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No matter where you look, the technology industry — from stalwarts to startups — is going through a reset. And that has led many companies to lay off people, cut costs and pare back their ambitions.

For so many of our startup founders, this is a new experience — a whole generation of entrepreneurs hasn’t experienced a bear market. And as a result, they don’t have frameworks to deal with this new reality. It is not as if they don’t want to deal with the situation. It is just that most founders are biased towards optimism (as they should) and have a hard time optimizing for the realities of tough times.

One of the toughest tasks for founders is figuring out how to tighten their belts. It is hard to decide how many people to cut from the company payrolls. People make incremental cuts to their teams — and these cuts don’t have a real impact and lead to more cuts.

Bill Gurley, a partner at Benchmark Capital, is a venture investor who has been through a few ups and downs. He recently tweeted:

The tweet, while succinct, didn’t really do justice to Bill’s thinking. I remember recording an interview with him in which he talked about downturns, layoffs, and surviving downturns. It is some of the best advice you can get in 15 minutes.

August 10, 2022. San Francisco.

Are Uber drivers entrepreneurs?

Benchmark Capital’s Bill Gurley has been at the eye of the storm called Uber, that included cutting the cord with its lightning rod CEO Travis Kalanick, in a public manner. He also has been the service’s biggest champion. In this Uber-long (no pun intended) piece, he makes a case for Uber as a positive force for the drivers. Gurley, like a great analyst that he once was, makes a case for the positive impact of Uber. This one paragraph sums up the entire thesis: Continue reading “Are Uber drivers entrepreneurs?”

Day traders, angels and venture capital: The internet changes everything, including money

London is the grandfather of economic excess and perhaps an appropriate role model for New York and San Francisco, the new Babylons of the post-millennial world. It is hard to escape the presence of money — fancy super cars, fancier homes and fancy financiers — where the stench of excess is masked by the sweet scent … Continue reading Day traders, angels and venture capital: The internet changes everything, including money