A holding company built on doing things the right way.
Starboard Investments was founded in 2010 in Birmingham, Alabama. What started with restaurant operations has grown into a portfolio spanning quick-service restaurants, health and wellness, and technology.
Through Captain Intelligence, Starboard has moved into artificial intelligence, building AI-powered tools and consumer applications. Operators who understand AI will define the next era of business.
The approach is simple: find good businesses, roll up our sleeves, and make them better.
Brandon Stewart founded Starboard Investments with a focus on hands-on business operations. He has built and managed ventures across restaurant operations, fitness, health and wellness, and technology — including operating restaurants as a managing owner. Today, he is focused on the intersection of traditional business operations and artificial intelligence.
Quick-service restaurant locations across Alabama.
AI-powered tools and consumer applications.
IV therapy and wellness. Equity stake.
AI document scanner. App Store.
Health data decoded. AI insights.
AI-powered business services.
Restaurant equipment repair management.
Voice AI for restaurant ordering.
Franchise discovery platform.
Brandon Stewart is the CEO of Starboard Investments, a Birmingham, Alabama-based holding company with operations spanning restaurants, technology, health and wellness, and artificial intelligence. He is a multi-unit operator turned AI builder.
Brandon graduated from the University of Georgia with a degree in finance and began his career in investment banking in Charlotte, North Carolina. He then moved to Boston to join Weston Presidio, a private equity firm whose portfolio included Jimmy John's. That experience gave him a front-row seat to the franchise model and sparked a passion for restaurant operations.
In 2011, Brandon moved to Birmingham and opened his first Jimmy John's location. Over the next several years, he scaled the business to 62 units across three states, learning the operational realities of multi-unit ownership at scale — labor, training, real estate, and the unglamorous work of running a service business well. In 2024, he acquired 43 restaurants in Birmingham and South Alabama, which he operates today as managing owner.
By 2025, Brandon began experimenting with AI inside his own operations — using Claude and other tools to streamline reporting, decision-making, and back-office work across his restaurants. What started as personal productivity tools turned into measurable operational improvements, and the work caught the attention of Austin and Robert at Caravan AI.
In March 2026, Brandon joined Caravan as part of the team, helping bring hands-on, in-person AI training to operators and businesses across the country.
Today, Brandon focuses his energy on the intersection of traditional operations and artificial intelligence. He believes the next decade belongs to operators who can pair domain expertise with AI fluency, and he is building, teaching, and speaking with that thesis in mind.
In 2020, Brandon founded Pay It Forward Alabama, a charitable organization dedicated to fundraising and giving back to the Birmingham community. He serves on multiple boards including the Birmingham Zoo, Boys and Girls Clubs, and First Light Shelter.
How traditional business operators can adopt AI without a technical background. Real tools, real results, no hype.
Lessons from building 62 Jimmy John's locations and operating 43 restaurants. What works, what breaks, and what the data tells you.
The journey from investment banking and private equity to hands-on franchise ownership. Why operators who understand capital have an edge.
A practical framework for integrating AI into daily operations. What it takes to make AI useful in a real business — beyond the hype.
Building a business that gives back. How Pay It Forward Alabama grew from a simple idea into a platform for community impact.
Through Caravan AI, Brandon delivers hands-on training that teaches teams how to use AI tools effectively. Not theory. Execution.
Interested in having Brandon speak at your event or train your team? Fill out the form below and we will be in touch.
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