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Drew Houston reminds us that becoming a great CEO isn’t something you’re born knowing — it’s something you actively learn along the way.
“Your job as CEO changes every six months, every year, every couple of years. Just nobody tells you that… Nobody is born a CEO. You learn it. And the challenge is you just don’t know what your blind spots are. The chessboard is a lot bigger than just building a good product.
As CEO, everything from strategy to building and managing a team is your responsibility.
When asked how he scaled from coding the first version of Dropbox himself to managing an organization with thousands of employees, Drew responds:
“Reading was probably the single most valuable thing that I did.”
To decide what to read, he would also ask himself the question: One, two, and five years from now, when I look back on today, what will I wish I had been learning?
In terms of individual books, Drew recommends High Output Management by Andy Grove and The Effective Executive by Peter Drucker for managing and scaling an organization.
But he also argues that being a good CEO requires having good judgment about a lot of different things, and says Poor Charlie’s Almanac by Charlie Munger is probably the best book he’s read for that.
He also recommends looking at and talking to people who are a few steps ahead in their journey.
Becoming a great CEO is a continuous journey of learning and growth, where the key lies not in knowing everything, but in staying curious, adaptable, and willing to learn from those who’ve walked the path before you.
