I know how to sit with a founder in her hardest moment without flinching. That is one of the most specific and valuable things building has ever given me, and I use it in service of every founder I advise.
The flinching is what most people do in someone else's hard moment. Not from callousness, from discomfort. Being with someone in the full weight of their worst chapter requires you to have been in your own. If you have not, the other person's pain activates your avoidance.
What flinching actually looks like
You move past it too quickly. You offer the reassurance that is really for you. You reach for the silver lining that softens the moment before it has been fully held. It looks like support and it is actually self-protection, and the founder on the other side feels the difference even if she cannot name it. She feels slightly alone in the exact moment she most needs not to be.
You cannot hold someone in the worst chapter if you have never been willing to stay in your own.
Why having lived it changes the room
I have been in my own hardest moments completely. The lawsuit. The ICU. The loss. Having been there and found my way through means I can sit with another founder in hers without needing it to be smaller than it is. I can hold the full truth of it with her. And from that specific quality of presence, the presence of someone who has been there and stayed, something shifts. She knows she is not alone, and from not alone, the way through becomes visible. That is the gift the build gave me, and I give it forward every day.