
How Super Angel Chris Sacca Burned Bridges and Crafted the Best Seed Portfolio - wj
http://www.forbes.com/sites/alexkonrad/2015/03/25/how-venture-cowboy-chris-sacca-made-billions/
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ryandrake
I can't help but see Survivorship Bias in any profile of a successful
investor. You rarely see the profiles of the more numerous people whose
investments lost them all their money. It's always "How XYZ became that 1 out
of ~1 million who flipped heads 20 times in a row. The secret to coin flipping
revealed!"

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imjk
I don't mean to come off too critical, but I'm curious how we the HN community
can move away from this sort of survivorship bias cynicism without discounting
it entirely. I openly acknowledge that survivorship bias is a very real
phenomenon that can be easily overlooked, but every time a story about a
successful entrepreneur or angel/vc pops up, there's the tendency to discount
every thing that is being said as survivorship bias, as if there's nothing
else to be learned from the story. These comments tend to overwhelm the
discussion in their prevalence. I think it puts a overall cynical attitude in
the community that I've seen overtake other entire online communities of
entrepreneurs. I really hope it doesn't do the same here.

~~~
existencebox
I'm honestly not sure the cynicism is a bad thing.

I'd say the HN community has a higher than average grasp of statistics (the
same could probably be said about many other entrepreneur communities) As
such, when we see something which all broad statistics tell us is "one in a
million" occams razor directs you to assume that it is in fact one in a
million.

That "let's be extremely doubtful given a high bayesian prior suggesting that
the doubt is legitimate" occurs strikes me as a wonderfully pragmatic
viewpoint. If someone really wants to convince me there's some "trick" to
being that one in a million they have to go against all of the evidence I've
been presented thus far to say that simply doesn't happen. (evidence coupled
with the fact that these sorts of news sources have a history and incentive
aligned with the "how to strike it rich" style articles.)

~~~
solve
> I'd say the HN community has a higher than average grasp of statistics

No, just no. From my experience as an engineer that's transitioned into
finance, I assure you that engineers and developers have the WORST pre-
conceptions about statistics as applied to investing. All of those have to be
unlearned fast at the start of a finance career. Took me years to fully
adjust.

~~~
myth_buster
Would you please share the examples as this would be useful to the engineers
in HN.

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foobarqux
I don't know how a profile of Chris Sacca could omit how he was a math prodigy
who hated math, never went to class for law school or lost $8 million dollars
trading in the stock market and refused to declare bankruptcy, instead paying
back creditors over many years.

~~~
icpmacdo
Here is a video of him talking about it with Kevin Rose
[https://www.youtube.com/watch?v=0cWl9UTHZoE](https://www.youtube.com/watch?v=0cWl9UTHZoE)

~~~
quickpost
Great interview with Sacca - highly recommended. Thanks for posting.

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ig1
If you haven't heard it before then I'd definitely recommend listening to
Sacca's critique of Blumberg pitch on TAL:

[http://www.thisamericanlife.org/radio-
archives/episode/533/i...](http://www.thisamericanlife.org/radio-
archives/episode/533/its-not-the-product-its-the-person?act=1#play)

I've heard a lot of people pitch but I'm not sure I've heard anyone pitch
better than Sacca can do _while ad-libbing_.

~~~
zemvpferreira
I agree that he did a great job, but consider the power of circumstances: it's
a lot easier to pitch when pitching is an intellectual exercise for you,
instead of the full expression of what you are and hope to be in this world as
a person, delivered to the gatekeeper of the capital you need to make that
journey, who will not give you a second chance if you fuck up, and without
whom you're destined to go back to living in your mother's basement, a broken
and destitute man shunned by society. Or back to Yahoo or Stanford or wherever
you came from.

~~~
myth_buster
Perhaps it's psychological. I've often found that if I build up stakes for a
test/interview/application, I perform far worse than attempting it with a more
frivolous attitude.

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staunch
Altruistic first-money angel investors, like Mark Markkula at Apple or YC with
Airbnb, deserve a ton of credit for the success of their startups. People who
glom on to hot startups launched by already-successful Silicon Valley insiders
deserve less. Twitter and Uber did not need help to exist the way Apple or
Airbnb did.

Angel investors should be judged by what they help bring into the world, the
value they create, not how rich they get from doing backdoor deals with JP
Morgan. That's how you judge lawyers.

~~~
kzhahou
The article talks about the work that Sacca did by tenaciously evangelizing
Twitter in the early days. I don't think the article mentioned it, but he did
the same for Instagram. He was all over it, posting non-stop!

You shouldn't assume he made no contributions simply because he was also
clever enough to make himself mega-rich.

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fapjacks
As if "clever enough" is all it takes.

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jalonso510
Would be really interested to see how big an effect the massive doubling down
on Twitter and Uber had vs. if he had just been an a more normal super early
investor. Did he generate the over the top amazing returns mainly by being
first into great companies, or mainly by being crazy enough to make outsize
allocations for the winners?

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padobson
tl;dr loudmouth with a penchant for social media and oddball cowboy shirts
made a lot of money investing in startups

~~~
brianstorms
As Spock once said, "Colloquially expressed, but essentially correct."

