The Flip Side of Entrepreneurship

Picked this up at (where else) Guy Kawasaki's blog. Oh man - has this been true for us as we've started NCUD. Here Guy quotes Glenn Kellman, the CEO of Redfin. This speaks volumes to me - many of the things he addresses are things I've thought, said or worried about. As someone who has been involved in four start up works and many re-engineering projects in the ministry / non profit world, Glenn's comment ring true. I've edited comments - you can see the full article on Guy's website.

Like the souls in Dostoevsky who are admitted to heaven because they never thought themselves worthy of it, successful entrepreneurs can’t be convinced that any other startup has their troubles, because they constantly compare the triumphant launch parties and revisionist histories of successful companies to their own daily struggles. Just so you know you’re not alone, here’s a top-ten list of the ways a startup can feel deeply screwed up without really being that screwed up at all.

- True believers go nuts at the slightest provocation. The best people at a start-up care too much. They stay up late writing Jerry Maguire memos, eavesdropping on support calls, snapping at bureaucracy. They are your heart and bones, so you have to give them what they need, which is a lot. The only way to get them on your side is to put them in charge.

- Big projects attract good people. If you aren’t doing something worthwhile, you can’t get anyone worthwhile to work on it. I often think about what Ezra Pound once said of his epic poem, that "if it's a failure, it's a failure worth all the successes of its age.” You need a big mission to recruit people who care about what you’re doing.

- Start-ups are freak-catchers. You have to be fundamentally unhappy with the way things are to leave Microsoft, and yet unrealistic enough to believe the world can change to join a start-up. This is a volatile combination which can result in group mood swings and a somewhat motley crew. Thus, don’t worry if your start-up seems to have more than its fair share of oddballs.

- Time. To make something elegant takes time, and the cult of speed sometimes works against that.

- Everybody has to re-build. The short-cuts you have to take and the problems you couldn’t anticipate when building version 1.0 of your product always mean you’ll have to rebuild some of it in version 2.0 or 3.0. Don’t get discouraged or short-sighted. Just rebuild it. This is just how things work.

- Fearless leaders are often terrified. Just because you're worried doesn't mean you have a bad idea; the best ideas are often the ones that scare you the most. And for sure don't believe the after-the-fact statements from entrepreneurs about how they "knew" what to do.

- It'll always be hard work. Most start-ups find an interesting problem to solve, then just keep working on it. At a recent awards ceremony, Microsoft CEO Steve Ballmer tried to think of the secret to Microsoft’s success and could only come up with “hard, hard, hard, hard, hard, work.” This is an obvious cliche, but most entrepreneurs remain fixated on the Eureka! moment. If you don't believe you have any reliable competitive advantage, you're the kind of insecure person who will work your competition into the ground, so keep working.

- It isn't going to get better--it already is. In the early days, start-ups focus on how great it’s going to be when they succeed; but the moment they do, they start talking about how great it was before they did. Whenever I get this way, I remember the Venerable Bede’s complaint that his eighth century contemporaries had lost the fervor of seventh century monks. Even in the darkest of the Dark Ages, people were nostalgic for...the Dark Ages. Start-ups are like medieval monasteries: always convinced that paradise is just ahead or that things only recently got worse. If you can begin to enjoy the process of building a start-up rather than the outcome, you'll be a better leader.

- Truth is our only currency. At lunch last week, an engineer said the only thing he remembered from his interview was our saying the most likely outcome for Redfin--or any startup--was bankruptcy, but that he should join us anyway. It’s odd but the more we've tried to warn people about the risks, the more they seem to ignore them. And since you have to keep taking risks, you have to keep telling people about them. You don't want to be like Saddam Hussein, who never prepared his generals for invasion because he couldn’t admit he didn't have nuclear weapons.

Q. What makes you keep pushing the envolope on existing projects or start new ones? Do you ever feel like you're alone?