Should you ever talk smack about your competitors?

Almost never, but here's when you should

In general, talking smack about your competitors makes you look defensive and weak. But there is one exception:

If you’re David and they’re Goliath: lean into that narrative. Everyone loves to root for the underdog.

Even if the competition is somewhat manufactured, it can still be a compelling story. In the world of databases, no one is really cross-shopping MySQL vs Oracle, but that was a much more interesting story than MySQL vs Postgres.

The more you antagonize and irritate your Goliath, the more you get talked about, and the greater the chance that they end up acknowledging you in some way—which only adds to your legitimacy. You have nothing to lose and almost everything to gain.

If you’re David and they’re also David, say as little as possible about them. The more you acknowledge them, the more powerful they become. Give them no airtime. If you have to give them any airtime, keep it brief and complimentary.

As a concrete example: a new “tech-enabled accounting” company crops up every year, all of which are attempting to directly compete with Pilot. I literally never mention their names.

If asked directly, here’s the most aggressive thing you can get me to say (pay particular attention to the last part):

“The biggest difference between Pilot and [X] is our size and scale: we're the largest startup-focused accounting firm in the US, by far. And that scale actually gives you some structural benefits that you just can't get from a smaller provider—in particular, there's a ton we can do for you under one roof: bookkeeping, tax prep, R&D credit, CFO services, controller services, AP/AR, payroll help, etc. etc.

You're not going to need all of this on day 1, but as you grow, it’s helpful to be able to get this all under one roof from us. Said another way: we're the last external accounting firm you need to hire before you (eventually) bring the function in house — and that isn't true of a smaller provider, which you will eventually outgrow.

So you should think of going with Pilot as a form of futureproofing.

I think highly of [X] and the [X] team—they’re smart and I’m sure they’ll do a great job. But there are real, structural benefits to operating at our scale, and you can’t get those benefits from a smaller firm.”

Finally, if you’re Goliath: find a way to change the narrative ASAP. As a startup, you never want to be Goliath.