That horizon is massive and inevitable. We can take lessons from the evolution of social media to will a new multiplayer future of shopping into existence and change for the floundering paradigm forever.

Market Selection in Vertical Integration

If you were to ask what sunk Convoy, it ultimately boils down to an over-dependence on the digital freight matching software they pioneered with a corresponding inattention to the operational parts of the brokerage that were really low margin. Technology isn’t a panacea for operational excellence. Every vert... See more

laughter

I’ve been doing improv comedy for the last twelve years. Over that time I’ve realized there are at least two types of laughter you hear from the audience. One is a response to something clever or smart, like ‘ha ha I see what you did there, very nice.’ It’s a shallow sort of laugh and one that comes mainly from the mind. 

The other - my favo... See more

"So much advantage in life comes from being willing to look like a failure in the short term."

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

Scrolling through Twitter led to more scrolling and then a feeling of emptiness and guilt for wasting time when I finally managed to leave the app — scrolling through Sublime more often than not led me to putting away my phone, getting a breath of fresh air, and getting to work on that passion project I’d put aside years ago.

He thought about space the way he thought about mathematics or analytic philosophy or the Torah or Mozart’s twentieth piano concerto, which he sometimes played at night when my sister and I were going to bed. It was beautiful and complex and infinite, and how could you not want to explore that, know where it came from, know where we came from?

This has a significant impact on the competitive advantages of a firm in the market as it scales. When party rounds were the standard course for smaller seed firms, connections were the scarce skill set, enabling access to deals led by other reputable firms. As these funds have become larger and rounds have become increasingly tighter, conviction b... 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