So why quit? Three reasons. First, I’ve felt for a few years now that the startups I’m seeing don’t seem so much like progress as just shopkeeping. This isn’t a dig: there’s money to be made razoring a thin slice off a huge market, and there’s certainly less risk in that than there is building a market from scratch. But it’s just not that interesti... See more

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

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

Last week, Brad Gerstner and Bill Gurley discussed how Tech has grown from 5% to 15% of global GDP over the last 15 years, largely owing to faster growth rates.

As software companies get fitter and stack new S-curves of growth, later stage companies become highly effective capital allocators - which is why we’ve seen Tech outstrip the rest of the ec... See more

When I have a piece of writing in mind, what I have, in fact, is a mental bucket: an attractor for and generator of thought. It’s like a thematic gravity well, a magnet for what would otherwise be a mess of iron filings. I’ll read books differently and listen differently in conversations. In particular I’ll remember everything better; everything wi... See more

We modern Israelites have also been worshipping false gods.

Our American idols are prestige, power, social acceptance, popularity, elite opinion, and the Ivy League—but I repeat myself. Our idols are the coveted board seat. The best tables. Relationships with the pretty people.

We put truth on the altar, as if it were a tithable commodity, to remain ... See more

“The best way to think is to write.”

The world doesn’t reward the people with the best ideas. It rewards the people who are best at communicating ideas. Want to publish a bestseller or launch a startup? Want to spread your ideas across the Internet like schmear on a New York bagel? Then become a better writer .

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