For the better part of a year, I’ve been unemployed – not entirely by choice. After graduating from a top undergraduate business school, I survived Wall Street for one year before jumping into entrepreneurship as the first employee at a successful ad tech firm and then as the founder and CEO of an unsuccessful fintech firm. I spent my twenties working for stock – the first time it worked, but not in a life-changing way; the second time it did the opposite. Thus, my current predicament.
Looking for work is hard; looking for work as an entrepreneur, it turns out, is much harder. Here’s why:
You say: “I want a job.”
They say: “No you don’t.”
I hear a variant of this in every interview. The typical interviewee may be asked, “Why do you want to work here.” But, in my interviews, they ask, “Why do you want to work here?” Then they lament: this place is too big, you’ll be bored, there are company politics, everything moves slowly. Neither candid reasons (a lack of courage, a need for stability, and a desire for a paycheck), nor careerist ones (build expertise, learn from the best, contribute to a winner) are taken at face value. To whatever I say, the rebuttal is the same: “you’re an entrepreneur; go start something.”
One can’t help but wonder whether this is an act of self-preservation. In the good old days of the barter economy, if an individual coveted an object that its owner held dearly, the owner would:
“…instead of saying it is very valuable, he says that it is no good, thus showing his desire to keep it. ‘This axe is no good, it is very old, it is very dull,’ he will say, referring to his axe which the other wants” (1)
It’s possible this explanation is wrong (it’s certainly arrogant), but I can’t discard entirely the notion that the hustle, ambition, creativity, and relentless of the entrepreneur would have most middle-managers looking over their shoulders.
But, let’s say you are able to convince your prospective boss that you do, in earnest, want a job, then:
You say: “I can do the role.”
They say: “No you can’t.”
There is a recruitment concept known as the T-Shaped employee. The vertical line of the T represents depth in a specific functional area; the horizontal one represents cross-functional discipline and the ability to work across teams. For most roles in most companies, the former matters more – and, not unreasonably so. After all, the specialization of labor is a fundamental tenet of capitalism. For the entrepreneur, this presents an issue. Let’s take a look:
The Perfect T is like the Abominable Snowman – probably mythical and, if real, exceedingly rare. More often, “functional” hires have sufficient depth, but not breadth. Now, to the real problem: Founders, CEOs, and entrepreneurs can be perceived as being entirely flat – experience across all functional roles, but expertise in none. It’s true, our role as a “general manager” will have come at the expense of some depth, but in reality, we look more like an amorphous blob than a piece of plywood – beyond cursory knowledge in many arenas, but slightly less depth in our “core” than the typical functional hire. The challenge in obtaining a J-O-B is to convince the hirer that a small deficiency in functional know-how can be quickly overcome and is more than compensated for by our other attributes.
Okay, now let’s imagine you somehow persuade the interviewer that you both want a job and are capable of doing the job you want. The final dagger is next:
You say: “I’m committed”
They say: “No you aren’t”
We’ve all heard this before – “Where do you see yourself in five years?” Entrepreneur or not, were lying when we say “here.” In fact, the median tenure of employees in the tech industry is less than two years. At some of the most highly-sought employers it’s even worse – Google, Facebook and Amazon clock-in between 11-13 months. The irony is that an entrepreneur who spent five years singularly committed to his business is seen as a greater flight risk than a staff engineer who job-hopped every two.
Jumping into entrepreneurship as a founder or early employee can payoff big – but, it may not. And, if it doesn’t, explaining why your jack-of-all-trades experience at a couple no-name firms that didn’t pad your bank account is relevant is a lot harder than simply pointing to a few brand names on your resume – even if they are nothing more than window-dressing.
While it’s true the amorphous blob doesn’t fit well into an org chart, the saving grace of becoming one (I know from personal experience) is that you can slither, slide, and shape-shift your way into new opportunities as they arise in ways Mr. T (no, not that Mr. T) can’t. I’ve come to accept this. And to embrace it. So I’m done trying to fit amorphous blob pegs into T-shaped holes.
The real question is: Are you?
(1) Graeber, David. 2011. Debt: the first 5,000 years. Brooklyn, N.Y.: Melville House.