Author, Investor, Speaker, Mentor
I am probably one of the happiest people in the world, but even I feel melancholy every once in a while. While I’m lucky enough that these feelings are both rare and invariably transitory, I’m struck by the fact that I feel like I shouldn’t write about them. It’s not because I’m afraid that revealing … Continue reading The Melancholy of the Happy
One of the perils of living a portfolio life is the need to decide how to allocate your time and energy among potential initiatives. The challenge is that most initiatives are full of uncertainty. In an effort to structure my thinking about my own life, I decided to create a classic chart, with one axis representing … Continue reading The Effort-Outcome Model For Evaluating Your Portfolio Life
We stand with Paris. Like everyone else, I was appalled and saddened by the recent attacks in Paris.* One of the strange things about modern life is that the news media intimately acquaints us with vivid images of atrocities and suffering even as their geographical distance makes it nearly impossible for us to do anything … Continue reading Paris, ISIL, Evil, Law Enforcement, and War
I am an unapologetic booster of capitalism in general, and Silicon Valley in particular. It’s even in the name of this blog! Yet I’ve found myself playing the role of skeptic in an increasing number of conversations lately. As our current bubble (yes, I said it!) reaches new heights, it seems like all anyone in … Continue reading What KRS-One Teaches Us About Silicon Valley
When Jesse Noller’s essay explaining why he had essentially left his software community made it to the top of Hacker News, I read it with great interest. Noller was one of the pillars of the community, but by pouring all his time and energy into the community, he neglected his marriage and family, and ultimately … Continue reading You’re not indispensable (except when you are)
The great Eric Barker just wrote generally about fighting the effects of the Imposter Syndrome, in which successful people are convinced that they are frauds, and do not deserve the success that they’ve achieved. Imposter syndrome is extremely widespread, affecting 70% of successful people, according to a study by psychologist Gail Matthews. If it affects … Continue reading Fighting the Imposter Syndrome
One of the mental traps that I try to avoid is what I’m going to term “the implied assumption of success.” This trap occurs when entrepreneurs say something like, “If I raise $2 million instead of $500K, I’ll be able to get much farther, so I should raise $2 million.” The issue, of course, is … Continue reading The Implied Assumption of Success
Paul Smith recently wrote about the phenomenon of entrepreneurs who slack off after raising their seed round: “Here’s what I see three quarters of startups doing immediately after they raise a seed round: After months of working 60 hour weeks (and the rest, usually) to launch and demonstrate early growth to convince investors they’re worth … Continue reading Entrepreneurs who slack off after raising money aren’t entrepreneurs
This morning, I read a long profile of an extreme altruist, who believes in a) giving away as much as possible and b) focusing on whatever will provide the greatest benefit, regardless of whether that means helping loved ones or strangers. In one passage, she worries that she’ll have to give up her dream of … Continue reading Extreme Altruism and You
“You? And Ben? Going to Burning Man?” When my friend, co-author, and business partner Ben Casnocha and I announced that we were going to Burning Man, the reactions we received, both in person and on social media, ranged from disbelief to shocked disbelief. My typical in-person response was, “Why are you so surprised? Is it … Continue reading A Capitalist Visits Burning Man