(Editor’s note: Larry Chiang is CEO of Duck9 and is also co-moderating the upcoming ReverseVC Pitch Panel and Dinner at Stanford. He submitted this column to VentureBeat.)

Catching the eye of a venture capitalist is hard enough. Convincing him or her to mentor you – especially if they’re not familiar with you and your work – is a much more difficult proposition.

It’s not impossible, though. What it takes is accelerated networking skills that allow you to beat the Catch-22s that so often trap entrepreneurs. Here are seven tips that will help you get your foot in the door.

Don’t ask for a coffee – I believe that anyone in this world can be gotten to and networked with. The first step is rarely ever a coffee.

A coffee connotates a 90-minute minimum time commitment for a VC. A better first step is a 5-10 minute phone conversation. Before you get that coveted ten minute wedge of phone time, though, you’re going to need to do some work.

When the student is ready, the teacher appears – I think I first read that phrase in a fortune cookie – but that doesn’t make it less true when it comes to mentorship.

Tactically, this might mean ambushing a VC at a party, conference, panel or party. I mention parties twice since they’re a favorite hangout for many VCs. And by ambush, I mean combine your elevator pitch and charm as you solicit an invitation to further interact. Your goal is simple: Get yourself mentored.

Pre-network with a VC via a portfolio company introduction – There’s a phrase I coined called “the transitive property of influence”. Essentially, it means charming once and transitively conveying it to the end target – the VC you want to have help you.

How it works is pretty simple: You reach out indirectly to a VC by directly romancing the CEO of one of his or her portfolio companies. If that executive makes an email introduction, you’re in.

Woo by reading – In Star Trek, Spock would do the Vulcan mind meld to get insight into someone’s thoughts. You can go one better without risking the assault charge by reading what your would-be mentor reads and reading what they write.

I used this practice to woo Roelof Botha after he mentioned, “MoneyBall” on a panel I chaired. Read the books, blogs and other material they recommend to build rapport. The more you have in common, the better.

Mentorship as a funding vehicle – I moderated a panel at SXSW where VC and 500 Startups founder Dave McClure gave some cogent advice to the audience: “If you want a VC to consider giving you money, ask for mentorship first.”

The VC’s risk is mitigated when you take their coaching. It is, in many ways, a trial by mentorship, allowing them to augment your shareholder equity before they invest. And it increases their confidence in the likelihood of a positive outcome.

Ace the initial conversation by mentoring them – Mentorship goes both directions. The student/teacher dynamic often includes some role reversal. In the end, if the mentor is good, the student surpasses the mentor pretty quickly. In the interim, here are ideas to get you started mentoring your mentor

  • tell them what to pay attention to
  • tell them what trends you see
  • tell them your opinion of what recent news means
  • tell them what else you like in your marketplace
  • tell them what specific industry problems exist and how you’re solving them

Kiss VC Butt – Read the following verbatim and try to minimize your gag reflex: “Hey I read all about you at Stanford Business school website and I think you’re an incredible genius. I have dreamt of one thing and that is to get a call back from a thought leader like yourself”.

Do VCs have massive egos? It’s hard to say. But I do know that after you magnanimously kiss ass like that, it rarely hurts your chances. You don’t, of course, want to be the obvious brown-noser in the room. My hack is to sincerely compliment them on something undeniably true, so it comes across as genuine.

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