Possibly - my instinct is to agree with you - however, I also think the 'time factor' is working hardest against the $10M business. In the $100M case, you raised VC and are trading money (someone else's money) for time - you get there faster, you can take more risk, etc.

"Time kills all deals" can be extrapolated into "Time kills all companies".

On the other hand, in the time it takes you (even with VC rocket fuel) to get 1 company to $100M with 10% ownership, you can probably start 2 or 3 smaller business that could end up at $10M.

That's an interesting argument that I hadn't considered. Going for a $1B exit in some ways de-risks you as a founder because you get the press, attention, and connections but with less actual pressure to ultimately succeed since the bet is so big. I'm not saying it's not hard, but a harder path may be turning down the investment (you crazy fool!) to focus on building a really great cash machine in the $10m - $100m range.