"Don't reach out to 100 of them at once because you're going to make the initial, the beginner mistake 100 times. Reach out to three of them, make those mistakes and learn. So then you can do a second batch where you're one round a little bit more seasoned and you've learned from the mistakes in the previous few."

"I hate saying this because it has a bunch of biased, unequal consequences as a result. But I'm going to say it because it's actually true. Find a way to get some warm intro... rather than auto-blasting 500 cold emails, it's much better spending the time getting the warm intro to us. Just that channel is so much higher value. And it's a bummer that that's true, but it is true. And if I pretend it's not true, I think it's doing founders a disservice."

"The amount you raise should be a function not of what you can raise, but of how much money you need to achieve the next milestone plus a slop factor because everything is harder than you think... The flying car company I used to work at was funded by Larry Page. I never detected an ounce of sadness that he only owns 3% of Google. The guy's just fine. Don't worry about these crazy things because you get so far over your skis and then you think you'll just do a down round and deal with it. And actually people just walk away."

"People confusing a successful fundraise with success. That's not... a successful fundraise is just raising the bar. You're a pole vaulter and they raised the bar. No one applauds for you at the Olympics until after you clear the bar. So that's what success is. Building a profitable company is success."

"A common thing is they send updates when things are good and they go dark when they're not. I only want the update when things are bad because then we can help. If things are amazing, I'm happy to get no email and one day just cash the check. That would be amazing. That's not how it works. So bring the bad news right away. The good news can be as slow as you want."