1920's Goldman CEO Middle School Dropout vs. Jamie Dimon

Which type of person would you rather be: a) a first-gen, quirky, gritty type guy who makes it to the very top of finance, fails, then picks himself back up and becomes a massive success; or b) a charismatic chad who is sharp and makes it to the top of finance, is steadily successful, and maintains "premium" status from top roles at top firms but doesn't fail / do anything extraordinary.

Similar question to Sydney Weinberg (Goldman CEO middle school dropout) vs. Jamie Dimon (HBS)

Sid - after a stint in the Goldman mailroom he gets a job at Goldman as a trader - but fails to be literate enough so Goldman SENDS HIM BACK TO MIDDLE SCHOOL “to work on his penmanship” lmfao. Then Goldman lets him back in and HE BECOMES CEO.

Jaimie - BCG to HBS to JPM and is the best CEO on Wall St. right now. 

This is intentionally broad to encourage creativity / subjectivity / diversity of perspectives -- and neither person is better than the other -- but curious to hear your insights.

Most importantly, which areas of high finance do you think would "suit" each type of person (i.e., PE, PC, VC, GE, IB, HF, etc.).

Just for fun -- shoot!


My guy Syd is a beast and no one can really compare.

A guy like Syd today reminds me of a start-up finance type person who can resonate with founders who have failed and are trying to “make it.” Theoretically, I would say all options are open but practically can’t see a guy like this rising up in a place like IB/PE as there unfortunately isn’t as much sympathy for this story line.

On the other hand, I see a low risk Chad going to PE.

Neither person is better and take this with a grain of salt as this is purely hypothetical.


Who would I rather BE? Definitely #2.

Who do I think would be better suited to different finance roles? Definitely also #2 in most cases. Except maybe VC.

Sid Weinberg being a Wall Street legend notwithstanding, in most cases what you want from someone is alpha. And that means betting on the safe, boring, but overall still top-performing guy, 9 times outta 10. A lot of people, even people in finance roles themselves, seem to think the goal of a HF is to generate giant returns... but as the name indicates, a HF is supposed to work by focusing on the opposite side of the risk/return equation, by minimizing risks.

Yeah everyone wants to be a rock star... but everyone wanting to be a rock star is how we ended up where we are today with every other fucking idiot wanting to grow up to be an influencer. And how you get guys so busy DJing that they force their storied investment bank to start doing small time savings and loans, wiping out literally billions of dollars in value.



Getting knocked down and having the grit and intelligence to come back from “go back to middle school” to “I am the Goldman CEO” is incredible.

Shows that formal educational credentials don’t entirely reflect someone’s intelligence (but still helpful in many cases).

There are many hidden geniuses out there who simply didn’t have a solid educational upbringing. Syd is a perfect example of that.


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