Chris Woolley is a bank founder, business advisor, mentor, and investor in a variety of companies and funds. From 1990 through 2005, he held various senior and executive business banking positions with Wells Fargo, Imperial Bank, and Comerica Bank.

In 2005, Chris co-founded de novo business bank Square 1, which raised $105 million in initial capital. He had executive responsibility for offices in San Diego, Orange County, Los Angeles, Palo Alto, Seattle, Denver, Austin, Houston, Chicago, Boston, and Durham. Square 1 went public in 2014 and was successfully sold in 2015.

In 2016, Chris became a Founding Director and investor in Endeavor Bank, a de novo community business bank which trades on the OTCQX (EDVR). Endeavor opened in 2018 after a successful capital raise of $26.5 million from individual investors and business owners. The Bank completed an additional equity round as well as 2 sub-debt raises to support its expansion. It has grown to over $700 million in assets.