My fellow VCs tease me about how impressive my anti-portfolio is. In the spirit of the transparency in venture capital that I advocate, here is a list of the deals I missed that have since achieved some form of liquidity event for their investors and thus can tangibly prove that I blew it. In all cases, I had the opportunity to invest in these companies, but for one reason or another, did not execute. Sometimes I didn’t see the potential. On other occasions, I failed to convince my senior partners or my investment committee. My main objective in acknowledging this anti-portfolio is to challenge myself to build a track record of actual exits that exceeds my anti-portfolio’s performance.

Clear2Pay – Michel Akkermans and Jurgen Ingels having already brought their company to a multi-million euro revenue stage with ambition to reach the hundreds of millions, C2Pay was one of the first deals I worked on during my tenure at Truffle. We could have invested in 2006 if we met their valuation expectations. We were penny-wise and pound-foolish. Acquired by FIS in Oct 2014 for 375M€.

Quintiq – Dr. Victor Allis was quietly building the next generation supply chain software company in the middle of nowhere in southern Holland. He had his pick of top investors for growth equity. This one stings a lot because I miraculously found a way to get us on the short list. But I couldn’t bring it over the line. Acquired by Dassault Systèmes in Sep 2014 for 250M€.

ConcoursMania – I liked Julien Parrou the minute I met him and my gut was that he would go on to build a great company from his early-stage initiative in sweepstakes and gaming media. I should have listened to my gut. IPO on Euronext in May 2011. Market cap today: 36M€. I reckon that we missed out on a 6x multiple.

Nedstat – This Dutch web analytics company was only seeking a few million euros to top up its Series C before being acquired by comScore in the U.S. for $37M. We missed out on what would have been a modest multiple but a fantastic IRR.

X-Hive – A chance to make a second Rotterdam investment within a few months of my first. The plucky founders pitched us on their “content component management database.” We didn’t get it. In contrast, global powerhouse EMC “got it,” acquiring X-Hive six months later for significantly more than the valuation at which we could have invested.

PINS – A Dutch build-up in the hosting space. I was extended the opportunity to co-invest with a trusted Benelux team. I demurred. I was wrong, missing out on a potential 2x return in a later transaction.

Capptain – I liked the native app analytics space, and Capptain came to my attention from a delighted customer of the tool, which is one of my favorite deal sourcing methods. A classic example of how our multi-million revenue threshhold filtered out an early-stage winner in a high-velocity space. Acquired by Microsoft in May 2014.

Mesagraph – In 2012 my intern at the time introduced me to the CEO of this social TV analytics startup. Two years later, Mesagraph is acquired by Twitter. Note to self: pay more attention to my interns.

Bibit – the only one on this list from my previous fund before joining Truffle, this Dutch online merchant card payments processor seduced us along with many other VCs. Unfortunately, I couldn’t match the terms, and missed out on the successful exit to Royal Bank of Scotland. Furthermore, Bibit founders Pieter van der Does and Roelant Prins went on to create Adyen, one of Europe’s rare unicorns.

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