Every cannabis brand is fighting for shelf space. But Jaime Lipowitz realized early on that shelf space was never the point—the person standing in front of it was.

Jake and Duffy sit down with Jaime Lipowitz, founder and CEO of High Buds Club, who built a 7,000-member budtender community from scratch with $5,000 and zero outside funding. It started with a single moment in a Venice Beach dispensary, when a budtender flipped her purchase decision in thirty seconds flat. She flew home to Toronto and started building the playbook for how brands actually win at the shelf in Canada.

Jaime doesn't mince words. She'll tell you why your store drop-bys aren't working, why THC percentage is not a story, and why the budtender is the most undervalued person in the entire cannabis supply chain.

If you're trying to figure out how to get your brand off the shelf and into someone's hands, this one is your blueprint.

Topics Covered:

• Why the last five feet of retail matters more than everything above it
• The Venice Beach moment that started it all
• Why dropping by dispensaries is mostly a waste of time
• How to build a community people actually show up to
• Why most cannabis brands don't have a story—just a spec sheet
• What Sephora, Diet Coke, and RC Cola can teach cannabis brands
• Building as a lone founder in a boys' club industry
• Why attention—not samples—is the real product

About Our Guest: Jaime Lipowitz is the founder and CEO of High Buds Club, an online community and media platform connecting cannabis brands with budtenders across Canada. With a background in advertising, media sales, and influencer marketing, Jaime saw the budtender as the most critical and most ignored link in the cannabis retail chain—and built an entire business around that conviction, entirely bootstrapped.

Links & References:

• High Buds Club

Some people find cannabis through opportunity. Jesse Redmond found it through his father—a man who spent decades managing chronic pain with opioids before cannabis changed everything. That personal story became the thread that pulled Jesse out of a successful finance career and into an industry he couldn't walk away from.

Jake and Duffy sit down with Jesse Redmond, Chief Strategy and Investor Relations Officer at Leef Brands, to talk about one of the more unlikely origin stories in cannabis. From allocating over a billion dollars in hedge fund strategies to running a dispensary out of Santa Barbara with his mom doing deliveries—Jesse has seen this industry from nearly every angle. Now he's back in the operator seat, building what might be one of the most compelling cultivation stories in the country.

If you care about where the money is—and isn't—in cannabis right now, this one's worth your time.

Topics Covered:

• Why Jesse walked away from finance to open a dispensary
• His father's journey from 1,000mg of Oxycontin a day to cannabis
• The state of cannabis capital and why the industry feels stalled
• What Leef Brands' 1,900-acre ranch changes about their cost structure
• Why half of California flower that passes as flour fails when concentrated
• Interstate commerce, Schedule III, and what actually unlocks next
• How to position your cannabis business as an acquisition target—not a casualty
• What Jesse tells young people who want to get into the industry

About Our Guest: Jesse Redmond is Chief Strategy and Investor Relations Officer at Leef Brands. He began his career at Franklin Templeton and Fisher Investments, co-founded two hedge funds, and allocated over a billion dollars to hedge fund strategies before closing his fund to open a dispensary in Santa Barbara. He has since become one of the most respected cannabis analysts in the space, leading research at Water Tower Research and co-hosting the Higher Exchanges podcast with Morgan Paxhia of Poseidon.

Links & References:

• Leef Brands
• Higher Exchanges Podcast
• Poseidon Investment Management
• Charlotte's Web
• Water Tower Research

Cannabis has no shortage of storytellers. What it's short on is people who can turn those stories into assets that actually get priced, sold, and survived. In this episode, Duffy sits down with Seth Yakatan—dealmaker, capital raiser, and one of the loudest voices in the room when it comes to what's real versus what just sounds good on a slide deck.

Seth has spent 30 years closing deals across pharma, biotech, CPG, and cannabis. He's raised over a billion dollars, sold more than 20 companies, and he doesn't sugarcoat what it takes. From which states are actually on fire right now to how smaller operators should be positioning for consolidation—and why making as much money as possible today is the whole strategy—this one is dense with perspective you won't get anywhere else.

If you're building, investing, or trying to figure out where this industry is headed next, pull up a chair.

Topics Covered:

• Why cannabis is a collection of assets, not a collection of businesses
• The states Seth would bet on right now—and the ones he's out on
• What the Willie's deal actually says about hemp investment
• How the Farm Bill opened Pandora's box (and who got hurt)
• The three business models that actually generate cash flow
• How smaller operators should position for acquisition
• Why point-of-sale incentivization might be the industry's biggest unlock

About Our Guest: Seth Yakatan is a veteran dealmaker and capital markets strategist with over 30 years of experience across pharma, biotech, CPG, and cannabis. He has raised over $1 billion and advised on more than 20 transactions. Known for his unfiltered takes and deep industry relationships, Seth operates at the intersection of strategy, storytelling, and getting deals done.