Interview with Kirk Ouimet Founder of Scan which was acquired by Snap talks about his spray-and-pray angel investing style leading to 50% IRR.

He makes some really interesting points.

Kirk suggests to invest 20% of wealth in very high risk. Question: anyone know why Kirk doesn't even mention owning a home as part of the remaining 80%? I'm guessing it has something to do with living in SV?

Kirk followed Naval Ravikant in every deal (syndicated) from near when Angellist started, and Kirk thinks that might explain a lot of the 50% IRR.

Following Naval would generally be a great strategy I imagine!

That doesn't mean that if you invest in this manner that you will see the same returns, this may well be a case of survivorship bias or, alternatively other circumstances that make this unique. Angel investing is a lot of work if you do it for the money and just throwing your money at random projects can work if you're lucky but most likely you will not be.

A lot of the returns came from a few HUGE winners from what he said in the pod.

go team - been following along with Wannabe Angels since the beginning. All of the theory behind angel investing is mirrored in pro poker experience. It's the same balance of risk analysis, math & gamble.

You can beat the game in the long run by playing smart (following a lead like Naval) -> but the short term wins and loses are defined much on 'luck'. :)

Could you even imagine doing that many deals?

No and I imagine the K1s are insane

This is fun to listen to for all its counterintuitive observations like not wanting to meet the founders.

But like a lot of angels, it just ends up being a fish story without any real hard numbers or company names.

I don't doubt what he is saying, it's just hard to learn anything from angels when you have no real data.