It's been 20 years, and despite endless attempts to bend the internet to its will, advertising remains a fraught part of the digital media experience. The internet put the consumer in control, connected the impression to the transaction, and in the process, completely transformed how we think about advertising, personal data sovereignty, and its underlying economics.

AI is about to change things all over again.

Troy, Alex, and Brian delve into digital advertising's messy history, failed attempts at innovation, and the impact of new interfaces that flatten the space between desire and fulfillment.

This week, we invite our Gen Z friend and Troy's son, Seb, to provide a generational perspective.

Plus, Succession is a good product. Enjoy!

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People vs Algorithms

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The death of ad formats