Jason Allen
Co-Founder, PILOT. Based in Austin and New York.
The Crooked Line
A professor once told me that when it comes to life and career, embrace the crooked line. I've been doing that ever since — probably more literally than he intended.
The path from political science to international development to venture capital to asset management to co-founding a technology company doesn't resolve into a tidy narrative. But it does resolve into something: a person who knows how to find the through-line in things that don't obviously connect, and build something from it.
I'm most at home in the space between disciplines — where the interesting problems live, where the people who've only ever done one thing tend to get stuck. That's where I do my best work.
I'm based between Austin and New York, and always glad to connect.
Collaboration
I'm most useful early — when the vision is clear but the structure isn't yet, when the brand and the business model are still being invented at the same time.
I work at the intersection of creative and commercial. That means I can hold the story and the spreadsheet in the same conversation without losing either. I'm drawn to problems that require both — positioning that has to survive a boardroom, brands that have to scale without losing their soul, strategies that are bold enough to matter and grounded enough to execute.
My best thinking usually arrives the day after — when I've had time to stay with a problem until I find where it maximally wants to go.
That's what I'm really offering: someone who doesn't just diagnose where you are, but keeps turning it over until they've found the highest version of what you're building.
I met my co-founders, David and Travis, in 2021 while I was working in finance at Dimensional. I knew early that this was the kind of work I was meant to do. (or at least more fun than Excel).
We started PILOT to reimagine how people experience culture in the real world. Today, PILOT is the connective tissue between sports, fashion, and world-class hospitality — a platform powering everything from New York Fashion Week to the sports leagues and five-star resorts.
And here’s what I’ve learned so far:
Entrepreneurship is not about proving your ideas right.
It’s about becoming someone capable of holding the weight of the thing you’re building. That changes you.
Before PILOT — Dimensional Fund Advisors, a $1T AUM firm that taught me how rigorous, long-term thinking actually operates at scale. Before that, politics: campaigns, the U.S. Senate, international policy work. What politics teaches you is how to move people — how to build advocates, land a message, make complex ideas feel urgent and human. I use that every day.
I studied political science at Duke and environment and development at the London School of Economics.
Fluencies
Strategy & Finance · Brand & Positioning · Communications · GTM · Operations
Experience
