Good Judgement Comes from Experience; Experience Comes from Bad Judgement

Chip Wilson drops a knee on a fresh day in Floral Park, Berthoud Pass, Colorado, early ‘80s.

When I first moved to Colorado full-time, I got into a lot of trouble with Chip Wilson. We skied and climbed together all over the place in the early ’80s, and had just enough skill and more than enough drive to put ourselves where we never should have been.

In those days, I didn’t mind if someone climbed better than me and I didn’t mind if they skied better than me, but it pissed me off if they climbed and skied better than me.

Chip really pissed me off.

One day on Berthoud Pass, we made it up late on a spring powder day and went way out the ridge to South Chutes on Hidden Knoll, where Chip skied the year before. All the red flags were waving: a crappy snowpack, warming conditions, cracking and settlement everywhere. Chip pointed it down the line and made perfect turns to the bottom to wait for me.

I made my first turn off the top and the whole layer cut loose, sending me in a pile to the bottom, buried up to my waist. If the slide had stepped down, I might have been killed. Instead, I walked away and resolved to pay more attention the next time.

Chip and I stuck our necks out together on rock and on skis, learning the terrain and testing our limits. We came down the curve pretty fast, but in retrospect we’re both lucky to have survived.

The same is true of my experiences as a venture capitalist.

When Peter Roshko and I started out in our funds in the mid-’80s, there were about a dozen guys in the U.S. who knew what they were doing in the venture capital business: Frank Bonsal, Paul Ferri, and Tony Evnin on the East Coast; Tom Perkins, Don Valentine and Bill Davidow on the West, to name a few. Carl Carmen was the only guy in Boulder who got it in those days. Peter and I spent all of our time as young associates trying to learn how these successful VCs did their jobs.

What we discovered was that everyone was making it up as they went along. There was no rule book, no success model, no established regime that made being a journeyman VC a slam dunk.

Instead, we did our best to find experienced entrepreneurs with good ideas about how to build stuff for fast-growing tech markets, and pointed our hose full of other people’s money at them to help them grow. We stuck our necks out, backed some good companies, and surprisingly, didn’t get killed. The fact we both succeeded is a testament to luck as much as talent.

Peter and I have been partners for 22 years, a long time in the venture business. We’ve made more money together than we’ve lost, and we’ve learned a lot along the way about what to do and how to do it. Every once in a while, we’ll uncork a big one.

Chip has lived in Telluride for decades now and pours concrete at a profit. He still climbs a little, especially if it’s a desert tower with Crusher, and mostly rides around on his one wheel.

But when it snows, Chip Wilson will point his snowboard down the steepest line in Bear Creek and carve flawless turns in high-hazard terrain to the astonishment of the assembled youngsters.

Good judgment comes from experience.

James Dudley