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The Bechtolsheim one had some great info.

http://images.businessweek.com/ss/10/02/0225_angel_investors...

> As an angel investor, he’s famous for cutting a $100,000 check to Google’s founders even before they had chosen their now-famous name. In an e-mail, Bechtolsheim confirmed that the check has netted him more than $1 billion.

> Bechtolsheim also expressed a sober perspective on the emergence of former Google employees as angels and entrepreneurs. "When people are part of a new company that gets very successful very quickly, such as Google (but this effect is by no means limited to Google), they sometimes confuse the root of this success and incorrectly assume that the success was due to their own actions. They then want to translate this experience to other opportunities, either in the same or in related spaces, which in some cases may turn out, but in most cases will fail, just like the majority of all VC investments fail. … The only thing different about the Google mafia compared to other similar periods in history is that more money was made at Google by more people (and more money will be lost here)."

Similar statements could be made about the PayPal Mafia: http://en.wikipedia.org/wiki/PayPal_Mafia
Except ex-PayPal people have been quite successful, by and large. What's the biggest Xoogler success?
Probably Friendfeed
Twitter?
That's technically true, but not quite what I was thinking. Let's define Xooglers as people who were pre-IPO at Google. Or even just people who didn't originally come to Google through the acquisition of another company.

How about in that case?

I'll tell you another story about Andy Bechtolsheim: he invested in a competitor of my startup about 10 years ago, would never give us the time of day when we tried to raise money. We never got to pitch to him, which is unfortunate considering that he was the one angel specialized in our space. Fast forward 5 years, we acquired the company he had invested in.

Who you know (or rather, who knows you) matters. We were out of towners at the time.

So true, look at the xooglers getting reaquired by the mothership.
"Who you know (or rather, who knows you) matters."

Yea, if Andy had known you guys well enough to understand that you would kick the other's company's butt and acquire them, he could have just invested in your company directly and got a better return. :)

I wish these sites would take the time to populate the title attribute for images so you can mouseover and see the name before clicking.
They could crowd-source it or pay some mturker.
You miss that the point is to get a clickthrough. Bs publishing tactic
It would be interesting to get some numbers on YC's returns/investment ratios.
It sure would. But we've been operating such a short time that all the acquisitions so far have been early acquisitions, which are always for small amounts.

I'm pretty sure we're ahead on paper, but I've never tried to calculate how far ahead.

Strange. I'd expect more accounting and number-crunching.
There are thing we measure, but not unhatched chickens.
OK.

Too bad the transaction costs are so high. I guess their would be ample opportunities to invest relatively small sums in newish companies, based on some statistics about them.

Isn't one of the advantages of scaling investing the ability to count unhatched chickens?
Not enough public info to really judge, but anecdotally they're doing very well.
YC is probably two or three intermediate value (35 mm) highly probable acquisitions away from a 100% ROR, assuming 2.58 million invested thus far (129 companies * 20 k avg investment). Between loopt, scribd, jtv, et al they'll easily clear that barrier. This is assuming they're at breakeven now.
Interesting that pg is second only to Ron Conway, in number of investments (I'm guessing this is YCombinator vs. Ron Conway Inc.) 190 vs 129 given that YC has only been doing it for 5 years.

EDIT: link to table: http://bwnt.businessweek.com/interactive_reports/future_of_t...

I don't know where they got that number. The current number is 172. Last June it was 144.

The number for Ron also seems wrong. He's made a lot more than 190 investments. He's been doing this since the 1980s.

2004 onwards was the time frame.
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The list of top angel investors.

No. 1

Chris Dixon, 38 Co-founder, Hunch Chris Dixon’s blog

No. of angel investments: 23 Companies funded (a sampling): Skype, Postini, Milo.com, Knewton, DailyBooth

No. 2

Ron Conway Investor

No. of Angel Investments: 190 Companies funded (a sampling): Google, Facebook, bit.ly, Digg, Mint.com, Twitter

No. 3

Reid Hoffman, 42 Chairman, co-founder, LinkedIn Reid Hoffman’s LinkedIn profile

No. of Angel Investments: 49 Companies funded (a sampling): Digg, Facebook, Flickr, Friendster, Ning, Zynga

No. 4

Esther Dyson, 58 Investor

No. of Angel Investments: 60 Companies funded (a sampling): 23andMe, GridPoint, del.icio.us, Flickr, Meetup

No.5

Peter Thiel, 42 Founder, President, Clarium Capital Management

No. of Angel Investments: 26 Companies funded (a sampling): Facebook, Friendster, LinkedIn, Yelp, Zynga

No. 6

Marc Andreessen, 38 Investor

No. of Angel Investments: 53 Companies funded (a sampling): Business Insider, Digg, LinkedIn, Qik, Scribd, Twitter

No. 7

Jeff Bezos, 46 Chairman, founder, Amazon.com

No. of Angel Investments: 18 Companies funded (a sampling): 37signals, Google, Linden Lab, Social Gaming Network, Twitter

No. 8

Chris Sacca, 34 Managing Director, Lowercase Capital

No. of Angel Investments: 32 Companies funded (a sampling): bit.ly, FanBridge, Gowalla, Posterous, SimpleGeo, Twitter

No. 9

Mike Maples, 42 Investor

No. of Angel Investments: 39 Companies funded (a sampling): Circle of Moms, Digg, Kongregate, Odeo, Twitter, Weebly

No. 10

Andy Bechtolsheim, 54 Founder, Chairman, Chief Development Officer, Astra Networks

No. of Angel Investments: 49 Companies funded (a sampling): Brightmail, Google, Granite Systems, Nvidia, Tapulous

No. 11

Paul Graham, 45 Co-founder, Y Combinator

No. of Angel Investments: 129 Companies funded (a sampling): Bump Technologies, FanChatter, Heyzap, Justin.tv, Scribd

No. 12

Max Levchin, 34 Founder, Chief Executive, Slide

No. of Angel Investments: 7 Companies funded (a sampling): Evernote, MixPanel, Raptr, Slide, Yelp

No. 13

Aydin Senkut, 40 Founder, Felicis Ventures

No. of Angel Investments: 65 Companies funded (a sampling): Foodzie, Mixer Labs, Rapleaf, The Auteurs, TwitVid

No. 14

Bill Joy, 55 Partner, Kleiner Perkins Caufield & Byers

No. of Angel Investments: 24 Companies funded (a sampling): Blazent, NeoPath Networks, Dantz

No. 15

Kevin Rose, 33 Founder, Digg Kevin’s blog

No. of Angel Investments: 12 Companies funded (a sampling): Twitter, 3Crowd Technologies, Foursquare, SimpleGeo

No. 16

Dave Duffield, 69 Founder, Chief Executive, Workday

No. of Angel Investments: 18 Companies funded (a sampling): Acta Technology, Bridgestream, Netcentives

No. 17

Andrea Zurek, 39 Founding partner, XG Ventures

No. of Angel Investments: 26 Companies funded (a sampling): Lotus Vodka, Facebook, Red Mango, and Vaxart

No. 18

Marc Benioff, 44 Founder, Chief Executive, Salesforce.com

No. of Angel Investments: 9 Companies funded (a sampling): Mashery, Qik, Tapulous, Zuora

No. 19

Jeff Clavier, 42 Founder, Managing Partner, SoftTech VC Blog: Jeff Clavier’s blog, Software Only

No. of Angel Investments: 52 Companies funded (a sampling): bit.ly, Circle of Moms, DNAnexus, Mint.com

No. 20

Caterina Fake, 36 Co-founder Hunch Caterina’s blog

No. of Angel Investments: 6 Companies funded (a sampling): Etsy, Maya’s Mom

No. 21

Martin Varsavsky, 49 Founder, Chief Executive, Fon Martin Varsavsky’s blog

No. of Angel Investments: 28 Companies funded (a sampling): 23andMe, Dopplr, Eolia, Joost, Plazes, Tumblr, Wikio

No. 22

Naval Ravikant, 36 Founder, Chairman, Vast.com Blog: Startup Boy

No. of Angel Investments: 21 Companies funded (a sampling): Chatterous, DotSpots, Fluther, Twitter, Vidly

No. 23

Joe Kraus, 38 Partner, Google Ventures

No. of Angel Investments: 5 Companies funded (a sampling): InfraSearch, Linkedin, Napster, Odeo

No. 24

Eric Schmidt, 54 Chairman, Chief Executive, Google

No. of Angel Investments: 9 Companies funded (a sampli...

How can Ron Conway not be at #1?
There's a detailed table of the rankings: http://bwnt.businessweek.com/interactive_reports/future_of_t...
They should have included astrological information ;)
I find that list really dubious -- it's very hard to believe that 97% of Ron Conway's investments have worked out. The only way I can imagine that being true is if there are strings pulled so that there's a fire-sale at the end that's being counted as an exit.
97% are "not dead"

I also find this hard to believe.

I've invested in ~ 20 companies over the last four years.

- Two are insanely good, but no liquidity yet - One appears to be dead - One has been acquired

The rest are in various stages of growth.

Right, as Paul pointed out, the numbers for Conway are way low (maybe these are just the SV Angels numbers?), but over the course of Conway's investments in the last 20 years, it's astronomically unlikely that 97% of them are "not dead".
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I think I was interviewed for this article. I guess I forgot how to talk in sound bites. At least I got promoted to exec!

I wish the "top" angels had some outside SV diversity; I know two thirds of that group pretty much directly.

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How on Earth is Chris Dixon #1??????
The cynic in me is thinking that it's because BusinessWeek is based out of NYC. Don't get me wrong though, cdixon's blog is pretty insightful, and it sounds like he's got a good rep.
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Interesting how pg is the only YC founder listed here. Other than being the most visible face of YC, why is only he on the list?
There's other interesting omissions in that list. Most glaring of all, where's Vinod Khosla?
Despite the number of oriental and south asian people in the valley, how came their are so few of them in vc, never mind blacks or latinos.
The Harvard math PhD...

I thought pg's PhD was in Computer Science?

Wikipedia says "Applied Sciences" (http://en.wikipedia.org/wiki/Paul_Graham), but paulgraham.com says Computer Science (http://www.paulgraham.com/bio.html).
Someone contact the Wikipedia people and tell them to update their reference.
Someone tell PG to update his page.
Wikipedians strongly recommend against that and get annoyed when people do it. Anyone that wants to fix their own mistaken Wikipedia page is best off doing it by posting a link on the talk page with the correct information and letting someone else fix it, or having someone else do it for them.
I read staunch's post as a joke -- "obviously Wikipedia is correct, so have pg fix paulgraham.com to what Wikipedia says".
Yes, CS.
What tends to be the biggest contributor to angel success? Knowledge, instinct, network, luck? Or impossible to tell?

I'm assuming it largely comes down to the type of people (smart, hardworking, get 'er done) in the startup and the angel's network.