October 22, 2023

It's common knowledge among startup founders that everyone is putting out fires all the time. Even if a startup seems to be doing extremely well from the outside, it's highly probable that the founder is battling several problems all at once.

Still, when meeting founders we haven't met before, or when joining a new group, we often paint a rosy picture of what we're going through. This is not deliberate or disingenuous — rather, it's second nature as a result of being in front of investors, customers, your team, or potential hires all the time. As a founder, you're always selling.

Exposing our vulnerabilities is difficult, especially when meeting new people who you assume are all doing better than you. This greatly diminishes the value you can get out of being in the group — since you're not showing others the reality, it's impossible to ask for help. I picked up this trick from a friend of mine to overcome this. When joining a new group of people (and I'm using founder groups as an example because I've been a founder for the last 9 years), start by sharing what's going wrong. Make it part of your introduction.

It feels good to lead with 'we're doing $Xm in ARR and grew Y% last quarter', but 'we're doing $Xm in ARR and grew Y% last quarter, but we've had a lot of churn last month and I'm still not confident we have PMF' is going to help you get better advice — and empathy.