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!"
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.
If you haven't heard it before then I'd definitely recommend listening to Sacca's critique of Blumberg pitch on TAL:<p><a href="http://www.thisamericanlife.org/radio-archives/episode/533/its-not-the-product-its-the-person?act=1#play" rel="nofollow">http://www.thisamericanlife.org/radio-archives/episode/533/i...</a><p>I've heard a lot of people pitch but I'm not sure I've heard anyone pitch better than Sacca can do <i>while ad-libbing</i>.
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.<p>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.
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?