How To Score a Second Date With An Investor

The title of this post could probably more appropriately be “How NOT to Shoot Yourself In the Foot On Your First Date.”

As a member of the review committee for investment programs throughout the region, I’ve seen countless examples of poor presentation techniques.

Recently, the folks running the popular Innovation Fund at Lorain County Community College asked myself and Bob Cohen (CEO and Director of Business Assistance at Braintree Business Development Center in Mansfield) to help with this issue.  Too many promising start-ups were not getting their “second date” due to presentations which didn’t position their companies or technologies in a positive light.

One of the ways Bob and I came up with to help as many people as possible was an overview presentation on how to present to the Innovation Fund.  The presentation was titled slightly tongue in cheek as “Getting that second date…  Navigating the regional pitch process by NOT embarrassing yourself on the first date.”

I’ll save Bob the embarrassment and admit that the dating metaphor was my idea, and one that I use often when coaching entrepreneurs on pitching the various early stage investment programs around the region.  Approaching an investor presentation from this mindset, underscores two important points:

  1. Good first impression – the best way to get a second date is to not screw up the first one.
  2. Get that second date – in your initial presentation, you’re not looking to get married, just get asked back.

So with your first date (presentation) in mind, let’s look at some what you can do to raise your chances of getting that “second date”.

The Four P’s

The foundation of any good presentation is fundamentals, and the Four P’s are a great place to start:

  • Planning — Who are you talking to?  Why are you talking to them?  How much time do you have?  What message must you display?
  • Preparation — Outline your talk first, then prepare slides.  Prepare some keyworded notes.  Proofread carefully and have someone double-check you.  Make sure your slides are easy to read.
  • Practice — Get feedback.  Try to be relaxed.  Eliminate unnecessary information.  Practice constantly.
  • Presentation — Speak loud and clear.  Maintain eye contact.  Don’t look at or read from the screen.  Be understandable.  Have a clear summary and ending.

Tell Them What They Want To Hear

While the Four P’s set a strong foundation for your presentation, the content you present is just as important.  I can’t think of an investment opportunity in the region where the governing body doesn’t provide an proposed, or sometimes required, outline for your presentation.  So for content, your first, most important guideline is to make sure you cover all the points in the provided outline.

Providing the requested content is a great start; add in a little analysis and you’ll do even better.  For all the content requested, ask yourself why you think it’s important.  Most funding programs ask for backgrounds on the entrepreneur and their management team.  At the surface this may sound like a simple request; one satisfied with names, degrees and associations.   The question behind the question though is rooted in execution risk and what you are really being asked to provide is proof that you and your management team have what it takes to make this start-up a success.

So when it comes to content, always tell them what they want to hear, but make sure you understand the question behind the question.

Don’t Shoot Yourself In the Foot

Finally, even with preparation and practice along with answers to all their questions, you’re still not guaranteed that elusive second date.  Have you ever been on a date (or met a potential vendor for the first time, or interviewed a prospective employee, etc.) that presented well and came prepared with everything you asked for, but had a really annoying habit?  Maybe they smacked their lips together every few seconds, or finished your sentences for you.

In the coaching I give, especially for entrepreneurs pitching for the first time, is to remember that you are selling yourself just as much as you are selling your company.  Those annoying little habits add up.  String too many of them together and pretty soon you’re dragging your company down with them.

When making a pitch, any pitch, but especially one for funding:

  • Don’t use excessive jargon, keep things simple to understand
  • Don’t say you are the “only one in the world”; almost always you’re not
  • Make sure to follow the guidelines
  • Mac users – keep in mind you’ll probably be presenting on a Windows machine
  • Don’t play with the laser pointer, only cats enjoy that
  • If you bring your presentation on a USB device, make it the only file on that device
  • Don’t overlook the effectiveness of a well-crafted cover slide

Those might be the annoying little habits, but the following are the real deal killers:

  • No overwhelming market advantage
  • No explanation of your technology/product, or an overly-complicated explanation
  • No mention of competition
  • No discussion of how you make money
  • Deciding to wing it
  • Online demos or embedded videos that don’t work

Good Luck!

There are no guarantees in the funding world, but following the real world tips I’ve presented above are a great start to success.   You may not end up married, but you’ll be well on your way to a second date.

Do you have a great story about how you got that “second date” with an investor? I’d love to hear it! Comment below, or e-mail me at

Posted by MAGNET Ohio in Entrepreneurship

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