“Play.” — Craig Fenton on AI, Risk, and Re-engineering Business
From Google & Sports to Founding FI
From courtrooms to code: Craig Fenton started his career as a lawyer. Today he’s the founder of Fenton Innovation (FI), an AI company building automation suites for marine, private capital, and travel & tourism. We talked about why every company will be re-engineered for AI, how to start (today), and what it really takes to sell, hire, and build in a market that changes every 90 days.
“We never start with the tech. We start with the business.”
FI builds modular AI automations across three verticals:
Marine: from superyachts to supertankers
Private Capital: PE/VC investment pipelines, from origination to IC memos and LP updates
Travel & Tourism: ops and finance automation (think: invoice reconciliation at 1,000/min)
“AI should expand the human 20% (judgment, relationships, decisions) to 80%—and let machines prep the rest.”
How FI engages: diagnose growth vision → customer journey → choke points → then map AI to the value levers.
The Private Equity Flywheel
“Eat your own dog food. Do AI to the PE firm first—then into portfolio companies.”
Automate the deal pipeline: sourcing, research, due diligence, IC materials
Shift teams to judgment & relationships
After a few cycles, AI becomes a known lever (and part of the thesis)
From Google & Sports to Founding FI
Craig led strategy/ops for Google UKI (and Western Europe) and helped launch Bard (pre-Gemini). He also ran media/entertainment for the New Zealand All Blacks post–Silver Lake investment.
“I took time off to learn, built agents with my own hands, completed 14 nano-quals—and realized this is the moment.”
Why This AI Wave Is Different
Moore’s Law was annual; LLM capability is doubling ~every 90 days
New tectonic shift (after Internet, smartphone, blockchain): Generative AI
Most teams overestimate the short term and underestimate the long term
“Don’t apply AI like radio on TV. Re-imagine the medium.”
Examples:
Not “websites + chat”—rethink flows so the site navigates the human
Future teams = agentic swarms + humans; managers lead both
A Concrete Win: 4 FTEs → 1,000 Invoices/Minute
Tourism client in NZ: 5,000 invoices/month. Chartered accountants spent days reconciling to itineraries.
FI built an automation doing ~1,000 invoices/min, eliminating error-prone busywork and freeing experts to do… expert work.
Founder Notes: Hiring, Cash, Sales
“Hiring is your most important job. Hire slowly, act fast on orange flags.”
Bootstrapped: revenue funds growth → cash discipline is non-negotiable
Sales superpower: listening
Expect no’s. Churchill rule: move from failure to failure without loss of enthusiasm.
Start Now. Start Small. Play.
“Mastery in AI is perishable. Even the experts aren’t experts for long.”
Don’t wait for certainty. Pick one process and automate it.
Be ready to feel incompetent—everyone does.
Treat failure as R&D, not a verdict.
Craig’s Definition of Success
Relationships that endure
Experiences that make life vivid
Work with purpose that’s exciting, useful, and a little uncomfortable
Advice to his 22-year-old self: Take more risks.
Watch the Full Conversation
