Sobriety source #2: AI as the next platform shift. Every wave of new companies that transforms their respective industries is fueled by a major platform or technology shift. The advent of the web did this. The smartphone and mobile applications did this. And there is no doubt that AI is our next wave. But does every new wave always necessarily favo... See more

Weird is interesting . My friend Jared recently joined Union Square Ventures as a venture partner and wrote a short essay about the consumer applications we should be looking for in the age of AI - and how likely they are to appear “weird” at first glance. Indeed, new social paradigms that consume our psyche tend to appear strange when we first use... See more

Simply put, success breeds confidence. The longer this success lasts, the more a leader’s confidence grows.

The tricky part is that this increase in confidence is initially a positive because it is what enables a leader to take risks, expand, and grow. However, if success is sustained for long enough, an increase in confidence can morph from an adva... See more

The more you see, the more skeptical you become. Optimize for skepticism and curiosity. Having been a VC and invested as an angel in well over 100 companies, my inbox flows with ideas of all kinds from aspiring and repeat entrepreneurs. In the earlier days, I’d get excited by ideas especially the first time I saw them. But over time, I soon realize... See more

Speculative frenzies are part of technology, and so they are not something to be afraid of. Those who remain level-headed through this moment have the chance to build extremely important companies. But we need to make sure not to believe in the delusion that has now spread from Silicon Valley to the rest of the country, and indeed the world. That d... See more

Many people pretend they do. Often they don’t because their ego and fear of failing get in the way. There is a close inverse correlation between ego and self-confidence. The latter is also an excellent indicator of resilience. Last week, a new study on the characteristics of unicorn founders found unlimited self-belief to be one of the three domina... See more