Well, a megalomaniacal founder who wants to hire 10,000 people and run a huge company has the exact same baggage as his large competitors. The baggage is just cultural, rather than business baggage or technical baggage. I think investors like Aaron Levie, who's all around a brilliant and highly accommodating guy, don't recognize that cultural baggage exists at day 0.
> Don’t hedge your bets.
That makes sense from the point of view of an investment portfolio manager, where you would want all of your companies to do the thing you actually invested in them to do in order to achieve diversity. But from a business point of view, bifurcating strategy could make a ton of sense.
Maybe we're talking about different companies. I really admire places like Valve, which definitely regard culture as their main source of enterprise value (rather than some notion of legacy-free competitiveness) and bifurcation (game development and store management) as successful. You could find lots of people who wouldn't care to found a Box.net. But who wouldn't want to found Valve?