Here’s How to Impress Investors with a Perfect Fundraising Pitch

Hint: investors are never impressed by entrepreneurs who are “crushing it”

Photo by Austin Distel on Unsplash

When I was first learning to fundraise, I believed I needed to convince investors of two things: 1) that my startup was awesome; and, 2) that I was an exceptional entrepreneur. In my mind, the best way to accomplish those two things was by learning how to give a perfect fundraising pitch.

I read countless articles about how to pitch investors. I spent hours practicing my pitches in front of trusted mentors. I even recorded myself giving my pitch, then I would dissect the videos like a golfer who records his swing then analyzes it for flaws.

Thanks to all this practice, I entered every fundraising pitch prepared to “wow” investors. I had a polished pitch deck. I had a killer demo. I knew exactly what I was going to say and how I was going to say it. I even had perfect “entrepreneur-casual” outfits (i.e. faded jeans, t-shirt, and a blazer). I thought if I looked like an entrepreneur who was “crushing it” and talked like an entrepreneur who was “crushing it,” investors would believe I was “crushing it” and they’d want to invest.

But I was wrong. Even worse, it took me years to figure out how wrong I was because, aside from not raising any money, the feedback I was getting from investors was all positive. Investors praised the quality of my pitch. More than a few told me I had the most beautiful pitch deck they’d ever seen. I even had one investor try to hire me to advise his portfolio companies on how to give better pitches. But not a single one of them invested in my startups.

So what was wrong? If I had such a great fundraising pitch, why did I spend years struggling to fundraise?

When things are too good to be true

I finally solved my problem during a fundraising trip to New York. After a day of unsuccessful meetings, I was hiking back to a friend’s studio apartment and the couch he was letting me crash on. While waiting for a crosswalk light to change at an intersection in one of the city’s seedier neighborhoods, I pulled out my phone to look at a map. As I did this, a scruffy man walked up and asked if I wanted to…