Hearing a pitch from a startup founder

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Essays

I overheard a team of startup founders pitching their company to a venture associate at a coffee shop this week. I didn’t listen for long because I felt bad, but one thing that jumped out at me, even over my headphones, was that the associate was doing most of the talking, which got me thinking.

The venture pitch is most commonly described as “person who needs money must convince person who has money to give it”. Sometimes a venture pitch looks more like “a person who has money must convince baller founder to take said money over another fund’s”. In both of these cases, it is a highly asymmetrical interaction. Power dynamics are always slanted in interactions between people, but in pitches it is made explicit, and often extreme. I have sat in a number of pitches, pitched a dozen times, and been pitched hundreds of times. The power dynamic manifests in amusing ways, andI want to share my perspective.

As an investor, I want to be a good listener. I want to properly understand the motivations of the founders, challenges and potential of the business, etc. but I also want to demonstrate my genuine interest in the business. After all, a pitch is a two-way audition, and the business and founder are performing, but the investor and firm are, too.

Sometimes, I have to fight the instinct to demonstrate my genuine interest in the business by talking about what they could do, or what they should do. Many investors say that giving business feedback in the pitch is a way to help the founders, but I can’t help but think it’s somewhat self-serving. It feels good to broadly expound on a go-to-market strategy in front of an audience that is trying to impress you. I know this because sometimes, when I’m talking about my own experience or opinion, I’m enjoying feeling and sounding smart, more than being helpful. Real talk. That said, some of the best pitches I’ve been in were filled with feedback in both directions. The founder was honest about how the firm was signaling to the market, and the investor honest about what she liked or didn’t like about the business. And a great way to build empathy is to identify with someone’s experience by sharing your own. But it’s a fine line.**

I got an opportunity to catch up with a great investor mentor a few days ago, and we were talking about all and sundry, and I was struck, as I was describing design consulting, how carefully he was listening, and how surprised he seemed by some of the conclusions I drew. He’s an extraordinarily smart investor with as many years of work experience as I’ve been alive. But he listened like an 8 year old learning about outer space for the first time. And it was so disarming, and I couldn’t help but share how I really felt about it all. It takes real expertise to develop a beginner’s mind, indeed.

** In starting the story with an associate who wasn’t listening and ending with a partner who was, you may want to conclude that partners are great listeners and associates aren’t. Couldn’t be further from the truth. There are plenty of experienced partners who love hearing themselves talk, and plenty of associates who give incisive thoughtful feedback while listening very carefully.

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