Deep Cuts Live

About Deep Cuts Live

DEEP CUTS LIVE is a series featuring candid conversations and interviews with entrepreneurs and innovators.

Publisher

deepcutslive

Category

business

Language

en

Explicit

No

First episode

10 Mar 2021

Latest episode

18 Sept 2026

Latest episodes

134 episodes in the feed.

1. 

   18 Sept 2026

   Izzy Woods on Drew Estate, Cigar Pairings & Breaking Industry Stereotypes

   Izzy Woods has one of the more unusual résumés in the premium cigar industry. Before becoming Drew Estate’s Lifestyle Ambassador, she spent 20 years in education, worked in the spirits world, became a certified bourbon steward and learned firsthand that good sales often have less to do with talking—and more to do with listening. In Episode 179 of Deep Cuts Live, host Antoine Reid sits down with Izzy for a wide-ranging conversation about her journey to Drew Estate, the work that happens behind the scenes of one of the cigar industry’s most recognizable brands, and how she brings together cigars, spirits, events and consumer engagement in her role today. Izzy explains what being a Lifestyle Ambassador actually means when the cameras and Instagram posts go away. From early flights and budgets to hosting events, creating digital content and answering consumers around the world, she offers a look at the work behind a job that can appear from the outside to be one long cigar event. The conversation also turns to what’s next for Drew Estate. Izzy discusses the company’s move toward establishing a presence in the Dominican Republic and what that expansion means for a company so closely associated with Nicaragua. She also talks Deadwood, Herrera Estelí Habano, Undercrown Maduro and some of the cigars she believes deserve another look. Then the conversation goes beyond brands and blends. Izzy discusses why women haven’t suddenly “arrived” in cigar culture—they’ve been part of it all along. From sales and events to sorting, tasting and factory operations, women have long played important roles throughout the business. She also challenges the assumptions sometimes made when selling cigars to women and explains why the better approach is surprisingly simple: ask people what they actually like. And because you can’t have Izzy Woods on Deep Cuts Live without talking pairings, we put her skills to the test. What do you pair with a Saturday morning on the porch? A steak dinner? A football game? A first date? A beach vacation? A bad day at work? Or an all-day Golden Girls marathon? Izzy tackles them all while explaining how anyone can build better pairings—even if bourbon, rum or alcohol in general isn’t your thing. In Episode 179: • Izzy’s path from education to spirits and eventually Drew Estate • What a Drew Estate Lifestyle Ambassador actually does • Why listening may be the most important skill in sales • How digital media has changed cigar-industry engagement • What makes a memorable cigar event • Drew Estate’s Dominican Republic plans • Deadwood, Herrera Estelí and other Drew Estate favorites • Why women have always been part of cigar culture • What cigar marketing sometimes gets wrong about women • How to choose a cigar and beverage pairing • Coffee, tea, soda, mocktails and other non-alcoholic cigar pairings • Izzy takes on the Deep Cuts Live pairing lightning round Whether you’re interested in Drew Estate, cigar and spirits pairings, cigar marketing or simply the people working behind the scenes of the premium cigar business, Episode 179 offers a different look at what it takes to connect cigars with the people who enjoy them. Subscribe to Deep Cuts Live for more conversations with the people shaping premium cigars, entrepreneurship and cigar culture. ============================================= Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates. ============================================= Website: deepcutslive.com YouTube: youtube.com/deepcutslive Instagram: instagram.com/deep_cuts_live

2. 

   18 Sept 2026

   Why Wildfire Cigars Abandoned the Traditional Cigar Brand Playbook | Jeremy McDonald

   What happens when the traditional way of building a cigar brand stops working? Jeremy McDonald of Wildfire Cigars returns to Deep Cuts Live for Episode 178, five years after his first appearance—and a lot has changed. Wildfire has grown, the premium cigar business has evolved, and Jeremy has completely rethought how he wants to compete as a small independent cigar company. In this episode, host Antoine Reid talks with Jeremy about the realities of building a boutique cigar brand in a market where consumers constantly want something new, retailers have limited shelf space, social media attention can disappear almost instantly, and established brands are competing for the same humidor space. Jeremy explains why Wildfire recently moved away from the traditional model of building its business around permanent core lines. Instead, he's experimenting with a rotating portfolio of cigars, introducing a new blend roughly every five weeks through a select group of retail partners. Once a release is gone, it's gone—until the concept potentially returns in another form the following year. That leads to a bigger conversation about FOMO and collector culture. Antoine and Jeremy explore what the cigar industry can learn from Pokémon, action figures, sneakers, boutique guitar pedals and even Liquid Death—and whether cigar companies can make buying and discovering cigars feel more interactive and exciting. In Episode 178, we discuss: * How Wildfire Cigars has changed since Jeremy's last Deep Cuts Live appearance in 2021 * The reality of going all-in on your own business * Why Jeremy says entrepreneurship taught him humility * How cigar-buying behavior has changed * Why boutique brands are fighting harder for attention * The growing pressure to constantly release something new * Why Wildfire pivoted away from the traditional core-line model * Dead Drift, Faultline, Radioactive and the new Revivalist 2.0 * Wildfire's rotating monthly release strategy * Creating stronger partnerships with fewer retailers * Why some cigar shops are becoming more like sports bars—and what may be getting lost * What tobacconists can do to create loyal customers * FOMO, scarcity and the collector mentality * What cigars can learn from Pokémon, Mattel, Liquid Death and sneaker culture Jeremy's philosophy of keeping Wildfire authentic to who he is Jeremy also explains the deeper thinking behind Wildfire's branding. Every box contains an Easter egg in the form of an original quote that helps explain what that particular cigar means to him. For Jeremy, authenticity isn't simply a marketing buzzword—he wants the cigars, artwork, music and everything else he creates to feel unmistakably like him. If you're interested in premium cigars, boutique cigar brands, cigar marketing, entrepreneurship, retail strategy, branding or the business behind the cigar industry, this episode goes well beyond wrapper, binder and filler. ============================================= Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates. ============================================= Website: deepcutslive.com YouTube: youtube.com/deepcutslive Instagram: instagram.com/deep_cuts_live

3. 

   18 Sept 2026

   How a Cigar Sommelier Built His Own Cigar Brand | Don Emmanuel

   How do you go from studying cigars to creating your own—and then take that brand around the world? In Episode 177 of Deep Cuts Live, host Antoine Reid sits down with Don Emmanuel, founder of Don Emmanuel Cigars, to talk about his journey from cigar sommelier, educator and content creator to launching his own premium cigar company. Born and raised in São Paulo, Brazil, Don Emmanuel grew up with family connections to tobacco and later immersed himself in cigar education. He studied through the International Association of Cigar Sommeliers, became an educator himself, and eventually took everything he'd learned about tobacco, blending and the cigar experience and put it into building a brand of his own. Since launching at the end of 2023, Don Emmanuel says the brand has expanded into 12 countries. But this conversation isn't only about growth. We get into what it actually takes to build a cigar brand that retailers—and consumers—want to support. Don Emmanuel discusses his philosophy that a premium cigar should be an experience rather than simply a product, and why his blends are designed to evolve as you smoke them. We also get into the creation of Anunnaki, his first core line featuring seven different tobaccos, and the limited-edition Sun and Moon, which was introduced at PCA with only 777 boxes produced worldwide. We also discuss: - Don Emmanuel's journey from Brazil to the premium cigar industry - What a cigar sommelier actually does - Turning cigar education into a cigar business - Developing Don Emmanuel Cigars with Eladio Diaz and the Diaz Cabrera family - Why complexity and evolution are central to his blending philosophy - The story behind Anunnaki - Creating the limited-edition Sun and Moon - How a young cigar company breaks into U.S. retailers - Why supporting retailers after the sale matters - The danger of overcrowding humidors with too many SKUs - Why Don Emmanuel isn't interested in chasing every cigar trend - Social media's role in modern cigar education - What's next for the growing brand One of the most interesting parts of the conversation is Don Emmanuel's approach to retailers. Instead of viewing getting an initial order as the finish line, he argues that cigar companies need to become genuine partners—supporting stores with tastings, events, marketing and continued follow-through. Whether you're a cigar smoker, retailer, aspiring brand owner or simply interested in the business behind premium cigars, Episode 177 offers a look at what it takes to turn cigar knowledge and a big idea into a growing international brand. Subscribe to Deep Cuts Live for more conversations with cigar makers, entrepreneurs, blenders, brand owners and the people shaping the premium cigar industry. ============================================= Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates. ============================================= Website: deepcutslive.com YouTube: youtube.com/deepcutslive Instagram: instagram.com/deep_cuts_live

Who has been a guest on Deep Cuts Live

Names identified in recent episode analyses. Showing up to five guests.

• Enrique Sanchez
• Fouad Kashouty
• Romy Kashouty
• Rob Maneson
• Les Mann

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

3.7 / 5

3 ratings

Podcast Authority Score: 32 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

51

Social presence

0

YouTube

0

Engagement

31

Contact Deep Cuts Live

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

Questions about Deep Cuts Live