Casalena, Stoppelman, and the Collisons would be on pace for returns of 73 times their money-or $1.8 million for each $25,000 they may have invested, before dilution. At just a $25,000 check, each would be sitting on shares worth about $40 million, not accounting for dilution. Sacks, who later led Zenefits and is now a full-time venture capitalist, invested in an additional round that valued the company at $1.1 billion later that year.Īt a market capitalization of $16 billion, Weiner, Stone, Morin and others were set to enjoy returns of 1,600 times their initial capital. By then Slack was worth $220 million post-investment. Casalena, Stoppelman and the Collison brothers joined in Slack’s Series C led by Social Capital. In their first round of funding, led by Accel and including Andreessen Horowitz a decade ago, Weiner, Stone and ex-Facebook executive and Path founder Dave Morin invested at a valuation of just about $10 million. Slack’s angel investing story dates back to before Butterfield and Henderson abandoned their game-making plans to build an enterprise software tool. The virtuous cycle, or vicious cycle, depending on how you look at it, goes again and again.” And by their mentorship, they give these companies a leg up. “You have people who are winners from the previous generation picking winners from the next.

“It’s Silicon Valley’s greatest strength and Achilles heel,” says Margaret O’Mara, a professor at the University of Washington who has studied the modern history of Silicon Valley.

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