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Serial Entrepreneurs

Fred Wilson blogged about first-time vs serial entrepreneurs. As one of the latter, this was my comment: 

Fund them both.
I'm on my 4th company and 8th album. So I have a bit of an inside view. Passion is a lifelong thing, and the older you get, the better you are at harnessing it. 
There are a number of types of entrepreneurs and I'm going to guess it's different for different personality types. There's the steady, bright, business-oriented one; each of her companies will do well because she's committed to building great companies and is methodical in doing it. 

Then there's the one more like me--driven by passion and insights, tenacious, enthralled with solving problems for other people and trying to make big things happen. I'll throw ADD and hypomanic in there too; you learn to leverage it. 

By the 4th company, you've done, learned, and seen a lot. 

Like the replacement CEO who hits on the women in the office. The sales manager who refers applicants to his son's recruiting company for the commission. 

The amazing intern who cranked all weekend just to develop an analytics graphic that showed a major revenue opportunity. The deeply helpful friend who works with another friend's family to get him through depression. 

The woman whose son is busted for a parole violation and will now spend 3 years in prison unless she gets a real defense attorney. 

The models that you didn't think would work but then do. The ones you're sure about but don't. The product ethic you start the company with that people still follow and believe in. 

The customers who love everything you do, and the ones who complain all the time but never leave. The time you took your eye off the ball and everything fell apart. The time you held it all together with duct tape and hope. 

The day you inspired someone so much they begged to join the company. 

When we launched ChiliSoft, we didn't know what we didn't know. That's the biggest difference, I think. We were told we were inexperienced and just need to surround ourselves with the experienced. It turned out we already were doing the right things in just about everything but dev, which greatly improved with additional experienced engineers. 

A lot of building a startup is knowing when to stop researching and to start executing. It turns out, though, that most of us can figure it out along the way, and for the stuff we don't know, well we're tenacious enough to ask people who might have a clue, and then we dive in not knowing what's going to come of it. 

Part of our job is to bring light to the darkness around the edges, knowing there will always be more to learn and respond to down the road. 

I'm glad I have the experience now. My early team is made up of experienced developers simply because it makes it a hell of a lot easier to get to market and stability. But I look forward to the phase after launch, where we'll bring in recent college grads, train them and add them to the mix. 

After spending last week in the Valley, I can see why VCs love to invest in the energetic, exuberant (and irrational) first-time entrepreneur fresh out of business school. 

But I also see why Kevin Rose and other repeat founders get funded. The serial entrepreneur loves to win, hates to lose, loves to prove investors right and build great companies. 

And investors know that the downside is pretty much mitigated with a repeat winner at the helm, and the upside a lot more likely. 

My bet's on the serial entrepreneur :)


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