I tend to anticipate with a small group of investors, even acknowledging the risk of doing it too early. In my view, the benefit of having a tight board of high-quality investors challenging the opportunity early often outweighs the downside. It sharpens the thesis, surfaces blind spots, and helps avoid spending too much time on the wrong deals. That said, I don’t socialize everything. I usually wait until there is a clear initial fit (sector, size, basic economics, and deal dynamics) but before going too deep into diligence.

It depends (terrible answer, I know). The way I approach it is that I try to share with them the deals early on to surface any frictions or concerns before I spend too much time on it. That being said, in my case there's a small number of investors who are close and available, so getting their feedback on deals early on is helpful and helps me focus on their concerns as well. If I had a large number of investors who have less availability, I would probably wait until I feel confident that it's a good opportunity before socializing it.