The 2023 Milly Awards: Part 2

You always want to be the second owner of a hotel. You want someone else to go crazy and build it out and then go bankrupt, and then you want to come in and own that. I think the same thing is true with houses. Just go buy a nice house that someone else built.

I bought a podcast player called Castro about five years ago ... I bought the business I was excited about the space, not because I had a plan. And so, the business basically just languished ... I think I bought it for a million bucks, and it just lost $10-20k a month...

So far, Shaan, I've invested about a million dollars into companies via angel investing. I have seen not one dollar back since I started doing it in 2016.

It's not about bad investments you make; it's the ones you miss.

If you think you want to build a house, try it. It really sucks.

I think podcasting as, like venture capital companies, mostly is shit. It's a very hard business, I think, to build tools for.

The hardest part about having a CEO is that they can ruin the business if they're not careful, and you ultimately have to let them make their own mistakes and learn from them.