Before Surf Air, Sudhin Shahani helped musicians sell songs from their fans’ web pages. His route from music to regional aviation and space investment follows a recurring question: what stands between people and the transaction they want to make?

After managing a $50 billion real estate portfolio through the financial crisis, Chad Anderson went to Oxford to change direction. He came back with a case for investing in space - and an appetite for expeditions with unusually complicated drinks menus.