Episode 129
Why I Sold My Company | Robert Caldwell | Caldwell Cigar Co. | Box Press Ep. 129
Long Live the King! Learn how to preserve cigars with Boveda, click here to get emails: https://hubs.la/Q01BLsBF0
After running Caldwell Cigar Co., for a decade, Robert Caldwell and co-founder, Juan Jaramillo sold the company to Laudisi Enterprises. How will your favorite Caldwell cigars, like Blind Man's Bluff and Anastasia be affected? Find out directly from Robert himself.
By acquiring the boutique cigar brand, Laudisi is branching out from the premium pipes and pipe tobacco arenas. Catch the whole story with Boveda's Drew Emmer at PCA 2024, the preeminent event for premium cigar and pipe industry.
00:00 This is Box Press
00:33 Caldwell Cigar founders sell their cigar company
03:14 Smoking the Caldwell Long Live The Queen Maduro
04:34 How do you go from being an owner-operated business to not?
07:46 Is Robert Caldwell still running Caldwell cigars?
08:56 What's you sweet spot?
10:40 Video bomb by Nicholas Melillo, Foundation Cigar Co.
What is Boveda? Boutique cigars like Caldwells protect blends with Boveda 2-way humidity control—that brown pack that you find in the box with your cigars. Boveda preserves the flavor and character of premium cigars by keeping them at ideal humidity. At home, continue to use Boveda in your humidor to keep cigars well-humidified or they can be hard to light, burn to too fast or get moldy. With Boveda in your humidor, you'll enjoy full flavor and a perfect smoke from every cigar.
Facebook: https://www.facebook.com/bovedausa/
X (Twitter): https://twitter.com/BovedaInc
Instagram: https://www.instagram.com/bovedainc/?..
Transcript
- I'm ready to rock, and
we're rolling, by the way,
Speaker:just so you know.
- Perfect.
Speaker:- In case you say something untoward.
Speaker:- Like fuck?
Speaker:(interviewer laughing)
(bright music)
Speaker:- Very similar to fuck,
yes, that would be accurate.
Speaker:So, Robert [Caldwell], good to
Speaker:see you. (crowd chattering)
Speaker:- Likewise, you might,
- Yeah.
Speaker:- Do I need to extend this a little?
Speaker:- You can, yeah, you're doing good.
Speaker:How's it sound in here?
- I like to sit in a
Speaker:leisurely way, so.
Speaker:- Yeah, you're leisurely.
Speaker:- Thank you.
- You're leisurely.
Speaker:I love seeing you at shows.
Speaker:- Likewise.
- Yeah, it's a treat.
Speaker:Yeah, you're a fine human being.
Speaker:- Thank you.
- Yeah,
Speaker:and what's new?
Speaker:- We sold the company.
Speaker:- Hello?
Speaker:- You didn't know that?
Speaker:- I didn't know that.
- For real?
Speaker:- When did you do that?
- Three weeks ago.
Speaker:- Well, you know, three,
I'm a little behind
Speaker:on the news.
- Yeah.
Speaker:- Three weeks ago, tell me the story.
Speaker:- So, we started speaking
(passersby laughing)
Speaker:with a company that's in the pipe industry
Speaker:about doing a licensed, like,
Speaker:licensure of our artwork
for them for some tobacco,
Speaker:and then we just kept
talking about various things,
Speaker:and then they ended up
Speaker:kind of inquiring if we'd
be interested to sell,
Speaker:and I liked them very
much, and so, it was-
Speaker:- That's the trick, because
there's, you don't like
Speaker:- A lot of people.
- No,
Speaker:(interviewer laughing)
but I like that they have
Speaker:like, everything that we don't.
Speaker:- Yeah?
- And then I have
Speaker:equity in the company,
Speaker:so, I'm staying on, and I
think it's gonna simplify.
Speaker:It's kinda like new partners, I guess,
Speaker:is the way to look at it.
- But that's a good idea,
Speaker:because you are the face
of, well, obviously,
Speaker:Caldwell Cigars, you're Caldwell,
Speaker:but you've done such a personal
job of reaching people,
Speaker:- Yeah.
- And introducing them
Speaker:to all these tastes, all these flavors
Speaker:that you've brought to the marketplace.
Speaker:It's really cool.
Speaker:You've done a hell of a job.
Speaker:- Thank you.
- Yeah.
Speaker:- So, that's what's new.
Speaker:- You sold the company?
Speaker:- Yeah.
Speaker:- Congratulations.
- Thank you.
Speaker:You didn't notice my booth
was not as dirty as usual?
Speaker:- No, I noticed that
you didn't have, like,
Speaker:two milk crates and a 2x10.
Speaker:- Exactly.
Speaker:- Yeah, you were actually in a booth.
Speaker:- Yeah.
- And those are the folks-
Speaker:- So, they, yeah, so, they had like,
Speaker:four booths for themselves,
and then they added two more,
Speaker:and then those became our-
Speaker:- Just for old time sake, do
you still sit on the floor
Speaker:once in a while to stay
connected to your roots?
Speaker:- I would've, but they
rented us furniture.
Speaker:(interviewer laughing)
Speaker:- Padded carpeting?
Speaker:- No.
Speaker:- Okay.
Speaker:- They're still intelligent.
Speaker:- No, that's good, it's good to have some-
Speaker:- The padding, the padding.
Speaker:- It's a luxury.
- You know, we did that our
Speaker:first year, it was like
1,100 bucks for a tiny booth,
Speaker:and the next year, we just
bought everybody, like,
Speaker:brand new New Balances,
Speaker:and that became, yeah.
- Oh, that's good.
Speaker:- And then it switched to on.
Speaker:- So, this is a great, little
caveat into your personality.
Speaker:"The first year, we paid
$1,100 for the booth.
Speaker:The next year, we bought
everybody tennis shoes."
Speaker:- Yes, and it was like, 600 bucks.
Speaker:- I love that you saved
Speaker:- A lot of money, yeah.
- A lot of money.
Speaker:A lot of money.
Speaker:I'm super happy for you.
Speaker:How's your beautiful bride?
Speaker:- Thank you, she's good.
Speaker:- Yeah?
- She's in Madrid.
Speaker:I'll see her in two weeks.
- Nice.
Speaker:You're headed there?
Speaker:- Yeah, I go back to
Miami, then I go to...
Speaker:So, this week, I go
back to Miami tomorrow,
Speaker:the next day, I go to Texas for an event,
Speaker:then I go back to Miami the next day,
Speaker:and then I go to Dominican
Republic for a few days,
Speaker:and then from there to Spain.
Speaker:- This is lovely, by the way.
Speaker:- Thank you.
- I haven't got it lit
Speaker:properly, but it's lovely.
Speaker:It's got a nice start to it.
Speaker:Tell me about the cigar I'm smoking.
Speaker:- So, that's the
prototype of the Long Live
Speaker:The Queen Maduro,
Speaker:which is probably gonna sell very well,
Speaker:because Queens are our
top performing brand in
Speaker:the last year.
Speaker:(coughs) Excuse me, so,
it has a Brazilian, like,
Speaker:hybrid Arapiraca wrapper,
dark wrapper, Maduro,
Speaker:Sumatra binder, and then
fillers are all aged Dominican.
Speaker:It'll be a bit darker than
that, because we're doing...
Speaker:That was the samples that
we made for the show.
Speaker:We rolled them, like, four months ago,
Speaker:but then the finished
production has one additional
Speaker:fermentation on the wrapper,
Speaker:which makes it darker,
a little bit more rich,
Speaker:and a little bit creamier,
Speaker:so, it'll look better and
taste a little bit more smooth.
Speaker:- Now, in the new
iteration of your company,
Speaker:do you get to keep your crew,
Speaker:the people that have been part of your
Speaker:team for years?
- So, Juan, who was one
Speaker:of my business partners,
came over as well,
Speaker:and then one of my sales guys direct,
Speaker:I only had two in-house sales
guys, the rest were brokers,
Speaker:so, one of them came, one of them didn't,
Speaker:and then the office guys were let go, so.
Speaker:- So, the new, the next
evolution of Caldwell Cigars,
Speaker:you're gonna continue calling it
Speaker:Caldwell Cigars?
- Yeah.
Speaker:Yeah, I'm not sure what
their grand plan is.
Speaker:I imagine they'll try to
institutionalize the brand,
Speaker:which they should, over the next years,
Speaker:and make it maybe a little bit
less Robert Caldwell-centric,
Speaker:because I do think that there's
a little bit of risk there.
Speaker:When it's my company and I run it,
Speaker:and it's me, me, me all the
time, I think that's very easy,
Speaker:but for another company
to have ownership of that,
Speaker:if something were to happen to me,
Speaker:and I could no longer do what I do,
Speaker:then I think you have a liability.
Speaker:So, I think that for
them, it would make sense
Speaker:to institutionalize
the brand a little bit,
Speaker:and take it a little bit away
from, like, Robert Caldwell.
Speaker:- We had a really interesting
conversation with Litto Gomez,
Speaker:of La Flor Dominicana, and his son, Tony.
Speaker:He sat in that chair,
and it resonated with me,
Speaker:and it actually reminded me of you,
Speaker:because I think you said
something like this to me
Speaker:right after I met you, which
was at this show years ago.
Speaker:He [Litto] said, "In the
face of whatever adversity
Speaker:that comes up,
Speaker:I really only have one resort,
Speaker:and that is to look at myself and say,
Speaker:'I need to work harder,'
Speaker:and not jealous about
somebody else's success,
Speaker:not blaming anybody else for
circumstances, conditions."
Speaker:We had this conversation,
and you've been that way.
Speaker:That's been your ethic
Speaker:from the get go.
- Yep.
Speaker:- It's fantastic, and it's
fun to see it, you know,
Speaker:it's almost a reverse reflection.
Speaker:He's been at it longer than you,
Speaker:and has had a pretty storied
career with La Flor Dominicana,
Speaker:but hardscrabble guy,
started from scratch,
Speaker:you know, went out there
and made it happen.
Speaker:- Yeah.
- It's the same thing
Speaker:that you did with this,
Speaker:and did you go out and learn
all this stuff on your own?
Speaker:- Yep.
- Self-taught cigar,
Speaker:everything?
- All of it.
Speaker:Business, everything, so,
Speaker:no formal education in any of it.
Speaker:- Beautiful.
Speaker:What a great story.
- Yeah, thank you.
Speaker:- And you've been a
great friend of Boveda.
Speaker:- You guys as well to us.
Speaker:- Yeah.
Speaker:Well, I tell you, I
got deep into your line
Speaker:at Cigar Jones in Minnetonka.
Speaker:they have a bunch of
facings of Caldwell cigars,
Speaker:and started with the Blind Man's Bluff.
Speaker:- Yep.
Speaker:- Two of those got into, you
know, the American Standard,
Speaker:The Long Live The King, The King Is Dead.
Speaker:I mean, how many different...
Speaker:- Brands do we have?
Speaker:I think, like, nine or something?
Speaker:I'm not exactly sure.
Speaker:- Are they all made in the same place?
Speaker:- Majority of them are made
at Tabacalera William Ventura,
Speaker:and then we have probably about 60%
Speaker:of our production's there,
Speaker:and then we have a couple
other manufacturers
Speaker:that we work with.
Speaker:Sometimes regularly, sometimes
for one-offs or limiteds,
Speaker:we'll do stuff with other factories,
Speaker:but most of it's William Ventura,
Speaker:and then we do some in
Honduras, and then Nicaragua.
Speaker:We've worked with AJ
Fernandez and also Oliva,
Speaker:but the mainstay's Ventura in D.R.
Speaker:- This is gonna be a hit.
Speaker:This is a lovely cigar.
- Yeah, very good, huh?
Speaker:- Yeah.
Speaker:Yeah, and are you still
hands on with everything?
Speaker:- Yeah.
- You go to the factory,
Speaker:you see the people, you
spend time with the rollers,
Speaker:the whole deal?
Speaker:- Yeah, I mean, nothing really changes,
Speaker:except stress levels and layers
Speaker:of responsibility.
- Oh, so, you're gonna be
Speaker:more relaxed now?
- Yeah.
Speaker:(interviewer laughing)
Speaker:Which kind of is, like, hard to imagine,
Speaker:because I'm a pretty laid back guy,
Speaker:but I do get stressed out,
or I have in the past.
Speaker:- Well, you're an intense guy.
Speaker:- I'm intense, yeah.
- In a polite way.
Speaker:Yeah, I think that's a
good characterization.
Speaker:- But, so, now, I have, you know,
Speaker:you go from being an
owner-operated business to a not,
Speaker:and then I can focus on what I do best,
Speaker:and then not have the stress
of somewhere in my head,
Speaker:did we ship this?
Speaker:Or when is this import coming?
Speaker:All that stuff's off my radar.
Speaker:I'm completely unaware of these
things, which is very nice,
Speaker:because they have a team
that deals with import,
Speaker:a team that does marketing,
these types of things,
Speaker:so, it allows me to just
focus on the big picture
Speaker:of, I think, what I enjoy,
which is also what I do best.
Speaker:- So, okay, drill down
a little bit on that
Speaker:before we wrap this up.
Speaker:I want to really sort of dwell
on what it is you do best.
Speaker:What is your sweet spot?
Speaker:- Product development.
Speaker:So, cigars, I make good cigars,
I think a very good palate.
Speaker:If you like my cigars, at least you think
Speaker:I have a very good palate?
Speaker:- I think you have a very good palate.
Speaker:- Thank you, and then the packaging,
Speaker:so, all the branding,
these types of things,
Speaker:boxes and design.
- So, design, and the look,
Speaker:and the feel, and the-
Speaker:- And then the marketing, I do very well,
Speaker:or at least I do-
- Really, what don't you
Speaker:do well?
Speaker:Do you do social posts?
Speaker:Is that part of your-
- My wife does that.
Speaker:- Okay.
Speaker:- I won't do it.
Speaker:I'm morally opposed to social media,
Speaker:so, I have nothing
(interviewer laughing)
Speaker:to do with it,
Speaker:but, so, my wife does all the social,
Speaker:which they're gonna start
doing that in-house now.
Speaker:I'm a bad manager, like,
a real bad manager.
Speaker:I don't know if I'm a
great operator, either.
Speaker:- Boy, this is really working out.
Speaker:- Yeah, it's exactly the...
Speaker:I'm living what I hoped I would do
Speaker:when I was in my twenties.
Speaker:- How beautiful is that?
- Yeah, it's very weird,
Speaker:because I actually said in my twenties,
Speaker:"I want to be here, here,
here at this point in life,
Speaker:and I wanna live between, like,
my three favorite countries,
Speaker:which are Spain, Colombia, and Italy,"
Speaker:and it's all falling into place.
Speaker:- Good, did you have a good show?
Speaker:- I think so.
Speaker:I never pay attention ever.
Speaker:- Well, because you're a shitty manager.
Speaker:- Yeah, but if we have a good show,
Speaker:a bad show, it doesn't matter.
Speaker:If you have a bad show,
it means you sell more
Speaker:the next three months.
Speaker:- Right.
- If you have a good show,
Speaker:it means you sell less
the next three months.
Speaker:- Yeah, you just sold everything.
Speaker:- Yeah, you're just pulling forward sales.
Speaker:So, years that we had the best shows
Speaker:were either when we had hot new releases,
Speaker:or when we were doing good deals.
Speaker:The years that we made the most
money were our worst shows,
Speaker:where we had no discounts,
or we had weaker sales,
Speaker:but then you sell more at
full price 60 days later, so.
Speaker:- Yeah, your cigars are wearing
Speaker:well with people.
(lips smacking)
Speaker:Hey, that's our next guest [Nicholas
Melillo, Foundation Cigar Company].
Speaker:- What's up, bro?
Speaker:- Sorry, I had to give you
- That's our next guest, yes.
Speaker:- A kiss.
- I didn't know if that
Speaker:was you.
- It was getting weird.
Speaker:- I didn't know if it was you
- He's warming your seat.
Speaker:- Or Miguel [Schoedel,Crowned
Heads Cigars]. - We're done.
Speaker:- No, no, no, no,
- Because both of you,
Speaker:both of you,
- Yeah, no, no, no.
Speaker:- Your mugs feel the same.
Speaker:- How are we?
Speaker:- I'm good.
- Starting next.
Speaker:- Here, here, here, you're up.
Speaker:- No, no, no, you sit.
- We're done, we're done.
Speaker:(bright music)
