S2 E03 | Jason Hennessey

Jason Hennessey:

In my old age home, when I’m 93, I want to tell the story of how I would walk around with $10,000 and we’d go on shopping sprees because of my gambling, and I want to tell about that I owned a Lamborghini. I want all the people at the nursing home to be like, “He’s just making stories up. He didn’t own a Lamborghini. Don’t listen to him.” Just like I do with SEO, right? I reverse engineer, so I’m reverse engineering me, at the nursing home, being the coolest guy at the nursing home, man.

Luke W Russell:

Welcome to Lawful Good, powerful partners, a series about interesting and caring folks that we know and trust whose journeys brought them to collaboration with the legal community. I’m your host, Luke W. Russell. I’m not a journalist, I’m not an attorney. I’m trained as a coach. I love human connection and that’s what you are about to hear. My guest today is Jason Hennessey, founder of Hennessey Digital. Jason grew up with a high value on hard work and family. His grandfather was a custodian and his grandmother made bathing suits.

Luke W Russell:

They were rich with love and family. A self-proclaimed hopelessly distracted C student, Jason cultivated a lot of independence growing up that guided him through his time in the military. As a young student, Jason found himself selling blow pops around school. As his career began to form, Jason found on his way into e-commerce, building a website for Vegas Brides, which is where he began cultivating his love and passion for search engine optimization, or SEO. In our journey today, we’ll explore how Jason values vulnerability, whether or not you can marry someone you just met, and the joy of polling pranks on loved ones.

Luke W Russell:

Jason, you had what some would call a bit of a rough childhood between evictions and an absent father. When you think back to those early years, does it stir up painful memories?

Jason Hennessey:

Luckily for me, I don’t really carry a lot of those memories. I actually have more of the fond memories of having the love and support of my mother who gave me everything that she could afford and my grandparents who were blue collar workers. My grandfather was a custodian at a high school and my grandmother made bathing suits. We weren’t the richest family in the neighborhood, but we were rich with love and family, I guess.

Luke W Russell:

Your biological dad, who just recently passed away, left when you were around 10, do I have that right?

Jason Hennessey:

It was probably more like six years old, I’d say, and then he kinda got reintroduced back into my life when I was probably like 10 or 11, I’d say.

Luke W Russell:

Do you feel like you were able to really start to build a relationship with him over recent years?

Jason Hennessey:

My father was kind of in a great state of depression and I think it was just because of, he was having to live the life of all of the bad decisions that he made. He was lonely, and I think you can disguise that and stay active. And he was very active with golf and this and that, and just living life. But eventually, the decisions that you make will come back to you. I think he started to realize that later in life and got really depressed, and that ultimately, it killed him, depression basically, yeah.

Luke W Russell:

Yeah. Is your mother still around?

Jason Hennessey:

My mom is, yeah.

Luke W Russell:

What’s your relationship like with her?

Jason Hennessey:

Yeah, my mom is … She was everything for me. I mean, she could have easily aborted me as a baby. You know what I mean? Like when you’re 17 years old, right?

Luke W Russell:

Yeah.

Jason Hennessey:

And she chose not to do that and have me. And she went through a lot in her life from my father not making the right decisions, to them getting separated and then divorced, to living with my grandparents, to having a tumor in her brain where she had to have major brain surgery. I think, when my mom ends up passing and dying, she’s going to skip purgatory and go right to heaven, man. She’s paid her dues, man. Yeah. She’s lived a tough life. I got a lot of great deal and respect for my mom.

Luke W Russell:

Yeah. So, your mom was around and then your grand, if I remember right, you said your grandparents really stepped in and took in this role. What was your relationship like with your grandparents?

Jason Hennessey:

My grandmother was like the more experienced mother figure. My mom, this was new to her. She was like, think about, like my kids right now are 17, and I can’t even imagine them having a child. That was the role and responsibility that my mother took upon herself. So, with the help of my grandmother, who had the more experience, and my mom would have to go out and work and my grandma and grandpa would watch after me. But I was very kind of much on my own too. I would walk to school in the morning, I’d walk home, even as far as like second, third grade, I could remember walking to school by myself.

Jason Hennessey:

Come home, I’d make myself a macaroni cheese or a bowl of soup and bowl of cereal until my grandma and my grandpa, or my mom got home. I was very independent, I guess, is this best way to use. My grandfather was an amazing man. He wasn’t rich from a monetary standpoint or a financial standpoint, but he was rich with his family and teaching me some of the old traditional values that I still, I take into consideration even today.

Luke W Russell:

What would be some of those traditional values?

Jason Hennessey:

Little things like, if I’m sitting on a subway and somebody that’s my senior gets in and they’re, like to get up and give your seat. That’s something that I kind of instill in my children or to say hi, and thank you, and please, and open the door for people. All of the things that people just kind of do, or don’t do. When people don’t do that kind of stuff, it’s pretty obvious. I think my kids are very fortunate because those values are now passed down to them too.

Luke W Russell:

Yeah. How did young Jason spend his time when he wasn’t in school?

Jason Hennessey:

I spent a lot of my time on the baseball field, for sure. A little place called Tanner Park in Copiague, New York. I was always a pretty good baseball player, and if you asked me what I was going to be when I got older, it was like a dumb question, because I was going to be a professional baseball player like, what do you mean? I just had a gift. I was one of the kids that would make the all-star team every year. That’s where I spent most of my childhood is there and riding my bicycle and hanging out with friends.

Luke W Russell:

At 14, I’m told you started your own DJ business, where’d you get the money to buy the equipment?

Jason Hennessey:

Yeah. I always had a love for music. At an early age, I kind of saw like, hey, like if you want to live life, try to find something that you love to do. Being that it was one of my passions, I guess, I would ask my mom for Christmas presents and birthday presents. For Christmas, I might have got like a CD player, and for my birthday, which kind of came right after Christmas, because my birthday’s in January, I might ask for a mixing board and then I might get some birthday money from other people and buy some speakers. I kind of rigged together my first little system, I guess. if you will. We had a block party in our neighborhood when I was probably like 16-years-old. There was like a mobile DJ there.

Jason Hennessey:

It was called Joey D’s Entertainment. And he was playing music and making announcements. It was a big block party. And then me and my buddy, we just started to break dance, which I think you could appreciate because I know you do beatboxing. So, we just started to break dance and then the guy, Joey’s like, “Man, that was amazing. How would you guys like to take this show on the road and perform at sweet 16 parties?” And I’m like, yeah. He goes, “We’ll pay you and you’ll get to party and you’ll get good food and you’ll get tips.” I’m like, that sounds like the perfect job.

Jason Hennessey:

I had already had like my own little makeshift kind of DJ system, so I was always already looking up to this guy that was playing the music. That’s how it got started. He hired us and we’d get paid like 75 bucks each to go, and we were called party motivators, and we would go to sweet sixteens and bring people out on the dance floor and dance with them and do a little show. Then from there, he trusted us and we became, instead of party motivators, I became the DJ, and then my other friend, Pete, became the emcee. Then we were now the actual stars of the show. I was DJing the party and he was emceeing the party, and so that’s kinda how that all got kicked off there.

Luke W Russell:

How do you get into break dancing? And that’s also not something for a person to casually do. You got to be physically fit to do break dancing.

Jason Hennessey:

Yeah. I don’t even know if we were really good at it. Growing up, in the ’90s, we had some of the inspiration from even earlier on, like listening to some of the old school hiphop like Run-DMC. There was always that kind of influence that I guess we had. We weren’t necessarily good. We would just kind of get down and try to do what we were doing. I guess we caught the attention of this guy, Joey, and he was impressed, and I was always athletic. We’d do like a flip and whatever, get down on the floor and kind of circle around.

Jason Hennessey:

I don’t even know what the moves are called, but we were just kind of doing them. I wouldn’t say I was kind of like trained or I didn’t go to any dance schools or anything like that. It was just more of like freestyle, I guess.

Luke W Russell:

Can you still pull off a back flip these days?

Jason Hennessey:

Oh my God, I would break my back. Yeah, not going to happen.

Luke W Russell:

How did you get your first clients as a DJ?

Jason Hennessey:

Obviously I was doing the DJing on the weekends and stuff for this company, but I had my own system, and I made my own little business cards. People in school knew that I was a DJ, and so when they had birthday parties or sweet sixteens or barn bat mitzvahs, they’d come up to me and say, “Hey would you help me DJ, would you mind DJing my party?” I’d be like, sure. I wouldn’t charge a lot of money because they would call probably a real DJ company who wanted like $500, $1,000, and I would walk away with 150 bucks maybe. That was it, and I had a neighbor across the street that had a van, and I would pay him like 30 bucks to help me lag the equipment back and forth, and he was nice. That was it.

Jason Hennessey:

Back then, it was like so much equipment, like huge speakers and this, and setting up tape players and bringing all the tapes. That was the problem back in those days is the music was half the battle. You just can’t stream music. You had to have like a good music selection. People came up and they wanted to hear this song. If I didn’t have it, I didn’t have it, so you had to listen to what I had, I guess. Yeah.

Luke W Russell:

You’ve described yourself as a hopelessly distracted C student.

Jason Hennessey:

School did not come easy to me in the traditional sense of school where you need to kind of memorize and study and learn about things that I wasn’t necessarily interested in. I was doing a lot of daydreaming in class and thinking about being on the baseball field or I still got a bag of blow pops in my backpack, who can I sell these to? I had all these other kind of things kind of going on in the back of my head. When it came to school, I just wasn’t really … It just didn’t come naturally. I had to work really hard. I ended up kind of getting through junior high, I ended up getting through high school, but I wasn’t the kid that was getting a scholarship into an Ivy League School, instead, just the opposite.

Jason Hennessey:

I graduated high school with a Regents diploma, but because I didn’t have the financial means to go to college, I ended up joining the Air Force and, and that was gonna be my route to paying for college.

Luke W Russell:

Yeah. Did you get more were out of your time there than you were expecting?

Jason Hennessey:

In the Air Force, for one, it absolutely turned a boy into a man, like from the first day of bootcamp, because I wasn’t used to making my own bed, ironing my shirt and being disciplined to waking up at a certain time. Right away, it kind of taught me all of the life skills of what I was going to need if I was going to transition from, like I said, a boy adolescence to an adult. But once I graduated bootcamp and I got through tech school, now I was in the air force and people that were around me were planning on being in the air force for 20 years and retiring, and that was going to be their path. That wasn’t for me.

Jason Hennessey:

I was very money motivated, and because I didn’t have money growing up. I knew that the Air Force wasn’t going to be a long term thing for me, but I certainly value … I mean, a lot of the stuff that I do with my business, even today, like from recognition ceremonies, to how culture and organization and systems and processes, a lot of that I attribute to my days in the military because they were so structured. But I did four years and I got out and I just got more back into the entrepreneurial world where I belonged, I guess.

Luke W Russell:

When did you first start to realize that you like starting things?

Jason Hennessey:

That probably dates to even when I was like in middle school. My mom and my grandma would take me to like a Costco, or there was another place called BJ’s in New York that was kind of like a Costco. I saw as an opportunity where I’d walk down to the candy aisle and I’d want to buy some candy. And my grandma, my mom would buy me like this big bag of blow pops, and it might be like $10. I would selfishly eat a couple blow pops, but I would put them in my backpack and I would walk around school, and I was the blow pop kid. And if you wanted a blow pop, 25 cents. I was the kids selling blow pops when the kids would get like lunch change.

Jason Hennessey:

At that point, I guess, is when I started to think about starting, whether it was a business, or I didn’t know what to call it at that time, I was literally doing it because I didn’t have a lot of money. My mom wasn’t just giving me $20 every day. I had to kind of earn it if I wanted to buy a slice of pizza after school or something.

Luke W Russell:

Yeah. When you start looking at this in your middle high school years, what did you start to learn from these ventures that you would, I think that you feel like maybe laid the groundwork for your adult entrepreneurial career?

Jason Hennessey:

If you want something, you work hard for it. The money that you make, you need to reinvest and turn 25 cents into 75 cents and turn 75 cents into $1.50, and continue to kind of go down that path. Even till this day, that’s how I’ve always grown most of my businesses, is just kind of creating something out of nothing, putting in the sweat equity, and reinvesting the money into growing the whatever company it was, whether it was my blow pop company, to my DJ company, to now my digital marketing agency. I’ve never really been handed, here’s $500,000, go have fun with it and build a business. It’s always been kind of bootstrapped from the first dollar.

Luke W Russell:

Now, when did you start your e-commerce store?

Jason Hennessey:

I’d just gotten out of the Air Force. I was going to college at UNLV in Las Vegas. I had a DJ company where I was DJing weddings and parties and nightclubs, but the one thing that I could not tap into was brides that were coming to Vegas to get married as a destination wedding. I had this great idea, it’s still early on in the internet days and there wasn’t a lot of websites out there. My thought process was, what if I built a website called Vegas Wedding Mall? This could be a place where brides come and plan their wedding.

Jason Hennessey:

I paid a developer $5,000 to develop the website. After a month of having the site designed, I noticed that nobody was coming to the website. I’m like, what the heck’s going on here? I called up Stalin, he was developer, I’m like, “I think this site is broken.” And he goes, “Oh no, traffic.” He goes, “That’s something called like SEO or something. I don’t know anything about that.” At that point, I bought a book and I pick up the book and I read it twice and I just started practicing.

Jason Hennessey:

That was my first website. It was a site where brides can come plan their wedding and eventually it became a like an e-commerce store where you can buy wedding favors. That’s how I kind of taught myself this whole world that I’ve lived in for the past two decades.

Luke W Russell:

Any chance you still have that first book?

Jason Hennessey:

I haven it. I still do, man. It’s right behind me.

Luke W Russell:

I love that. Here we’ve come full circle 20 years later, and now we’re talking about Jason’s SEO book.

Jason Hennessey:

Yeah. It was by a guy by the name of Aaron Wall. He had a website called seobook.com, which was smart because that’s what he was selling. Then from there, he had a private mastermind group where we would pay like a couple hundred bucks a month to kind of teach each other things and learn from each other.

Luke W Russell:

Once you start digging in on the SEO side, how long was it for you to start seeing things pick up and start actually getting business out of that?

Jason Hennessey:

I had my DJ company, and so the DJ company was benefiting from this Vegas Wedding mall because we were the only DJ company listed on the website. We started all eventually, like I got so good at the SEO that I had photographers and florists that were finding the website on the internet and calling me up and wanting to know how much does it cost to advertise on this website. Then I even had like the Bellagio, I think at the time, that called me up, it was like the catering manager. This was really, I built this selfishly so I can get more DJ business.

Jason Hennessey:

When the catering manager of the Bellagio called me up, they were like, “Hey, we found this website, we did a search for Las Vegas wedding and it’s ranking, and how much does it cost to advertise on this?” I’m like, hmm, maybe there’s something here. I’m like, “Wait a second. You’re the Bellagio? I’m like, “Let’s just do this. I have a DJ company. Why don’t I give you a big banner and then you just put me on your list for recommended DJ vendors for your brides?” I was doing kind of barter arrangements and stuff like that.

Jason Hennessey:

But then it came to the point where I’m like, maybe a onto something here because next thing you know, I had people calling me, and I was just like, here, a hundred bucks a month, you can have a listing on the florist section or the limo section or whatever. It was very easy to just to build another category. Next thing you know, that site is making money just from people advertising. That inspired me to create Los Angeles Wedding Mall, and Seattle Wedding Mall, and Phoenix Wedding Mall. I started to create a bunch of those.

Jason Hennessey:

Eventually, that turned into a whole business and we had a call center and a tech team. Next thing you know, now I’m kind of like in the internet business and I wasn’t just a DJ company anymore.

Luke W Russell:

As things were growing, did it ever feel like things were growing at a pace that felt like it was out of control?

Jason Hennessey:

It did. In fact, that’s what killed the business, was we had a call center and we were hiring all these sales people. I’m not sure if you’ve ever ran a call center before, but these sales people, we had like 30 people in a room and they were doing this thing called dialing for dollars. They would call different wedding professionals. They’d call like a photographer in Phoenix and basically sell them advertising on this website. I was still new to business and I wasn’t monitoring everything that was being said, and people were just basically selling and promising the world.

Jason Hennessey:

When people were told that it’s $99, they might neglect to mention that it was not $99 total, it was for every month. So, things like that. It would cause all kinds of issues. We started to get some chargebacks and it started to kind of get outta control. The other thing about it too, was, I wish if I would’ve done that again, knowing what I know now about SEO, I wouldn’t have built 15 different websites. I would’ve built one website and kind of make it more of like a national wedding directory. We learn our lessons, I guess, in life.

Luke W Russell:

Yeah. When did that chapter come to a close?

Jason Hennessey:

That chapter came to a close when I had a partner, he was an old high school friend that I brought down to run this business because I had my DJ business too, and I couldn’t kind of run two businesses. We started to kind of … There was a lot of pressure because we were getting chargebacks and his responsibilities and I had responsibilities and we weren’t really seeing eye to eye too much anymore. Instead of selling the asset, we hired a business broker and the business broker ended up kind of connecting us with a guy that lived in Atlanta, Georgia that was interested in kind of, not buying the asset, but kind of helping to incubate something that could be bigger.

Jason Hennessey:

His name was Brad Fallon. We ended up going to Georgia. I lived there for a month without my family, kind of got to know all of this, and I’m like, okay, this is going to be cool. We packed up, we headed out to Georgia. Then while I was out in Georgia, Brad asked me to speak to a group of lawyers, and this is how I transition and I got into the legal space. I’m sitting there, I’m talking with Brad, and he’s like, “Hey, tomorrow I’m asked to speak to a group of DUI lawyers. It’s 50 DUI lawyers that don’t compete with each other and they come to learn about marketing.”

Jason Hennessey:

He goes, “I know a little bit about SEO, but you know a lot more, so what if I got up there and I gave a presentation, and I spoke for a couple minutes, and then you kind of came up and actually taught them something?” I’m like, “Okay, sounds good.” I’m like, “I don’t know nothing about law, but let me go put together presentation.” I went back home and I could not put together a presentation that was applicable to lawyers because I don’t know anything about that. I’m like, screw it. I only had like a couple hours to put something together. I’m like, I’m just going to teach them how I was able to rank number one on Google for the word, wedding favors.

Jason Hennessey:

And I’m just gonna be transparent and I’m going to show them exactly what I did. I got over there, and I said, “I apologize am not legal marketer per se, but I’m going to … It’s the same thing. It’s just different keywords. I’m going to show you everything that I did.” I started to give the presentation, and by the time I was done with it, I had about seven lawyers that came up to me, said, “This was amazing. Is this something that you do, is you do coaching or SEO for a lawyer?” I’m like, “Not really, but give me your card.”

Jason Hennessey:

That was kind of the genesis of the first agency that we built, because Brad’s two other employees, the writing was on the wall, there was not going to be a business. So, we ended up kind of partnering up and creating EverSpark Interactive, my first agency.

Luke W Russell:

Yeah. Chris was one of your business partners in EverSpark, is that right?

Jason Hennessey:

That’s right. You remember Chris, yeah.

Luke W Russell:

Yes, I do remember Chris. You two eventually parted ways. What preceded that?

Jason Hennessey:

With EverSpark Interactive, we ran that for about seven or eight years, and we built it up and it was great. Then there became a point where it was a two-headed dragon, right? Chris had ideas, I had ideas. My wife has been putting a lot of pressure on me to kind of get to the west coast again, to be closer to her family. My young son, Zach, just started to getting to acting and he had a manager that lived in LA. The world, the universe just started speaking, and Chris and I had breakfast one morning and we said, what do we think about buying me out?

Jason Hennessey:

We came to terms and it was a very amicable buyout. We’re still friends. Chris just kind of bought my interest, and we drove out to Hollywood and we were in LA now, and we didn’t even have a place to live, man. We literally like packed up two trucks, we drove them across country, and we were literally, we were going to stay in a VRBO. We were going to stay in a VRBO in the Hollywood Hills for a month, and then we were going to get acclimated.

Jason Hennessey:

We put our stuff in storage. Then from there, we stayed in another place in Los Feliz for another month. Then finally we found a place that we rented for like two years, because we still weren’t really familiar with the area. Then one client became two clients and two clients became three. Then, a guy by name, Alex Valencia, who you know, and Alex was like, “Hey, I’d love to work with you.” We ended up doing a partnership and together we kind of started to grow our businesses. He was doing the content, I was doing the SEO, and then, but they’re two separate companies, and we just kind of like helped each other grow.

Luke W Russell:

I want to go back to 1999, if I have the year right, can you marry someone you just met?

Jason Hennessey:

You wouldn’t think so, right? But my wife, Bridget and I, did it. We met on the day before Valentine’s Day, and I was going to the Oscar De La Hoya fight again. I was still in the Air Force, just got back from Italy. I was on my last year of my Air Force. Went to the shoe store to get some shoes because I had to look good for this fight. They gave us free tickets to go. My little spunky, cute girl was helping me buy my shoes. She asked me for myself phone number, but I didn’t have a cell phone number, and I had a beeper number. I gave her my beeper number, came home, I think the next day, because I got a random beep. I called back the number, it was her.

Jason Hennessey:

Then we went on our first date. I didn’t have a lot of money, Luke, so I was trying to like convince her to go to like a buffet or something, and she’s like, you want to take me to the buffet on our first date. We ended up going to the cheesecake factory, and I was hoping and praying that the credit card would go through because it was a debit card. But as far as getting married to somebody that you don’t know, so on April fool’s day, I came home and half jokingly, remember this is only like a month and a half later, half jokingly said, “Hey, let’s go get married.” And she half jokingly said, yes. We went down to the Justice of Peace with a witness, who was my buddy, Dan, and as we’re in there, I’m like, I can’t do this. What are we doing? This is crazy.

Jason Hennessey:

Then my buddy Dan’s like, “Come on, man. You didn’t make me drive all the way down here for nothing.” He’s like putting pressure on us. So, we went through with it. We were two little knucklehead kids that actually just went through it. It was a good decision because obviously we’re married now, 23 years later, and we’ve got three beautiful children. But in hindsight, I don’t think I would’ve done it that way because I didn’t have respect for her father, I didn’t ask for permission. There’s all of those things that I kind of would like to take back. Yeah.

Luke W Russell:

Yeah. I was curious when your wife, Bridget, shared that story with us. I was thinking like, okay, let’s say it’s 2034 in Brooklyn, your daughter is now 18, she meets someone, she comes home, and she says, “Dad, I’m going to marry this person.” Are you going to say, you can’t marry someone you just met?

Jason Hennessey:

I guess I can’t, man. I hope that I can teach her enough valuable lessons to make good decisions in life. And if she feels the spark and it is her soulmate and she makes the decision, I could only support it I guess, but leading up until that, yeah, she’s not allowed to have no boyfriends or anything. Yeah.

Luke W Russell:

Oh man. Do you think it’s fair to say that pranks are somehow embedded in your DNA?

Jason Hennessey:

Oh my God. It was definitely part of my DNA. You know what? I always tried to make people laugh. That was just my thing. I guess at an early age, I kind of saw that … I didn’t see this back then, but an early age, I guess there was negative energy and positive energy, and I chose to kind of choose positive energy, and the way in which I chose to bring the contagious positive energy was by trying to make people laugh. Sometimes the making people laugh came at some of my friends’ expense, by me pulling pranks on them.

Luke W Russell:

What would you say is the most spectacular prank you’ve ever pulled off?

Jason Hennessey:

I was working as a radio personality in Las Vegas. When you work as a radio personality, you get invited to all kinds of events, right? Like Blue Man Group, front row concerts, this, that, opening of new casinos, VIP treatment. It didn’t come as a surprise when I came home to my wife and said, “Hey, we got invited to go take a helicopter tour of the Grand Canyon.” But what she didn’t know is that it wasn’t going to be a helicopter tour of the Grand Canyon onion. It was, I was setting her up for a practical joke that was going to be possibly televised.

Jason Hennessey:

We got in the car and we started driving to like, we lived in Las Vegas, so you had to go out to, I think it was called Primm, Nevada, or something like that. It’s going towards California. The whole way there I’m kind of act being, and I’m telling her like, “Oh man, are you excited? This is great. I don’t know why I’m feeling kind of nervous. I’ve never been in a helicopter before. I almost feel like I have to use the bathroom. I don’t know what’s wrong, but my stomach is kind of churning.” And she’s like, “Are you okay?” And I’m like, “I don’t know, hopefully they got a bathroom when we get there and I’ll just go see if I have to go.”

Jason Hennessey:

Then we pull up and we park, and there’s a security guard, and they’re like, “Oh, you’re here for the helicopter tour.” We go over here and there’s two helicopters positioning. Then I get up there and they’re like, “Okay, great. Yeah, you guys are here. What’s your name? Bridget and Jason. Awesome.” So, they’re putting vest on us. Meanwhile, these vests have cameras and stuff, and Bridget doesn’t know. Then I asked the guy, I’m like, “Hey, by the way, can I use the bathroom?” I’m like, my stomach is not really feeling well.”

Jason Hennessey:

He’s like, “Oh yeah, sure. We don’t have a bathroom here, but there’s a porta potty right over there.” I’m like, okay, perfect. This is all fed up. I go, I walk into the porta potty, and my wife sees me get into the porta potty, and then as I get into the porta potty, the guy’s still talking to Bridget. This is when we first were married. I mean, we might have been like married for like a year, and I’m doing this. And so as I get into the porta potty, they open up like a back door and I get out of the porta potty and they put a construction outfit on me, so now I look like one of the construction guys that are on site doing some stuff.

Jason Hennessey:

As Bridget’s talking to the guy, the guy’s like, “Oh, by the way, this is a helicopter. It’s going to be leaving. It’s going to get loud here, so just kind of hold your ears for a second.” The helicopter starts to take off, and then Bridget’s looking at the helicopter. Then sure enough, there’s like a rope that’s attached from the helicopter to the porta potty. The helicopter takes off, the porta potty is attached to the helicopter and it starts flying in the air with the porta potty, and the porta potty’s swinging back and forth.

Jason Hennessey:

Then Bridget’s like, “Oh my God, my husband’s in the porta potty.” Just imagine what she’s thinking like, I’m in there taking a crap in this porta potty, and the helicopter takes off and it’s lifting me up, and I have no idea what’s going on. Meanwhile, I’m just like over to the side. The guy’s like messaging on the radio, he said, “You got to get that down.” Who connected the porta potty to the helicopter? Oh my God, you got to get that down. Her husband, this poor lady’s husband is in the porta potty.”

Jason Hennessey:

As she’s up there saying, what the heck’s going on, I can’t believe …” Then I come up to the side, and I’m like, “Gotcha,” whatever we said. She’s shocked and she’s like, “Oh my God, you effing idiot, effing this, and effing that, you asshole, blah, blah, blah. I think because she used so many bad words, they didn’t end up using like our video. Unfortunately, I don’t know if it ever aired, but yeah, that was probably like the biggest prank I ever pulled off in my life.

Luke W Russell:

When we come back, Jason will tell us how he made hundreds of thousands of dollars betting on sports boards and why he eventually walked away. Stay with us. I’m Luke W. Russell, and you are listening to Lawful Good.

Luke W Russell:

Season two is about powerful partnership. Interesting and caring folks that we know and trust whose journeys brought them to collaboration with the legal community. In our next episode, a business spotlight, Jason and I discuss what his company, Hennessey Digital, has to offer and if it’s something that would benefit you or someone you know. By highlighting companies like Hennessey Digital, we create an opportunity to help make Lawful Good possible, financially. As you probably can imagine, Lawful Good requires an enormous amount of resources to make happen.

Luke W Russell:

One way we’re making this show possible is by featuring people we know, like, and trust, many of whom we have a referral relationship with. After you finish up this episode, check out our business spotlight to learn more about Hennessey Digital and how they help attorneys thrive in their markets.

Luke W Russell:

When we left off, Jason was recounting his early business experiences and the joys of pranking his wife. As we pick up the conversation, we’ll hear about his experiences with gambling, what entrepreneurship means to him, and why he loves working with lawyers. I’d like to talk about gambling. Can we do that?

Jason Hennessey:

Sure. I’m a gambling man.

Luke W Russell:

Yeah. What was your first gambling activity?

Jason Hennessey:

Well, when you’re moved to Las Vegas at 18-years-old, I didn’t even really know … I guess I knew gambling existed, because my mom and my grandmother would play the lottery. You know what I mean? That was their thing. They would go play the lottery and hopefully become the millionaires, and that never happened. I guess I was around gambling as a kid, but when you take that and you put this 18-year-old kid in Las Vegas, now your whole world opens up to gambling. Because if you need to go to the movies or bowling or wherever, the Vegas is … Even if you go to the grocery store, there are slot machines, you know what I mean? Everywhere you look in Vegas is gambling. When I turned 21, I’d play a little bit of like blackjack.

Jason Hennessey:

I wasn’t really like a slot person, but I would play some blackjack. Then I met a guy by the name of Dave. He goes by the name Vegas Dave, now. He’s like a celebrity. He gives picks, and he’s pretty well-known. This guy Veg was kind of like a savant, like a football sports savant. He can tell you who the third string quarterback is and which high school he went to, and this, and that. He just has all this insight. Dave was like doing very well. He was driving a nice car and he had a lot of money and he wore nice watches and all this other stuff.

Jason Hennessey:

I bumped into Dave at like the sports book one day. We started talking and I was there just basically betting like $20 on a football game or whatever, just to kind of have some action. I just started seeing all this money and he would get a lot of the games right. I’m like, I’m going to follow him. I took out $10,000 out of an account that I probably didn’t even have at the time. I just followed everything that he did for like a whole football season, like beginning of football season to the end of the football season, and I would win.

Jason Hennessey:

I would bet big. Started out betting $2,000 a game, and that would turn into 5,000, and that would turn into 10,000. Next thing you know, I had a safe deposit box in the casino, the Suncoast Casino, where we lived in Summerlin with about $300,000 in cash.

Luke W Russell:

Wow.

Jason Hennessey:

In a safe deposit box. It was all from just following this one guy, Dave, and everything that he did. I’d go back home to New York and take my friends out to New York City, and we get limos, and we go to steak dinners, and I would just have wads of cash. As a 23-year-old kid with kids that are going to college, a community college and living with their parents, it’s like, who are you? Where did you get this money? I’m like, oh, I just kind of dabble in this sports book stuff. But then it started to take a toll on our relationship. I was out to dinner and we’d have like … It got to the point where I’d be betting like $50,000 on a football game.

Jason Hennessey:

Two teams that I knew nothing about, I’m just kind of following the advice. There’d be a lot of pressure, man, when you got that kind of money on a football game and you’re out to dinner with your wife and two young boys, and I’m looking out at my phone. It wasn’t like now what we’ve got, where it’s fast instantaneously, like you push a button and you wait and you wait, and then it kind of reveals. That was a lot of pressure. So, I wasn’t really like living in the moment with my family, man. It was a lot of pressure, and so my wife puts some pressure on me, and she’s like, “It’s either gambling or it’s me. I can’t do this anymore.” Obviously, you know what decision you make at that point.

Luke W Russell:

Yeah.

Jason Hennessey:

Yeah.

Luke W Russell:

Did you sense it was a problem before your wife told you that you had to pick?

Jason Hennessey:

Yeah. Like I wasn’t to the point, Luke, where I was going to like gamblers anonymous or anything like that, but it didn’t get bad, man, like lose a game I didn’t want to go back and put money on the game to win the money that I lost. You know what I mean? It’s certainly is a vice for sure. The kids were young. They were probably like five and three, maybe something like that. I quickly realized, man, I’m sitting here sweating this football game out right now when I should be home with my wife and my kids, and what am I doing here?

Jason Hennessey:

Even if all the money in the world isn’t really worth it when you look at it like that, I just kind of stopped. I just stopped doing it. Could I have been another Vegas Dave with millions and millions of … Sure. I was winning. It wasn’t that I was losing. He owns like two compounds in Cabo, and he’s got Bentleys, and Ferraris, and Bugattis. I mean, he’s still really good, but for me, I went the route of having a family and being a loving husband and a loving father, and kind of going all in on that.

Luke W Russell:

Yeah. Is there anything you hope for your kids to take away from your own journey?

Jason Hennessey:

Yeah, through stories like this, I hope that they learn from the lessons that my wife and I, both, have experienced, but also when they come to visit me in my old age home when I’m 93, that I am the coolest guy in the old age home dude. I want to tell the story of how I would walk around with $10,000 and we’d go on shopping sprees because of my gambling, and I want to tell about that I owned a Lamborghini, and I want all the people at the nursing home to be like, “He’s just making stories up. He didn’t own a Lamborghini. Don’t listen to him.” Just like I do with SEO, I reverse engineer, so I’m reverse engineering me at the nursing home, being the coolest guy at the nursing home, man.

Luke W Russell:

I love that. Okay. Jason, Hennessey Digital.

Jason Hennessey:

Yes.

Luke W Russell:

When we asked your brother, Vincent, what it was like working for you, he said, quote, “It was actually really cool.”

Jason Hennessey:

Yeah. He came in as an intern when he was only like 16-years-old and we would kind of give him odd jobs. In fact, he didn’t start working at Hennessey Digital. He was working at EverSpark Interactive in Georgia. He kind of came in and he learned entrepreneurship and business and being assigned some of the crappy jobs that you get as an intern but working your way up. But I think, in the end, it was just kind of getting the experience of seeing what it’s like to build the business and run a business and have me as, more of like a mentor.

Jason Hennessey:

Because we didn’t really come from a family of entrepreneurs. I was just kinda making it up as I was going, and I think I had some pretty good business acumen and I was making some of the right decisions, so he was seeing some of that. But yeah, I think he learned a lot and now he’s a young entrepreneur himself and kind of building his own businesses.

Luke W Russell:

Wow. That’s really cool. Do you have certain tendencies that get in the way of being a good boss or leader?

Jason Hennessey:

Yeah. I try to, and I don’t know if it’s bad or good, I’m not like the jerk boss, down somebody’s throat and putting pressure on people. That’s one way, I guess, to kind of be a leader. I guess I’m more of kind of like the nice friend boss, and while most people respect that, there are some that might take advantage of that too. That’s why it’s important for me to put good leadership in place that helps me to inspect what you expect with business, but also do it in a way that it doesn’t kill culture.

Luke W Russell:

Tell me more about that.

Jason Hennessey:

Well, culture is so critical to just any business, and when you’re a young entrepreneur and you’re just kind of building business, you’re not kind of thinking about that. You’re just trying to kind of get more sales and manage clients and sell a new client and try to bring in revenue, and make sure everybody’s getting paid on time. But once you start to build a company and there’s more than 15 people, and there’s 30 people, and there’s 60 people, culture is a big part of that. I got people that were more experienced at building companies and culture from, I’ve got an executive coach that helped me to see that, to bringing in a president and the COO, to bring in a CFO, to bringing in a director of people success.

Jason Hennessey:

To bringing in people that their main job is to help build the culture of the company. By having good culture, you keep happy employees. By having happy employees, you have happy clients. That’s one of the secrets of of business.

Luke W Russell:

One of the things I’m hearing from you is like a lack of ego and needing to know how to do everything and needing to know, like making the culture about you versus making it about, it sounds like, about the team and the whole.

Jason Hennessey:

You have to put ego aside, for sure. The other thing that you have to do is you have to recognize that, back when I first started the business, I was a control freak. I had to make sure that I knew who was getting charged what, and how much I was paying everybody, and what does it say on this job description? Anyway, I was kind of like a control freak. But once you start to recognize that you need to kind of get out of your own way, if you really want to grow a business and you need to put people that are more capable in specific roles, that’s when you start to really start to see business accelerate and grow.

Jason Hennessey:

That was a big lesson for me because I was trying to do everything, and I was doing a pretty decent job at it, but I was working around the clock and it wasn’t healthy. At some point, I wasn’t even having fun anymore, because I was working so hard doing things that I wasn’t even really good at. I made a pretty significant investment into building an executive leadership team. From there, we built layered managements and we put better systems in place, and processes in place. Heck, I wouldn’t even probably be able to have this call with you three years ago, because I would have conflicts with client calls and sales calls and making sure payroll was paid. Now I get to kind of do some of the stuff that I enjoy, like having these kind of conversations.

Luke W Russell:

Yeah. What is your responsibility to your employees?

Jason Hennessey:

To make sure that we help people live a happy life, both professionally and personally, doing something that hopefully they enjoy, that they look forward to, and being a part of their families and stuff. We’ve got a gratitude channel on our slack, and so people post what they’re grateful for. We’ve got a recognition part of our channel, where if you’re living some of the core values of the company, you get recognized for that. Basically helping to build each other up and support each other, both personally and professionally.

Jason Hennessey:

The money side of it, that’s just a tool. That’s just a tool in life, right. We all have to kind of eat, we have to have a roof over our head, but I think there’s a lot more to keeping employees happy with other aspects of what their purpose is.

Luke W Russell:

Yeah. What’s a serial entrepreneur, and are you one?

Jason Hennessey:

Yeah, a serial entrepreneur is someone who will start a business, start to grow it, new opportunities start to surface and they see the opportunities and they start to act upon it. It’s both good and bad because sometimes serial entrepreneurs, if they’re laser focused on building one business, that one business really starts to grow, but in some cases, serial entrepreneurs start to diversify their time and their resources, and the next thing you know, you’ve got three businesses that are leveraging some of the same resources and they’re all starting to kind of grow, but not as quickly.

Jason Hennessey:

Then sometimes there’s distractions. What seems like a good opportunity ends up being a distraction. That one distraction starts to slow down the growth of the other three companies. The good thing that I have is I’ve got a president and COO who is kind of my know guy. So, he helps me to weigh some of these opportunities and helps me to see that the opportunity might not be as great as I’m envisioning it, and starts to slow me down and keep me focused little bit. Yeah. I’m certainly a serial entrepreneur and I’ve got multiple businesses, but if I didn’t have him, I probably would have multiple dozens of businesses, and who knows where I’d be.

Luke W Russell:

Yeah. Is there a difference between being a business owner and being an entrepreneur?

Jason Hennessey:

Yes. A business owner could certainly be you taking over your family’s business. You just kind of grew up working at your family’s restaurant, and that’s what you kind of know, and now you just own the business. You didn’t start the business. You didn’t try to get $2 and turn $2 into $10, and $10 into a 100. I think there is a difference, but I think nature and nurture. If you grow up around that, the DNA, over the course of nurture, like you’re taught how to be an entrepreneur and how to have better business acumen and how to make good business decisions. But right from the nature side, you can tell people that are born with that skill and that gift. There’s definitely a difference.

Luke W Russell:

Yeah. Your new website says that you are “self-taught and self-made.” What does that mean to you?

Jason Hennessey:

I ended up learning a skill that was not necessarily taught in college. I know people can’t see the visuals right now, but there’s a bookshelf behind me, and the first two rows are really like SEO and digital marketing books. I really kind of went 150% into this new skill. I just taught myself this, and it’s not something like I couldn’t have went to Yale or Harvard or some of the most prestigious universities and learn what I’ve learned. I just had to pay my dues and time my own personal time. That’s what I mean by self-taught, how is, I guess, what is referred to as an autodidact.

Jason Hennessey:

As far as self-made, there’s something that’s comes across as egotistical about that, and it’s certainly, that’s not what I mean. Self-made is really, kind of from my humble beginnings. Nobody gave me, like here’s $10,000 to go start your first business. I didn’t have any loans. In fact, I had to pay for my own college by sacrificing my time in the Air Force just to kind of get my education. The self-made piece is really just kind of taking what I was given or what I decided to work hard for and continuing to reinvest into, I guess what I’ve built over the years.

Luke W Russell:

Yeah. I want to steal a bit of one of Tim Ferriss’s questions that he used in his book, Tribe of Mentors. Do you have a favorite failure of yours when you look back and you see how that maybe set you up for later success?

Jason Hennessey:

There’s a lot. But the one that comes to mind, let’s just say it was a decision that I probably wouldn’t have made. When I was just out, I was still in the air force, I was working at as a part-time pizza delivery driver to make extra money because you didn’t make a lot of money in the Air Force as a young airman. I was starting to build my DJ company, because I started to build my DJ company while I was in the Air Force. I’ll never forget it, man, I ended up meeting with a rep from the Yellow Pages. This rep met me at the pizza place, and I was kind of like in between delivering pizzas and I’m sitting with him, and he’s like, “So yeah, the Yellow Pages could bring a lot of business to you.”

Jason Hennessey:

“Why don’t you think about, you could either do a full page ad, which is like $1,200, or you can do a half page ad, which is $600, or you can do like a business card ad under the DJ section for $300.” I’m like, “Okay. Well, I don’t have $1,200, I don’t have $600. Let’s do the one for $300.” And he’s like, okay. And signed all the paperwork and everything. Then the book was going to come out in a couple months, but they charged my debit card. I might’ve had like 500 bucks in the account, and next thing you know, bam $300 comes out, so it leaves like $200 in the account.

Jason Hennessey:

I’m like, okay, that’s cool. The next month comes by and I go to my bank account, and it’s like an overdraft. I’m like, what the heck happened? Then I look and there was like $300 was taken out again by the Yellow Page company, and then I’m like, what the heck? I call up the guy and I’m like, “Hey, I just want to let you know, you guys charged me last month, but you accidentally charged me again and put my account into overdraft.”

Jason Hennessey:

He goes, “Oh no, you signed a contract. This is a monthly commitment.” I’m like, “I can’t afford this. What are you talking about? Blah, blah, blah.” The book came out, and this was back when people actually used the Yellow Pages, and people actually started to call my phone. I had to understand that I was going to have to pay this $300 every month, even though I knew I couldn’t afford it. But the book came out and my phone started to ring, and I ended up starting to kind of take calls, and I learned a lot of lessons along the way of how to take the call and making sure that I asked the right questions and put together a proposal and send out a package.

Jason Hennessey:

But it turned out that, that was one of the best mistakes that I’ve made, I guess. I don’t know if it’s the best failure, I guess, to answer your question, but that was one of the best mistakes that I made. It was a failure because my bank account was in overdraft, I guess, but that’s what got me to start to think about advertising, and you have to invest money to make money. I ended up making a lot more. Eventually, I was like the biggest ad in the Yellow Pages and so it worked out well, but I don’t know if I would’ve done that, Luke, if I knew that it was going to be every month because I couldn’t afford it. You know what I mean?

Luke W Russell:

Right. You came from deejaying and doing weddings and transitioned over to the agency world and found yourself working with lawyers. Now you’ve been working in the legal agency world for what? Around a decade now?

Jason Hennessey:

Yeah, since 2008.

Luke W Russell:

Yeah. What do you love about working with lawyers?

Jason Hennessey:

Oh, for one, doing what I do with digital marketing SEO, we all know that legal marketing is one of the most competitive spaces to enter, and so me being a very competitive person, I accepted that challenge and started to get some pretty good results and leveraged the good results and created a business as a result of it. But then the other side of the coin is the people in the industry. Here you are, you’ve got some very intelligent and savvy people that understand, not only the laws of our country, but also some pretty savvy marketers.

Jason Hennessey:

I would say, being a marketer, I appreciate some of the guests that you’ve had, I know you had John Morgan on. Talk about a savvy marketer and a savvy business guy. Dealing with people like that, that think big and take the risks that I didn’t mean to take with my Yellow Page story. But it’s cool to kind of be around that world. The other side too, is seeing what they do for people. Because lawyers are seen as ambulance chasers, and this and that, and for profit, but at the end of the day, when you look at lawyers and what they stand for, like Ben Crump, I know you’ve had him on the show, what they truly stand for and making an impact in the world, and that also inspires me.

Luke W Russell:

Yeah. Okay, Jason, I want us to transition over to our high velocity round, and this is where I’m going to ask you about six, eight or so questions. They’re all yes or no questions. The only rule is you’re not allowed to just answer yes or no. That sound good?

Jason Hennessey:

Okay.

Luke W Russell:

Okay. Will you ever stop pranking your wife?

Jason Hennessey:

Absolutely not. Will be doing that till the day I die.

Luke W Russell:

Does everything you touch turn to gold?

Jason Hennessey:

Some say I have the mightiest touch, but I’ve got some failures that aren’t necessarily publicized.

Luke W Russell:

Would you strangle me if I made a mess of your desk?

Jason Hennessey:

Yeah, I would not be able to work if you came in and make a mess on my desk. I’m so OCD.

Luke W Russell:

Do you still have your old CD collection?

Jason Hennessey:

I do, and I’m so fearful of, even though I’ll never use it again, I’ve spent so much money building it that I just can’t part with it, man.

Luke W Russell:

Has Brooklyn, your daughter, ever offered you an Oreo with toothpaste in it?

Jason Hennessey:

Oh my God, my daughter is such a little prankster and yes. And even though that I knew there was toothpaste in that Oreo, you bet your butt I took a bite of it, and then I got her reaction.

Luke W Russell:

I love it. Is Fendi better than Chanel.

Jason Hennessey:

That’s a better question for my wife, man. She would probably say no, I think she likes Chanel better.

Luke W Russell:

Are spreadsheets amazing.

Jason Hennessey:

Yes. Although I am certainly not as spreadsheet guru, but I love getting reports on spreadsheets and they make my life a lot easier.

Luke W Russell:

Are you well-rounded?

Jason Hennessey:

I think now I am. 20 years ago, I certainly wasn’t.

Luke W Russell:

Are you a better cook than your wife?

Jason Hennessey:

I think she would agree that I’m a better cook than her, especially when it comes to Italian food.

Luke W Russell:

And can you be happy if the people around you aren’t?

Jason Hennessey:

Absolutely not. If you’re happy and the people around you aren’t, there’s probably a high likelihood that you’re faking your happiness.

Luke W Russell:

Jason, are you naturally independent, or did your father, leaving at a young age, push you more toward that?

Jason Hennessey:

I think I’m naturally independent as a result of not having a whole lot of people to depend on.

Luke W Russell:

Do you find it hard or easy to be vulnerable?

Jason Hennessey:

Up until my 40s, I was not vulnerable at all, man. I always try to paint the brighter part of every story, but in life, you come across as more authentic when you’re vulnerable and people appreciate that.

Luke W Russell:

What shifted for you in your 40s that you started to lean in and embrace vulnerability,

Jason Hennessey:

Being around other people that were vulnerable and seeing how I responded to them and the respect that I had for others when you make your mess your message again, I wish I would have been more vulnerable in my teens. I kept everything to myself and it builds up, and builds up, and it builds up, and eventually, you just … The pressure becomes too much. It helps, in life, you have to breathe in and then you breathe out. That’s how we live our life. And you can’t really get very far if you’re constantly just kind of breathing in, but not breathing out.

Luke W Russell:

Yeah. How do you intentionally cultivate your relationships?

Jason Hennessey:

I Guess like this, like what we’re doing now, just building deeper relationships and really getting to know people, asking all of the right questions and doing things for people to see them succeed without having your handout for anything. I think that’s key, but I think the biggest thing is just continuing to strengthen relationships with those in which that you’ve already invested time, kind of building your friendship with.

Luke W Russell:

Your brother said of you, quote, “He’s my role model.” Do you feel a weight with others watching and looking up to you?

Jason Hennessey:

Oh, absolutely, especially my kids. I think that’s basically my purpose, at least is, not only providing for them, but giving them all of the tools that they’re going to need in this game called life. So, making sure that they have lots of great lessons that they learned from me, lots of great memories that they shared with me and my wife. And that when I’m long gone, that, through that, I also give them indirectly the tools that they need to pass on to their children.

Luke W Russell:

Yeah. By the way, when we did speak to your brother, Vincent, we asked him if there was anything we should ask you, and he was curious, what do you think about your brother Vincent?

Jason Hennessey:

Yeah, I think my brother, Vincent, is very contagious with positive energy, for sure. I mean, everybody loves Vincent. He’s very likable. He always sees the good in others. It’s rare that you ever see him kind of in a bad mood or talking negative about anybody else. He inspires me with the way in which he kind of conducts his life and some of the relationships that he has. It’s fun to kind of see him building businesses through some of the experiences and I guess with me as a role model.

Luke W Russell:

Yeah. As you mentioned, you have three children, two boys that are older and a younger daughter. What inspired you to have your daughter later in life?

Jason Hennessey:

We had the two boys and we thought we were done. Then we moved to California, and I think, for a while, we were thinking about having another one, but it wasn’t necessarily like planned. I’ll never forget it. My wife was having like some issues and we went to a doctor. She was actually going to have a procedure done. They went in and they’re like, “All right, well, we just need to take a pregnancy test, just … Then my wife’s like, “Oh, there’s no way I’m pregnant.” Then they’re like, “Well, we just need to do that.”

Jason Hennessey:

They go and take the test. I’m sitting in the lobby waiting for her. I guess they’re telling her like, “Well, something’s wrong, I’m seeing you’re pregnant.” She’s like, “There’s no way I’m pregnant. Maybe take the test again.” So, okay, let’s take the test again. They go take the test again. They’re like, “I don’t know. This one’s saying positive too.” Then she’s like, “Oh my God.” It was like 15 minutes into it, and they’re like, “Hey, it’s going to be an hour and a half. Please sit out here.”

Jason Hennessey:

Then 15 minutes, they come and get me. I’m thinking like, oh my God, what happened? You know what I mean? Why are they coming … And they’re like, “We need you to come to the back. I can’t tell you right now.” I’m thinking, what’s going on? They go back and they’re like, “You’re going to be a father again.” I’m like, “What?” “So, we can’t do the procedure.” It wasn’t really expected, but it was such a blessing.

Luke W Russell:

Yeah. What have you seen in your two boys and in their relationship with Brooklyn, your daughter, what have you seen in them that you look at and you just go like, wow, despite all the odds, me and Bridget, my wife, we created this?

Jason Hennessey:

Yeah. The boys are … They’re great, big brothers. Sometimes they really surprised me. A couple of things that I could really recall is, like my daughter went through the whole princess phase, and so she would love to get into her princess dresses. Then one day I came home, and both Zach and JJ are wearing like princess dresses, and so was Brooklyn, and they’re just playing with her, and I’m like, I love this. That was so magical. And other things too, like my son, Zach and JJ, they don’t have a lot of money in their account.

Jason Hennessey:

They’re working odd jobs here and there. Brooklyn just had her fifth birthday party, and Zach went to Tiffany necklace and bought her like a blue box with a little $200 necklace with his own money. You know what I mean? For his little sister, and JJ bought her a nice pair of boots that he really couldn’t afford either. They love their sister, and boy, does she look up to them.

Luke W Russell:

I love it. How old are you, Jason?

Jason Hennessey:

43 now.

Luke W Russell:

Do you have a particular age you want to retire by?

Jason Hennessey:

I don’t know if I’ll ever retire, because I guess once you retire, you’re like, your mind retires. But I do want to travel a lot. I think, probably when I turn 55, I don’t know if I’ll sell all of my businesses or anything like that, but I might put people in place to kind of run it and I’ll probably spend more time just as maybe like on the board. Maybe they give me a little desk I could come to every once in a while, and I would probably be tuning in remotely via Zoom or something.

Luke W Russell:

Yeah. When you think about where you are in life with your family, your businesses, how you’ve grown as an individual, what do you think your grandparents would be proud of?

Jason Hennessey:

I think they’ll be most proud of, not even so much the business success or whatever financial success that you can kind of deem successful, I think they’ll be most proud of, if we’re on that subway and an elderly person walks in and the subway is full, and my son JJ gets up and tells the lady to sit down, I think that would make them most proud.

Luke W Russell:

Yeah. How has your perspective on success shifted?

Jason Hennessey:

Success was 100% defined financially when I was, from 18 years old to I was 30, 35, that was how … Because that’s how society defines success. But I think, at the root of it, everybody kind of defined success differently. Somebody that has cancer that ends up beating cancer, that’s the biggest success that you can ever get. For me, I define success based on my children and the relationship that my wife and I have with our children, and providing for them and making their life a little bit easier than my life has been, but that’s dangerous too. But I base my success based on their success.

Luke W Russell:

Okay, Jason, it’s your 80th birthday celebration. People from all throughout your life are present. A gentle clinking on glass can be heard and a hush washes over the room. People raise their glasses to toast to you. What are three things you would want them to say about you?

Jason Hennessey:

For one, I hope there’s a lot of laughter from all the jokes that I played on everybody in the room. If I like you, I certainly have went out … I will go out of my way to play jokes on people. I hope there’s a lot of laughter from that. The second thing is really helping to foster so many different people’s careers, whether or not it’s just offering them employment or coaching or training or inspiration. I guess being a connection to wherever they are in life, both personally and professionally through friendships, mentorship, whatever. Then the biggest thing is that people look at me as a good role model husband and father to my children.

Luke W Russell:

To learn more about Jason, visit hennessey.com. That’s H-E-N-N-E-S-S-E-Y.com, and be sure to check out our business spotlight conversation, which is available as the next episode. Thanks so much for listening to us this week. This podcast is produced by Kirsten Stock, edited by Kendall Perkinson, and mastered by Guido Bertolini. A special thanks to the companies that make this project possible, Russell Media and The SEO Police. You can learn more about these groups by visiting our website, lawfulgoodpodcast.com. I’m your host, Luke W. Russell, and you’ve been listening to Lawful Good.