Prepare and Be Prepared

Brad Feld has a great post this week titled, Don't Be Casual, in which he talks about a company in his portfolio that did a "casual" presentation to a VC firm, only to realize that the company's idea of casual didn't match the VC firm's.  In the end, "the meeting was a disaster."  Brad concludes his post with the message:

". . . in all fundraising situations – don’t be casual.  The first impression counts a huge amount and sets the tone.  This is obvious, but even after doing hundreds of financings, I blew it this time."

The post is a terrific lesson from many points of view and, while the comments seem to focus on the failure of the presentation itself, I believe that there are some higher-level lessons that can be drawn from this experience.  Two, in particular, come to mind.

1. Generally speaking, if you blow your initial shot with VCs you've probably poisoned the well.

• Many of my VC pals disagree with this point, but I've seen it time and again.  Most VCs have a lot on their plates.  If they're not out fundraising, they're looking at loads of deals or managing the ones already in their portfolio.  Because they're busy, the impression they take from their first meeting with you will likely be the one they fall back on the next time they have the opportunity to think about your company.  If it was bad, it's highly likely that their negative memory will make it easy for them to pass on the next meeting and ultimately, any deal with you.  This remains true after you've gone back, having taken their advice on what would make your idea better, and refined both your idea and approach.
• Make sure that you've gotten all the advice and made all the changes to maximize your potential value to your target VCs before you present to them.  Find outside advisors and present to VCs that aren't on your target list to get early feedback before you meet with the people you want to impress most.

• Until you're the person in charge, the one making the decision or a recognized luminary in your field, always make it a high priority to do what's important to your audience better than they expect it to be done.  That requires, of course, that you know what they expect; at least at a high level.  Uncovering expectations is usually fairly easy - ask.  If you can't find out, do things in a way that would blow anyone away . . .
• Treat the person your meeting like they're the Queen of England - formality never hurts
• Several readers of this blog feel differently about this, but I stand by it - stand up when you present.  It shows respect for your material and the audience.
• When presenting, be prepared to take the conversation in many directions.  Check with the audience after the first few slides to see if your guess about best path is correct, if not, go to plan B, C or D.
• Get feedback up front.  State what you believe are the expectations for the meeting as the meeting starts.  You may be surprised to find out that the person/people you are meeting with will tell you exactly what you need to do.
• Don't use jargon, acronyms and buzzwords to try to impress your audience unless you know for a fact that they're in your audience's lexicon.
• When in Rome, dress like a Roman.  Wearing cargo shorts and Chuck Taylors may fly in the office and maybe even with customers and partners, but if you dress that way in a meeting with a banker in New York, no good will come of it.
• Whether your presenting to VCs, meeting with customers or presenting at a conference, prepare and be prepared.  Knowing what to do ahead of time is always the best answer.  If that's not possible, and sometimes it's not, then set yourself up to deal with as many contingencies as possible.