The Main Man: How Anthony Caliendo Built an Empire Through Sheer Determination

Meet Anthony Caliendo—the unstoppable force behind Florida's #1 business brokerage and the living embodiment of pure determination. In this riveting conversation, Anthony reveals how he transformed from a poor Chicago kid with no father figure into a serial entrepreneur whose relentless drive has conquered multiple industries.

Anthony's story isn't just inspiring—it's a masterclass in resilience. From washing dishes at 13 to managing prestigious health clubs at 18, he shares how harsh mentorship and public criticism became the forge that tempered his unbreakable spirit. "If you're not challenged by people above you, how are you going to become great?" he asks, describing how he channeled that pressure into extraordinary success.

You'll discover how Anthony built and rebuilt his life multiple times: dominating Wall Street despite failing the Series 7 exam twice, creating the iconic "Main Man" personal brand for his mortgage empire, turning around the "Big Cheese" food business with innovative marketing, and ultimately finding his calling as a business broker who helps owners successfully exit their companies. His candid insights about the crushing 2008 financial crisis reveal the mental fortitude required to start over when everything you've built crumbles.

What sets this episode apart is Anthony's raw honesty about business ownership. He explodes myths about selling businesses, revealing why 8 out of 10 businesses never sell and how owners sabotage their own exits without realizing it. For anyone who owns a business or dreams of entrepreneurship, his straight-talking advice about valuation, financial transparency, and preparing for eventual exit is absolutely invaluable.

Whether you're struggling to find your path or looking to elevate your success to new heights, Anthony's philosophy will resonate: "The only person that gets in the way of you is you." Listen now to absorb the wisdom of someone who's been knocked down countless times but always gets back up—like a "weeble wobble" that refuses to stay down.

Learn more at:
https://twinteriors.com/podcast/

https://scottwoolley.com

Chapters

• 0:00 Meet Anthony Caliendo, The Main Man
• 8:56 Childhood Hustle and First Jobs
• 18:30 Learning from Tough Mentors
• 27:04 Wall Street and Trading Career
• 37:52 The Birth of "The Main Man"
• 43:32 Selling Businesses and Market Challenges
• 1:07:56 From Author to Movie Producer
• 1:16:28 Closing Thoughts and Key Takeaways

Transcript

Voice Over: 0:00

This is iDesign Lab, a podcast where creativity and curiosity meet style and design. Curator of interiors, furnishings and lifestyles. Hosted by Tiffany Woolley, an interior designer and a style enthusiast, along with her serial entrepreneur husband Scott, idesign Lab is your ultimate design podcast where we explore the rich and vibrant world of design and its constant evolution in style and trends. Idesign Lab provides industry insight, discussing the latest trends, styles and everything in between to better help you style your life, through advice from trendsetters, designers, influencers, innovators, fabricators and manufacturers, as well as personal stories that inspire, motivate and excite. And join us on this elevated, informative and lively journey into the world of all things design. Today, on the iDesign Lab, we're joined by Anthony Caliendo, entrepreneur, international best-selling author, motivational speaker, chef and the powerhouse behind Florida's number one business brokerage. From dominating Wall Street to producing hit films and launching his own food empire, the main man does it all with unmatched drive and charisma. Get ready to be inspired.

Tiffany Woolley: 1:13

Welcome to the iDesignLab podcast. Today we have Anthony Caliendo in our house here, who is the main man who has designed quite a life.

Anthony Caliendo: 1:25

Yes.

Tiffany Woolley: 1:26

An entrepreneurial life at that. So tell us the main man.

Anthony Caliendo: 1:31

I'm going to give you the story of the main man, tell us a little about yourself. We'll give you kind of what led up to the main man also.

Scott Woolley: 1:37

Okay, because you have trucks, vehicles you have like a lot. I'm a branding guy. You are At the end of the day.

Tiffany Woolley: 1:44

I say this in one of my books called the Sales.

Anthony Caliendo: 1:46

Assassin that I wrote. It was my first book that I wrote and if you're not remembered, you're forgotten, right, and that's the problem with most people that you need to be remembered. You know, and when people remember you, you know you can contact them five years, ten years down the road, and they don't forget you. So how do you get people not to forget?

Tiffany Woolley: 2:05

you To be unforgettable.

Anthony Caliendo: 2:06

Unforgettable. I'm an unforgettable guy. So as a kid always had a dream of being successful, grew up with a mother who raised three kids and we were poor. We didn't have much money. Where did you grow up so in Chicago and then moved down to Florida, believe it or not, when I was 12. And my mom transferred down to Florida and she met a nice Jewish guy named Don Beagle. He's still today the only Jewish guy I ever met that couldn't make money, that's a funny joke, but it's true, right.

Anthony Caliendo: 2:39

You know. So you know, having a childhood where you have a bad deck of cards, right you? Know, sometimes people don't get lucky Like my wife and my kids, who we have eight kids. They're in a different position. I was in a position where I had to go out there and change my stars.

Voice Over: 3:00

I love that.

Anthony Caliendo: 3:00

So the only way to change your stars is to figure out roughly what you need to do. So my grandfather as a kid and I'm kind of going back a little bit so you understand my mentality Sure Right, because with every person there's something inside of them that triggers them, that makes them move, that makes them go, that makes them tick that moment, right yeah.

Anthony Caliendo: 3:20

So, as a kid, my grandfather said to me he said, anthony, your father's not around, your mother's raising three kids. You know what are you doing? I said I'm 12 years old, I'm in school. He said what are you going to school for? I says what do you mean? You go to school when you're my age. Yeah, he goes. Listen to me, you're a man in a house even though you're 12, you know, we're an old school Italian family. You need to go get jobs, you need to help your mother. And I'm like, okay, he's got a point. So I said well, why do you say that? He goes nothing against teachers? They do an amazing job. They teach children that they sacrifice. But the only thing a teacher is really going to teach you is how to be broke. And I said what?

Voice Over: 4:01

do you mean?

Anthony Caliendo: 4:02

He says nothing against teachers. I don't want to get the wrong thing here. You know in your head because they're amazing people, teachers but they're not going to show you how to become very successful and to make a lot of money and they're in a position where they're probably never going to make a lot of money. But that's the life they chose.

Tiffany Woolley: 4:19

Correct. So the question is what?

Anthony Caliendo: 4:21

life. Do you want to choose? Where do you want to go with your life? And I said I want it all. I don't want to be that person who's mad, didn't have a father around that grew up with a single mother, use that as your superpower. I didn't want to be that kid, so being when I was younger, you know, of course I had ADD, adhd, I think I had it all, don't all?

Tiffany Woolley: 4:43

most of us, you name it, I had it all and I feel like successful people do have that, but they didn't label you back then.

Anthony Caliendo: 4:48

Correct, I wasn't labeled as a kid. Yeah, okay. So even though I was edgy, I was always didn't want to sit, still Busy, I was always busy. I didn't want to go to that to me about that I said.

Scott Woolley: 5:06

You know, maybe he's got a point, so I come home.

Voice Over: 5:08

I go mom, I'm quitting school, and she says quitting school. What do you mean? You're quitting?

Anthony Caliendo: 5:10

school I said grandpa told me that I'm gonna be broke if I listen to the teacher basically, and I need to work to help you, or to at least help the family, or or figure out how to how to contribute, right? She says, well, that's not gonna happen, you're not quitting school, right? So I went to school and then I realized at eighth grade, all the way up to your senior year not now, they don't do this, but I was what? 13, maybe 12 or 13. They allowed you to get out of school at 1030 to have a work experience in the work program.

Anthony Caliendo: 5:40

So I'm like, well, this is great, I don't want to sit in school. Anyways, I'm probably never going to use most of this crap they're teaching me Totally. So I'll go out and I'll get jobs. So I went home and I said Mom, how about this compromise? She says, you know, as long as you graduate high school unlike your father and unlike myself okay, because my parents didn't graduate high school you know, my mother had three kids when she was 19.

Tiffany Woolley: 6:04

So young probably, yeah, 19 years old.

Anthony Caliendo: 6:05

So I said I'm going to graduate high school, but I'm going to go to work experience. So at 12 or 13, I had three jobs. So what were your first job or two? So I was always hustling as a kid. So it started when I was probably eight or nine. I mean, you're talking to a guy who was going to the golf course you know selling lemonade and golf balls.

Anthony Caliendo: 6:26

I used to swim in the lakes at nine, 10 years old. I swim in the lakes, grab all the golf balls, put them in egg cartons and then go to the golf course and sell them. Okay, and then it got a little aggressive, you know, because my parents were still married at the time. They didn't separate till I was like 10. So one day at the golf course my dad's like listen, why don't you go to the golf course and sell beer? You know, I said you could do that, you know.

Anthony Caliendo: 6:50

so of course I didn't know, I was like 10 years old, so I got my golf balls, my lemonade and a cooler of beer and next thing, you know, the golf security came and said you can't sell beer and my dad made a joke out of it like it was funny, right, you know, but I did it right. So as far as kind of my career, and where is it going and how did it start, it all started as a child and trying to figure out how to outwork everybody. I wasn't the smartest tool in the shed. I graduated high school, I didn't go to college, but I knew my drive and my passion and my dedication and you know it was relentless, it was nonstop.

Scott Woolley: 7:30

You know from. So. But did you want to be a boss? Did you want to just work to make money? Did you have any ambition of where you wanted to go? I love selling.

Anthony Caliendo: 7:38

I mean I used to sell waterless, greaseless cookware door to door at 16 years old Okay, greaseless cookware door-to-door at 16 years old, okay, wow. So as a kid I always said you know what can I do? I mean working three jobs. I mean I started in washing dishes Five days a week. I worked at I'll never forget, it was here in Hollywood the Vineyards Italian Restaurant. Unbelievable Some people that grew up in that Miramar Hollywood area remember that.

Anthony Caliendo: 8:01

You remember it, I washed dishes five days a week there, and then on the weekends, I washed dishes at the epicurean restaurant, which was breakfast and lunch.

Anthony Caliendo: 8:09

Some people remember the epic yes I remember, you know, yeah and then I worked at alouette liquor store friday and saturday night stocking, stocking the shelves. So you know, as a kid I was hustling right from grabbing my lawnmower on my bike and pulling it behind me and knocking on doors to cut lawns. I mean, you name it, I hustled. Nobody out-hustled me. Well, you knew how to take your energy and channel it into something, and that's why I never really went to I guess you could say the dark side.

Tiffany Woolley: 8:38

Right.

Anthony Caliendo: 8:38

And what I mean by that is when you grow up in a rough area, you grow up around people that are doing drugs and crime and everything else. You could wind up seeing yourself in a bad position.

Tiffany Woolley: 8:50

I would think pretty quick.

Scott Woolley: 8:51

But you were too busy for any of that.

Anthony Caliendo: 8:53

That's what kept me strong, because I occupied my time with work because I love to put the time and the effort into the work and my work ethic was insane. But I love to have the money on me, right, okay, you know when you don't have any effort into the work and my work ethic was insane, but I love to have the money on me, right, okay, you know when you don't have any money on you, when you're going to school and the kids are making fun of you because you're wearing bobos.

Anthony Caliendo: 9:11

Do you remember that? No the gym shoes, the blue ones with the three stripes. They were called bobos they basically you'd get them from the the blue light in Kmart, where they'd have the little blue light, you know thing, in a bin with Bobo's shoes. So they even made a song with it and they used to sing it to me as a kid, so I didn't want to sing the song because I'm such a horrible singer. But, people that are listeners that grew up in the 80s. They know what Bobo's are.

Scott Woolley: 9:38

So at what point was it where your career started to shape? Because you're a best-selling author, you're selling businesses, you've produced a movie, started a movie.

Tiffany Woolley: 9:51

You're diversified.

Scott Woolley: 9:52

You've written a couple of books.

Voice Over: 9:54

You're educating and teaching people.

Scott Woolley: 9:58

I mean you've got a cooking show, so at what point was it that kind of your life and your direction, kind of?

Anthony Caliendo: 10:06

started to form when I got past that high school education and realized that I wanted more.

Tiffany Woolley: 10:13

You were free a little bit too.

Anthony Caliendo: 10:14

You know, I actually started in the health club business okay, right, and I moved back to Chicago and tried to basically have a relationship with my father, and that didn't work. He wound up, unfortunately going to prison. Have a relationship with my father, and that didn't work. He wound up unfortunately going to prison for a long time and I was on my own. Now, now I'm in Chicago and I'm on my own, so I'm working in the health club business selling gym memberships at 18 years old.

Tiffany Woolley: 10:38

You know, I hear so many people because I love podcasts, which is how I started this, but I feel like so many sales entrepreneurs started selling gym memberships.

Anthony Caliendo: 10:48

It's crazy. In the 80s it was huge. I mean I would sell a membership for Chicago Health Clubs At the time we had 26 gyms in Chicago and I would sign you up for 36 months on a contract which was financed by another company. So you would finance a membership for three years at like $60 a month and get free tanning, unlimited racquetball, and we would sit there and we would basically have you sign these contracts for three years Now $10 a month and you can cancel when you want.

Tiffany Woolley: 11:18

I don't even understand how they stay open. To be honest, it's so true. Different model.

Anthony Caliendo: 11:23

But the health club business molded me because I worked 12 hours, 13 hours, 14 hours a day. They put me in a rough gym to start and then, you know, I started just beating everybody in sales. I just crushed everybody. I was a young kid. So one of the top managers supervisors said you know, I'm going to give you an opportunity to manage a gym. He goes you're just amazing, I'm going to give you a gym, but it's in the worst area of Chicago.

Tiffany Woolley: 11:54

And I said thank you very much.

Anthony Caliendo: 11:56

He goes you're going to go to Evergreen Park. I went Evergreen Park. Evergreen Park in Chicago is close to the jail and all of the gangs, every gang you can imagine in Chicago, goes to that gym.

Anthony Caliendo: 12:11

So I'm like so you're going to put me in a gym that's the worst gym in Chicago and I said you know what I'll take the challenge. That was what molded me to what I am today. It was that challenge at an early age that they gave me the worst possible gym you could imagine, and I wound up going there and I turned that gym completely around. I got everybody on my side and I wound up remodeling the whole gym.

Tiffany Woolley: 12:39

Wow, they loved me. So did you have a partnership in this, or mainly just I was?

Anthony Caliendo: 12:44

working for a company as a W-2 employee and as a sales rep and I was given an opportunity and it was a horrible, horrible opportunity, but it was an opportunity. So if I can prove myself what was going to happen next, yep, so that's kind of where it led. I wound up at 19 buying my first house okay, at 19 years old In Chicago or here In Chicago Right over the border in Indiana Okay.

Tiffany Woolley: 13:08

It's a little cheaper.

Anthony Caliendo: 13:08

Okay, I remember I bought a $72,000 house at 19 years old, you know so. Then I bought a limo for shits and giggles and had fun with my friends, and then I boat, you know. So I wound up making money and I wound up, you know it was funny because I had a spending issue.

Tiffany Woolley: 13:26

I was going to say was that your drive?

Anthony Caliendo: 13:29

to. I just wanted stuff that I never thought I would have.

Tiffany Woolley: 13:33

So you know those were your bars that you set for yourself.

Anthony Caliendo: 13:36

The more I spent, the more I wanted to make. Correct Right, so they used to call me Kelly Spendo.

Tiffany Woolley: 13:41

Yeah, like Caliendo, but Kelly Spendo. Yeah, like Kelly Endo, but Kelly.

Anthony Caliendo: 13:43

Spendo. That led into me actually becoming a supervisor running gyms six gyms At 23,. They sold Chicago Health Clubs out to Bally, okay, and then Bally bought them out. And then the guy who molded me his name is Al Phillips I'll never forget him, the guy that molded me, who abused me. You can't do this shit nowadays.

Anthony Caliendo: 14:10

But this guy he took a liking to me because of what I did that he didn't think I could do, and he mentally abused me, right? What I mean by that is we would have 25 managers of men and 25 managers of women, and then every night we'd have to get on a call and do our numbers right. Well, I was in the worst gym in the city right.

Anthony Caliendo: 14:35

And he would just abuse me over the phone, right, he'd just like Kelly Endo, do me a favor. He was English, right, so I'm not good with his accent. He would be like, you know, do me a favor, lock the doors and shove the keys up your ass, right, you know, and, and and, go home and don't come back. And I was like what over the phone. I'm like embarrassed, right, and then we show up for a monthly meeting and he would annihilate me again, you know? I mean, was there a reason he felt and his mentality?

Anthony Caliendo: 15:05

was that if he could create that fire to make me mad enough to want to produce, so he was pushing you. It was his way, but his way worked. Okay, could I do that now? People would cry now, if I said that they would go in their home and say oh my God, that cannot happen. But that's the difference between sometimes the world has changed. Everybody wants to be nice. There was no nice.

Tiffany Woolley: 15:33

Either produce or go home. That was it. There was no discussion about it.

Anthony Caliendo: 15:37

So the pressure as an 18, 19-year-old kid was massive, because I was the one that was, but you handled it well. I learned that I can accept it and I can turn it right. I can overcome it and turn it into something positive because I did not like to be embarrassed. To this day, my own children which I have eight children to this day my own children know the last thing they want to do is embarrass me in front of anybody.

Voice Over: 16:07

Okay, that's like your.

Tiffany Woolley: 16:08

I said listen.

Anthony Caliendo: 16:09

I've embarrassed my whole life as a kid.

Voice Over: 16:11

Wow.

Anthony Caliendo: 16:11

You know, as you can tell, I'm, you know, probably six inches from being a little person, I'm sure Right, you know some Italians are, so of course you get picked on as a kid. And then I got some crazy Englishman abusing me mentally to try to get me to produce.

Scott Woolley: 16:29

I mean, it sounds like a horror story, right, but you overcame it and you achieved what you were, and that's the difference between, in my opinion, winners and losers, right.

Anthony Caliendo: 16:38

Which is why I wrote that book, the Sales Assassin, that first book that I wrote, the Sales Assassin.

Tiffany Woolley: 16:43

Was he the assassin?

Anthony Caliendo: 16:44

I was the sales assassin.

Anthony Caliendo: 16:46

Okay, what happened was as a kid. One day I was like 21, and I was with a group of people and they were kind of snobby. It was the north side of Chicago, wealthy people, right, and they're like you know well, what do you do? And I said, well, I'm a gym manager. They're like you know gym manager. So you're just a salesman, right, is that what? You are, a salesman? And I'm with some doctors, attorneys, I'm just a young kid and I go no, no, no, I'm not a salesman, I'm a sales assassin. There's a difference.

Anthony Caliendo: 17:13

And that's how the book was formed, I called myself a sales assassin, skipping over something.

Tiffany Woolley: 17:23

You know, at 19, I opened up my first martial arts school which is another reason.

Anthony Caliendo: 17:26

So was that your first entrepreneurial? The first entrepreneur was my dojo, right Okay, which was called the Asian Fighting Arts Academy.

Scott Woolley: 17:38

Joe Gautier, which I'll have to send this to him because he loves when I talk about him, because he was an amazing person. But how did you jump to that when you were involved in martial arts?

Anthony Caliendo: 17:42

I liked it. When I was a kid, I did wrestling. I was a kid, I did wrestling, I did judo, I did some kickboxing. So I always felt like I wanted to really get involved in that. And then one day, this Green Beret, joe Goytier, from the gym comes up to me and says do you want to open a gym with me?

Anthony Caliendo: 17:59

Well, I had some money. I was a kid and I said, hell yeah, let's open up a little gym. And we rented a little facility and started the gym and had great success with it.

Tiffany Woolley: 18:07

And that was your first leap.

Anthony Caliendo: 18:09

That was my first real leap into starting my own business at 19 years old. Did you leave the health club? Of course not.

Tiffany Woolley: 18:15

That was just a side little hustle, you were used to having a lot of irons in the fire. Obviously that started in high school when you were juggling three jobs. It started as a kid, I mean.

Anthony Caliendo: 18:25

I have to stay busy, right? It's kind of like you know a shark in the ocean, right? Believe it or not, if a shark stops swimming, what happens to him? He drowns. Okay, known fact. They have to keep swimming. You can't just you know most sharks have to keep swimming.

Anthony Caliendo: 18:40

So you know that's kind of how I felt, you know. But you know some of the things that were put into my brain by this Al Phillips guy who you know tortured me, you know mentally, you know I mean I'll never forget. You know this is a crazy story but it's great for the listeners to hear because this story is. One day he's sitting on his it's like 5 in the morning and he's on his uh couch watching tv and drinking some coffee before a monthly meeting and he's watching the uh the channel where there's like animals, like animal planet or something like that and he, he sees a leopard right and he and he tells his story to us at the, at the actual event, with all the managers, and he goes.

Anthony Caliendo: 19:21

You know, I was watching tv this morning and I thought about all you managers and I seen a leopard. And I saw this leopard who started crouching back in the woods right and he's looking at this deer right and all of a sudden he sees this little deer and he comes hopping along and all of a sudden the leopard comes out, grabs the deer and starts eating the deer yeah, pounce. So I thought about all of you people here as managers You're not leopards, you're all prey, you're all deers, right. And I looked at him and I went and he said especially you, kelly. And I said, oh shit. So not only am I prey, but he singled me out of 50 managers.

Tiffany Woolley: 20:00

I'm not.

Anthony Caliendo: 20:01

Bambi. So he just, I think he liked me so much that he had to constantly pressure me and get me to a point where I would boil, but it sounds like that every time he did, you exceeded.

Tiffany Woolley: 20:18

So he was a pivotal person in your growth.

Anthony Caliendo: 20:18

He really was the person that basically challenged me. And if you're not challenged I mean you have to look at it If you're not challenged by people who are above you, how are they going to make you great? How are you going to become great? How does somebody become great? It's just wake up and say I'm going to be great. No, it doesn't work that way.

Anthony Caliendo: 20:36

It's a series of things that go through your life that basically mold you to who you're going to be for the future. So what did I want to be? Well, I basically mold you to who you're going to be for the future. So what did I want to be? Well, I wanted to be a father. Right, I wanted to have a better father because I didn't have one.

Tiffany Woolley: 20:49

Be a better father. I wanted to be a husband.

Anthony Caliendo: 20:52

I wanted to do everything that wasn't right for me. Oh, that's amazing. That was right for family, right To give what I didn't have. Was I mad about it? Was I angry? Yeah, you know, even now, my kids and my wife will sometimes call me an angry elf right, funny story I don't know if you've ever seen elf, but that's funny.

Scott Woolley: 21:10

Yeah we have many times.

Anthony Caliendo: 21:12

So, yeah, was I called an angry elf sometimes? Yeah, because I was always a little bit mad of not having what I wanted as a child.

Tiffany Woolley: 21:20

Right, and that was just a normal family. I think that's normal too, in a way, we all want what we don't have. We do, and we have to channel that into pushing us instead of a pity party.

Anthony Caliendo: 21:31

You're right, and it's good you say that, because for listeners that are listening, that's where you have to challenge yourself.

Tiffany Woolley: 21:38

Without a doubt.

Anthony Caliendo: 21:40

If you want it bad enough, how are you going to go get it? It's so true. There are people that get lucky.

Voice Over: 21:45

I've seen a lot of lucky people be at the right place at the right time and all of a sudden it does happen it was never going to happen to me.

Tiffany Woolley: 21:53

No, I understand, and it probably hasn't happened to you guys, but it doesn't mean that you can't get to that same end goal. I mean, I felt like, the sooner you, as as soon as you realize that you really are in control of where you end up.

Anthony Caliendo: 22:04

Yes, yes, and that's also the issue, because everybody wants to blame everybody else for their own problems their own issues.

Tiffany Woolley: 22:12

Yeah.

Anthony Caliendo: 22:12

You know they always want to put it on somebody else. You know, the only person that gets in the way of you is you, is you Right?

Scott Woolley: 22:19

And people don't accept that Well, it's not you, it's your head, it's your head, so going into the Sales Assassin.

Anthony Caliendo: 22:25

And how that book started, you know, was about basically mindset, mind preparation. What made me me and how can I write a book that's different than any sales book?

Tiffany Woolley: 22:37

And the.

Anthony Caliendo: 22:37

Sales Assassin was a book that was completely different. It was an out-of-the-box way of thinking of sales. It was about creating, you know, the mindset and the mind prep and the goals and everything they don't really teach you in sales 101 books.

Scott Woolley: 22:53

Most of them I don't even have the patience to read. So how many years later does that book come out?

Anthony Caliendo: 22:58

So that book came out in 2000 and I think 15.

Scott Woolley: 23:02

Okay, okay um many years later, many years later, you were already you know, I was already a sales assassin in many different fields you know, and you know.

Anthony Caliendo: 23:13

It just came to a point where you know that book needed to get written. It needed to get written for my legacy, definitely I was able to get it out a kid who didn't hardly barely finish high school but now write a book. But there was a lot of reasons. You know. We had Crystal Harvey, who was my business manager, who was an amazing writer and she could take me and put me in a book.

Tiffany Woolley: 23:37

Right.

Anthony Caliendo: 23:37

I couldn't do that. I can't.

Tiffany Woolley: 23:39

I'm not a writer, you know what I mean. So somewhere along the way you learned to collaborate and delegate as well. Yeah.

Anthony Caliendo: 23:45

Delegating. I've been good at delegating. I've never been such a micromanager guy because if somebody could do the job.

Anthony Caliendo: 23:53

They need to figure stuff out, just like I figured out stuff. Right, I can't be babysitting people. True, here's your task, go figure it out. Yeah, right, and that makes them a better person. You know, because that's kind of what was had. Was said to me Well, anthony, you need to get your numbers up. Okay, well, how do I do it? Okay, well, if, if, if that was the case, your numbers would be up, I don't know exactly how you do it.

Anthony Caliendo: 24:13

You just need to figure out how to do it Right In Chicago. What's next? What happens next?

Scott Woolley: 24:17

Because that's your first entrepreneurial business.

Anthony Caliendo: 24:28

So when Bally bought it out, you know, I had an opportunity where the main guy who abused me my whole time as a kid, al Phillips, said to me he goes, anthony, I'm going to go partner with Schwarzenegger, we're going to build World.

Scott Woolley: 24:41

Gym. We're going to build world gyms? No way, arnold Schwarzenegger, arnold Schwarzenegger.

Voice Over: 24:42

No way, we're going to build world gyms.

Anthony Caliendo: 24:44

I go get the hell out of here, you know, and he goes. So this guy ended up going yes, I'm selecting you out of everyone to manage the gym for us.

Scott Woolley: 24:52

So he liked you. Even though he was rough with you, he respected you. That's it.

Anthony Caliendo: 25:00

If anybody can overcome anything, who can get kicked in the face a million times and come back? I was like you remember as a kid weeble wobbles.

Tiffany Woolley: 25:08

Yeah, yeah, yeah, you'd knock me down, I'd wobble back up.

Anthony Caliendo: 25:11

You'd knock me down, I'd wobble back up.

Scott Woolley: 25:13

But that's a good lesson that anyone listening should think about. They should.

Anthony Caliendo: 25:18

It's about never giving up, Just don't quit right, just don't quit, no matter what happens, don't quit, you're this close you are. So when that happened, I went to the.

Scott Woolley: 25:29

Well, a lot of that skill comes from being a good salesperson, because a good salesperson is getting that door slammed on them and every time that door gets slammed it's an opportunity for another door possibly to open.

Anthony Caliendo: 25:41

I mean, think about it. Is it their gift of the gab? What makes a great salesman?

Scott Woolley: 25:45

I mean think about it. Is it their gift of the gab? Maybe no, I?

Anthony Caliendo: 25:48

think it's the consistency, the persistency, correct? Is it their ability to hang in there when things suck and aren't going their way, to be able to figure out how to make it happen? There's a lot of great salesmen, but they're never going to be great entrepreneurs. True, they're just good at sales. True, I was good at marketing and sales. So when I got the job for World Gyms, he said to me look, anthony, we're going to open up this gym on Montrose Avenue off Lakeshore Drive in Chicago. It's going to be amazing. I said man, I can't wait. Arnold Schwarzenegger showed up to the opening. I got to go to the Arnold Schwarzenegger Classic every year. I mean, here's a 23-year-old kid sitting in Ohio at the Arnold Schwarzenegger Classic with Lou Ferrigno, franco Colombo, sergio Olivia. Arnold Schwarzenegger, lou Ferrigno More passion.

Anthony Caliendo: 26:38

Here I'm at a table right sitting here and I'm just a young kid, right. So now I got a lot of fire. Second gym we opened across from the Mercantile Exchange on the river in Chicago. I killed that. I ate that gym up All the guys from the. Merc with all these badges would come over and they had all the money and they would pay in full. Pay in full, pay in full. We didn't have enough. They had so much cash and we rocked that gym.

Anthony Caliendo: 27:08

After the second gym I was supposed to get some kind of like equity, right? Okay, now it's 24 at the time or 25. Um, that didn't happen, so I refused to do the third gym because I wasn't going to be used right now I love you, but that's enough. Now it's my turn. Okay yeah well, you know how it goes. Some people are just tight with their wallet. They don't want to give you what you should deserve. And here's another lesson If you don't get what you deserve, move on.

Anthony Caliendo: 27:32

Yeah, move on, don't stay, that little I left a business that I loved, that I was the best at, but I realized it wasn't going to take me where I wanted to go.

Scott Woolley: 27:42

So where did you move on to?

Anthony Caliendo: 27:44

It's funny. You say that I was across from the Merc, so what do you think happened? I get all these guys that will come in and say, listen, you should be a stockbroker. I said what's a stock?

Tiffany Woolley: 27:52

What do you mean? What's a stockbroker? Did you teach yourself that?

Anthony Caliendo: 27:58

I don't know about being a stockbroker. What did I do? Okay, you've got to get a Series 7. Oh shit.

Tiffany Woolley: 28:03

Back to school.

Anthony Caliendo: 28:04

This is the hardest, second hardest license to pass. First is the bar probably.

Voice Over: 28:09

Second is the.

Anthony Caliendo: 28:09

Series 7. Right. So I said this is going to be difficult. And here is Did you end up getting it?

Voice Over: 28:17

I wound up getting it after the third time.

Anthony Caliendo: 28:19

And if I didn't pass and I passed it right with a 70. If I didn't pass it the third time, I had to wait a year, I believe. Oh great, at that time I didn't have a job, I had money in the bank. I was losing everything. Were you married? Yet no Car got repoed, oh jeez. I mean it was behind on mortgage payments, had to give up everything. I wound up sacrificing everything that I did just to prove a point that you could pass that test, and the point was I'm going to pass this damn thing.

Anthony Caliendo: 28:47

I'm not going to give up and I'll never forget when I passed it and I got my Series 7 license and then my 63.

Tiffany Woolley: 28:54

Now what?

Anthony Caliendo: 28:55

I went into the firm and I just started annihilating it, you know? I mean, I just Cold calling and all that Cold calling you know cold calling a guy and getting on the phone and basically introducing myself to him, Did you?

Scott Woolley: 29:09

enjoy that.

Anthony Caliendo: 29:10

Oh man, it was probably one of the funnest things. It was so amazing to get people to send you money. You never really met them. You've got to try to make them money, right.

Voice Over: 29:19

You can't just continue to lose their money. They're going to leave you.

Anthony Caliendo: 29:25

So that's when I got into Wall Street. I made a lot of money, I was very successful, super successful, but you know, that's In Chicago, yes, in Chicago. And then we moved down to Florida and we moved the branch down here, which is how I came back here another time. So I wound up coming back here again. But what made you come? To move to Florida the firm decided they were going to relocate to Florida.

Scott Woolley: 29:45

Oh, okay.

Anthony Caliendo: 29:46

They shut their New York office down and their Chicago office.

Tiffany Woolley: 29:49

They're like look, we're all going to Florida.

Anthony Caliendo: 29:51

We're going to go enjoy ourselves. And they picked the top 25 guys and we came. Okay, it was a great learning experience, but I learned how to be a trader. I learned how to do options. I learned stuff that I couldn't have learned this in school. Correct, okay? So to this day, I'm still a day trader.

Anthony Caliendo: 30:10

I still trade my own account every day, every day, and I have good days and bad days, and my employees all know, because they can tell that the market's not going well, you know. But look, I've always been a risk taker. Okay, and being a risk taker, I will give it all up to take risk if I believe in what I'm doing and if I lose, I'll shake it off and I'll start over again.

Tiffany Woolley: 30:32

Go again.

Anthony Caliendo: 30:33

So I don't really care. The money is not what motivated me, and a lot of people might think that, no, I could care less about money. I can't take it when I'm dead. Yeah, I can't take it when I'm dead. Yeah, okay, what am I going to do with it? Just give it to my kids, give it to my family, okay, maybe that's motivation, but I'm not giving them nothing.

Scott Woolley: 30:49

They're going to earn it. But do you have a wife at that point?

Anthony Caliendo: 30:52

No, I didn't get married until I was 30. Okay, so at 30 years old, I had a goal, and here it goes assassin. This was even goals that I set for my life, right?

Tiffany Woolley: 31:04

Did you write these goals down? They were always in my head.

Anthony Caliendo: 31:08

I always knew what I wanted to accomplish. I was methodical on figuring out like a surgeon. You know what I wanted? And I said, when I turned 30, I had a child at 18, 19, 19 years old. Unfortunately, I didn't marry her, but I raised a child, okay, so I had a child young, okay. And then at 30, I said, look, I want to get married, you know, and I want to have a son. Right, I already had a daughter, Right, so I want to have a son and give my son what I didn't have.

Tiffany Woolley: 31:35

Yeah, right that was my goal.

Anthony Caliendo: 31:37

Well, now I have five sons and three daughters.

Tiffany Woolley: 31:41

Unbelievable.

Anthony Caliendo: 31:45

What a blessing you know, so you could see that it's about goal-oriented and you can't always reach your goals?

Tiffany Woolley: 31:48

Do they work with you?

Anthony Caliendo: 31:50

You know, I had my daughter working with me. I had my sons working with me. The problem with them working with me, with my own children, is I am too aggressive and I don't accept any laziness or any. You've got to move as quick as I move and not many people can do that.

Anthony Caliendo: 32:08

So my kids are all successful. My daughter's in college her third year to be a nurse, practitioner nurse. My other daughter's going to be an attorney. My other two sons are master mechanics. They've been at Honda since they're 18. They run pretty much at. My One son, giovanni, is at jetscom. He's one of the top jets broker for a massive company at an early age.

Tiffany Woolley: 32:31

Wow.

Anthony Caliendo: 32:32

My other son sells health insurance. So they all kind of have that, so they all have that fire in them and that drive in them and I don't give them anything. I mean, I had the ability to do a lot, but I choose not to because I will not allow them to think you don't want to rob them of that either. No, because they have to learn how to stand on their own.

Tiffany Woolley: 32:52

Two feet yeah.

Anthony Caliendo: 32:53

You know I mean I watched my mother struggle to keep food on the table and a roof over her head and cry at night when I was a child and I never wanted their own person and be able to take care of their own responsibility. My children don't call me for money. They know they would rather, you know, get it from a friend than have to call me. Okay, because I'm going to give them the riot act and say what are you doing wrong?

Voice Over: 33:22

What's the problem? What's the issue?

Anthony Caliendo: 33:25

You know, because I'll dig it out of them Remember what I do for a living. Now is you know, I load my gun with ammunition. So in my book the Sales Assassin, the first book I wrote, we say silent and listen are spelled with the same letters. So you have to learn how to be silent, which is tough for me because I'm nicknamed the mouth of the South Right and then you have to listen. So that's one thing that I try to stick to.

Scott Woolley: 33:51

So you're a stockbroker? You're selling stocks? Yes, but I'm guessing from what I'm hearing from you. At some point you woke up wanting to change that.

Anthony Caliendo: 33:59

I did want to change that because I became an option trader. And really what happens when you become an option trader and a trader you become kind of a junkie. To a certain point you want more. It's no different than doing drugs or alcohol when you're addicted to something, it becomes an issue.

Tiffany Woolley: 34:17

Yeah, it's a problem.

Anthony Caliendo: 34:18

So you know, I was addicted to the gamble, I was addicted to the high.

Tiffany Woolley: 34:23

It is legalized gambling.

Anthony Caliendo: 34:25

But, as you're raising a family and kids and a wife. The question is do you want to lose them or do you want to move on? My choice was to move on and I still trade for myself today. Right, you know, but having that weight on my shoulder that was so emotional and so bad to raise a family it just wasn't worth it.

Tiffany Woolley: 34:45

for me, it wasn't conducive. No, it wasn't. So did you make like an exit strategy from that to like be able to fill your cart with something else? I?

Anthony Caliendo: 34:54

did you know I made money. I tried different things. I started you know a company. I started a couple companies. I had a lead generation company. Okay, you know that lead generation company you know was very successful. You know, at the time it was called Lending Hope, it was like Lending Tree, and then it was all subprime and we had probably 60, 70 people on the phone generating leads.

Anthony Caliendo: 35:20

Wow, and we'd sell those leads. So many things that I've done little things here and there, but that kind of propelled me into the lead generation business, which I thought was a fun business.

Anthony Caliendo: 35:31

So when you say lead like emails or databases, at the time this was a little bit before emails I mean opt-in emails kind of came along and I got into that too. It's a whole other story but the marketing. And then I became a mortgage broker. So after getting all these leads and selling leads to New Century and Agers and Countrywide, they would buy $50,000, $100,000. With the leads off me, I mean it was a big business. It still is the lead generation business.

Anthony Caliendo: 35:58

So then we're getting to the main man now. Okay. So as basically the mortgage business was propelling and I was growing, and I started in that business with an idea that I'm going to generate some of my own leads, to actually generate my own mortgages, building your own brand. Building my own brand and building my own mortgage company. So then I would have a lead generation company which would now feed the mortgage company.

Tiffany Woolley: 36:23

It was a no brainer, it was a no brainer.

Anthony Caliendo: 36:27

So I started that. And then one day a guy comes to me out of the blue, some guy, I don't really even know him. He goes Anthony, hey, I heard you're in the mortgage business. I want to be an investor. I said you want to be an investor? Okay, well, I was on Wall Street. I'm like what do you got? He goes I'm going to give you some money. I go you're going to give me some money. This is getting better.

Voice Over: 36:46

You know, I'm not going to kill anybody. You know I'm Italian, but I'm not going to do that. He goes no listen.

Anthony Caliendo: 36:52

I want you to go on the radio and I'll pay for advertising. And I said, okay, let me, try.

Scott Woolley: 36:57

Go on the radio to promote your mortgage, to promote the mortgage company.

Anthony Caliendo: 37:00

So one day I'm on I think 560 QAM, okay, and Howard David at the time is one of the guys and he does the ad for the mortgage company that I have right now and says you got to call the main man, you got to call my main man, the main man, Anthony Caliendo.

Tiffany Woolley: 37:18

I got it.

Anthony Caliendo: 37:19

And it stuck, okay, and I said you liked what you heard.

Tiffany Woolley: 37:23

That's awesome actually, I love that, so I became the main man on accident.

Anthony Caliendo: 37:27

And then we bought 1-800-THE-MAIN-MAN themainmancom and then I started running the ads. Okay, and everybody knows who's in Florida for the last 25 years, knows my voice. Hey, south Florida, it's the main man, anthony Caliendo. There's almost no deal, I can't close. So everybody knows my voice. It's powerful on radio.

Tiffany Woolley: 37:47

Yeah, you do have a good radio voice.

Anthony Caliendo: 37:48

All the endorsers know me. You know, I mean everybody endorses me, from Joe Rose to Paul Castronova. I mean I've had Hank Goldberg, neil Rogers, I mean you name it. I've had people endorsing me. Recently I just had Hannity endorsing me on 610. Oh, very cool who actually did my commercials, you know, which was great, Because it's great to hear, like you know, Hannity calling me the main man.

Anthony Caliendo: 38:10

He's telling people to call my main man, the main man Anthony Caliendo. So whether you're on the left or the right, I don't really care, but bottom line is it is kind of cool, right, you know, no matter who it is. So that main man was created, you know, on accident. But it stuck. And then as that mortgage company grew and as I started to propel and I became the top branch in the country for this branch Okay, I think at the time it was Acceptance Capital Mortgage and we became the number one branch in the country and the mortgage meltdown happened.

Tiffany Woolley: 38:45

Right so 2008,.

Anthony Caliendo: 38:47

I think I had 160 employees five offices. Yep. So the main man was spending $100,000 to $150,000 a month in advertising.

Tiffany Woolley: 38:56

Unbelievable.

Anthony Caliendo: 38:58

Official mortgage company of the heat, the Dolphins.

Tiffany Woolley: 39:01

Oh, that's so.

Anthony Caliendo: 39:03

You'd go into the arena and you'd see the main man all around the arena. So, the advertising, and the main man blew up right. But then everything blew up right. The whole market blew up, the mortgage meltdown blew up, you know, and the main man blew up right, but then everything blew up, right, you know.

Voice Over: 39:14

The whole market blew up, the mortgage meltdown blew up, you know.

Anthony Caliendo: 39:17

And I sat there and went. I'm in trouble okay, I got all these leases. You know, obviously, you know what's going to happen. You start getting I mean they were closing banks. I would move the deals to one bank.

Voice Over: 39:31

They would shut down. I moved it to another bank.

Anthony Caliendo: 39:33

I had one guy move to four banks. I felt so bad for him I go look, you're bad luck to a good hunting dog. I'm sorry but I don't know what to tell you, man, because every bank closed. I mean, you know, from New Century to World Savings to, you know Country Ride. They were just down down down.

Voice Over: 39:48

It was a domino effect.

Anthony Caliendo: 39:50

So, at that time I was at a position where what do you do now, man?

Voice Over: 39:55

I've got to reinvent myself.

Anthony Caliendo: 39:56

I've got to reinvent myself. I have to start over again. And when you make money and you lose it all, and now you're at a position where you have to give it all back to start something else. And then obviously, there's lawsuits, there's leases you're negotiating.

Tiffany Woolley: 40:13

It lawsuits. There's leases, you're negotiating.

Anthony Caliendo: 40:14

It's a nightmare. Employees, are you having to let people go? It was horrible, right?

Scott Woolley: 40:16

It's just a horrible feeling to see you get up, you're dealing with a lot of negative energy.

Anthony Caliendo: 40:21

It's a lot of negative energy, but I had Al Phillips. I can handle anything right. When.

Voice Over: 40:26

I was a kid.

Anthony Caliendo: 40:26

I had that guy beating me up, so I wasn't about to beat myself up, beating me up, so I wasn't about to beat myself up, right? So? So, anyways, I got through that process and I remember, as a kid, my dad, you know, he was in the food business, right in the olive oil business and in the Italian cheese business. Go figure, an Italian in the olive oil and that's a full circle moment too.

Anthony Caliendo: 40:45

Yeah, so I said to him because at this time I actually started talking to him again and we were just having a discussion I said you know what? I'm going to get into food business. I'm going to become a food broker, stock broker, mortgage broker, option broker.

Tiffany Woolley: 41:00

I got food. Now what the hell?

Scott Woolley: 41:01

man, you know you eat it okay that's a totally different business, totally different game.

Anthony Caliendo: 41:06

So I said I'm going to get into food business right. So at the time there there was a plant in New Jersey that he actually did all the sales for in Chicago. They've been partners. They knew each other for many years, when the company started in 1983. And I went and I met with the people and I said look, I'm going to come in. I'm crazy, I'm a maniac, I'm going to come in. You guys have been around for 25 years, 20 something years. I go, I'm going to come in. You guys never did a food show. You don't do any marketing, you don't have a website, you're just a manufacturer who manufactures cheese. I said I'm going to come in and I'm going to rock and roll this place. So what do I do? I get the phone number 1-800-BIG-CHEESE. This is an Italian cheese manufacturer, but a cheese business.

Scott Woolley: 41:52

I mean a perishable item, that.

Anthony Caliendo: 41:55

Yes and no, because we dry cheese so it becomes shelf stable but it is perishable. Knew nothing about the food business and knew nothing about the cheese business.

Scott Woolley: 42:03

I buy 1-800-THE-BIG-CHEESE. You must have enjoyed cheese though.

Anthony Caliendo: 42:07

I enjoy food because my father was a chef and we loved to cook and we loved to eat we grew up in a very Italian family where food was the happiness of the family. So I said, okay, well, let me start over. So I start over. I buy the phone number 1-800-BIG-CHEESE, and then I make a bobblehead of myself. I made one with the main man.

Anthony Caliendo: 42:25

I make a bobblehead of me standing on a wheel of cheese like Captain Morgan. That says Anthony Caliendo, the big cheese, 1-800-big-cheese. I make 500 bobbleheads in China. They ship them to me and I send them out to all the top executives in the country in the food business.

Scott Woolley: 42:42

What kind of executives? Grocery stores we're talking about?

Anthony Caliendo: 42:44

grocery stores, manufacturers, you name it right, so I send out these bobbleheads and all of a sudden I'm on the phone calling companies qualifying and I realize the food business never had a guy like me in it.

Tiffany Woolley: 42:57

Never. There's a lot of industries that you don't realize that are like that. Yes, I mean mine's like, my industry's like that too. It's ready for a little shake-up.

Anthony Caliendo: 43:05

It's ready. You know it needed a guy like me to come in to shake it up. And I shook it up, man. I mean I went, I did food show after food show after food show, not only in the country out of the country, you know in Dubai, you know in China, in Germany. I mean I traveled all over and I did food shows all over the United States and the booth would come up. I made a 10 by 10 booth. They paid for it. I went to the shows and I became the big cheese Selling cheese and in five years I took the company from probably 18 million to over 40 million dollars 40, 50 million dollars. So I built a massive residual business. So what was wrong with what I was doing? Nothing, it was the marks. I realized that if you're going to get ahead, you have to build something in my opinion, residual.

Tiffany Woolley: 43:58

Yeah, they say, you want to make money when you sleep, correct, and that was my dream.

Anthony Caliendo: 44:04

And this time we had fax machines.

Voice Over: 44:05

So I said look.

Anthony Caliendo: 44:07

I'm going to sell so much cheese that I'm going to wake up and people are going to fax orders and I'm going to come in and they're going to come in, and boy did they.

Anthony Caliendo: 44:14

First year I did $3 million. Second year I did $6 million. Third year I did $9 million. So I broke the barrier of actually taking something I knew nothing about, created a brand, the Big Cheese, marketed myself and basically had to go out there and get the accounts, but the food business didn't have somebody like me. I mean. I'm relentless on the phone, you know. Take in mind I was relentless in the health club business relentless in the brokerage.

Anthony Caliendo: 44:44

I'm a relentless guy, will not give up on you. If you give me an inch, I'm going to wear you down until you give me an order Just the way it is In inch. I'm going to wear you down until you give me an order Just the way it is, in a professional way that.

Tiffany Woolley: 44:55

I'm not annoying, but I'm persistent. So were you going to an office at this time? I had my own office.

Anthony Caliendo: 44:59

I had a little tiny office that was on Linton, over here and Dixie, in that little building there, that was maybe smaller than this tiny office here. Okay, you know, and that's kind of how we started.

Scott Woolley: 45:10

So are you an organized individual in terms of your you know?

Anthony Caliendo: 45:15

your calendar. I'm completely a mess.

Scott Woolley: 45:17

I am the most unorganized person Because from what you're talking about and the amount of sales that you're doing and being relentless and continually calling and calling to get the sale. You got to be somewhat organized.

Anthony Caliendo: 45:30

I'm good at figuring out the persistency. But it's all paper. We print the paper, we put it in front of me. I make my little notes, I keep calling and calling and calling until I decide I'm going to throw it in the garbage. But the thing about the food business was interesting. Nobody told me no, Nobody ever told me no. Wow, so there was no resistance.

Tiffany Woolley: 45:54

Now you take a great salesman and you do well off of resistance. Actually, I enjoyed resistance. I didn't have any. I was actually pissed.

Anthony Caliendo: 45:57

I'm like, can somebody just tell me?

Voice Over: 45:59

Yeah, shut the door, Anthony. Go screw yourself.

Anthony Caliendo: 46:00

Don't call me ever again. Not once, not once, because they never knew when they needed me.

Scott Woolley: 46:06

Okay, so I was persistent, but you also must have been selling a good product as well.

Anthony Caliendo: 46:11

We were selling a product that obviously people needed Okay, it was a niche product that not everybody does. We perfected the art of custom blending cheese. Okay, we would custom blend the cheese based on price and quality.

Tiffany Woolley: 46:26

So, like cheddar and horseradish, only Italian hard cheese. Okay, parm.

Anthony Caliendo: 46:29

Ramada, just Italian hard cheese. Why Italian hard cheese? Okay, parm Ramado just Italian hard cheese. Okay, why Italian hard cheese? Because it doesn't mold as quick, gotcha.

Voice Over: 46:35

Okay, so it's longer shelf life.

Anthony Caliendo: 46:36

We can dry it down, you know so. And then there's different types, right? You know when they're getting served Parmesan in the prison, you think that's all real Parmesan.

Voice Over: 46:45

No, it's too.

Anthony Caliendo: 46:47

There's alternatives, there's imitations. So we became very good and the best and to this day we still are the best at custom blending those products for price and quality. Now I still sell tens of millions of dollars a year in that cheese business. Okay, I built the residual business, which allowed me now to do what? To bring the main man back, who?

Tiffany Woolley: 47:11

was sitting on the shelf.

Anthony Caliendo: 47:13

Okay, just waiting, just waiting for the ultimate time to come back out. Right, you know when is he going to come out? So at the time I had somebody that I always kind of looked up to and I watched him, and that was Andy Cagnetti from Transworld, who was a business broker. He owned an unbelievable company with a lot of branches and I said, you know, I've done it all I could imagine how incredible I would be at this.

Anthony Caliendo: 47:38

I didn't realize how hard this business was when I got into it. Okay, and we'll talk a little about that if you don't mind. It is the hardest business and sales Food Anybody no, okay.

Tiffany Woolley: 47:50

The business brokerage Gotcha Selling businesses, selling businesses Like a franchising? Nope, or is that something different? Nope, okay.

Anthony Caliendo: 47:57

We're talking about.

Tiffany Woolley: 47:58

Let's say, you're a design company and you say to me Anthony, I want you to sell my business.

Scott Woolley: 48:04

So a person who owns a pizza place a laundry mat.

Tiffany Woolley: 48:07

I understand, okay, it could be anything.

Scott Woolley: 48:09

A bookstore. There's so many businesses out there.

Anthony Caliendo: 48:11

A dentist's office I mean, I've never realized how many businesses are out there.

Scott Woolley: 48:15

Right.

Anthony Caliendo: 48:15

Because, I've seen them all, sold them all and done it all. Okay, I mean, I had a guy call me from the radio and says you're never selling my business, main man, and I said, well, that's a challenge, let's get started. And I said you do what.

Voice Over: 48:29

He goes, I service microscopes.

Anthony Caliendo: 48:31

I go what do you mean? He goes. I go to universities and hospitals and I service the microscopes. Unbelievable. I said that's a job. That's amazing. It turns out the guy's netting like $300,000 a year servicing microscopes. I said, oh my God, what am I doing? You know, this guy's making a ton of money.

Scott Woolley: 48:47

So what's your first business? You decide you're going to start selling businesses. What's the first business that you sold? What did they do? You know?

Anthony Caliendo: 48:54

I have to remember I sold so many now that I've sold businesses that I have to say nobody else would ever have sold.

Tiffany Woolley: 49:03

And do you have any personal attachment to them? Yes, I do.

Anthony Caliendo: 49:08

Some of these people I sell business with I still go fishing with. I still talk to. I built relationships Because think about what I do right now. I take a person who might have owned a company for 30 or 40 years, or 20 or whatever the amount is, and they're passionate.

Anthony Caliendo: 49:22

And they love their baby, right? Yep, they might not be the best person to run their own company, and I'll tell them that, right, Because people sometimes keep their company where they want to keep it, where they're comfortable keeping it Correct, right? So if they're doing a million dollars a year, and they're comfortable doing a million dollars a year, even though they might be able to do $5 million or $10 million, they don't want to or they don't know how to In most cases, they don't know how to scale it yeah.

Tiffany Woolley: 49:50

They don't know how to leverage, which is a whole other part of business growth. They don't know how to do integration through acquisitions.

Anthony Caliendo: 49:54

They don't know how to do vertical integration, and I didn't know how to do all this stuff, neither you know, so I realistically didn't even know how to read a damn tax return, you know, so I have no accounting experience, so this business was the most challenging business I've ever done in my life.

Tiffany Woolley: 50:12

And vast.

Scott Woolley: 50:13

But where did you wake up going? Today I'm going to start a business of selling businesses.

Anthony Caliendo: 50:19

So what happened was that one time, a long time ago, I helped a friend you know who was selling an optical center and I said listen, I got a lead company right and I'll generate some leads and we'll try to find a buyer who buys your optical center.

Tiffany Woolley: 50:32

Right.

Anthony Caliendo: 50:33

And he tried to sell it for two years.

Tiffany Woolley: 50:34

Unbelievable and.

Anthony Caliendo: 50:35

I said I don't want anything, OK, I'm just going to help you. Right? He became a friend of mine, you know, and I said let me just try it, and I bought data and I created this fax campaign and I sent it out to all the opticians.

Tiffany Woolley: 50:47

It was by accident.

Anthony Caliendo: 50:48

Wow, and I got a call and I sold his company, you know, and I got a buyer, they took care of it, he got an attorney, they got an attorney and they did the transaction. So I didn't generate any commission off of it, I just did it to see if I could do it Right. And at that time I said man, and it didn't hit me at the time. What hit me at the time was when the cheese business I got to a point where I got to where I think I was going to plateau and I was starting to lose a little bit of passion.

Anthony Caliendo: 51:16

And I said, okay, let me do something else. And then I looked at Andy Cagnetta's company, which has great company, and I said you know, I think I could sell businesses. What did I have to do? I had to get a license. Here we go again.

Scott Woolley: 51:30

You need a license to sell In 35 states. You don't need a license to sell businesses, but of course in Florida, you do.

Anthony Caliendo: 51:35

You could go to New York and sell a business and don't need a license. You could go to New Jersey and sell a business and not use a license.

Scott Woolley: 51:41

But in Florida you have to have a license. Well, to cut hair in America, you have to have a license.

Anthony Caliendo: 51:53

So I said, oh, God, I've got to do and I'm too old for this shit. I don't know if I can do it. Man Is there actually a school to sell businesses? No, as a matter of fact, there's no questions on the damn real estate test about selling a business right, I don't think I had one question about selling a business.

Tiffany Woolley: 51:59

So how do you get? Is this a form you got to fill out?

Anthony Caliendo: 52:02

You got to take the state test to become a realtor to A license. You need a real estate license, you need to be a sales associate.

Scott Woolley: 52:12

Oh, my God.

Anthony Caliendo: 52:13

That's crazy, you know. So that's kind of how it started, right. So I'm like, okay, well, I'm going to get a license. I got a license, started a company. We got a broker, because you have to be qualified, you have to have a broker, and that's kind of how the main man came back again, you know, um, and it started, you know again, as I'm going to bring the main man back here, I am back on the radio again, back advertising again really, but you had those skills I did and I had the connection but you had those skills, but now you're selling businesses.

Scott Woolley: 52:47

Now I've started a lot of businesses in a lot of different industries yes, and there's a learning curve for each one of those. But every day you've got a lot of businesses in a lot of different industries yes, and there's a learning curve for each one of those, but every day you've got a new business that's probably calling you or you're reaching out to, so you have to be going through a learning curve almost every day, or every time a new client comes in.

Anthony Caliendo: 53:04

Every single day. I say right now, by selling an enormous amount of businesses already, I can actually say I know a little about a lot.

Tiffany Woolley: 53:14

That's awesome.

Anthony Caliendo: 53:15

Okay, because I know how businesses tick. I don't just look at their financials. You've got to understand I'm the guy that digs, okay, which is why I wrote that book how to Flip your Biz and Cash Out. Big it took me about. That's your second book. No, that's my fourth book. Fourth book okay, my big it took me about. That's your second book. No, that's my fourth book. Fourth book yes, my second book was written with brian tracy, called cracking the code to success okay that book was written with brian tracy and um, the sales assassin, my first book.

Anthony Caliendo: 53:43

Brian tracy endorsed it oh, that's a great name to have endorsing your first book, oh yeah yeah, if you want to ask me how that happened, boy, this is another story.

Tiffany Woolley: 53:52

I could keep going, but I know we don't have a lot of time, but there's so much information, but that story was as a kid I was 16.

Anthony Caliendo: 53:59

I was selling waterless, greaseless cookware door-to-door with a display case.

Scott Woolley: 54:02

Waterless, greaseless cookware yes, it's crazy right.

Anthony Caliendo: 54:12

Nuts, right, I'm selling. And there was a Brian Tracy event. Well, I had to pay like $250. Yep, well, I saved up $250.

Tiffany Woolley: 54:14

And you were like I'm going.

Anthony Caliendo: 54:15

And I went to a Brian Tracy's my first sales seminar.

Scott Woolley: 54:18

Wow, so I had a business, a television production business. I had 24, 25, 26 salespeople in that production company Every year when Brian Tracy and Zig Ziglar would come yeah, one of my favorites. I would take everyone to go see it For the whole day.

Anthony Caliendo: 54:35

It's great.

Scott Woolley: 54:36

Sometimes it was two days.

Anthony Caliendo: 54:37

It was like the beginning, like in an arena, yeah, and that's what happened to me, because I basically, when I went to that Brian Tracy thing, I realized I'm going to be a salesman for the rest of my life. This is what I want to do. So I sent a letter to Brian Tracy telling him the story that I was 16 years old. Okay, I sent him a nice letter, we got his information in Canada, we sent him a copy of the book and, believe it or not, he sent it.

Tiffany Woolley: 55:01

He read it.

Anthony Caliendo: 55:02

He read the book, he sends a letter back and he goes. Unbelievable book.

Tiffany Woolley: 55:06

That's amazing. I will endorse your book on the cover. That's amazing.

Anthony Caliendo: 55:10

So that was kind of like an unbelievable win, right? Because now I've got a book coming out with Brian Tracy endorsing it. Huge as a kid who didn't have the college education or the skills.

Tiffany Woolley: 55:26

So you know after that, but you really did have the skills.

Anthony Caliendo: 55:28

I had the skills, but I didn't really have what a lot of people have and I always wanted right. I would love to win the skills.

Tiffany Woolley: 55:33

I had the skills, but I didn't really have what a lot of people have and I always wanted right. I would love to win the college. The organization, I guess, is what you're.

Anthony Caliendo: 55:39

I could have cut some of my time down by understanding a lot of things because school does help.

Scott Woolley: 55:44

I went to college for four years and got a degree, but I learned more in the extracurricular things that. I, I did working clubs that I joined and other things that I was doing. That's what you learned.

Anthony Caliendo: 55:55

That's what I learned On the job experience and learning.

Tiffany Woolley: 55:57

Correct.

Anthony Caliendo: 55:58

And you have to learn from your mistakes right, totally you know your losses right. It's your losses that make you strong right, it's when you lose.

Anthony Caliendo: 56:04

You know that makes you strong, so you know. So after that book, his agent called me. Well, after the sales assassin, the agent called me and said look, we're going to write a book with Brian Tracy Cracking the Code of Success. You in, I said I am in, so wrote a book with him. After that got a call from another agent with Jack Canfield who wrote Chicken Soup for the Soul. Oh, I love that one and we wrote a book called the Recipe for Success with Jack Canfield.

Tiffany Woolley: 56:37

So now, here I am. Now you're an author, now I'm on the cover with Jack Canfield and Brian Tracy.

Anthony Caliendo: 56:39

So would you promote these books? Yes, like you'd be going on the radio, you would be.

Anthony Caliendo: 56:41

You know what those books are really used, as I guess you could say a business card right it shows my ability to be around very successful people that believe in some of my ideas and my concepts, of what I say and what I've written Right. So so it's great. You know you can't get rich off books. You know I mean you don't get. You know there's not a big payday and people think they can God bless because it's so hard. Ok, I hope you can.

Scott Woolley: 57:04

Right, yeah, well, there's one or two every year, but they become, you know, yeah, but it's not. But it's not like the old days they're not.

Tiffany Woolley: 57:12

You know, they're not giving you checks now no, you're right, they are like business.

Scott Woolley: 57:15

So it's the same like the music business. It's not like that anymore. It's not like that anymore. Yeah.

Anthony Caliendo: 57:19

You know. So I mean, if you get lucky, you get lucky. I really never cared how many books I was going to sell. I cared about my ability to be able to constantly challenge myself, to go up to that next level, okay and to put myself in a position of strength by basically showing that I have the support of very successful people. You know, it just makes me look much more attractive right yes yes.

Anthony Caliendo: 57:42

So after about three years of doing the business brokerage and bringing the main man back and people will call me up and go. Oh, I've been listening to you for 25 years.

Voice Over: 57:51

You've been selling businesses for 25 years.

Anthony Caliendo: 57:53

I go well. I've been marketing for 25 years. I did mortgages and businesses, but I had great success and I was able to figure out what was the problem with selling businesses. What was the issue? And to this day it never ends. There's continuously roadblocks and obstacles that you have to be able to see 10 miles down the road before that deal gets blown up and for some people that think that you don't need a business broker to sell a business, jump in a lake.

Tiffany Woolley: 58:24

I would think you do.

Scott Woolley: 58:25

You need that independent person, but can you also help people like you were talking about? People have the skills where they can. They got a nice, successful business but they can't take it to the next level Scaling. Can you help a person, find that person to bring them in, maybe as a partner and sell part?

Anthony Caliendo: 58:41

of the business. That's not something that I would focus on. I'll tell you why, you know. First of all, obviously I can't control what people do in their decisions.

Tiffany Woolley: 58:49

Right.

Anthony Caliendo: 58:50

So if I'm not mentally and financially involved in the business, it doesn't make sense for me, right? Because I can't control what's going on. If you can't control what's going on, you're normally going to not have control. Correct, and not having control means it's a disaster, right? Okay, I'll give you an example. If I don't manage the buyer, the seller, the banks, the accountants, the attorneys, if I don't manage the whole process of the whole deal from start to finish, keep people moving, stop the garbage.

Tiffany Woolley: 59:19

Keep the egos out. You know, I become a psychiatrist.

Voice Over: 59:24

I got emotional issues, I got timing issues kills deals.

Anthony Caliendo: 59:27

I got attorneys that want to kill every deal. No offense to your attorneys listening, but you guys are crazy sometimes.

Voice Over: 59:32

Yeah, okay.

Anthony Caliendo: 59:33

You know, at the end of the day the seller wants to sell a business and the buyer wants to buy a business.

Anthony Caliendo: 59:38

The problem is there's too many emotions and too many people involved to screw up a deal. So a lot of times a deal will die three or four times before it even closes by mistake. Okay, I can't tell you the things that have come up in the end that are disasters for a deal, and I've overcome so many of them. It's so impressive for me to actually say say this right now, because I put myself up against attorneys who've been closing business for 20, 30 years and they couldn't figure it out. How does a kid like me figure it out who doesn't have a college education? Because I am the master at figuring out what is the problem and how do I solve it. I don't rely on them to solve it.

Anthony Caliendo: 1:00:20

I don't rely on the buyer to solve it, the seller to solve it, the attorney to solve it. The account I figure out how to solve the issue.

Tiffany Woolley: 1:00:25

I'm a problem solver. I'm solution oriented in my whole vibe of how. I I'm like, just give me solutions. I don't want to hear any more problems.

Scott Woolley: 1:00:36

So are you selling businesses just in Florida, or are they all over the country?

Anthony Caliendo: 1:00:41

Well, I can't sell all over, but my focus obviously has been in Florida. You know, because I'm here I can go meet people, I can go to their business. I find myself— so is that an important aspect of selling a business it is.

Anthony Caliendo: 1:00:52

We're launching now throughout the state of Florida. Right now we're selling businesses out throughout the state. Right now we started kind of going out of the comfort zone of just South Florida. I wanted to be in a position that, until I'm really really comfortable with everything I'm doing, that I'm not going to really expand the way I want to expand. The problem is I can't hire another Anthony Caliendo. It's impossible. There'll never be another Anthony Caliendo.

Tiffany Woolley: 1:01:18

Never. Well, you made yourself unforgettable.

Anthony Caliendo: 1:01:22

Correct and a lot of people can't do what I do. So for me to just hire a bunch of people and try to train them, it'll never be the same.

Tiffany Woolley: 1:01:30

How many can you work on selling at a given time?

Anthony Caliendo: 1:01:33

I mean on average I'll have anywhere from 10 to 15 deals on average. Okay.

Anthony Caliendo: 1:01:38

And what's the length of time, but I might have 30, you know, I might have 30, 35 listed, right, so I have more listings. But the problem is, even though you have more listings, you have listings that obviously are going to go quicker based upon the listing. The bigger the deal, the quicker it usually goes in most cases, unless it's a mess and I have to clean it up, which happens a lot of times. At the end of the day, what people sometimes don't do and business owners don't do and this is the biggest problem, which is why I wrote that book how to Flip your Biz and Cash Out Big. I took all the problems and all the issues and all the reasons why businesses don't sell. Believe it or not, eight out of 10 businesses won't sell. Can you imagine what are the top two reasons of why?

Voice Over: 1:02:22

I'm going to give you.

Anthony Caliendo: 1:02:23

But can you imagine if eight out of 10 homes didn't sell?

Tiffany Woolley: 1:02:25

No. Or eight out of 10 real estate no, yeah, you don't even think that. Can you imagine?

Anthony Caliendo: 1:02:28

Eight out of ten won't sell. So why is that? Yeah? Why does somebody work 30 years and never even think about how to exit their company?

Tiffany Woolley: 1:02:37

Yeah, that's pretty profound.

Anthony Caliendo: 1:02:38

Okay, and that's a majority of business owners, not only that, accountants and sometimes even their own owners. They don't show what they should. Show through the profits of the company sometimes the right way, and it's not illegal. Sometimes. Show through the profits of the company, sometimes the right way, sometimes, and it's not illegal. Sometimes they're taking more distribution. Sometimes they're paying off expenses through a company. All small businesses do it, there's nothing wrong with it. Okay. But when it comes time to sell a company, do you have everything it takes for a buyer to want to buy it, right? Is that company running only because of you? And I've sold companies that only run because of the owner, that's got to be tough.

Tiffany Woolley: 1:03:18

It's a very tough one, but you know, I always say there's an ask for every seat.

Anthony Caliendo: 1:03:20

You just got to find the right, ask right, you know. So, in a nutshell, it's understanding the business and them understanding what they're doing wrong. I don't sugarcoat anything. I am the most brutal, you know, right to the point in your face type of guy.

Scott Woolley: 1:03:34

And if you don't sugarcoat anything, I am the most brutal, you know right to the point in your face, type of guy and if you don't like me, don't deal with me, but if you don't like what I say, you learned that from back in your days at the health club with that guy.

Anthony Caliendo: 1:03:42

If you don't like what I, say then don't talk with me, because I'm going to tell you what you don't want to hear, like it or not. And then I'm going to tell you how to fix it, and then I'm going to tell you how I can solve it. And if you're not going to follow every direction, that.

Anthony Caliendo: 1:03:54

I take and you're not going to listen to me, then you don't need me, and I use this analogy sometimes If your neighbor right, one day your neighbors, god forbid. I hate to say this, but somebody got shot at your and they say that you did it. You're the neighbor that you came and you shot him and you killed him and you know you didn't shoot him right, you didn't do it right. But you get arrested and now you got to prove yourself right. Do you think that happens in the real world?

Tiffany Woolley: 1:04:17

Yeah, you better believe it does happen, yeah, probably more often than you want to. So what do you?

Anthony Caliendo: 1:04:19

do you go hire the cheapest attorney.

Anthony Caliendo: 1:04:27

You know, Well, that's how I feel with business owners. Their life is on the line. They need me more than I need them, and that's a fact, because I know what I need to do to get them to the finish line and how I need to get them to the finish line, and you're not going to go pay the cheapest attorney. So I tell people don't even discuss my commissions yet until I understand the deal and what I think it's going to take to sell it. And even if I think I could sell it, I will pay for myself because I will get more money than any other broker because of my ability to obviously figure out how to get your financials to look better and increase your profitability and show you how to do things differently. And I pay for myself.

Anthony Caliendo: 1:05:10

So, clients don't usually argue with me on my commissions. Do I charge more than every other broker? In most occasions, I do so why is an?

Anthony Caliendo: 1:05:18

attorney charged $900 an hour and another one charges $300 an hour. It's their experience, it's their ability to get the job done and have the reputation that allows them to make more money. Right, why do people get more money? Well, what did they do? Well, this is what I did my whole life. Everything I've done my whole life has got me to the point to do what I do right now. And I am the absolute best at it.

Tiffany Woolley: 1:05:43

Such an interesting facet of business, so one of the two biggest situations you run across in trying to sell a business.

Scott Woolley: 1:05:49

First is financials. Okay, First is financials.

Anthony Caliendo: 1:05:51

They situations you run across and trying to sell a business. First is financials. Okay, First is financials. They want to make the money but they don't want to show the money.

Anthony Caliendo: 1:05:55

Okay, if I said to you right now, if you had to pay $20,000 in taxes right now, what would you say to me? I don't want to pay $20,000 in taxes. That's the first thing you'd say to me. Correct, I need you to write a check for $20,000. Anthony, I'm not doing it. No, you are doing it. Here's why If you write that check for 20 grand, I'm going to get you another 200. You're going to net 180 for writing a check to 20. You want money now? If you answer no, then have a nice day, because you're not as smart as I thought. Right. So, obviously, adjusting the way you're doing your financials, the way you're making money, the way you're taking money, the things that you're doing, obviously we have to get it sellable, because buyers and banks look at one thing they look at bottom line, they look at what I call and this is why I wrote this book, because I don't call it EBITDA right, we all know what EBITDA is right Even people that aren't that talented heard the word EBITDA.

Anthony Caliendo: 1:06:50

Most people will never know what EBITDA is. Even business owners that I talk to don't understand EBITDA. Okay, they have no clue how to read their tax returns or understand EBITDA. No clue. Let's just say probably nine out of 10. How do you like that number? Is that crazy, crazy, okay. So what do I do? I create what I call net owner benefit. I call it NOB. The net owner benefit is what the person is truly making from their company. I'll give you an example If you're paying a car through your company and the buyer's not getting the car, that's an ad back, right, you know, if you're paying your health insurance or you're paying.

Scott Woolley: 1:07:27

You know you're paying a bunch of stuff for your car.

Anthony Caliendo: 1:07:29

You're paying a bunch of stuff through the company, right? So I have to figure out what that true net owner benefit is to that company and then I do my valuations. And then I do that for free, by the way. I value the company and if I think I can sell it I list it.

Anthony Caliendo: 1:07:42

But I will not list a company because somebody tells me. I had a guy the other day. He tells me well, this is what I want to sell for. I said hold on a minute, don't tell me what you want to sell for. I'm going to tell you what you're going to sell for when I get all this information. And if you don't want to send me all that information, I can. So true, you know because they just don't understand. Everybody thinks they got the prettiest baby.

Voice Over: 1:08:04

Of course. Oh, my baby's the most gorgeous baby in the world.

Anthony Caliendo: 1:08:07

No, your baby's ugly right now. Okay, it's not an attractive baby, and I'm the guy to say it, right.

Voice Over: 1:08:12

Yeah.

Anthony Caliendo: 1:08:12

So I got to make the baby prettier.

Anthony Caliendo: 1:08:14

Right, it's funny because so many of these all, but it's true, if you just be, honest with people and be truthful and just tell them what they're doing wrong and why they're doing it wrong and how to do it right. But they don't know, they don't understand. These people that own these companies have given their life to some of their employees, their dedication, they've raised their families. How can I tell them that they're doing everything wrong when they've raised their families and they're doing a lot? I need to explain to them what they need to do to get out.

Tiffany Woolley: 1:08:48

Yeah.

Anthony Caliendo: 1:08:48

Okay, not that they're doing it wrong, but they don't know how to do it any differently Because nobody's taught them. So I become the teacher. Right Now, I'm the teacher, okay.

Scott Woolley: 1:08:59

So that's kind of where I'm at right now, but I don't think most business owners are aware or realize that your service exists.

Anthony Caliendo: 1:09:09

I agree, that's true.

Scott Woolley: 1:09:11

I actually think that it should be is most people that are in business should come see a person like you at least a few years in, to help them guide for their business. No doubt about it.

Tiffany Woolley: 1:09:23

I know, and is there a mentoring side of you? There is, you know. I haven't really had.

Anthony Caliendo: 1:09:29

You know, what I tell them is this Look, I'm going to give you my free book, okay, I'm going to send you the link. Or send you a free book, yeah, when you read it, call me back, okay, if you don't, and I still help them of course, but it's always great if they read the damn book.

Tiffany Woolley: 1:09:51

They understand my mentality.

Anthony Caliendo: 1:09:52

That book was written for them to understand on what we need to do to get to the finish line, because it's all about the finish line, isn't it? It's kind of like, you know, being a designer.

Tiffany Woolley: 1:09:59

You know being a designer is an artist.

Anthony Caliendo: 1:10:01

You're an artist. Well, you're an artist in what you do. I'm an artist in what I do.

Scott Woolley: 1:10:05

You're a designer as well, because you're designing a plan. Deals Helping people sell their businesses.

Anthony Caliendo: 1:10:12

I mean, I am doing the art of the deal every day you are. Every day I'm doing the art of the deal.

Tiffany Woolley: 1:10:16

And it's fascinating that you do now get to have such a different perspective for each of these businesses. Like you get to almost start fresh every time you're bringing a new business to market.

Anthony Caliendo: 1:10:26

Yeah, it's exciting.

Tiffany Woolley: 1:10:28

It's fun, it is yeah and it's different. That's like so different. It's never the same, correct?

Anthony Caliendo: 1:10:31

You know, so it's always a challenge.

Scott Woolley: 1:10:33

There's a lot of and you recently designed a television show, Chef. We got the trademark not too long ago.

Anthony Caliendo: 1:10:45

The concept is me having fun with chefs and celebrities. Being I love to cook, we go out, we go to restaurants and celebrities. We just did Paul Castronova's house at his house. We just did a number one Italian restaurant in Orlando. I go out now and I cook with chefs.

Anthony Caliendo: 1:11:05

Which people can see on YouTube, and then they eat my cheese, okay, and my olive oil Because obviously I'm in the olive oil business, caliandofoodscom, so cheese and olive oil, so I'm still in the food business every day, right right, you've just been collecting these businesses along the way. So this is kind of a passionate thing for me to try to go out there and have fun. But the whole idea is to expose the chefs, make new dishes, have fun, and then we eat the dish and we go oh my God, that's chefed up right.

Voice Over: 1:11:33

So it's a fun thing to it, right? So?

Anthony Caliendo: 1:11:36

don't be surprised in the next couple of years. I have people all over the country going oh my goodness this is chefeduffed up.

Tiffany Woolley: 1:11:42

This is just shuffed up. That's one of the goals. I love that the future looks bright, that way, I know we're getting short on time.

Anthony Caliendo: 1:11:53

If you guys want to ask, me any other questions?

Scott Woolley: 1:11:54

No, we really appreciate you coming in today and going through all of this.

Anthony Caliendo: 1:11:58

Great energy, Last thing we need to talk about which I think is important to end on is the movie I was just going to ask you, right.

Scott Woolley: 1:12:06

So you produced a movie, you started the movie, yes. So here's a dream as a kid, right?

Anthony Caliendo: 1:12:12

You're a little Italian kid, growing up in an Italian family. What do you watch as a kid? Of course you watch Goodfellas.

Voice Over: 1:12:19

Of course you watch the.

Anthony Caliendo: 1:12:19

Godfather, you watch those movies. So as a kid I always said look, I want to be in a movie one day. Who doesn't want to be in a movie?

Voice Over: 1:12:29

I don't care what anybody says.

Anthony Caliendo: 1:12:30

I want to be in a mafia movie. So in 2020, COVID happens.

Tiffany Woolley: 1:12:36

Everything goes to crap. Perfect timing to build a movie.

Anthony Caliendo: 1:12:38

I wind up being in this little movie set as an extra right, you know, called Gravesend, and I meet some guys and Amana Sante, who filmed the movie Gotti, and you know some other guys and one of them comes up to me and says I got a great, great movie concept. We did a web series called Mob King. We had four series. You know, we obviously don't have the funding right now. And I said you know what I always wanted to be in a movie? What would be better than me actually funding the movie, controlling the whole thing, okay, and then rewriting the actual script okay, with my character, okay and then basically filming a movie and then figuring out how to sell the movie?

Anthony Caliendo: 1:13:25

One of the hardest things in the movie business is to make money. There's no doubt about it. Everybody invests in movies. Nobody makes money. So I figured, you know, this is a dream come true. If I make my money back, it's a plus, if I break even, it's a win. Okay, I said I'm going to make a movie. Crystal Harvey, who became the line producer who manages the back end, she's the one that kind of wrote all these books and she's been around for 16, 17 years With you yes, I said you're the line producer. You run everything, you manage all the back end, because I don't do back end, I'm front end right. I have three ladies that work for me now me now that work with me now Crystal, carla and Claudia.

Tiffany Woolley: 1:14:02

And it takes three seasoned women, you know.

Anthony Caliendo: 1:14:06

Just to keep up with me.

Tiffany Woolley: 1:14:07

Three seasoned women, and we're not talking about?

Anthony Caliendo: 1:14:09

we're talking about seasoned women. These girls are amazing, right Hard working, Amazing.

Scott Woolley: 1:14:13

Good juggling. You have a good team behind you.

Anthony Caliendo: 1:14:16

So after COVID, the only state that was open was Florida.

Tiffany Woolley: 1:14:20

So I said, okay, we're going to get everybody cheap, we're going to get everybody cheap.

Anthony Caliendo: 1:14:23

We're going to bring them down from LA and we got some amazing actors. You know James Russo, who was Donnie Brosco, and Django Unchained.

Tiffany Woolley: 1:14:30

You must have had the best time so it was an amazing time.

Anthony Caliendo: 1:14:34

You know a guy, ciro DiPaggio, who kind of dreamed this up, who actually did 19 years in prison, who came out, who decided he's going to make this movie and it was his idea, and it was about a guy who went to prison for 19 years and then came out and the family tried to kill him. Okay, so nice, isn't that?

Voice Over: 1:14:51

wonderful Right?

Anthony Caliendo: 1:14:52

So I said I love the concept, so anyways, we made a movie, okay. You shot it in Florida, shot it all in Florida Killed three people in my house in my truck.

Voice Over: 1:15:01

Oh my gosh, you know, I mean it was amazing Amazing actors, amazing story.

Anthony Caliendo: 1:15:06

It's a mafia drama, a family drama. It's not your typical. Let me go collect my money mafia movie.

Scott Woolley: 1:15:12

Yeah.

Anthony Caliendo: 1:15:13

You know, it's really kind of a very on the edge on the edge of your seat watching the movie. So, anyways, we filmed it, we finished it. I went to the AFM American Film Festival in California. I bought all the advertising. I controlled the whole thing. What I mean by that is everywhere you walked in that place was Mob King. They had no idea who Mob King was or who I was, and we dominated it. And then, we wound up signing a deal with Gravitas, which is a very big distributor.

Tiffany Woolley: 1:15:43

Yes, it is who took.

Scott Woolley: 1:15:44

Mob King on. So where?

Anthony Caliendo: 1:15:45

can people see it now? Amazon Tubi Pluto, I mean on demand. It just launched on May 2nd in 99 territories. Oh, amazing In 16 different languages on May 2nd of this year.

Tiffany Woolley: 1:15:57

Were any of your kids extras? Yes, three of them.

Anthony Caliendo: 1:16:02

First scene my son's in the jail scene. My mother loved that. You know what are you taking after your father.

Tiffany Woolley: 1:16:08

You got your son in prison now I'm like that's a movie, you know you know, my Isabella was my daughter in the movie.

Anthony Caliendo: 1:16:16

She was in a scene. You know my son Giovanni was on the yacht in the movie.

Tiffany Woolley: 1:16:20

It's so good.

Anthony Caliendo: 1:16:22

Yeah, it was an amazing story, but there's an accomplishment that I never thought I would be able to do in my life. I never thought I was going to be able to produce a movie and star in a movie and sell a movie.

Tiffany Woolley: 1:16:33

And you did it.

Anthony Caliendo: 1:16:34

And that's what I mean If you dream it, you could achieve it. You really can. The problem with people is they. They just don't believe in their dreams and they don't have to follow them.

Tiffany Woolley: 1:16:43

You have to go out, you just not and you just can't give up.

Anthony Caliendo: 1:16:46

I mean, I mean, it is you just have to get back up. Be that bubble yep, but it's been great to be on the podcast thank you so much for having us

Tiffany Woolley: 1:16:56

thank you, hope you guys had fun no charge for the entertainment okay, great the eye design lab.

Anthony Caliendo: 1:17:02

Yeah, and we will get you some caliendo olive oil and some cheese, by the way.

Tiffany Woolley: 1:17:05

I look forward to that.

Anthony Caliendo: 1:17:06

All right, so we're going to drop that off to you guys.

Tiffany Woolley: 1:17:08

Amazing, all right, great meeting you. Thank you for having me. It's been great to be here. Awesome, thank you.

Voice Over: 1:17:14

Idesign Lab iDesign Lab's podcast is an SW Group production in association with the Five Star and TW Interiors. To learn more about iDesign Lab or TW Interiors, please visit twinteriorscom.