Boots on the ground.

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 Chairman

As the co-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. He then moved to Japan and worked for Peace Boat, eventually serving as their director of program development for international educational voyages. His field programs at Peace Boat focused on meaningful interactions and cultural exchanges with local communities, service efforts, and unique educational and enrichment opportunities for passengers.

From these efforts, Carl was 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, he 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.


Christopher Shephard, Co-Founder and President

Chris has developed extensive travel itineraries throughout Europe, South America, the Middle East and Central Asia. In addition to serving as a tour program leader, Chris has spent much 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. 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 currently working on a Ph.D. in International Education at Columbia University.


IMG_5391Jordan Valdés, Chairwoman of the Board

As Chairwoman of Insider’s Board, Jordan’s 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’s value to the Insider board is a linchpin for its success.

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 as 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, on issues ranging from carbon finance to supply chain and logistics. Oh, and she 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.


Mary Bruce, Director, Special Projects Advisor

Mary has more than a decade of experience directing creative travel itineraries, major events, as well as strategic planning for national nonprofits. She’s traveled the globe, worked with media from Al Jazeera to NPR, and has specialized in customizing service-learning experiences domestically and abroad.  Mary’s first trip overseas was in high school, visiting Strasbourg, France, where she learned the benefits of living above a bakery, especially one just a short drive from the largest beer cask in the world.  She also lived in Morocco for two years while serving in the Peace Corps.

Before joining Insider Expeditions, Mary was the Co-Executive Director of AmeriCorps Alums, supporting 1 million alumni to plan their own life’s adventures and designing affinity experiences for an incredibly diverse membership base. She studied Arabic, Spanish, French, imiq Tamazergt, and ilan Tagalog. Mary graduated with highest distinction from the University of Virginia and also received her MPA from the Woodrow Wilson School of Public and International Affairs at Princeton University.

CherineHeadShot3Cherine Badawi, Trip Director

In search a wild and well-lived life, Cherine has lived extensively in six countries and traveled to more than 50. Her work has ranged from strumming guitar on street corners to working as an international journalist to serving in the United Nations. She especially enjoys planning exceptional travel and cultural programs for younger groups.

Highlights of Cherine’s past professional experience include writing Footprint’s Travel Guide to Egypt and serving as a senior trainer for Challenge Day, an innovative peace program featured on the Oprah Winfrey show and MTV. Cherine also served as the Curriculum and Training Director of The Mosaic Project and worked as the Experiential Education Specialist of a transnational floating university, The Scholar Ship. Most recently Cherine had the privilege to speak at a UN High Level Forum on The Culture of Peace.


Elise Webb, Trip Director

Elise has ten years of research and program development experience in a career that has taken her around the world. She’s run the gamut, from working as a nine-to-five pilgrim in Plymouth, Massachusetts, to evaluating NGO programs in Rwanda—where her flailing muzungu moves won her a dance contest. Elise loves helping people as they traverse the globe, and recently spent two years in Thailand assisting individuals in crisis while working in American Citizen Services at the United States Embassy in Bangkok.

Elise has a master’s degree in global comparative sociology from The Catholic University of America and a bachelor’s degree from Loyola University Chicago. When she was deciding her undergraduate semester abroad program, she threw a dart at a map of Europe and it landed in Prague. With that, a globetrotter was born. She takes that sense of adventure with her into the unexpected as she plans off-the-beaten-path trips for others.

Nate 2Nate Hodson, Trip Director

Nate is a PhD candidate in Near Eastern Studies at Princeton University,  and has spent a great deal of the past decade on the road. His first trip to the Middle East was to Morocco in 2003, and he’s since been to nearly every Arabic speaking country (highlights include Oman, Saudi Arabia, Syria and Yemen). He’s also traveled widely outside the region and has collected a story or two from Pakistan, India, Laos, Colombia, Brazil, the Galápagos Islands, among other places.

Nate appreciates fixed prices, but in a haggling situation he has a pretty keen sense for when a merchant has accepted his “final offer.” He speaks Arabic well and occasionally takes steel wool to his rusty German, French and Persian.


Robert Lord, Trip Director

Rob comes to Insider Expeditions with a background in events and project management, having tackled everything from annual conferences and board meetings to charity auctions and concerts. He’s even helped manage several major construction projects in New York City.

During his time living, teaching, and traveling in Spain, as well as backpacking throughout South America, Rob has cultivated a love for teasing out the most interesting features, history, and hidden wonders in any new environment. In turn, he has passed along this knowledge by developing experiential learning curriculum for both American and international audiences.

Rob graduated with a degree in political science from American University, where he learned the importance of fostering cross-cultural connections and creating opportunities for reflection on the similarities and differences that make us all human. He is happy to lend this expertise in the interest of planning and executing the most amazing educational travel experiences for our Insider clients.

IE profile picDaniel 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 geniuses, 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.


1345df64-82e8-4f40-b091-5ee1c05cf69dDara Goldberg, Logistical Mastermind

Dara has over five years of sales and marketing experience with an international hotel chain with luxury and boutique and funky hotels across six continents. She thus can help our clients choose the very best of places to stay, no matter where we are traveling. Dara is also an active volunteer with several charities that assist the homeless and the blind and she is passionate about animals. She is currently an avid student of improv comedy and a lifestyle blogger to boot.

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, an M.Sc. 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 put unparalleled, unexpected surprises via his creative genius into every single program.

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