“The Best Breakup Ever”

Ajay Chopra
Trinity Ventures
Published in
3 min readJun 8, 2015


I recently learnt that an entrepreneur I had turned down wrote an email to one of his existing investors describing our parting of way as “the best breakup ever”. Frankly, I was already having angst about my decision to not invest in this company, so this entrepreneur’s generosity in characterizing our “break up” only increased that angst. However, this made me reflect on the fact that we as VCs spend a lot of our time turning down high quality people for one reason or another. As an example, here at Trinity we see over 2000 companies a year and end up investing in only about 15– including our seed investments! This means we turn down 99% of the companies we meet. More importantly, we turn down 99% of the people we meet during these meetings. Of course we make many mistakes in our selection process. Many times we invest in companies that end up going bust — what VCs call Type 1 errors; other times we do not invest in companies that end up being blockbusters — what VCs call Type 2 errors. I have a list of my Type 2 errors on a piece of paper lying front and center on my desk. It reminds me of how wrong I can be in my judgment.

Which leads to why it is so important for VCs to be honest, fair and upfront with the 99% of the entrepreneurs who they happen to turn down. Besides that fact that all people deserve to be treated with respect and honesty, it just makes good business sense for all sides that VCs treat their turn-downs with the same care as the companies that they select. The fact is that the VC business is a people business, not a “deal” business.

Having been an entrepreneur myself in the past, I clearly remember the good turn downs from the bad ones… and the really bad ones, where there was no response at all. I was always mindful of the VCs who treated me with respect while turning me down and was inclined to reach out to them as my business evolved. Conversely, I had no inclination to stay in touch with VCs that were condescending or evasive.

As a VC, I am far from perfect with my turndowns, but these are the rules I strive for when turning down a company:

— Be clear. Form a clear reasoning why the investment is not right for our firm at this time. Articulate this honestly to the entrepreneur. Entrepreneurs are hungry to learn and iterate. A VCs honest assessment can really help them.

— Be timely. I strive to give a timeline for a response at the end of a meeting and then try my best to stick to it even if at that point I can only say “ hey I need more time”

— Be helpful. Offer to make an intro or two for the entrepreneur to someone who could help with the evolution of their idea or lead to a customer engagement. Or even a venture firm that may be a more suitable partner for the company.

I know that these things are easier said than done given the velocity of activity that flows through our shop. And I know that I have been sometimes delinquent in following these suggestions myself. But there is a damn good business case for making every investment turn down “the best break-up ever”.

*note — post originally published Dec. 2, 2013