But it made me wonder, if you polled everyone on this board, what is the one stock or asset that has made them each the most money over time? I.e. trading in/out of US banks, or BRK, Fairfax, etc. etc.
Of course, there are some situations like Eric where you make a craptastic ton of cash on a single event which will probably never reoccur. But over a lifetime, most I feel will make it trading in/out of stocks they "know". So why not go even further: just study one business/stock - for your entire life? I mean, if you become the de-facto expert, and you trade that stock with a value mindset (margin of safety, general conservatism, etc.) I think you would do pretty damn well. Just food for thought.
OT?
I think the absolute amount "most money" has drawbacks. As portfolio grows, the latest stocks will make most money. Also slow grower kept forever may make more money than fast grower kept for 1 year, but fast grower has way bigger return rate. OTOH trying to figure out best-return stocks by adjusting for portfolio size and return rate is a bit complicated (so I will never do it), so perhaps your measure is not that bad.

So I looked at my portfolio since the beginning of the universe (TM). I cannot account for all Liberty-Malone machinations, so I skip Liberties. I'm pretty sure they would be in the list though (some of them in positive, some of them perhaps in negative). My "most money" stocks then are: BRK (6 Jur-units money made), JPM (5), Gulfport Energy (4), ING pref(3), Exor (3), AAPL (3), Grand Terra Energy (3), First Industrial Realty Pref (3), Fairfax (3).
I think these cover a lot of what you said and also cover the issue I raised with your measure:
- Gulfport Energy (4), ING pref(3), Grand Terra Energy (3), First Industrial Realty Pref (3) were great returners from 2008-2009 GFC. So, once-in-a-lifetime event perhaps. Especially since my biggest losers (also since forever) include energy stocks in 2014-2016: about -2 Swift energy, -2 Denbury, -1 Baseline Oil.
- BRK (6), JPM (5), Exor (3), AAPL (3), Fairfax (3) are all "recent" stocks, which accounts for their bigger contributions than let's say pre-2009 holdings.
- AAPL annualized return is higher than BRK annualized return
Regarding your suggestion, I don't think I traded in/out of any of these stocks. I either bought and sold or bought and held. I don't think I'm gonna trade in/out of them in the future either.
