Running Around with a 25 Year Old CEO

I met Joanna Van Vleck, a 25 year old entrepreneur, a few months ago through mutual friends.

When you live in a small town like Bend, Oregon and you've been bitten by the Start Up bug, you end up running in the same circles with the other crazy people who are trying to change the world.

In this case, Joanna and I started running together, literally. But we say we're running "loops" instead of running in circles. Three mile loop? Four mile loop? Should we try the five mile loop on Saturday, just to see if we can do it?

So now we are running partners. We text each other to make sure the alarms have done their jobs at 5:30 a.m. It's harder to bail when you know someone else got up early for you, you better damn well show up.

Joanna and I push each other a bit: are you really sick, or should I go over there and kick your butt out of your warm bed? Yes, we have to go now, you know we won't go later. Let's just do it, we'll feel better all day if we run now. Yes we should do the hills, of course we hate them but we'll conquer them.

At first Joanna and I met each other over coffee and she asked me lots of questions about what I did, and wanted my opinions about sales and business and new ideas. I'm old enough to be her mother (if I had started young...ahem!) and was thrilled to think this fresh, smart kid with a brilliant business plan was seeking my advice.

As her business, The Trunk Club for Men started taking off at rocket speed, getting a coffee date with Joanna Van Vleck became nearly impossible, so we decided to start running instead. We meet at 6:00 a.m., the first appointment of the day. So far, so good.

I've said in the past that I like to run alone, and I still do, but it turns out running with Joanna works well for me. We run at the same pace, we both like to talk, we encourage each other, we're usually in good moods...I guess we are "morning" people.

So a funny thing happened during the miles and miles of conversations I was having with Joanna, week after week: it became quite clear to me that I was no longer mentoring Joanna, she was in fact, mentoring me.

When I throw out ideas about things I want to do, things I'm working on, or even kernels of ideas I might like to explore someday, she'll take them and run circles around them with me until the way to actually execute the thing becomes clear and visible. What about this? She'll say. Could you try it this way? Yes, you should do it, definitely!

Wow. I say. That's a great idea. Yes, I smile, that makes a lot of sense. Huh, I think, this kid is smart. Shit, I realize, if I had half her enthusiasm, her fearlessness, and her confidence to plow full stream ahead with a few of these ideas in this wacky economy, maybe I could stop worrying about playing it safe all the time, and just go for it.

A few weeks ago we had some major, unseasonable rainstorms here in Bend. Our usual running trails were flooded and soggy. We came to an underpass that was really a mess, and Joanna and I didn't want to run through two feet of water to get to the other side.

Huh, I said, I guess we can go back down the block and cross the street at the sidewalk. Joanna, who was in the middle of a great story about meeting a new VC, looked to where I was pointing, turned the other way, and started scrambling up the embankment to the other side, without missing a beat. I followed, of course.

I don't like running in soaking wet shoes and pants, but I don't mind a little mud, and her shortcut got us back on track quickly and efficiently.

I can't wait to see where this remarkable, talented young woman ends up in a couple of years, and I'm happy to keep running the trails with her, it I can keep up.