4 Reasons You Aren't An Entrepreneur

Listen in on the hallway chatter at any major tech conference, and you'll likely hear it: The rant about the ridiculousness of a certain startup getting an unbelievable amount of venture capital. Oftentimes it’s a successful technology executive at a big company behind that rant, who then starts pitching his startup idea he's never acted upon.

Should a successful IT leader chuck it all and try the startup route? In the weird, upside-down world of startups, the very qualities that make you a top CIO or other business leader can sabotage your chances of getting a startup off the ground. Understanding the "startup brain" not only helps you make that personal career decision, it can help an IT leader who's trying to encourage more of a startup mentality inside his or her large company.

As a five-time startup veteran, I humbly offer four factors that I think help big-company executives thrive -- but that work against their startup prospects.

1. Risk-Oriented Maturity
Leading an enterprise technology team requires an exceptional level of maturity that the average entrepreneur is woefully lacking. CIOs tend to have a more sophisticated understanding of risk and know how to leverage it for gain. Bets are made carefully with much consideration, and cherished projects are killed due to lack of speedy adoption. It’s not personal, it’s just business.

[ Who's in the startup catbird seat? Read The Developer Is King, Google And Startups Say. ]

In contrast, entrepreneurs tend to have this grandiose notion that ideas can change the world. Thanks to our lack of maturity, we are willing to strike out on our own immediately. We tend, especially in the early years, to have a poor understanding of risk and what we are actually getting ourselves into. On the backend, you will often hear, “If I had known how hard this would be, I would never have started.”

2. Successfully Employed
To get to where you are now requires that you were employable from the get go -- rising through the ranks and proving yourself again and again as the “go-to” person. More importantly, you possess a significant amount of political savvy to get (and stay) where you are. It’s rare to find a successful entrepreneur who is not “colorful.” We often hail from the island of misfit toys. Behind closed doors, we laugh about how ill-suited we are for traditional corporate life and share how we got ourselves fired (for the fifth time) and knew it was time to strike out on our own. Part of the reason so many of us start businesses is that we didn’t really have a choice.

3. Power Savvy
Hierarchy makes sense to you. Thanks to your expertise and position, you hold the trump card with vendors, employees, and sometimes even with peers, as your opinion can kill another’s plans. You might wield your power sparingly, even wisely, but you are accustomed to having it, at least some of the time.

If an entrepreneur ever has the luxury of power, it's usually only very late in the startup trajectory. Entrepreneurs are in a very vulnerable position for almost the entire ride. No one is ever obligated to take our calls or help us out. A startup CEO is in a constant state trying to keep employees, clients, vendors and the board appeased. As such, there is no such thing as real positional power. If you are too proud to beg, this is not your calling.

4. Pragmatic
It’s a rare CIO who can stay in this position without showing some willingness to compromise. Pragmatism is valuable and required here. You might have power, but you know when it’s unwise to force projects and agendas.

If entrepreneurs were pragmatic, they would throw in the towel far sooner than the successful ones do. What gives most entrepreneurs their edge is a willingness to withstand discomfort and uncertainty for unreasonably long periods of time. Many refuse to compromise their vision or call it quits. We just slog it out. Ironically, it’s also why many of us never make it to the finish line, as we tend to get ourselves fired once we take on capital.

There is no such thing as a quintessential entrepreneur. We come in all stripes and flavors. And yes, some very successful former technology executives have made the leap and wowed their naysayers. And some successful entrepreneurs have transitioned into great corporate leaders. But know that the qualities that have served you so well as an executive are not qualities common in startup CEOs… and for good reason.

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