The Job Keeps Changing
Houston: Your job as CEO changes every 6 months, every year, every couple years. Nobody tells you that. And in fact, some of the things that made you good at the prior stage become a hindrance for the next stage.
For example, I wrote most of the first version of Dropbox. But there just became too much stuff to do and I had to stop coding.
Nobody Is Born a CEO
Houston: 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.
You have to be able to make smart and fast decisions about markets, business models, competition, strategy, how to build a team, how to run a team. That's pretty tough when you've never done any of it.
Nobody is born a CEO. You learn it. The challenge is you don't know what your blind spots are.
The Question He Still Asks Himself
Houston: Probably one of the most useful questions I ask myself — and still do — is: one year from now, two years from now, five years from now, when I look back on today, what will I wish I had been learning?
One year from now, what will I wish I had been learning?
The Reading List
Houston: Reading was probably the single most valuable thing I did. My favorite book on management is High Output Management by Andy Grove — the bible of how to scale an organization. The Effective Executive by Peter Drucker is really good.
Poor Charlie's Almanac by Charlie Munger is probably the best book on how to build mental models to break down the complexity of the world and know when to use each.
But also having friends that are one step ahead, two steps ahead, five years ahead — and just looking at the deltas between them.
Reading was probably the single most valuable thing I did.