I Promise He Wasn’t That Crazy On The First Call

James Shomar
Feb 9, 2019 · 4 min read

It’s never a good sign when after a call with an entrepreneur one investor says to the other “I promise you he wasn’t that crazy on my first call with him.” That’s actually a direct quote from me earlier this week. Now I don’t bring this story up just to poke fun at an entrepreneur, far be it from me to ever do that. There would be no StartFast without the incredibly talented, driven, and passionate founders we work with.

I wanted to highlight this story because it epitomizes a very common trap entrepreneurs fall into when pitching their business to the outside world (not just investors). Founders are always straddling this difficult line between being imbedded in the weeds of day to day operations while at the same time carrying with them a large and often abstract vision for the company. That means when they’re describing what they’re doing to people on the outside one of two things usually happens: 1) they dive too deep into the details in which case everyone gets lost without context, or 2) they jump to their higher level vision in which case no one can wrap their head around what your company looks like in the real world.

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I actually prefer the first situation to the latter. In both cases, we need to hit the brakes a bit for anyone to actually understand what your company is, but in the first case at least I know the entrepreneur has their finger on the pulse of the business.

The latter case tends to be where most of the “interesting” personalities come to light. I always say it takes a little bit of crazy to be an entrepreneur but sometimes you meet someone who takes that a bit too far. It’s never a good thing when a pitch turns into an hour long abstract lecture about social media’s impacts on society. By the way, the investor’s response to me was “He’s the most interesting person he’s ever met.”

In the second case, entrepreneurs need to spend less time thinking about their business as Amazon in 2019, and more time thinking about their business as Amazon in 1994. It’s great that entrepreneurs have a big vision for what the company could become but the pitch today should start as simple as “selling unique book titles online.”

The best way to kick off a pitch whether to an investor, customer, etc. is to set some kind of context before diving in. To do that, there are many simple templates from which to draw inspiration. For instance Steve Blanks XYZ: “We help X do Y by doing Z”. Let’s use an example from a StartFast portfolio company LotMonkey. “We help auto dealers sell more cars faster by creating more effective with car-lot merchandising (decals, banners, hang tags, window stickers, etc.).”

Let’s try another one, Eric Sink’s “Why, What Who” Superlative: Why choose this product? Label: What is this product? Qualifiers: Who is the audience? Again for LotMonkey: “The most effective car-lot merchandising system for automotive dealerships.”

For good measure let’s try another, what I call Geoffrey Moore’s mad lib.

For____________________(target customer)
who___________________ (opportunity)

(company name) _________ is a ________ that ________________(benefit statement).

Unlike__________________(competitor)

who____________________(differentiation statement)

Proven by _____________(studies, testimonials, social proof, etc to prove your claim.)

“For automotive dealerships who are looking to sell more cars, LotMonkey is a car-lot merchandising system that helps dealers better package their inventory to sell cars 12% faster.

Unlike traditional automotive print shops who are expensive, require a lot of design input from dealers, and take a long time to work with, LotMonkey’s success is proven by inventory management data from over 100 current customers.”

Does that fully describe their business? No, there’s a lot more going on under the hood. The point is in any case it’s a digestible description that kicks off a conversation. The goal of the entrepreneur is to ease the audience into the water one step at a time not kick them into the deep-end and hope they can swim.

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James Shomar

Written by

Tech Entrepreneur | Investor | Autocross Racer | Program Director https://startfast.net

The Startup

Medium's largest active publication, followed by +721K people. Follow to join our community.

James Shomar

Written by

Tech Entrepreneur | Investor | Autocross Racer | Program Director https://startfast.net

The Startup

Medium's largest active publication, followed by +721K people. Follow to join our community.

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