Do not over-optimize for price. Startups are binary. When I say that, it either exits or it does not exit ... The difference at the end game is if you made $100M—'Well, if I didn't take that dilution, I would have made $119M'—it doesn't matter. If [it] really mattered, you wouldn't live in fucking New York; you'd go to Florida.

When you read a room in investors, if they do not respond in 24 hours, they are not interested ... I will take any signal of investor interest within 24 hours. It could be a retweet. It could be they checked out my LinkedIn profile. Ideally, they email me, thanking me, asking me follow-up questions.

The whole goal... if it's an hour, get through the story in 25 minutes, ideally, so that the rest is just discussion ... If you're all the way... and you're barely going to the last slide, it's not going to work. You have to finish early, which means you were concise—20 slides, 25 minutes, ideally like 17/16 slides, 25 minutes.

The pitch... It has to be simple ... You don't need to do the intricacies and use all these bullshit web terminology. Forget the terminologies. What does the product do? And let me visualize it so that I can tell the story to my partners and understand it and give you money.

The worst thing for your pitch is numbers. Everything is worse once you actually have revenue ... If you tell people—I hate this—like, 'Oh, I'm a seed company. Here's my revenue in five years,' I know you're making shit up.

There will be moments in the business where the highs are highs... and the lows are low. And you want the person who's going to be supporting you and not just thinking about the money—because the moment they start thinking about money, they don't care about you, and they make the worst decisions...

If you look at today's culture, we have two sides. People just automatically pick a side, like human nature. And if you know what you are and you own it, people respect that way, way more.

What I say is fundraising is... the world used to be like this; the world now has this. I'm building this thing that's taking advantage of this, and this is how the world will be over here.

Nothing ruins a raise better than numbers. Just remember that: Nothing ruins a raise better than numbers...

Less is more. Every deck... 20% less words. Nobody wants to read.

It depends on the investor. Some investors love that you have advisors; I hate it 'cus it's bullshit, unless it's real. If it's somebody I know or somebody who truly has that insight or has the connections that can accelerate that business, it's the cheat code.

I've done somewhere, like, 150 rounds I've helped raise. Each round, on average, is 100 'Nos.' Okay? 70 to 100 'Nos' for every single 'Yes'

Raising money is fairly easy to me now, mostly because it's repetition. I've had somewhere between 7,000-8000 minutes at this point.

Raising money, for me, it is not personal when someone says no; it's just not for them. That's okay.

Spend the time doing diligence. It's crazy that not enough people check references ... People behave the way they are all the time. So, find the people that they aren't telling you about.