DMC: The problem with your argument is that everyone’s story is unique, so you can always find something they did or didn’t do that you can claim was responsible for their success, then chalk it up to ‘luck’. For instance, you’re giving Richard Branson the ‘luck’ label by claiming that the success of Tubular Bells was what made him. But by definition, some song had to be popular for a record company to succeed, so you can make that claim for just about any of them. And besides, your claim is unfalsifiable in the sense that we’ll never know if Branson would have made it anyway with another song, or an entirely different line of business.
Part of the point of recognizing serial entrepreneurs is that it shows that there’s more to it than luck. Even if you’re right about Jobs lucking into being friends with Woz, the fact that he succeeded with multiple other ventures after Apple would suggest that maybe he had more than luck going for him. But on the other hand, maybe part of Jobs’ genius was spotting genius in others and working with them.
The same is true of Elon Musk. You’re chalking his success up to being paid too much for Zip2? That’s quite a stretch. How do you know how much capital he needed? For that matter, I didn’t even mention Zip2, so that’s another successful venture the guy can add to his resume. And for all you know, Compaq overpaid (if it did) because Musk is a very good salesman.
If you really want to figure out whether these people were just ‘lucky’, you have to dive more deeply into their bios. Musk is a fascinating guy - incredibly driven, and incredibly smart. He didn’t just start Tesla and SpaceX, he did a lot of the engineering himself. Steve Jobs clearly had a brilliant mind for products and design, despite having almost no formal training. If you ask me, Apple is showing signs of mediocrity again now that Jobs is gone.
One thing you’ll see as a constant in all these people is that they work their bloody tails off. Even when they’re playing, they play hard. You won’t catch many of them just sitting around watching TV all night. Some of them race cars, some of them set aviation records, some of them start still more companies for fun or get involved in philanthropy.
In my opinion we all get our shot at ‘lucky’ breaks. Some people are just better prepared to take advantage of them when they come along. Others make their luck by standing out from the crowd. It’s amazing how ‘lucky’ you can get when you work your ass off.