How do you make your first million, and your next? Henry Yoshida breaks down the real story behind his wealth milestones, from earning a retention bonus during the Financial crisis of 2007–2008 amid the Merrill Lynch acquisition by Bank of America, to generating seven figures through startup exits. He shares why ownership — not employment, is the real driver of long-term wealth, and how positioning yourself as an equity holder creates asymmetric upside.

6 Bullet Point Highlights:

His first million came from a retention package during the Merrill Lynch acquisition by Bank of America.

Timing and sticking through uncertainty during the financial crisis created unexpected upside.

His most recent million came from selling a previous startup.

Startup exits don’t always have to be massive to create meaningful wealth.

Future millions will likely come from private investments and equity ownership.

Core lesson: Ownership creates seven-figure windfalls, employment rarely does.

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