A catch phrase will go here soon.

The ultimate cure for startup stress


Last night Mike Arrington, Brian Sugar, and Heather Harde hosted 2,000 of their friends at an epic party in Hollywood. I haven’t seen this level of party since Silicon Alley Reporter threw the blow out bash at the Chelsea Piers. Toward the end of the night I grabbed Arrington and threw him in my car–he was exhausted in the best way. The way someone who’s accomplished great things feels when the last page of the script is done, the clock hits zero and the buzzer sounds, or the fork drops on the clean plate. Another masterful performance, more drama added to the legend of a brand he’s built, and it’s time to celebrate.*

We headed over to Mike’s hotel, and along with my wife, Loren Feldman, Scott from ThisNext, Brooke from MySpace, and Tyler from Mahalo settled in for a great meal. No stress, lots of laughing, good food, and big smiles when the digital cameras popped out.

Which lead me to realize what the greatest tool for managing stress in the world is: your friends. Fred Wilson point this out in the comments of my last post on “death by blogging/stress,” so it was brewing in the back of my head and last night confirmed it.

Here are examples of ways in which I’ve found to release stress with my friends:

  • a) My pal Matt and I play basketball in my driveway on the weekends. We talk business, we talk personal life, he tries to break my nose… all kinds of good stuff. Friendship, competition, exercise, and sharing some common experiences (we’re both 30 something entrepreneurs who’ve lived through two cycles).
  • b) Since I like to get into work late (11/11:30AM) and work until 8 or 9pm I sometimes walk around the office and pick a couple of folks and say “want to grab some supper.” Supper is different than dinner, it’s later and less formal. It remind me of Barcelona, perhaps my favorite city that I haven’t lived in. Everyone’s gotta eat, and late night meals are the best. I’ve been doing this since my New York days.
  • c) We put a basketball hoop in the backyard at Mahalo. Folks play HORSE. See (a)
  • d) “walk and talks” -many times I’ll grab folks at the office and say “let’s walk and talk.” It’s a mafia reference for when folks were being tapped they would walk the streets so folks couldn’t listen in. A walk and talk works for getting you out of your headspace.
  • e) See a show. I know, I know… you guys are starting to wonder about me, but I love me some Broadway. When I got to New York City now I just buy tickets to whatever the best rated show of the last 2-3 years and go. Great for starting conversations and getting out of your skull
  • f) Poker: Love it. Get a game together with some friends, buy chips, buy beer, sit by the pool or in your apartment and have some fun. Playing games with friends is something we stop doing as we get older and its a real shame. Sky Dayton, Bill Gurley, Stuart Aslop, and Jim Lanzone and I had a great poker game at the WSJ D conference last year. We’re doing it again this year.
  • g) next time you go to a conference fly there with someone. Mike Arrington, Om Malik and I were all on the same flight to Le Web this past year. It’s just great fun to travel together, share movies, and read books.
  • h) Host dinner parties for your friends. John Brockman and Katinka Madson of Edge.org and Brockman Inc. would have me over their house for dinner for years when I was a broke kid. When they come to LA now I host “Brockman in Brentwood” dinners (we’ve had two so far) and I pull out all the stops. We take pictures and have fun with the menu. It’s a great milestone in our lives.
  • i) My friends who I don’t see much like Mark Cuban and Ted Leonsis send each other funny, quick emails. Just little pickme ups. My favorite time to send people emails is when they are getting their ass kicked. If something bad happens that’s when your friends NEED to hear from you most. The second a playoff series ends for Mark or Ted’s teams I always send them a note–good or bad. We all lose sometimes, and it’s great to get a little “i feel your pain pal” emails. Highly recommend reaching out to friends when their down.
  • j) When you’re stuck in traffic open your address book and look at the names. Pick one that you haven’t talked in a year and call them. Tell them it’s been too long and you wanted to hear how their doing. It’s amazing when you get a call from an old friend–it’s magic.

You get the idea. Build events around your friends, play games with them, and cherish your time because its all you’ve got.

I’m still the most rabid entrepreneur you’ll ever meet. I still work seven days a week, and I still want to destroy any problem, competitor, or market force that stands in my way. You can be a killer and a workaholic but still have an epic life: you guys have to design it that way.

That’s the lesson in all of this: we’ve got an amazing community in the tech industry filled with amazing people. We’ve all developed friendships over the years–try developing them some more. Take a casual friendship to the friendship level, take a friendship to a deep friendship level.

Email that person you’ve had two or three conversations with and ask them to supper or to for a walkntalk. Let the stress out with play, talking, and good cheer. It works.

Next rounds is on me… pal.

* Celebrate: that’s really great word. Try to celebrate the little victories. That’s another technique of mine… I’ll do another blog post on that some day. (or chapter in the book… oh, did I mention the book?).

And now… some photos with friends I randomly snipped from the web:

  • DJ Burdick

    Thanks for the post! Good stuff. Celebrating the little
    victories is important. They’re especially easy to brush off.

English Bulldog

Hello, my name is Jason. Welcome to my blog on the interwebs. You can reach me on twitter @jason and by email at jason@inside.com. My Skype is jasoncalacanis, and my mobile phone is 310-456-4900.

I only pick up numbers I recognize, and in terms of emailing me, the best strategy is to write short, blunt and to the point requests. I can quickly respond to short messages, and many times I simply don't have the time to read five page pitches. In terms of taking meetings, I only do that after reviewing an actual product (not a business plan). So, the best time to ping me is when you have mockups or an alpha site. I don't read business plans, and I've never written one.

Other twitter accounts you can follow: Inside.com, Ticker, This Week in Startups and LAUNCH Festival