Flipping My Script

Posted on November 2, 2021. Filed under: Uncategorized |

Often times when I meet a founder for the first time, the path of least resistance is to follow a standard intro pitch format. Often times a founder will show up, eager to jump into the slides they’ve prepared. Rarely, if ever, do i enjoy this path. I like to focus intro conversations on things i actually want to explore. And the generic competitive matrix slide ain’t one of them. Sometimes I’ll guide a conversation with the following prompt: “I’m always interest in genesis stories, so would love to understand the experiences you’ve had along the way that input to you dedicating your life to this company and I’d love to understand what your initial hypotheses were when starting it, which of those you’ve validated, which you’ve invalidated, and how those learnings inform the trajectory on which you are now orienting the company.” It’s genuinely what i want to know and if someone is willing to engage with that format, you can cover a lot of ground in 30-45 minutes.

I just reread this excellent post by Graham Duncan which is one of my favorite pieces of writing on the internet, and it occurs to me that such a prompt, while efficient, might be routing founders toward a headspace and analytical cut at their business which misses the upside. This prompt doesn’t really lead to the “what if everything goes right” version of the future, which is the question i tend to ask myself when something clears a more analytical initial filter. The flaw in the initial prompt is that I am forced to ask that best-case question ex post facto, in isolation, without the input of a founder.

I think I’m going to change my prompt. The new prompt I’m going to try is “if there were one thing i needed to understand to see as much value in your business as you do, what would it be and let’s talk about that.” I think that question will orient toward the upside thinking that is essential in building conviction. There’s plenty of time after the fact to dissect and analyze, and frankly most of that can happen async, but i sure wouldn’t want to miss the sliver of what’s possible that a founder sees in her own business.

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2 Responses to “Flipping My Script”

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Oh I like this prompt a lot. Gonna need to add this to the repertoire along with Vaughn Tan’s “How do you assess ‘quality’?”

On Tue, Nov 2, 2021 at 12:34 PM Jordan Cooper’s Blog: startups, venture capital, etc… wrote:

> jordancooper posted: ” Often times when I meet a founder for the first > time, the path of least resistance is to follow a standard intro pitch > format. Often times a founder will show up, eager to jump into the slides > they’ve prepared. Rarely, if ever, do i enjoy this path. I li” >

Exactly why from the start, you and Pace have been our first choice. Of all the investor meetings we’ve had most investors spend the whole time trying to stump us. Like we haven’t thought of everything from every angle working on it for 7 months. They all look for reasons it won’t work. Obviously, it’s hard – but hard isn’t the same as impossible. I feel like investors have gotten lazy and forgotten the “venture” in “venture capital”. If on the small chance it works, what’s the upside? Thanks for being the one to imagine the future that doesn’t exist yet with us!


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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at Jordan.Cooper@gmail.com (p.s. i don’t use spell check…deal with it)

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