There’s something timeless about lighting up a cigar. It’s not just about smoking. It’s about slowing down, connecting with people, and appreciating the craftsmanship that goes into every single roll. In today’s episode, we explore the culture, history, and proper etiquette of cigars with someone who lives and breathes it every day.

My good friend Paolo Pergola joins us for a backyard session filled with rich conversation and even richer cigars. Paolo has built an incredible career in the cigar industry as a distributor, and he’s one of the most knowledgeable people I know when it comes to the art of cigars.

Our friendship goes back to my high school hockey days, and to this day, he’s like family to me. Having him on the show was not just fun, it was an education.

We open up a box of cigars and talk about everything from how to properly cut and light one to what beginners often get wrong.

Paolo shares personal stories from inside the cigar business, including how he built relationships with top cigar brands, what makes a cigar truly premium, and how different regions like Cuba, Nicaragua, and the Dominican Republic influence flavour profiles.

In this episode, we dive into:

• The step-by-step ritual of preparing and smoking a cigar

• How cigars are made and the craftsmanship behind the wrapper, filler, and binder

• The difference between hand-rolled and machine-made cigars

• How to choose the right cigar for your experience level

• The impact of climate and soil on the tobacco leaves

• The rise of cigar lounges and the sense of community they bring

• Why cigar smoking is more about conversation than consumption

• Misconceptions around cigars and health

• What to avoid as a first-time smoker

• How cigars are priced and what makes some worth thousands

Whether you're a cigar aficionado or someone who’s always been curious, this episode has something for you. We kept it real, relaxed, and informative all from the comfort of my backyard with a few good sticks in hand.

If you are in the Greater Toronto Area and looking to buy quality cigars or want to learn more about the cigar lifestyle, Paolo is your guy. You can contact him here: 416--671-7667 | [email protected]

Also, if you’re thinking about buying or selling real estate, feel free to reach out to me directly at [email protected] or connect with me on Instagram @davidvcinelli_realtor.

Let us know in the comments what you thought of the episode. Should we have more conversations like this? More cigar content? More backyard hangs? Your feedback means a lot.

Thanks for watching, and we’ll see you on the next one.