Could many wealthy entrepreneurs repeat their success? How much luck is involved?

I worked for a guy who made millions from developing text entry systems for mobile devices in the 90s. He was working on another project that could potentially have made him even more. Except he was battling cancer, and his health was affecting his ability to manage the business. And then he died.

So that’s luck. Thing is, if you gave me the millions he had made on his first success, there’s no way I could ever parlay that into a new successful business like he might have. On the other hand, there’s no saying that his new business would be successful, even if he hadn’t died.

But if his new business hadn’t been successful, and he hadn’t been sick, he would have been working on his next business, and his next, and his next. This is a guy who would literally come up with several business ideas every day, any one of which could potentially make a lot of money, the only limit was that he had only a limited amount of time on this planet to make them work. But the other problem is that good ideas are a dime a dozen.

So there’s luck, and then there’s luck. Every successful entrepreneur or businessman you ever heard of, has a pretty uncommon skill set, and could potentially succeed at any number of enterprises. Unless they fail, which is easily possible. People get hit by busses, or get cancer, or shot in the face by a mugger. A tornado comes along and turns your new store into a pile of scrap. And on and on. These sorts of risks can be mitigated, but everyone is subject to them. One false move and you step on a landmine.

But if the landmine doesn’t kill you, you can move on and start again. And if you’ve got the skillset to build your first business that failed, you can start a second one. There’s luck in avoiding horrible pitfalls, but people can come back after failure.

But does your successful business make a million dollars, or 10 million, or 100 million, or a billion?

There are lots of really smart, really driven, really visionary people out there. They don’t all have a net worth of billions. It doesn’t seem to me that a guy who runs a company worth a billion dollars is invariably ten times smarter and harder working than a guy who runs a company worth 100 million. There is no one-to-one correlation between business savvy and business success.

On the one hand, Richard Branson is way out on the bell curve in terms of work ethic, smarts, savvy, and so on. Very few people have the combination of traits that make him a success. On the other hand, even though probably 9999/10000 people don’t have the traits needed, that still means that there are thousands of people who do, yet don’t have the success that he does.

Go back to a 20 year old Richard Branson, and you’d be able to tell that he had the potential to be a success. That makes him special, along with thousands of others. Which ones are going to be medium successes, which ones are going to be huge successes, and which ones are going to be mega successes?

Branson is an interesting case - early in his career he fitted the profile of an entrepreneur of the creative caste, whereas nowadays he’s left that behind and become massively successful sucking on the government teat. Quite funny hearing him advanced up thread as a entrepreneur in the libertarian tradition - do they offer government subsidies in liberteria? Cos Branson’s trousered more tax-payers money than I’ve had hot dinners.

I think this points to him being exactly the type of entrepreneur that would be serially successful (as he has been) - bit of a rocky road learning the rules of the game in his formative years (including a very close shave with HMRC on some import/export tax issues IIRC), but is now an operator who can engage any system and turn it to his advantage.