Crushing a First Meeting

Anyone who’s ever done a fair amount of hiring recognizes that a resume is an introduction. Hiring off a resume is darn near impossible. [As an aside, I hate resumes. I don’t even have one. If you want to get hired at CV, find a novel approach.] You’re looking for rough evidence of lines, not dots, as popularized by Mark Suster. You’re looking for differentiation, creativity. But the resume gets you in the door – it won’t get you the job.

Over my nearly three years at Chicago Ventures, I’ve had the pleasure of meeting with hundreds if not thousands of entrepreneurs. And if I had one take away it’s that overwhelmingly people try to accomplish too much in a first meeting. I have my theories on why that is – possibly the cultivation of a pitch deck culture where entrepreneurs believe that they have one 5 minute shot in front of a hundred investors to land a deal. The truth is I don’t know why. But it does everyone a disservice to try to do everything at a first date.

Chris Dixon famously remarked, in response to Sarah Lacy’s question of the one thing he would have done differently in retrospect as an angel investor, that he would have cut every meeting to 10 minutes. He cites as the reason that the best companies shouldn’t need an hour of explanation. If you can’t sell a VC with a 30 second elevator pitch, how will you ever sell a paying customer? I’d posit there’s another reason – a 10 minute constraint forces you to focus on what matters and tests an entrepreneur’s ability for concision.

Charles Hudson, a talented VC at SoftTech spurred an active debate recently when he advocated going into first meetings entirely cold – no pitch deck via e-mail, nothing. I can’t say I agree 100% in actuality, but I agree fully with the premise: decks don’t tell the story – people do.

I’ve spoken with a number of investors I admire who prefer to make their first dates a walk and talk meeting. Others who will refuse to allow a deck to lead the conversation. The goal is to get to know the real you – not the you you’re pretending to be or have been told you should be.

The purpose of a first meeting should always be to get a second meeting. It is a rule I try to live by in a variety of endeavors. Heck, I am even dis-incentivized to see a movie when the trailer gives away too much. As a VC, the first variable I optimize for is interpersonal connection. Successful first meetings are ones where we connect over purpose, mission, and dreams. We will never connect over financial models – it’s inhuman. Great first meetings end with a variation of: “I’m intrigued and would love to learn more.”

Relax. Be yourself. Forget all the training. And crush first meetings.

Ezra Galston


Posted On

December 10, 2014


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