Are You A Serial Entrepreneur?

Here’s a paradox. People quite often fear success. To the extent that they will actually self-sabotage to ensure they’re not successful. If you’re successful, the thinking seems to go, you’ve got your head above the parapet, you will get noticed, you can become a target, so better perhaps to keep your head down, strive but don’t succeed. 

Also, if you are seen as not trying too hard then it’s easy to explain away failure or lack of success. 

‘I wasn’t really trying.’

‘Well, I couldn’t give it all my attention, I’m too busy.’

People like that need to remember that quote by Henry Ford, the man who started the Ford Motor Company. 

‘Whether you think you can or think you can’t – you’re right.’

Success Is Not Always Serial

But others want success more than they want oxygen. We’ve written before about questioning your motives as to why you want to run your business, why you want to succeed. And if your motives are good, and what you are doing is right for you then success will taste sweet. 

There are real upsides to success, so obvious it’s not worth discussing them, but they’re real and they’re often fun and deeply satisfying. But a word of caution. 
This is aimed more at the serial entrepreneur than the one-off. And we’re not talking here about W K Kellogg, who started Kellogg’s back in the 19th century and then went on to be the breakfast king – he was a cereal entrepreneur!

Real story, but we’re not mentioning names. A chap had a really good idea for a new type of car magazine, back when magazines were a big thing. He launched it himself, it took off big time, he made good money, then he sold the magazine to a major publisher, thus making himself a load more money. Happy days. 

If he’d stopped there all would have been well. He did indeed stop for a bit while he focused on buying a bigger house, some more vehicles, and all the other things people mistakenly think will make them happy. Fine. 

But then he thought: I’m brilliant, me, look what I did. I can do it again. I’ve got the golden touch. So he got a lot of money together and launched another magazine. It bombed, taking a lot of that money with it. Reputation damaged, finances damaged, self-belief damaged. See how success led to a lack of learning. Like Nelson Mandela said:

‘I never lose. I either win or learn.’

Get Lucky

In truth, like a lot of people, he’d had a great idea at the right time, and cashed in on that. That doesn’t make someone a serial entrepreneur, like that man, that made him lucky at the time, plus he added a lot of hard work and commitment. 

You’ll need that luck if you’re to become a serial success. It’s a different mindset, the serial entrepreneur. You’ll often see one tell-tale sign. A serial entrepreneur will start a company and be moderately brilliant at getting it up and running, but won’t actually be very good at running it day to day once it’s working. 

If they’re smart they hand over that running to other hands while they set off for new horizons. And the really good ones, the ones who see themselves clearly, acknowledge that luck plays a definite part. The harder you work, the luckier you get, as they say, but luck is still there. 

Nassim Nicholas Taleb, the philosophical financier, put it like this: 

‘Hard work will get you a professorship or a BMW. You need both work and luck for a Booker, a Nobel or a private jet.’

Be lucky.