The Power of Vulnerability (Sponsored by ClassPass)

Bragging via Thinkpiece is not novel (it’s what Medium is for, after all), but sometimes a work of art breaks through the monotony of full-fledged gasbaggery. Today, Rajil Kapoor — who wants you to know he has merged with ClassPass—takes things to a truly cinematic level in his Power of Vulnerability post:

Rajil — who believes it’s important that you know he was a successful VC before deciding to become an operator again and then successfully merging with ClassPass—not only checks all of the “submarine brag” boxes, he does so in a perfect three-act structure:

  • The Power of Vulnerability sets up the action by exposing us to Rajil — still merged with ClassPass, successfully I might add — and his penchant for vulnerability;
  • It rockets into a dramatic Act 2 that’s entirely about his career triumphs;
  • And transcends everything in a finale that’s… also about his career triumphs (and ClassPass).

Well, it’s hard to explain, unless you truly “get” how to properly structure a story from first principles. Rajil — whose ClassPass/FitMob merger is likely to be an HBS (where Rajil earned his MBA) case study — understands what I mean.

For the rest of you: I’ve color-coded the post to help navigate the story. See below.

Special thanks to various Silicon Valley luminaries for reading drafts of this post. What I mean to imply by that is: this post is significant enough to warrant multiple drafts and multiple reviews by multiple editors.


Unvarnished, utterly self-unaware braggadocio and/or false humility in the form of “what’s your greatest weakness?”

Jaw-dropping, agonizingly ironic self-mockery.

Advertisements for ClassPass.

Vapid quotes from or references to the two sources Rajil skimmed on the topic of “vulnerability.”

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