Captain Ahab, the Imperfectly Perfect Venture Capitalist
As a retired English major one of my favorite past times is drawing comparisons between the literary ecosystem, and in this two-part series we’re going to discuss two characters that I believe to be archetypes of the venture capital personae that you’ll find in Silicon Valley and beyond.
A few months ago, I was on a panel for Irvine Tech Week when we were asked what book or other resource, we would recommend to startup founders. Of course, my default answer is Brad Feld’s Venture Deals, a book that I recommend to all my founders, and my past analysts and interns, and honestly anyone who ever asks me for nonfiction book recs.
Unfortunately for me, the person to my right on the panel stole my answer (it is a good answer, can’t blame them for that). So, I stood up there like a deer in the headlights and confidently answered Moby Dick.
I’ve alluded to this at the high level in a previous post, but Moby Dick is a fascinating read from a venture capital lens and has countless lessons that apply to the venture capital and startup ecosystem broadly. Today in particular we’re going to discuss the character of Captain Ahab, and why Ahab is the platonic ideal that venture capitalists and founders should aspire to, while also recognizing his flaws, and how we as an ecosystem can invent a generation of venture capital where our Ahabs capture our white whales of exits.
I love backing founders with chips on their shoulder. One of my founders once told me that he would rather let his marriage and family crumble before he lets his company fail. A little crazy? Maybe. But highly effective. Without getting into my deep-rooted high school and college trauma, I too have a chip on my shoulder. It powers me to work harder, overcome seemingly impossible obstacles, and act with kindness and empathy to others experiencing similar situations. Captain Ahab is the epitome of a character with a similar chip that drives an obsession towards a goal. Although the monomania is a double-edged sword, in venture capital and startups you need to relentlessly pursue a goal and put in an undying effort until your pursuits are achieved. If that’s not Captain Ahab driving the Pequod through hell and literal high water to track his white whale, I’m not sure what is.
With his chip, Captain Ahab embodies the concept of true risk. Ahab is willing to put anything on the line to achieve his goal because of his traumas. Within this, Ahab demonstrates inspiring leadership, resilience, enterprising strategy, and many other concepts that VCs select for in CEOs, and the LPs select for in VC managers. Relentless pursuit is essential to succeeding in the startup ecosystem. It’s often cutthroat, and it will beat you down, chew you up, and spit you out. It’s your job to get back up and keep going, as Ahab goes down with his whale, losing everything in a tragic failure, just as many startup founders do.
Where the ideology falls short though is in terms of the dark side of Ahab’s obsession: self-isolation and arrogance. Sunk cost fallacy is the biggest problem I see with entrepreneurs and other VCs I work with. As VCs and founders, we should dogmatically pursue our exits, but we should never do so at the expense of our friends, our coworkers, and most importantly our own health and wellbeing. You should never give up easily, but oftentimes the writing will be on the wall, either somewhere you work, with your company, or in other senses of life. Regardless of how long you’ve spent on it, how much pain has gone into it, it is often better to cut your metaphorical white whale loose than to sink your crew with you. There’s a famous quote:
Contrary to popular opinion, quitting is for winners.
Knowing when to quit, change direction, leave a toxic situation, demand more from life, give up on something that wasn’t working and move on, is a very important skill that people who win at life all seem to have.
It’s OK to quit. Similar to Ahab though, you never want complacency: if Ahab had been complacent, he would be retired in Nantucket instead of having a shot at true glory and fulfilling his life’s mission. But similarly, you can’t let your obsession drive you to a point where you lose track of who you are. We should be conscious of our limitations, because there will always be another white whale or another fish to capture. Where Ahab falls short in terms of monomania and hubris, we can succeed in relentless pursuit, critical decision making, and empathy.
When I was on the panel and (obviously) was asked to explain my reasoning behind recommending founders read Moby Dick, it was precisely this. Ahab’s story teaches a lesson in balance. Ishmael teaches a lesson in realism. And the book broadly is a book about everything: spiritualism, nihilism, and of course, the eternal capitalist task of making money with high-risk investment. After all, there’s really no industry past or present with more similarity to venture capital than whaling.
