Wednesday, May 12, 2021

What Might Have Been

I’ve let some very lucrative opportunities slip through my fingers over the years.  I won’t call them regrets as I’ll explain later, but I could have ended up with a lot more money than I have now.  Here I describe the top three potential paydays that got away from me.


I spent my career as a cryptographer, so it’s not too surprising that I took an interest in the workings of bitcoin when it first appeared.  I learned how it worked and appreciated the clever way it was designed to mimic mining for gold without the need for a central authority.  For a while, that’s as far as my interest went.

Later, some enthusiasts formed a group to work on mining bitcoins, and they wanted me to join.  I was tempted, but decided that I had other things to do with my time.  Given the way I tend to get obsessed with technical projects, if I had joined in those early days, I could have mined thousands of bitcoins.

When bitcoin prices were manipulated upward to spark the mania we’ve witnessed, I would have sold my bitcoins off a little at a time to avoid having too much of my net worth tied up in a volatile currency of questionable real value.  It’s possible that I could have ended up with around CDN$50 million after taxes.  But I’ll never know for certain what might have been because I didn’t join the group.

Apple Stock

I bought 3000 shares of Apple stock in October 2000.  They were only $20.54 each.  A little less than three years later, I sold them for a loss of about US$3000.  Since then, Apple shares have split 2 for 1, 7 for 1, and recently 4 for 1.  If I had held onto this stock, I’d have 168,000 shares now.  As I write this, these shares trade at $126.85, for a total of US21.3 million.

I would never have held on all the way to today without selling any shares.  To reduce risk, I would have sold small blocks of stock along the way.  My best guess is that I’d now have about CDN$10 million after tax from holding these Apple shares.  But I didn’t hold them, so I’ll never know for sure.


I had the good fortune to work for a tech company that had its initial public offering in the midst of the late 1990s tech boom.  I had no way of knowing what was about to happen, but the company’s stock price grew to 20 to 100 times any sensible valuation.  I did well with my allotment of stock options.

Leading up to the IPO, I had the chance to move into management but turned it down.  I decided I was happier doing technical work.  If I had embraced management for just a couple of years, I would have received substantially more stock options.  I could easily have ended up with a few million more dollars.  But, I chose reasonable working hours and work I liked better.


It’s tempting to look at these missed chances and draw some lessons like “when you see an opportunity, go for it” or “don’t be left with regrets,” but I think this is wrong.  None of these outcomes was foreseeable.

In the early days of bitcoin, there were believers in bitcoin as the future of transactions, but nobody was talking about getting rich from a crazy runup in bitcoin prices.  Bitcoin miners were geeks who liked the technology.  They weren’t young people seeking their fortune.

Fifteen to twenty years ago, Apple was just another small tech company that seemed sure to get crushed by the Microsoft behemoth.  Betting on Apple back then made no more sense than betting on several other tech companies.  But none of the others grew to what Apple is now.

My whole career I avoided management because I didn’t like the work, didn’t think I’d be good at it, and didn’t want to work the long hours management requires.  I had no way of knowing that enduring management for a small slice of a decades-long career would have a big payoff.

I’ve focused here on missed opportunities, but I’ve had a tremendous amount of good fortune in my life as well.  Some of the random choices I’ve made have paid off in unexpected ways.  The real lesson here is that life is unpredictable, and you’re destined to be fortunate sometimes and unfortunate other times.  There’s no point in mooning over what might have been.  Look to the future.


  1. Hi Michael, those are eye opening numbers! But as you said no one could foresee the outcome of those opportunities. For me, it is also important to know the importance of having enough. And from reading your blog post, I am sure you have enough to do all the things you want to do in life. Keep up the great blog!

    1. Hi Financial Ramen,

      Yes, you're right. By FIRE standards, my wife and I live extravagantly, but by high-tech worker standards, we live fairly modestly. We have more than enough to live the way we want.

  2. Thanks for sharing. Those are good thoughts.