In 2017, first took a very small position only because it appeared that Fairfax's insurance business had improved significantly, and the stock simply looked very cheap. They had also mostly stopped the shorts/hedges which had held them back for years.
In 2020, became far more interested in the company (beyond just a "cheap stock") after reading some very convincing posts here on COBF (much thanks to Viking and others). When Prem announced his purchase of ~$150 million worth of shares in 2020, I said "game on" and I decided to swing big myself. Bought my largest chunks of shares around $280 - 320 (US).
((I also had concerns that the huge amounts of Covid stimulus $ being pumped into the economy would eventually lead to higher inflation and higher interest rates, and FFH felt like a safe way to invest in something that would potentially benefit from higher rates. In hindsight, this was probably a silly "macro bet" mentality which would have been difficult to defend at the time. But there were plenty of other good reasons to invest!))
2022 was particularly stressful, as my employer (at the time) was in the process of shutting down my plant (chemical plant operations mgr). Oddly enough, it turned out to be a wonderful problem, because after I left this job I had the option to "rollover" my old 401k into an IRA which gave me the opportunity to buy additional FFH shares with funds that had previously been restricted mostly to index funds. I was following this very board closely (mostly lurking and reading, rarely posting since I didn't feel I had much to contribute) and had been amazed the stock price had not increased much. Bought another large chunk at ~$460.
Folks will call me crazy for doing this, but over the past 5 years my Fairfax investment has ranged between 60% - 90% of my net worth. Currently trying hard to re-diversify and get it back down below 50%, but I struggle to find investments where I have the same level of conviction. Slowly but surely I am diversifying, although I have a fair amount in my taxable account which I will probably never sell.
It has been a life-changing investment for me and my family, and I can't say enough to thank people here.
Cheers,
Kevin