- I'm ready to rock, and

we're rolling, by the way,

just so you know.

- Perfect.

- In case you say something untoward.

- Like fuck?

(interviewer laughing)

(bright music)

- Very similar to fuck,

yes, that would be accurate.

So, Robert [Caldwell], good to

see you. (crowd chattering)

- Likewise, you might,

- Yeah.

- Do I need to extend this a little?

- You can, yeah, you're doing good.

How's it sound in here?

- I like to sit in a

leisurely way, so.

- Yeah, you're leisurely.

- Thank you.

- You're leisurely.

I love seeing you at shows.

- Likewise.

- Yeah, it's a treat.

Yeah, you're a fine human being.

- Thank you.

- Yeah,

and what's new?

- We sold the company.

- Hello?

- You didn't know that?

- I didn't know that.

- For real?

- When did you do that?

- Three weeks ago.

- Well, you know, three,

I'm a little behind

on the news.

- Yeah.

- Three weeks ago, tell me the story.

- So, we started speaking

(passersby laughing)

with a company that's in the pipe industry

about doing a licensed, like,

licensure of our artwork

for them for some tobacco,

and then we just kept

talking about various things,

and then they ended up

kind of inquiring if we'd

be interested to sell,

and I liked them very

much, and so, it was-

- That's the trick, because

there's, you don't like

- A lot of people.

- No,

(interviewer laughing)

but I like that they have

like, everything that we don't.

- Yeah?

- And then I have

equity in the company,

so, I'm staying on, and I

think it's gonna simplify.

It's kinda like new partners, I guess,

is the way to look at it.

- But that's a good idea,

because you are the face

of, well, obviously,

Caldwell Cigars, you're Caldwell,

but you've done such a personal

job of reaching people,

- Yeah.

- And introducing them

to all these tastes, all these flavors

that you've brought to the marketplace.

It's really cool.

You've done a hell of a job.

- Thank you.

- Yeah.

- So, that's what's new.

- You sold the company?

- Yeah.

- Congratulations.

- Thank you.

You didn't notice my booth

was not as dirty as usual?

- No, I noticed that

you didn't have, like,

two milk crates and a 2x10.

- Exactly.

- Yeah, you were actually in a booth.

- Yeah.

- And those are the folks-

- So, they, yeah, so, they had like,

four booths for themselves,

and then they added two more,

and then those became our-

- Just for old time sake, do

you still sit on the floor

once in a while to stay

connected to your roots?

- I would've, but they

rented us furniture.

(interviewer laughing)

- Padded carpeting?

- No.

- Okay.

- They're still intelligent.

- No, that's good, it's good to have some-

- The padding, the padding.

- It's a luxury.

- You know, we did that our

first year, it was like

1,100 bucks for a tiny booth,

and the next year, we just

bought everybody, like,

brand new New Balances,

and that became, yeah.

- Oh, that's good.

- And then it switched to on.

- So, this is a great, little

caveat into your personality.

"The first year, we paid

$1,100 for the booth.

The next year, we bought

everybody tennis shoes."

- Yes, and it was like, 600 bucks.

- I love that you saved

- A lot of money, yeah.

- A lot of money.

A lot of money.

I'm super happy for you.

How's your beautiful bride?

- Thank you, she's good.

- Yeah?

- She's in Madrid.

I'll see her in two weeks.

- Nice.

You're headed there?

- Yeah, I go back to

Miami, then I go to...

So, this week, I go

back to Miami tomorrow,

the next day, I go to Texas for an event,

then I go back to Miami the next day,

and then I go to Dominican

Republic for a few days,

and then from there to Spain.

- This is lovely, by the way.

- Thank you.

- I haven't got it lit

properly, but it's lovely.

It's got a nice start to it.

Tell me about the cigar I'm smoking.

- So, that's the

prototype of the Long Live

The Queen Maduro,

which is probably gonna sell very well,

because Queens are our

top performing brand in

the last year.

(coughs) Excuse me, so,

it has a Brazilian, like,

hybrid Arapiraca wrapper,

dark wrapper, Maduro,

Sumatra binder, and then

fillers are all aged Dominican.

It'll be a bit darker than

that, because we're doing...

That was the samples that

we made for the show.

We rolled them, like, four months ago,

but then the finished

production has one additional

fermentation on the wrapper,

which makes it darker,

a little bit more rich,

and a little bit creamier,

so, it'll look better and

taste a little bit more smooth.

- Now, in the new

iteration of your company,

do you get to keep your crew,

the people that have been part of your

team for years?

- So, Juan, who was one

of my business partners,

came over as well,

and then one of my sales guys direct,

I only had two in-house sales

guys, the rest were brokers,

so, one of them came, one of them didn't,

and then the office guys were let go, so.

- So, the new, the next

evolution of Caldwell Cigars,

you're gonna continue calling it

Caldwell Cigars?

- Yeah.

Yeah, I'm not sure what

their grand plan is.

I imagine they'll try to

institutionalize the brand,

which they should, over the next years,

and make it maybe a little bit

less Robert Caldwell-centric,

because I do think that there's

a little bit of risk there.

When it's my company and I run it,

and it's me, me, me all the

time, I think that's very easy,

but for another company

to have ownership of that,

if something were to happen to me,

and I could no longer do what I do,

then I think you have a liability.

So, I think that for

them, it would make sense

to institutionalize

the brand a little bit,

and take it a little bit away

from, like, Robert Caldwell.

- We had a really interesting

conversation with Litto Gomez,

of La Flor Dominicana, and his son, Tony.

He sat in that chair,

and it resonated with me,

and it actually reminded me of you,

because I think you said

something like this to me

right after I met you, which

was at this show years ago.

He [Litto] said, "In the

face of whatever adversity

that comes up,

I really only have one resort,

and that is to look at myself and say,

'I need to work harder,'

and not jealous about

somebody else's success,

not blaming anybody else for

circumstances, conditions."

We had this conversation,

and you've been that way.

That's been your ethic

from the get go.

- Yep.

- It's fantastic, and it's

fun to see it, you know,

it's almost a reverse reflection.

He's been at it longer than you,

and has had a pretty storied

career with La Flor Dominicana,

but hardscrabble guy,

started from scratch,

you know, went out there

and made it happen.

- Yeah.

- It's the same thing

that you did with this,

and did you go out and learn

all this stuff on your own?

- Yep.

- Self-taught cigar,

everything?

- All of it.

Business, everything, so,

no formal education in any of it.

- Beautiful.

What a great story.

- Yeah, thank you.

- And you've been a

great friend of Boveda.

- You guys as well to us.

- Yeah.

Well, I tell you, I

got deep into your line

at Cigar Jones in Minnetonka.

they have a bunch of

facings of Caldwell cigars,

and started with the Blind Man's Bluff.

- Yep.

- Two of those got into, you

know, the American Standard,

The Long Live The King, The King Is Dead.

I mean, how many different...

- Brands do we have?

I think, like, nine or something?

I'm not exactly sure.

- Are they all made in the same place?

- Majority of them are made

at Tabacalera William Ventura,

and then we have probably about 60%

of our production's there,

and then we have a couple

other manufacturers

that we work with.

Sometimes regularly, sometimes

for one-offs or limiteds,

we'll do stuff with other factories,

but most of it's William Ventura,

and then we do some in

Honduras, and then Nicaragua.

We've worked with AJ

Fernandez and also Oliva,

but the mainstay's Ventura in D.R.

- This is gonna be a hit.

This is a lovely cigar.

- Yeah, very good, huh?

- Yeah.

Yeah, and are you still

hands on with everything?

- Yeah.

- You go to the factory,

you see the people, you

spend time with the rollers,

the whole deal?

- Yeah, I mean, nothing really changes,

except stress levels and layers

of responsibility.

- Oh, so, you're gonna be

more relaxed now?

- Yeah.

(interviewer laughing)

Which kind of is, like, hard to imagine,

because I'm a pretty laid back guy,

but I do get stressed out,

or I have in the past.

- Well, you're an intense guy.

- I'm intense, yeah.

- In a polite way.

Yeah, I think that's a

good characterization.

- But, so, now, I have, you know,

you go from being an

owner-operated business to a not,

and then I can focus on what I do best,

and then not have the stress

of somewhere in my head,

did we ship this?

Or when is this import coming?

All that stuff's off my radar.

I'm completely unaware of these

things, which is very nice,

because they have a team

that deals with import,

a team that does marketing,

these types of things,

so, it allows me to just

focus on the big picture

of, I think, what I enjoy,

which is also what I do best.

- So, okay, drill down

a little bit on that

before we wrap this up.

I want to really sort of dwell

on what it is you do best.

What is your sweet spot?

- Product development.

So, cigars, I make good cigars,

I think a very good palate.

If you like my cigars, at least you think

I have a very good palate?

- I think you have a very good palate.

- Thank you, and then the packaging,

so, all the branding,

these types of things,

boxes and design.

- So, design, and the look,

and the feel, and the-

- And then the marketing, I do very well,

or at least I do-

- Really, what don't you

do well?

Do you do social posts?

Is that part of your-

- My wife does that.

- Okay.

- I won't do it.

I'm morally opposed to social media,

so, I have nothing

(interviewer laughing)

to do with it,

but, so, my wife does all the social,

which they're gonna start

doing that in-house now.

I'm a bad manager, like,

a real bad manager.

I don't know if I'm a

great operator, either.

- Boy, this is really working out.

- Yeah, it's exactly the...

I'm living what I hoped I would do

when I was in my twenties.

- How beautiful is that?

- Yeah, it's very weird,

because I actually said in my twenties,

"I want to be here, here,

here at this point in life,

and I wanna live between, like,

my three favorite countries,

which are Spain, Colombia, and Italy,"

and it's all falling into place.

- Good, did you have a good show?

- I think so.

I never pay attention ever.

- Well, because you're a shitty manager.

- Yeah, but if we have a good show,

a bad show, it doesn't matter.

If you have a bad show,

it means you sell more

the next three months.

- Right.

- If you have a good show,

it means you sell less

the next three months.

- Yeah, you just sold everything.

- Yeah, you're just pulling forward sales.

So, years that we had the best shows

were either when we had hot new releases,

or when we were doing good deals.

The years that we made the most

money were our worst shows,

where we had no discounts,

or we had weaker sales,

but then you sell more at

full price 60 days later, so.

- Yeah, your cigars are wearing

well with people.

(lips smacking)

Hey, that's our next guest [Nicholas

Melillo, Foundation Cigar Company].

- What's up, bro?

- Sorry, I had to give you

- That's our next guest, yes.

- A kiss.

- I didn't know if that

was you.

- It was getting weird.

- I didn't know if it was you

- He's warming your seat.

- Or Miguel [Schoedel,Crowned

Heads Cigars]. - We're done.

- No, no, no, no,

- Because both of you,

both of you,

- Yeah, no, no, no.

- Your mugs feel the same.

- How are we?

- I'm good.

- Starting next.

- Here, here, here, you're up.

- No, no, no, you sit.

- We're done, we're done.

(bright music)