angel investing

“We have collected 12 different academic studies on angel investing, which show median returns of 18% to 54%.”

“You really have to do a lot of investments based on the power law, which is that one company out of your portfolio will probably return your entire portfolio. And you have to think that every company you invest in is going to be that company that returns your …”

“First rule of thumb, follow smart people, right? Because just like in sports, in the Tour de France, if you can keep up with the smart people, then you can just draft behind them.”

“This whole angel investing phenomenon is partly due to this Vanguard S&P 500 and the way the public markets are working. So people that call this a bubble I don't really understand the full scope of money and money flows and the whole ecosystem of investing, b…”

“It's the kind of thing most people shouldn't really be doing expecting a financial return.”

“As long as it is from your network, and as long as it's a very minimal amount of time, it ends up being not that distracting at all, so I would disagree with that. I think that there are a lot of top-tier investors that encourage their founders to do this.”

“I frankly think that that leads to trend chasing, which is very, very challenging, and I think trend chasing and angel investing is tough.”

“I believe that angel investing, seed investing is a completely different thing than venture capital. I don't think it's part of venture capital. I think that it's a different type of asset, which has different needs and requirements and has a different perform…”

“I really enjoy angel investing, but you know, sometimes you're one of many and you're not necessarily that one call that the founder has for any given thing.”

“I don't think naturally I'm actually that good at fundraising, but when you can understand how the other person's thinking and what are red flags, what are gray flags, green flags, I think it kind of helps a lot because you just, you know, when someone asks a …”

“I think it personally removes focus. It introduces another thing to worry about, but more importantly, I think it drives a potential wedge between kind of a founder and the rest of the team.”

“Just from a pure numbers perspective, if there are nonlinear returns on an investment, you probably need to make, as an angel, 10, 20 investments to possibly see, to have a statistically high chance of seeing one of these nonlinear returns.”

“The point you made where you don't know some of your riskiest bets, maybe the absolute best bets. And I realized that, you know, some of the riskier bets I'd done smaller check sizes on, and I realized that was actually not the right decision. And the risky be…”

“I think what most people fail to understand is that it's extremely risky. I mean, you probably have a better shot at going to a casino and winning roulette than making money angel investing.”

“One of the simple questions I always ask myself from my perspective as an angel investor is, can this potential company get to a hundred million dollars of annual recurring revenue? And there's a few reasons behind that. I think number one, that's the point at…”

“You want to be an easy check and easy doesn't mean you're stupid. It doesn't mean that you write checks for everybody, but it means that you're not trying to take 10 meetings to write a 25,000 dollar check.”

“I think for most people, it's finding the time to get to know others, to be out there in the Twitter sphere or wherever it is where people are talking about ideas. I think finding the time to really get to know the problem space and the team once they've engag…”

“So angel investing absolutely is a distraction. I think if you as a founder, like run your own like seed fund and raise capital on the side while you are building your own product and business, I think it's a massive distraction.”

“In other companies, like I could rely on my rate of execution, you know, like my speed, my learning loop, but now it's become this different element of, I'm really trying to gauge how quickly they learn, how quickly they execute. And that's like the biggest fa…”

“The angel investing model and the solo capitalist model doesn't do a great job of supporting portfolio companies, right? So in order to compete with traditional venture firms that have a lot more resources, And areas of support and areas of like business devel…”

“Number one principle of my angel investing is solve for minimizing time, not maximizing return.”

“So, so I wrote the same check size every single time, and the reason that I did this was You know, I think you can get into a trap of altering the check size based on your conviction, but the reality is like at this stage, the angel stage, they're all super ri…”

“I don't invest. I don't do any kind of angel investing.”

“The time range on seed investing on the angel side is just, is like a decade plus.”

“And so I try to do the investing thing and, you know, I do some investments, but it does not derive me the same amount of amount of joy than, Then actively building something.”

“And I just do 25 every time. Every time I'm 25.”

“If your job is to learn and to demonstrate you add value, then just write small five K checks. I see so many people that never start angel investing because they think they have to invest 200 K at a time. It's crazy. If you believe you've got to learn, you wan…”

“Angel investing, I think, is very distracting to founders.”

“So I stopped in 2015, which also allowed me to double and triple down on the podcast, which was born of the burnout of the four hour chef.”

“I would say, like, maybe it's 70% angel investing, could be 80, 20% podcast, 10% books.”

“And when I write a check as an angel investor, I would just mark it to zero. I don't care. I just assume that it's a zero. And then that way I don't worry if it fails.”

“Once you see the world from the perspective of the angel investor, you realize that we really don't care. Even a three X, like if you take my spreadsheet and this investment made three times the money, like the founder is very proud. Like, Hey, I made you thre…”

“The amount of learnings that you get from being an investor is insane, because it's essentially you build your own intelligence. As you receive investor updates, you understand how the market is moving. What are the valuations? What are the multiples? What kin…”