Checking In On My Fantasy VC Portfolio From February 2014

I’ve been doing some updates to the good ol’ blog, and noticed a fun post from 2.5 years ago highlighting my picks at the time.

  • RelateIQ — I ended up investing in their Series C as a result of this post (their founder Steve Loughlin invested in Mattermark, and after 2 years at Salesforce he is now a partner at Accel Partners), and they were acquired by Salesforce 5 months later for $390 million.
  • Instacart — They were my Y Combinator batch-mates, and I still use them for all my grocery shopping. This pick seems super obvious now, but at the time they had only raised their Series A when I picked them.
  • Uber — I picked them because they were an early Twilio customer and I was already spending way too much on the service. This one was probably already obvious, but they had only raised $300M of funding at this point (versus > $15 BILLION now) so my fantasy portfolio definitely benefits!
  • Hired — I picked them because I love the founders, and my company has been a customer from the beginning and the service just gets better and better. They announced their $15M Series A just 6 weeks after this pick.
  • Digital Ocean — I originally picked them in June 2013 because I knew their bootstrap story and how loved they are in the developer community. They would announce their Series A shortly after my February 2014 post as well.
  • Product Hunt — I picked them because they reminded me of Referly and Launchgram, and Ryan Hoover has the X factor. They didn’t have any funding when I made this pick, and would announce their Seed round later that year.
  • Magisto — I picked them because I had recently paid for their mobile app, which I very rarely do. The company hasn’t announced more funding since then but remain among the top 10 grossing apps in the photo and video category in iTunes.

Funding Summary

Collectively, the companies in this list have raised $15.2 Billion in funding since this call… but obviously this is totally skewed by Uber. Excluding Uber, the other companies went from $65 million of collective funding to $609 million, and only 1 of them did not raise a follow-on round.

This is of course a fantasy fund, and if I were really trying to get results things like winning the deal would have to be factored in. But it’s still fun to see how these things play out… and important to remember these were not nearly so obvious (at least to me, maybe VCs disagree) at the time.

It was fun making this list, and exciting to follow along as these companies have grown and evolved over the past 2+ years. I can’t wait to see what they each do next! I love angel investing, and happily these days I’m putting my money where my mouth is.

Looking forward to putting out another list soon!




One Comment

  • Fabian Rausch


    I’ve been following your posts on Medium for quite some time and enjoy your quality writings and down-to-earth style.

    I am reaching out to you, in my role as a research fellow at HHL Leipzig Graduate School of Management, one of the leading business schools in Germany. Our team is looking into the relationship between VCs and entrepreneurs and how this relationship changes over time – often we observed conflict, which changed over the time – mostly when the founders became investors themselves. Since you are a perfect example of both, investor as well as entrepreneur, I was wondering if you’d be open to discuss some of our hypotheses.

    I’d be super happy if you just reply and give me a chance to show you some more information on what we are working.

    Have a great Sunday!
    Best regards,


    P.S. For your reading list, though I guess it must be seemingly endless, I highly recommend ‘The Industries of the Future’ by Alec Ross, former Senior Advisor for Innovation to the White House.

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