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I am a junior angel in Silicon Valley. AMA

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Re: I am a junior angel in Silicon Valley. AMA

#142
post #116

Earlier quoted context omitted.

Let me rephrase. Something wider in possibility. When I started delicious, I had no idea that it would someday be a company. Instead it was a thing I wanted to make. But it turned out to be very pregnant with possibility. I'd like to see you do something that is similarly wide. Does that make any sense?

I get you. I'm sitting at home at 3 PM on a Tuesday writing patches to the OSS project that spun out of the day job that spun out of the weeklong project which was supposed to, someday, buy me a video game. We never know what the future holds, right?

We're always creating the preconditions of our own future. At some times more deliberately than others.

What video game?

Re: I am a junior angel in Silicon Valley. AMA

#143
post #119

So far I'm surprised that a) nobody has really asked about exits or returns b) people that have asked questions about their own situations have been incredibly vague c) no questions about background or current work or d) no questions about delicious's creation, founding, and later sale.

Sort of on a): Are non-exit returns ever something you think about? E.g. the possibility of buying into the next craigslist and getting x% cut of some large revenue stream, but never getting an IPO or buyout? Or is that just too uncommon, and/or people with those intentions never cross your radar because they don't seek funding rounds?

I don't know specifics about craigslist, but I haven't heard of anyone who is an investor of a company that pays significant dividends. Not saying it doesn't happen, though.

I suspect that folks who have large revenue streams imminent would go to some effort not to dilute themselves.

Re: I am a junior angel in Silicon Valley. AMA

#144
post #140

I heard you built one website a month, hunting for the right idea, until delicious clicked. Would you ever fund a person you believed in for that kind of exploratory work?

I tried to build something interesting every year. I originally set out to be some sort of expert in social software (I think I succeeded, more or less) way back. In the past I built memepool and geourl and a bunch of other things you've never heard of. However, I never really had the idea of building businesses, just interesting things. I wanted to get attention (I got myself invited to Foo Camp before I did delicio…

I think delicious picked up more users in a day when I left than in its whole first year of existence. So it took some time to figure out if it clicked... however, I know that I spent a lot of time making Muxway (delicious's predecessor) work right for me and had a good sense for what would work for other people.

Re: I am a junior angel in Silicon Valley. AMA

#146
post #145

Has working at Google while being an active investor ever led to any conflicts of interest?

I generally avoid stuff that relies on heavy SEO or otherwise obviously directly competitive. Although I'd avoid some of that stuff merely because it is bad for the ecosystem before I worry if it bothers my employer.

I'm pretty clear where I work and what my burden of responsibility is. So entrepreneurs will end discussions when they learn where I work if I wasn't aware. Usually if there is a conflict issue it ends there.

I invest small amounts relative to my net worth and am unlikely to compromise my behavior for an investment. The E(v) of an investment, if you assume the 33% chance of a > 3x return is still not that big.

Although: Yahoo compliance forced me to pass on the first round of Twitter. Yet another reason I am annoyed at them.

Re: I am a junior angel in Silicon Valley. AMA

#148

Say you have an idea for a web startup, you're working on a prototype in your spare time. How should one make the jump from side project to getting funded? How did you do it with delicious?

Delicious started getting noticed a great deal. Press, etc. I think I had 30-40k users right before I started talking to Fred. This is in the days before user inflation, mind you.

I got several offers of acquisition for delicious in the 250k-500k range, and felt that if I actually worked on it full-time it would be worth more.

I turned down eight or so acquisition offers before I took VC.

Re: I am a junior angel in Silicon Valley. AMA

#149
post #116

Earlier quoted context omitted.

Let me rephrase. Something wider in possibility. When I started delicious, I had no idea that it would someday be a company. Instead it was a thing I wanted to make. But it turned out to be very pregnant with possibility. I'd like to see you do something that is similarly wide. Does that make any sense?

I get you. I'm sitting at home at 3 PM on a Tuesday writing patches to the OSS project that spun out of the day job that spun out of the weeklong project which was supposed to, someday, buy me a video game. We never know what the future holds, right?

[deleted]

Re: I am a junior angel in Silicon Valley. AMA

#150
post #26

Earlier quoted context omitted.

http://en.wikipedia.org/wiki/Kelly_criterion

heh, I just browsed Fortune's Formula and read about Kelly math. Excellent -- it's just like playing blackjack -- gotta control your bank. upshot: if he does well, in a couple years his typical investment size will be $20-$50K. Investment size is a proportion of bank.

It's a good book.

Reading it inspired this: http://joshua.schachter.org/2008/09/amateur-economist.html

Curiously, I was a quant before I did delicious.

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