Good Deals that Don’t Work

Good deals that don’t work…

About 6 years ago, I did a great deal. I went in with Seqouia.  I then did a follow on round in the same company with Redpoint and USVP.  The management team stuck together, the team sold alot of software to GE and other brand name companies.  The software delivered an ROI.

6 years later, zero.

I did not get my money back and neither did all the big firms who I invested with.  These are the ones that I had to loose on.  All the arrows pointed right all the way along.  They did take on venture debt and that really cost them in the end when it removed thier flexibility.   They were picked up by a group who seems to be rolling up enterprise software startups, but after the debt was paid, nothing.

I am sure this will come back to bite me, but this is officially my last pure venture investment in a enterprise application start up.  If this team could not pull it off in this area, I just don’t think the risk/reward works.

About Ben T. Smith, IV

Founder of, investor in and advisor to technology and media companies
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