In the Startup World, They Say to Fail Fast…so I Listened

Here’s a great blog post called “Why I Quit My Job, Killed a Company in Six Weeks, and Still Feel Great!”. Well, you’re reading a similar post right now.

As you may know, I’ve been working on a startup called Dokkit. And as of yesterday, I’ve split up with my co-founders, only after a few months of working together. Wow, that was fast! Here’s what happened.

I thought of the idea for Dokkit about a year ago and fleshed it out.  I then started looking for some teammates to help build it. I attended startup events in DC, created profiles on entrepreneur matchmaking sites like, and just networked like hell.

Over the span of a couple of months, I found three developers who joined the team as co-founders, which was awesome, because the biggest hurdle for a non-technical entrepreneur is to find programmers to help build the product. We discussed the product strategy and they began developing. There were some debates about what technologies to use to build Dokkit, what the UX and UI should look like, and other important topics. We weren’t always on the same page about everything (which is completely fine), but the debating was enough for one of the developers to leave the team. I understood why and I moved on, continuing with the other two developers to build the product.

Then in July, I quit my job at the Washington Capitals to dedicate more time to Dokkit. Whoa! That doesn’t have too much to do with the story, but I think it adds some drama, right?

Anyway, a few weeks later, we performed a user test with about 70 people and got some great feedback. Unfortunately, that’s where our visions for Dokkit started to diverge. The team had some heated debates on what the purpose of Dokkit is, how the user would navigate through the application, and what the product would look like. I believed that our visions were too different to reconcile, and on a more personal level, I think the team just lacked cohesiveness and fit. Thus, I decided to leave, and the Dokkit team as we know it is no more.

Here’s what I learned from this:

-Move slow on some things, move fast on others – I should have moved a bit slower in forming the team. I wanted to build Dokkit quickly, so I recruited quickly and failed to take into account many of the “soft” factors, like cultural fit and alignment, that are so important in team-building. But I moved fast in leaving, which I think is a good thing. Maybe the team could have worked it out and become successful, but the signs were telling me to make a move.

-Seek advice from others who have been there – Before making a decision, I spoke with many entrepreneurs who have been through problems similar to what I faced. Their insight was absolutely crucial to my decision and I’m really grateful for their help.

-Failing feels oddly invigorating – Sure, I’ve failed before in my career, but in my mind (maybe not my bosses’), they were pretty small in the whole scheme of things. This is completely different since I’m on my own and the move has a big impact on my life. Nevertheless, I do feel great. I was definitely stressing out about the decision to leave, but now that it’s been made and I’ve “officially” failed, I feel kind of free and invigorated. It’s tough to describe.

The jury is still out on whether I’m going to continue to pursue Dokkit. I still love the idea, and regardless of the competition that has popped up in the past few months, I don’t think anyone has really figured out the smart social calendar space just yet. The funding world for consumer web apps has taken a turn for the worse, which of course will factor into my decision on what to pursue next. So as I consider what my next startup move is, I’m going to work on my consulting projects and continue to learn how to code.

So there’s the story of my first, and definitely not my last, startup failure. I failed fast but I think I failed right.

I know failure isn’t everyone’s favorite topic, but I think there’s so much to learn from it. I’d love to hear your thoughts about how you’ve failed, whether or not it had to do with a startup.

21 thoughts on “In the Startup World, They Say to Fail Fast…so I Listened

  1. Great read Mike! There’s no shame in learning from our experiences at all. Sometimes failure in business is direct & other times it’s an indirect experience. In your case I think you reached maximum growth potential with the project at this time. I salute you for realizing the team chemistry wasn’t there swiftly & cutting your loses. Keep your head up!

  2. It’s just a flavor of a pivot – you got more info and changed course – still a winning idea. Now’s the time to double-down and make it happen

  3. Wow this is a really inspirational story. I’m in hiring mode for Sharecro right now and I must admit i’ve been moving a little too fast. I’m going to slow it down a bit and take those “soft” factors you addressed like cultural fit and alignment into account for my startup! I would really like to get the chance to meetup with you sometime I’m free just about everyday after 3p.m. Just name the time and the place and i’m there.

  4. I blame Obama. In all seriousness, good luck with future endeavors. If you want, I’ll reach out to my cousin (not sure if he’s a developer but if not, he may know someone). Three caveats though. (1) he is terrible at responding. (2) he is based in Minnesota. (3) he likes the Red Sox and the Eagles. Let me know.

  5. don’t think of it as a failure. but as a learning experiences. it’s all about the take always- what did you learn. mistakes we won’t make again.

  6. I agree with your sister’s definition. I do not consider this as a failure. I find you very courageous to take the leap and am so proud of you. Not everyone can do what you did and I know that one day you will make it BIG!. So so proud of you, my favorite son!

  7. Failed is such a strong word. I don’t see this as a failure. It’s more of a shift in a different direction. Failure would have been building Dokkit, no one used it, it gets poor reviews, and it toilets down the drain. You made a choice and that decision will probably be one of the best you’ve made in your life. That probably explains why you feel so good….

  8. Nice post. Definitely sounds like the right call. I still love the concept – hopefully you’ll figure out a way to make it happen (or come up with something even cooler!)

    1. Yeah, I swung..and missed…but I still have two more strikes, right? Dokkit is still alive for now, but we’ll see what happens next! Thanks for the support and good seeing you last weekend.

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