#29 – In Between Songs: Gregg Russell Is Happy In Harbour Town

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If you grew up in the South, you’ve probably heard Gregg Russell sing. If you were lucky enough to vacation on Hilton Head Island, South Carolina, you’ve probably heard it live. He’s been singing for kids and their families in Harbour Town under a 300-year-old oak tree since 1977. Two of those kids grew up and made a movie about him. The Gregg Russell Story became the #1 trending documentary on Apple TV earlier this summer.

After nearly 50 years of lugging his guitar all over the world as a singer, actor, and entertainer, Gregg considers himself semi-retired. He still loves to perform, but now he has more control over when and where. He’s carved out more time to spend time with family, write children’s books, and even a real estate side business.

Gregg is definitely known for his music, but as he told me, he made his living in between the songs. And even if that set list is a bit shorter these days, he still hits all the right notes.

Read The Full Transcript From This Episode

(click below to expand and read the full interview)

  • Greg Russell [00:00:00]:
    We always say when. Well, when the kids go away or when I don’t have to go to work every day, or when, you know, I get this windfall or whatever. You have to make things happen in your life. You have to be proactive, have a plan, have goals, follow the plan and structure your life financially, emotionally, and every other way so that when you get to the point where you can make a decision to transition into whatever is next for you, you have the ability to do that.Ryan Doolittle [00:00:35]:
    Do you ever wonder who you’ll be and what you’ll do after your career is over? Wouldn’t it be nice to hear stories from people who figured it out, who are thriving in retirement? I’m Ryan Doolittle. After working with the retire sooner team for years and researching and writing about how they structure their lifestyles, I know there’s more to be learned, so I’m going straight to the source and taking you with me. My mission with the Happiest Retirees podcast is to inspire 1 million families to find happiness in retirement. I want to learn how to live an exceptional life from people who do it every day. Let’s get started. Greg Russell, the legend. Thank you so much for coming on the show.Greg Russell [00:01:18]:
    I don’t know about legend, but thank you.Ryan Doolittle [00:01:21]:
    Yeah. Oh, wow. Okay, so as we’ve talked about a little bit before here, some of the people on our team are super excited to have you on the show, and I am as well. So we can’t thank you enough for sharing your time. I know it’s a precious commodity.

    Greg Russell [00:01:36]:
    Well, you know, I work almost 6 hours a week, so, you know, I’m pretty busy guy here.

    Ryan Doolittle [00:01:42]:
    Dang, if only I were as talented as you, I could have that schedule.

    Greg Russell [00:01:47]:
    Well, Ryan is not talent. It’s courage. That’s all it is.

    Ryan Doolittle [00:01:51]:
    Okay. I need that, too. Okay, well, just so I’m sure most of our listeners already know, but you’ve been writing and performing music for over 40 years. You’ve done hundreds of children’s songs. You’ve written for original music, for tv specials and more. And I think you’re probably best known for your evening concert performances under the old Liberty tree in harbor town, which is Hilton head, South Carolina.

    Greg Russell [00:02:18]:
    Yes. So, you know, I’ve had almost a 50 year career doing everything from ski resorts in Colorado every winter, like Vale and Aspen and Beaver Creek and those places. Over a thousand cruise ships from Australia to the Mediterranean, Disney world, Universal Studios, college shows, corporate things. But it seems that my time under the big liberty Oak and harbor town is how most people identify me?

    Ryan Doolittle [00:02:48]:
    How did that come to be? I mean, you. You were already a good musician, and how did it land you there?

    Greg Russell [00:02:55]:
    Well, still not a good musician. I know three and a half chords, but that’s. That’s enough. Believe me.

    Ryan Doolittle [00:03:02]:
    Okay.

    Greg Russell [00:03:03]:
    I was. I was in school in Florida. I was in college. I was playing around, knocking around little college bars and stuff. And I got up the courage to go audition at Disneyland. So I auditioned. There was this famous entertainment director guy there, a guy named Sonny Anderson. And I auditioned for him, and he told me if I’d cut my hair and shaved my beard and changed my name, he would hire me.

    Greg Russell [00:03:29]:
    So I got hired, and I would traditionally work at Disney on weekends and stuff. And then I got ready to finish school, and I didn’t really have a job or anywhere to go. A couple of weeks before I was finishing up, a guy walked up to me at Disney World and said, hey, I booked these entertainment venues up and down the east coast. I have a two week job on a place called Hilton Head Island, South Carolina. Would you like to have that job? Well, I had nowhere else to go, so I said, sure. So I finally found it on a map that there weren’t even really. It wasn’t identified on maps back then. And I came here for two weeks, and they asked me to stay for two more and two more, and that was 47 summers ago.

    Ryan Doolittle [00:04:19]:
    So 47 years of two week gigs. That’s.

    Greg Russell [00:04:23]:
    Well, it turned out to be 100 nights a year, basically, for the last 47 years. You know, I’m here a few weeks in the spring during our golf tournament on Cb’s and spring breaks and that sort of stuff. And then I’m here basically memorial day, Labor Day.

    Ryan Doolittle [00:04:40]:
    Is that where you are right now? You’re in?

    Greg Russell [00:04:42]:
    Yeah, I’m home. We have, I don’t know, this week and then next weekend, Labor Day weekend, and then I’m done for the season. We do a Thanksgiving show and a Christmas show. But other than that, yeah, I’m unemployed again starting next week.

    Ryan Doolittle [00:04:57]:
    Well, just some people are watching this and some people are listening. But for those watching what’s. What’s behind you there? Is that.

    Greg Russell [00:05:04]:
    Is that like, this is. This is our home. I guess up north they would call that a pond. Here we call it a lagoon. Okay. We have a nice big backyard, and we have alligators and eagles and osprey and herons and deer. All the deer come out at night. So it’s.

    Greg Russell [00:05:22]:
    It’s a very quiet, lovely little, you know, Hilton Head is a twelve by five mile Long island. Second largest barrier island on the east coast behind Long island in New York. Wow. But they have 40 million people and we have, I don’t know, 25,000 or something. And then in the summer, of course, people come on vacations and we are jam full all summer long. Almost at 100% occupancy for home rentals and villas and condos and hotels.

    Ryan Doolittle [00:05:56]:
    Oh, okay. So I’m from the west coast, so my only sort of, you know, the reason I knew Hilton head was Michael Jordan golfs there a lot or something, right?

    Greg Russell [00:06:07]:
    Yeah, he had a home here for years and years. His mom actually lived here for probably 20 years.

    Ryan Doolittle [00:06:13]:
    Oh, okay. Okay. So you’d see him around, maybe see him.

    Greg Russell [00:06:17]:
    You know, we have a lot of celebs here that come very quietly to spend family time. You know, we’re. We’re in a good location here with good accessibility of Savannah and Charleston. And even during COVID families could drive here from Cincinnati and Charlotte and, you know, feel safe and in our little bubble here.

    Ryan Doolittle [00:06:38]:
    Yeah.

    Greg Russell [00:06:38]:
    So, yeah, we’ve got a lot of celebs. I had a couple at my show last night and I won’t say who they were, but you would immediately recognize them and they’re just there being mom and dad with their kids. Really?

    Ryan Doolittle [00:06:52]:
    So that. No fanfare, just in the crowd watching the show.

    Greg Russell [00:06:55]:
    Yeah, we don’t point them out and make a big deal out of them and we respect their privacy. And I’ve spent an awful lot of time in LA and they always make sure the photographers are there to show them going to the ivy or whatever, but that doesn’t happen here.

    Ryan Doolittle [00:07:14]:
    Yeah, it seems like it’d be a nicer environment there than having a camera at your dentist’s office or something.

    Greg Russell [00:07:21]:
    You know, we forget the people who are famous and up. I’ve been lucky to be around a lot of famous people. They’re famous all day, every day, everywhere they go. And you hear for the first time through the 20,000th time. I don’t mean to bother you, but they’re just people that happen to be high profile and yet they want to live sometimes a little more quiet life.

    Ryan Doolittle [00:07:49]:
    Yeah, for sure. Yeah. I interviewed someone who works at the Santa Barbara zoo and he takes people on a train ride, you know, around the animals.

    Greg Russell [00:07:58]:
    Yeah.

    Ryan Doolittle [00:07:58]:
    And he was telling me he had had a couple celebrities on the train and it was kind of a similar thing. They were just mom and dad. Of course, people. People asked for pictures. Cause it was, you know, does anyone ever try to get on stage with you and sing any of the. Like, I’m sure you’ve got some musicians in the crowd.

    Greg Russell [00:08:14]:
    Well, I, you know, I have some very good Nashville friends who have homes here or come here on vacation. One of my best friends in the world is a guy named Jay DeMarcus, who is the musical genius behind the country group Rascal Flats. Really, you know, 22 number one hits and the most awarded country group of all time. And Jay has a home here, and his kids are now to the age where when they started with me, they were like four years old, five years old. Now they’re like these incredibly talented teenagers. So in years past, Jay would come up and sing some rascal flat songs, which people went crazy for. But now he wants to come up and play guitar for his kids to sing, you know, which is kind of cool, I wonder.

    Ryan Doolittle [00:09:03]:
    And his kids are probably the. The hardest people for him to impress.

    Greg Russell [00:09:08]:
    Well, you know, you know, and it’s funny, I said to him the other day, I saw him a couple of weeks ago, I said, joe, you’re lucky. Talent usually skips a generation. And in your case, it did.

    Ryan Doolittle [00:09:22]:
    Yeah, exactly. Okay. Well, and speaking of celebrities, just to. Not to get too off track, but you are now. I mean, you’re kind of a celebrity, and you’ve actually. Well, you’ve been in the movies, right? You were in. You had your own movie called Come Away home, right?

    Greg Russell [00:09:42]:
    Yeah, we’ve done a couple of movies that did quite well, you know, family oriented kind of things. And, you know, I’ve been in some other higher profile stuff. And, of course, recently, you may know that Apple TV has been running a documentary all summer long on what we’ve been doing there in harbor town for all these years. And, yeah, I. That has really stepped up my email messages from people around the country, I bet.

    Ryan Doolittle [00:10:13]:
    Yeah. In fact, thanks for fitting me in. I’m sure you were fielding calls.

    Greg Russell [00:10:19]:
    Actually, I just had a desk delivered, so I’m glad it was. The timing was perfect.

    Ryan Doolittle [00:10:25]:
    Oh, great.

    Greg Russell [00:10:26]:
    That’s my big day. Somebody shows up at the front door.

    Ryan Doolittle [00:10:30]:
    It’s a big day. Yes. Wait, so your first movie was Camp Tangle foot? Was that.

    Greg Russell [00:10:36]:
    Yeah, that was a little straight to video piece out of Nashville. Kim Dawson was the producer on that. He did teenage Mutant Ninja Turtles.

    Ryan Doolittle [00:10:44]:
    Oh, great.

    Greg Russell [00:10:45]:
    He was the guy that brought back the Mickey Mouse club, and he discovered, found Justin Timberlake and Britney Spears, you know, that whole cast. And Kim and I became very, very good friends, and he wanted to do a little, little piece with me. So we rented out a camp up in North Carolina, and of course, I played the camp director, and it was about little kids, you know, going away to camp for the first time, and it was just a sweet little thing. And then we did come away home with some high profile people that we shot here on hill. Ned, that did. Did quite well, and it’s in its time, and that was a lot of fun. And now the apple tv thing. But I.

    Greg Russell [00:11:28]:
    I’m not really an actor. I got to be myself, which helps, but I’m not really a trained actor. I have a daughter who is incredibly trained actor. Oh, really? Yeah. She’s in New York and went away to a performing arts boarding school up in Michigan called interlocking. A lot of famous people came out of there. She went straight to New York to college for four years and studied. Talk about talent.

    Greg Russell [00:11:55]:
    Skipping a generation. That’s what happens.

    Ryan Doolittle [00:11:59]:
    You’re saying it skipped you and went to her?

    Greg Russell [00:12:01]:
    Absolutely. I have faked my way through this whole thing, brother.

    Ryan Doolittle [00:12:07]:
    Well, you know, should we be looking for her in some upcoming projects or.

    Greg Russell [00:12:12]:
    Well, she’s taking a little break right now. Recently got married and married a big time wall street lawyer up in New York City, and they bought a little place 2 hours outside of Manhattan, so they’re commuting, and she’s taken a little time to remodel and refurbish and decorate this little farm place, and so she’s taking a break right now, but she’s done everything, film, tv, the stage, and a lot of modeling and has done quite well for herself.

    Ryan Doolittle [00:12:44]:
    What’s her name? So our listeners can listen to?

    Greg Russell [00:12:45]:
    Her name is Madison. Madison Russell.

    Ryan Doolittle [00:12:48]:
    Madison Russell. Okay. We will keep our eyes out.

    Greg Russell [00:12:51]:
    My other daughter, who lives out in Denver, Colorado, she was the equestrian in our family. So, all your parents out there, if your daughter ever says they want to start riding horses when they’re at school one day, just move and don’t tell them where you moved. I like to joke that we bought our veterinarian a brand new ocean front house here in sea funds, but she did quite well with that. Rode all the way through college and actually won the NCAA national championship, so.

    Ryan Doolittle [00:13:23]:
    No kidding.

    Greg Russell [00:13:24]:
    Yeah, collegiately. So I have, with my beautiful bride of 35 years, been lucky enough to have beautiful daughters in our life. And they are wonderful, kind, gentle people and couldn’t be more proud of them.

    Ryan Doolittle [00:13:38]:
    Wonderful, kind, gentle, and talented.

    Greg Russell [00:13:40]:
    Yes.

    Ryan Doolittle [00:13:41]:
    Yes. Wow. Okay. That’s.

    Greg Russell [00:13:43]:
    It.

    Ryan Doolittle [00:13:43]:
    Seems like everyone in your family has some amazing accomplishment. They’ve. They’ve made.

    Greg Russell [00:13:48]:
    Well, you know, I’ve always been a doer, and we were lucky that we homeschooled our children a lot. And wherever we went, we all went together. So if we went to Hawaii on cruise ships for two months, we all went and we did the school thing, but we also did volcanoes and I, all the rest of it, or, you know, going through the Caribbean or going to New York City or wherever we went, we went as a family. And there was so much positive that came out of that. Being able to travel and experience different people and cultures and all of that together as a family was a real blessing.

    Ryan Doolittle [00:14:28]:
    Yeah. Yeah. Well, and all that success. I mean, you say you’re a doer, whereas I like to drink doers, so maybe that’s why I’ve had less success than you.

    Greg Russell [00:14:38]:
    Well, I’ve been accused a lot of things, but never of having a drink before going on the stage to do kid shows. So I’ll leave that right there.

    Ryan Doolittle [00:14:47]:
    Yeah. Okay. Well, okay, Greg, let’s talk a little bit about. So after this amazing career, which is still going, you’re sort of deciding that you want to transition to not necessarily retirement, but a different life, right. Tell me a little bit about that.

    Greg Russell [00:15:06]:
    Yeah. Traditionally, you know, I was on the road 200 nights a year doing all the things I talked about, cruise ships, Colorado college campuses. I think I’ve done over 600 colleges, corporate convention shows, and all of that is fun. But the problem is like a cruise ship fly to Cozumel, Mexico. It takes three days out of my life to do 245 minutes shows. And when you’re young and, you know, not 98 years old like I am now, you know, you know, that was okay, but now that I don’t have to do it anymore, now instead of working 300 nights a year, maybe I’ll work 100 nights a year. But I don’t want to give it up. I still get the charge out of walking out on stage and, and doing my silly, goofy stuff that I get to do.

    Greg Russell [00:16:00]:
    But I’m at a stage in my life where I get to pick and choose, and if I don’t want to fly to Seattle, Washington, for a 45 minutes gig, I don’t have to do it anymore. But if it’s somewhere we want to go or something we want to see or do or explore around, then we take the time, and it’s like getting paid to go where you want to go. So it’s, it’s kind of cool. This fall, my wife and I are doing several cruises. We’re going to do a wonderful river cruise on the Danube in Europe. So that’s like a two and a half, three week trip that, you know. Who gets to do that? Nobody. So I’m very fortunate.

    Greg Russell [00:16:41]:
    So I’m, I would say semi retired, you know, so I work maybe a third of the year instead of working nonstop year round, and now I’m a little more choosy about where I go.

    Ryan Doolittle [00:16:55]:
    And when we talk a lot, and a lot of the guests that I have talk about this, the word retirement feels a little outdated. It connotes, you know, sitting in a la z boy all day or something. No way. Right? And it sounds like you love what you do. You just want to do it when you want to do it.

    Greg Russell [00:17:13]:
    Well, not want to do it. If I could Star Trek myself and transport myself to Sydney, Australia, and jump on a ship and do a couple of shows in a tuxedo with an orchestra, and then magically be back home instead of, you know, travel is difficult. It used to be easier than it is now, but now with all the. All the delays and, you know, travel is not as easy it used to be. And I’ve accumulated millions of frequent fire miles. When I show up at a delta desk and hand on my card, they bring people out from the back, say, look at this. We’ve never seen one of this. But I earned those miles.

    Greg Russell [00:17:57]:
    I earned them the hard way.

    Ryan Doolittle [00:17:59]:
    Yeah. That’s a lot of taking your shoes off for security. Yeah.

    Greg Russell [00:18:03]:
    Yeah.

    Ryan Doolittle [00:18:04]:
    How many types do they do? They search your guitar all the time. How does that work all the time?

    Greg Russell [00:18:08]:
    Because, you know, it’s not something they see all the time. And there’s some little hidden compartments. And, of course, I’m in the entertainment business, so I must be smuggling something, you know?

    Ryan Doolittle [00:18:18]:
    Right, right.

    Greg Russell [00:18:19]:
    You know, a lot of my travel traditionally has been international travel, and I’ve seen the back room of a lot of airports.

    Ryan Doolittle [00:18:26]:
    Really? You mean they. They take you into the back to question?

    Greg Russell [00:18:29]:
    Oh, yeah. Oh, yeah.

    Ryan Doolittle [00:18:30]:
    Really?

    Greg Russell [00:18:30]:
    Well, you. You get off a cruise ship in Cartagena, Columbia, at 07:00 in the morning and go straight to the airport, and the guy looks at your passport and says, well, you just got here. Yeah. Well, you don’t like our country? Well, it’s not that I’m flying to, you know, Miami. But you just got here. Who did you meet while you were here? I didn’t meet anybody. Well, what were you doing? Do you have a work permit? Well, no, I was on a. You know, and it just.

    Greg Russell [00:18:59]:
    It’s difficult at best.

    Ryan Doolittle [00:19:01]:
    Can you play him a little song to sort of lighten the mood?

    Greg Russell [00:19:05]:
    No. Cause I want to get home. I don’t want to myself over.

    Ryan Doolittle [00:19:10]:
    Yeah. So your shows at Hilton head, which are very easy for you to get to. I mean, it must be really close to where your house is or. I don’t know exactly.

    Greg Russell [00:19:24]:
    I leave my house about a half hour before I’m due on stage. I have an assistant roadie, if you will, who takes care of everything for me. I show up, I plug one chord into a guitar, and I’m ready to go, and he takes care of everything else.

    Ryan Doolittle [00:19:42]:
    Oh, that’s. That’s fantastic. That’s the way to go.

    Greg Russell [00:19:45]:
    Yeah, yeah, absolutely.

    Ryan Doolittle [00:19:47]:
    So will you continue? How many shows do you play now? And is that. Are you. Are you lowering that number or the ones there? You’re gonna keep doing as many as you’ve always.

    Greg Russell [00:19:57]:
    Well, for the first 40 years, I worked six nights a week, and then I did two boat cruises every week. I invite, you know, 150 of my best friends on a Thursday and Friday morning to go out on this big tour boat. And we talk about the environment, and we see dolphin and manta rays and eagles and all of that, and I talk about how important it is to protect the environment. And, you know, I’ve been doing that for probably 35 years. So this summer, I cut back to. Or two summers ago, I cut back to five nights a week. This summer, I cut back to four nights a week and one boat cruise. So I’m finding the sweet spot now of that fine line between overexposing myself at this point, or I’m looking for longevity.

    Greg Russell [00:20:52]:
    I’m finishing up my 47th year, and I’d like to do 50 seasons. Kind of has a nice ring to it, as long as I stay healthy and they want me, and people keep showing up, and we just had the biggest summer I’ve ever had, so.

    Ryan Doolittle [00:21:06]:
    Really?

    Greg Russell [00:21:07]:
    Yeah, no complaints.

    Ryan Doolittle [00:21:09]:
    So you think at 50, you might stop doing it or you might, or you’re not sure yet?

    Greg Russell [00:21:14]:
    I’m not sure yet, but that’s my goal. I’d like to hit 50. Even if it’s one night a week?

    Ryan Doolittle [00:21:19]:
    Yeah.

    Greg Russell [00:21:20]:
    You know, I’m not saying that’s what it’ll be, but, you know, I’d like to hit 50 and then figure it out from there.

    Ryan Doolittle [00:21:25]:
    Yeah. Okay. So you still have the fire to play. You just want to make sure you’re doing it the right amount for you.

    Greg Russell [00:21:33]:
    Well, as you say this, I had a whole lot more fire 14 weeks ago than I have right now. At the. At the end of the season, I always look forward to the beginning and the end of seasons, as you know or may not know it can be 100 degrees here and 100% humidity and, you know, we get, I don’t know, 1000, 1500 people every single night. And it doesn’t look. I try to make it look pretty easy, but, you know, it can be a challenge.

    Ryan Doolittle [00:22:07]:
    Yeah. Yeah. I think that’s something that fans of musicians don’t think about, is how much work it takes to get there and leave and do the whole thing. We just see you on stage and it looks so fun, you know?

    Greg Russell [00:22:19]:
    Yeah, well, it is fun. And I have fun. I have fun every single night. You know, the key to my thing is I interact with. With these kids and, you know, I do, like, 45 minutes and set the whole thing up. And then I invite a few kids to come up and they sit on my knee and I get them to talk and try to say some funny stuff and get them to sing a little song or. Or whatever. The other night, I had a little kid up, four years old and cute as he could be, and I said, you don’t look very happy.

    Greg Russell [00:22:53]:
    He said, I got in trouble today. I said, what happened? And he looked around and there’s over a thousand people sitting there. He looks around and he leans into my mic and he said, somebody pooped in my pants. You could write that if you wanted to. You could not make that up.

    Ryan Doolittle [00:23:16]:
    He said it as if he may not be one of the prime suspects. Right?

    Greg Russell [00:23:19]:
    Yeah. So I waited for the laughter to die down, and I said, well, who was it? He goes, I don’t know.

    Ryan Doolittle [00:23:30]:
    Kids are geniuses. Yeah. Like you said, you could not come up with that.

    Greg Russell [00:23:34]:
    Yeah, they have no filter. They have no filter. I had a kid up not long ago, sat on my knee, and it’s summertime here, so they wear shorts and a little t shirt or whatever, and he sits on my knee and he. And he has one flip flop on and the other foot has nothing on it. I said, hey, pal, you lost a flip flop? He looked at me saying, no, I didn’t. I found one.

    Ryan Doolittle [00:24:01]:
    Oh, my gosh. That’s perfect comic timing right there.

    Greg Russell [00:24:05]:
    One of my favorite questions I ask them is, hey, have the police ever been to your house, all in their face, lined up? Yeah, you know what? One time. And then I’ll cut them off. But, you know, they have no filter. They’ll say anything.

    Ryan Doolittle [00:24:21]:
    Yes, for sure. You know, that just reminds me. The other day, I took my. I have a little son. I took him to the park, and I got there, and he was only wearing one shoe. And I was so distraught because now I couldn’t really let him walk around after we got there, and I found it in a bush, so that one had a happy story.

    Greg Russell [00:24:39]:
    Yeah, they don’t care. Another one will come along.

    Ryan Doolittle [00:24:44]:
    Right, exactly. So do you have. Do any of your kids have kids? They sound maybe like they’re too young at this point.

    Greg Russell [00:24:50]:
    No, no. They’ve been very career minded, and, you know, I think my wife would trade me the house, the dog. Well, maybe not the dog, but everything for one grandchild. We are very, very hopeful here. Before too long.

    Ryan Doolittle [00:25:07]:
    Do you think they want your kids? Want to have kids?

    Greg Russell [00:25:10]:
    I do. I think they talk about their own childhood in such idyllic, wonderful ways that I can’t imagine that they would not want to experience that for themselves.

    Ryan Doolittle [00:25:22]:
    Yeah. It’s been amazing seeing the reaction of my parents or my wife’s parents. They light up so much seeing their grandkids.

    Greg Russell [00:25:30]:
    Yeah.

    Ryan Doolittle [00:25:31]:
    It’s, uh. They don’t light up that way when they see me, you know?

    Greg Russell [00:25:35]:
    Well, you know, my philosophy is grandchildren are grandparents reward for not killing their own kids.

    Ryan Doolittle [00:25:44]:
    I like that.

    Greg Russell [00:25:46]:
    And grandparents are nicer than real parents.

    Ryan Doolittle [00:25:49]:
    Yes.

    Greg Russell [00:25:50]:
    They figure, hey, screwed the first deal up, but now I got another shot at this whole thing.

    Ryan Doolittle [00:25:55]:
    I know. It’s amazing. The things that I would have been in trouble for. Those are all out the window, you know?

    Greg Russell [00:26:00]:
    Oh, yeah.

    Ryan Doolittle [00:26:01]:
    Yeah. Well, okay, so what now? Now that you may have a little more time, I mean, it sounds like you may need to rest, but you’re still playing so much. But do you have any other core pursuits or things you love doing besides music?

    Greg Russell [00:26:16]:
    Well, you know, I love writing, and that’s very lonely creative process. And we spent a lot of time down in the Bahamas, a little place called Green Turtle, which is just this little spit of land. And Internet doesn’t work very often, and the phones never work, so gives me a chance to be creative. I love writing. You know, I have a brand new book out, which will be my third children’s book coming out. I’ve done, I don’t know, 1214 albums full of psalms. I’ve written a lot for tv and. And other things, so I love that creative process, but I have to really get quiet in order to do that.

    Greg Russell [00:26:59]:
    And at home, it seems there’s so many distractions and all my buddies calling me to play golf and, you know, I like to cut the grass and, you know, do all that. That regular dad stuff. But I also have a small business. I have some investors, and we buy homes, remodel them, and then flip them. Okay. And I’ve done. I don’t know, 1516 houses. I’m doing one right now.

    Greg Russell [00:27:28]:
    I’m the guy that kind of coordinates all the subcontractors and all that. It’s been highly, highly successful, and I really enjoy that because it’s. It’s a creative process. And putting the pieces of the puzzle together on a 40, 50 year old house, that’s, you know, time to get upgraded. And here the real estate market is, like, where you are off the charts, unbelievably good.

    Ryan Doolittle [00:27:57]:
    Yeah.

    Greg Russell [00:27:58]:
    So every project we’ve ever done has, has turned a nice profit. And I just love that engagement with, with all the guys I work with, and it’s a lot of fun. So that keeps me busy as well.

    Ryan Doolittle [00:28:11]:
    It sounds like it. And I don’t know if I’ve. Correct me if I’m. If this is just a cliche, but a organized, detail orient oriented musician, is that common? It sounds like you have all those skills.

    Greg Russell [00:28:25]:
    I think most musicians like to sleep till noon.

    Ryan Doolittle [00:28:28]:
    Yeah.

    Greg Russell [00:28:29]:
    You know, and then go to IHOP or somewhere and eat breakfast and get ready for that two, three hour gig that is so horrible to do every.

    Ryan Doolittle [00:28:39]:
    Night, you know, whereas you’re in spreadsheets and it sounds like you’re organizing contractors.

    Greg Russell [00:28:45]:
    And I do have that left brain, right brain thing. A lot of guys don’t. They just love the performance part. But I’ve always. When young guys come to me for advice or whatever, you know, I tell them it’s show business. It is a business. And I never put all my eggs in one basket. Yeah, I had Hilton head, but also I had veil and aspen all winter.

    Greg Russell [00:29:11]:
    And when I wanted to go on cruise ships, I did. And as a college entertainer of the year, I could pick and choose to go to colleges. So I never had a downtime or an off season. There was always somewhere new and refreshing to go. Because what I do here on Hill Net has no relationship to what I do on a cruise ship in Australia. I mean, totally different audiences. I mean, I’m wearing a tuxedo and working with an orchestra, and here I’m wearing shorts and a t shirt and sweating, you know, my rear end off with four year olds saying, no, I didn’t lose a flip flop. I found one.

    Greg Russell [00:29:50]:
    So.

    Ryan Doolittle [00:29:50]:
    Right, right.

    Greg Russell [00:29:51]:
    I think that helped keep me fresh all the time because every venue demands something very different. And, yeah, not that you become a chameleon, but you learn to fit a round peg into a round hole and not try to force a square peg into a round hole.

    Ryan Doolittle [00:30:11]:
    Yeah. You have to know your audience to know what they’re looking for, I would imagine.

    Greg Russell [00:30:15]:
    Yes.

    Ryan Doolittle [00:30:17]:
    Like a comedian, they can’t tell specific jokes. A certain crowd or.

    Greg Russell [00:30:21]:
    Right, yeah.

    Ryan Doolittle [00:30:23]:
    So. And I imagine the tuxedo wearing orchestra crowd doesn’t want to flip flop jokes, maybe, you know?

    Greg Russell [00:30:29]:
    No, but they want to laugh. And, you know, I never finish a song. I never play a whole song. I do so many bits and shtick that, you know, the music is there, just kind of tie it together. But I’ve made a living in between songs, really.

    Ryan Doolittle [00:30:47]:
    That is really.

    Greg Russell [00:30:48]:
    Nobody gonna pay me to stand there and sing bocelli, you know? You know, I use the music as a tool, and I love the music part, but I love hearing people laugh. That’s what really rings my bell.

    Ryan Doolittle [00:31:06]:
    Wow. So do you think you had that fire in you and you. So you just learned music as a way to do that, or.

    Greg Russell [00:31:13]:
    No. You know, when the Beatles came out in the sixties, I saw that and I heard that, and I thought, man, that is just so cool. So I still have. When my parents passed away, we kind of clean their house out of all the stuff, and I found a receipt that my mother had kept for the first guitar she ever bought for me. And she paid $6 a month at the music store so that I could get a guitar. So little did she know that that would set the blueprint for the path of my life. And I was always the guy, the camp counselor guy, sitting around the campfire singing Peter Palm Mary songs or whatever.

    Ryan Doolittle [00:32:00]:
    Okay.

    Greg Russell [00:32:01]:
    And then. And then I started singing in the bars, and I kind of liked that. It was the singer songwriter era of Billy Joel and James Taylor and Dan Fogelberg and all those guys. And I sing all the Beatles songs, but when I was around a campfire or with kids, there was just something special about it that seemed very genuine and authentic to me. And when I got to Disney, you know, they’re all about connecting with audiences. And in most cases at Disney, I didn’t have a microphone, no Pa system, really. You just set up somewhere in the park and stand under a shade tree and try to gather a crowd together to distract them from the two hour wait to go in the country bear jamboree. And so I learned how to communicate with people, and that if I have a gift, that’s what it is.

    Greg Russell [00:32:57]:
    It’s not vocally, it’s not singing, certainly not how I look, but if I have a gift, it’s just being able to connect with people.

    Ryan Doolittle [00:33:10]:
    That sounds like some of the best training you could get for what you do is having to, because I’m sure at that point, you’re just, like, to the crowd standing there, come listen, you know?

    Greg Russell [00:33:19]:
    Yeah, yeah, yeah.

    Ryan Doolittle [00:33:21]:
    Now people are clamoring to listen to you, but. But you had to kind of strengthen that muscle.

    Greg Russell [00:33:26]:
    Yeah. And it’s. It’s an art knowing what to say, when to say it, and when to shut up.

    Ryan Doolittle [00:33:31]:
    Right.

    Greg Russell [00:33:31]:
    You know, I’ve just had such a great run, and I’m so grateful for everything that’s come my way. And I met such wonderful people on Hilton head. You know, tonight I’ll have four generations of family members, from grandma down to a little four year old. And so the material has to appeal across the board. I can’t do a little kid show of the little duck was swimming in. I can’t do that because the dad and the grandma on the back will shoot themselves.

    Ryan Doolittle [00:34:06]:
    Right.

    Greg Russell [00:34:06]:
    So if two thirds of my audience on any given night is. Is adult, then I have to be able to appeal to them and shoot some things over the heads of the kids, but, but still relate to the children. So there, there’s a real art there. And again, if I have a gift, I think that’s what it is.

    Ryan Doolittle [00:34:27]:
    I think that’s so true. It just, again, makes me think about the little shows my son watches. And some of them, I. Like you said, I want to. I want to scream, but other ones really connect with me, even though they seem like a kid show to the fact where I’ll find myself asking my wife, so, do you think Daniel Tiger was upset that one day when, you know, and she’s like, I don’t want to talk about this, but it really. It lands, you know?

    Greg Russell [00:34:55]:
    Yeah. Well, in our day, it was a character named Barney, you know, big purple dinosaur my kids would watch, and I’d walk through the room and want to hang myself. But there is something very appealing if you can connect, as a lot of these characters over the years have been able to do, if you could connect in any way, then you have an audience that is hungry for material, and they hang on every word. So I have to be very, very cognizant of what I’m saying and when I’m saying it, how I’m saying it.

    Ryan Doolittle [00:35:34]:
    Yeah, for sure. Speaking of Barney, it sounds like there’s a sketch you should see on Saturday Night Live. I don’t know if you ever saw it, but Charles Barkley was hosting, and he played Barney one on one in basketball, and, you know, he gives him a lot of elbows to the face. Sounds like you might enjoy that.

    Greg Russell [00:35:53]:
    Yeah, yeah, yeah.

    Ryan Doolittle [00:35:54]:
    But, yeah, it sounds like you have a real respect for your audience, which I’m sure they really appreciate.

    Greg Russell [00:36:00]:
    Well, I do. And I assume every single night that they’re smarter than I am. They’re more well traveled than I am. They’ve seen life, and, you know, I can’t fake it. I have to be genuine and authentic. And, you know, I get kids up out of the audience, and my job is to play straight man and get them to be funny and to hear people laugh. Laughing with them, but not at them.

    Ryan Doolittle [00:36:31]:
    Right.

    Greg Russell [00:36:32]:
    And there’s a fine line to walk there, and it’s just worked incredibly well.

    Ryan Doolittle [00:36:39]:
    Yeah. And I imagine when you’re doing it right, the little kid can sense that they’re not laughing at him.

    Greg Russell [00:36:46]:
    Oh, absolutely, absolutely. They make little signs there. They get there an hour before I do because the seating is at a premium right up close, because I have them all sit on stage with me, and they make these signs like a back of a pizza box or a Coors light box. You know, dad says, here, I drink to the last eight of these. You can use this here. Make sign. But. But they make signs and they hold them up that says, basically, you know, my mom sang with you 35 years ago, or I drove all the way from Chicago just to be here one night.

    Greg Russell [00:37:24]:
    Please pick me. You know, so I can’t pick them all with signs, but I have a whole bit where I walk around and I read every single sign out loud.

    Ryan Doolittle [00:37:35]:
    Really?

    Greg Russell [00:37:36]:
    So that I am, in effect, rewarding them for their effort that they put in. Even though I can’t choose every one of them, I can acknowledge that they put some effort in, and I appreciate that.

    Ryan Doolittle [00:37:51]:
    Well, I mean, and the thing is, for, you know, for you to do so many shows, but for them, they’re gonna. That one memory is gonna last it. Yeah. Yeah.

    Greg Russell [00:38:01]:
    And I’ve always been under the. Lived under the philosophy that tonight, somebody is going to see me for the first time, and somebody’s gonna see me for the last time.

    Ryan Doolittle [00:38:13]:
    Yeah.

    Greg Russell [00:38:14]:
    And they both deserve the same amount of energy, enthusiasm. They don’t care that I’m on show number 96 for the season. They don’t care. You know, so I have to. I can’t phone it in. I’ve got to do my best to deliver something that’s genuine and authentic, and that’s. That’s true in any business.

    Ryan Doolittle [00:38:36]:
    Right. I. I mean, it’s a lot of. Sounds like a lot of pressure, but it also sounds very rewarding.

    Greg Russell [00:38:43]:
    Well, I have buddies tell me, hey, I’m going to come by and heckle you tonight. I always say, brother, trust me, you do not want to heckle a guy with a microphone and 50 years of stage experience because you will lose. That’s very dull. I don’t think anything could happen that I would see or experience from a stage that would be brand new for me. So, you know, I’ve kind of got a handle on what I need to do and how I need to do it.

    Ryan Doolittle [00:39:15]:
    You. So you get hecklers while you’re singing with children?

    Greg Russell [00:39:18]:
    Not Heckler. Heckler. You know, some guy yell out, hey, sing something. You know? You know?

    Ryan Doolittle [00:39:25]:
    Oh, yeah, yeah.

    Greg Russell [00:39:26]:
    You know what I mean? But because the kids are on stage with me, I’m looking over their heads. They sit, you know, crisscross applesauce in front of me, and I look over their heads to, you know, hundreds and hundreds and hundreds of adults. But the show I’m seeing in front of me that’s going on, can you imagine 803 four six year olds all elbowing and fighting and pulling each other’s ears and kiss tying my shoes together because I can’t move. I mean, I see a whole different show than what. What the audience sees.

    Ryan Doolittle [00:40:03]:
    Right. Has that happened? They’ve tied your shoelaces together?

    Greg Russell [00:40:07]:
    Yeah.

    Ryan Doolittle [00:40:08]:
    Oh, my.

    Greg Russell [00:40:09]:
    Absolutely.

    Ryan Doolittle [00:40:10]:
    Okay. You really know how to adapt and move on that stage.

    Greg Russell [00:40:16]:
    Or, you know, I’ll do something simple saying, gosh, what a special night this is. And a little kid 3ft in front of me will yell outd, no, it’s not, you know, okay, kid, just relax.

    Ryan Doolittle [00:40:28]:
    Right, right.

    Greg Russell [00:40:31]:
    But I’ve learned how to block it all out, you know, and just. Just keep going just 1ft in front of the other one. No matter what train wreck happens in.

    Ryan Doolittle [00:40:40]:
    Front of me, it’s hard to go 1ft in front of the other when your shoelaces are tied together, but I guess you make it work.

    Greg Russell [00:40:46]:
    You got that right.

    Ryan Doolittle [00:40:48]:
    So, Greg, what have been some of the biggest challenges? I guess, as you’ve sort of tried to go from work every gig you can to this more streamlined schedule that fits your.

    Greg Russell [00:41:01]:
    Yeah, I’m not sure it’s a challenge. It’s more of a relief, really. You know, when you’re climbing, you’re trying to create a career and create something that you vision in your mind and yet is, for most of us, unreachable. You know, I’ve opened for major, major acts and Vegas and concert tours and, you know, Kenny Rogers, Kenny Loggins, beach boys, on and on and on and on. And, you know, as the opening act, nobody’s there to see you. And my job is to come out and get the people back into the same mood they were in before the guy announced I was coming out, you know?

    Ryan Doolittle [00:41:47]:
    Yeah.

    Greg Russell [00:41:47]:
    So you’re trying to build something and grow something, which is the challenge of climbing the mountain. And then once you get settled into, okay, this who I am, this is what my career is. I’m not going to have a weekly show on. On CB’s, and I’m not going to be famous where I can’t walk down the street. But I’ve found a nice little niche for myself once you settle into that. And again, knowing I don’t have to fly anywhere that I don’t want to go to anymore, there’s a relief in that.

    Ryan Doolittle [00:42:23]:
    Yeah.

    Greg Russell [00:42:24]:
    And. And yet there’s also part of me that thinks, well, boy, they’re throwing a lot of money my way to go do that, and why won’t I? Why don’t I want to do it? Well, the fact is, you know, I love my wife and I love my life, and I love what we get to do together. And I take a little comfort knowing that now I get to do what I want.

    Ryan Doolittle [00:42:48]:
    Yeah, absolutely.

    Greg Russell [00:42:50]:
    I’m not building anymore. I’m maintaining, really. You know, my career is what it’s going to be. I’m never going to be a household name. You know, I’m not going to be headlining in Vegas, but I’ve created a little niche for myself that has been highly rewarding and satisfactory.

    Ryan Doolittle [00:43:09]:
    Well, after doing this show, you may be a household name. You know, this is probably gonna finally put you on the map.

    Greg Russell [00:43:15]:
    Well, there you go, brother.

    Ryan Doolittle [00:43:17]:
    Although I would say when I was, I remember being, you know, younger and wanting to be rich and famous. And the being rich part never went away. But the. But the famous part started to seem like it might be kind of inconvenient and not that fun. Yeah.

    Greg Russell [00:43:34]:
    Well, as I said before, I’ve had the opportunity to be around a lot of famous people. One of my great friends in the world, who narrated this Apple tv documentary that highlights what we’ve been doing, is Jim Nance, the CB’s sports hall of Fame broadcaster. He’s the best in the business. I mean, who else does the Super bowl, including the on field presentation, then does the NCAA Final Four, and then a week later, does Augusta, you know, the biggest golf tournament in the world. Who in our lifetime as a broadcaster could do that? Well, my buddy Jimmy. He’s that guy, but he is so gracious in being a celebrity. Everywhere he goes, he takes time to visit with people and does it in such a wonderful way. I’ve introduced him to friends of mine that maybe he won’t see for four or five years, but he remembers something about those people four or five years later.

    Greg Russell [00:44:39]:
    Really, he has that gift and he is. I tell people. People ask me about him all the time. I tell people, first of all, obviously, he’s a hall of Fame broadcaster, but he is a world class human being, and I just love him and respect him for how he has handled his life and how he interacts with the planet. He’s just a special human being. And if you have mentors in life, I’ve tried to learn from, from people like that. When I was, I went to a private boarding school for high school, private fundamentalist christian boarding school, and Billy Graham’s children went to this particular school. And because of that, I got to travel around some with Billy Graham and saw how he handled everything in his life.

    Greg Russell [00:45:37]:
    And if you can be lucky enough to find people like that and watch them and model how they interact with the world, then you’re one or two steps ahead of everybody else.

    Ryan Doolittle [00:45:50]:
    Yeah. I can only imagine with that kind of fame to still be that gracious and remember someone four years later. I mean, in the case of Jim Nance, unbelievable. He is someone. When I hear his voice, I just get that feeling, like a warm hug, kind of like, all right, I’m in good hands for this game, you know, that sort of thing.

    Greg Russell [00:46:12]:
    And, you know, as a broadcaster, you would know. You’ve got a set of headphones on right now. When I go to an NFL game with him or go to, when he broadcasts a golf tournament, he’s got a headset on and there are 47 people talking to him all at the same time, and he’s delivering everything just as calm and collected and smooth. And it’s a real art, what he does.

    Ryan Doolittle [00:46:41]:
    Absolutely. I mean, if my wife tries to tell me two things, I have a mental breakdown. I can only do one.

    Greg Russell [00:46:48]:
    I’m with you. One input, one output.

    Ryan Doolittle [00:46:52]:
    Right. I’m willing to do these. I just have to do them one at a time. Well, do you have any advice for people who, maybe they’re thinking about winnowing down their obligations or getting to that? Like we said, retirement may not be the right word, but they want to transition into, like, the life they want?

    Greg Russell [00:47:13]:
    Yes.

    Ryan Doolittle [00:47:14]:
    Any advice for them?

    Greg Russell [00:47:15]:
    Yes. None of us are promised tomorrow, and we always say when. Well, when the kids go away or when I don’t have to go to work every day or when, you know, I get this windfall or whatever. If you keep waiting for when you have to make things happen in your life, you have to be proactive and have a plan, have goals, follow the plan and structure your life financially, emotionally, and every other way so that when you get to the point where you can make a decision to transition into whatever is next for you, you have the ability to do that. But it takes planning and it takes work. It doesn’t just magically drop into your lap.

    Ryan Doolittle [00:48:04]:
    Yeah. And so you’ve done that. You did a lot of forethought and planning, and now it’s sort of paying off. Jeff.

    Greg Russell [00:48:11]:
    Well, we’ve put ourselves in a position financially where I don’t ever have to work another day in my life. And I could have said that five years ago. I’m still working because I still love it. Now. Do I want to do it 300 nights a year? No, I don’t. But do I want to do one or two great big three $4 million houses every year and get the satisfaction and the profitability out of that? Yes, I do. And do I want to go on the river cruises and go to Australia and go to Tahiti if I want to? Yeah. So there’s.

    Greg Russell [00:48:47]:
    There’s a good mix there for me, but I’ve positioned myself that I have options. And if you don’t have options, whether they come because you don’t have time or you don’t have the energy or you don’t have the health or you don’t have the finances, it makes doing the things that you really, really wanted to do make it much more difficult. Don’t wait. Don’t wait. Put yourself in a position where you can make those choices.

    Ryan Doolittle [00:49:16]:
    Yeah, absolutely. I love that advice. The situation I get into on a lot of these interviews is I’m just listening for me, and I’ve taken all the advice, so thank you so much for all of that. One question before I let you go. I want to make sure you can plug anything you might want people to go find, maybe your new book or nothing.

    Greg Russell [00:49:38]:
    No, I don’t really want to plug anything. Okay. I’ve gotten a tremendous amount of activity messaging and all of that through the apple tv thing. You know, it’s out. It’s an hour and 20 minutes documentary. Two kids who used to sit in front of me are now very successful filmmakers, and they approached me three years ago and wanted to make this documentary, and I told them, no, I didn’t want to do it. And they came back two years ago. I took them to lunch, and they pitched it again.

    Greg Russell [00:50:11]:
    And I said, guys, you know, I feel like the cop on the street here. There’s nothing to see. Move along. Go do something interesting. Well, they came back, I guess, a year and a half ago, and, you know, they finally convinced me that, you know, this would be something maybe my daughters would like to see ten years from now, or my friends that I’ve made around the world would like to see. So they crafted it, and Apple TV picked it up, and within 24 hours of it being broadcast, it went to the number one documentary in America, holy cow, on Apple TV. So that has kind of opened up the floodgates of me, hearing from people all over the country, third and fourth generation of family members, who, I guess this has struck a chord with them that’s been very, very rewarding. So if somebody has Apple TV and wants to dial it up, I would encourage them to do that.

    Greg Russell [00:51:11]:
    It’ll be on Amazon and all the other platforms in October. But for right now, it’s exclusive to Apple TV.

    Ryan Doolittle [00:51:18]:
    To Apple TV. And you said it really struck a chord with people. Was that one of the three and a half chords? You know.

    Greg Russell [00:51:26]:
    See, now, that was a little bit of a shot there, brother.

    Ryan Doolittle [00:51:29]:
    I couldn’t resist. I. Well, Greg, thank you so much for joining us on the Happiest Retirees podcast. It’s been a real honor for me, and I know for all the people I work with. It’s just so exciting for us.

    Greg Russell [00:51:45]:
    Well, it’s my pleasure. Again, I have been trying to live a very intentional life, full of gratitude for the life I have, for the career I’ve had, for the beautiful wife and children that I have. I’m just one of those guys who feels like they won the lottery. And so when things come along and give me a chance to have a platform like this to maybe encourage people and tell people to follow their dreams, that’s a good thing for me. So, thank you for inviting me and including me in what you’re doing.

    Ryan Doolittle [00:52:22]:
    Absolutely. And I’d be remiss if I didn’t say, be careful of the alligators, because being from the west coast, I’m obsessed with worrying about that.

    Greg Russell [00:52:31]:
    I tell you what, I’ll tell you one quick story. We have alligators all over the place here. And when one of my daughters was real little, we had a hamster, and the hamster ate a hole in the wall, got out of his cage, and he got trapped behind the wall. So we have a critterman here on hill net. So I called him, I said, hey, Critterman, it’s Greg Russell. He said, hey, did you see my picture in the paper? I just trapped the largest alligator in the history of South Carolina. We had to pick him up with a car wrecker and put him on the back of a truck. And I said, yeah, your picture was on the front page of the paper.

    Greg Russell [00:53:09]:
    He said, yeah, it’s the biggest alligator in history of South Carolina. He said, what do you need? I said, well, I got a hamster stuck behind the drywall.

    Ryan Doolittle [00:53:23]:
    His real step down.

    Greg Russell [00:53:26]:
    So he came and he got the hamster out for $1,500 and the hamster croaked the next day. Oh, no. Yeah. So stay away from the alligators.

    Ryan Doolittle [00:53:42]:
    Stay away from the alligators and keep your hands hamsters safe. All right. All right, Greg. Well, thank you. You have a great day and enjoy whatever time off you might have.

    Greg Russell [00:53:52]:
    Thank you, brother. I appreciate you. God blessed I.

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