Anyone involved in the Startup world is well aware of the name Paul Graham.  His essays offer deep insights on startups from his experiences and realizations.

This month he spoke at the 2009 Startup School as part of an all-star group of speakers.  He posted a summary of his talk on his website titled “What Startups are really like“.

I found this essay struck a few deep chords with me.  Having been self employed for almost 10 years full time now, and 15 years since I started freelancing… this essay had me nodding a lot since I always had a startup aspect to at least one project going at all times.

I highly recommend it for anyone to read in general as there is some good advice that everyone can benefit from.

Paul spoke about 19 key points and I wanted to offer my thoughts on a few of them, one post at a time, from my own experiences in the last 10 years.

1. Be Careful with Cofounders

This was the surprise mentioned by the most founders. There were two types of responses: that you have to be careful who you pick as a cofounder, and that you have to work hard to maintain your relationship.

What people wished they’d paid more attention to when choosing cofounders was character and commitment, not ability. This was particularly true with startups that failed. The lesson: don’t pick cofounders who will flake.

Paul is bang on.  Do not confuse activity with results.  Do not confuse what a potential cofounder says, does, and says they do.

Define success.  Define how you’ll get there.  Define why it’s being done that way.  This is one place where the “why” of what you’re doing is infinitely more important thatn “what” you’re going to build, or “how” you’re going to build it.

I have had more experiences, successful and not; working with strangers, and friends on many projects to have learnt this the hard way.  Success is doing what others are not willing to do, longer, harder, deeper and when some may walk away. I have heard that you shouldn’t work with friends and done it anyways.

I have worked with complete strangers and ended up with the same results.

As cofounder friends, you must:

• have a history and understanding of each other as friends first,
• to frame the relationship as ‘co-founders’ in one place and as friends in another.
• know if you’re good enough friends to get through adversity together.   Separate the buddies from the brothers that have your back anytime, anywhere.  Those are the people you need with you in the trenches.

Working with a cofounder that is a friend is not much different than dating and deciding to be “serious” friends.

Beyond that, as good friends:

• Have you been able to solve other problems together using each others strengths?
• How do you resolve or go through things you don’t agree on being important, or solving one particular way?
• Have you had a disagreement that was major enough that we both were able to still come together, talk, understand each other, and choose what’s best apart from your mutual preferences?
• Are you in a startup for the same reasons?
• Is your co founder looking for the long haul and you’re looking to cash out?
• Life wise, would you handle marriage (if single) and the impact of other commitments in a similar way?

Guess what you’ll be doing in a startup!

The key requirement of a cofounder is a persistence and dedication to do what is needed to be successful. That’s it. Finding out what’s most important to do, why, doing it when you need to and then getting to it is what seperates the brilliant software engineers with the next google under their hat that will never release, and the guys who focus on shipping.

You have to find what to do, how to do it well, and always remember why you are doing it that way.

If you don’t share the “why” with a cofounder and you cut corners where they want process, etc., you will be spending time dealing with each other than dealing with solving a problem.

When you have that, getting on the same page is one thing, but staying on the same page becomes something you can regularly review.  Sharing a passion and wanting to pursue it with equal dedication is critical to any startup.  If one founder is coasting or decides other priorities are taking precedent, it’s critical to look at what a person says, what they do, and what they say they do.

I’ll publish this for now and if I come up with more I’ll mark the title of this post as updated.