Startups - Plot your own downfall.

It goes without saying that you need optimism by the bucketload to create and maintain a startup. Having a discussion around failure almost seems redundant given the nature of the undertaking. It’s a constant heavy cloud looming just behind your shoulder that’ll suck you in if you turn around. (Perhaps that’s why it often weighs particularly heavy at night when your head is on the pillow; there’s no where for that cloud to hide.)

Most startups get up everyday and plow ahead with that always constant presence of failure simply accepted as part of the job. The downside to this approach is that it can hamper critical, nuanced thinking. Many failed startups are simply that; good teams trying all they can but having a critical foundational flaw that makes success impossible. However, many failed startups could have succeeded if they’d done more critical thinking along the way.

One exercise I like to do with Spreedly is to imagine our downfall. I recommend it as a team exercise amongst 3 or 4 founders or key employees if you get larger. Ask the group the following: “Imagine we’re sitting in this room in 6-12 months from today discussing shutting down our startup because we failed to raise (additional) funding. What reasons would we be pointing to if we were having this very real conversation?”

You’ll be surprised by the range of answers. Some of the best ones aren’t the big strategic “We found out the market wasn’t large enough” It’ll be real world concerns people are carrying with them but don’t always articulate. It might be news to you or things you never considered. Examples include:

Forcing people to really think about the end of their startup can have a chilling effect but one that then crystalizes the mind. The beauty is if you do this exercise early enough you then you aren’t actually about to fail; you’ll have plenty of time to act on the group sentiments that are reached. Lastly, doing this exercise once a month early on can act as a pressure valve to release a full range of concerns that might be simmering (or maybe festering is the better word) People now know once a month they’ll get the platform to discuss longer term concerns.

So go ahead, imagine your own demise! It’s cathartic.


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A successful pivot; lesson’s learned

It’s been eight months since Spreedly announced we were pivoting. Originally a digital subscription offering competing against the likes of Chargify and Recurly we decided instead to focus on being an online payment platform. We wanted... Continue →