About  /  James Hamilton
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James Hamilton

CO-FOUNDER, PARTNER

James is an entrepreneur and technologist focused on building businesses and brands that thrive and endure. He co-founded oakpool, a founder and employee-owned digital marketing firm that builds teams, systems, and software to help brands achieve sustainable growth.

More about James.

oakpool works globally, with team members and clients across the United States, Canada, Latin America, and Europe. Past and present clients include GORE-TEX, Goslings Rum, Caesars Entertainment, and Zum.

At oakpool, James leads new product and service development, including oakpool.ai, which focuses on Generative Engine Optimization, helping brands become legible, referenced, and surfaced inside modern AI search engines like ChatGPT, Gemini, Perplexity, and Claude.

Along with his work at oakpool, James has spent nearly a decade in early-stage venture capital and company formation, working as an investor and Entrepreneur-in-Residence at firms in Boston, London, and the Bay Area. He earned his MBA at Imperial College London and his BA at the College of Charleston.

James comes from a family of artists, curators, gallerists, and writers, and approaches entrepreneurship as a creative act. Beyond his work, James is passionate about travel, skiing, fly fishing, the arts, and our planet.

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Posts by James

10 OF 29
Nov 11, 2025
SEO, AEO, GEO, AISEO… WTF?

A Rose by Any Other Name Would Smell as Sweet But Will It Rank

THE DRIFT
Sep 4, 2025
Our Advisory Board

Pouring high octane gas on the fire As we reflect on the first half

THE DRIFT
Aug 16, 2025
On Novelty

Its many forms and purposes I recently spent some time reflecting on the concept

THE DRIFT
Aug 15, 2025
Ego

Musings on the concept The English language has done a great disservice to the

THE DRIFT
Jun 17, 2025
How to Evolve SEO Strategy into GEO Strategy

Generative Engine Optimization is Here to Stay Co-Authored by James Hamilton, and Dan Zazworsky.

THE DRIFT
Jun 14, 2025
The global local approach

The global local approach Airbnb is a marketplace platform that connects travelers with local

THE DRIFT
Jun 13, 2025
Welcome to The Drift

The cobbler’s children have no shoes What’s that old saying? “The cobbler’s children have

THE DRIFT
Jun 7, 2025
Nomadic Vignettes: Iceland

The earth from above There is at least one redeeming quality about Play Airlines,

THE DRIFT
May 24, 2025
The Austrian Defense

90% Symmetrical In Chess, the act of copying an opponent’s moves at the beginning

THE DRIFT
May 23, 2025
Why We Joined 1% For The Planet

An easy decision Alex and I both own tattered, dog-eared, overly annotated copies of

THE DRIFT
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