I’ve ever made in my life.
Freed by 50 