Andrew DeAngelo and his brother Steve were legacy cannabis market entrepreneurs and “reluctant activists” before founding one of America’s most iconic cannabis businesses, Harborside Health Center Oakland in 2006. The DeAngelo’s helped pave the way for today’s legal cannabis industry, and in its heyday, Harborside was the “largest medical cannabis retailer in the world.” But when Harborside tried to expand into other states, Steve’s cannabis felony proved too big a barrier. The DeAngelo’s retreated to California, but needed investor capital to survive that difficult market, precipitating a less-than-desirable exit. Some takeaways from DeAngelo’s story: When a locale or state doesn’t want your business in them, don’t fight to stay. Leave. Leaders need to create a family environment amongst the team while ensuring discipline and professionalism.   Being an activist company is good for business Expanding brings unexpected costs that could either sink your business or require to you to seek outside capital. When negotiating your exit, you need to know advocate for yourself and know how to horse trade. Who is Andrew DeAngelo? Andrew DeAngelo is a cannabis industry consultant in Oakland, California, and co-founder of one of America’s most iconic cannabis businesses, Harborside Health Center Oakland. DeAngelo served as Harborside’s general manager, director of operations, and chief revenue officer until departing the company in 2018. He cofounded the Last Prisoner Project in 2019 and currently chairs its board of directors. DeAngelo launched Andrew DeAngelo Consulting out of Oakland in 2020 to provide strategic advice to cannabis businesses. Before cannabis, DeAngelo was a professional actor who aspired to be Jack Nicholson, and does a convincing Joker laugh.