To Partner or Not Partner?

Talked to an old friend of mine yesterday. One of my best friends, we've known each other since the 6th grade. We started the same new school that year, and from then on people always got us confused for each other. Our paths split and merged a couple times during the next ten years, and it's cool that we are still friends after all these years.

Kevin is like a kindred spirit. He has the same quirky, dorky sense of humor. He has the same entrepreneurial spirit about him. Matter of fact, a few years ago we briefly started a business together that turned out to be a great idea, just a decade or so too early.

I hadn't talked to Kevin in a while, and catching up I found that he's still got a fire burning inside him to run his own business, be his own boss, do his own thing. During a recent business trip for his day job, he had lunched with a very, VERY successful business man to try to gain his business. Kevin asked the guy how he started his business and the guy said it was basically him and a friend and they just got along so good together they felt like they had to find a way to do something together. Lucky for them after many years of hard work it's made its way into a $70M business.

Kevin and I are like brothers. When we get together, we are instantly taken back to 6th grade. Matter of fact, when attending college together, numerous times we walked the line of getting throw out of class by our professors because we just couldn't settle down. Lucky for us there were just as many times when we would put our energies to creative mastery, as to professorial torture. They loved to hate us, or hated to love us. Sometimes both.

So Kevin throws out that it might be interesting for us to try and start a business again. Kinda like picking up where we left off, only a few years later. But I had to be honest, so I told him I just wasn't in that space anymore. I've seen the sacrifice/money it takes to cultivate a good idea into a profitable company, and I'm just not ready to make that sacrifice or incur that cost.

What did pop in my mind though, was how great Kevin and I would be writing together. Kevin and my imaginations, when combined, could be described as Farrelly Brothers or Wayans Brothers'ish. We're silly. Just plain goofy. And we snowball off each other like crazy.

But Kevin wasn't so sure about it. He used to write in high school. And he was a very imaginative writer. But he hasn't written since. And as he himself said, "if you don't use a gift, you lose it, and I think I've lost that ability."

To be even more honest, I'm not sure if I'd want a partner. I know one of the pros is that you stick to a schedule and you have someone pushing you and all that. But the con of creative differences and scheduling around someone else might not be very fun.

Anyone out there have an experience with working a partner? Pros, cons?

I'd have to sell him on investing his time in a new arena he's never considered before. (ie. scriptwriting) But I think if he bought in we could write something special together, even if it was us brainstorming together and me going and writing it.