You generally hear stories of start-ups from exceedingly confident entrepreneurs who have forgotten (or chose to ignore) the day-to-day grind of how they became successful.  Glenn Kelman, CEO of Redfin, writes a great post on The Flip Side of Entrepreneurship on Guy Kawasaki’s blog where he offers “the top-ten list of the ways a startup can feel deeply screwed up without really being that screwed up at all.”

Marc Andreessen liked the “grass is always greener” point and so do I:

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.

Other bits that jumped out at me:

 #1. True believers go nuts at the slightest provocation. The best people at a start-up care too much.

Passion is the fuel of a start-up.  As soon as people stop caring intensely, the effort is doomed.

#2. Big projects attract good people. If you aren’t doing something worthwhile, you can’t get anyone worthwhile to work on it. … You need a big mission to recruit people who care about what you’re doing.

I would argue that “big” isn’t necessary, but worthwhile certainly is.  Great work attracts great people.  You need a clear mission to recruit great people and get them to care.  Great people want to do great work and, while it doesn’t always have to be “big”, they recognize the role that focus and direction play in achieving results.

#5. 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.

Amen, brother.

#6. 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.

As they build a team, I believe that the leadership in a start-up needs to balance calm confidence in the direction of the company with an appropriate level of transparency to the reality: start-ups are inherently unpredictable and plans change. 

At Viget, we’ve had an open policy from the start with the whole staff and routinely discuss everything from changes in service offerings to detailed financials to failed sales opportunities.  We’ve tried to build a culture where everyone can engage in the realities of growing a business.  It requires a degree of trust in the team for being able to “handle” both good news as well as bad, and it presents challenges in terms of leadership because day-to-day decisions are out there for criticism and debate.  I believe that you can be forthright about your doubts and concerns and still a strong leader.  Transparency goes a long way these days.

#7. It’ll always be hard work.

As Glenn points out earlier in the post, stories of sites like Plenty of Fish, which generates millions while the founder works 2 hours per day, show that “hard has gone out of fashion.”  There’s often debate, especially when times are good, about how much time a person should focus on work.  For Glenn, “working two hours a day on my own wasn’t my goal when I came to Silicon Valley.”  When it comes to start-ups, 99% of the time success (beyond just financial — actually building something great)  and really hard work go hand-in-hand.

#8. It isn’t going to get better — it already is.  If you can begin to enjoy the process of building a start-up rather than the outcome, you’ll be a better leader.

I’d take this a step further and say that if you can’t enjoy the ride regardless of how it ends, you shouldn’t bother.  Work on something you love to work on.

#9. 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.

Great story.  Truth and transparency really matter.  I think people who still try to run a business without being open and honest are going to have a hard time attracting great people and achieving great results.

Self-effacing posts like Glenn’s aren’t common enough, probably because both blogging and entrepreneurship tend to attract the over-confident.  While great success stories can be inspiring, a dose of reality can sometimes be more significant to helping a start-up get started.