Why successful founders give the worst advice

I’ve written before about the inherent limits of expertise, and how it is at that boundary that strategy takes over.

What I’ve not written about however is the limits of strategy.

The reason for that is pretty obvious of course, it’s hardly in my best interests.  I’m here to sell you on strategic thinking, and the advantages that accrue when you do it well – however it would be dishonest of me to claim that it’s crucial factor in determining success (particularly business success).

No, the truth is that strategy pales in comparison to one far bigger, and far more unfortunate factor: “the lottery”.

I take the term “lottery” from a tweet I once read but unfortunately can’t locate, and thus can’t credit.  However it went something like this:

“Most advice you hear from successful entrepreneurs boils down to them sharing their winning lottery numbers”.

In other words: the key factor behind many success stories is not strategic, it’s just dumb luck.  By this I don’t mean anything pejorative necessarily; I simply mean that the factor is uncontrollable.  It’s not something which could be repeated with any reliability, and thus amounts to totally useless advice.  We’re talking about things like: random family connections, being in the right meeting, having an unrealistic amount of cash to play with, randomly stumbling across a big break etc. – the kind of things which, frankly, make the world go round.

(Fairly often when I’m curious about a brand’s success, I do a bit of research into their background seeking to extract some helpful insights, only to find myself presented with a factor such as this.  You’d be shocked by how many brands have a celebrity behind them, let me tell you.)

What is particularly cutting about the tweet however is not the observation that so much success is down to luck – it’s rather the implication that many entrepreneurs don’t even realise that this is the case.

They think that what was true for them will be true for others, when in reality their path will often have been so unique and extraordinary that there’s little for the outside observer to learn at all.

I saw an amusing example of this the other day when an influential entrepreneur, Noah Kagan, shared a “cold email” he received, to show his followers of what a great cold email looks like.  A couple of points from it were:

“Hey Noah, I’ve never told you this but you inspired me back in Berkeley.  I was a freshman at the very first CBSA meeting and your pitch seemed to make sense […] 8 years ago I started my own company and we have bootstrapped to $150m in total revenue […] I happen to be in Austin on Monday and would love to meet you for tacos.”

No doubt it was a great email, guaranteed to get a response.  What was striking however was the suggestion that this was in any way “cold”, or that anyone could learn from it.

Even if we leave aside the minor issue of having built a $150m business (which probably would have been enough to get a meeting with most people all by itself), we have the intimacy of both having been in a single pivotal meeting in an elite University 10 years prior.  To judge from the comments below, far from being inspiring, the way it was intended, many readers found the tweet to be depressing and demotivating, as if it were advertising what a closed shop the elite tech world really is, and just how circumstantial success can be.

This then is precisely why, counter-intuitively, extremely successful entrepreneurs do not give the best advice.

They will always have relied on a mixture of skill and fortune – a mixture of the replicable and unreplicable – on their road to the top.  Nothing wrong what that at all, it’s just how things work in the real world.  This makes it hard for them to get a clean read on which parts of their experience are truly useful to outside observers, and which parts are unique to their own personal journey.

It’s ironic really, because you’ll often hear people say something like “why should we listen to a university business professor who’s never achieved anything in the real world?”.  Or indeed they might justifiably throw the same criticism at me: after all, I’ve never created a billion dollar company, so who am I to tell you what to do?

However I think it is our lack of “real world success” that, perversely, makes our advice valuable.  It is not “tainted” by the unique combination of random messy factors which lie behind actual achievement.  Our job is instead to extract the replicable ingredients for success without letting the unreplicable lottery-like ingredients distract.  I’m sure others would disagree, but if you had the chance of getting advice on your business from either a random business professor, or a billionaire unicorn founder, you should probably take the professor.  (Unless you’re looking for contacts that is… then it’s a totally different story!)

In conclusion then, this is ultimately why we must place most of our attention on strategy.

It may not be the number one factor driving success – but it is the number one controllable factor.  It is something which is at least somewhat predictable, somewhat manageable, somewhat learnable.

The other stuff; the lottery stuff; the stuff which will act as the true catalyst for your billions and your cover profile on Forbes or whatever… well, that’s a mystery.  All you can be is prepared for when it comes – and humble in its presence.

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