How A Kid From Georgia Built Radio Giants And a Wonderful Life

What does it take to lose almost everything as a kid, find your footing in the Marines, and then build not one but two major radio companies? Terry Jacobs joins me with his wife Susan at his side to trace a remarkable path from small-town Georgia to the highest levels of insurance and broadcasting, and back to the values that has kept their family steady.

We start with the early blows: a father’s death at nine, a house lost, and a football dream ended by injury. The Marine Corps reshaped Terry’s mindset, turning discipline into opportunity as he attacked actuarial exams that most never finish. Promotions at USF&G and Aetna came fast; Prudential tapped him to help launch a new personal lines venture. When the fit soured, Cincinnati called. That jump unlocked a new chapter at a premier company in Cincinnati. He then go to found Jacor, mastering the buy-improve-trade-up game, and landing crown jewels like WLW and WEBN. He shares the real cost of leverage, the calculus behind two sales to Clear Channel, and why a third swing taught him to respect “enough.”

Beyond the boardroom, this is a love story and a community story. Terry and Susan relive chaotic, laughter-filled ski trips with friends, the teenage meet-cute at Susan's parents general store, and the nightly prayers that still anchor them after sixty-three years. Their investment in Morehead State football—facilities, fundraising, belief—helped spark a record-breaking comeback win and offered a lifeline to players who needed a shot at college. The advice hits hard: whatever difficulty you expect, double it; whatever money you plan, triple it; decide not to quit—then prove it when quitting feels logical.

If you’re an entrepreneur weighing risk, a leader navigating conflict, or someone searching for a compass that points to what’s right even when it hurts, this story delivers hard-won lessons with heart. Subscribe, share this with a friend who needs a push, and leave a review telling us which moment stayed with you.

Transcript

Welcome And Guest Introduction

SPEAKER_03 0:02

Welcome to Dan the Road Trip Guy. I'm your host, Dan, and each week we'll embark on a new adventure, discovering memory and life lessons of our incredible guests. From everyday travelers to thrill seekers and everyone in between, this podcast is your front road seat to inspiring stories of passion, resilience, and the pursuit of happiness. So buckle up and enjoy the ride. I'm on the road again today, which is a pleasure for me. I'm in the home of my guest, Terry Jacobs, and actually Susan, his wife, is here with us. So this is a special treat for me. Terry, if you're from Cincinnati, you probably recognize the name. He's a successful businessman, entrepreneur, executive. He's also, or if you're from Moorhead, Kentucky, you might uh know Terry and Susan from Moorhead because they were very active in the football program there. The one thing and and I haven't seen Terry or Susan in a number of years. We went to church together years ago. And the one thing I can say about Terry is when you walk away from him, you simply feel better about yourself. And that's the one thing I'll always remember. Welcome, Terry, Susan, to Dan the Road Trip Guy.

SPEAKER_01 1:23

Welcome to our home.

Terry’s Early Life And Loss

SPEAKER_03 1:25

Yes, thank you. It's a pleasure to be here. It's an honor. Terry, take uh take a couple minutes, make it short, but tell me who is Terry Jacobs.

SPEAKER_01 1:35

Terry Jacobs is a little boy that was born in Georgia to uh to a uh dad who uh was an electrician for General Electric, didn't finish high school, neither did my mother, and had two kids, myself and my younger sister, who was three years younger than me. But he died when I was nine years old.

SPEAKER_02 1:56

Okay.

Football Dreams To Marine Corps

SPEAKER_01 1:56

And mother didn't have any kind of an education. We lost everything. He had a very good job working for General Electric, but he he didn't have life insurance. Uh what didn't seem important when you were 34 years old. Sure. Needed something for your family to fall back on. Weighed out on Labor Day in 1952. We lost our house, we lost our cars, we lost just about everything that you can lose. It was a tough life growing up without a dad. I ended up uh I I loved football. So I ended up playing on the local school teams and high school uh football. Wanted to go on to college and play football in college, but I had severe injury and knee injury when I was a senior in high school, and that ended that dream.

SPEAKER_04 2:48

Sure.

SPEAKER_01 2:49

Ended up joining the Marine Corps. I was good enough to go in the Marine Corps, but not good enough to play football.

SPEAKER_05 2:53

Yeah.

SPEAKER_01 2:54

I tell people outside of marrying my wife, which is a story all to itself. Uh was the best thing it ever did for me was join the Marine Corps because it gave me a a chance to get to to know things about myself that I never would know otherwise, and to experience things that I never would have gotten a chance to experience.

SPEAKER_05 3:17

Okay.

Discovering Actuarial Science

SPEAKER_01 3:18

And uh it taught me a lot about wisdom, character, what you can do if you really work at it hard enough and you're dedicated to trying to make it happen. That propelled me all the way through school in a very difficult profession called the actuarial career. Nobody even knew how to spell actuary when I first started, but uh I I was always good in math. I wasn't good at much else, but I was pretty good in math. That gave me the ability to to use that to go in and get a uh as as far as becoming a fellow of the Casualty Actuarial Society with a bachelor's degree and a master's degree in actual science. And became youngest senior officers in several major insurance companies that I would never would have gotten to have those opportunities had it not been for being in the actuarial profession.

SPEAKER_04 4:19

Sure.

SPEAKER_01 4:20

It was uh so it it allowed me to do a lot of things in my life, including be the entrepreneur that I ultimately always wanted to do. Sure. So that's who Terry Jacobs is.

SPEAKER_03 4:32

That's a great introduction, thank you. This is Dan the Road Trip Guy. Um and I love to ask, what was your first car?

SPEAKER_01 4:40

It was a 1940 Hudson Hornet.

SPEAKER_03 4:43

Hudson Hornet.

SPEAKER_01 4:45

It was a little coop. It didn't run when I bought it, uh, but we got it finally got it to run. And so that was my first car. And that was when I lived in Florida because my my mother remarried. You know, my as I said before, my dad died when I was nine years old. But when I was about uh 13 years old, she remarried.

SPEAKER_02 5:06

Okay.

SPEAKER_01 5:07

So it was in Florida, and he had a buddy in the Air Force. Uh we were at McDill Air Force Base in Tampa uh that owned this Hudson Hornet and wanted to sell it. So we paid$100 for it.

SPEAKER_03 5:22

A non-running car.

SPEAKER_01 5:23

Yeah, for a non-running, and we didn't do much of anything really except take a lot of money.

SPEAKER_03 5:29

Yeah.

SPEAKER_01 5:30

I I did get a chance to take it out a couple of times and uh uh do some things, but then you know my mother and my stepfather got into a terrible argument and she ended up separating from him. I moved them our our family uh back from Tampa to Decatur, Georgia. Okay. Because uh that was where my I really felt more comfortable and and had uh gotten a lot of my early education from the Decatur schools. Sure. So I had friends in school there.

SPEAKER_03 6:02

So did you sell that Hudson or give it away? I I left it. You left just left it. Let somebody else deal with it.

First Car And Moves

SPEAKER_01 6:12

We yeah, I left it and we took off and went back to Decatur. I d I don't know if anybody ever bought it from my stepfather or not, but I didn't have to deal with that. I just took off and left.

SPEAKER_02 6:25

Yeah.

SPEAKER_01 6:25

And I drove, I I didn't even have a driver's license yet because you had to be 16 to get a driver's license. And I hadn't turned 16 yet. We rented a truck, put all our furniture on that truck, and drove back to Atlanta, which I drove the truck, never having driven a truck before.

SPEAKER_04 6:43

Sure.

SPEAKER_01 6:43

And uh moved our family back to uh Decatur, Georgia, where I ended up graduating from high school, met my uh lovely wife. It set off a lot of things in our lives that made we we had a wonderful life, really.

SPEAKER_03 6:59

That's good. Thank you. Have you ever taken any epic road trips maybe with Susan or as a family? Is is there a trip that just sticks out in your mind as just one of those trips that you would relive or you do relive in your mind?

SPEAKER_00 7:14

A lot of our road trips with Pat and Wayne.

SPEAKER_03 7:16

Yeah. We used to go skiing. Skiing, okay, didn't know that. See, I'm gonna learn a lot of stuff today.

SPEAKER_01 7:24

They they lived up the street about four houses up, and they had a son that was uh a year older than Jeff.

SPEAKER_02 7:32

Okay.

SPEAKER_01 7:33

But Wayne and I got involved in coaching the Pee-Wee football teams. And I put we were involved together all the way through high school and even into some of the college stuff that I ended up doing. But uh I guess the most memorable ski trip we had was one when we had eleven people in a Ford van that made this trip uh driving from here to uh Colorado.

SPEAKER_02 8:04

Okay.

SPEAKER_01 8:05

And that was an experience that I don't think it'd be easy to repeat. But having 11 kids, including Lynn, who was only about two or three years old at the time.

SPEAKER_00 8:17

She was sitting on the ice chest.

Family Ski Trips And Memories

SPEAKER_01 8:19

Yeah. This would be if you wanted to see a a a group of people traveling, then everything we did was against the law because we had no safety protection.

SPEAKER_00 8:31

Well, they didn't require.

SPEAKER_01 8:32

No, they didn't. We didn't we didn't even have seat belts in this van.

SPEAKER_03 8:36

Yeah. So you know what? Uh we all survived those days, right? I mean, I grew up on a road trip laying in the floor of our car. You know, my brother had the seat. Yeah. We were driving to Florida and I'm laying in the floorboard. Uh so you know, we had a lot of that going on. Yeah. Oh, that sounds fun. Did you have a good ski trip once you got there?

SPEAKER_01 9:01

Well, we had never been skiing. It was our very first ski trip.

SPEAKER_03 9:04

Okay, let's take a trip and go skiing.

SPEAKER_01 9:08

And so, yeah, they they got us interested in this. And if we had to go to a ski store and buy things like boots. Sure. Buy our ski. We ended up buying our skis instead of renting them. But we had a that was a beginning of a wonderful relationship that lasted 20, 30 years with Smith. So we've got some great They took Jeff with them.

SPEAKER_00 9:34

Yeah. And he loved it. He was eight or nine.

SPEAKER_01 9:38

Yeah, he was eight, nine years old.

SPEAKER_00 9:40

Next year they said, Well, you guys go with us. We can ski.

SPEAKER_03 9:44

Now, did you start skiing then? I see. He did. Yeah. I did. Yeah.

SPEAKER_00 9:49

Easy slope. Skiing.

SPEAKER_01 9:51

Yeah. We've got some interesting ski stories too. Yeah, I bet. Where I convinced her to go down an an expert slope in a snowstorm because we couldn't get off the mountain otherwise. And she's never let me forget that. I'm sure.

SPEAKER_00 10:06

I always skied the easy roads, whatever, but I made a wrong turn one time and ended up like a double blank.

SPEAKER_03 10:14

And you're like snake. Gotta get down, right? Yeah.

SPEAKER_00 10:18

I was up there for 45 minutes. It was getting dark. The skiers would come flying by and fly through the air and land. And finally I said, uh gotta go.

SPEAKER_05 10:35

Yeah.

SPEAKER_00 10:36

So I prayed about it and finally did it, and I actually landed on it. Wow.

SPEAKER_01 10:43

Wow.

SPEAKER_00 10:44

But I didn't she I didn't go back out. Yeah.

SPEAKER_01 10:47

And she didn't speak to me for a long time.

SPEAKER_03 10:49

Yeah. Yeah. Oh, that's good. It's good to have those memories.

SPEAKER_01 10:54

Oh, it was. We we had some great time skiing with that family, and we're still close. Unfortunately, he's the one that died of a Parkinson's disease. But we still talk to Patty. She lives over or across from Muller High School now. Yeah.

SPEAKER_00 11:09

We've actually had a lot of good road trips, going to football games, recording games. Yeah. All over the place.

Meeting Susan And Young Love

SPEAKER_03 11:16

That's good. Yeah. Well, I didn't have the recorder going, and since you both are sitting here, how old did you all meet? Tell us that story.

SPEAKER_01 11:25

Well, I was, I don't know, 13 years old, maybe, 14. When I first uh w went into the uh uh Clark's music on the square indicator.

SPEAKER_02 11:37

Okay.

SPEAKER_01 11:38

And she was in there, she was working behind the the uh cash register, and I had enough money, I had saved up enough money cutting grass and doing all these things. I needed a baseball bat.

SPEAKER_02 11:48

Okay.

SPEAKER_01 11:49

Because I was playing on the little league team. Made the all-star team, by the way. I I she came up to me and said, May I help you? And I said, I'm looking to buy a baseball bat. And she said, Well, here are our baseball bats over here. So we went over and I can't I looked at her and said, This is a good looking little girl. And I said, I need to get to know her if I can. So we we got to talk and I bought the baseball bat. Then another week or so I go went back in there looking for something else. But I I would go in there periodically, hoping I could convince her. We had a local movie house that I could convince her to go to the movie with me because I didn't have enough money to do a real date.

SPEAKER_03 12:32

Right.

SPEAKER_01 12:33

That was uh uh I I tell her that was when I fell in love with you, those brown eyes of yours and her long ponysail. Interesting though, she's got dark hair and I got white hair.

SPEAKER_03 12:45

Yeah. Yeah. And that was and you've been married, I think you told me, 63 years. Yeah. Yeah. So now did you get married while you were in the Marines or was that? No.

SPEAKER_01 12:56

Uh we got married uh He was 20, I was 18. Yeah. We came I came back from Marine Corps, went to University of Georgia for a year hoping I could it'd be a walk on Detroit and get play football, still had that desire to play football. Ran out of money, didn't get a scholarship. Susan and I uh started dating. I I finally went to a party that I was crashing, I wasn't invited, but uh three of my friends and I went to this party at her uh one of her close friends' yeah house, big house up on a big hill. Uh she was there with uh one of the guys who was playing in a band.

SPEAKER_02 13:39

Okay.

SPEAKER_01 13:40

And so she didn't have anybody to talk to most of the night because he was playing in a band. So I took advantage of his his disadvantage and finally convinced her to go out with me.

SPEAKER_06 13:51

Yeah.

SPEAKER_01 13:52

And that was our beginning of our first day. We went to see Spartacus. Funny story about Spartacus.

SPEAKER_06 13:58

Yeah.

SPEAKER_01 13:59

I went with to see Spartacus with five different girls on five succeeding nights because they all wanted to see Spartacus.

SPEAKER_02 14:08

Okay.

SPEAKER_01 14:09

And by the And you were happy to go. I hated Spartacus.

Breaking Into Insurance Leadership

SPEAKER_03 14:17

You really hated it by the fifth showing, right?

SPEAKER_01 14:21

Yeah, but it was it was uh the start of something really good. So we dated throughout uh I I was going to school at night at Georgia State.

SPEAKER_02 14:30

Okay.

Big Bet With Prudential

SPEAKER_01 14:31

Because I transferred from University of Georgia. Uh I had r run into somebody that I went to high school with in the hallway. And he said, Terry, what are you doing? I said, I'm I'm going to school here at Georgia State. And he said, Well, what are you majoring in? I said, I have no idea. Maybe accounting. He said, Well, you're always good at math. Why don't you look into this actuarial program that I'm involved in? You were always good at math. And I said, What is an actuary? He says, Well, it's somebody that uh makes the rates, determines the liabilities that we have to put up. He said, It's a very strict profession, but it's very rewarding. And he said, and you should be able to do it. So I went and knocked on the door at the office of the head of the actuarial uh education department at Georgia State and said, I'm Dr. Zubay was his name, is Eli Zubay in uh Floyd Harbor. I said, I'm interested in the actuaril program. Would you have a few minutes to talk to me about it? So they said, yo, you usually what we do is we ask people to take this aptitude test to see if you're capable of passing the actual exam. So they say, would you have time to do that? So I said, got nothing else to do. So I took the actuarial aptitude test, and they advised me after consulting with each other not to do it. You didn't do very well on our aptitude test. I said, I never saw any of those problems. I said, I've never studied actuarial uh programs or math. And he said, Well, they said, well, people that don't do well on this test usually don't can't make it through the actuarial program. But he said, We'll let you come in if you you insist on doing it. But uh we advise you that it's probably not gonna be something you want to do. So right then I decided I'm gonna do this. Yes. I in enrolled in the uh actuarial program, and never forget the very first night of class that we had. Dr. Harper comes in and he says, My name is Dr. Floyd Harper, and I believe in the what what do you call it, something princip. And uh none of us knew what that was. He says, it's work, work, and more work. And I said, I can do that, but I don't know if I'll be able to do this. So I ended up transferring into the actuarial program, ended up passing the second test. There was a series of ten tests that you had to pass, actuarial exams. I passed part two before I passed part one. And they they then encouraged me, said, You can do this because nobody we've never had anybody do what you just did pass part two before passing part one. So to make a long story, after about six years of studying actuarial science, becoming the head of the actuarial club and being involved in recruiting and all of that, I uh ended up becoming an actuary. I was a uh an associate of the actuarial society by the time I got out of undergraduate school, which put me in a highlight of a lot of people who were looking for actuaries back then. It was a a rare opportunity.

SPEAKER_03 17:52

That was in the 70s, I believe.

SPEAKER_01 17:54

Well well, I graduated in 1970 with in with my master's degree. Okay. And uh I've got a plaque around here somewhere that's got my uh name on it in the year that I became a fellow. But that put me in a in a spotlight where a lot of people were looking at my I at the time I thought I was way behind everybody else, because all my friends had gone on, graduated and gone on to make get a major job, and here I was still going to school. So I thought I was behind everybody else, but all of a sudden I jumped to the head of the class when I uh passed those exams. And she was there with me helping me, encouraging me, yeah, sometimes discouraging me.

SPEAKER_02 18:38

Yeah.

SPEAKER_01 18:39

Uh because it was tough. It was we we had no family life. We got a grandson, Jacob, Lynn's son, who's becoming an actuary.

SPEAKER_04 18:50

Really?

SPEAKER_01 18:50

Yeah, and I I've advised him, I said, Jacob, this is a very difficult field. If you don't want to put the time in, don't do it because you'll be frustrated. I said, when I was uh taking the exams, I had to devote every minute that I could find to studying.

unknown 19:08

Yeah.

Cincinnati Call And Career Pivot

SPEAKER_01 19:08

And I said, it paid off for me. But unless you're willing to put the time in, don't do it because you'll be frustrated. Sure. Fortunately, he's passed four of those exams now.

SPEAKER_03 19:17

Good for him.

SPEAKER_01 19:18

And he's just got engaged. Okay. But he's a great kid. And he always said, I'm doing this because of my papa's an actuary.

SPEAKER_03 19:27

There you go. That's there's some legacy for you. Yeah. So you graduated?

SPEAKER_01 19:32

I went to work for a company that offered to pay my graduate school tuition while I was still at Georgia State. But the only uh thing that we had to do was make a commitment to move to Baltimore.

unknown 19:46

Okay.

SPEAKER_01 19:46

Because that's where they were located. It was a company called USF and G. And uh that's how we ended up getting to Maryland. But I I I graduated with a master's degree in actual science and the uh associateship degree. We ended up moving in July or August of uh 1967 to uh Baltimore, Maryland, actually Cockysville, Maryland.

SPEAKER_00 20:12

That was Jeff was born.

SPEAKER_01 20:14

Yeah, Jeff was born right before we moved. Okay. So when I got to to Baltimore, I was highly visible for being such a young guy with an associate's degree in actual science. And I did well pretty well in my job at uh USF and G. And I started getting calls from headhunters.

SPEAKER_02 20:34

Okay.

SPEAKER_01 20:35

I got a call from somebody that wanted to hire me at where was that, honey? That was The Little Aetna. The Little Aetna, Little Little Aetna, which was in Hartford, Connecticut. So they offered me m about a five thousand dollar raise over what I was making. Okay. Which was a lot of money back then. A lot of money back then. A lot of money. And so I said, we can finally afford to have an extra hamburger sometime. But I did very well there. I became the youngest officer in the history of the Aetna Insurance Company, which was like a hundred and fifty years old company. So they made a big deal out of that, and I got a lot of publicity for being so so young and being an officer of an old line insurance company that was very well respected. There's my doctor telling me I'm gonna take this pillow. She's very subtle.

SPEAKER_02 21:26

Subtle.

SPEAKER_01 21:27

But the most wonderful nurse I've ever had. So they get they get me to uh Aetna Insurance Company. And then uh an opportunity I thought of a lifetime came along because Prudential, which at that time was the largest insurance company in the world.

unknown 21:45

Okay.

Founding Jacor And Growth Strategy

SPEAKER_01 21:46

Or a life insurance company, but were founded in the 1700s. They had decided that they needed something to help their s their sales force sell more life insurance. So they thought they would get into the personal lines automobile. Homeowner's business, that that would be a good way for them to grow their clientele and uh the lines of business. They gave us$180 million to start a brand new company from scratch. And I was the third employee they hired. I thought it was an opportunity of a lifetime until I did one day I was working for some guy who was a uh the vice president in charge of the department that I was over. A very difficult person to work for, sure. To work with. And uh one day we were in a meeting and he said a bunch of things that I took as an insult and almost punched him out. Which I decided that that was not a good thing to do. Right. But I I told my the his boss was was a guy named David Sherwood, who later went on to become the chairman of the board of all prudential, worldwide prudential. But I told David that David, I cannot work with this guy. I'll I'll end up uh getting into a fight with him, which will create a problem for everybody and especially me. And so I said, I'm I'm gonna start looking for something else to do. He said, Oh, you can't do that. You're you're our youngest officer, you're you're highly visible, you got a great career here. And I said, I don't know if I can survive till next week with this guy. He tried to talk me out of it. He sent me to the chairman of the board's office, which was in Newark, New Jersey. They tried to talk me out of leaving, and uh uh I got a c a call one day from a guy named Ron Walker during this process. And Ron Walker was executive EP of American Financial Group. Okay. And somebody had recommended me. They had just bought Great American Insurance, and somebody recommended me. He says, is he here's a young guy that you really ought to look into hiring because we think he's gonna do great things. A guy named Ray Johnson was the one that I worked with at the Lil who had left and gone to work for Great American. So I I went back from a meeting with my then boss Paul Simpson, and there was a note on my desk when my secretary put a big star on it, and she said, Call this guy. His name is Ron Walker. And I said, Who is Ron Walker? And she says, I don't know, but he sounds important. So I called him back and he said, Terry, I'm Ron Walker. We're looking to build a new management team for this company that we just bought, and your name has been highly recommended to us several times. Would you be interested in coming to Cincinnati to talk to us about coming to work for us?

SPEAKER_04 24:46

Sure.

Deals, Debt, And WLW Purchase

SPEAKER_01 24:47

So I was in the right mood and I said, Yes, I would. Yeah. And so I ended up being invited by them to come back to Cincinnati. Uh ended up doing uh interviews with them, and they made me an offer I couldn't refuse. Sure. It was a big salary, big bonus, and a big car. And so that's how I came to work for American Financial. And I I I worked with them. The company that I was with that then was uh American Financials, Great American Insurance. Ron called me one day between the time I I had accepted the offer and before I had moved to Cincinnati. He said, uh Terry, I need to talk to you about something that's very critical. And so I said, Okay, and can we do it over the phone? He said, No, I want to do it in person. Okay. So I thought, oh well, they're changing their mind or something. So but I went back to Cincinnati and Ron Walker told me, Terry, if you're accepting this job because it's located in Los Angeles, company's not going to be located in Los Angeles. We're gonna move it back here to Cincinnati. And I said, I'm I double my uh commitment.

SPEAKER_03 26:01

Yes and yes.

SPEAKER_01 26:03

Turned out that that was a great decision. And we love Cincinnati and did very well here. So that's a lot of terror about Terry Jacobs that you may not have wanted to know.

SPEAKER_03 26:12

No. I think uh you know, I think the interesting thing about these recordings I've done with people, so many people have reached back out to me and said, Thank you for doing this. It's now left behind for my kids, my grandkids. At some point you had an itch then to uh you had that entrepreneurial itch. You you've got a great job.

SPEAKER_01 26:32

But at some point I want to be involved in doing my own thing. Sure. Took me two years to figure out what it was. Yeah. But it was the beginning of the start of J Corps. Yeah. I'd never been in the radio station before.

SPEAKER_03 26:45

Well, and what what uh led you to radio?

Exits To Clear Channel And Regent

SPEAKER_01 26:49

Glenn Mayfield. Did you do you know Glenn Mayfield? Glenn Mayfield's the father was uh Dr. Ma Mayfield of the Mayfield Planning. And uh Glenn Mayfield was had been a senior officer at First National Bank in Cincinnati. He went out on his own to uh to be a consult financial consultant, helping people start businesses and getting them financed. And he he was very instrumental in helping me decide what profession to get into. I told him uh the first time I met with with uh Glenn, I said, Glenn, I w I want to change careers and I want to start something that I can grow on my own. He said, Well, what what are your aspirations? I said, Well, if we could be the biggest in the radio business, that would be h be that would make me happy.

SPEAKER_04 27:36

Yeah.

SPEAKER_01 27:36

I said, but I understand there's a long way between here and there. Sure. He said, Well, I'd be happy to work with you. So we we did all kinds of planning and uh working on what what would be a good idea and and the radio business was perfect for an entrepreneur back then because you were limited on how many radio stations you could own. The way you grow a radio company was you had to you could only own uh seven AM radio stations and seven FMs.

SPEAKER_02 28:03

Okay.

SPEAKER_01 28:04

I had an opportunity to start off owning four. And the game back then was sell the small ones and buy bigger ones.

SPEAKER_02 28:12

Okay.

SPEAKER_01 28:13

So I eventually built JCOR into the eighth largest radio company in the country. It was very successful. We did a uh a public offering, which was unheard of back then. You didn't do small IV those like that. Sure. But we did one and we raised five million dollars with our first offer.

SPEAKER_03 28:33

Okay. And then sounds small today, wouldn't you? Yeah, yeah, yeah. Think about today, right?

Third Venture And Real Estate Shift

SPEAKER_01 28:39

It does, yeah. And then I had an opportunity to buy some uh some more radio stations. We we not only worked with Glenn, we worked with uh Mercer Reynolds, who is the owner of the St. Louis Cardinals, Bill DeWitt, had a company called Mer Reynolds and DeWitt, which was in the investment banking business. Okay. So they signed on with us and we raised$17 million. So we raised more money, and then we ended up we were buying stations and spinning off small ones and keeping the bigger ones. And then uh we uh we got introduced to uh Solomon Brothers, who did a$40 million uh public offering. We ended up buying uh WLW and W EBN.

SPEAKER_02 29:26

Okay.

SPEAKER_01 29:27

That was really the the send-off to bigger bigger opportunities, bigger money, more money. Unfortunately, I was able to borrow that money. Yeah. And that proved to be not something I wish I had done. But it was a it was an opportunity to work with the uh big capitalists on Wall Street and get to know a lot of the people in the business. So I I built that company to the point where we were very attractive to the outside world at that point.

SPEAKER_03 29:58

Okay.

SPEAKER_01 29:59

So we ended up selling it to Clear Channel. Where did they rank in the uh Clear Channel was number two. Number two. They gave me some stock and some other money, other opportunities, and I they sold me two radio stations to start my next company.

SPEAKER_03 30:15

Okay.

SPEAKER_01 30:16

Which was Regent Communication.

SPEAKER_03 30:17

I saw that. Yeah, I didn't know that.

SPEAKER_01 30:19

But so we built that company into a a very large company because the uh restrictions on ownership had changed from owning seven AMs to twelve AMs and twelve FMs. Okay. So you could be a much bigger company. Sure. And we did that. We we ended up owning the biggest companies, uh the biggest radio stations in Louisville, Dayton, uh Las Vegas, Atlanta, Tampa, Tampa, Florida. So we had some really big markets. That company became so attractive that Clear Channel, who we we had sold JCOR to, came along and said, We'd like to buy this company. And so I said, Well, we think it's too early to sell. And they said, No, we don't care. We like what you've done. So ended up selling the company to Clear Channel again. And then I started the third version of uh my radio venture, which was a big mistake.

SPEAKER_03 31:14

Okay.

SPEAKER_01 31:15

Quit while you're ahead, is what I should have learned.

SPEAKER_03 31:17

Should've listened to Susan, probably. Because she probably told you.

SPEAKER_01 31:20

We had a lot of money, could have lived a very nice life after what we had. But I was still ambitious, wanting to grow something. Yeah. Big mistake. But that ultimately led to our getting into the real estate business.

SPEAKER_03 31:34

Yeah, then you got into real estate. That's uh let's see, we got radio and we got real estate. And that went well.

Paying Debts And Protecting Reputation

SPEAKER_01 31:41

We did well in that. We we accumulated a lot of apartments. We got were in the home building business. Yeah. Jeff was very much involved in that. And uh we did we did pretty well in that until the market fell apart. Yeah. You know, that was after uh 911 and all this stuff. So the banks all decided they didn't have an appetite to do much of anything, much less help people build build companies.

SPEAKER_04 32:07

Yeah.

SPEAKER_01 32:07

So that was a start of a tough time. Yeah. And I ended up with a lot of debt and have been uh working very hard to the point where I can have it all paid off by the end of next year. Wow. Good for you. And it's millions of dollars.

SPEAKER_04 32:23

Yeah.

SPEAKER_01 32:23

A lot of people back because of my personal guarantees, and I didn't want to ruin my name.

SPEAKER_04 32:29

Yeah.

SPEAKER_01 32:29

Well, that's uh But we had enough money to keep this house and live a pretty nice life.

SPEAKER_03 32:35

Interesting story. Thank you for sharing that. That's uh quite a journey.

SPEAKER_01 32:40

Any fill-ins that you need.

SPEAKER_03 32:41

Yeah, I I did have one question I'd written it down. Uh Did you have a favorite radio station that you bought along the way? Was there one that just Atlanta. Yeah, it was your favorite. Yeah. It was my hometown. Yeah.

Favorite Station And Peak Moment

SPEAKER_01 32:54

I went back on top of the world down there. Interestingly enough, our high school union, yeah, the twenty-fifth year anniversary, was in Atlanta.

SPEAKER_02 33:04

Okay.

SPEAKER_01 33:04

And uh they introduced me at the dinner that night as the Radio Entrepreneur of the Year. Well I was Radio Entrepreneur of the Year two years ahead, but not that year.

SPEAKER_02 33:17

Yeah.

SPEAKER_01 33:18

But that was that was probably the time I felt I was flying the highest and felt good. Should have stopped then.

SPEAKER_03 33:25

Yeah. But I didn't. What would you tell a young person today if they came to you and said, ah, Terry, you know, I want to start I want to start a business. Uh what would you tell them?

Hard Truths For Entrepreneurs

SPEAKER_01 33:35

Told many people this. Well, you're gonna say that the hardest thing I ever did in my life was start a new company. And then I'm gonna tell you it's not the hardest thing you ever did. You're about to face the hardest thing you ever did. I said, You're gonna want to quit many times. You're gonna give up, you're gonna think that the financial world hates you, which they probably do. And I said, you gotta have an attitude I'm not gonna quit. I'm just not gonna give up. I'm not gonna I've had this dream and I want to follow it and I'm gonna do it. I said, It's the hardest thing you've ever done in your life except multiply it by two. And I said, and then the amount of money you're gonna need is gonna be the most money you ever did. And I said, But it's not. Multiply it by three. And then I say, You're gonna want to quit five or six times in this process, but you gotta say, I'm not quitting. And you gotta mean it. You're not gonna quit, so I'm gonna give up. That's the best advice I can give anybody who wants to be an entrepreneur. It's difficult.

SPEAKER_03 34:39

Yeah.

SPEAKER_01 34:40

Very hard.

SPEAKER_03 34:41

Yeah. Good advice. Yeah. From a guy who knows.

SPEAKER_01 34:45

Who's who's been there?

SPEAKER_03 34:47

So we mentioned Moorhead football earlier on, and so we mentioned Moorhead football earlier on, and yes, I was down there and I saw your name a few years ago. My wife and I went to Eastern, so Moorhead was a competitor. You're very active in I wish you hadn't told me that. Yeah. You know, there's those Eagles and those colonels, you know. You're very active in the school down there. Of course, you had two sons who played football there.

Saving Morehead Football

SPEAKER_01 35:14

Well, it was a s a situation where Howard was a very good football player in high school. And he got hurt. He hurt his he broke his foot his senior year in high school. He wanted to play college football and he was good. He was the his line coach in college told me that Howard was the best pass blocking center he had ever coached in his life. And he had coached a lot of NFL players. Jeffrey was very good, but not as big as his brother. Okay. But Jeffrey was quick and he was a hard worker, very strong. But when Howard got involved down there, the company the the uh college was going through a turmoil. They had had to fire a president of the un in university, and they brought in a guy named Reinhardt who uh came in from Slippery Rock, that which really is a name. Yeah, I think so. Slippery Rock University. They were having a a really tough time. They they started talking about, well, we'll just get rid of football, we'll stop playing football as a university. And I said, You got you got some great young kids here who deserve an opportunity. So this is the only way that a lot of these kids will ever go to college. And we can't give up and just turn them out to pasture and say it was a good idea, but it didn't work. So I went to work on raising money and improving the uh facilities. We put down artificial turf on the field. Yep. We built them a brand new uh weight room, we built them a uh brand new medical training room. Okay. Uh we built new offices for the coaches, and they ended up doing very well in the next year. As a matter of fact, they hold the record of the greatest comeback victory, double-A football in history. They were behind 35 to nothing to uh Wichita State University on a Saturday and came back to win that game 36-35. Wow. I got thrown out of that's the game I got thrown out of.

SPEAKER_03 37:12

I I was I didn't know if I was gonna bring that up, but we have a mutual friend who said make sure you ask him about that game. Because he said Mr. Jacobs wasn't only a supporter, he was very active during the games.

SPEAKER_01 37:24

Well, uh it's not the thing that I'm the most proud of, but uh I think I inspired them to go because I got kicked out of the game at uh halftime.

SPEAKER_02 37:33

Okay.

SPEAKER_01 37:33

And they came back in that next half and just took it to them.

SPEAKER_02 37:37

Yeah.

SPEAKER_01 37:38

It was probably the most satisfying time that we had been. Susan was there, we we chartered a play. And uh we flew there with them. Uh most of the team went on the on the plane with us.

SPEAKER_02 37:51

Yeah.

SPEAKER_05 37:52

Oh, that's funny.

SPEAKER_01 37:53

But it was a uh the and and we talk about it till now.

SPEAKER_03 37:57

Yeah.

The Legendary Comeback Game

SPEAKER_01 37:58

You know, everybody remembers that. I remember that Wichita State game.

SPEAKER_03 38:03

Susan, did you like football? Or were do you just that's probably good, right?

SPEAKER_00 38:10

Absolutely. Don't marry anyone if you like sport.

SPEAKER_01 38:13

Yeah.

SPEAKER_00 38:14

Don't marry anyone who does not like sports.

SPEAKER_01 38:16

Well, she turned out to be the mother of the team.

SPEAKER_00 38:20

Or if you love pets, don't marry someone who doesn't love pets.

SPEAKER_03 38:24

Yeah. So we're getting some marriage advice here in this episode. That's good. I like it. That's great. Thank you for sharing that. Imagine for a minute you could take a road trip, because it's just Dan the road trip guy, and you can uh anybody, living or deceased, who would that be? Where would you go? And what do you think you would talk about? And you can go with Susan.

SPEAKER_01 38:43

Ski ski trip. We had wonderful times on our ski trips with us with the Smiths. We all uh we had a lot of people join us on several of those trips almost for every year between nineteen I don't even remember when we started, but we had a ski trip with the family.

SPEAKER_05 39:00

Yeah.

SPEAKER_01 39:01

And we always loved that.

SPEAKER_05 39:02

Yeah.

SPEAKER_01 39:02

We'd all go out to dinner on night, sit around a fire and have a glass of wine.

SPEAKER_04 39:07

Yeah.

Marriage, Sports, And Life Together

SPEAKER_01 39:07

You know, those are wonderful times, and we s have stayed close friends with the Smiths. Unfortunately, Wayne died a couple of years ago. But his wife Pat has been a real friend of ours for a long time. I would say uh the o of the trips that we've taken, those were the most enjoyable ones. Yeah. We've never been travelers in terms of cruises. We've been on one cruise, she got sick as a dog, and we never got to go on another one.

SPEAKER_03 39:34

This has been great. One last question. And I might just ask Susan this question too. You you gave some business advice for an entrepreneur or a young person walks up to you, but as far as life, what kind of advice would you give somebody on just living a wonderful life?

SPEAKER_01 39:52

Always try to do what's right. Always try to do what's right. Even when it looks like it might not be the right thing. Because if you don't, your conscience will bother you the rest of your life.

unknown 40:04

Yeah.

SPEAKER_01 40:04

And it will always be something you'll regret. And there are a lot of things I'd go back and turn around the other and do it a different way. But I think that's the most best advice I could give anybody is no matter how hard it is, no matter how much pain it is, always do what you think is the right thing to do.

SPEAKER_03 40:22

Great advice. How about you, Susan? What would you tell people? He has been married a long time.

SPEAKER_01 40:28

Marry marry the right wife.

SPEAKER_03 40:29

Yeah, well, marry the right wife is a given.

SPEAKER_00 40:32

First of all, accept Jesus as your savior. You can find the Lord.

SPEAKER_01 40:36

Yeah.

SPEAKER_00 40:37

So important.

SPEAKER_01 40:38

There's another important thing. I was baptized in a Marine Corps swimming pool at Bears Island. Wow.

SPEAKER_03 40:44

That's yeah, thank you.

SPEAKER_00 40:45

Which it's gotten me through and us through everything. So it's very important.

SPEAKER_05 40:52

Yeah.

SPEAKER_00 40:52

And you have to have forgiveness.

SPEAKER_05 40:54

Yeah.

SPEAKER_00 40:55

Lots of love. It'll take a lot.

SPEAKER_05 40:57

Yeah.

Road Trip Wishes And Traditions

SPEAKER_00 40:58

And helps you get through. We've been through so much. But it's been a wonderful life.

SPEAKER_03 41:04

Sixty-three years. Sixty-three or four? Sixty-three. You're still sitting here together. Health is relatively good. Yeah.

SPEAKER_00 41:13

And it's taken the good Lord, lots of prayers.

SPEAKER_03 41:16

That's great advice.

SPEAKER_00 41:17

Many blessings. Realizing the blessings. Many miracles. Truly.

SPEAKER_01 41:23

Dan, we've evolved to the point where Susan and I pray together every night when we go to bed. Wow.

SPEAKER_00 41:29

Lots of prayers. Just realizing what the Lord has done for you and thanking him and being grateful and loving your family and your friends.

SPEAKER_03 41:38

And well, this has been great. Thank you. So much. Yeah. Well, we might do it again. Who knows? We might we we might just end up writing a book doing this, you know? So well. And this was a double treat with Susan being here. Uh I mean that in the world.

SPEAKER_01 41:56

Well, we've been through everything together, so so we know a lot about each other. Yeah. Having been through so much together.

SPEAKER_03 42:03

Um again, it's been probably twenty-five years, maybe. I don't know.

SPEAKER_01 42:10

Cool. Dan, thank you.

Life Advice And Faith Practices

SPEAKER_03 42:12

Thank you. This was so fun. Thank you for tuning in to Dan the Road Trip Guy. I hope you enjoyed our journey today and the stories that were shared. If you have any thoughts or questions or stories of your own, I'd love to hear from you. Feel free to reach out to me anytime. Don't forget to share this podcast with your friends and family and help us to spread the joy of road trips and great conversations. Until next time, keep driving, keep exploring, and keep having those amazing conversations. Safe travels. And remember, you can find me on the internet at DanTheRoad TripGuy.com.