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Island Jim and Oscar Valladares

Island Jim and Oscar Valladares

Travelling to Copan, Honduras with my long-time friend Oscar Valladares, we talked about everything, as people on the road together do. Oscar said he was at the point in his life where he wanted to make a change, from working for others to opening his own factory.

If you don’t know him, Oscar is a man of strong character, a good man. No, a great man. His commitment to work, his family, and his friends means he tackles life the right way—with passion and dedication.

“I want one of the first cigars made in your new factory to be for me” I told him. The “Leaf by Oscar” was born.

We discussed types of cigars, what I like, what I would like to see. We talked about flavor profiles and sizes. After several months and several more trips to the factory, we settled on three of our current blends—the “Leaf by Oscar” cigar.

During the process, I envisioned the Leaf by Oscar as the house cigar for my little retail shop in Pittsburgh’s Strip District. When Oscar, after months of working together, asked about my first order, I told him “5,000 for the year.” At the same time, I thought, Wow, that’s a big order. How am I possibly going to sell that many of one cigar in a year?

Oscar looked at me and I could practically see his thought, All this work for only 5,000 cigars?

With the first batch done, all 5,000 cigars made, I realized I had no idea how to get them to Pittsburgh.

I happened to have a group of ten in Honduras at the time. Each person could legally bring back 100 cigars. That made 1,000 cigars for my retail shop. That will last me a while, I figured. And give me enough time to get the other 4,000 to the US. I was pretty pleased.

One week after putting the 1,000 Leaf by Oscar cigars on my shop shelf, they were gone. All of them. Sold. In one week. I needed a crash course in importing. I needed a broker.

The remaining 4,000 cigars soon made their way to the Leaf and Bean and within one month, they were gone. All of them. Sold. In a month.

(Lesson learned during the process: Don’t hire a broker during a crash course. You may wind up with the most crooked broker in the business, like I did.)

For several months, the Leaf by Oscar sold only as a house cigar. Then other retailers started calling, wanting to sell the cigars in their own shops. I politely told the first ten callers I wasn’t interested, that the Leaf by Oscar was the house cigar. I didn’t tell them the real reason: I didn’t know anything about wholesaling.

With the 11th phone call, I figured I’d better learn.

And I did learn. You can now purchase the Leaf by Oscar, Island Jim, and soon Big Johnny cigars in over 300 retail locations across the US and in several other countries. Wahoo!


A hearty thanks to folks behind the scenes/ Acknowledgements

Island Jim & Bayron Duarte

Island Jim & Bayron Duarte

Contrary to popular belief, Island Jim cannot do everything himself. His Wahoo! is frequently possible thanks to the following people:

Without the help of other manufacturers, there would be no Leaf by Oscar, Island Jim, or Big Johnny cigars. They have given me invaluable inspiration and insight into the cigar world. A giant Wahoo! and an even greater Thank you!

Vendors who have helped me become successful as a retailer, which gave me the knowledge and confidence to make my own cigars.

The Leaf + Bean staff, who provide the most excellent customer service. Without them, our small shop wouldn’t be a success.

The people at Oscar’s factory who create our cigars. I am proud to be working with you and I can’t thank you enough for the consistently wonderful products I am proud to put my name on.

Without the distribution and sales staffs, we would never be able to share those amazing products with the outside world.

Island Jim