Building The Companies That Power The Agentic AI Revolution

At Dread Pirate Group, we're not theorizing about the future, we're building it. We're aggressively investing and building the next generation of AI and agentic commerce companies that connect brands and consumers.

Why This? Why Now?

We're at a moment in time when we have an opportunity to reimagine how technology serves people. For the last 30 years we have seen a handful of technology companies abuse peoples' trust by invading privacy and harvesting data that feeds weaponized algorithms to make hundreds of billions of dollars selling interruptive digital advertising. We are now seeing the horrific costs of this predatory monetization of attention in our society and youth. With agentic AI we will provide alternatives to the walled garden approach to return sovereignty to individuals and creators with tangible benefits to humanity.

And the Dread Pirate name? A nod to The Princess Bride. Like the Dread Pirate Roberts, AI may look like the villain, but we see it as the hero hiding in plain sight.

Portfolio Company Investments

Our Investment Thesis:

We are a venture studio of experienced operators who collapse the traditional venture model to create a virtuous ecosystem of AI driven, disruptive commerce.

Our companies address critical pieces of the agentic commerce puzzle from the user interface and the shoppable media layer to the infrastructure that makes transactions possible, creating a flywheel that compounds value within the agentic commerce space.

Our Mission

Our mission is to transform people's daily digital lives by building companies that use agentic AI to create and seamlessly deliver frictionless, rewarding experiences.

Our Values

We are mavericks and disruptors who subscribe to these core beliefs:

Meet the Dread Pirate Team

Speed + Talent + Capital. This isn’t theory. It’s execution. Our DNA is evident in every major technological advancement in commerce since the last century. Dread Pirate Group is a team of inventors and operators building agentic AI companies that improve people’s lives.

Jeff Sampson | Managing Partner

CEO|7x Founder|Agentic Commerce Pioneer

30+ year career dedicated to understanding and improving how people discover and purchase products. Ex-Microsoft Director of Global Product Management. Former VC and serial founder building disruptive companies with AI/ML technologies. As co-founder of Dread Pirate Group, he is shaping the future with agentic commerce.

Chip Wilson | Partner & CFO

9x CFO|Former VC|Investment Banker

30+ years of experience as both a CEO and CFO. Industries ranging from technology to consumer products. Ex-banker with track record raising capital, M&A, and closing deals. Co-founder of Everscore with Jeff Sampson and Steve Milton.

Kevin Brackney | Partner

CTO|2x Founder|Consumer Tech Leader

Specializing in large-scale ML and AI systems for consumer technology companies. With a track record spanning successful exits, zero-to-one company building, and enterprise-scale architecture, Kevin combines technical depth with strategic leadership to transform complex data challenges into differentiated products and platforms. He pioneered location intelligence technology alongside the founding team at PlaceIQ. At MapQuest (acquired by Verizon in 2017), he built and led the Data-as-a-Service team as Principal Architect. Most recently, he co-founded Spark Studio with Jeff Sampson.

Jason Hardi | Partner

Inventor|AI Strategist

Visionary inventor, prescient cultural savant, and serial entrepreneur. Pioneer of smart headphones with 175+ patents. Founder of Muzik, possessing an unmatched intuition for where consumer attention is heading next. Co-founded Prodigy Labs with Jeff Sampson to define the future of human-AI interaction through an emotionally intelligent agentic UX.