Your portfolio backtesting is based on average market performance. We all know that in the markets, there are extreme winners and majority are losers in long run.
How would you answer to Ole Peter testing?
I mean, my first answer, and it's to you rather than Mr Peter, is that the entire point of owning an index is that you don't have to try to pick the winners; you end up owning them automatically.
The thing I suspect that ST fails to verify is the cash to investment ratio. He is just using emergency fund as a heuristics. After investors had enough redundant cash, they will go overbetting.
This is why people do what's called Monte-Carlo testing. Instead of just backtesting the portfolio, they say "OK, what will the underlying assets probably do in the future?" They use a mean return and an expected volatility (which are, I stress,
estimates; we're trying to predict the future here)
And then, using those inputs, they model the outcome across tens of thousands of possible "worlds", to use your term. That way, you can come up with an expected mean return, but you can also see what the tails of the distribution look like. What's the worst-case scenario?
And you can do this yourself - so, let's do it!
The question at issue is: "If 'investments' is the '110 minus your age' portfolio, and 'cash' is SGD cash, what ratio of cash to investments provides the best return?".
As a starting point, let's use the US market: allocating 80-20 between US stocks and US bonds, and then varying the cash portion between 0% and 50%. The handy-dandy tools at PortfolioVisualizer
let us see how this portfolio would have performed between 1987 and today... and, no surprise, the answer is that the portfolios with less cash perform significantly better. There are higher drawdowns, obviously, but you get commensurately higher returns; and adding a higher cash weighting doesn't give you any better risk-adjusted returns (the "Sharpe Ratio" number).
So all other things being equal, it looks like you want to own more assets (stocks and bonds) and less cash.
Let's refine this, though. Your original complaint was that you thought I was only back-testing based on historical returns, and not looking at the possible worst-case outcomes. We can build our own monte-carlo simulator, plug in some expected returns and volatilities for the assets in the portfolio, and see what the tails of the distribution look like.
I'll write up the script for this tonight or tomorrow and post it on Github. (Disclaimer, I am not actually very good at Python, so my code is going to be awful. Feel free to laugh at it.)
The high-level flow looks a bit like this:
1) Initialise your model of the markets with your variables of choice. I'm going to assume that the returns of three assets - stocks, bonds, and cash - are normally distributed and uncorrelated, which is obviously not 100% right, but it'll give us an idea. (If anything, zero correlation understates how well the 100%-stock-and-bond portfolio will perform). I'm also going to assume continuous dividends and constant interest rates because I really can't be stuffed keeping track of discrete dividend payments (every six months or year) and variable interest rates; someone else is welcome to do this.
2) Generate a bunch of price trajectories for the assets based on that market model. 10,000 or 100,000 is a good number.
3) Find out what the ending value of the portfolio will be across those 10k or 100k trajectories.
4) Draw a nice chart of the distribution of the ending values, and put some summary statistics in there.
I think—and stop me if I'm wrong here—the key question that you'd like to know is: what does the lower tail of the distribution look like?
How likely is it that a stock-and-bond portfolio will do worse than if you'd just held everything in cash?
Is that reasonable? I want to make sure I'm answering the question that you're actually asking.
Company earning of solid dependable companies did not disappear overnight even when the stock market plunged 50%. For example, you can check MacDonald's earnings during the GFC.
One Weird Thing that a few smart cookies realised in '08-'09: people slashed their spending on "large luxuries" (cars, luxury goods, things like that) but they increased their spending on "small luxuries". The hypothesis, I guess, is that people couldn't afford larger splurges, so they spent on smaller splurges instead to make themselves feel better.
Mass-affluent retailers like Whole Foods (a fancy-ass hippie organic supermarket over here; disclaimer, I shop at Whole Foods so I guess that makes me a fancy-ass hippie) did surprisingly well during the downturn.