Never Underestimate Luck, You Lucky B***ard

"You lucky, lucky, bastard" - Monty Python the life of Brian

Do πŸ‘ Not πŸ‘ Buy πŸ‘ Your πŸ‘ Own πŸ‘ Hype. Founder rule number ONE: be humble, stay humble. You really ain’t all that.

As you progress in your business goals as a founder, you will get told more and more about how impressive and incredible it has been for you to build the business you have, and how much effort, hustle and deep strategic insight you must have had in order to so so well.

This kind of praise comes from investors, partners and peers quite often, and it’s absolutely awesome to hear because – if you’re anything like me and crave validation of any sort (does it show that I’m an only-child?) – it feels good. But in those immortal words of Skunk Anansie – “Just because it feels good, doesn’t make it right”.

Moreover, when you start hiring more, and your team starts to swell beyond that 40-70-something “cosy start-up” stage, you’ll start hearing it from your staff – I call it the Founder Reality Distortion Field, and it happens when you start to meet team members you may have not directly hired or interviewed yourself. To them, as a once-removed (or twice-removed) hire, you are in an ivory tower, untouchable, impregnable, and omniscient (this is especially true of remote-first businesses like Tyk) – only spoken about in hushed whispers by those senior enough to be directly connected to you (ok this is an exaggeration, but I hope you see what I mean).

The reality distortion field actually ends up spreading, as anyone in your organisation becomes more senior, the closer they are to the exec, the more the distortion field addles brains and causes them to be suddenly far too polite, and even more horrifying, far more likely to not be honest when you fuck up.

Success can breed arrogance, especially when your peers constantly keep telling you how amazing you are, and that’s a trap.

What many don’t understand or realise (and something that you yourself should get to grips with extremely early on), is how fucking lucky you are to be where you are.

There’s two forms of luck, structural luck, the privileges you are born with, and dynamic luck, the unlikely events that (most likely stem from privilege, that occur in your life that offer key opportunities to succeed)

I’m pretty fucking privileged, check out my character sheet:

  • White European male of above average height (+1 charisma, +1 wealth)
  • Only child to stable upper-middle-class household (+1 wealth, +1 initiative)
  • Bilingual, educated to postgraduate level (+1 intelligence, +1 barter)
  • Born in the EU (+1 luck, +1 movement)

There’s probably way more… this is meant to be illustrative.

Now, there are many successful business owners that have been born with little-to-no no privilege, those folks are the exception that proves the rule, because most folks do come with a whole bunch of built-in-advantages that give them a leg-up on their journey that others just don’t have. I have nothing but respect and admiration for folks that succeed against the odds.

I’m not one of those though, I know that the odds (at least so far), have been stacked somewhat in my favour.

Now onto dynamic luck – this is actually where it gets interesting, because this is where there are opportunities to influence how much of it you have access to. If you think of luck in terms of probabilities, luck can be defined as unlikely events that occur, that provide an above average long-term outcome.

In your life, many events occur in your day to day, but since lucky events are those that are unlikely to happen, the only way to influence luck, is to influence the amount of unlikely events you can experience – the only way to do that, is to increase the number of overall events.

Ok that sounds dumb, because it’s a probability of a probability, which is just two probabilities added together, but hear me out…

If you spend your day every day in the same routine (wake up, go to work, work, come home, do something fun like hobby, sleep, repeat), the amount of “hooks” in your routine where more randomness is injected – randomness here being other people’s activities that impact you – are during work, and maybe during your fun activities (and only if they have you interact with other people).

Given in a routine day – your work day will likely have you interact with the same people over and over again – which means they are less exposed to randomness as they are in their own routine, so the range of probabilities within this event group are relatively flat, the same goes group activities (routine on routine means you are in the fat bit of the normal distribution). Now I’m not saying this is a bad thing, this is a stable life that I think most people want. However, to increase opportunity (the likelihood of unlikely events), you need to sow some chaos.

Now I’m an awful example of this, because I very much like stability and a semblance of a routine – even though I chose otherwise eventually, I think I was almost dragged there by someone who is exceptionally good at creating opportunity: my co-founder.

Unlike me, my co-founder is the type of person who will go to events and network, go to meetups that aren’t in his forte, take calls with folks he’s never really met, and expose himself to variability where he can. He likes to sow chaos and see what it rewards. There’s a few core deals that got us to where we need to be, that wouldn’t have happened without him being aligned as a chaotic-good.

So for me, a key unlikely moment in my life was meeting my co-founder. Tyk wouldn’t exist as it is today if that partnership had never been made.

That meeting was an exceedingly unlikely combo of events – because I met my co-founder via my unbeknownst-to-me-at-the-time–future-wife, when she hired both of us into the same cohort of project managers at our old job. So applying to one job netted me a beautiful family, an incredible partnership, and my own business.

That’s the contribution of luck to my success.

If you lose sight of it, then the cost is hubris in your own capability and fallibility – and that’s when the mistakes happen. Don’t drink the Kool-Aid, don’t get high on your own supply, and never underestimate the power of probability.

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