Plummet At The Summit: The Very Unofficial WDS Skydive Adventure

The Very Unofficial WDS Skydive Adventure

When I announced back in January my crazy idea to jump out of a plane at the World Domination Summit in Portland, I only knew one person that was going to go. Me. I thought I would get some interest via the blog, but figured that I might be able to get 10-15 people to sign up and come with me. That would be a very manageable amount of people and after all, I was asking people to spend $200 to to fall 13,000 feet to their sudden death with me so I was tempering my expectations. I thought it would be cool if I had a bunch of people join me, but I knew that one way or another, I was going to cross skydiving off the impossible list during my weekend in portland.

I posted the piece and got about the level of interest that I expected; 10-15 people gave me verbal commitments. I was pretty happy with that number and knew I could take more, but I let things go. No need to overcrowd the adventure. The next week or so, I woke up one morning and saw an email from Chris Guillebeau about WDS in my inbox where he mentioned that I was taking a bunch of people on a very unofficial skydiving adventure. I went to check my sign up page and all of a sudden I have a 63 people signed up on the interest form.

I just sat there for a bit. I was happy for about 15 seconds, then I realized…I am so screwed.

How am i supposed to organize 63 people jumping out of a plane? In Portland? 2,000 miles away and nobody that lives there drives cars!

I was stunned. Chris sent me a message on twitter.

“How many people are signed up for the skydive trip?

“Um…a lot…63 I think???”

He responded in a way on Chris could saying “Yea, you might want to put a cap on it.”

Good Idea.

So I closed registration and just sat there for a couple weeks. Not quite sure what to do. I had never been skydiving before, never been to portland before and never actually even contacted the skydiving place before I posted that post. Would they even be able to have 63 people jump in a day? Now I was planning to do all three and take 60 people along with me. Stupid, stupid, stupid.

After a couple weeks of not knowing what to do, I finally decided I could either sit there or adapt and do something about it. Things don’t always turn out how you plan, but you always have the ability to adapt and react as things change around you. So I decided to do something about it.

Over the next month and a half, I made a bunch of phone calls, collected deposits (which brought the total number down to a “manageable” 40) and checked incessantly.

Pro Tip: When organizing something like this, always collect money early on. Asking for money separates people who are really interested from the people who like the idea, but not enough to commit to it with their own money. If you have a large number of people you’re working with, this helps narrow the field considerably (in my case, 63 people turned out to be about 40).

The reputation of the Pacific Northwest’s weather preceded my itself and up until 3 days before the jump, we thought it was likely going to rain and ruin the whole day (Chris even renamed the opening ceremonies the H20pening cermonies just in case that happened). Once again, I remembered that you always get to choose your attitude, so I told people that we would be going to the jump zone one way or another, rain or shine and let the staff at the jump zone tell us if the weather was so bad that they were going to turn down $10,000 of our money keep us on the ground.

Jump day finally came and the day went amazingly well. The 40 people that committed to jumping were all amazing, incredibly flexible people. The small group of drivers I had, turned into a small army of volunteering chauffers (in Portand of all places!).

We arrived at the jump zone at 10am and spent the first hour and a half or so filling out paperwork. If you’ve never been skydiving before, you have to sign waivers that basically say, you’re jumping out of a plane and it’s not their fault if the parachute doesn’t open.

That’s reassuring.

They started funneling us into training, 12 at a time and jumping 6-8 people at a time. The jumpers all landed in the field right in front of the office building where everyone was waiting, so everyone got to see everyone jump. The day lasted a good 6-7 hours. We started at 10 and the last jumpers ended around 5pm, but everyone still got back in time to shower and get ready for the main event. Success! Oh, and we had blue skies and warm temperatures all day. The staff at the jump zone even mentioned that it was the best weather they’ve had all season. Take that Pacific Northwest weather!

Besides being a lot of fun, the skydive was a great way to start off the weekend. In a way it was sort of a pre-kickoff event kickoff. Several people knew each other from twitter handles and gravatars and a few people had actually met in real life. There were a lot of new faces meeting new faces on a much more personal scale than later on in the conference crowds where there were 500 people. Also, you tend to bond with people in a much more intimate way when you’re facing a fear together than when you’re sharing a drink with them. If you want to get to know someone well, jump out of a plane with them. It’s very telling and an experience you’ll be able to look back on together as a shared experience.

A lot of people asked me if I marked anything up or made any money off of this, and the answer is no. I probably could have based on the time committment required, but this was more about the experience than the money. If money was the end goal, it certainly could have been made, but I enjoyed organizing an event where people get to stare fear in the face and walk away victorious. I had a lot of people come up to me and say “I wouldn’t have jumped if there weren’t 40 other people coming with me.” I’m not sure what that is worth, but it’s worth at least a few bucks for sure. I’ve been asked if I’m going to do this again next year, and I’m not sure. It was a lot of work and it was certainly worth it to see almost 10% of the WDS attendees to come to an event I organized on a whim, but I’m all about originality so we might have to find a new out-of-the-box activity to do (extreme ironing anyone?).

One key leadership takeaway from this whole adventure: If there’s something you want to do, don’t ask others if they like your idea. If you really want to do something, just do it. Invite other people to come along if they want, but do what you want because you want to do it. I was going skydiving in Portland no matter what. It was happening whether 4 or 40 people were coming along with me. That attitude refelcted itself in everything down to the title of my announcement post. The title of my post was “I’m Jumping Out of a Plane at WDS, Who’s Coming With Me?” The turnout for the jump would have been a lot different if I would have asked “Does anyone want to jump out of a plane with me when we’re all in Portland together? Please?” Based on past experience, If I would have approached this adventure like that, in return, I would have gotten a mixed reactions, a few half-hearted commitments and a lot of flakes who didn’t turn out. Instead I created my own adventure, got excited about it and then invited people into it. People are looking for adventures to join up with. Go and create one and ask them to be a part of it. They’re waiting.


Videos and photos of the whole adventure are available on flickr. Big thanks to Dave, Mark, Justin, Brandon and Kohan for taking these shots. Feel free to use any of this media as you like (added bonus if you’re nice and give credit where it’s due) –> Very Unofficial WDS Skydive Adventure.


I have video & photos of my falling out of the plane and looking like an idiot. If you can’t wait to see me make awkward faces and look stupid, stay tuned. I’m still waiting on the video, but the previews I’m gotten from the photos mean you’re probably in for a few good laughs.


A group of us went bungee jumping the Monday following the conference as well (we were on an adrenaline spree and I had been drinking a lot of Red Bull). That post recap (complete with photos as well) is coming soon.


Several jumpers were asking me who jumped and looking for a way to keep in touch with each other. Here’s an semi-exhaustive list of the jumpers, their twitter handles. If one of them is wrong, or if by some chance, I missed someone (I don’t have last names of people that paid in groups), let me know.

  1. Jonathan Woodrusch
  2. Jenny Leonard
  3. Jacob Sokol
  4. Molly Mahar
  5. Nicky Hajal
  6. Mike (Tumble Design)
  7. Nick Laborde
  8. Bryce Longton
  9. Andreas Nicholas
  10. Mikell Beechinor
  11. Mikell Beechinor’s Friend
  12. Dave Ursillo
  13. Brenda Joy Sesto
  14. Brandon Sutton
  15. Agnes Constantino
  16. Rex Kinnison
  17. Rex Kinnision’s Wife
  18. Satya Colombo
  19. Lenay Snyder
  20. Nathan Agin
  21. Nina Yau
  22. Jeanie Witcraft
  23. Tessa Zeng
  24. Steve Kamb
  25. Mark Powers
  26. Steve Schob
  27. Matthew Madeiro
  28. David Damron
  29. Alan Perlman
  30. Matt Gartland
  31. Michael Hrostoski
  32. Kohan Ikin
  33. Matt Bailey
  34. Karla (Matt Bailey’s Girlfriend)
  35. Chantelle Baxter
  36. JD Roth
  37. Kris (JD’s Wife)
  38. Jed Bickford
  39. Danae Ellison
  40. Justin Runyon
  41. Joel Runyon (Me)

If you get a chance, you should probably check out these daredevils.


The alternative post title that got left on the editing floor was “How to get 42 people you’ve never met before to jump out of a plane together while somehow arranging transportation for them all to get an hour outside of a city ghat doesn’t believe in cars without using public transportation.” It’s too bad, I would have totally dominated that long-tail keyword phrase on google but hat tip to JD Roth for the new & much improved title.

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  1. Mikell says

    Was definitely an epic day. Thanks for bringing everyone together. It was a great way to start the WDS weekend, meet some awesome people, and kick fear in the teeth. :)

    You can add my twitter handle to the list if you’d like: MikellSloan.

  2. says


    “If there’s something you want to do, don’t ask others if they like your idea. If you really want to do something, just do it.”

    No approval required. Great advice Joel!

  3. says

    Awesome post – thanks for putting this whole thing together! Like you, I was hawking in the days leading up to it, and thankfully we were all wrong about the weather. I look back on that day as one of my favorite days ever! It was my third jump, and by far the best of the 3. Perfect in every way.

    Thanks again, Joel! You’re awesome for facilitating this. It’s an experience I’ll never forget. :)

  4. says

    It’s great you did it and you make a lot of them happy.
    This is last what I read before I go to sleep, and it make a big smile on my face,thx for that:)
    Propobly I will dream about jumping from the plane(it’s for a long time on my list of imposible tings) 😉
    Flickr ,I’ll visit tomorrow.
    You did great job Joel! Bravo :)
    P.S. I’m sure you did enjoy all.

  5. says

    Great post. Not sure this is one adventure I could ever manage. Pretty severe fear of heights- but I am inspired to think about it! lol

    • says

      Once you’re up there, you don’t have much control. The tandem instructor decides you’re jumping and you jump. Quick way to force yourself to get over your fear of heights quick :)

  6. says

    Wow. That is f*cking awesome, and I love the message – the power of suggestion, “I’m doing this, who’s in?”.

    I went skydiving in Namibia last year and couldn’t wipe the grin off my face for a whole week. I would have chickened out too if there weren’t other people I knew going – it made a huge difference having the support of the group.

    I REALLY want to go to WDS one day. Pity Australia is so far away from Portland, but I’ll try to travel-hack my way there on year 😉

    • says

      You can figure it out. DO IT! :).

      I find the best way to get people to join you is to jump in and do it anyways. Once people see you’re committed, they’re usually not too far behind.


  1. […] Organizing a skydiving adventure 45 minutes outside a city you’ve never been, from halfway across the country is no small task, but somehow it all went off without a hitch. 41 people did something impossible, faced their fears and most importantly – NO ONE DIED. That’s a win, if I’ve ever heard of one (even if my  jump did make me look completely stupid). […]

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