Union Pacific even though it has some cyclical down times, has historically been an excellent investment and likely will continue to be so, IIRC it has returned somewhere around 16% the last 15 years or so, not bad at all (thats top of the head from a recent article i've read so...). Whether or not Apollyon knew this prior, that it has returned wealth to shareholders greatly over time and consistently done well. Given the 6 billion dollars CAPEX that buffet is putting into this year and its near monopoly on the US, and as long as oil keeps going by train...its likely going to continue doing well. Maybe he didnt have more than a 1000 to put down. You do well when you recognize a great opportunity, and then have the courage to go in heavily, which is not at all easy even when you can recognize the opportunity....like now say investing in greek/russian indexes for the long haul as they are extremely down, though russia isnt down enough quite yet. That is a fairly low risk (due to low price and no where to really go, unless you think the countries are going to break up) and long term will net good returns on invested monies. However, it may be a long time.
I dont get the "stockpicking" tussle, the only thing about his purchase that makes it not totally amazing is the principal, 2.5x times original investment is great in 4 years no matter where its at, index , real estate or otherwise. Only the principal determines if youre intellectually satisfied or set for life. You dont even have to inherently smart to do well, just think this iphone is cool and want to buy in at 5$/share, bam, youre done no work necessary. The first part about investing we should learn is to lose as little money as possible, this just digs a hole thats awful hard to get out of.
Indexing is great, but after 10-13 stocks that arent super correlated you basically have an index. Anything over 20 and it will behave similar to the s/p all else being equal. They dont even all have to do well, only a couple have to do so while a couple can fail and the rest just be mediocre. Thats investing, even a broken clock is right twice a day.
Heck, you can easily outperform the market using a basic paired switch momentum style between only two mutual funds/etfs, etfs are better for logistical and cost reasons. Even Fama knows this, and calls it...the "anomaly". This takes no more than 30s a month and you dont have to know whats in the funds, their earnings, or really anything other than whats the buy that month and you will trounce "the market", and with less volatility and maximum draw down to boot. Its not as satisfying as winning because youre brilliant, but the money spends pretty much the same.