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.”

Everyone starts their fundraising the same way:

1) Open a shared Google Sheet.

2) List all the VCs you've ever heard of.

3) Ask a bunch of people who they know.

4) Find out very quickly this isn't very effective.

Making sure that the next generation of investors is far more representative of the population at large than the current one is really important to me--but that won't happen unless we support the handful of folks that are already here, and do everything we can to make them successful.