"I actually think the part that people over-index on is TAM slides. The reason they do that is it's a very academic way of proving the TAM. What we're actually trying to understand is the why now. That's the most important slide... The TAM slide is a rudimentary approach to articulating why there will be market pull. What you're saying is there are dollars here, but that's not really telling us we can take them for this reason."

"If we've gotten through 15 or 20 minutes of the meeting and we still don't really understand what makes the company or the team or the approach unique, that critical insight is often very hard to recover."

"I encourage founders to ask, if you as an investor have pinned conversations in your messaging apps, like text, iMessage, Signal, whatever, how many of the founders you work with are pinned at the top? Meaning how much do you actually work with your founders? Because I think that that's a very direct way to understand how they view their relationship with the founders."

"Lowest priority would be cold message, boilerplate, no context, just like here's who I am and that's it. That's gonna be very hard. Second best would be here's a cold message but there's context, it's customized for that particular investor, there's a unique insight... I personally will still answer many, many cold messages as long as they're customized."

"People assume that finding product market fit is a one and done, that it only happens one time and then that's it. The reality is you need to find product market fit repeatedly... Companies built 20, 30 years ago, they're transitioning to be AI companies and they're still struggling now, obviously with the benefit of distribution, but they're still fighting to find product market fit."