Deep Cuts Live

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.

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Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates.

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• Website: deepcutslive.com
• YouTube: youtube.com/deepcutslive
• Instagram: instagram.com/deep_cuts_live

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.

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Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates.

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• Website: deepcutslive.com
• YouTube: youtube.com/deepcutslive
• Instagram: instagram.com/deep_cuts_live

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.

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Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates.

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• Website: deepcutslive.com
• YouTube: youtube.com/deepcutslive
• Instagram: instagram.com/deep_cuts_live

Camacho Cigars has been producing bold, distinctive blends for decades—but brand ambassador Law Ream believes even longtime cigar smokers may be surprised by what they discover when they revisit the brand.

In episode 176 of Deep Cuts Live, host Antoine Reid sits down with Law to discuss his unconventional journey from running a marketing firm and creating cigar media to working inside Davidoff and representing Camacho Cigars.

Law explains how Camacho is building stronger relationships with today’s cigar smokers through education, experiential events and digital media. He also challenges some common perceptions about the Camacho portfolio—including why the Triple Maduro may not be as intimidating as its reputation suggests and why the Camacho Ecuador deserves more attention.

The conversation also explores:

• How Law transitioned from cigar media to brand marketing

• What separates Camacho from Davidoff, AVO and Zino

• Why younger cigar smokers approach brands differently

• How Camacho creates educational experiences for consumers

• The truth about developing your palate and identifying tasting notes

• What makes the Camacho Triple Maduro surprisingly approachable

• Why the Camacho Ecuador may be the brand’s most underrated cigar

• The Camp Camacho factory-tour experience

• How podcasts, YouTube and social media are changing cigar marketing

Whether you already enjoy Camacho Cigars or have not smoked one in years, this conversation may convince you to give the brand another look. Follow Law Ream on Instagram: @boldleaflaw

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Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates.

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• Website: deepcutslive.com
• YouTube: youtube.com/deepcutslive
• Instagram: instagram.com/deep_cuts_live

Mexican San Andrés tobacco appears in some of the most recognizable premium cigars in the world—but how much do cigar smokers really know about where it comes from?

For Episode 175 of Deep Cuts Live, host Antoine Reid sits down with Gerardo Turrent of Tabacalera Turrent, part of a family whose roots in Mexican tobacco stretch back to 1880. Today, Tabacalera Turrent grows tobacco in Mexico’s San Andrés Valley and produces brands including Te-Amo and Casa Turrent.

The conversation explores Mexican tobacco from the perspective of someone who grew up surrounded by it: the importance of the San Andrés region, what makes Mexican tobacco distinctive, and what it means to carry a family business and tobacco tradition into another generation.

Gerardo and Antoine also discuss the perception of Mexican cigars, the work that happens long before a finished cigar reaches a humidor, and why understanding the tobacco itself can change the way you experience the cigar in your hand.

If you’re interested in Mexican cigars, San Andrés tobacco, cigar making, tobacco farming, Casa Turrent, Te-Amo, or the families behind premium cigars, Episode 175 offers a deeper look at a part of the cigar world that deserves more attention. Subscribe to Deep Cuts Live for long-form conversations with cigar makers, brand owners, blenders and the people shaping the premium cigar industry.

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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

How do you build one of the strongest brands in premium cigars without chasing every trend?

In Episode 174 of Deep Cuts Live, host Antoine Reid welcomes Terence Reilly of Aganorsa Leaf for his first appearance on the show in six years. Together, they look back at one of the most transformative periods in the company's history—from a major rebrand and explosive growth to memorable cigar releases, marketing breakthroughs, and the lessons learned along the way.

Terence explains how Aganorsa Leaf evolved into one of the industry's most recognizable brands by focusing on authentic storytelling, consistent messaging, and the unique character of its Nicaraguan tobacco rather than simply chasing the latest trends.

In this episode, we discuss:

* The evolution of Aganorsa Leaf over the past six years

* The rebranding strategy that changed the company's identity

* Why storytelling is one of the most powerful marketing tools in premium cigars

* Building long-term relationships with retailers and consumers

* The impact of COVID on cigar marketing and brand recognition

* Behind-the-scenes stories from Supreme Leaf, Rare Leaf, Arsenio, and Anniversario Connecticut

* Why Aganorsa doesn't chase every industry trend

* The company's Select Partner retailer program

* The importance of factory tours and cigar education

* Common misconceptions about Nicaraguan tobacco

* Why Terence believes cigar smokers should trust their own palate—not ratings

The conversation also explores consumer psychology, premium cigar branding, social media, tobacco education, and what it takes to build lasting loyalty in today's cigar market.

Whether you're an Aganorsa fan, a retailer, or simply interested in the business behind premium cigars, this episode is packed with insights from one of the industry's most thoughtful voices. Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry.

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Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates.

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• Website: deepcutslive.com
• YouTube: youtube.com/deepcutslive
• Instagram: instagram.com/deep_cuts_live

What happens when two tobacconists decide to build a premium cigar brand around authenticity instead of tradition?

In Episode 173 of Deep Cuts Live, host Antoine Reid welcomes Brandon Oveson and Kendrick Woolstenhulme, co-founders of Apostate Cigars, for a conversation about storytelling, cigar blending, and creating one of the industry's most distinctive boutique brands.

Rather than following the traditional path of family tobacco farms or generations in the cigar business, Brandon and Kendrick built Apostate around their own story—drawing inspiration from their experiences growing up in Utah, their shared love of premium cigars, and a willingness to challenge convention.

In this episode, they discuss:

* How a friendship at a Utah cigar shop became Apostate Cigars

* The origin of the Apostate name and the brand's unique identity

* Why storytelling matters as much as the cigar itself

* Working with Tabacalera Palma and master cigar maker Jochy Blanco

* Their blending philosophy and creative process

* Why relationships still drive success in the premium cigar industry

* The partnership with Oveja Negra Brands

* The stories behind Death Mask, Lost Pages, Deseret and Feathered Serpent

* Why their Candela became one of their best-selling cigars

* Their vision for sustainable growth and the future of Apostate

The conversation also explores boutique cigars, retailer relationships, factory culture, and why Brandon and Kendrick believe the journey of building a cigar company is just as important as the destination.

Whether you're discovering Apostate for the first time or you've been following the brand from the beginning, this episode offers an honest look at creativity, craftsmanship, and building something different in today's premium cigar industry. Subscribe to Deep Cuts Live for more conversations with the people shaping premium cigars.

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Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates.

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Website: deepcutslive.com
YouTube: youtube.com/deepcutslive
Instagram: instagram.com/deep_cuts_live

What does it take to keep one of the most iconic names in premium cigars relevant while honoring its legacy?

In Episode 172 of Deep Cuts Live, host Antoine Reid welcomes back Sean Williams, Cohiba's brand ambassador and master blender, for a wide-ranging conversation about luxury, innovation, and the evolving premium cigar industry. More than five years after his first appearance on the show, Sean reflects on how both he and the industry have changed—and why time, relationships, and experiences matter more than ever.

From the philosophy behind Cohiba's luxury positioning to the stories behind releases like Riviera, Rubicon, Spectre, Serie M, and the Weller collaboration, Sean offers an inside look at the creative process that brings some of the industry's most anticipated cigars to life. He also discusses cigar blending, building memorable brand experiences, the rise of cigar bars, and why authentic relationships remain the foundation of long-term success.

In this episode, you'll hear about:
* How Cohiba continues to evolve while honoring its heritage
* The inspiration behind Riviera, Rubicon, Spectre, Serie M, and Weller
* What luxury really means in today's premium cigar market
* The art and science of blending premium cigars
* Why relationships still matter more than social media
* The growth of cigar bars and changing consumer habits
* Advice for boutique cigar companies trying to stand out
* Sean's personal philosophy on time, purpose, and leaving a lasting legacy

Whether you're a longtime Cohiba smoker, a cigar retailer, or simply fascinated by the business behind premium cigars, this conversation offers thoughtful insight into one of the industry's most recognizable brands—and the man helping shape its future.

Subscribe to Deep Cuts Live for more conversations with the people behind the premium cigar industry.

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Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates.

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Website: deepcutslive.com
YouTube: youtube.com/deepcutslive
Instagram: instagram.com/deep_cuts_live

Episode 171 of Deep Cuts Live features Nicholas Perdomo III for an in-depth conversation about family, craftsmanship, and carrying one of the premium cigar industry's most recognizable names into the future.

Host Antoine Reid sits down with Nicholas at Perdomo's factory in Nicaragua to discuss what it's like growing up in a family business, learning directly from Nick Perdomo Jr., and preparing to lead a company built on three decades of relationships, quality, and consistency.

In this episode, Nicholas discusses:
* Growing up inside Perdomo Cigars
* Why relationships remain the foundation of the cigar business
* The upcoming Perdomo Challenge sampler and consumer tasting initiative
* The story behind Perdomo Legacy: Father & Son
* Developing new cigar blends and packaging
* Why Perdomo releases fewer cigars than many competitors
* Launching the Perdomo Podcast and educating consumers
* The importance of family in shaping the Perdomo brand
* What today's younger cigar smokers are looking for
* His vision for the future of Perdomo Cigars

The conversation also explores factory expansion in Nicaragua, consumer engagement, social media, cigar education, and why Nicholas believes the next generation of cigar smokers wants more than just a great cigar—they want to know the people behind the brand.

Whether you're a longtime Perdomo fan, a retailer, or someone interested in the business of premium cigars, Episode 171 offers a thoughtful look at what it means to protect a family legacy while continuing to innovate.

Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry.

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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

Season 6 of Deep Cuts Live continues with episode 170, featuring special guest Garrison Davis, Brand Ambassador for AVO Cigars. This is a conversation about legacy, innovation, and one of the most significant moments in the brand's nearly 40-year history.

Host Antoine Reid sits down with Garrison to discuss his unlikely path from banking and finance into the premium cigar industry, what it means to represent one of the world's most respected cigar companies, and how AVO is introducing a new generation of smokers to its music-inspired heritage.

In this episode, Garrison discusses:
* His journey from finance to becoming an AVO Brand Ambassador
* The remarkable story of Avo Uvezian and the origins of AVO Cigars
* Why music has always been at the heart of the AVO brand
* How Davidoff has evolved AVO while honoring its founder's legacy
* The launch of the new AVO Expresivo
* Why AVO produced its first-ever Honduran-made core line cigar
* Pairing premium cigars with cocktails and creating memorable experiences
* What younger cigar smokers are looking for today
* Retail merchandising strategies that help premium cigars stand out
* The future direction of AVO Cigars

The conversation also explores how premium cigar brands must balance tradition with innovation, why storytelling matters more than ever, and what it takes to introduce a legacy brand to a new generation of consumers.

Whether you're an AVO fan, a Davidoff enthusiast, retailer, or simply interested in the business behind premium cigars, Episode 170 offers a behind-the-scenes look at one of the industry's most respected brands—and where it's headed next.

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Subscribe to Deep Cuts Live for more conversations with the people shaping the premium cigar industry. Visit deepcutslive.com for more episodes and updates.

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Website: deepcutslive.com
YouTube: youtube.com/deepcutslive
Instagram: instagram.com/deep_cuts_live