A few years ago, Bessemer Venture Partners published 15 short stories about some great investments they could have and should have made, but didn’t.
The miss-histories behind Apple, Google, Zoom - and a dozen more startups they ought to have funded - were featured on a new "anti-portfolio" section of Bessemer's website.
It was hubristic. It was self-deprecating. And it was a wonderful humblebrag: Our deal flow is so amazing, these are the pitches we can afford to turn down.
Since then, surprisingly few VCs and angels have followed suit.
Well, here at Oughtfolio, we think you should.
Oughtfolio seeks to:
Collect and re-publish existing anti-portfolio stories.
Encourage investors to contribute new "oughta" stories.
Share your oughtfolio with the venture investment community.
Send your oughtas to:
matto@mattorochford.com
Stories we want:
“All I had to do was say Yes and write the check.”
Stories we don’t want:
“I knew a lady who knew a guy who said he might be able to get me into the round.”
At 58 years old, he coulda and shoulda been a success by now, angel-investing his zillions and zen-tweeting like a guru. In any case, Oughtfolio gives Matto an excuse to neglect his non-side project, That Mystery Startup.
He had the talent to become an NFL quarterback, or maybe even a television commentator, but instead Tony dedicated his life to the study of botched investment opportunities, and Regret Over Having Missed Out.
We didn't want to hijack the term anti-portfolio, so we created an alternative name.
Oughtfolio is a portmanteau of ought and portfolio, and a near-rhyme of the latter (especially here in Australia, where we couldn't be arsed pronouncing our Rs).
Your oughtfolio comprises the investments you ought to have in your portfolio, but don't. It's the opportunities you coulda, shoulda, but didn't invest in. It's not a wish list, it's the list of your screwups.
(And we love stories about screwups.)
Early supporters of Oughtfolio include:
Niki Scevak, Blackbird Ventures - @nikiscevak
Alan Jones, M8 Ventures - @bigyahu
Christoph Janz, Point Nine - @chrija
And of course, big ups to Bessemer for making the anti-portfolio a thing.
Oughtfolio has a sister site, Thoughtfolio, which collects the investment notes - aka deal memos - that VCs and angels sometimes publish about the venture bets they've actually made.
The misses are here, the got-ems are over there.