Are You An Entrepreneur?

It's the week of Thanksgiving, so I thought I'd keep things light — you'll be full of turkey, mashed potatoes and stuffing, so nothing too heavy. Here are five traits that I think are the most important an entrepreneur can have. Not saying you don't need others, but I do think you need these. Please suggest your five in the comments.

Are You An Entrepreneur?


Those without self-motivation need not apply. You won't have a boss or be on a strict 9 to 5 schedule when running your own startup, so you'll need to be able to get out of bed even when you don't feel like it. A lot of the time working for myself is motivation enough, but there are days when I hate my alarm clock and don't want to work. Still, I jump out of bed knowing I've got things to do. You have to push yourself.

There's an upside, though. The more work you put in, the more successful you'll be and the more money you'll make, all other things being equal. Instead of spending those extra hours putting in more work for your boss, every extra effort you make directly benefits you and your company.

Having a self-imposed regimen is difficult for a lot of people. It's a drastic change from a 9 to 5. I know people in New York who moved from finance jobs into their own startups and ended up in the soup. The difference between the most inflexible jobs in Corporate America and a free choice of working hours was just too much. They thought Goldman Sachs was a pressure cooker, but found out that holding yourself accountable is even tougher than being held accountable by others.


You're going to hear "no" a lot when running a startup. But successful entrepreneurs are persistent people and hardly ever think the word "no" is the last word. What they hear instead when somebody says no is "get back to me again shortly." They readjust in response to events and keep as many doors open as possible.

There's a great story that Fred Wilson tells about how Avner Ronen of Boxee got funding from Union Square Ventures. Avner met with USV for funding and was turned down. He started sending them status updates every month, and finally showed them a realigned product with 100,000 users. USV was investing in Boxee a month later.

Many applicants lacking in persistence would have heard USV's critiques and their refusal to invest and gone a different route or given up altogether. Avner was persistent and realigned his product. He had heard "get back to me again shortly" from USV instead of "no." Entrepreneurs have a knack for making good use of bad news.

Plays Well With Others

An entrepreneur is self-employed but not a "lone wolf." I think working well with others is one of the most undervalued skills of any successful entrepreneur. Way too often I see hotheaded founders thinking they know best in every situation. That's just not possible. And even when they do know best, they need to introduce their thoughts tactfully and not run a train over other peoples' thinking.

If you want to build something large and successful, you'll need to know how to delegate tasks, step aside for others that know more than you, and generally be more of a leader and less of a know-it-all. Nobody likes the kid whose hand is up to answer every question the teacher asks. The kid who only raises a hand with something worthwhile to share and lets others have a turn is making a better impression — especially on the teacher.

I think being sociable in daily life translates well – in most cases – into being able to work well with others. Most successful entrepreneurs can handle themselves well in public, have lots of friends, and generally don't mind taking an active role around people. They relish social situations, make people laugh, and generally people like their company.

Attention To Detail

I don't just mean spotting the ambiguous phrase in your copy. That's part of it, but entrepreneurs need to be constantly paying attention to everything going on around them. You need to be able to take in heaps of information, sift through it, and come out with a better understanding of the whole picture.

This begins with experience. If you don't know what to look for, then it's hard to be attentive to detail. I've outlined what I do in What's a Non-Programmer To Do? but it goes well beyond that. I'm talking about thinking from a macro perspective and then seeing how detail can be brought to bear on it. A few examples of what I'm talking about:

  • You need to be able to spot sentiment among your users. What's the underlying consensus about your product? How are the people feeling who may not be telling you their feelings in so many words? What does this mean for where you should take your product?
  • When you speak to experienced entrepreneurs, how do they feel about your product? Most everyone is nice to your face, but are they really impressed by what you're doing? Do they think it can succeed? Why or why not? What can you learn from your peers? Or are you just going to take they have to say at face value?
  • You receive a complaint from a user. Is there a pattern here? Can you hear something in what they're saying that may not just be specific to them? Is there something in the overall reception of your product that needs fixing, something that may have been unwittingly implied in the complaint?

I think a lot of running a startup requires a grasp of psychology — reading the nuances of what people say and do. I'm not saying that because I have a Psychology degree. You just need some skill in figuring out what other people are thinking, and why, and a lot of that skill comes from experience, not from classroom generalizations about how people think. Pay attention to everything that's in the air.

Quick Thinking

You'll get derailed if you can't think on your feet. A lot is going to be thrown your way and again and again you'll need to be able to turn thinking into action quickly. You rarely have time to run an A/B test or a model in Excel. You need to be able to make decisions with your gut.

Stephen Colbert exaggerates to make a point when he says he thinks with his gut and not his brain; and while I don't advocate ignoring your brain, there's something in what he says. You'll come to plenty of forks in the road where you just need to go with what feels better. (Isn't that what Yogi Berra meant when he said "When you come to a fork in the road, take it"?)

I was at the Master of Fine Arts talk at SVA with the Founder of WordPress Matt Mullenweg last Thursday, and he talked about how WordPress doesn't have a five year roadmap. There's just a feeling they get in their gut that naturally moves the product forward to a new stage whenever they've completed a segment of what they want to do.


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