How to make the best out of an investor meeting (and how to see my free times with

Over the last couple of months, I’ve had the great pleasure of meeting with a ton of early stage startups.  Most times, the entrepreneurs are great, the ideas are sometimes hit and miss, but the biggest variance is their ability to effectively run a meeting.  I’m not talking about having a great pitch—because sometimes a pitch isn’t what a particular style of meeting really calls for.  Here are some recurrent themes and tips that I think would make investor meetings more useful.

1) Get out of information transfer mode and get into listening/conversation mode

Some entrepreneurs approach a meeting by aiming a firehose of data and features at me and just letting it rip—and they get noticeably flustered or frustrated when I attempt to interrupt the flow.  That’s hard, because I tend to be very Columbo-like in my train of thought—jumping in at random points.  It creates a number of issues.  First, without making this a back and forth, it doesn’t give you an opportunity to adjust the conversation for each investor.  You don’t want to give every investor the same pitch because we’re not all the same—we don’t have the same levels of expertise in your field, interest in different models, or innate beliefs about the world and the future.  You want to learn just as much about us—also to figure out if we’d make a good partner—as we learn about you.  On top of that, anyone who doesn’t take the time to learn about me or about First Round, in my mind, appears desperate—as if they’d take money from anyone willing to write a check.  The most sought after entrepreneurs want to know what value we can add over and above our money—and the aspirational ones are just happy to get a meeting.

2) Help the investor get unstuck

The key to your success might be X, but I’m still stuck on Y.  Y might be utterly insignificant, but it doesn’t matter, because if my caveman VC brain can’t wrap my head around Y, anything you tell me after that will only get half attention while I try and figure Y out.  You need to identify the blockages in my head that prevent me from getting to the finish line—maybe even ask me right off the bat what my biggest concerns would be knowing what I know at the outset.  Spend less time telling me what you think I need to know versus helping get me past my objections.

3) Recognize the dynamic, but don’t overplay it

Sometimes, you’re in a meeting with the founders of [insert billion dollar exit here] and they don’t need your money.  Most times, that’s not the case as an early stage investor.  You probably need funding more than anyone can know for sure that you’re going to be a success.  If you need investor to do something (like write a check) more than they want to do it, then you’re not exactly peers in that relationship.  That means you’re generally going to go to their office, work off of their schedule, etc.  It also means that you don’t make jokes at their expense to lighten the mood—and you definitely don’t spend the first 10 minutes of a meeting joking around at their expense.  Sound silly?  I’ve seen it happen.  Worst of all, it was a business development intensive business—so I took their failed attempt at building a relationship with me as a signal of what I could expect from them when they approach their potential partner pipeline.  Needless to say, I didn’t get there on that deal.

At the same time, once you get past the whole asking for money thing, let’s get one thing straight—entrepreneurs create way more value than their investors do.  So, you shouldn’t fall to your knees offering your firstborn at an investor meeting.  You don’t need to buy me lunch or coffee or whatever to get me to take a meeting—it’s my job to.  I’m not taking a meeting with you as a favor.  I want to and I need to.  Personally, I find it a little embarrassing when entrepreneurs overthank me for taking a meeting out of my busy schedule.  You know what’s in my busy schedule?  Great entrepreneurs like you…  that’s the whole point.  Confidence needs to convince you that I’d be crazy not to take a meeting with you—but, if I, in fact, don’t want to take a meeting with you, free lunch isn’t enough to compensate me for a lost hour. 

4) Be persistent, but not a pain

If you e-mail an investor or someone intros you, and you don’t hear back, just hit them again politely with, “Just want to make sure you got this.”   If you email me once, and then I never hear from you, I’m going to assume that’s the way you try to close sales deals or hires—or that you didn’t really want to meet with me.  Don’t get me wrong—I wish I could get to every e-mail sent to me within a day, but it’s not realistic… and sometimes, I need a nudge if things get lost in the flow.  It’s not a function of my interest at all, so if you want to chat with me or any other investor, just politely keep at it until you get a yes or no.

5) Do a time check

Ask the person how long they have.  Sometimes, an investor has back to back meetings but needs to squeeze a quick phonecall in between—or is cutting it close with their next location.  If you can help them shave 10-15 minutes off the end of your meeting, they’ll appreciate it.  Plus, there isn’t much more you can get done in 60 minutes that you can’t get done in 45.  They might go the other way and give you more time as well—you never know, but it’s always good to know if you’re running into a point at which the other person is going to mentally check out because they’re worried about making a flight or another meeting.

6) Outline your goals

I once did a sales training class where the guy said that you should start out by saying, “Would you feel comfortable telling me in 10 minutes whether or not this seems like a fit, and whether or not we should continue the meeting?”  I thought it was pretty ballsy—but it protected everyone against the downside of getting stuck in a meeting that was never going to result in a success.  Let’s say I realized you were too late stage, or I didn’t realize you were a medical device…  We’d both be best served by ending the meeting early, right?  Of course, I don’t expect anyone to do this, but I totally understand why both parties would want those other 50 minutes back once you realized it wasn’t going to happen.  In this way, the initial goal for the first 10 minutes was to see if there was even a fit.  That’s a good goal for the first 10 minutes.

After that, having a sense of what you’re trying to do is helpful.  For example: “I’d like to convince you that a) enough people need this, b) we can find those people and acquire them profitably and c) that there are natural acquirors to this business.”  This way, the discussion will have some structure and you won’t spend too much time on any one thing because you’ll be focused on getting through a reasonable outline for the meeting.


While we’re on the subject of meetings, I’ve been experimenting with a new way to schedule meetings called  There’s now a link on my blog where it says Meet in the navbar that links to my profile, which shows all the free times in my calendar.  If you’d like to meet with me, just look at my calendar, pick some times, and send a request from that page.  All I need to do is confirm one and it automatically shows up on my calendar.  Keep in mind the following:

1) I’m not lowering the bar for meetings—just the friction in scheduling.  I’ll respond to your request if I don’t think it’s productive or appropriate to meet face to face.  I’ve done it before and no one seems to mind if I turn them down—it’s not really much different than turning down an e-mail request for a meeting, I suppose. 

2) Give me some details—a link to a site is great, or some information on who told you to meet with me, or who we both know in common, etc is really helpful for me to figure out whether it makes sense to meet.

3) Forget this week unless I mention it… usually the current week is pretty full and whatever few free times I have, I’m actually trying to do some work.  If you’re only in NYC this week, however, just let me know that and we’ll see if we can make it work. 

So there it is:  <—My free times.  (A lot of people think I’m going to get overhwhelmed with requests, but I don’t think so…   mostly b/c the average person won’t sign up for what they know would be an unproductive meeting if they know they don’t have much to show.  It’s not like people randomly show up at offices all the time, even though they have people’s addresses… why should this be different?)