High Touch with Jake & Duffy

The Last Five Feet | Jaime Lipowitz

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 [https://www.highbudsclub.com]

A Higher Calling | Jesse Redmond

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 [https://www.leafbrands.com] * Higher Exchanges Podcast [https://www.higherexchanges.com] * Poseidon Investment Management [https://www.poseidon.eco] * Charlotte's Web [https://www.charlottesweb.com] * Water Tower Research [https://www.watertowerresearch.com]

Deals, Distress & What It Actually Takes to Win | Seth Yakatan

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.

Hospitality, Hemp & the Future of Adult Beverage | Jon Halper

When people talk about retail disruption, they usually focus on pricing, scale, or e-commerce. But in this episode, we get specific about the thing most operators miss: how hospitality turns a “routine run” into a real experience—and why that matters even more as new categories like hemp THC explode. Jake and Duffy sit down with Jon Halper, CEO and owner of Top Ten Liquors, to unpack the playbook behind one of the most innovative independent beverage retailers in the country. From competing head-to-head with Total Wine to building a 150,000+ member loyalty engine, Jon breaks down what it takes to scale service, design promotions that create credibility, and lead through the messy reality of regulation—especially as hemp THC beverages reshape consumer behavior. If you care about modern retail strategy, experiential merchandising, or where alcohol, hemp, and cannabis collide next, this one’s for you. Topics Covered: * How an “outsider” perspective helped Top Ten out-innovate legacy liquor retail * Building a service culture that scales (and why short lines aren’t the goal) * The loyalty + club pricing model behind 150,000+ members * Sunday Specials and the difference between a promotion and a brand-killer * Why THC beverages took off—and why most customers still haven’t tried them * The compliance + education playbook for selling hemp THC responsibly * What AI can (and can’t) replace in the in-store experience * Why hemp, cannabis, and alcohol should compete and collaborate About Our Guest: Jon Halper is the CEO and owner of Top Ten Liquors, a Minnesota-based retailer that’s grown from four stores to 15 (with more on the way). With a background spanning corporate law, retail operations, merchandising, and leadership, Jon has built Top Ten into a modern “adult beverage store” known for customer experience, smart pricing strategy, and early leadership in hemp-derived THC beverages. Links & References: * Top Ten Liquors [https://toptenliquors.com/]

From Luxury Fashion to Cannabis Tech | Melissa Hanson

What can cannabis learn from luxury fashion retail? Melissa Hanson, VP of Operations at Flowhub, brings decades of experience leading teams at Michael Kors and scaling cannabis retail at MedMen and Sunburn. Now at Flowhub, she’s focused on helping dispensaries operate smarter, smoother, and more profitably. In this conversation, Melissa explains why true retail excellence comes down to people, process, and purpose—not hype. She shares her philosophy on clienteling, building technology that empowers budtenders, and the importance of data-driven decision making in a fast-changing regulatory landscape. Whether you’re an operator, brand, or tech partner, this episode offers practical insights into creating cannabis retail experiences that last. Topics Covered * Lessons cannabis can borrow from luxury fashion retail * Clienteling vs. loyalty programs in dispensaries * How Flowhub’s tools support budtenders and operators * The pitfalls of chasing “shiny objects” in product strategy * Compliance complexity and adapting to shifting regulations * Upselling, promotions, and smarter inventory decisions * The role of empathy and culture inside Flowhub’s team * E-commerce and pre-ordering as game-changers for cannabis retail * Balancing open APIs with seamless all-in-one solutions * The future: data-driven operators and lighter regulatory burdens About Our Guest Melissa Hanson is the Vice President of Operations at Flowhub. She has led 500-person retail teams at Michael Kors, launched cannabis delivery operations at MedMen, scaled vertically integrated retail in Florida, and now helps dispensaries run smarter with technology that empowers their staff and streamlines compliance. Links & References * Flowhub: https://flowhub.com