I'd rather set my head on fire. But that's just me.
I hope it works out great for you, whatever way you decide to go. :-)
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Just my 2 cents... if its your dream and your passion... go for it.. don't let anybody tell you different.
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its not easy...a lot of red tape if you want to smoke indoors...depending on your state. If you want liquor in there as well, then its a **** storm. States arent really excited to hear of a cigar bar coming up...at least thats how it is here on the east coast.
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Some quick hits about B&M

1) what does the state law say about smoking establishments? What are the requirements to be able to have a retail shop and lounge?

IE, in Illinois, any new cigar shop needs to be in a stand alone building, especially if you are offering a smoking lounge.

2) what licenses are needed? BYO license? Tobacco? hookah?

3) other avenues of income...vapor? gentleman's products? lockers? memberships?

4) community outreach: sell your cigars or at least sell pro-shops inventory; any bar that allows patio smoking will might want to have a humidor; high end steak houses might have a humidor; any wine/ale/beer/scotch/whiskey fest will want a vendor selling cigars there; Harley-Davidson events; sell at golf outings for any non-profits....don't just donate a gift...go out and sell and donate % of proceeds.

5) reach out to vendors and have events with vendors

6) multiple sources of cigar for your stock...I just don't rely on direct vendor relationships.

7) don't spend much on print advertisement; word of mouth is where its at; location is where its at..especially lots of foot traffic

8) make sure you have parking!!!!
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Right now, I'm trying to figure out exactly what the current laws in NYC are. I've found this:

Clean Indoor Air Act (CIAA)
Enacted in 1989 and last amended in 2013, the Clean Indoor Air Act (CIAA) prohibits smoking of tobacco (herbal cigarettes are exempted) in nearly all public and work places. Exemptions are allowed for cigar bars in existence prior to December 31, 2002 and for organizations that do not have employees.

I haven't yet found any info covering cigar shops which are not bars, but early indicators point to no smoking in new cigar shops. If that's true, my little project is probably dead in the water. I mean, I guess some folks manage to run shops in which smoking is prohibited, but I just don't see how I could compete with the heavy hitters online if I couldn't offer a comfortable smoking lounge. Unless, I was mainly a newsstand or something else. A lot of newsstands around here sell a few cigars. But, thing is, I don't want to run a newsstand.

I surely wouldn't be able to offer competitive pricing. In the state of New York, tax on cigars is 75% of wholesale value. I don't know wholesale cigar prices, and I'm a bartender not a mathematician, but I've heard it said this means a $20.00 cigar in NY retails for $27.50. If I expect a guy to pay my prices rather than shop online, I'd better be able to offer him something he can't get from the big-box stores. And if he can't smoke in my shop, well...

I will of course report back here if I discover that I'm wrong about new shops being unable to permit smoking.

You know, should I decide to pursue this thing much further, this is a great idea. Hell, if I don't pursue this thing much further this is a great idea. :-)

Thank you, everyone, for all your thoughtful responses.
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The no money part, means probably not a good idea. Especially starting out, you can fail rather quickly in the first year or two.
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Someone told me I should start out selling cigars on consignment. Doubt there is a huge profit margin there, but it is intriguing in a low overhead and low risk sort of way.
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IF I was opening a cigar shop, it would be a men's shop. I'd sell cigars and pipe tobacco, pipes, lighters, etc. Then, I'd have a full line of shaving supplies: Razors, replacement blades, soaps, aftershave, etc. An electric razor would be banned and requests for them would result in the requestant being assaulted and battered by a short, fat man with a vowel at the end of his last name.
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I agree with flaming head. I also agree with the others that you have to be more than a cigar shop. The Net can supply cigars cheaper than you can so you have to have some much more that can't be ordered via a debit card.
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I think the point is, you probably want to have additional things to attract people and sell to them. It might be worth pointing out that JR's huge stores in N Carolina have a lot more floor space devoted to clothes, perfume, pots and pans than they do to cigars.
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Follow your dream and go for it! One of my favorite places here on Siesta Key is Leilu's, a coffee shop that has a beer & wine license. They allow smoking outside, but not indoors due to food service. Personally, if I had a cigar shop, I'd copy that place, delete the food and have it be cigar friendly. Kick azz coffees, expresso, limited beers and wines. They offer live music twice weekly and prices are reasonable. Best is the customer service is superb. Doesn't hurt that it's a block off the beach and there is always a steady stream of perky eye-candy strutting by! :-)
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There are three shops right near my house and all of them do fairly well.

First is Spec's, which is really wine/beer/liquor mega store. Their humidor is pretty good sized but mostly carries the "standard" brands (Fuente, Perdomo, RP etc.) However, they're the only shop in the area that stocks Liga Privada, both #9 and T52. They've also got the best prices on the standard stock. There are a few downsides though. First, there's really only two guys who work there who know anything about cigars and the humidor tends to be a bit messy just from the amount of traffic that wandesr in and out. Since it's a chain store there's NEVER any sales on the cigars. Also, since it's really a liquor store there's no lounge or anywhere to enjoy your new purchases at. But, it is convenient being able to grab a smoke or two then walk 50ft over to the bourbons and scotches.

Next is Cigar Depot. It's the smallest of the shops, just a hole in the wall in an older strip mall. The humi isn't anything special and has a kind of cold, surgical room feel to it. Decent selection and the prices aren't too bad. Gary, the owner, is the only one I've ever seen working there and he's a fountain of knowledge when it comes to cigars. The "lounge" is just a couple of easy chairs right by the front door. This place really only sells cigars. There's a small selection of cigs and some tins of pipe tobacco, but cigars are the main focus here.

Lastly, there's Pipe World. This is my favorite shop of the three and I tend to visit here about once a week even though Spec's is less than 2 miles from my front door. Good sized humidor that is packed from floor to ceiling. Awesome selection of sticks and it's constantly rotating. No Liga Privada, but lots of boutique and small batch brands in addition to the standard stock. If there's a new release or new brand coming out, chances are Pipe World will have it in stock shortly after. Also the only shop that hosts events and giveaways. Prices tend to be a bit higher, but the sales here are great. They'll toss whole boxes of smokes into the clearance baskets and mark them 30-40% off, in addition to the 10% a membership gives. There are several employees in addition to the owners and they're all very knowledgeable about the products they sell. The owners are also very open to suggestions on new lines to carry. The lounge isn't great, but it works. Just some easy chairs stuffed into an alcove by the register. Pipe World is also the sort of catch all shop that the others here are suggesting. They sell cigars, knives, cigs, e-cigs, hookahs, nick-knacks like wind chimes and, of course, pipes. Lots and lots of pipes. This place is always busy and the events get pretty crowded.

Anyway, I typed all that not to brag about what I have available to me but to give you three different, and rather distinct, styles of shop you could look into. Granted, none of them serve alcohol except for Pipe World, but they don't sell any alcohol just give out bottles of beer or glasses of whiskey during their events.
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An option to getting around the no indoor smoking issue...

Picture a storefront that has an apartment on top. These typically exist in older 'downtown streets'...

Here's where it becomes clever and pricey. You purchase both the store and the apartment above it. Usually these sell as a complete unit.

Your cigar shop is opened on the main floor. You create the lounge in the apartment, which you own as "your personal residence". You just so happen to allow your "friends" to go into your personal residence to smoke. BYOB of course. No licenses needed, and separate entrance. Obviously, this option would only be open to a customer who purchases a cigar from your shop and would like to smoke it indoors in comfort.

You would not advertise this additional space to just anyone...it would be discretely known to your regular, loyal customers. I've just shared my dream with you.

Boom!
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Damn that could be a million dollar idea.
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I guess I don't get this, though this sentiment has been brought up before on other threads. I picture a Wal-Mart shaving isle with a walk in humidore.
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Search for the wetshaving thread. Or check out sharpologist.com
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I have to say, how would that not work?

I mean, I'm sure it would find a way to blowup in my face and I'd lose all I'd worked for, BUT...

How would that not work?
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^^^ this

Well spoken - you should not jump in eyes closed - business plan is required.

You should do up a year budget and see what costs along with your bottom line to make sure it is feasible - demographics play an important role - are you going to sell online or not? What will be your obstacles eyc. sWOT analysis should be done as well.

At the end of the day - it wil be your final judgement, but having this all completed will give yourself direction on where you want to be and how to get there.

I would strongly suggest the idea of getting into the field before trying it yourself so you can see what the markups and what you can do better than your soon to be competitors.
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On thing I forgot too. If you decide to do it. Before you make any moves, lawyer up. Get a good business law attorney to advise you and get you set up in a way that will best insulate you personally from the business failing. If you aren't careful to start with and as you operate, you can expose you and your family to tremendous financial liability. Just be smart, the extra cost up front is worth it!
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Unless you incorporate (at least in canada) that's how you protect yourself- but for what He is wanting to do, it will not be worth incorporating - coastwise.

Get yourself a bank loan / loc and have a good business plan, along with some starting capital.

Besides what bank is going to provide a loc to a new incorporated company without something up front

Anyone who tells you differently or to jump on it without a gameplan and or backup plan is being foolish.
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