Something I learned 20 years ago has made a huge difference to my writing, presenting, and pitching: you have to know what your audience is thinking.

The original idea came from a how-to book on writing I read back then, but it’s a common enough meme.  Typing “you have to know what your audience is thinking” into Google just now (sans quotes) gave some 46M hits (although only 8 for the quoted string).

If you bear in mind, when making a pitch, where your audience is going to be mentally at each stage of the pitch, you will certainly make a better pitch.

Take the usual custom (in which entrepreneurs are widely coached) of spending a huge number of slides at the beginning of a pitch describing and justifying the market problem your startup will address.

Complete waste of time.

Most investors will fall into one of three camps in the first 20 seconds of your “market need” recital:

1. I get it, I agree 100%
2. I get it, I disagree 100%
3. I get it, I’m not sure if I agree or disagree, but I’m willing to stipulate that there is such a need for the sake of argument while you tell me what you’re going to do about it.

In all three cases, they’ve made up their mind.  Ten more slides will only put them to sleep.

Of course, short of telepathy, we can’t know what our audience is thinking.  But we can make shrewd guesses along the lines of the above.  And making the effort really opens your mind to how to structure the pitch so that it tracks with your listeners’ real state of mind, which puts you way ahead of the pack.

Prior to becoming a VC, I pitched startup ideas to VCs (and others).  I’ve had my share of rude, entitled VCs who, I felt, gave me short shrift.

But from the other side of the table, I see if not as a problem with the VC but as a problem of the entrepreneur’s conception of and contact with the VC (s)he is pitching to.

What do I mean?

I just finished an email exchange with an entrepreneur who had cold-called our offices and asked to speak to someone, anyone, about his idea.  To this guy, the relationship with him was irrelevant, and all that mattered, or ought to matter, to me was the quality of his idea and his proofs that the idea resonated with potential customers.

Actually, it’s just the opposite.  With a  very early-stage idea, the character of the entrepreneur matters much much more than the quality of the idea, if only for the simple reason that most ideas that succeed as businesses do so by changing course in reaction to circumstances (what we now call “pivoting”), and the entrepreneur needs to be someone with the vision, fortitude, and, yes, the character, to know when to hold and when to fold.

When the connection is a cold call or a cold email, we know nothing about this entrepreneur’s character.  So I have a general rule that if an entrepreneur is not introduced to me by someone I don’t go further with a project.

What does mean for entrepreneurs who don’t know any VCs?  It means you have to get to know us, through accountants, lawyers, other entrepreneurs, startup helpers such as incubators, accelerators, and the like.  You could also start in a cold contact by introducing yourself and saying something about your background.

This entrepreneur responded to my rejection by saying that VCs didn’t get it, he would never understand us.  I would ask him what he would say if a person unknown to him called him up on the phone and asked him to invest $1M in his idea, how would he react?  He would probably (I would guess) want to know the person he was dealing with a bit better before proceeding with him.  And if he had enough people calling him, he probably wouldn’t have time to get to know everyone who called in.

I wish it were a different world, where there was enough time and bandwidth for everybody.  But lacking that, knowing what your potential investor is thinking will help you figure out how to approach him or her.

Not really anything to do with the Project, but I’m packing it in on an explicit practice of standing or sitting in a “Big Body Language” pose for 2 minutes every day (early intervention from February, discussed here).

The main thing is that I’ve gotten restless with all the “good habit” things I have to do every day, mainly as a consequence of aging: brushing, flossing, exercising, meditating, reading, writing, blah blah blah.  Preventive maintenance of one sort or another is becoming an alarming % of my day.

Also, though, from the Chutzpah POV, the Big Body Language seems to have organically populated my day to the extent that it’s not necessary to set aside 2 min just for that.  I have much better mindfulness and results displaying Big Body Language in meetings, when considering chutzpah-consuming ideas or moves, or even just sitting at the dinner table.

So I can cut the 2 minutes out of my day… and save the time for just being alive.

OK, May is over, time to re-tool for Month 5.

Start by retiring a couple, which proved to be No Problem:

• Be Interesting when you get on stage: Didn’t prove to be a problem for me.  This is one area where I’ve been blessed with plenty chutzpah.  Honorably Discharged
• Learn to Love the Phone: Surprisingly, this has proven to be a fairly smooth area, too, after years of hating and fearing talking on the phone.  Maybe a collateral effect of other chutzpah builders?  Honorably Discharged

New ones for May:

1. Continue with Speak Truth to Power: This hasn’t been easy to get going; maybe we need a dose of mindfulness about occasions when I should have done so, but didn’t.
2. Dare to meet people more popular than you.  I hate this; I shrink away from meeting people I think are popular, even when I might really like them or vice versa.
3. Dare to be unpredictable.  A fundamental tool of chutzpah is keep people a bit on edge about what you’re going to do next.  This will likely not be easy for me.
4. Dare to say “No”.  A staple of Assertiveness Training.  Good practice.

Wish me luck.

This is taking us a bit far afield of the Chutzpah theme, but I’ve been reading a bunch about mindfulness as background to using it as a general tool for enhancing my chutzpah and other good traits (as well as diminishing some less-desirable traits, but that’s another story).

Mindfulness is not some gushy New Age concept.  It’s a pretty understandable state of mind where you are neutral-to-friendly about what’s going on in your mind while not getting sucked into it.  Yes, you are “not attached”, but in a rather rarefied sense: you’re not exactly remaining indifferent while lovely foodstuffs or gorgeous sex partners are presented to distract you from your detachment.  You feel your hungers and you feel your lusts but you’re not drawn into them to the point that you lose your awareness of yourself.

In any case, one area where mindfulness is familiar and key to success is debugging.  I’m most familiar over the years with debugging software, since that what I did for a living for twenty-odd years and may do again someday, but if you read something like “Shop Class as Soulcraft” or “Zen and the Art of Motorcycle Maintenance” other Maker-ish stuff, you can see the same use of mindfulness and debugging, only in this case debugging shop tactics or repair.

The idea is that you can’t see the problem if your mind is clouded by attachment.  You get attached to the last thing you fixed, so you (wrongly) conclude that the problem you’re looking at now has the same cause.  You get attached to some of your presuppositions (“the problem must be in the allocation module”) and close your attention off to data that lead you away from that to the correct root cause.

Most makers of one sort or another have encountered mindfulness in this disguise.  It’s part of what I love about debugging: you’re rewarded for the rectitude of your mindfulness.

Of all the Interventions I’ve tried so far this year, Be Interesting When You Get On Stage is the easiest for me.  I’ve been in the habit of being interesting for decades, and although there are venues where that’s more challenging for me – small crowd of powerful people I want to impress – I generally leave my mark.

But it ain’t as easy as it might look.  For whatever reason, each interesting remark costs me something.  If I try to pay mindful attention to it, there’s a very brief flash of longing, longing that these people will like me, like what I’m saying, reward me, praise me, then a flash of fear that I won’t be able to be heard, that they’ll ignore me, then finally a flash of angry contempt, for them for scorning me (in advance, so to speak), but also contempt for me for wanting their good opinion.  The anger stays with me, largely as anger at myself, and it’s not uncommon for me to recall with self-contempt charming things I’ve said at a dinner party on the way home: my wife and I call them Bad Thoughts.  The Bad Thoughts crystallize all the contempt for myself without the intervening longing and anger at the others that make the contempt more comprehensible.

Easy to see why the roomful of powerful others is so challenging, given this internal play.  But it took years to decode it and I’m still not seeing it all in the moment, which is probably the key for harnessing these charming interventions in the service of Greater Chutzpah.

So, yesterday, I had a big meeting to attend, one where I’m supposed to do great things but in fact have been pretty much unnoticed in the hustle and bustle (somehow, despite my charm and good looks…).

In the past, I’ve longed to get out of going, and have used some excuses to do so.

And yesterday morning I was full of them: I had gotten in late the night before, there had been a chance I’d be out of town that day anyhow (which meant, I thought, that I wouldn’t be missed).

But because of mindfulness, I had an inkling that these were excuses, and what was lurking beneath was The Fear: they will ignore me (which, as I have said, is a big one for me).

I didn’t have enough direct chutzpah to get myself to go to the meeting anyhow, but I had enough to ask for help: I asked my wife what she would do.

She said, “You might as well go; something good may happen.”

And that was enough to tip me.  I went, and it was in fact quite good.  I spoke up, I got noticed (by some for the first time).  I made a splash: a very mild one, but a splash, instead of a no-show.

Mindfulness + asking for help = different outcome.

As I start tooling up to speak up more, it occurs to me that you can be a jerk about speaking truth to power.

There’s a way of doing it that makes you lose credibility instead of gaining it.  If you wade in with a “take-no-prisoners” attitude and blurt out your truth, it’s as if you hadn’t said anything.

In “48 Laws of Power”, one of the laws has to do with this.  It’s “Don’t argue with your superiors, but demonstrate the truth of what you say indirectly.”  That’s part of it.  A standoff – opinion against opinion – with a powerful superior just ends up with all your supporters and all your support evaporating and a conclusion that, even if you’re on to something, it couldn’t amount to much.

Demonstrating, to the contrary, invites others, including your powerful superior, to draw their own conclusions about the “facts” (although, of course, the conclusions are yours all along).

I’d love to get better at demonstrating as part of speaking truth to power.