Stephen Hays

I’ve seen thousands of startup pitches. I’ve invested in dozens of startups. This makes me rather inexperienced versus many industry veterans. Yet, I’ve seen enough to notice a trend.

Just about every startup pitch begins with “why.” Why this problem, why this solution, why this market, and so on. If the founder could just convince the investor with enough data, or enough anecdotes, as to why this matters, then surely the deal will get funded, it seems.

I can’t speak for every investor out there, but for me, “why” is marginally interesting or relevant. What really matters is how the idea sparks my imagination. Does the idea make me start to wonder “what if….?”

The best pitches I’ve ever seen, end in a brainstorming session where the founder and investor say “what if” in a number of contexts, about numerous future iterations of the business plan.

It’s in those enlightening, intellectually stimulating conversations about “what if” that I find myself wanting to partner with this founder, wanting to put time, emotional energy, money, and resources into this business. This is the moment that founders should be trying to get to in a pitch. And it often doesn’t require a standard, dry, boring 12 page accelerator approved pitch.

Fast forward to today, as I think about the essence of my job, I realize it’s a job about wondering, thinking, hoping, guessing, and trial & error. The best part of my job is getting to learn to think in ways I could have never imagined by thinking alongside some really talented people.

So naming this fund was easy. I had this name in my back pocket for several years. I always thought about when I’d get the chance to run a fund named “what if” and let that mantra permeate everything we do.

Thank you for reading — I can’t wait to brainstorm with you!



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