Insider Expeditions takes great pride in having one of the most experienced and talented teams in the industry. Together we speak over seven languages and include alumni from Yale, Harvard, Princeton, MIT, Stanford, Columbia, UC Berkeley, American University, and other top educational institutions in the country.

Carl Shephard, Founder and Chief Executive Officer

As the founder of Insider Expeditions, Carl is proud to have led educational programs in more than 100 countries. He began his service in enrichment travel in South America with a local tour operator, leading cultural exchanges, service projects, and innovative travel itineraries throughout the region. Honored with a World Peace Fellowship by Rotary International, he then moved to Japan and worked with Peace Boat, whose travel programs focus on meaningful interactions and cultural exchanges with local communities, service efforts, and unique educational and enrichment opportunities for passengers.  Carl was later recruited to design the in-country academic field programs across 14 countries for The Scholar Ship, a semester abroad program that brought students from around the world to live and study together on a seafaring voyage.Later as a political appointee and United States diplomat, Carl also had the opportunity to organize trade missions and business delegations for membership organizations to more than 30 countries.Carl graduated Phi Beta Kappa from Yale University and earned a master’s degree in international relations while serving as a World Peace Fellow in Tokyo. He speaks Spanish and Japanese.


IMG_5391Jordan Valdés, Chairwoman of the Board

As Chairwoman of Insider’s Board, Jordan’s trip involvement ranges from developing and maintaining Insider’s relationships in Cuba, to identifying strategic Insider partnerships and crafting new Insider adventures across the Cuban island. With unparalleled connections at home and abroad, and a unique ability to problem solve in even the trickiest scenarios, Jordan is key to our Cuban excursions.

Jordan has lived around the world, with extensive professional and travel experience across Europe, the Middle East, Asia, and Latin America. She is also a passionate policy advisor, and served President Obama as a senior advisor in the Office of International Trade in the Small Business Administration (SBA). Prior to her work at SBA, Jordan advised the US Agency for International Development, the Department of Energy and the World Bank in various projects from Latin America to Africa to Bangladesh. Her work encompassed issues ranging from carbon finance to supply chain logistics. She also has served as a Senior Advisor to the Prime Minister of Bahrain. Jordan is fluent in Spanish and French and conversational in Arabic and Italian.

Julia Sommer, Operations Director

Currently residing in New York City, Julia is a Swiss-American with over 8 years experience in travel, events, and marketing. She is a dynamic experiential architect and passionate group trip leader.  Together with Insider, Julia successfully co-launched an innovative group travel program featuring adventure getaways and immersive cultural excursions; this venture led her, along with 500 passionate globetrotters, on a voyage to conquer 7 continents in a single calendar year!




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Daniel Peterson, General Counsel

Dan serves as an outside general counsel for small businesses and non-profits. He specializes in assisting organizations with outsized legal needs, such as B2B companies and those in regulated industries (like travel companies operating in Cuba under exceptions to the U.S. embargo). His other clients include auction experts, biotech prodigies, and pinball wizards.

Dan graduated from Yale University and the Georgetown University Law Center. In-between, he taught scuba diving on the Great Barrier Reef and sailing in the Caribbean and Hong Kong. Dan is currently on hiatus from international travel until his two daughters are old enough to carry their own stuff.


Alex Boxer, Creative Genius 

Alex is a physicist by day and a travel guru by night. As an expert in oceans and ocean technologies, he has traveled extensively both above and below the waves throughout the Pacific, the Middle East, and Europe. Alex has a passion for technology from all eras, from modern neural networks to medieval astrolabes.

Alex holds a Ph.D. from MIT in plasma physics, a master’s in the history of science from Oxford, and a bachelor’s degree in classical languages from Yale. He is pretty much the smartest person we know, which helps to create unparalleled, unexpected surprises via his creative genius into every single program.



Christopher Shephard, Co-Founder

Chris helped start Insider twelve years ago, and has developed extensive travel itineraries throughout Europe, South America, the Middle East and Central Asia. In addition to occasionally serving as a tour program leader, Chris currently spends most of his international working life seeking to improve the conditions of developing countries. He has served the United States Agency for International Development in both Iraq and Afghanistan, focusing on education and health issues in those countries, and is currently finalizing a tour in Jordan. Chris began his career as an experiential educator and tour leader, directing programs for the Princeton Blairstown Center.

Chris earned his bachelor’s degree from Princeton University and holds a masters in international development from the Johns Hopkins School of Advanced International Studies. He is also currently working on a Ph.D. in International Education at Columbia University.

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