The spread between the free and the entrenched

There are an awful lot of products and services being given away nowadays. Everyone has an advertising model at play, but you and I both know that won’t last forever. How do you capitalize on the this latest (and it seems, recurring) trend before it whithers? Well you could start an arbitrage fund – the targeted spread being an investment in the free services, and a short of the entrenched, charging corporates.

Interesting idea, but private company valuations are somewhat arbitrary, while listed stocks are easy to get a fix on. Figuring out how much to bet (which is just as if not more important that actually picking the winners and losers) on each side of the arb play is the missing link here.