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!

  • wld love to get you out on the trails on a dirt bike.

    I know your position on bikes, but properly geared up this can be tremendous – and safe – fun.

  • This is so cool, Brad.

    Aside from the many benefits of running together, one of the things I love the most about such a “thing” is that it becomes a tradition of sorts. And, traditions become great memories.

    Yes, it is likely we’ll remember that amazing meeting at Starbucks or Peets. But, so much more likely we’ll remember that run as something special.

  • Dariel Luciano

    “I’m wasted on cross country. We dwarves are natural sprinters.”
    – Gimli, son of Gloin

  • Joah Spearman

    Love it! Next time I’m in Boulder, I’ll have to drop you a note. I almost always run alone too, running and writing are two of the only things I get to do on my own time that doesn’t involve external pressure.

  • If you make it out to the East Coast Brad try running with one my fav runners & our first NetSuite client, Danny @, as he is a lone runner too:)


  • Steve Jobs used to like to go for walks and talk. I love that too. Walking along the lake talking to someone is as close to nature as you will get in the big city, but people tend to loosen up when they are in a spot like that.

    • I’m also a big walker. I love walking meetings.

  • “…and he emits the glow of someone who was touched by living here”

    I’d love to glow like that. I can assure you that there’s no such thing as “the Toronto glow”, LOL!

  • Slence is equally welcome in a walk which is considered abrupt or itching during table (coffee or conference) meetings.