Mentors/Investors: Please don’t break it to me gently

In a great post earlier this week, Fred Wilson advised founders:

Apply the “investor discount” to feedback you get from investors. Advisors/mentors who have no agenda are a purer form of advice. Investors have their own agenda.

I recently found myself in a situation, which made me realize that we actually often face a problem at the opposite end of the spectrum. A great deal of the advice we receive is already diluted by a gallon of artificial sweetener.

A few weeks ago, one of SquareOne’s advisors made an intro to a prominent influencer in our space, someone whose work I respect and whom I hoped to get informed feedback from. Shortly, my advisor got a quick note in response that read something like: “Happy to talk to him, but honestly can’t really see what unique value the product brings.” I was on the phone with my advisor as he received the message, and so without thinking about it twice, he relayed it to me. My response: Bummer, but all the more excited to chat with him and get some tough but important feedback.

A couple of days later, I heard from said influencer. He sent me an incredibly nice, thoughtfully-crafted message. He complimented the design and the UX. He commented on the philosophy and direction approvingly. And he gently pointed out that there is some serious competition in the space. Overall, a drastically different take-away.

Now, don’t get me wrong. I am really appreciative that he took the time to craft such a friendly message. I still hope to meet up and talk. But I realized that had I not known what his immediate unfiltered response was, I would have left the interaction patting myself on the back.

I don’t need to pat myself on the back. I realize that — like most startups — we have a lot to learn and perfect. When I reach out to someone, it means that I value their judgment and hope to hear what they think we’re doing wrong. It’s my job to not have a mental breakdown every time the feedback is negative. The net-net of this interaction was him wasting a lot of his valuable time sugar-coating his feedback so much, that the value I could have derived from his advice got lost in the sweetener factory.

I identify with the mentality of always being friendly and respectful. It is in no one’s best interest to be offending founders with feedback — who knows how their venture may evolve or what they may come up next. But think about it — the founders that get spiteful after hearing your negative feedback are probably not the ones that you want to invest in later on anyway. And who knows — maybe your critique will be the nudge that will cause a very solid founder to take that pivot, and come back to you three months later with a much better-looking investment prospect. So please have a little faith in us founders. We care about what you really think. We can handle it.