Confessions of an Entrepreneur

Sometimes the prize feels closer, other times farther away. Still other times it feels like we are drowning in aimlessness and exasperation. An identity crisis looms for any high achiever flirting with failure, and a calculation begins on the conflicting forces of sunk costs and lost time on the one hand, and reputational harm on the other. As entr... See more

Take, for example, the ambition to “make your venture-backed startup profitable”: to develop, market, and distribute a product or service that’s never existed before, in a form that’s valuable and accessible enough for large numbers of people to want to pay you for it, in sufficient quantity that your revenue consistently exceeds your costs.

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Today, we are in a crisis. Silicon Valley's best — our top operators, exited founders, and most powerful investors — are almost all on  bad quests.  Exiting your first startup only to enter venture capital and fight your peers for allocation in a hot deal is a bad quest. Armchair philosophizing on Twitter is a bad quest. Ya

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For a long time, I harbored the belief that there was a yearning at the heart of entrepreneurial ambition, a tender dimension that no one wanted to acknowledge. Some spiritual aspect beneath the in-office yoga classes and meditation apps and selective Stoicism and circular thought-leading. How else to explain the rituals and congregations, the conf

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