angel investor

“Angel investors can, in limited cases, have substantive impact on the companies in which they invest. Mostly their impact is marginal, minimum.”

“In fact, if you think about it, if you act like a jerk to a founder, that might be, even if that gets you an extra 50% of your return, your investment back somehow, That might actually cost you way more in the long term because the way you get deal flow is bec…”

“Don't try to be the last money in because you don't have any confidence in yourself. So some of the worst investor behavior is to say, Craig, I like you. I like your company. You're raising a million dollars. I'll put a 100,000 dollars in as soon as you raise …”

“The fact is most angel investors don't get a bite at the later rounds.”

“You need deal flow. Find a way to get deal flow. We'll talk about that. If you don't have deal flow, you'll take the first thing you get.”

“The companies that could be giant are at this intersection of sounds like a bad idea is a good idea. And because That's a very narrow intersection. And because they sound like a bad idea, the best investments are the ones that are easiest to talk yourself out …”

“I think what I have seen the most successful angel investors do is just start helping founders for free. Realizing they may not get to invest in those companies, but that they'll get the referrals down the road.”

“I think value investing is not a winning strategy when it comes to being an angel investor most of the time.”

“If you believe in the power law and you invest that way, excuse me, then what you're not going to do is waste time negotiating downside protection, because what you've realized is that eking out a one and a half X return On all these little investments is not …”

“An A investor, grade A investor gives you money quickly, signs the paperwork quickly, shuts the hell up. That's an A investor. There are very, very few A plus investors in the world. There are very, very many less than A investors.”

“If one of your friends is starting a company, and you would have FOMO if it would become a billion dollar company, just shut up and write him a check.”

“And one thing to look for in your own gut is if you feel more or less convinced the more you talk to the founder. Because it could be you hear about an idea, you see their demo day pitch, and it seems great, and you're a yes, and the more you talk to them, the…”

“If you don't know how much you want to invest and what your budget is, you're probably gonna be making suboptimal decisions. So it's good to think, here's how much I'm willing to invest across a bunch of startups beforehand versus being like, well, you know, I…”

“If it's a very small amount, and you're just part of a large syndicate don't make it hard. It's only going to foul up the process, and often the founders will just push back on all this stuff.”

“Cause it's not, maybe you already saw their deck, or maybe you already read about the company, it's not necessarily about learning what you didn't already know, it's about hearing the founder tell their own story and their own words. And that's such a good rea…”

“Just scheduling meetings in a non-painful way will put you ahead of the pack from a lot of other angel investors. Being on time and picking a convenient location will put you ahead of the pack versus most angel investors.”

“I think most angels actually care too little about valuation. And so often if you actually look at the return, say you do 10 investments, and I'm making up a number just to make it a round number, a 100,000 each, and nine of them go under and one works and tha…”

“Find, find people who work at startups, and ask them to introduce you to their investors. That's the way to do it.”

“When you're a good founder, oftentimes you know other good people, and the opportunity you have to give them money requires almost no time or effort, and so you just, and like, if you're a good founder, oftentimes people are offering you Deals. And so like, yo…”

“The prizes that you win playing the game is congratulations. Now a bunch of your money is tied up in illiquid investments that may or may not show up. So now maybe you're like financially strapped. Maybe you're worried about other stuff. You're worried about y…”