I‘m actually thinking about selling my wallet and buying a 2x leveraged BTC ETF lol.
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OK. I studied maths and specialized in cryptography. I read the Satoshi paper a few days after it was released on the internet.
I also did a mental model of the potential price of bitcoin based on it being an alternative store of value to gold and came to a 6 figure number, bear in mind this was in the early days when you could mine BTC on a CPU and nobody outside a few crypto nerds knew about it.
I thought it was very interesting and wrote about it on various online forums (later when the price ran up to $100, some complained to me that I didn’t sell it enough and now they ‘missed the boat’ - LOL).
So how many billions did I make by:
- having the maths to understand what BTC was
- having the financial knowledge to be able to model a price in 6 figure
- having the technological know-how to easily deploy a miner and mine BTC? (a few years later I also bought a GPU for the purposes of password cracking, which could also have been deployed for BTC mining once GPU miners were invented)
Absolutely nothing!
- I was not really interested in money/finance then (even though I worked in Finance). I was just a 20-something just interested in going out and getting drunk at the weekends
- The brain has an amazing way of forcing inertia. Maybe it is an evolutionary thing to stop you from wasting energy. But I came up with all sorts of internal arguments to avoid doing something (‘but the government will shut it down if it gets too popular’ etc.)
Fortunes are made when opportunity meets preparedness and action is taken.
I almost had all components here but I was not mentally prepared and didn’t take the necessary action.
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I may have written this before here somewhere, but when I was finishing my PhD (2009) I went through a 5-day entrepreneurship workshop which culminated with a day where we met people who’d made it, and some hopefuls. Among the hopefuls were a bunch of guys from Finland talking about a game for mobile phones they’d made, I remember thinking “What kind of idiot wants to play games on the phone?”. Funnily enough as a gamer since the early 90s I still think that. Edit: forgot to mention the game was Angry Birds.
In the same workshop were some guys talking in the corner about something called bit-coin, and they were offering to sign up to something and get a few hundred of these bit-coins to play with. I didn’t understand what that is so declined. In reality, I know full well that even if I’d taken these “few hundred bit-coins” I’d most likely had lost access, or would have sold the second I could, as even £300 at the time was a big deal for me as a student. Phil wrote a nice “What if” scenario in another thread showing that the vast vast majority of people would have sold many years before it was costed any serious money. I also remember a nerdy guy (edit: like me and most my friends, though we don’t look it!) we used to play AD&D with, at some point he told me he was doing something with his PC at home, solving equations and getting rewards for it. He never said “btc mining” so I’ve wondered, however at some point he dropped off the face of the earth which makes me think he might have made it big and decided to disappear.
It’s not regrets, my regrets are documented above, I am just writing because it’s a day of hell starting at work, off the back of a month of hell with 2 travels to the UK in 3 weeks and I want to delay it somewhat.
P.S. the entrepreneurship workshop managed to show me I do not want, or have the character to be an entrepreneur.
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I sold 30k worth of physical gold end of 2025 to optimize tax through a Pillar 2 contribution, thinking I could buy it back same price or cheaper later 
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I regret not having lived to my actual holding mantra: “hold as long as possible… but not longer”.
I have tons of examples where I missed millions just for selling too early. And a few later where I lost a lot holding too long.
The example that still flows around my head is priceline. Started by Hutchinson Whampoa it was a kind of eBay for travelling. Then it became booking.com. I made a few hundred percent that today would be a few ten-thousand (was around the year 2000). My position would have raised to 5-10 million USD I think… that is enough to make you regret.
On the other hand I hold mergers way too long. Almost all mergers go lala, the new company is worth way less than the two old companies after a few years. The best would be to sell as soon as you can.
One example is Lumen, ex Century link. The company was once a wedding gift and did grow a lot, but at the end it was all bought growth. The merger with Level 3 broke it’s neck. It lost like 99%. I still had a rule in my divi strategy to hold 2 years after a sell signal, what an idiotic rule. The rule was born because of priceline. Did cost me a lot.
But then, you can only lose 100% but gain 50’000% like I would have with priceline.
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I feel pretty much the same way, but it was for the sale of a shitcoin that had doubled my initial investment. Maybe next time!
Another major miss was when I was investing in AMD. It was a massive turnaround and it was not priced in.
I’d already bought a lot of shares but was looking to benefit more from it, so turned to options. I found options available but it looked too good to be true. Call options costing just $0.02 with a low strike price.
My finger was hovering over the buy button but, at this point time, I’d never used options before so was very unsure and thought “if it looks too good to be true, I must be missing something” or “don’t invest in what you don’t understand” (what did I say about the brain talking you into inaction).
So I didn’t buy them. I later calculated that had I invested, it would have made me $20 million in the space of 3 months. 
Needless to say, after that, I started trading options just to build up fluency in it to be ready for next time.
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At some point I need to ask chatGPT to explain how could this be done: Bank denies allegations it gave bad advice to Tesla investor who lost $415M | CBC News
Edit: specifically how did the guy turned 88k to 26mn with options in 6 months (that’s 300x), then on to 415mn - that’s roughly 4700x in total.
I cannot fathom why anyone who gets to 86m, let alone 400m doesn’t set aside some of it.
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From my crypto friends “because when you get to a point that every 1% up means you can buy a new car…it becomes addictive”.
From me pretending to know what I’d do in this situation “because they have no investment plan in place”!
NB only one of my friends who is/has been in crypto actually got there, and he did have an investment plan in place.
The thing is, with 86m, even investing at 2.5% gives you 180k to spend per month! I don’t think I could even bring myself to spend 180k per month.
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It was only 26mn at first, a paltry sum. Only 54k per month.
Edit: effing idiot, really, they could be set for life, them, their kids, their grandkids, and their grand grand kids but no.
More detail here, as WSB put it “88k to 415mn to zero, a true hero among men (of degenerate gamblers”.
Closer to home, Phil, and on topic of regrets, I’m sure you’re also aware of this marvellous piece of work: Lottery winner Michael Carroll who blew £10m - but has no regrets - The Mirror
I regret not spending the time to educate myself about the stock market early in my life.
It would be less boring to say that I regret not participating in Bitcoin mining with my friends when I was a student and the price was something like 0.1 usd. We had access to several school computer labs and many friends used them for mining.
But there is no actual regret. I didn’t understand it then, I do not understand it now. It is as if I am regretting not choosing the winning lottery ticket before the lottery.
Btw none of my friends got rich. All of them sold their hundreds/thousands(?) of bitcoins quite early. e.g. for buying a new card, computer upgrades etc.
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Eh you’re Greek, like me, we grew up with the narrative of people who lost everything etc. Having heard the Bogle message in eg 2012 would have made such a difference today, but oh well, our kids will!
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Not sure of the details about how 26m was reached but I presume there was a run up in the value. So any “reasonable” person would have sold way before 26m… which i suppose is the point. Anyone who would act reasonably would never make such an absurdly concentrated bet and avoid diversifying out way earlier.
(See all the comments above of people who sold BTC or Nvidia or whatever after a few % gain years ago)
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+1 here.
Even worse, having went through the trouble of transferring money between exchanges to manage buying this one exotic altcoin that was supposed to moon soon, and in the process convert through multiple currencies that would have actually gone to the moon. 
On the other hand that regret feels like someone regrets not having put their money on red instead of black in roulette after seeing the outcome.
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I should have just bought a stock ETF