There is a story that Queen Isabella of Spain was the first true VC. She “backed” an entrepreneur (Christopher Columbus) with capital (money, ships, supplies, crew) to do something that most people at the time thought was insane and certain to fail (a voyage) in exchange for a portion of the to-be-earned profits of the voyage that, while probabilistically unlikely, had an asymmetric payoff compared to her at-risk capital.

If you attended Harvard Business School, you may have read about a similar early VC-like tale here in the States in the 1800s—the whaling industry. Financing a whaling venture was expensive and fraught with risk but, when successful, highly profitable. In 1840s New Bedford, “agents” (today’s VC equivalent) would raise capital from corporations and wealthy individuals (today’s limited partners) to fund ship captains (entrepreneurs) to launch a whaling venture (startup company) in search of asymmetric returns that were heavily skewed to the top agents, yet often plagued with failure. Thirty percent of voyages lost money . . . .