Does the “no” ever get less awkward?

This is my third startup. The “no”s don’t sting any less this time around.

330 words • 2 min read

Pilot is my third startup. My first startup, Ksplice, was acquired by Oracle in 2011, and my second startup, Zulip, was acquired by Dropbox in 2014.

When we were running our first startup, we knew nothing about anything, and learned a lot as we went. In particular, I learned a bunch about how to sell, and I vividly remember the anxiety I’d feel before asking for a sale—and the corresponding disappointment if the prospect ended up not moving forward.

At a recent event for startup founders, a first-time founder asked me: does it get easier now that it’s your third time around? Do the rejections sting any less now?

The answer, unfortunately, is “no.” Asking for the sale is still hard. Each time a prospect doesn’t buy, it’s a bummer. Each customer that doesn’t have a delightful experience still feels viscerally painful—and like a very personal letdown. The fact that this is our third startup, or that we serve thousands of customers, doesn’t change any of that.

And that’s not a bad thing. Caring is good. That passion is what’s going to make you continually improve your process or product, which, in turn, will cause the business to be successful.

The thing that does change as you grow is that you have more context. No one wins all the time. A best-in-class win rate for a sales rep is something like 25-30%. Meaning: you’re mostly losing all the time. And that’s OK—that’s part of the process. Knowing that you’re not unique in the journey does make it feel better.

More importantly, you’ve learned how to use the loss constructively. I’m never excited to lose the sale, but if I know why I’ve lost it, and what I can do going forward to avoid this particular category of mistake in the future, then I’m at peace with it—I’ve learned from it. The losses that still drive me crazy are the ones where I don’t feel like I understand why I lost.