[bapadna]

Your argument is only true for people who have only one business idea. If you have a wealth of ideas, you can execute one and sell at a point that gets security for your self and your family, then execute another and aim bigger, but with your downside risk eliminated.

[_delirium]

Is that common, though? When I think of companies that shaped the tech industry in a huge way, very few are companies founded by people who had already had a big exit and were on to their second or third company after already becoming millionaires. Impact on the scale of Apple, Google, Microsoft, Sun, nVidia, Oracle, etc., seems to involve founders who stay with their companies and guide them over a period of decades. Jobs did try the second-company route via NeXT, which had some impact, but he eventually had to return to Apple to get the kind of impact he wanted, which he wasn't able to do via NeXT (though he brought a good part of it back with him).

[srwh]

You can't compare (or compare in an unfavorable way) the fundamentals of these companies with the fundamentals of hyped web companies, also many of those companies were profitable quickly and follow the IPO way. FourSquare will be here in ten years? Twitter? Zynga? M&A can make them durable but IMHO their fundamentals are more volatile: Google is not just a company who configured open source software and develop some scripts, some of their processes (adwords) can't be even copied with virtually infinite money (microsoft=>adcenter, yahoo=>overture, Apple=>iAds). We can argue that you can't copy/trash the network effect of facebook but we are in the prehistoric moments of the hypercompetitive web and their fundamentals are more volatile.

[philwelch]

Elon Musk. PayPal, SpaceX, Tesla.

[bapadna]

Jobs also had Pixar, which had an undeniable impact in it's field.

Here's a question to test if you really believe the argument you seem to be making:

You have the idea of your lifetime. It's a billion dollar idea. You are looking for a co-founder, and find two amazing prospects.

They are equal in every way (education, drive, interests, etc) except one: Jim spent the past five years working at a startup that he just sold for $20m. Tim spent the past five years working in an office job.

You can only pick one of them. Do you prefer Tim or Jim?

[nostrademons]

I don't think that's really testing the argument he's making. He's arguing that people are more likely to start giant companies on their first go round, not that they're more likely to prefer cofounders who're on their first go round.

When you're looking for a cofounder, you're naturally biased toward someone with relevant experience, because the whole point of recruiting them is so that they can add value to the business and increase its chance of success. But when you're the initiator, a large portion of your contribution is picking the initial direction of the company, and what it's trying to accomplish. It's quite possible for first-time entrepreneurs to pick more ambitious goals and yet have less of a chance of success than repeat entrepreneurs.