Sublime

"By periodically investing in an index fund," Buffett says in his inimitable style, "the know-nothing investor can actually outperform most investment professionals."2

With early investments in social media companies such as Twitter, Tumblr, Foursquare and Zynga, Fred Wilson has become one of the world's most watched angel investors. And one of the opportunities he is watching most attentively is the emerging industry of digital money.

However, remember that we want your first ten investments to be $1,000 syndicate-level swings at bat so you can learn at the low-stakes table, where mistakes aren’t devastating. After that, in this book, we talk about making twenty $25,000 bets and quadrupling down on the winners with a $100,000 follow-on investment.

The successful investor Bernard Baruch was once asked at a party for some stock picks. Rather than share his favorite ticker, Baruch explained his simple methodology for finding winning investments—one I’ve embraced as well: Find companies whose product you buy, use, throw away, or however you’ve used it, you need to repurchase it within thirty day

Splitting the investment across multiple rounds is helpful in two ways: risk mitigation and opportunism.