Tag Archives: startup

How to turn a small opportunity into a big one: the parlay

My career so far has all been a gamble.

More accurately, it’s been a parlay — taking the winnings from one bet and wagering them on another bet, and so on, until your small initial stake compounds into something much greater.

The scary thing about a parlay is that you can’t see a clear path from start to finish. It’s a series of opportunistic, escalating bets over time.

When I left a safe, corporate job to join a startup, I was often asked two questions:

  1. What will you do if it doesn’t work out?
  2. What will you do if it does work out? What’s your career plan after that?

My answer to both questions was the same: I don’t know.

What I was betting on was that if it turned out well, I’d have a set of skills and experiences, combined with the money and personal network I’d need to do something. And being in an entrepreneurial environment, meeting interesting people doing interesting things, an opportunity was bound to come along sooner or later, and I’d be in a position to capitalise on it. The perfect parlay.

In reality, it didn’t work out. I was fired (more on that soon). But despite that, I still have a set of skills and experiences, as well as more money, more time, and more relationships than I did when I left the corporate world. So, even though I failed, I’m still in a position to take those resources and parlay them into something new which, over the past few weeks, I have done quite successfully (so far). Which is what I was aiming to do all along anyway. (So did I really fail?)

Until last week, I sort of realised what I was doing, but couldn’t explain it in any kind of rigorous framework. But that all changed last week with Venkatesh Rao’s fantastic tweetstorm. I can’t do it justice by explaining, it, so you should read the whole thing. But here was the most relevant excerpt for me:

1/ To parlay something into something else is to turn a small advantage into a big one via a sequence of unplanned, but not unanticipated, gambles. It is the essence of finding serendipity.

2/ In an environment shaped by exponential change — Moore’s Law or gene sequencing for example — parlaying is a survival skill.

3/ Parlaying is the opposite of planning. In planning you deliberately sequence near-certain things in advance, to create one future, and plan on breaking nothing along the way.

4/ In parlaying, you daisy-chain bets to create an expanding range of positive possible futures. You pick the most interesting bet at each stage, and expect things to break along the way.

5/ Agility is not just the best approach to parlaying, it is the only approach. The point of operating via iterative trial and error is to predictably create parlaying opportunities, not just fix errors or “test” things.

6/ You’ve heard the term “a rolling stone gathers no moss.” I like to think of agile parlaying as “a rolling snowball grows bigger.” Each pivot is potentially an opportunistic level-up of some sort, not just a course reset.

Like I said, I didn’t quite have the intellectual framework to think about it in these terms before I read this. But now that I read it, I recognise that that’s exactly what I was doing. I put myself in a position where I was exposed to serendipity, and along the way I was building the resources to take advantage of serendipity when it occurred. Unplanned, but not unanticipated.

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