Nov 4, 2016 ยท 1 minute

A few weeks ago, I decried CB Insight’s latest “bracket” as everything that was wrong with Silicon Valley.

From that post:

CB Insights is doing a bracket of “most admired founders,” a follow up to brackets like what VC you’d most prefer to have as your Series A investor or what the most undervalued unicorn is. It’s telling that they are asking the “most admired” founders, not the best founders or most effective founders.

Also telling are these four match-ups in round two, highlighted by CB Insights newsletter yesterday:

  • Travis Kalanick vs. Jack Ma
  • Reed Hastings vs. Larry Ellison
  • Jeff Weiner vs. Peter Thiel
  • Steve Jobs vs. Salman Khan

The “asshole” versus “nice guy” positioning can’t be accidental. A man who threatens his critics with dirty oppo researchers versus a former school teacher turned billionaire. A man who pioneered employee-friendly policies like unlimited vacation and year long parental leave versus a man whose catchphrase was famously “it’s not enough that I win, everyone else must fail.” A man who openly wrote and talked about “compassionate management” versus a man supporting Donald Trump. A man who denied his child and stiffed her mother on child support versus the guy reinventing education.

Come. On.

My prediction? Kalanick wins easily. Hastings will beat Ellison but only because Ellison’s bad boy behavior isn’t in the news anymore. Thiel-- despite being painted as the bogeyman out to destroy all media-- wins. And Jobs is a no-brainer.

Guess what? I underestimated you, CB Insights audience. Jack Ma beat Travis Kalanick who fared worse than almost any other decacorn founder in the rankings. Reed Hastings beat Ellison. Although, yeah, Thiel and Jobs won. But Thiel was weeded out in the next round.

As of now, the bracket has advanced to a final four and while they may not all be “nice guys” you can’t fault the ranking: Elon Musk v. Bill Gates; Jeff Bezos v. Steve Jobs. (Zuckerberg was edged out by Musk. Hard head-to-head.)

Aside from Musk, it’s interesting that legends from the 1990s fared better than the unicorn crop of today. Who says entrepreneurs don’t have a sense of Valley history?