Our Team
Kyle Andersen - Founder and Managing Partner
With nearly a decade in logistics, Kyle learned that most supply chain challenges come down to one thing: a lack of clear, honest insight. He built his career by taking a deeply analytical approach to freight data, uncovering hidden costs, misaligned lanes, and operational blind spots that quietly drain profit. Known for his straightforward, no-nonsense style, he’s helped fast-growing CPG brands strengthen their operations through transparency, smarter decision-making, and a focus on what actually moves the needle.
That passion for clarity, and for doing things the right way, is what led him to create Loon Advisory. Rooted in Midwest integrity and a genuine desire to help founders succeed, Kyle brings companies the unbiased visibility and strategic guidance they need to scale confidently. His mission is simple: eliminate the guesswork, reveal the opportunities, and give every business a supply chain they can trust.
Caleb O'Reilly - Board Founder and Advisor
Caleb O’Reilly is one of the founding members of our board and brings a strong strategic mindset shaped by more than 12 years in the logistics industry. As the Director of Sales at Gold Star Transportation, he has built a reputation for driving growth, cultivating high-value partnerships, and implementing operational improvements that support long-term business success. His depth of industry knowledge and commitment to excellence make him a valuable contributor to our organization’s direction and decision-making.
Outside of his professional achievements, Caleb is known for his well-rounded personal interests and his dedication to living a full, active life. He enjoys spending time outdoors on the golf course, staying competitive on the pickleball court, and prioritizing quality time with his wife, Nadia. He’s also a devoted English Bulldog enthusiast, bringing the same enthusiasm and warmth to his personal life that he brings to his work and board service.