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Comment by brianwawok | Hacker News Reader

I was hoping for a fact like

"And this is how I made 42 investments in my first 3 years. All are now bust, and I am out 1.4 million dollars"

Obviously not fun to tell the world how much money you lost, but it would help to add color to the people behind the VCs, that developers love to see as the frenemy (terrible people out to screw you, but man their money is nice sometimes).

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Looking at what other people did and how that turned out is completely useless because the things that matter are the day-to-day details which you can only get by immersing yourself in the process full-time for a long time. So sharing that data would be worse than useless. At best it would serve to satisfy some prurient interests, and at worst it would cause someone to act on what cannot be anything other than hopelessly incomplete data.

But there is one detail I will share with you: I decided to start not in high tech because I thought it was too risky, but to get my feet wet by starting with less risky investments. So I decided to invest in a real estate development in 2006, thinking that even in a worst case scenario there's an asset there that will be worth something no matter how badly things go wrong.

Like I said in the OP, you will be shocked at how things can fail. (And this is far from my only horror story.)

FWIW, I've also had some winners along the way. I'm not poor, just poorER than I would have been if I'd just put the money in VTI.

With hindsight would you take the same path with your career and funds? I find myself at this crossroad right now, both financially and professionally, so found your article useful - thank you.

If you're asking me this question because you hope my answer will inform your decision that's the wrong reason to ask. This is an intensely personal choice, and what you want out of life is very unlikely to be the same as what I do (that's what makes trade possible!) I'm glad I did it despite the fact that it cost me a lot of money because I know that if I hadn't tried I would have regretted it more than I regret the lost money. But that's just me.

Are most angel investors focused on finding the 1000x companies (i.e. the NBT) that VCs are?

I guess my question is what's a practical, good outcome for an angel investor when a company exits? Or what rate of return do the most successful angel investors have?

I was in denial about this for a long time, but the fact of the matter is that your overall outcome is almost entirely determined by your outliers. If you take all of the investments I've ever made, including going to work as an early hire at Google, the I've won. If I leave out Google, then I've lost. If I leave out my single biggest loss, then I've won again. If I leave out my next biggest win, then I've broken even.

Very interesting, thanks for responding.

You bet.

Did "not spending 1 more year as an employee at Google" cost you more or less than all of your later wins?

More. And by a huge margin. Leaving Google early was by far the most costly financial decision I've ever made in my life. But I don't regret it. You have to focus on the money you made and not the money you didn't make or you'll be miserable no matter what happens because no matter how well you do you could have always done better in hindsight.

> Like I said in the OP, you will be shocked at how things can fail. (And this is far from my only horror story.)

Did I miss the story, did you talk about it somewhere?

Paragraph 6 (but no, I did not get into specifics)

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