The Return of Random Day

I woke up late today (yay – 12:06 hours of sleep) to the last 15 minutes of the elite women in the NYC Marathon. Watching them finish and then watching Mutai crush the men’s field over the last six miles was pretty inspiring. I haven’t run a marathon since October 2012 when I ran the Detroit Marathon but after a year of struggling to get into a rhythm I’m once again motivated – and interested – in doing another marathon. I’ve committed to being one of the 14 in 2014 that run the Boston Marathon – there’s a gang of well known tech entrepreneurs and investors that are doing this together as part of a big fundraiser. I’ll definitely try to get at least one marathon in before then just to be confident that I’ll get it done.

Last week I added back in something I used to do regularly, but had stopped for a year or so given my schedule and then ensuing depression. I did a full day of random day meetings on halloween. I sat at Amante Coffee all day, mostly in my cookie monster outfit, had random meetings, drank coffee, and ate cookies. I had a blast.

If you’ve never heard of random day, I’ll meet with anyone who signs up for 20 minutes. I’ve been doing this for almost a decade – it’s part of my “give before you get” philosophy that’s deeply embedded in the Boulder Startup Community psyche. I have no expectation of what I’m going to get out of these meetings, but some pretty magical things, including the creation of Techstars, have occurred as a result of them.

During the course of the day I had 12 meetings, three cups of coffee, a yogurt, a burrito, and two cookies. I met with the following people.

  • Friend starting a COO / CEO search
  • Attorney in town thinking of starting a seed fund
  • Founder of a non-profit I recently supported
  • Person looking for a new BD gig
  • Founder of a natural foods company I just invested in
  • BD person looking to get into the VC or Boulder scene
  • Tech entrepreneur I hadn’t seen in a decade describing his new thing
  • Content marketing person looking to be plugged into Boulder
  • Founders of non-profit looking to expand outside of Boulder
  • Partners in a non-profit looking for support for a robot competition
  • New VC in town in the natural foods market
  • Two entrepreneurs just starting their tech business looking for feedback

I was immediately able to help at least six of the 12. I have no idea what will come from the other meetings, but that’s part of the fun of random day.

I plan to do this again six times in 2014. So that’s about 80 random meetings – people I wouldn’t have met with – and who wouldn’t have had some time with me. If one powerful thing comes out if it, then it’s worth it. Regardless, I had a good day on Thursday and feel like I did something that contributed to the glue in the Boulder Startup Community.

  • slacker.

  • John Fein

    That’s awesome Brad – sounds mutually rewarding. Also great to hear you’re running & supporting the Boston Marathon. Like many others, I have strong feeling about the marathon because it was a family tradition (grew up in Brookline). Would love to hear more about the 14 in 2014.

  • How do we get early wind of the dates?

    • I don’t publicize the dates – just email me if you want in on the next one.

  • Wait no picture of the Cookie Monster Costume?

  • The best part of this post? 12 hours of sleep. Jealous!! 😉

    • Yeah – I’m a major binge sleeper on the weekends. I had a 15:03 sleep a few weeks ago.

      • Wow – 15 hours. I also binge sleep on weekends, but I don’t seem to be able to sleep more than 9 hours these days. And I don’t get nearly enough sleep during the week, so this cycle likely doesn’t have a happy ending…. gotta figure something else out….

  • Christina Roberts

    Yes, but will there be costumes?

  • Would you ever do one of these in SF, Brad?

    • Maybe – good thought.

  • So key to building a community. Corporate types ought to do it five-six times a year. Wouldn’t it be cool for a CMO or CTO to randomly meet with anyone in the community?

    • Yes – very cool!

  • Walter

    Interesting-what type of natural food business did you invest in?

  • Jeffrey Hartmann

    So awesome to hear that you started doing these again. When you came to Oklahoma and described how Techstars came out of one of these meetings, I really thought the concept was really neat. I remember being really impressed with how you embraced a little randomness and chaos, and were richly rewarded and ended up creating something beautiful and enduring as a result. Viva dia randomico!

    • Thx! I have a lot of fun with them and am glad I’ve got the energy to do them again.

  • You mention natural foods twice in 12 meetings.

    There’s natural and nutritional as a broader scalable, now standard biz model (commerce/marketplaces). There’s natural that are carving the market up and haven’t figured out how to scale outside of franchises (non HPPd raw).

    Where your personal investment interest if you don’t mind sharing.

    • I’m doing some angel investments in natural foods. I can’t do them personally in tech because of my fund agreements, so natural foods it is.

      • Close to my heart.

        If there are criteria you are looking for or any syndicates of likeminded investors, let me know. is growing well and they are figuring out how to scale.

        Regardless–good on you for this!

  • Jeff Bodle

    I would suggest the nonprofit who is looking to expand outside of boulder keep their eye on as a possibility to scale to multiple cities assuming the nonprofit has showed considerable traction in boulder.

  • StevenHB

    Reminds me very much of this West Wing episode:

  • Rich Kwiat

    The open office days you and others like David Cohen had were clear indicators of how special this community was when I moved here nearly 5 years ago.

  • Vanessa Hurst

    This is excellent – I do a similar thing with Ohours in NYC and remote and really love it, but I don’t write about it or share the results often enough. Thanks for the reminder!

  • You helped a LOT, Cookie Monster….A little something is coming from – A Pittsburgh Thing…..

    • Cookie cookie cookie!

  • Matt Candler


    This was one of the things I loved about your approach when I first started following what/how you do. So psyched it’s back on the list.

  • That’s an awesome idea! Where do I sign up for this? Haha