The Path to the Corner Office

I went to business school to get into Venture Capital, but, at the time, those interviews were hard to get. Also, Business School has a sly way of convincing everyone they should be an Investment Banker or a Consultant, so I found myself sitting in a bunch of interviews for jobs I had no interest in taking.

This makes for a pretty awkward 30 minutes, so I began to treat the interviews like mini podcasts. I’d ask the interviewer about their job and their life and, most importantly, about how they ended up in their current position.

I started noticing that the people with the interesting jobs always gave me the same answer:

“Don’t do what I did - my path was pretty unique”

An example - someone high up at a bank had spent seven years working at a non-profit trying to bring back the oyster population in the Hudson River before teaching math at Success Academy and then working at their cousin’s accounting firm before, finally, joining the bank. In a position most people in the bank would’ve had to put in 10 years to get, he noted proudly.

It became clear that the path to the exceptional jobs was very rarely just working your way through the ranks, because everyone in the ranks has the same inputs as you, so the difference in your output vs theirs is capped. Exceptional jobs are for exceptional people, and it’s much harder to be that much better than everyone else you work alongside.

Here’s the equation for Output:

Output = (how smart/creative/driven you are) ^ (skillsets)(domain expertise)(networks)

If you think of yourself as a product that generates Output (and you can, if you’d like), the equation above is a good representation of what you can spit out. The important thing to notice is that the stuff people focus on - how smart/creative/driven you are - is important but has a capped upside. There’s only so much you can do to improve output through that term. It’s hard to outwork people the higher up the mountain you get.

The exponent is where all the differentiation lies. It’s the only place with a real impact on your Output because it’s the only place you can add totally new things.

If you’re trying to get a job as a VC, say, there’s only so much you can do with smarts/hard work and a knowledge of cap tables. But, if you go work at a restaurant for 18 months, you’ve added to the exponent. You now know a new industry, you understand the supply chain, you speak the lingo, you probably have some network connections. If, on top of that, you worked at a farm upstate or clerked for a water rights law firm…

Smarts and hard work become dangerous when they come with a bunch of unique experiences. They’re less impactful when they don’t.

The path to the corner desk is probably more likely to come from working on a farm in upstate NY for a year than just clocking in to the same job as everyone you’re competing for a promotion against.