Chip Cunningham


Co-Founder, & CEO



Chip’s life is a little "Hemingway", bush pilot, wildlife guide, fisherman, adventurer, and conservationist; but his greatest loves are his wife and two daughters.


Chip grew up on the shores of San Diego, playing every sport imaginable. He ended up excelling in tennis which led him to his first career after college, where he played all over the world. But, he had always yearned to fly, especially in Africa. So this naturally led to his next career as an aviator. He flew clients around East Africa, and would fly on game counts and anti-poaching missions. It was in Kenya where he met his best friend, James Tuleto Ole Sengeny. A lifelong friendship was born—one which spans cultural and continental divides. Together with his wife (the blonde), they rebuilt and took over the running of Ol Donyo Wuas and turned it into one of Kenya’s finest Safari camps. This chapter would in turn morph into his next career as he sought a chance to take on a different approach in the Safari world. He knew full well what an amazing yet mostly overlooked offering there was in Africa back then of small, independently owned camps and lodges or “Bush Homes.” He saw the need of promoting and selling these properties and teamed up with veteran travel visionary and guru Phil Osborne. Together with his wife Sandy, Phil Osborne, and Christine Mann, they grew the company from one destination to over 30 exciting adventure destinations worldwide.

Chip's keen sense of spirit and unbridled sense of adventure has kept Outside GO focused and evolving over the past 25 years, without ever compromising on integrity or quality.