Dirtbags and Delinquents
“If you want to understand the entrepreneur, study the juvenile delinquent. ‘Cause they’re saying, ‘You know, this sucks. I wanna do it my own way.’ That’s what the entrepreneur does. They just say, ‘This is wrong. I wanna do it this other way,’ and that’s the fun part of business actually. I love breaking the rules.” – Yvon Chouinard
Since I started mentoring in 2016, I’ve met hundreds of founders.
For many years, it was a quiet little thing in the background - conversations that happened in between running my company, navigating the swells and troughs of being a (somewhat faulty) first-time CEO. Over those years, I’ve seen amazing successes and utter failures of business ideas, but nearly every founder I met, perhaps excluding the very few who treated entrepreneurship as a lifestyle, had a bit of a “screw this, let’s do it better” mentality.
It’s an attitude that transcends tech founders. Dirtbags and artists, adventurers and athletes, and miscreants and thinkers of all stripes seem to share in this essential (with a nod to Chouinard) delinquency.
One of the challenges of being a founder - especially backed by venture - is that we get pushed into roles where we are uncertain about how to act. For a first time CEO, that might be when raising capital, or leading an executive team through a challenge, or having to conduct layoffs; most of us haven’t had the benefit of years of grooming for becoming a senior executive, let alone direct experience with and for these situations. So, like anyone, we build up a concept in our heads about what leadership looks like in these moments, and then we emulate them.
“Fake it until you make it”, as the saying goes.
However, operating this way is at odds with authentic leadership for a founder who has set out with that sort of punk-rock, there-is-a-better way mentality at their core.
These are undoubtably serious moments, worthy of consideration in how we respond to them, and in my experience, the key to navigating them well begins with a deep, sustained period of introspection, asking questions like:
What is the core issue? Is it something deeper than how it initially presents itself?
What is within my control, and what is not?
What would the ideal outcome be, given the limitations we face?
What would the worst outcome be? What’s at stake, really?
What can we do to reach the former, and avoid the latter?
What do I know? What do I not know?
Who can I lean on for help? Who can I be totally open and vulnerable with, and where do I need to more carefully manage my communications?
And perhaps most importantly: “how do I want to show up here?”
This is not work that can be done in a half hour. It’s sustained, difficult, and rewarding - because it requires connecting the humanistic, vulnerable, even emotional aspects of a founder’s psyche with the specific business challenges they face, and it has to be done over and over again.
If you’re in that space, and want to talk, please feel free to reach out; you don’t have to figure this all out alone.