One of the real perks of my job is getting to speak to some of the incredibly bright, impossibly young students at business schools across the country--most of them openly angling for the life of an entrepreneur. To this end, I like to conduct an exercise that illustrates what I think it takes to pull off the role.
I begin by asking those already working on a company of their own to stand up. Unsurprisingly, in these heady days of tech riches foretold, almost everybody does. Then I tell anyone who is financing their own business--via cash or credit card--to stay standing. About half the room usually sits down, many no doubt sensing a trap based on the oft-perceived folly of self-funding. Then, from among those still in the mix, the winnowing begins. I tell this dwindling collection of folks to stay on their feet if they've racked up debt of $10,000, $20,000, $30,000--more than your student loans?--until I end up with one poor soul--so unbelievably leveraged--that the now-agape audience is sure I'm holding them up as some kind of cautionary curiosity of the digital age.
And that's when I announce to the whole class: "This, ladies and gentlemen, is your entrepreneur."
It's a fun moment. There are incredulous murmurs, restless shifts, some doubtful guffaws. And, of course, there's a look of much-appreciated validation beaming from the face of the last remaining student, despite the possibility that they have racked up more debt than they can ever repay.
But the eventual success or failure of this person's business model is never the point. The point is that they have already proven to me their suitability for life as an entrepreneur. How? Because they clearly suffer from a near-fatal level of optimism--which should be the entry-level qualifier for anyone looking to lead their own company.
Optimism, as a concept, has had a rough go in the business world, which prefers more active and demonstrable attributes: tenacity, resilience, perseverance. Optimism, on the other hand, often has an earnest, leave-it-to-the-fates perception that is pure boardroom death--to the point that business leaders who say they are optimistic about anything at all are quick to qualify that they are only "cautiously" so.
If you're an entrepreneur, however, being cautiously optimistic isn't going to cut it. Enduring life as the leader of a startup takes the other kind of optimism--the uncut, unfiltered, Orphan-Annie-walking-on-sunshine kind we don't like to cop out to for fear of jinxing something. The kind of unshakeable optimism that gets Wile E. Coyote out of bed in the morning. It's not enough to simply block out downside thinking; you have to be literally incapable of it. You can't waste time and energy mapping pitfalls and setbacks; you have to be impassively, completely oblivious to them--because they're going to be constants in your role as an entrepreneur.
Entrepreneurs might get labeled as thrill-seekers and risk-takers, but both archetypes are actually deeply moored by a sense of blind optimism. Say what you will about the maniacs who strap on wing-suits and jump off mountaintops, but "pessimist" likely isn't one of them.
Of course, optimism alone isn't enough to make a successful entrepreneur. But, for me, it's the binary litmus test that determines whether someone will be happy in the role. And the fact is, many of the personality types attracted to other prominent roles in tech often do not find entrepreneurship a fit.
Venture capitalists might sound like they embrace uncertainty and adventure, but they're actually in the risk-mitigation business. They're often betting other people's money (not their own) while critically addressing two things: what can go wrong, and how they can protect themselves from the "what if?" scenario. You actually couldn't find a job description more antithetical to being an entrepreneur if you tried.
Engineers may be the backbone of any successful tech company, but anyone who spends most of their waking hours examining the myriad ways something amazing might break is likely to be very unsettled in a role where everything feels like it's breaking all the time.
Sometimes, even experience itself can degrade a perfectly healthy sense of optimism to the point it fails to serve as the entrepreneurial energy source it needs to be. After all, when too many experts get together and kibbitz pragmatically about their area of mastery, I've found that they mostly serve to terrify each other to the point of paralysis.
There are numerous exceptions to each of these gross generalities, of course. And none of this is to say that a good old-fashioned realist can't succeed as an entrepreneur. But it's been my experience that people who identify upside by focusing on how to minimize downside are often temperamentally averse to the role, and their business suffers as a result.
So what's the best thing to do if you're considering life as an entrepreneur? First, ask yourself honestly and introspectively about whether it's in your genetic makeup to remain oblivious to the innumerable impacts that non-stop chaos will have on your new life as an entrepreneur.
If it's not, your day-to-day as a startup leader is likely to be a soul-sucking grind that will make you question the very reasons you wanted the role in the first place.
But if it is, you've probably read right over every one of my warnings and might very well be a born entrepreneur--just like that last student standing at my college talk.
But please go easy on the credit card debt. That stuff will seriously haunt you.