About  /  James Hamilton
team-james.png

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.

01

Posts by James

10 OF 29
Aug 26, 2026
30 Years in Conservation: Whit Fosburgh on What’s Actually Changed

We recently had the opportunity to sit down with Whit Fosburgh, Executive Director of

THE DRIFT
Aug 19, 2026
Are ChatGPT Ads Available in Mexico?

Yes, and the answer comes with a date. ChatGPT Ads went live in Mexico

THE DRIFT
Aug 19, 2026
Are ChatGPT Ads Available in the UK?

Yes. On August 11 2026 OpenAI said they were starting ChatGPT Ads in five

THE DRIFT
Aug 19, 2026
Are ChatGPT Ads Available in Canada?

Yes, and Canada has been in this channel long enough to have real data

THE DRIFT
Apr 7, 2026
AI Search Feels Like SEO in 2003. That’s the Opportunity.

AI search is already doing real work. People are using ChatGPT, Google Gemini, Claude,

THE DRIFT
Jan 23, 2026
Webflow vs WordPress for AI Search Visibility and SEO

Which CMS actually supports long-term search performance as discovery shifts from human browsing to

THE DRIFT
Dec 2, 2025
Search? Ads. Social? Ads. AI? Ads.

ChatGPT ads are coming. Is your brand ready?  For three years, ChatGPT has been

THE DRIFT
Nov 24, 2025
Launching oakpool.ai

Why we’re building for the AI Search era Today, we’re introducing oakpool.ai, a sister

THE DRIFT
Nov 21, 2025
AI Search Rewards Proof, Not Promises

In the classic SEO era, brands could manufacture credibility by signaling it. You could

THE DRIFT
Nov 12, 2025
Pandion x oakpool: Dragon Mom

We are thrilled to share the trailer for a new short documentary from Pandion

THE DRIFT
02
03
~~~~~~~~~~~~~~~~~~~~~~~~~~
~~~~~~~~~~~~~~~~~~~~~~~~~~

Build with us

Tell us what you’re working on, and we’ll tell you honestly whether we can help.