How to confront the most toxic emotion in investment

It’s easy to beat yourself up about missed investment opportunities that made fortunes for those who bought in early. But it does nobody any good, says Dominic Frisby.


If only I'd invested in bitcoin way back when
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Let's say someone told you about an investment opportunity with which you could turn a small outlay a few hundred pounds, or a few hours' work into tens of millions. But you were too busy to take a proper look, or you weren't interested, or thought the idea was rubbish, and you let it pass.

It turned out to be a thousand-bagger an investment opportunity the like of which you are not likely to ever see again in your lifetime. It was an opportunity that would have seen you and your heirs in luxury for many generations to come.

How would you feel?

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Probably not far off how many are feeling now. Because one such opportunity has just passed before our eyes...

"Regrets, I've had a few, but then again" oh wait, there's bitcoin

Over the weekend I did a search in my email account for the word, "bitcoin". I wanted to see the first time it appeared in my inbox, as that would probably be the first or close to the first time I had heard of it.

It turns out it was in December 2010. A newsletter I signed up for once upon a time posted a link to an article at, of all things, PC World's website, by Keir Thomas.

I gave it a cursory read, thought it sounded like a good idea, but, so wrapped up was I in whatever else I was doing at the time, I didn't pursue it any further.

The price of bitcoin then was 23 cents. It is now something like 17,000 times higher (as I write a bitcoin is $3,925).

A £100 bet would now be worth £1.7m.

A £1,000 bet would be £17m.

A £10,000 bet £170m!

And so on.

Right there in that PC World article was the greatest investment opportunity any of us will ever see in our lifetime.

Now it would be easy to start beating myself up and, believe me, I have for not paying as much attention as I should. But it is just not possible to read, fully digest and then act upon the plethora of information that passes across our desks each day.

Within a year or so, I was a bit more up to speed, but I was heavily into gold at the time, so I never went into bitcoin as fully as I now wish I had. What's more, it kept doubling in price from $1 to $2. From $2 to $4. From $10 to $20.

I'd seen so many smallcaps double and triple, and then lose 95% of their value, that I was instinctively reluctant to chase a market that had moved so much. I think they call it, "keeping your discipline".

If only I knew then what I know now. It was still the opportunity of a lifetime, even at $100!

Indeed, one of the reasons I wrote my book on bitcoin was that I was cross with myself for not having invested as much as I should have. The book was a kind of catch-up trade.

I've used my own story here, but the world is full of such stories. Every day I get an email or a message saying, "if only I'd bought bitcoin".

And what of all those people who did see the light, took the plunge and got in early, but kept their coins with MtGox? That dreadful saga saw 900,000 coins (today's value $3.5bn) stolen in what was the greatest heist in history. How must they be feeling?

What about the people, who bought at 50c and sold at $5, thinking they were geniuses because they made ten times their money? What about the hard drives that have been lost, and the keys that have been mislaid?

A few months after that first article we're talking spring 2011 now one of my podcast listeners emailed me saying that I should check out bitcoin. At this point it was 75c. He and I happened to speak yesterday. I reminded him of that email and asked him how heavily he went in back then.

He told me a story that obliterated any regret I might be feeling. He used to mine bitcoins on his work laptop. When he left the office for the day, he would leave his computer running and mine coins overnight. He built up quite a sum.

But when he left his job, his company took back the computer and wiped the hard drive. All those coins! Gone.

And Bully's special prize a lifetime of bitter regret (and a speedboat)

Because it has gone up like nothing else, bitcoin has done it like no other market but all bull markets do it: they create regret at not having invested enough.

When you're constantly looking at prices, you're constantly reminded of the prices you could have bought or sold at. In other words, you're constantly reminded of your mistakes.

It's a bit like a never-ending re-run of the game show Bullseye, when the host, Jim Bowen, showed contestants, in the moments after they'd lost, the prizes they might have won had they played the game a little better. "Have a look at what you could have won," he used to say to the deflated players, before showing them cars, Kenyan safaris and other such goodies.

Like FOMO (fear of missing out), there ought to be some kind of acronym for this. So let's invent one. RANHIE (regret at not having invested enough) doesn't really roll off the tongue, so let's go with SWC (shoulda woulda coulda).

SWC is not a constructive emotion. It creates bitterness. It creates bores. It creates a victim mentality. As the standard sports psychology goes, "only worry about what you can affect" or, as my agent is forever telling me, "control the controllables". The only thing you can affect now is the present and the future not the past. So you've got to get over it.

But even so, humans being what we are, we continue to beat ourselves up about our mistakes.

The reality is, if I had bought £1,000 of coins at 23c, I would have sold them too soon, I would have had them stolen (indeed I did have a batch of coins stolen that's a story for another day) there are any number of mistakes I would have subsequently made.

The chances of me having held on to every single one right up the present day is extremely slim. The same goes for anyone else looking at the bitcoin price and feeling SWC. There are umpteen things that could have gone wrong, even if the original purchase was good.

So I guess there's a simple investment message to today's Money Morning. Look around you, look forward, look at the now and, yes, look at the past.

But when you do, realize that, even if you had got that bit right, it would only have opened up the door for a million other things to go wrong. Ideal SWC could never have happened. So exercise some rational self-compassion.

Do not indulge the SWC.

And, hey, were it not for SWC, I'd've never written that book!

Dominic Frisby

Dominic Frisby (“mercurially witty” – the Spectator) is, we think, the world’s only financial writer and comedian. He is the author of the popular newsletter the Flying Frisby and is MoneyWeek’s main commentator on gold, commodities, currencies and cryptocurrencies. 

His books are Daylight Robbery - How Tax Changed our Past and Will Shape our Future; Bitcoin: the Future of Money? and Life After the State - Why We Don't Need Government. 

Dominic was educated at St Paul's School, Manchester University and the Webber-Douglas Academy Of Dramatic Art. You can follow him on X @dominicfrisby