I’ve made over 100 investments in my career and nearly half of those went into diverse teams.

I’ll be the first to back up the notion that diverse founders have just as much ambition, drive, intellectual horsepower, creativity—you name it—than anyone else. In fact, you could make the argument that, because of their lack of advantages in other areas, the ones who make it to a venture pitch actually have more of these raw ingredients because they’ve had to in order to make it to the same destination as their straight white male counterparts.

There is, however, an advantage that some founders have over others that I hate to admit exists—but one that I would very much like to solve for.

“Israelis & Palestinians do not deserve the consequences of evil forces that drive those who make decisions, profit from conflict, and push hateful rhetoric that make people lose their consciousness.”

This was a very powerful sentiment that I wholeheartedly embrace found in a very difficult to read (warning) Instagram post about the horror of the Hamas terrorist attack on October 7th.

This post is about considering the costs of war.

What complicates the answers here is that there are some types of content that can live in multiple places (like a video) and others “types” that are so specific to a place that they’re expected to have a particular format (a TikTok video), yet they can still be transferred to other formats (a link to a TikTok video in an e-mail or placing that video on LinkedIn).

That makes trying to create a very simple-to-follow set of rules… well… not so simple. You can’t easily say that all video interviews should just go on LinkedIn because that’s the best platform or that Twitter is the best place for daily commentary on the tech world.

When you’re asking for a one-on-one, you want the other person to feel like this is going to be a thoughtful and interesting exchange with someone who has already done a bunch of work before they’ve gotten to you. They’ve exhausted all the ways they could simply Google, Tweet, or post asks on LinkedIn for the information, and put most or all of those things into practice.

“How much should I ask for?”

Almost every single time I talk to a founder as they’re prepping their raise, this comes up—and it’s absolutely the wrong way to think about a round.

The right question is, “How much do you need?”

In the case of VCs not liking solo founders, there are lots of counterexamples of successful solo founders, so it’s not like anyone has proven that you can’t win this say. There are, however, legitimate concerns that a VC might have with your team generally that the presence of co-founders might solve, but doesn’t always.

Either VCs can identify a very specific, unassailable issue of specific risk they don’t believe the return is there for, or they’re just being lazy.

You should never let a VC off easy by letting them lazily paint a whole industry as a terrible place to invest. For everyone who’s ever said that travel sucks, music sucks, or e-commerce sucks there’s an Airbnb, Spotify, or Shein that has bucked the trend—and isn’t that what VCs are looking for? Outliers?

It is completely natural to assume that the other person loses interest in the one thing you can’t control. You’d literally have to be the lowest ego, most self-aware person in the entire world to think, “You know, objectively, I’ll bet my growth isn’t really in the top 5% of companies that this partner at a highly visible firm is seeing. I’ll bet that’s why they’ve lost interest.”

I also think the language of VC is highly confusing.

Investors say things like, “We’d be interested in writing a $500k check.”

Weirdly, what they really mean is, “If we were interested, we’d be interested in writing a $500k check.”