Entrepreneur, Explorer, Angel.

Sometimes all at Once.

05TH September 2014


Losers & Lessons

Try again.

One thing I’m often told about investor decks is all the dead cats are left out. I just think that’s ridiculous, as they are more common- much more common- than winners in any direct angel portfolio. And they teach us the lessons that make the next one better… unless we ignore them. Here is my (admittedly) partial Wall of Shame. I’ll likely continue to add to it…

  1. TrustCloud went through many iterations of measuring trust and finally settled on selling warranties in peer transactions… like home repair, tutoring services, or anything where a few hundred to a few thousand dollars were at risk, and there was no “corporate office” to back up the transaction. Despite a beautiful product and some pilots with big names, it turned out a nice-to-have product in a nascent industry. An example of an Alt winner would be  AriBnB’s internal trust systems, which overcame the doubts people once had about peer-to-peer.
  2. WellAware’s vision was to consolidate health data in one place rather than disparate apps and devices for heart, diet, and exercise. As it were, it turned out a nice-to-have product in a nascent industry. An example of an Alt winner here would be Strava or Withings.
  3. Unibucks was founded to measure a “return” on tuition invested by mapping majors to job placements. While a huge problem, Unibucks suffered from being a very early solution and had too much product scope creep. Alt winner; None
  4. CellUFun was an early publisher of mobile games and did an admirable job of creating a community and currency. But, ultimately, making ad Sales as a single mobile media property is hard. Way hard. If there were an Alt Winner here it would be Rovio, who ended up with a movie for Angry Birds. But they are suffering too.
  5. M3 was a Mobile-based social check-in, which frankly was really cool and just ahead of it’s time. Wisely, we did it in London, which had a bit of an ecosystem to pull it off, but not enough alas. Alt Winners were eventually Foursquare, and of course Facebook.


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