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Sticking to Your Guns in Investor Meetings

Sticking to Your Guns in Investor Meetings
Matthew Bellows
Matthew Bellows

Matthew Bellows

3 min read0 reads
Yesware the Company 


  1. The Meeting
  2. The Outcome

We’ve started taking investor meetings for an angel round, and, three days in, so far so good.

Last Thursday, Cashman and I met with a father/son team who were both interested in learning more about our plans. The father is a very successful business person, the son is very bright technically. So they were a great pair to present to and get feedback from.

The Meeting

They had shredded the plan, re-engineered the numbers to test our assumptions, and they came prepared with all kinds of great questions. Plus, they were hungry, motivated, and adventurous enough to trek out to Scup’s for lunch. The perfect meeting. After talking through any number of issues, the son said, “This is great, but you can’t just call this “Email for Sales. It’s got to be bigger. It’s got to be something sexier. ‘Knowledge Network Tools’ or something like that. Email is too simple.”

As most of you know, times like this are make-or-break in meetings. In the moment you have to decide how to play it: Accept (Yah, we’ve been thinking that too…), Defer (That’s an interesting point, we’ll think in it) or Respectfully Disagree.

I said, “I agree. Our positioning statement is simple. That’s what we like about it. We’re not selling a visionary technology here. There’s nothing deep-research about Yesware Email. It’s email aimed at a very valuable segment of a very large market. We want to make choosing and using Yesware as easy to understand as possible.” The son nodded. I’m not sure if he completely agreed, but he knew where we were coming from and what he’d be investing in if he decided to go forward.

The Outcome

In the best meetings, you get tested. There’s a moment or two where you have to raise your game and really advocate for your ideas. It’s tricky to know when to do it, because this behavior can also prevent you from hearing helpful suggestions or feedback. But, in general, stick to your guns in investor meetings. They might not agree with you, but they will feel your passion and they’re more likely to see your point of view. At the startup stage, that’s most of everything you’ve got.

They might not agree with you, but they will feel your passion and they’re more likely to see your point of view.

P.S. Steve Blank has an amazing post today on the humility of targeting a new product at an existing market (RIM) vs. the hubris of creating your own market (TiVO). Highly recommended. P.P.S. Here’s yet another reason that writing a business plan is not a waste of time. You can’t have a thoughtful, provocative meeting like this without one. If I had just shown these guys a slide deck, they wouldn’t have thought nearly as hard about Yesware. If I had just given them a canvas, I don’t think they would have taken the meeting.

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