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Shirts

Shirts are the future.

Today I did something I do a lot. I was in a room where a startup founder I know and like was pitching to an investor I know and like. At some point in the presentation, the notion ofHoodies came up, not simply as the thing one can wear, but its personification as the one who wears it. Then, a sentence later, the ubiquitous Suits came up.

My mind immediately drifted to an observation of all three of us, educated in different parts of the world, with a range of experiences and orientations, and I noticed that we were all dressed in casual pants, sneakers or casual shoes, and fairly nice shirts.

Shirts are the future.

Shirts understand Hoodies. They don’t scare them off. While Shirts don’t have the same skillset Hoodies do, they understand enough about the Hoodies’ mindset, motivations, and worldview to play well in the innovation sandboxes Shirts and Hoodies need to play in. They can build andsell fine shit together.

Shirts understand Suits. They don’t scare them off. While Shirts don’t have the same skillset Suits do, they understand enough about the Suits’┬ámindset, motivations, and worldview to play well in the innovation sandboxes Shirts and Suits need to play in. They can add massive value to the fine shit Hoodies and Shirts build together.

Hoodies do not understand Suits. Suits do not understand Hoodies. Sometimes this is from lack of trying, by getting sucked into the shallowness of things exterior and small and not making the effort to find common ground, which might be as simple as a fundamentally same rebellion just in different packaging. Regardless, it’s the rare sandbox that can accommodate Hoodies and Suits for a long period of time without Shirts.

Don’t deceive yourself into believing that this is a simple and infinite reframing of the story about how the establishment and anti-establishment don’t play well together. It’s not. And while it’s a cautionary tale, it’s also an aspirational, uplifting one. It’s about how to be a great conduit – of information, meaning, context, intention, and goodwill. And how to build things than can not only change the game, but also change your life.

Shirts are the future. While the shirt above is from Jack Spade, the same shirt from Kate Spade is part of the same future. And we’ll be together in rooms with the same literal and metaphorical Hoodies and Suits of all genders, orientations, experiences, backgrounds, perspectives, likes, dislikes, and things we simply can’t endeavor to understand. It doesn’t change how we’ll build the next generations of what will be worth building. Together.