Crazy? Awesome? or crazyawesome?

Only time will tell.

Most startups wait until right before–or even after–they run out of money to finally answer the question, “How are we going to make enough money for this to be self-sustaining?” At clippPR we wanted to solve this problem before the runway ends. But, pretending like there is no more money in the bank is nearly impossible unless you create an environment that feels almost as desperate.

So, we decided to ship as many revenue generating features and products as humanly possible, by doing seven 52 hour hackathons in one month.

A couple random details before I describe our process:

  • In case it needs to be said, this is an insane schedule for a very specific amount of time, we normally have a more sustainable schedule. But, sometimes, startups have to do things that aren’t sustainable.
  • This obviously doesn’t leave much time for test coverage, scaling, or refactoring. But, sometimes, startups have to do things that don’t scale.
  • One of the reasons we can do this right now is because the main product has high test coverage, and is built on top of a solid internal API. And, sometimes, startups have to do things that are crazy and fun.

So, the process:

  • find things that have immediate revenue attached
  • cherry pick low hanging fruit
  • validate quickly
  • and show off progress

We started by reviewing all the feedback and insights we captured through our customer development and ongoing conversations with existing customers. (I can write more about that if you like?) At the end of that process we had collated and refined a clean list of five things our customers and potential customers would say to, “clippPR is good and I like it. But, if you could just __________ it would be great and I couldn’t live without it. Please take my money.”

Then we did a massive dump and sort of all the ideas we could imagine would solve those problems. Everyone had 10 minutes to fill as many post-it notes as possible with their ideas. Then we threw them all on the white board and stacked up the notes that were the same. Then we grouped similar solutions into little piles. Then we pulled off all the piles that couldn’t produce real revenue within three months, to save for later. We were left with 29 piles, and gave each one a product/feature name.

Next, we created a quadrant with an x-axis of estimated time required to build and a y-axis of amount of estimated revenue within 3 months, and plotted out all the ideas. So, the ideas that have the highest potential revenue but shortest amount of time to build were in the top right, and the ideas with the lowest potential revenue but longest amount of time to build were in the bottom left.

The scary part was looking at the calendar. Our hackathons would start at 11am the first day and finish at 5pm on the third day. We needed a FULL day off after each hackathon to catch up on sleep and get a little break from one another, and we would need a recovery day for any bug fixes, integration with the live product, and deploying. We ended up with 7 slots. We filled in the slots with the low-hanging-fruit first, and then added the bigger projects last.

My wife made a quick run to costco to pick up some hackathon vittles, I invited some folks to our first demo night, and then we got started.

I am writing this on the second morning of our third hackathon, so I’ll save the review for the very end. But, I can tell you a few things:

  • We’ve already shipped 5 new features/products to live, and it feels amazing. There is something inspiring and motivating and very tangible about shipping so much new stuff.
  • Most of these shipped around Thanksgiving, so I don’t really get to start showing everything off to the larger group of customers until next week. But, the alpha testers who have already seen things and helped test during the hackathons are really excited.
  • I work with an amazing team who can do magic.

Update: Zack Miller asked a great question that made me realize I left out a very important point: The value is not so much about getting no sleep, and more about having a single focus and purpose for the entire team, all-hands-on-deck solving one specific problem, and having the time constraints to force us to ship the first version of things that actually work.





14 responses to “Crazy? Awesome? or crazyawesome?”

  1. thomasknoll Avatar

    I’m curious to hear whether any of my friends have tried something like this?

    1. Jicknones Avatar


      My mentor Mark Zweig was my favorite college professor + first employer( After working at his company for a few months, I decided it wasn’t for me so I chose to go FT in my hobby business, Lavish Longboards. He told me–If I quit, I would have to promise him that I could commit 12+ hours a day for 30 straight days. No days off…

      Worked great(I do it once a quarter now), and I’m happy I put myself through it. Startupbus is also a really good example of this, it was really fun and it changed my view of *real* productivity. Get idea > build product > validate. All in 72 hours!

      You rock TK, thanks for sharing!!!!

      1. thomasknoll Avatar

        Sounds like an amazing mentor. I still haven’t done a startupbus yet, but they do sounds fun!

        1. Jicknones Avatar

          He’s pretty awesome, taught me a lot! He’s a pretty active twitter-errr too(

          Also, startupbus in insane, and awesome, or insanelyawesome. You should get with your LV crew and pitch Elias on a Las Vegas Bus for the next ride in March!

  2. Zack Miller Avatar

    I have a hard time recovering from these once every six months, not sure how I’d do with 7. Are you sleeping or going straight through?

    1. thomasknoll Avatar

      Definitely getting some sleep. Though, I’ve always gotten about 6 or 7 hours per-night at startupweekends as well. Do you usually skip sleep during SW @zack_miller:disqus?

      It’s not so much about getting no sleep, and more about having a single focus and purpose for the entire team, all-hands-on-deck solving one specific problem, and having the time constraints to force us to ship the first version of something that actually works.

      1. Zack Miller Avatar

        I usually get home around 1am and wake up around 5-530am for the next day. The joys of an organizer!

        Personally, I tend to get my most effective work done from 6am-10am before most get to the office. 🙂

        1. thomasknoll Avatar

          Ah.. good point! I’ve never been an organizer. I imagine that would be *super* draining (and rewarding).

          1. Zack Miller Avatar

            I was thinking yesterday how crazy different it would be to participate rather than organize or mentor.

  3. Karen Hartline Avatar

    I’ve never done a Hackathon but love the idea of changing focus, pushing the team to contribute and decide what features should be added (now or later), listening to your customers, and making things happen. Thinking about how I can do something similar with my team, mostly to stretch them a bit!

    1. thomasknoll Avatar

      Could be interesting. Trying to imagine what that would look like for event production… maybe enhancing some of the offerings, or workflows, or building a system for sponsorships, or…?

  4. Jimmy Jacobson Avatar
    Jimmy Jacobson

    Can you post the dates of your next Hackathons? Wedgies is in.

    1. thomasknoll Avatar

      We’d LOVE to have you join!

      * 11am 12/4 to 5pm 12/6 – Demo at 5pm
      * 11am 12/9 to 5pm 12/11 – Demo at 5pm
      * 11am 12/14 to 5pm 12/16 – Demo at 5pm
      * 11am 12/19 to 5pm 12/21 – Demo at 5pm

    2. thomasknoll Avatar

      When are y’all joining!?

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