When is the best time to pitch an investor?

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I was moderating a VC panel a couple of weeks back, and we talked about the best way to get an investor’s attention.  One of the panelists said, “Well, the worst way is to bombard me at an event.”  And the more I thought about it, the more I disagreed.

When I was an entrepreneur, I don’t think I had any sense just how busy most investors are.  I guess I just thought they all sit in cushy chairs all day and sip tea and hang out at the Rosewood on Sand Hill  (ok, maybe some investors do).

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Originally posted by gameraboy

But certainly new VCs are not doing this.  They have to hustle for every deal.  They have to hustle to fundraise for their current or next fund.  So how do you get on an investor’s radar?

Here’s a snapshot of my day-in-a-life:

  • I average 6-10 meetings per day (typically 20-30 min mtgs), including meetings with both current and future portfolio companies
  • I block off 4+ hours a day for emailing with founders
  • I do roadshow events or speak at conferences on average 2-5 days per month on the road, 1 day locally
  • Right now, my work inbox has
    • 80 import ant unanswered emails
    • 276 back-and-forth email threads with prospective founders
    • 1500+ emails that will just never even get opened because the subject line isn’t interesting
    • My personal inbox isn’t any better, unfortunately

This isn’t to say, “Oh I’m so busy that I’m holier or more important than thou.”  I’m trying to paint a picture of which channels are too competitive to get attention and which channels have opportunities.  I imagine that this is similar for many other investors.

Based off this, if I were pitching myself, here are some takeaways:

1. The best place to pitch an investor is when there is unstructured time

If you are at a conference or an event, investors actually have a LOT of downtime.  They have blocked off time on their calendars to be at an event for x amount of time.  But aside from their speaking slot or panel or whatnot, they are more or less available!

Now, a lot of investors don’t stay for the whole event, but if they are speaking, you can bet they will show up for at least that part.  You have the opportunity to find them before or after their talks.  Have you ever seen an investor on his/her phone emailing or texting people in the corner of a room?  That is your opportunity to jump in and do an elevator pitch.  Be polite and friendly, and you won’t be interrupting.

A strong elevator pitch will cover something unique about you, your story, any KPIs or metrics you may have, and why what you’re doing is important.  Most elevator pitches are really weak.  In part, it’s because they all sound the same and often are too long or rambly.  Also, an elevator pitch does not mean you just talk at someone.  An elevator pitch is a dialogue, but it’s a short one where you need to cover enough interesting points in order to get a meeting.  If the investor is intrigued, you may end up having a much longer conversation at the conference itself.  My longest conversations with entrepreneurs have been at events, and many of the portfolio companies I’ve championed over the last two years have been startups I’ve met at events.

Make sure that there is a strong next step after meeting with an investor.  A weak next step is “Email me.”  You don’t want to end up in someone’s inbox.  A strong next step is a confirmed meeting — it could be at a specific time at the event itself or later on — and it should be locked down or, at least, you should be in touch with an investor’s EA.

2. Cutting through an email inbox is tough

Everyone’s inboxes are busy.  If you must go the email-route, here’s how.

In some ways, this is why people say strong referrals are a great way to meet with investors.  This is true — if the referral is really strong.  Most of the time, referrals are weak or are just OK.  For example, people I’ve met once or twice before do not make good referrals for me.  You’re much better off emailing cold.  Furthermore, there are even some people’s referrals who are negative signaling to me!  On the flip side, there are some fellow investors’ referrals I would hop on immediately.  The issue, as an entrepreneur, is that you don’t know where your mutual connection sits in an investor’s eyes.  Your referrer doesn’t know where he/she stands either.

The best thing you can do is to try to get a warm referral but in parallel, send a cold-email.  It won’t hurt.  Sending someone an email twice isn’t going to be weird.  I probably wouldn’t even notice if someone emailed me 3x.

If you cold-email an investor, whatever you do, that first email must be compelling enough to be moved into a concrete meeting slot.  Asking someone for 15 minutes of his/her time while providing zero context on your business is a good way to get archived immediately.  Why?  Because even though it seems like it’s just 15 minutes of time for a call, that’s what — I kid you not — thousands of other entrepreneurs are asking for at the exact same time.

3. Make the most of whatever structured time you have

Once you have a concrete meeting time, no matter how short, you must have a pitch that is appropriate for that time period.  Most of my first structured meetings with people are 20 minutes.  This is pretty short. A lot of people try to push for longer meetings.  No matter how much time you have, you should have a pitch that can fit that time slot.  You should have pitches for:

  • 30 seconds
  • 5 minutes
  • 20 minutes
  • 45 minutes

The goals for each of these blocks are obviously very different.  You’re not going to get investment dollars on a 30-second pitch.  The 30-second pitch is to gauge if it’s worthwhile to move you to a longer pitch.

Similarly, I favor 20-minute conversations as a starting point because it’s enough time for a concise, direct entrepreneur to outline the following information:

  • Team backgrounds and mission (why they are doing this)
  • The problem they are solving
  • Brief solution + differentiation
  • Notable KPIs
  • High level unit metrics

The best entrepreneurs I’ve met can cover all of this and more in 20 minutes and still have time to spare.  They have thought deeply about what points are important and made sure to cover all of those points while avoiding long, meaningless tangents.

This means that you’ll need to pace the conversation accordingly.  If 10 minutes have gone by in a 20 minute meeting and we’ve only talked about your team, that is not good.  You must drive the conversation to cover everything you want us to cover — i.e., whatever is needed to push me to the next step — in whatever allotted time.  We won’t be able to schedule another time  to cover anything we missed unless that first meeting is compelling enough.  As an entrepreneur, it’s your job to cover everything that is compelling to get to that next step.

By the time the call is over, you should know concretely what the next steps are.  If you don’t, make sure to ask and push.

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