Gadiel tells the story he's somehow never told in 62 episodes: how he became a co-owner of The Art of Cigar in San Diego. It started with Luis, a multi-generation Dominican master roller who was making beautiful cigars all day and owning none of them — so Gadiel asked what if the roller became the owner. Along the way: a haunted shop in Old Town, a trip to the Dominican Republic, a family recipe that ended up in one of the world's most famous cigars, a 60% tobacco tax, and an honest answer to whether he'd do it all again.
In this solo episode, Gadiel finally tells the story behind The Art of Cigar, the cigar lounge he co-owns in Old Town, San Diego. It began with wanting to invest in a business and not knowing what. What he did know was that he loved smoking a good cigar with his friends. On a trip to San Diego he met Luis, a roller who worked all day producing what Gadiel describes as masterpieces — people lined up to watch him and take pictures. But Luis didn't own any of it. Gadiel learned that's standard in the cigar world: rollers use recipes passed down through their own families and see almost none of the upside. His reaction was simple — what if the roller becomes the owner? Luis had been waiting for the right partners. They found a spot in Old Town, the oldest part of San Diego, where the rent was cheap and the neighbors swear the block is haunted (one shop owner showed Gadiel video of her shutters opening and closing on their own, with a cemetery across the street). Then they flew to the Dominican Republic to meet Luis's family and connects, including Tamboril — the country's cigar capital, where there are rollers everywhere but only a handful of true blenders. Luis made Gadiel a custom cigar he still calls the best he's ever smoked — chocolatey with cinnamon spice. It's no longer sold because it's too expensive to produce. Luis's blend comes from his great-grandfather, and the family protects it fiercely. Which makes the best story in the episode: as a kid, Luis handed a recipe to one of the biggest cigar brands in the world, and it became one of their most famous smokes. His father almost disowned him. Then Gadiel gets into the parts nobody warns you about. California taxes tobacco around 60%, which forces prices up. You legally cannot advertise a cigar business. A competing lounge opened across the street. A new per-SKU tax law pushed them to stop manufacturing in California and move production to the DR. The business is self-sustaining now, and his partners run the day-to-day so he can focus on comedy — but his advice is blunt: don't get into the cigar business. He closes with the lesson he'd give his younger self. Building from scratch means wearing every hat — hiring, marketing (which never stops), the POS system, the website, shipping, the books. If he could go back, he'd buy a business with at least a three-year track record: existing customers, existing staff, existing systems. No regrets, though. He loves the place, and he's grateful Luis trusted him. If you're in San Diego, stop by, say hi to Endy, and tell them the podcast sent you. Timestamps: 00:00 — Episode 62: the cigar lounge story I've never told 01:24 — Meeting Luis: the master roller who owned nothing he made 07:07 — The family recipe that went to a huge brand — and nearly cost him his father 09:37 — 60% tax, no advertising allowed: why this business almost broke us 13:21 — "Don't start a business — buy one" 🚬 The Art of Cigar — Old Town, San Diego. DM Gadiel if you go and he'll sort you out with a discount. 💬 Got a business question? Send it in and he'll answer it on the next episode.