Meet Duncan Littlefield
CEO / COO
Strategic Advisory
Startup Growth
Cross Function Integrator
Founder, Operator, Storyteller & Growth Partner
From the pressure of mini-tour greens to the boardrooms of high-growth companies, I’ve built a career on discipline, vision, and the ability to step up when it matters most. My years as a professional golfer taught me the value of long-term sweat equity, creativity, and precision, and I now apply those skills to scaling startups, advising founders, and driving operational excellence. Today, I partner with visionary teams to uncover untapped potential, tell undertold stories and create the operational frameworks that turn investments into lasting wins. Whether it’s incubating a new venture, guiding a portfolio company through a critical growth stage, or crafting the story that wins market share, I bring the combination of creative storytelling and sharp execution needed to deliver measurable results and long-term value.
A Question That Changed Everything
“What does a man with options have?”
My father’s question shaped my journey. I chased a single goal for years—and it opened doors I never imagined. Mini-tour life took me from green fairways to cramped hotel rooms and back, teaching me invaluable lessons about diverse cultures, human nature, and the power of perseverance.
…my fuel remains the same: a relentless focus on impact, collaboration with passionate people, and, yes, never turning down a good cup of coffee.
Past Work
In 2018, I founded The Littlefield Company, a video-production agency built to turn strategy and storytelling into measurable growth. Over five years, we produced sales-driven commercials for Fortune 100 brands, delivered campaigns across five continents, and saw our work land in national print. By 2023, I had exited the business, ready to apply my "0-1" mindset of scaling a creative team to bigger ventures.
That chapter has included partnerships and roles with Official, SketchDeck, a strategic advisory group where I partnered with founders, family offices, and venture-backed startups to navigate growth, operations, and fundraising. Along the way, I advised multiple companies across industries, combining creative direction with operational rigor. Whether leading M&A integrations, building go-to-market engines, or positioning brands for capital raises, my throughline has stayed the same: helping businesses move from idea to impact… faster, smarter, and with trust at the core.
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