I've had one brief interaction with Gary a long time ago, and he's been a role model ever since
I had a difference in opinion with my cofounder and wanted to leave the startup we'd founded, even if it meant leaving the YC program (which I adored), and would likely lose my visa to stay in the US. Seeing how distressed I was, Gary took me aside somehow simultaneously made me feel heard, but also told me that it's up to me to come back stronger from this moment.
It made all the difference to me, and I've thought back to that moment many times in the years to come.