The Art of Being a Dick
A couple of days ago, Techstars here in Boulder hosted their annual Techstars For A Day program. The idea is to bring a bunch of potential Techstar companies together with a bunch of mentors and alumni to discuss the program and learn more about each other.
As I walked in, Colin, who was working the door, and who I had met the previous year at Techstars For A Day, greets me and says, “Don’t be mean.”
“Wow,” I think to myself, “am I really mean?”
One of the activities I enjoy most at Techstars is Pitch Practice. I consider myself decent at pitching, and I want to add as much value as I can. Last year, I attended 3-4 sessions. During one session, a company led with the fact that they were married.
“Don’t lead with that you are married. 1) No one cares; 2) Being married adds no value to your potential success, and frankly, it could be a turnoff to investors.”
Another company presented their idea, and I responded after a few others gave the normal platitudes, “Guys, I viscerally hate what you presented. It fails on all levels and personally its disappointing because I know you are better than that.”
At the end of the session, Nicole, GM of Techstars, pulled me aside and said, “Some of the companies feel you are just being mean.”
“Really?” I ponder. “Am I really mean?”
Over the years, I have realized that generally people dont like to give other people raw truth. It can cause pain; it isnt affirming and in many ways its not socially acceptable.
The key to providing raw truth is not the truth you provide, but the actions you take immediately following. In the case of the second company, we spent 2-3 hours revamping their presentation, to what turned out to be a really strong pitch. In the case of the first company, they started to focus on their product and their team, and less on their marriage, creating a much more cohesive story.
Last night, Techstars had an open house. A few companies that didnt get invited to Techstars For A Day, or were there and wanted to have further discussion came. I sat down with one that specifically wanted to talk to me. “I heard you are tough” they said.
“I am just honest,” I replied. (Actually I said I am raw. Which is my new favorite way of saying if you play with the bull, you might get the horns. Or dont poke the bear. Or any other great saying.)
Over the course of the next 30-45min we chatted about their idea. We spent time around why the idea was important to them, what were their challenges, how much success have they had. What were their core values.
“I hate your idea. Its lame.”
And, about 20min into the conversation, one of the founders leans back and says, “Well, I have this idea, that I havent told anyone. What do you think of this?”
“That is a good idea. That is something that really solves an issue. Its hard, but if you pull it off, its amazing.”
And I started to see the wheels spin. If I had heard the first idea and given them platitudes, would I have gotten to the better idea? No. I would have smiled, listened politely, and then crossed them off my list of interesting companies.
Providing raw truth is hard. Its easy to be mean. It creates an aura around you that you arent someone to trifle with. It makes you different.
But, when you can artfully be a dick, the outcomes are often quite amazing (at least when the other person doesnt cry).
And, you want to know the real, raw truth about me? I care. I really, really care. Entrepreneurship is hard. Startups suck. And, no one is doing anyone a solid by providing polite feedback. There is no excitement in watching a young entrepreneur “pay his dues.”
The next time you ask someone for advice, ask them to be truly brutally honest. Politely honest does you no favors. You will continue down a path that could lead to abject failure, and it is extremely condescending for another person to believe you cant handle the truth.
After all, how are you ever going to learn to duck, if you dont get punched in the face?
Related articles
- The Man Who Brought TechStars To NYC – with David Tisch (mixergy.com)
- TechStars to give over $25,000 to winners of its StartUp Madness tournament (thenextweb.com)
- The MicroInterns: Middle-Schoolers Visit TechStars, Get a Lesson in Startup Life (readwriteweb.com)
- TechStars Boulder Applications Are Open (feld.com)

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