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Sam Kroonenburg sold his last company, A Cloud Guru, to Pluralsight for just over $2 billion. Now he's back with Cuttable, an AI ad-creative platform, and Nathan's been using it for months on a client account. This is the behind-the-scenes on how it works, and the counterintuitive truth about winning on Meta: it's a volume game. You can't pick the winning ad up front, and neither can Meta, so the only lever you control is how many shots on goal you take. In this episode: Winning Meta is a vol...
Broadcast on
06 Sep 2026

Sam Kroonenburg sold his last company, A Cloud Guru, to Pluralsight for just over $2 billion. Now he's back with Cuttable, an AI ad-creative platform, and Nathan's been using it for months on a client account.

This is the behind-the-scenes on how it works, and the counterintuitive truth about winning on Meta: it's a volume game. You can't pick the winning ad up front, and neither can Meta, so the only lever you control is how many shots on goal you take.

In this episode:

  • Winning Meta is a volume game, take more shots, because you can't pick the winner and neither can the algorithm
  • Give people control over AI output, because what's valuable isn't a generated ad, it's an ad they're willing to publish
  • Only build what couldn't have existed two years ago

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Sam Kroonenburg sold his last company, A Cloud Guru, to Pluralsight for just over $2 billion. Now he's back with Cuttable, an AI ad-creative platform, and Nathan's been using it for months on a client account. This is the behind-the-scenes on how it works, and the counterintuitive truth about winning on Meta: it's a volume game. You can't pick the winning ad up front, and neither can Meta, so the only lever you control is how many shots on goal you take. In this episode: Winning Meta is a vol...