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- The Wise Founder #12
The Wise Founder #12
A time for Creative Outsiders
Being good in business is the most fascinating kind of art.
If I ask most people to think of a tech founder, this is the sort of image that springs to mind:

First date outfits?
Love them or loathe them, to many they’re the poster children of tech success.
Of course there are differences between them - I have a lot more admiration for how Bill Gates is spending his money right now than Elon. But ideological differences aside they’re cut from a similar analytical, engineering, left-brained kind of cloth. (They are of course all middle-aged white men too!)
But I’ve been sensing for some time now, that the needs and opportunities of this moment are different and that a new type of founder might be emerging in response.
A type of creative outsider. Equal parts artist and business person. Multi-disciplinary by nature - joining dots in ways that others don’t see. As likely to direct a film as build another company.
Edgy, counter-cultural. Wouldn’t be seen dead in a Patagonia vest.
Asked who inspires them, they might namecheck Charli XCX, Donald Glover, David Foster Wallace, AOC, Rick Rubin or even Larry David, over Bezos or Zuckerberg.
Where in the past they’ve hung out in other spaces - music, art, literature etc. They’re now more likely than ever before to become a founder and more likely to succeed too.

Tell me your muses
Now I don’t have concrete data and a nice chart that moves up and to the right to illustrate my point here, but I am crossing paths with more of these humans, and increasingly working with them as clients.
But let’s face it, that doesn’t prove an awful lot. If there’s one thing I’ve learned in coaching it’s that you attract different types of clients largely based on the vibe you give off, so this could simply be reflective of me more fully embracing my own creative-outsideryness and attracting those folks in return.
Yet I have reasons to believe it’s more than that.
Technology
As AI reduces the barriers to build, I see more opportunity for products to be built by artists. Non-technical creative outsiders now have a new medium through which to work and as AI gets more and more powerful - ‘vibe-coding’ there way to great products, or even ‘vibe-founding’ their way to great companies seems to be more of a possibility.
And technology brings about second order effects too. The way companies and products are built, the team size required to build them, the investment required to make it happen - these are all changing in the face of AI. It makes it easier for anyone to become a founder, sure, but none more-so than the creative outsiders, for the simple reason that they were less willing to ‘play the game’ as it used to be played. To pretend to be an insider. To them the new possibilities are a sweet relief.
Complexity
To simplify the work of David Snowden and the Cynefin model - the more complex and chaotic our world and systems become, the more the strategy needs to shift from analysing, categorising and following best practice; to sensing, responding and novel practice.
Perhaps these are times for which the creative outsider, with a more intuitive, sensing, right-brained manner of moving through the world, is perfectly suited?
Culture
Culture is not one homogenous blob. It moves in different directions at once. One of those directions seems linked to a generation rising in the workforce and gaining more control of capital who’ve grown up with crypto, creators and industry crossover. They’ve seen youtubers become multi-millionaires, actors build successful companies, and reality tv personalities become President. Their references for what’s possible are vast. Their expectations around what work is supposed to be are different. And they’re natives of the great online game.
Some fit the description of creative outsider; others don’t. Some will be founders themselves; others won’t. But even those that don’t and won’t, seem more likely to be drawn to a different sort of company and a different type of founder.
So at the intersection of these forces I see a moment for the creative outsider. Not that every founder will be one; just that we may see more than ever before. A client recently described being a founder as ‘a centre of gravity for capital and talent’ and I wonder if the gravitational field may be shifting.
And I’m not the only one. Writing this essay comes off the back of a magical conversation with my friend Danya, whose also written on this topic; in which (amongst other things) we discussed VCs like Asylum and Indie Ventures playing in this space. Institutional money flowing is a good sense check that I’m not going mad.
So what?
You might be asking yourself.
Partly I write this just to name it. To throw out an observation about the world and see what chimes.
Partly I write it with a sense of excitement, curious what might be built.
And lastly I put it out there as a bat signal as I explore ways to bring these folks together in new and unusual ways. If you feel called by the bat signal then please reach out. I’d love to hear from you.

A question
Who are your muses?
A resource
An ask from me
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