Embracing The Hunter Mindset
Why I left a VC-backed rocketship to bet on myself
Last week I made the decision to leave my job at REGENT, a deep-tech aerospace startup revolutionizing electric transportation. It was easily one of the most fun jobs I’ve had in my life. And yet, despite the promotions, bonuses, raises, equity grants, accolades, camaraderie, and perceived status and success, my heart was no longer in it.
I joined as the 5th person on the founding team and first non-engineer. Over the next 1.5 years I helped the company raise millions of dollars from top-tier investors, traveled the world negotiating multi-million dollar contracts across public and private sector, and built out an incredible team across business operations, data analytics, strategy and finance.
That’s when the feeling hit me.
I’m a hunter, not a farmer.
The Beginning
The early days of any startup, or any new venture for that matter, are exhilarating. The hope and optimism is only matched by the magnitude of the work ahead. It is a true 0 to 1 project that requires complete dedication and focus to escape the laws of gravity.
There are no systems in place. No processes. No organization. You need to inspire people to join a mission while at the same time executing on that mission.
It feels like a hunter’s mission.
Eat what you kill.
The Evolution
Since a startup’s goal is to grow fast it will (if successful) evolve into a company over time. Companies have a tendency to grow headcount. Headcount growth turns into more management. More process. More systems. Each new hire becomes an inheritor of a large and growing structure where tasks and functions become more specialized.
It starts to resemble farming.
There’s nothing wrong with farming and most people are better suited for it. There is consistency, routine, and, short of a black swan event, predictability of yield.
OKRs. Performance Reviews. 1:1 Meetings. Leadership Meetings. Cross-Functional Team Meetings. Predictability.
The predictability is where I start to lose interest.
It happens gradually and then all at once.
My sleep starts to suffer. Anxiety increases. Motivation drops. It’s not popular or cool to talk about, but there was something off about me.
I know now that I’m allergic to predictability and order. Unpredictable environments with more randomness and chance are where I thrive. A part of my brain gets activated that brings me into hyper-focus. I’m able to accomplish things I never would have thought possible. After reading Thom Hartmann’s book I believe this is the hunter’s ADHD in action.
It’s not just focus and drive. It’s the zone of genius and living a life of “abundance without accumulation”, as Dominique Willis wrote in a fantastic post on the Hunter-Gatherer mindset.
I’m under no illusions of the cost I bear for this personality trait. Leaving before my 4-year vesting period was up meant literally leaving what could be tens of millions of dollars on the table if the company exits at our projections.
But I felt fine doing it.
In fact, I sleep peacefully at night again.
At 37, I have enough data to look back on my life’s choices and glean some insights. I thrive when my mind is left to wander freely with the space necessary to spot opportunities.
And when I spot an opportunity I become like a madman obsessed.
Justin Welsh recently asked “What business would you build if you were guaranteed success, but had to spend the next 25+ years working on it?”.
Good question.
I can’t say I know the answer, but I do know it would have to be one I was intrinsically motivated to work on. As Daniel Vassallo notes, only intrinsic motivation lasts. And to spot opportunities, you need space in your life to explore.
The Hunt
For much of my twenties I was sure something must be wrong with me. I had no idea what I wanted to be in life so I tried starting several businesses without much success. But one thing was certain–I kept going back to the drawing board. Finally, with my last venture I was able to hold on just long enough to build it to a profitable eight-figures in revenue and replace myself as CEO. Not a flashy exit but also a real, growing, cash-flowing asset I no longer had to manage. I’ve proven to myself I know how to build companies and products.
In hindsight, the few years between building companies where I chose to get a job never lasted more than a year or two. I can’t see myself working on somebody else’s terms for too long. It’s not in my nature.
It’s time for me to come to terms with that. It’s OK to accept who you are, to let go of societal expectations, and just be.
For a while I thought what I wanted was to be part of a unicorn. A rocketship. It turns out that doesn’t motivate me long term.
There is nothing I prize more than independence. Working with my hands to create products and build assets however I see fit. For me, that might mean software, informational products, real estate, heck it might mean writing a children’s book. It doesn’t really matter much what.
All that matters now is that I never again detour from who I am at my core, while making sure my family’s needs are taken care of. The rest will work itself out.
Too many people get trapped thinking they have to stay on a certain course. I believe in experimentation. In play. Seeing what works, what doesn’t, and keeping your ear close to the ground to find opportunities, all while not taking yourself (or life) too seriously. I believe in The Hunt.
If you’d like to follow me on the hunt as I document my journey, you can follow me on Twitter here.
