How Brendan Kennedy Made Cannabis Sound Inevitable (When Everyone Said It Was Impossible)
Brendan Kennedy pitched institutional investors on legal cannabis in 2011. His approach reveals a framework that works for any "impossible" idea.
By Eric Janssen
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In 2011, Brendan Kennedy left Silicon Valley Bank (SVB) Analytics to pursue an idea that sounded, at the time, almost unpitchable: build an institutional-grade investment firm focused exclusively on legal cannabis companies.
He wasn't selling a physical product. He didn't have an MVP, early sales, or the usual proof points investors expect. Instead, he was asking people to invest in an idea—a data-backed thesis about how cannabis legalization would unfold, and why the eventual winners would be built before the market felt "safe."
Eight years later, Fortune magazine profiled him as "The Marijuana Billionaire."
That outcome was the result of Kennedy co-founding Privateer Holdings, which went on to build and invest in companies like Leafly, Marley Natural, and Tilray—the first pure-play cannabis company to go public on the Nasdaq. Those companies collectively raised hundreds of millions of dollars, including Tilray's $150 million IPO.
On the Sales Reframed podcast, I sat down with Kennedy to unpack how he learned to pitch an idea that was well ahead of its time.
His approach mirrors, almost perfectly, a simple pitch framework I teach called GPS:
(G) Grab attention — Earn the right to keep talking
(P) Present the problem — Frame the opportunity in language your audience recognizes
(S) Show your solution — Make your solution feel like the logical next step
Kennedy's story is a masterclass in this framework. Here's how he did it.
Earn the Right to Be Heard
Most founders think the opening of a pitch is about explaining. It's not.
Kennedy said something in our conversation worth repeating: "The best pitches tell a story. There's a value proposition pitch. There's a product pitch. There's a problem-solution pitch... but the best of the best tell a story."
Before Privateer Holdings ever tried to persuade investors with data, Kennedy and his partners focused on something more fundamental: being intentional about their story.
They asked themselves: What will people assume about us the moment we walk into the room? And how can we flip that narrative to stand out?
In cannabis in 2011, the stereotypes were dominating headlines. So they differentiated.
They showed up professional. Suits. Haircuts. A deliberate absence of counterculture branding. As Kennedy describes it: nothing "green and 420," no "leafs all over the place," no "Cheech and Chong." Instead: professional, deliberate, credible.
They were also intentional about the language they used. Kennedy explains that they intentionally used one word—"cannabis"—and consistently corrected reporters who used other terms like "marijuana" or "weed."
Why does this matter? Because in the first moments of a pitch, your audience isn't evaluating your logic. They're deciding whether you're worth their time, what category to put you in, and whether you can be taken seriously.
Kennedy's intentional preparation didn't close a deal in 30 seconds. But it earned him credibility and the opportunity to hear investors say: "Tell me more."
The lesson: If you can get someone to think, "This isn't what I expected," at the very beginning of your pitch, and lean in to listen, you've already won the first round.
The Problem Isn't Convincing Them It's Big—It's Convincing Them It's Now
Once you have attention, you have to give it direction. This is where most pitches fall apart. They either jump into features, drown the room in abstract vision, or present numbers without a story that makes those numbers meaningful.
Kennedy and his team took a different approach. They focused on helping investors recognize an opportunity the market hadn't fully named yet.
The first step was understanding the true scale of cannabis consumption. Kennedy describes their process:
"We were trying to understand how much cannabis is consumed in the United States and around the world. I think we did it like 20 different ways. But no matter how we did it, we kept coming up with roughly $50 billion in the U.S. and roughly $200 billion globally."
That insight was critical. It showed that the industry wasn't a speculative niche. It was a massive, underserved market constrained not by lack of demand, but by laws and social norms that were already beginning to shift.
But Kennedy and his team didn't stop at market size. They added a second, powerful layer: timing.
By analyzing polling data, they noticed that public opinion on cannabis closely mirrored polling on gay marriage. The trendlines were nearly identical. Cannabis was simply "four or five years behind." Public sentiment was moving steadily toward broader acceptance and eventual legalization.
This comparison did something brilliant: it took an abstract prediction ("cannabis will be legal someday") and anchored it to a recent, concrete example that everyone had witnessed (the rapid shift in gay marriage acceptance). Investors could see the pattern.
The problem Kennedy pitched wasn't "cannabis is illegal." It was "delaying action means forfeiting first-mover advantage in a market that's already beginning to unlock."
The lesson: The problem frame isn't just about proving a problem exists. It's about helping your audience recognize that an opportunity is real, in language they understand, and showing them why it matters now.
Show Your Solution as the Logical Next Step
Once you've earned attention and framed the opportunity in a way your audience can recognize, the job becomes simple: make your solution feel obvious.
That's what Privateer Holdings did.
Reflecting on that early pitch, Kennedy told me how unusual it was. There was no product, no traction, no operating company to point to. The pitch wasn't "Cannabis is going to be big, so give us money."
It was a thesis built on clear beliefs:
"Cannabis is a mainstream product consumed by mainstream people."
"The end of prohibition is inevitable."
"Brands will shape the future of the industry."
If those beliefs were true, the market was real, and barriers were breaking down, then the logical next step was to build an institutional platform that could professionalize it.
But why should investors bet on Privateer specifically? This is where credibility becomes critical.
Kennedy and his co-founders had studied entrepreneurship at Yale, then spent five years at SVB Analytics valuing venture-backed companies and listening to hundreds of founders pitch their version of the future. That unique experience gave them an advantage investors recognized immediately: the ability to evaluate early-stage companies before markets fully formed and identify which ones would win once legalization arrived.
They weren't just backing a thesis about cannabis. They were backing Privateer's judgment about which companies would be worth owning when the market opened.
But Kennedy's first real test of the pitch didn't happen in a boardroom. It happened in a living room.
Before Privateer raised outside capital, Kennedy walked his former boss, Jim Anderson, the founder of SVB Analytics, through the idea. The goal wasn't to "sell" him on investment, but to clearly explain what they were building as a professional courtesy.
But the clarity of the pitch created confidence. Anderson became one of Privateer's first investors, a decision that ultimately returned more than 100× on his early investment.
The lesson: The solution portion of a pitch isn't about persuasion. It's about alignment. When your solution flows logically from the problem you've framed, and you're a credible person to execute it, the solution feels like the natural next step.
Clarity Over Flash
Kennedy's story is a reminder that great pitching isn't about being flashy. It's about being clear.
And when you're pitching something non-obvious, something that sounds impossible until you explain it, clarity isn't a nice-to-have. It's everything.
That's the power of the G.P.S. framework:
Grab attention without gimmicks. The goal isn’t to convince, it’s to get listeners to lean in.
Present the problem so it feels real and urgent. Use data and analogies that help your audience see what you see.
Show your solution as the logical next step. Make it obvious why you're the right solution to address the problem.
Bad pitches happen. But if you're willing to add structure in a way that makes the value obvious, your next pitch might be the one that lands.
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Eric Janssen teaches sales and entrepreneurship at the Ivey Business School at Western University. He is the founder of the Founder Sales Sprint and host of the Sales Reframed podcast, where he interviews Brendan Kennedy in Episode 5.
