On Youth and Being an Entrepreneur

20 May ’07

The meme on entrepreneurs and age continues apace today, with an essay by Clay Shirky on the idea that young entrepreneurs have an advantage that older folks are lacking:

A couple of weeks ago, Fred Wilson wrote, in The Mid Life Entrepreneur Crisis prime time entrepreneurship is 30s. And its possibly getting younger as web technology meets youth culture. After some followup from Valleywag, he addressed the question at greater length in The Age Question (continued), saying I don’t totally buy that age matters. I think, as I said in my original post, that age is a mind set.

his is a relief for people like me — you’re as young as you feel, and all that — or rather it would be a relief but for one little problem: Fred was right before, and he’s wrong now. Young entrepreneurs have an advantage over older ones (and by older I mean over 30), and contra Fred’s second post, age isn’t in fact a mindset. Young people have an advantage that older people don’t have and can’t fake, and it isn’t about vigor or hunger — it’s a mental advantage. The principal asset a young tech entrepreneur has is that they don’t know a lot of things.

(Fred responds here, and meme has made it into the NYT as well).

Experience is bad in this context, the idea seems to go, because success hinges on finding the new, new way. I think Clay’s point – essentially – is that ‘these kids today’ do things their own way. Well, yes, they sure do – thankfully (well, except for Britney Spears, perhaps). But I’m not sure how relevant this is to Fred’s original point. And while Clay’s argument has at least a superficial logic to it, the ‘sphere is full of stories from young or once young successful entrepreneurs telling tales that begin with “If I’d only known that …”. (The very entertaining Founders at Work has this on pretty much every other page, as I recall). This certainly doesn’t disprove Clay’s argument, but it does suggest that there are some things youth doesn’t know that it ought to – or at least, would not be the worse off for knowing. And of course it’s clearly true that there are other things that it really ought to learn for itself – because this is more effective as a learning strategy, and also because it’s in the act of learning that old ways are disrupted, new ways are created, and so on.

Frankly, I think that something that’s been lost in this meme is the question that’s being asked. One question is “At what age are entrepreneurs most likely to be successful?” Another is “At what age are people most likely to first attempt to be an entrepreneur?” And still another is “Do entrepreneurs tend to be young?” I think all of these have been conflated in this meme, with unclear results.

For my part, I think that people tend to be younger when they first set out on their own for two reasons. One, the question is biased – obviously, something that happens first in time is going to happen earlier than things that follow it later (!). But – ahem – apart from that, the older we get, the more fearful we’re inclined to be. Fear really is the mindkiller. I see it in my practice constantly. And in my experience, younger clients are less influenced by fear. We see this in many aspects of life, of course; this is not a new idea. Fear kills both creativity and action. The large life – the adventurous life – the life worth living – is the life lived without fear. And for a time – a painfully short time, alas – the young have a singular advantage in this department.

I’ve also noticed that older clients tend to be much more negative and cynical about the world. There are many exceptions to this, thankfully. But as a general rule, what I hear from younger clients is “yes, let’s try it”, and what I hear from the older ones is “no, it won’t work” or “here are a bunch of reasons why not”. Smart, well-thought out reasons, to be sure. But obstacles to success, nonetheless. Gross generalization coming, and also a neat trick you can try at home: you cannot succeed at anything if the first words you use to describe it to yourself are reasons why it will be hard, or might fail. I listen hard to the external version of the internal monologue that clients present with, and I learn a lot in that process about their attitudes and mental preparedness. I love spending time with people who have not yet learned the standard catalogue of reasons not to do something risky. I’m sure there’s a list somewhere. And I have a pretty strong impression that older clients come to the table with that list memorized. Creativity is a combustible force in the young. In the not-so-young it tends to get smothered by a lack of oxygen.

A last point comes to mind – what does all of this say about the value to startups of the advice provided by incubators like Y Combinator and TechStars? Perhaps the answer is that the modern incubator doesn’t really give advice – instead it gives things. I’m not sure. Paul Graham sounds like one heck of a smart guy. Brad Feld, too. And they’re certainly smart enough to know that people have to fall down a lot before they learn how to stand. But it’s an intriguing point – if a core element of success is a mind uninhibited by lessons from the past – why learn how to change the future from people schooled in the past? This is, once again, not a novel thought (but then again, I’m over 40, so no surprise there) – Sir Ken Robertson’s superb TED presentation has had me thinking about this idea for weeks now.

I’m not sure why this topic resonates with me so much, but I think it’s partly because I spend so much of my time encouraging the people around me – clients and others – to reach out and take a chance on the opportunities they have. And also because in my former life as BigLaw lawyer I was surrounded by people who carried fear and negativity with them every day. (Environments like that – indeed, perhaps all large institutional cultures – have an almost pathological ability to suppress originality and innovation.) I’ll also add that I consider myself a poster child, at least in my own mind, for the notion that there are exceptions to every rule – including any rule about entrepreneurship being a young person’s game. I don’t want to create the impression that I believe entrepreneurship is wasted on the less-than-young – it’s just not true. I’ve never been more creative in my life, I’ve never before taken the kinds of risks that I am now, and I’ve never been as surrounded by positive, constructive influences (such as mesh) as I am now. This is all by design. I think people are simply less likely to be in this state of mind as they get older.

Can I end with a plug? One of my favourite folks is my friend Mark Dowds, a Toronto entrepreneur and one of the founders of Creationstep (though you may know him from such other businesses at Indoor Playground). Mark’s bio on the mesh site is an absurdly modest description of his ability to think different. Mark is presenting a workshop at mesh titled “Build a Team, Build a Culture”. If you’re interested in this topic, make a note.

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