Yesterday somebody asked me to look at his executive summary on SlideShare. He’s a Twitter friend; I like him, but I’ve never actually met him. And the request may have been aimed at having me invest in his company, but possibly just asking advice. I’m not sure.

It seems like it might be useful to share my reaction. Leaving out specifics, of course, because that wouldn’t be fair. I hope he doesn’t get mad at me.

I looked at his slides. He does a reasonably good job making the major point about why his business is different, particularly when we consider that he’s doing it just in slides, without the voice narration.

Problem one: The communication vehicle

Most of his slides look pretty good, title and picture, but a few use those annoying “word art” signs that PowerPoint does automatically. It might just be me, but I’m picky about PowerPoint slides. I don’t like bullet points. I don’t think PowerPoint without narration is a good way to present information. Sure, there are exceptions to the rule, but I think PowerPoint is best as background images while somebody talks.

I would have preferred a summary memo.

Problem two: Scenarios

The biggest problem by far is that he is sharing three scenarios. His business needs either $52K or $1.5 million to start. Or, third scenario: he’ll sell the content and not do the business.

One problem with that is commitment: Are you going to build a business or not? What if you change your mind? If you want to build a business, why offer just to sell the content? Somebody invests with you under one scenario, and then an alternative scenario comes up . . . what happens to the investor?

Another problem is that these are very different animals: the bootstrapped business and the $1.5 million initial investment business are night and day different.

Last week I posted here five steps to determining an initial valuation. The first three steps resulted in a specific estimate (just an estimate, but still, specific) of how much money the startup needs. I think you’re supposed to build that kind of estimate. We all know it’s just an estimate, but it’s hard to deal with the ifs and maybes from an investor’s point of view.

One of my absolute favorite people in the whole world was asked by a major VC firm to present his award-winning business. He wasn’t sure how much money it would take, so he decided to ask them what they preferred. Deal killer, for sure.

Everybody knows you have scenarios in your head, on your computer, in the real world. Go to investors with only one plan. Please.

On top of a fence is a very uncomfortable place to sit.

Problem three: Match your strategy to what’s needed

I think it’s very hard to raise $52K in small pieces from strangers. That’s a bootstrapping or friends and family amount. Technically, lots of angels invest in small chunks, but mainly in groups, because there are strength and comfort in numbers. To write a check for $1K or $5K or $10K or $20K or so to somebody you haven’t known for years without a lot of lawyering, and a group, is to have a lot of faith in mankind and the future. You have very little control.

It’s tough, I know, but the smaller amounts don’t work into somebody’s investment strategy. You almost have to know a person well.

Problem four: Ask the right question

Don’t just ask a potential small-time investor to invest. Instead, ask who he or she knows who might be interested. It’s a trick question, easier to ask and easier to answer, but with the same ultimate impact. If s/he is interested in investing, s/he’ll say so. If not, s/he’ll either suggest somebody who might be–still a positive step–or not know anybody. You have something to win, nothing to lose, by asking in this around-the-corner way.

By the way, to my friend:

  1. Finish a single-scenario plan. The $1.5 million one is the only one that investors will care about. If you decide on the $52K plan, revise it to be completely bootstrapped. The $52K isn’t worth having to share ownership. Or revise it to be $250K
  2. If you are looking at $1.5 million, or $250K, then get on Gust or AngelList. Register there, look at the content they have, including tutorials, poke around, see how it would apply to you. Then start looking for local angel investor groups in your area.

Great Relevant Resources on Bplans:

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Tim BerryTim Berry
Tim Berry

Tim Berry is the founder and chairman of Palo Alto Software and Bplans.com. Follow him on Twitter @Timberry.