Jan 15 2016

Running With The CEO

I’m a solo runner. While I regularly get asked to go on runs with other people, I almost always decline, as one of my great joys is to run alone.

There is one exception – I love to run with CEOs and founders of companies. There are some great stories about the outcomes from these, like my runs with TA McCann that resulted in our investment in Gist. I’ve run marathons with TA, Matt Blumberg (Return Path CEO), Matt Shobe (FeedBurner co-founder), Herb Morreale, and a bunch of people including my partners Jason and Ryan.

My favorites runs are the impromtu ones with CEOs like the one I did last night with Matthew Bellows (Yesware CEO). Earlier this week, Matthew sent me a note to see if I wanted to go for a run just before a dinner we were having together with Bart Lorang (FullContact CEO). My running goal this week is “three runs of any duration” and by Tuesday I knew the dates were going Thursday, Saturday, and Sunday. So I said yes and we scheduled it at 5pm – after my last meeting, but just before dinner at 6pm.

We met at my office at 5pm. The sun has gone down in Boulder by then at this time of year, but Matthew looked ready to go in his red running jacket and sweatpants. We walked down the stairs to Walnut and were blasted with a gust of cold wind. We headed up the Boulder Creek Path leading up to Canyon and out of town, straight into the cold wind.

We talked non-stop. He had a few things on his mind and I gave him feedback. As the minutes unfolded, I noticed I was doing a lot more talking as I told a few stories to underline my points, but it could have been that he was enjoying just plodding along at my slow pace, enjoying the run.

At the turn around point where the Creek Path starts really heading up the canyon, we stopped for a moment and looked around. Matthew has spent a lot of time in Boulder, including a two year period earlier in his life, and he emits the glow of someone who was touched by living here and always loves to be back.

The trip downhill with the wind at our backs felt a lot faster and before we knew it, we were back at my office. Matthew was going to head back to the hotel, shower, and change but I reminded him we were in Boulder so instead we just walked over to Bramble & Hare and hard dinner with Bart, which was awesome at many levels.

Matthew – thanks for another great CEO run!