Moonage Dream of Venture Capital
The art of slow courage and how the lessons from art transcends boundaries.
There’s a moment in Moonage Daydream, the Netflix documentary about David Bowie, where he speaks of going down to the deep end of the pool slowly. Wading in, methodically, letting the water rise around you until the ground beneath your feet is no longer certain. It is uncomfortable when done initially, but it is also intentional transformation, as we take bets in unknown territories.
And this, it turns out, is exactly what venture capital demands of us.
In a Venture Institute event, Myrto Lalacos touched on this that I believe goes beyond venture, and should be a way of life. Take one out of their comfort zone. The statement seems obvious on its surface. Of course, growth requires discomfort. But there is something sacred hidden in that simplicity. The Venture Institute does not throw you into the ocean. It teaches you how to wade into the deep end. It shows you the geometry of courage.
We live in an age obsessed with comfort. Our technologies are designed to optimize it. Our careers are built around acquiring it. Our social media feeds are curated to reinforce it. Yet every person who has built something meaningful knows a truth that cannot be tweeted into irrelevance! Life is all about putting ourselves out of our comfort zone, as a daily decision to become slightly more than who we were yesterday.
David Bowie understood this in his bones.
The Geometry of Courage
Watch Bowie’s career as you might watch a master swimmer. He did not emerge from the London music scene fully formed as Ziggy Stardust. He spent years in the shallow end, writing, experimenting, failing publicly and privately. By 1972, when Ziggy arrived, Bowie had already spent a decade teaching himself of creative risk. He had learned what it felt like to fail. He had learned that failure was not the deep end of a drowning pool; it was a teacher in a journey through water.
Then, at the height of his success, at the moment when every incentive was to stay in the warm, profitable shallow end, he did something that still bewilders many artists. He killed off Ziggy Stardust. He abandoned the character that had made him famous and dove again into the unknown.
More than a one-time plunge, it was a lifetime of slow wading. Station to Station emerged from the Berlin period, where Bowie had immersed himself in the visual arts, in painting, in European cinema. He was not randomly reinventing himself. He was systematically expanding the edges of what he was willing to attempt. Each album, persona and collaboration was a step deeper into unfamiliar waters.
In a remarkable 1999 interview, before the internet had even truly begun to rewire civilization, Bowie articulated what he called ‘the most exhilarating and daunting’ moment ahead: ‘The interaction between user and provider will be so harmonious that it will redefine our understanding of media’. Most successful musicians in 1999 were still thinking about touring schedules and vinyl sales. Bowie was wading into the deep end of a technological future that wouldn’t materialize for another decade. He was already there, waiting.
This is what separates the stagnant from the eternal. The willingness to keep wading!
The Deep End is Not Abandonment
Going deep does not mean abandoning the shore.
Bowie never lost his technical foundation. His reinventions were not acts of ignorance but of mastery. He did not become a painter without understanding music. He did not embrace electronic innovation without understanding melody. He moved methodically, wading deeper while maintaining his grip on the ground beneath him.
This is the instruction hidden in his approach to risk. You do not venture into the deep end by pretending you cannot touch bottom. You venture into the deep end by walking in slowly enough to know where your feet are at each step.
For the entrepreneur, or any aspirant in venture or otherwise, this means something specific. Yes, you must be willing to fail, to question your assumptions, to step into markets, build products, and launch ventures without the certainty of success. But you do this with intention. With research, advisors, a nurturing and enabling investor at your back, if you’re lucky enough to have one.
In the context of venture, the venture capitalist who funds billion-dollar companies is not the one taking blind leaps. She is the one who has waded into a thousand small ventures, learning the texture of risk at each depth. She has trained her nervous system to recognize the difference between the deep end of calculated growth and the void of recklessness.
The Moonage Dream
What does it mean to dream of the future while still inhabiting the present? For Bowie, it meant each moment was an opportunity to grow, to exchange, to learn. He was not waiting to arrive at some destination called Success. He was already in the act of becoming.
This is the moonage dream that the ought to be enabled, or practiced, depending on which side you are on. Again, in the context of entrepreneurship/aspirations, it is not the dream of the exit, the IPO or the acquisition, or the valuation. But the dream of becoming, of wading slowly into deeper and deeper waters, knowing that the only way to understand the ocean is to enter it, incrementally, with intention and without the false comfort of certainty.
Bowie lived 69 years and spent almost all of them in the process of transformation. His last album, Blackstar, was released on his birthday, two days before his death. Even in his final moments, he was still moving deeper. Still wading. Still asking the question that animates all genuine growth.
‘What if I could do this differently?’
The deep end is waiting and we all have a choice to wade.
Love this.