Fuck Pride

Posted on June 13, 2012. Filed under: startups, venture capital |

About a month ago I was having lunch with my friend Michael Dearing at the Creamery in Palo Alto.  If you don’t know him and you are raising seed money…you should, he’s a very good dude and super accomplished.  I don’t remember how it came up (because MY MEMORY IS TERRIBLE), but I remember articulating to him that I was disappointed in myself for no longer “cold emailing” people that I admire.  When I was younger with little or no cred in startupland, I used to email anyone and everyone who I thought was cool.  I’d read an article about Elon Musk, craft a perfect email about why he HAD to meet with me, and then try every email combination known to man until I got through to his inbox.  It was a low percentage game, but I was so inspired by the achievements of others and I just wanted to be as close as possible to the biggest most accomplished entrepreneurs (and more generally people) I could find.  I’d send emails to Bill Clinton, Jay Z, Peter Thiel, it didn’t matter…it was just a game to me…all I wanted to do was sit down in the same room…pitch myself…not my idea…or my company (although sometimes I would)…but just myself…my entire goal was getting those amazing people to believe in me…to care about me…to be open to me the next time I would “need” them….if I’m really honest…I also wanted to see if I could hang…if I could keep up and if they recognized or saw me as a peer. How fast could I get the conversation to even…vs master/apprentice (although, I did appreciate the apprenticeship and was super respectful).  But something changed as I got more mature in this space…I had met enough people and worked with enough people…that even the superduper fancy people became more accessable…no longer was cold emailing the best route to these folks…people were generally one or two hops away, and I guess introductions became a bigger part of how I reached who I wanted to meet…but even still…these types of meetings…and frankly this type of reaching…really slowed down for me.  Maybe I became less wide-eyed as entrepreneurial “stars” revealed themselves as more human, or maybe I got too proud…

So anyway, I was sitting with Michael and I told him I was disappointed in myself for no longer cold-emailing people who inspire me…that maybe I was somehow embarrassed to do it because “I should be able to meet just about anyone now by relying on my friends and colleagues” or because “it’s entirely likely that I will meet the people I haven’t, and god forbid I would have subjugated myself to them via Gmail in advance” or some other stupid fucking reason that I got too proud to keep reaching…Michael sort of agreed with me, and so we both decided to cold email one person who really inspired us and ask for their time.  I had recently watched this Charlie Rose video with Jack Dorsey and was very moved by it…so I opened up my iphone and emailed him right on the spot (I actually had his Gmail from 5 years ago when I talked to him as a young associate at General Catalyst…trying to get into the round USV ended up leading….but for all intents and purposes…this was still a cold email and there’s no way he would remember me I don’t think).  Anyway, the text of my email was simple:

Subject: Hey dude

“I’d love to hang out with you sometime because you inspire me

somewhere along the way i stopped cold emailing people I admire, decided to change that today”

As I reread that right this second, it was actually sort of half assed relative to what I would have written 3 years ago…I should have referenced all our common connections and interests and provided more context for him to connect with…instead I thought my email signature with Hyperpublic and Lerer Ventures and my blog and twitter would suffice (again, maybe a victim of my own pride)…but it really wasn’t as much about getting the meeting as it was about the act of reaching…

Last night I got a note from Michael:

Subject: what ever happened?

From your Jack email. Mine to XXX XXXX went unanswered. 🙂

I sort of smiled to myself, thought for a minute, and wrote back:

“Unanswered as well. But I think we got more out of that rejection than we would have had they responded…that was kind of the point. Put ourselves in a position to be humbled…”

In summary: Fuck pride

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7 Responses to “Fuck Pride”

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What cold email responses have you gotten that have totally surprised you? Did you have any that amounted to something significant?

TONS. CEO’s of fortune 500 companies, billionaires, i’ve gotten more than one job from cold emails…

What’s your take on the max word count?

Can’t really imagine the product any other way

Nice post JC. The Buddhists call what you’re talking about “beginner’s mind”. It is utmost to them to retain beginner’s mind bc without it one cannot experience deeper levels of consciousness. (Put another way, when pride comes between a person and his/her experiences, the experiences lose their ability to be revelatory.)

Ha ! I’ve also done a lot of cold emails. I’ve had some responses from people I admire like Omar Hamoui, Craig from Craigslist, Joel Spolsky, Fred Wilson … It was such an awesome feeling and source of energy. The thing you realize when doing that is that very often, very high level people tend to respond something, even if it’s short. Whereas some people who aren’t so big might completely ignore you as if they’re too busy. I keep this list in my head 🙂

Tremendous job.

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at Jordan.Cooper@gmail.com (p.s. i don’t use spell check…deal with it)


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