Oliver Grant on Buying the Conventional, Well-Run Group

Oliver Grant in studio.

A buy-side veteran argues the contrarian case: skip the AI-mature operator, buy the conventional well-run group at a discount, and deploy the AI yourself.

Show notes

Oliver Grant is a buy-side investor with eleven hospitality acquisitions in the last six years. He joins Samuel to argue a contrarian thesis: the AI-mature operator is overpriced today, and the better trade is to buy a conventional well-run group at a discount, then re-platform it onto AI yourself.

The conversation moves into specifics — three deals he’s watching, why earn-out structure matters when lease math is uncertain, and the operating-partner question that decides whether the thesis holds.

Timestamps

  • 02:00 — The thesis: three components of the AI premium
  • 09:30 — Why two of the three premium components depreciate quickly
  • 15:00 — The operating-partner constraint
  • 19:00 — Three groups Oliver is watching right now

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