Failed Startup Post-Mortems

This is an update to a post a wrote over 2 years ago

As we build our business(as) and lead our lives I strongly believe that

1. Life is a journey.

2. The best lessons (in business and life) come from mistakes made. It’s infinitely better when these mistakes aren’t ours but, as a mentor shared with me, ‘you learn from other people’s mistakes but you grow from yours’

3. It’s easier to course correct on the path to a mistake when you recognize patterns that look familiar to one you’ve seen before (or even read about). That’s why investment dollars tend to (rightly or wrongly) go to entrepreneurs who’ve done it before.

To the last two points above I decided to read some post mortems of failed startups. You learn so much more on what not to do from the story of Color than from the story of Facebook. At Power2Switch we make mistakes everyday. We just try not to make the same mistake twice. To avoid some of the mistakes we haven’t made (or even learn how we could have done things differently) I read up on some failed startup post-mortems and shared this with some friends a few months ago. Now I’m sharing 5 good post-mortems to help you course correct where you recognize some patterns. It’s helping us and I hope it helps you too…

Digging into ComEd's website

1. Best one in my humble opinion. Some of the examples he uses (e.g. Foursquare and Mayorship) might be dated but he still provides relevant thoughts about why his product (which is now taking off in other forms due to the progress of geo-location) failed:

2. Are you currently building that payment system from the ground up instead of just building on top of someone else’s API? Is the payment system your core competence? This post-mortem shares how this mistake was one of the main reasons why beat out Wesabe:

3. Good breakdown of the complexities of company structure that might lead to success or failure with particular focus on remote teams, product v business focus:

4. The one below is about dedicating the time and identifying the skills (like marketing) required to build a business:

5. This post-mortem (which can be considered a pre-mortem) is particularly fascinating because the business idea is essential Quora:

Bonus: for where your product doesn’t really address a need or satisfy a want. This story ends well because they learned from the data they had on the business and have built a business from it.

Hope this helps someone…


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  1. Ray says:

    Hi Seyi, thanks for sharing these. I’ve read the Devver one but not the others that you’ve shared. A while ago I built this website to capture all the failure stories and insights. Would love to share some of these with you:

    1. Seyi says:

      Will have to check out the site Ray, that looks like a solid collection of insights. Thanks for collating!