Wise Guy is a memoir, of sorts, from Guy Kawasaki. To be honest, I didn’t know who he actually is and what he has accomplished; it had felt like he was famous for being famous, almost the silicon valley equivalent of Kim Kardashian. Turns out, the guy1 started his career as a marketing executive during Apple’s early Macintosh days, went back as an Apple fellow and evangelist, founded a couple of small companies, and wrote a bunch of books along the way. He figured out how to market himself and in some sense, Wise Guy is the latest entrant of that lengthy body of work.
As usual, I’m pretty skeptical of self-help books from self-proclaimed thought leaders and productivity gurus. Ever since I found out that the author of Rich Dad, Poor Dad made up his story— the central one that gave his bestselling book its title—and in fact made most of his money by upselling his readers to subsequent seminars, I’m particularly wary of self-serving advice. This entire genre of literature is overrun with self promotion and aggrandizement, sometimes at the literal expense of gullable readers who just want to improve themselves.
Fortunately, I don’t think Wise Guy falls into this anti-pattern; in part, it’s simply because he’s not trying to sell anything, other than maybe his life principles. Granted, many of those principles are hokey or end up being common sense, but true to his role as a marketer, Guy knows how to weave a personal tale to get his points across. The book is strangely endearing and genuine in that way, with just enough vulnerability to make his anecdotes and those lessons derived feel like earned wisdom2.
One principle that stuck with me is how he expressed goals in life, in the context of not sweating its ebbs and flows. I’m paraphrasing a little bit, but the gist is: life’s goods and the bads are never as extreme as they seem in the moment, and all things eventually revert to the mean; the goal, then, is to work towards shifting that average upwards. I like the framing here because life is filled with highs and lows, sometimes materializing in ways that we can’t control anyway. The long game, though, of driving towards generally better outcomes is a variable that we can manage in ourselves; even if, it’s as simple as understanding and mastering our own emotional reactions.
All in all, Wise Guy is a light and easy read, but a book that I hesitate to recommend because much of it can feel fluffy and fixated on the author’s own happenstances. I do think Guy has some useful advice here and a couple of interesting takes on his own life experiences, but those gems are interleaved between stories that often skirt the edges of distaste, a cascade of “look how famous and awesome I am!” anecdotes.