With an MBA from Yale and a career as a venture capitalist in Silicon Valley behind him, Brendan Kennedy hardly fits the image of the tie-dye-wearing ganjapreneur looking to cash in on the promise of legal pot. In fact, Kennedy, who founded the nation's first private equity firm dedicated to marijuana, admits he has limited experience smoking cannabis. And yet Kennedy's Privateer Holdings—which operates Leafly, the Yelp of pot—is poised to become a major player in Washington state's legal marijuana trade.

Kennedy, who has appeared in Forbes, The Economist and The New York Times, wouldn't be in the business if he didn't see legalization coming south to Oregon and beyond. His cautious but optimistic approach is a hopeful sign of how things will work in the world of professionalized pot.

"We've made trips to Washington, D.C., and spoken with a dozen U.S. representatives and senators about this issue, and there's something about talking to a senator in their office and being a representative of a legal cannabis industry and having them take us seriously," Kennedy says. "It gives us confidence that legalization is inevitable. Time and demographics are on our side."

Originally shy about investing in companies that directly touched cannabis because of federal prohibition, Privateer, founded in 2011, has quickly moved closer to embracing cannabis production. In Canada, which recently overhauled its medical-marijuana laws, the company has applied for a 70,000-square-foot medical cannabis grow on Vancouver Island. Privateer also created a subsidy called Arbormain, which has leased multiple warehouses in Washington state with plans to sublease to a few select producers.

Why the new courage? Kennedy cites a U.S. Department of Justice memo from August 2013 announcing the feds would allow the Washington and Colorado experiments to go ahead provided that lots of pot wouldn't end up crossing state lines or wind up in the hands of children. Then came the successful rollout of pot shops in Colorado last month and the intensive rule-making process with the Washington State Liquor Control Board, charged with implementing recreational cannabis, which has allayed concerns of the feds.

To manage all this, Privateer made another splash by hiring a high-ranking Drug Enforcement Administration  agent formerly based in Portland to become the company's director of compliance. "It represents one more crack in the Berlin Wall of cannabis prohibition," Kennedy says.

"It's all about managing risk," he says. Today, much of it is still "unquantifiable," but whatever quantity there is seems to be dissipating through the thin Denver air.

"The world's first regulated pot shops opened up and the world did not end," Kennedy says. “Oregon is going to legalize cannabis next November.” 

Philip Dawdy, a former Willamette Week and Seattle Weekly staff writer, is the author of much of Washington's current medical-cannabis law and has also co-authored two legalization initiatives. He is a political and business consultant in the cannabis industry and is also a founder and executive vice president of Cascadia Growers Association, an applicant for cannabis production and processing licenses.