Welcome to The Drift

img welcome to the drift oakpool
THE SHORT ANSWER

The cobbler’s children have no shoes

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

Well, in this case we’re both the cobbler and his children. We’ve been crafting nice shoes for our clients for years while ignoring our own feet. Those days are over. That’s right, we’re actually marketing ourselves now. Here we go.

I just finished writing a proposal for a piece of new business that I should be excited about. It was like pulling teeth. Not because I’m not excited to grow our marketing business, or to help a new partner scale their own. I am, in fact I need to be. But it was still worse than a trip to the dentist. 

So, I asked myself “Why? Why aren’t you more excited about new clients you entitled piece of sh*t?”

Turns out the answer’s pretty simple: I’ve done it before. Hundreds, maybe thousands of times at this point. My life has been one big hunt for new ideas, activities, experiences, places, and people. The creation of new things will always be more rewarding than walking down a well-trodden path. Just going to have to take that as a fact at this point. 

So what’s a company to do? Well, life’s all about balance. So, we’re balancing out those repetitive tasks with a communal creative outlet we call The Drift. Here you’ll find errant musings on business, travel, the nomadic lifestyle, and sporting endeavors alongside interviews, technical analysis, and other *hopefully* helpful content. 

One could argue that if it weren’t for writing – we wouldn’t be here today.

My co-founder Alex Ford and I were colleagues first, then friends, and then business partners – in that order. We wouldn’t have ended up as colleagues, running competing startups (GuideHire & Amberjack) if we didn’t share an interest in following our passions. We wouldn’t have become friends if we didn’t share both a geographical location and an interest in fishing. We wouldn’t have become business partners if we didn’t respect each other’s writing (and growth marketing) abilities. So, here we are resurrecting an old pastime for the team, all while building domain authority and an arsenal of SEO-rich content so that I can keep writing proposals until my teeth fall out. 

Welcome to The Drift. Happy browsing. 

– James

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