Paul Buchheit’s lucky streak as an angel (and a founder) | Hacker News Reader

Paul Buchheit’s lucky streak as an angel (and a founder)

deals.venturebeat.com

46 pointsprakash26 comments

Lucky streak? Sounds like he had a hand in shaping all those companies and he knows the people at Google doing the acquisitions. He created Gmail. He's a technical expert putting his money to work in businesses he understands and can help grow.

As a former professional poker player and sports bettor (who now works on the 'other side'), I looked at the headline in a different way.

There is an appropriate level of failure in all endeavors which involve risk. If you are winning 100% of your hands which make it to showdown, you are either on a real lucky streak.. or you're not going to showdown often enough. That is to say, you're leaving money on the table in terms of potential profit from hands which are not guaranteed winners.

So, I read the headline as a more polite way of saying that he is cherry-picking only the very best opportunities available to him. I'm not in a position to say one way or another whether that is appropriate to his investment goals.

Or the game is rigged, e.g. the billionaire's kid who "magically" manages to succeed in whatever business he tries.

Not saying that this is the case at all, simply pointing out the other logical possibility given your metaphor.

Hey, I'm in same position, but haven't yet switched to the Dark Side. Can you contact me at bettingbrandon at hotmail dot com I'd love to ask you a few questions about your experiences. Can't seem to figure out a way to message you directly on HN, thanks.

you are either on a real lucky streak.. or you're not going to showdown often enough...

People used to say similar things in Warren Buffett's early days - that he was either super lucky or wasn't leveraging himself enough to multiply his investment prowness. Now he's one of the richest men in the world.

And like Buffet, Paul isn't throwing darts at a roulette wheel, hoping for a winner. He is deeply involved in helping build these companies. He's a technical genius that hedges his bets. He can give access to his friends like PG or the Google founders. If making a poker analogy, paul would be the player with x-ray vision, knowing where and when to bet or fold.

That's a good point. Almost everyone will play the leverage game once it gets popular: this means that opportunities for the kind of statistical arbitrage people like mellow out, and what's more the whole stock market will be so highly inter-networked that the short term stock price will be fragile. But through judicious investment and directorship one's illiquid investments -- as Berkshire Hathaway tends to make them, can be multiplied far more profoundly than traditional leveraged investment. In this way B.H. operates more like private equity or a venture firm -- what's amazing is the difference in scale.

Incidentally, I worked out the same numbers for my own financial situation. It doesn't make a lick of sense for me to save up and diversify at this point, or even actively invest to chase the best return I can, not now. All of my money and effort should go back into my startup, so that I achieve profitability there, and liquidity.

Does this mean Sanjeev Singh is Charlie Munger?

Probably I don't understand gambling world well enough: What is 'other side' to being professional poker player and sports bettor?

I work for an online gaming company ("The House," as it were.)

'When I was living in Italy, I was once trying to tell someone that I hadn't had much success in doing something, but I couldn't think of the Italian word for success. I spent some time trying to describe the word I meant. Finally she said "Ah! Fortuna!"'

-- pg

He's playing the game at a whole other level. With his intelligence and connections in SV, I don't think calling it luck does it justice.

I'm still waiting for him to start a hedge fund so that non-connected SV-outsiders can get in on his action.

It's an interesting model: work on something for a while to show people what you can do, convince friends in high places they want you (back), get "acquired" and EOL what you spent six months to two years working on.

  Appjet = left google -> appjet -> google acquisition.
  reMail = left google -> xobni -> remail -> google acquisition.
  FriendFeed = left google -> friendfeed -> acquisition by friends at facebook.

(It's not just a "web" thing -- check out some Cisco acquisition cycles from people who leave, create new products, then get acquired back again. I think most Cisco Family acquisitions involve actually keeping the products they acquire though.)

Isn't that a bit of oversimplification?

Google buys a lot more companies started by people who weren't Xooglers.

Also, those steps between

leave google -> ... -> get acquired

are really, 'make something people want' and as we know, that's not some simple formula. Conspiracy theory, or not. :-)

Ah yes, only Mr Bucheit (and other connected people) know what "people want", the rest of us are just jackasses [sarc]

Sure, but it's predicated on doing good work. If Paul didn't kick ass @ google, no one would have followed his work after he left. If he hadn't built something awesome after he left, they wouldn't have asked for him to come back.

Skill is the common denominator to all of his good fortune.

However, there might be some truth to the idea that Google alumni seem to be more successful at subsequent startups than alumni of, say, Microsoft, Amazon, or Sun.

I can't actually think of any off the top of my head, but 10 years ago it seemed like there were microsoft employees with startups everywhere. I'm sure plenty of them were successful.

Paypal has the most successful alumni network in the valley.

Right -- at least on a per-capita basis, anyway.

Zuckerberg made an interesting comment at this year's startup school, when he said that he explicitly wanted Facebook to be a "a great place to be from" -- i.e. FB wants to be a good company where you can learn for a few years, and then go off and start your own venture to apply what you've learned. I thought it was refreshing to hear a CEO recognize and embrace that working for his company might only be one step in someone's career.

FriendFeed = left google -> friendfeed -> acquisition by friends at facebook.

pb didn't have personal relationships with the people at facebook pre-acquisition. sure they knew of his achievements prior to friendfeed but by that definition most people in the valley would be his friend.

Cisco's acquisition strategy is driven by a desire to put new product into their sales channel, most are driven by a business unit that plans to continue to sell the product.

Google seems to be using acquisitions to add talented engineers, most of the products seemed to be killed or undergo radical revision.

Completely aside, this article lists only his successes, so it presents a biased view.

Edit: changed prevents to presents.

prevents -> presents?

(Normally I try not to nitpick, but in this case it might completely flip the meaning of what you're saying.)

Fixed. Thank you!

As I understand it, being "lucky" as an angel involves (in the first place) quality deal flow. With Paul's background I would bet he's got incredible deal flow.

(There are a lot of other things too, I'm sure, but this is a big one.)

Its like they say, the harder you work, the luckier you get.

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