Cognitive Strides: From Founder to Investor and Back
I was mentioned in an article about the different mindsets maintained by entrepreneurs and investors. The question was: Is it helpful to do both?
The author argued being pessimistic was an asset when investing— “That won’t work!” — while entrepreneurship requires inherent optimism — “This product will change the world!” Based upon my experience in building both Kernel (company) and OS Fund (VC firm), I think he’s mostly right, with some additional nuance.
I have to make hundreds of smaller decisions in a given day at Kernel, but OSF requires longer-term thinking, what I like to think of as “cognitive strides”.
Building Braintree, from 2007 through 2013, required shorter cognitive strides—as in, many immediately pressing considerations. Payments is a mature industry where innovation happens incrementially.
At Kernel, we’re on the bleeding edge of science and technology, doing things which have never been done before. This requires longer cognitive strides; deeper ruminations, fewer distractions and a more expansive thought space.
From a numerical comparison, I’d estimate that Braintree required at least 10x the number of decisions in any given day than Kernel requires.
Transitioning and finding flow in my cognitive stride from when I sold Braintree in 2013 to building OS Fund and Kernel in 2014 and 2016 respectively, required careful introspection and the recalibration of cognitive habits. The contrast was jarring and disorienting initially.
Finding optimal cognitive flow between Kernel, OS Fund and the extensive writing I’ve been doing lately (i.e. A Plan for Humanity) has been deliciously fun. Interestingly, as I’ve found my flow among these primary activities, using Twitter, Facebook or Instagram is painful, counterproductive and damaging for my brain’s ability to maintain the appropriate cognitive stride.
Running more than one company requires my decision-making scales to expand and contract accordingly. Is that helpful for both companies? Probably. Is that optimal for an individual brain? For me it has been. I’ve found it thrilling and enlightening. This idea of “cognitive stride” brings to my mind the difference between China and the U.S., and the cognitive strides each country takes respectively based on their political systems.
What does your cognitive stride mix look like?
