Island Jim Robbins Episode 16 Origin Series

Episode Summary

In this Origin Series installment of A Cigar Hustler's Podcast, Mike is joined by his brother Greg (filling in for Mikey, who is doing an event at Jim's own shop in Pittsburgh) to interview Island Jim Robinson of Leaf by Oscar / Island Jim Cigars. Jim explains that before tobacco he spent roughly 15–18 years managing Marriott hotels, then "retired," moved to Pittsburgh and opened the Leaf & Bean cigar shop because he didn't want to work — which turned into one of the busiest brand-building stories in the boutique business.

Jim details how he met Oscar Valladares, who previously worked for Rocky Patel giving factory tours, and asked him to make a house cigar for his store. That cigar became the Leaf by Oscar, made in Honduras, originally called "Leaf & Bean by Oscar" after the shop. The signature tobacco-leaf wrapping came from Oscar, inspired by a Mayan mummy discovered holding a cigar wrapped in a tobacco leaf. After turning down roughly 50 wholesale requests from tourists' home shops, Jim finally said yes — and today the company runs 10 reps, is in about 2,000 shops, and produces roughly 1.5 million cigars a year across Leaf by Oscar, Island Jim, Big Johnny and Woodies. He also shares the true origin of the 8x66 Big Johnny, named for a parking-lot attendant across from his store who smoked five big cigars a day, and reveals that the "Island Jim" persona and cartoon-face artwork came from Eddie Ortega, who cast him as March in the Ortega Wild Bunch series.

The trio smokes the Nick & Jim PBE, a collaboration with Nick Sears of LH Cigars (and the Smooth Draws radio program), rolled at Nick's Costa Rican factory — with an Ecuadorian Habano wrapper, Nicaraguan binder, and Peruvian and Nicaraguan filler, and no Costa Rican tobacco at all. Originally to be named La Vida Isla until a trademark conflict, it launched around Christmas. Jim also talks about the frequent customer mishap of trying to smoke the Leaf's outer tobacco wrapping, meeting his girlfriend and store manager Melody on Match.com, and his road-trip habits (using the Cigar Aficionado "Where to Smoke" app and never announcing his stops in advance).

The episode closes with the show's standard rapid-fire questions — Mickey Mouse as his fictional smoking partner, John Wayne as the one person living or dead, his father's advice to "buy the best so you don't have to buy it again," and a refusal to name a favorite cigar — plus his upcoming plans: Naples, a tarpon fishing tournament in Islamorada with Ron from Serious Cigars (Robert Holt of Southern Draw also attending), Key West, then the long drive home to Pittsburgh.

In This Episode

1. 01
   From Marriott Hotels to a Pittsburgh Cigar Shop
   Jim recounts 15–18 years managing Marriott hotels before retiring to Pittsburgh and opening the Leaf & Bean.
2. 02
   Meeting Oscar Valladares
   How a former Rocky Patel factory tour guide became Jim's blender and made his house cigar in Honduras.
3. 03
   The Leaf by Oscar Origin Story
   The Mayan mummy inspiration behind wrapping a cigar in a tobacco leaf, and why 'Leaf & Bean by Oscar' became just 'Leaf.'
4. 04
   Accidental Wholesaler
   Turning down about 50 wholesale calls before building to 10 reps, 2,000 shops and roughly 1.5 million cigars a year.
5. 05
   How 'Island Jim' Was Born
   Eddie Ortega's Wild Bunch series gave Jim his nickname, his March slot and the cartoon likeness now on the box and band.
6. 06
   Big Johnny and the 8x66 Mold
   The parking-lot attendant who smoked five big cigars a day and inspired the largest mold in the factory.
7. 07
   Smoking the Nick & Jim PBE
   The Costa Rica–made collaboration with Nick Sears of LH Cigars, its Ecuadorian Habano/Peruvian/Nicaraguan blend, and the La Vida Isla trademark snag.
8. 08
   Rapid-Fire Questions and Road Plans
   John Wayne, his dad's best advice, and a run from Naples to an Islamorada tarpon tournament and Key West before driving back to Pittsburgh.

Brands & Cigars Discussed

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Transcript

Every day I'm hustling, hustling, hustling, hustling, hustling, hustling, hustling, hustling, hustling, hustling, hustling. Every day I'm hustling, every day I'm hustling, every day I'm hustling, every day I'm hustling, every day I'm hustling, every day I'm hustling, every day I'm hustling, every day I'm hustling, every day I'm hustling. Welcome to a Cigar Hustlers Podcast, where we take a closer look at the people of the cigar industry, with your host, Mike and Mike. Hustlin', hustlin', hustlin', hustlin', hustlin', hustlin', hustlin', every day 'em', every day 'em', every day 'em', oh, love.

Welcome to a Cigar Hustlers Podcast. We're doing things a little different this week. Mikey is on the road doing events. So sitting in for him, we have his brother, Greg.

Greg, say hello. Hello, everyone. Okay, we do this whole thing when we start. We sort of say the name of the show in unison.

Okay. Okay, so we're going to give it a try. What was the name of the show again? Cigar Hustlers Podcast.

Got it, okay. Okay, you ready? One, two, three. Welcome to a Cigar Hustlers Podcast.

This podcast. Yeah, well, that's okay. We give it a shot. This week, sitting in with us, we have Island Jim Robinson.

Say hello, Jim. Hello. Wahoo. Wahoo.

He's here. He is coming in to do an event at the shop tonight, and this is part of our origin series, so we want to know how you got into the cigar business, what you did before you did cigars. Before I did cigars, I managed Marriott Hotels for about 15, 18 years, something like that. Quite a while.

Retired from that business, moved to Pittsburgh, opened a cigar shop because I didn't want to work. That's the shop I think Mikey's doing an event at tonight. He's actually at my store right now. He's at your store right now.

That's right. He's sort of flip-flop. Well, hopefully, we'll do better here than Mikey will do. Oh, that's the plan.

That's definitely the plan. Exactly. So, how did you get into cigars then, Jim? I mean, you had the shop, but when did you decide to start making your own cigar?

About six, seven years ago, I hooked up with Oscar Valladares. Oscar used to work for Rocky Patel, and he used to do all the tours for Rocky. When you go to the Rocky factory, if he was your host, it would show you around. When he left Rocky, I asked him to make me a cigar, and the first cigar we made was the Leaf by Oscar, and that was my house cigar.

Based out of Honduras, correct? Honduras, Stanley. Right. Very cool.

So then it just started taking off, and people decided they wanted it in their shops also? Yeah, I had it in my store for probably about two years. I was getting calls from, you know, people, I'm in a touristy location in Pittsburgh from my shop. " So we start wholesaling it, hired my first rep, covered quite a big territory.

Then I hired another rep, another rep, and now we've got 10 reps on the road selling it, and we're in about 2,000 shops. That's great. Where did the Island Jim persona come out? That was Eddie Ortega.

You can thank Eddie for that. Eddie did his Wild Bunch series about five, six years ago. I don't know if you remember the Wild Bunch. I do.

Can you explain what The Wild Bunch is for the people that haven't heard about that? Yeah, and he did a program, he had 12 different characters, one character per month for the year, sort of like a calendar pin-up thing. And I was month three, I was March, and he came to me and asked me if he could use my character, and I said sure, and he nicknamed me Island Jim. And then social media picked up on it, and the rest is history.

So did you dress like this when you were running Marriott's? No. No? No.

Well, certain ones I could get away with it. Right. Like Key West. Now, most of them I had to wear a suit and tie and no beard.

Yeah, for those of you that don't know, Island Jim has another cigar, Island Jim, and there is a large cartoon character of his face on the box as well as the band, and it looks just like him, without a doubt. It is entertaining to say the least. Thanks, Greg. You're welcome.

You have the notes, so give me that. About how many cigars do you put out a year? Probably a million and a half, between the Leaf by Oscars and the Island Gyms and the Big Johnny and the Woodies, and then Oscar has his own line too. All your cigars sort of have a little story, I know I've heard the Big Johnny story before, if you want to tell that.

The Big Johnny story? Across the street from my shop in Pittsburgh is a parking lot, and there's a big guy named Johnny who works the parking lot, he's actually short, but he's sort of bigger around, and his name is John, he works the parking lot, He smokes five big cigars a day. He used to come in and buy, I won't say the brand, because they're going to blame me for him cutting into their sales, but he would come in and buy five of these big cigars every day, and I told him, next time I go to my factory, I'm going to make you a cigar. And the biggest mold we had in the factory was an 8x66, so that's the size of the Big Johnny.

And I brought those back and named them after him, and again, it was just for him at first. Yeah, just something for you to give to him. Somebody put it on social media, seen it, and then people started asking me if they could get it. Isn't that amazing how things take off anymore?

But it was never planned to be part of the series, but... Just like Leaf by Oscar was, you know, just something that he made for you. Yeah, where'd you come up with that idea, to package the cigar inside the leaf? That was actually Oscar's idea.

Oscar's seen a Mayan mummy that they dug up, I don't know how many, hundreds of years ago, that was like 5,000 years old. And in this mummy's hand, he was holding a cigar that looked like it was wrapped in a tobacco leaf. Oh really? So that's where the original idea came from.

Now my story that I like to tell is that we got drunk and we just came up with the idea, but really it was Oscar's idea. So it could have been named the Mayan Mummy cigar. It could have been a mummy. Wouldn't have gone as well.

And the reason it got named the Leaf is because the name of my store is Leaf & Bean. So when I first came out with it, it was Leaf & Bean by Oscar. It was after my shop. But then when I started wholesaling, I figured people didn't want my store name on it, so we dropped the bean part and just called it Leaf.

Nice. Very good. How many times have you seen somebody try to smoke the wrapper of that cigar? That cigar.

Well, I try to tell them when I see them, but I hear a lot of stories that people do smoke it. " Yes. It's like smoking with the cellophane on. Yep.

Yeah, I've allowed somebody to actually do it and then give them assistance and remove it halfway through, and the cigar obviously is much, much better. I've seen people take the leaf and smoke it separately. That's a new one. Like in a pipe or something.

Yeah, probably mixed with something else. I would imagine. So what is this cigar we're all smoking here today? That is my Nick and Jim PBE.

That is one that is made in Costa Rica. Nick Sears, who has the LH brand of cigars, he's also on another radio program, Smooth Draws. Give them a little plug. That's made in his factory in Costa Rica, and it's a collaboration between the two of us.

It was originally going to be called La Vida Isla, but we ran into a trademark issue with the name, so we already had the cigars made. Instead of waiting for another name to pop up, we just called it Nick and Jim PBE. It sort of did a factory type look to it. And does it have Costa Rican tobacco in it?

Nope, no Costa Rican tobacco. Okay. It's Ecuador Habano wrapper, it's got Peruvian filler, Nicaragua filler, and Nicaragua binder. Pretty good.

It's got a very oily finish to it. It's very good so far. Agreed. It's becoming very popular for us.

When did you launch it again? At Christmas time. Okay. Between Christmas and New Year's.

So it's still pretty new. I went straight to the first year, but somebody jumped the gun. I was out of town. So who's running your shop right now?

Mike. Mike as in my brother? Well, you're in trouble, that's for sure. You're in a lot of trouble.

No, Melody, who is actually my girlfriend and my store manager, she watches the shop when I'm away. Yes, I've met her a few times. Very, very nice lady. How'd the two of you meet?

com. Really? Yep. That's awesome.

That's very cool. Many, many years ago. I invited her over for pizza and she never left. That's good, that's very good.

com, but he's fighting it tooth and nails. We have a little game that we're trying to get where everybody gets to pick him a date and then the winner wins the pool. Yeah, we're actually going to put a pool together for it, it'll work out well. And then if I actually wind up sticking with the woman that I've set up...

You have to marry her. I get to keep the pool, right? But you have to marry her, though, to get the woman's. That'll be my money?

It'll be your money. That'll be a great way to tell her how you met. I win you in a bet, honey. That's it.

So where are you going from here, Jim? Where's your next stop? Well, I got a fishing tournament to go to down in Isla Morada, or Isla Morada? What is it?

Isla Morada, I think it's. It depends on, yeah, sort of like Caribbean and Caribbean. But with Ron from Sirius Cigars, he does a fishing tournament down there, tarpon fishing. So that's my next stop.

No kidding, I didn't know he was in town. I think Robert Holt from Southern Draw is going down for that, too. Yeah, he was just here last week. Did you drive down?

Yeah. I thought I saw your video. Yes, his jeeps have got the same logo on it as the cigars do. I told my wife, I go, see this guy right here?

He's sitting inside, wait, just wait and see. Looks just like this. Just like the cartoon. Yeah, I like to drive, get off on the back roads.

Have you made any stops along the way? Just in St. Augustine. That's the only place I stop.

All right, cool. Very good. We have a series of questions that we ask everybody who comes on the show. Okay.

And then, let's see, the first question. What fictional character would you like to share a cigar with? Fictional character. Fictional character.

I can't even think of a fictional character. Could be anything. Could be anything. Somebody from a TV show.

Somebody from a movie. A book. TV show. Cartoon character.

Could be anybody. Anybody. Mickey Mouse. I don't know.

Excellent answer. Excellent answer. Okay. And then what one person living or dead would you like to share a cigar with?

John Wayne. That one was quick. That was quick. He was ready for that one.

That one he was ready for. All right. All right. What's the best piece of advice anyone ever gave you?

Best advice anybody ever gave me? Well, probably my, the one thing I remember is my dad always told me, if you're going to buy something, and my dad never had a lot of money, but he always believed if you buy something, buy the best so you don't have to buy it again. So. Excellent.

Very good. Okay. What's your favorite cigar? I love them all.

We're not letting you have to hook that easy. Yeah, you're not going to get me on that one, because I don't plug any one cigar, because I like them all, and I really do, I smoke all cigars. All right. All right, so what were you smoking in your car as you were on your way down?

I was smoking the Nick and Jim PB. Okay. Well, that's one of them. I was smoking others, but that's the one.

All right. All right, and you want to tell people how to get a hold of you, your social medias or emails? Do you have any emails? Yeah, I don't really have a whole list of stuff like that.

The easiest way is my Facebook, and it's under Jim Robinson, but it's got the Island Jim logo. Robinson. Robinson, R-O-B-I-N-S-O-N. Yeah, if somebody manages Twitter and all that, I don't even know what they are.

Hey, such a big deal. Well, okay, I guess that's it, unless you've got anything to add, Greg. So you're going to be going down to fishing. When are you heading down to Isla Morata?

I'll be heading, well, I'm going to stop in Naples on the way, visit a couple places in Naples, and I'll be heading to Isla Morata on Monday. So I'm going to go to Naples tomorrow, and Monday go to Isla Morata. And how long down in Isla Morata? I'll be there until Saturday, and then a couple days in Key West, and then driving back towards Pittsburgh.

It's a pretty good tour. It's a long drive, Key West to Pittsburgh. Yeah, it really is. It's a lot of alone time, I like that.

Are you going to be stopping at any other shops as you go more South Florida? Yeah, but I don't know which ones right now, because I don't know which path I'm taking. Gotcha. I use my little Cigar Fishiano app.

Oh, where to smoke. Yeah, where to smoke, and what I see along the way. Just pull in somewhere. Yeah.

Excellent. And I don't like telling them that I'm coming, because that way if I decide to go a different way, I'm... No commitment. No commitment at all.

No commitment. That's great. Very wise. You're the only commitment I made the whole way down.

Well, we appreciate it. Yes, thank you very much. Thank you very much. Well, thank you for coming in.

All right, folks, this one's a little short, but it was one of a spur of the moment. We appreciate everybody for listening, and that's it. All right, folks, that's it. Show's over.

If you like what we're doing, please tell your friends about us. Leave feedback. We always like to hear if you like the show or not, or if you have any suggestions for guests that we might possibly bring on at a later date. You can find us on our Facebook page at A Cigar Hustlers Podcast, or you can follow us on Instagram at Cigar Hustlers Podcast.

Thanks for listening, but get the fuck back to work. The End.

Show Notes

This week Mr Wahoo himself Island Jim Robbins stopped by to have a chat with us.  Mikey was on the road promoting his own cigars so his Brother Gregg (the other half of Cigar Hustler) joined me for a quick interview.

Find out about Jims beginnings in the Hotel business that lead him to his own Cigar shop and the Cigar Brand that became a lifestyle!

We would appreciate your comments and suggestion on our FB page "A Cigar Hustlers Podcast".  You can follow us on IG @cigarhustlerspodcast or find Mikey @cigarhustler and Mike @floridacigarclub_mike.

Thanks for listening!