Dorsey made the classic founder mistake: diversification without dominance. He split focus between Twitter and Square (Block), then gave up Twitter's CEO role twice—first to Evan Williams, then to Parag Agrawal. Meanwhile, Musk maintained obsessive control of Tesla through multiple near-death experiences, refusing to dilute his vision or his stake. When Twitter faced the 2022 crisis, Dorsey's earlier departures meant he had minimal equity leverage; Musk's 13% Tesla position kept compounding while Jack was watching from the sidelines.

The numbers tell the real story: Tesla's market cap hit $1.2T because Musk bet his reputation and fortune on an unpopular thesis when the stock was $20. Dorsey bet on fintech adoption and social media innovation—solid bets, but Square's valuation peaked at $130B before collapsing 75% by 2022. Twitter, despite its cultural dominance, never justified a $44B acquisition price; Musk bought it as a side project while running Tesla and SpaceX. Dorsey's mistake wasn't the companies—it was fragmenting his wealth across too many bets when he could've gone all-in on one.

The final nail: Musk's wealth is almost entirely unrealized Tesla stock—it grows passively while he builds rockets and cars. Dorsey's Bitcoin advocacy and TBD startup consumed energy without creating comparable returns. In wealth-building, attention is capital, and Musk treats his net worth like a score that matters; Dorsey treats it like a byproduct. One compounded. The other cashed out early and pivoted too many times.