Tomorrow Patrick comes to stay. My couch has missed him, and so have I. He’s one of my favorite people in the whole wide world, and though both our worlds are wide, we share a hometown. I grew up in Limerick in the 1980s, and he grew up there in the 2000s.

Among many other things—student, hacker, writer, pilot, traveler—Patrick is an entrepreneur. He was 17 when he started to write software that would make life easier for middle-aged eBay sellers, and 19 when he sold it. Paul Graham, whose essays I’ve long admired, was his mentor and investor through his Silicon Valley incubator firm, Y Combinator. (I’ve wondered if that “Y” indicates the chromosome requirements for running programs, but that’s a mean little thought.)

Since then, Patrick has gone back to college and kept up his start-up ventures, from making Wikipedia fit on an iPhone to designing payment systems for developers. Every so often he’ll tell me off-handedly that he is meeting with some improbable supporter—the president of the European Commission or some billionaire CEO. And we laugh at the ridiculousness of this world that will give you all kinds of unexpected help as long as you have the balls to try, the brains to back it up, and the belief to keep it going.

Though I work with big corporations, my favorite clients are usually founders rather than career executives. They are the artists of the business world, who see what isn’t there and bring it into existence. They are romantics.

I suppose I collect entrepreneurs. I’ve worked for start-ups, made friends with many founders, and even married a man who turned out to be one. Ten years ago, when we were deciding how much of our savings to put into his new business, my ex-husband said, “Owning stocks is betting on other people. I’d rather bet on myself than anyone else.”  I’ve never forgotten it. It wasn’t a bigger appetite for risk, it was a different definition of risk. And it was just the opposite of everything our Irish upbringing had trained us both to work for—the gold stars of a good Leaving Cert, a profession, and assumption into the Dublin elite.

Even now, it’s hard to imagine preferring to bet on myself. But Patrick would take that bet, I’m sure. It’s a confidence shared by the twenty-odd entrepreneurs I know across different fields and different countries. It sets them apart from those of us who look for the misleading signals of other people’s belief. As I got closer to start-ups in the 1990s, I noticed how many people felt more secure joining a new company with 60 employees rather than six. What the crowd thinks matters more than where the cash is going.

I didn’t mean for this to turn into an essay on enterprise—especially as Paul Graham does those so well—but I find myself listing the traits that make founders different:

They are challengers.

When I move into an apartment, there’s a period of about two weeks when I can see what could make it better. Then I get used to it, and for years that crooked mirror stays where it is. Entrepreneurs don’t get comfortable with the mediocre. They see the gaps between what is and what could be.

Sometimes, they even see gaps for other people.

Much of my consulting work involves enforcing empathy—helping clients  see the world from the perspective of other people. It’s  hard, and that’s probably why so many founders start or stick with the stuff that they themselves (and their friends) care about.  We end up with no shortage of t-shirt design companies, indie coffee shops, and mobile apps.

But some people can look beyond their own tribe to identify what people who are not at all like them might need or want. I’m thinking of Patrick with his eBay seller tools, or Cameron Sinclair building houses for and with the four billion people who are neither destitute or rich, or Liam Casey helping people dance with the chaos of the global supply chain.

They have a bias for action.

They might  play with ideas in words for a while, but before long they want to make a prototype. And then they want to move it forward. And forward again.  “That thing we were talking about last night? I mocked it up. I think it could work.”

They are connectors.

“Do you know so-and-so?” The entrepreneurs I know are constantly suggesting and making introductions—texting mid-meal to someone you “should really meet.” Karma is capital.

They can inspire others to help them.

Sometimes it’s charm, sometimes it’s force of will, sometimes storytelling. However they do it,  founders have an ability to make other people see something, believe in it and pitch in. And often, they just ask for help directly—an underrated superpower.

They define discomfort differently.

I like having someone else worry about my paycheck, even though that means it’s much smaller than an independent practitioner’s. And I like the notion of “after work”—the time for Down Dogs, bon-bons, and Mad Men.

My founder friends can tolerate a level of uncertainty that would paralyze me. They can live without material comforts (on my couch), and drive themselves like mill horses. What they can’t stand is the idea of spending their time and talent on someone else’s ideas.

They don’t need approval.

Several of my entrepreneur friends are academically brilliant—and several others struggled to pass school and couldn’t wait to get out. But none of them got hooked on hits of teacher’s praise, and they avoided a lifelong addiction to recognition from above. Their own opinions matter more to them than those of authority figures. In a strange way, I think this frees them up to ask for and listen to advice more effectively, because they’re looking for information, not confirmation.

Above all, they are relentlessly resourceful.

Paul Graham pointed this one out as the key defining trait of successful entrepreneurs. They will find ways to get around problems and get stuff done, long beyond the point where sane and well-adjusted people would abandon a project.

I feel lucky to know so many makers and doers. Life is more vivid with people who are shaping some corner of the future, however small. You get to talk about possibilities, fears, creativity, change, big choices, leadership—all the good stuff. And I know, too, that it can be lonely for founders, who must constantly project certainty even as they suffer night sweats over making payroll. For them, being able to question, worry, or even just gossip with an outsider can be a break from a consuming enterprise, and for me—well, it’s nice to feel useful.

This entry was posted on Tuesday, January 19th, 2010 at 1:58 pm and is filed under Peace and Love\, People\, Technology\, Wild claims, Work\. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.