Jason Shepherd: Chasing Dreams

Kentucky singer-songwriter Jason Shepard joins the Made to Make podcast to share his journey through songwriting, creativity, and building a music career while balancing family and a full-time job. (Sometimes two jobs!) In this inspiring interview, we explore his musical influences, creative process, the evolution of his sound, and how he stays committed to his artistic calling through setbacks and successes. 

In this heartfelt conversation, Shepherd opens up about the road that shaped his music—from early influences and first songs to finding his unique sound. He shares the stories behind his lyrics, how he navigates creativity alongside family life and a full-time job, and what failure has taught him about staying the course. If you’re a fellow creative chasing a dream in the middle of real life, this episode will inspire you to keep going.

Transcript

Shannon Grissom (00:00)
Welcome to Made to Make. Here we talk about creativity, the challenges that come with it, and why we keep showing up anyway. Because hey, we are all Made to Make.

Welcome to the Made to Make podcast. I'm your host, Shannon Grissom. Today's guest is Kentucky singer-songwriter Jason Shepherd Jason is a gifted storyteller with a tremendous knack for turning big cosmic questions into fabulous tunes. Welcome, Jason.

Jason Shepherd (00:36)
Thank you.

Shannon Grissom (00:38)
You know, I know you grew up in a musical household. Can you tell me what your childhood was like?

Jason Shepherd (00:45)
My mother played piano, played at the church and everything, and she taught lessons to a lot of the kids in the neighborhood, and I was too dumb to take them myself, I should have. And my father played in a bluegrass band with several of his friends, and they would play at community events and things, and seemed like they were playing all the time at the house. And in church, a lot of music in church.

Shannon Grissom (01:15)
It had to be a great environment to have me be surrounded by music. So when did you start? When did you take up guitar?

Jason Shepherd (01:24)
Well, I had some couple of false starts. I had a guitar as a young child and I tried taking lessons from a local young man and it just didn't work out. But then when I was in the service, I was stationed out in the desert and there was not much to do and I was.

just happened to be walking down the street and there was a music store and I said, I'm going to get a guitar and figure this out. It's long been long enough.

Shannon Grissom (01:55)
Wow ⁓

Jason Shepherd (01:58)
About a week after I bought it, we were playing in the service clubs on base.

Shannon Grissom (02:04)
Well, that's great.

Jason Shepherd (02:05)
The threshold for entertainment was pretty low.

Shannon Grissom (02:08)
Now, ⁓ I know you also play the harmonica, so when did that start?

Jason Shepherd (02:17)
⁓ My father had caught a harmonica that a player had thrown out and he had autographed the box and my grandmother had it in what they call a pie safe here. I don't know if they have that same type thing. She had it in the pie safe and I was told not to touch it, which made me want to play it even more. So anytime I got a chance, I would take that out.

and it was autographed and said Mama Blues on it and it had the artist's name and I can't remember what his name was but I was fascinated by it from the first time I touched it.

Shannon Grissom (02:54)
that's awesome. Did you have it with you when you were in the service?

Jason Shepherd (02:59)
yeah, I took harmonicas everywhere. I probably went to maybe 30 different countries and I'd say I played harmonic in half of them. I found that music, ⁓ even when you couldn't speak the language other people spoke, you could make music together and everybody would feel better.

Shannon Grissom (03:25)
So when did you start writing?

Jason Shepherd (03:27)
I started, I would write lyrics and figure stuff, little melodies and stuff out from the time I was a little kid, but I didn't have any way to make them into a song until much later. But I just always enjoyed lyrics. I found the way people use words fascinating.

Shannon Grissom (03:52)
So how do you come up with your songs? Is it the story first? What hits you first?

Jason Shepherd (04:00)
It really, it just depends on the song a lot of times. Sometimes I'll get like a ⁓ vibe in my head and I'll like hum it or whatever into my phone into a ⁓ voice note and then try to figure it out on guitar and I usually find out it's about the same chords I always use.

I can figure a way to fit that in just about every time. But sometimes it is the words, I'll hear something or read something. I think, man, that should be in a song somewhere.

Shannon Grissom (04:46)
Well, now as far as your style, have you evolved over time? I know right now, you your songs play jazz and you've got some funk and country and Americana all wrapped into, sometimes in the same song. And you use silence. I love how you punctuate certain passages with silence. That's just brilliant. So how did your stylistic mix evolve?

Jason Shepherd (05:13)
You know, it seems like whenever I'm trying to write songs, sometimes I'm not even trying to write them. It's like they just start bugging you and you're like, I gotta get this down. But I listen to a lot of Ry Cooder. I listen to Curtis Mayfield. I listen to John Prine and Tony Joe White and Johnny Cash. And it seems like that will influence how the song comes out depending on who I've been listening to.

Shannon Grissom (05:43)
Mmm. I get that. That happens to me with with paintings. I've been I see a certain artist I'm like, I love how they did that and

Jason Shepherd (05:53)
to try to copy them or anything. It just influences like them, know, how it comes out, I think.

Shannon Grissom (06:00)
Yeah, no, I think that's it. It's an unconscious thing. It just all of sudden poof and you're like, ⁓ wow, I see them there but I didn't know they were doing that.

Jason Shepherd (06:11)
I will get that, you know, at the end of the year, they'll have that little Spotify thing and it's like who you've been listening to and every time I'm like, yeah, that checks out.

Shannon Grissom (06:20)
You ⁓

So, fast forward to today, how do you balance writing, creative work with your full-time job family matters? So how do you work that all in?

Jason Shepherd (06:38)
But that's the hard part, because obviously I don't think I'll ever make any money playing music. I do it because I can't help myself. It's the best part of the day, or whatever. And there was a long time when I just had to set that aside and just do the grind, because we had four kids and I was...

I had a long commute and I was working two jobs and there wasn't a lot, it was a lot of have to, not a lot of want to. So now the kids are more independent and I can do the want to stuff now. ⁓ It's great.

Shannon Grissom (07:27)
So is that ⁓ one of your early songs Dreams was that influenced by that time by that?

Jason Shepherd (07:34)
⁓ That was exactly what I was trying to say. Don't forget about the want to, because you'll take care of the have to stuff, but make room for taking care of yourself too.

Shannon Grissom (07:51)
Yes. Well, I love that line. If we if we put our dreams upon the shelf, we lose the best part of ourself. It's like, ⁓ my goodness, that is so good. So, you know what? We're going to take a listen to that song right now.

Jason Shepherd (08:22)
If we put our dreams upon a shelf

the best part of ourselves.

Worry makes you lose your grip

settle for that easy trip

Maybe we all have to fall ⁓

Let us fall, chasing our dreams.

It won't seem so bad at all

They are all

that they seem

Our dreams are bigger than ourselves

They are sure Our greatest wealth

I wish you all the riches that they bring

My wish is that you live your dreams

Maybe we all have to fall

Let us fall, chasing our dreams.

Won't seem so bad at all

They are all

That they seem

I lost mine for a little while

When they were found I found my smile

In my dreams you have a part

in my dreams, you are my heart

Shannon Grissom (11:19)
you

Wow, that was great. And I also like the line, you know, maybe we all have to fall chasing our dreams. So what has falling or tripping taught you about, you know, about life and creativity?

Jason Shepherd (12:03)
I don't know about you, you know, I've probably written 500 songs and maybe 50 of them got finished, you know, to where I wanted them to be. And there's a lot of failure in there. But sometimes those failures will make another song better because of something that you figured out when you couldn't get that where you wanted it.

Shannon Grissom (12:26)
Yes, I have the same experience with the songs and with my paintings. I periodically throw them out. mean, they're just... just...

Jason Shepherd (12:40)
I'm talking about painting. I know that there are many famous works of art, that there's a painting underneath them. So there was a failure before there was that thing of beauty that you enjoy. There was a mistake.

Shannon Grissom (12:57)
That poppy in the background, that was red boots. There are a pair of red boots under that poppy. And you know what, it was a big canvas and ⁓ I thought, yeah, and it was expensive and I thought, I'm just painting over this puppy.

Jason Shepherd (13:15)
Exactly. mean, it's all a learning process. you know, when you can get them to come out the way you have them in your head, it's such a great feeling that it makes the failure seem insignificant, you know.

Shannon Grissom (13:38)
Well, I think you've had a lot of success. I'll send the link to your playlist later, but my goodness, you've got a lot of good songs out there. And I'm thinking about, ⁓ you've got some interesting backstories behind some of your music. And I'm thinking about Elegant Universe. So I gotta hear what sparked the idea behind Elegant Universe.

Jason Shepherd (14:05)
There was ⁓ an actor with Sam Shepherd, no relation to me, but he lived here for a while. And he was a drummer. He sat in with some friends of mine and played the drums, because he had been a drummer in The Fugs back in the 60s. Real interesting guy, real nice guy, but real quiet. And when he passed away, he was living over in Versailles, which is 15 miles from here or so.

I didn't know him well enough to be like heartbroken or anything, but I was like, man, he made some great art. And so I went back and watched The Right Stuff right after he passed. And I hadn't seen it since probably it came out. And I've gotten in a real bad habit of Googling stuff while I'm watching a program. so Cooper had talked about

⁓ I looked the astronauts up and everything and Cooper talked about seeing a UFO while he was in the service. And it said there's an interview about that in a documentary. I went and after I finished watching The Right Stuff I watched the documentary and one of the, pretty much all the lyrics come from that documentary. It was very strange to watch, but Cooper's interview, he said,

I saw this UFO, we made a video or a film of it. And he said, some guy shows up from Washington DC, they confiscate the film and he never, they told to never speak of it again. And Elegant Universe was a book mentioned in the documentary. ⁓

Out of the Blue, I think, was the documentary. Peter Coyote narrates it. It's very interesting to watch. ⁓ So that song came from Sam Shepherd passing away. Long way around the barn, but that's where came from.

Shannon Grissom (16:12)
Wow.

Yeah, you just never know what will inspire you. you know, the chorus wrestles with whether the unknown is a blessing or a curse. And so how do you weigh in on that?

Jason Shepherd (16:30)
Well, that's the mystery, you know. I know they talked, I don't understand the concepts well enough to explain them except very childlike, but they talked about that time may not be like linear, that it may be able to fold on itself and you know, all these different concepts of time and space that I frankly don't understand, but it's part of that mystery.

I just found it interesting.

Shannon Grissom (17:03)
It is interesting and so is the song. Let's have a listen to that right now. Elegant Universe.

Jason Shepherd (17:17)
I've heard credible observers of incredible things Like aircraft that can fly without any wings It's hard to come to grips with what you can't comprehend But what if time and space don't break but only then? I try not to think about it but I can't help but wonder

Is there something in all that nothing In the great blue yonder?

If there's something, is it a blessing or a curse?

For another unsolved riddle of an elegant universe.

Fighters back in World War II When Flyboy saw them come, they didn't know what to do They didn't talk much about it, afraid that they'd gone crazy All of their descriptions seemed purposefully hazy Are they close encounters of the third kind?

presidents and governors lost all of their minds? Have astronauts and pilots been in on one big scam?

Or did they see ships of strangers from a strange land? Mr. Starman Tesla hit that long lunar note and let it float.

we’ve had projects like Bluebook, Grudges and Sign spent millions just to say there was nothing to find But Bentwaters, Malmstrom and the Atlas film seemed true not conspiracy lunes looking for something out of the blue I try not to think it

But I can't help but wonder

Is there something in all that nothing in the great blue yonder

If there's something, is it a blessing or a curse?

Or another unsolved riddle an elegant universe.

Musically, that was very inspired by Ry Cooder. Ry Cooder played with Captain Beefheart when he was like a teenager on the album, Safe as Milk. And there's a song on there that Cooder did the arrangement for that I just found really interesting. And then the chorus kind of was influenced by Jimi Hendrix.

Up from the skies, know, bum, bum, bum, bum, bum, bum. Very much influenced by Hendrix, who I always really liked. I don't think I understand a lot of his music, but I like it.

Shannon Grissom (21:23)
So that I was going to ask how you landed on the mood because it's mysterious, reflective, it's it's it's you know all that with you know with that blues edge that's really subtle but it's there and so that that answers how you got there. Jimmy.

Jason Shepherd (21:41)
No, and I've just been so lucky. I met Richard Smith at the Kentucky Thumb Pickers Christmas party. And he said, I'm opening a studio and if anybody wants to come make a record, you know, a recording, talk to me and we'll work something out. And so I said, I've written a lot of songs, but I'm not a real good player. And he said, I got a lot of friends who are, you know, great musicians and

this is how much it would cost and whatever. And so, I mean, I'm playing with guys that I really have no business playing with. These are fantastic musicians. ⁓ And it's just stroke of luck, really. I mean, it just, I'm glad I took advantage of.

Shannon Grissom (22:29)
So how did that experience i mean you've gone several times ⁓ to Richard's studio so tell me about that experience how that had to feel tremendous what was that like.

Jason Shepherd (22:40)
It's, you know, I feel like these people are doing like, you know, the Mona Lisa or something. I'm doing cave paintings, but I will send, ⁓ you know, I'll figure out something on guitar and I'll record it in like garage band and I'll send it to Richard. He puts it in the Nashville System, you know, ⁓ which is, I,

I couldn't figure that out, but he puts it in there and they look at it and they can play it as soon as they see it. They're just great musicians. mean, it's like Rory Hoffman, he must play 20 different instruments and plays all of them just fantastically. And Pat Bergeson, he played with Chet Atkins and Jerry Reed and all those people. I'm like, and then he's got a slum and play with me. ⁓

Shannon Grissom (23:34)
Ha

ha ha.

Jason Shepherd (23:36)
Around here, always was a little bit probably overconfident that because I could, I'd play harp with anybody, play harmonica. I got down to Nashville and I heard those people that could really play. I was like, well, I better leave that harmonica at home. ⁓ that Pat played that. So I just, they play the music and I just sing, you know. ⁓

Shannon Grissom (23:51)
You

Well, I like your harp I've heard you. I think you're being hard on yourself.

Jason Shepherd (24:09)
No, I mean, I understand my limitations. I can play harp great for the stuff I'm writing, but I mean, these people can play. It's a whole different ball game. It's a very humbling thing. But I've enjoyed it every time. It's been a great experience.

Shannon Grissom (24:34)
I was also thinking about, well let's just, one other thing about the elegant universe before we move on. If definitive proof of extraterrestrial life came out, how would that change, do think it would change your perception of everything? What do you think?

Jason Shepherd (24:57)
I think just mathematically, it would be ridiculous to think that in the vastness of the universe that this would be the only place with life on it. That doesn't make sense to me. So I think there probably is out there, I doubt they'd want to talk to me. I don't think I would hold their interest.

Shannon Grissom (25:23)
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or a gentle reminder that you're doing way better than you think, you can find it on Amazon and it's there for those moments when you need support without judgment. That's the Sock Monkey Oracle. Find it on Amazon today. Now back to our show. Okay, one last song. I've also got to hear the story behind Pardon My French.

Jason Shepherd (26:16)
I was, as part of my military service, I was in Kosovo in 2019 and 20. And it was right before the pandemic started. I had planned to have my wife and daughters come over and my friend Sam, who I do a lot of really ridiculous stuff with, he and his wife and his sister had already planned to come to Paris.

His sister was obsessed with this Birkin bag, is an Air Me Farboard purse. I was shocked how much purses cost. So they're like, we're coming over. Can you meet us in Paris? And Shannon and the girls were like, I don't know, this whole flu thing that's going around, may not, we don't want to get stuck over there. Sam's like, well, we're coming anyway.

And so I was able to get a weekend pass and flights were dirt cheap from Kosovo to Paris. It was like 300 bucks round trip. And so I went over and met up and pretty much the whole song is just kind of our weekend right before the world shut down.

And ⁓

Shannon Grissom (27:37)
Well, you know, it's got a very jazzy ⁓ I got essence of Rickie Lee Jones No, okay, because because of the storyteller and the way the jazz flow through there

Jason Shepherd (27:54)
I mean, I've always liked her.

Shannon Grissom (27:57)
Yeah, she's great. And I just felt like ⁓ you had that vibe going in that song. It's a great tune. So we'll listen to that now. ⁓

Jason Shepherd (28:06)
you

Last time I was in Paris, a friend's sister's bobby was crazy about a purse. Hermes Farbourg kept it just out of reach, almost like a curse. Last time I was in Paris, I sang Brown Eyed Handsome Man to DiMilo's Venus. Even took a selfie with Bubba, she's right there between us.

Last time I was in Paris That cool jazz was hot In the fifth and one days more My friends were over in the first Just to cross the Notre Dame pont Ooh la la, c'est que c'est bon Ce n’est pas seulement une histoire grande

Last time I was in Paris, we made that Mona Lisa smile Even though a laser pointer made her eyes all green and wild Last time I was in Paris, I chased Amelie's shadow at Montmartre Lit candles for our families in that sacred heart

Last time I was in Paris, me, Bubba and Jenny rode Velos on the Champs Elysées Riding around the Arc de Triomphe was anything but easy Ooh la la, C’etais si bon Ce n’est pas seulement une historie grande bon

you ⁓

you ⁓

you

Last time I was in Paris, we ate steak tartare and suckling pig. The best scallops and crepes, we weren't eating beer. Last time I was in Paris, I played my old Kentucky home busking at the Louvre.

Did most everything an American in Paris could want to do. ⁓

Everything I say about the last time in Paris sure enough is true Even that the last time in Paris was the first time too Ooh la la

C’etais si bon Ce n’est pas seulement une histoire grande Excuse moi mon français

Shannon Grissom (32:06)
Wow, I really enjoyed that. So what's the one thing you would tell your younger self as you start your creative journey? What's the one thing you would want younger people to know when they get going?

Jason Shepherd (32:18)
never be afraid to take that leap. I'm so glad that I was able to meet these fantastic musicians and be able to take my songs further than I ever thought I really could. the rest of it's just...

marketing and sales and whatever, but there's just a joy in getting them to where you want them. And working with those people, they turned out better than I could have hoped. And that's enough. Don't get wound up on the stuff that is nice, but that's not the real point.

Shannon Grissom (33:07)
Yeah, I'd have to agree. I create because I have to. I'm not whole if I'm not creating. I am not nice to be around if I'm not creating. And so it's good for my soul.

Jason Shepherd (33:21)
It's a joy. I mean, it is just a joy. I, you know, I've always, the ones that I end up picking to finish, there's usually one that's like a local kind of weird story that I like, that I think, that's a story I'd like to tell. Almost always I do a song about faith or, you know, the doubts that come with faith.

And then, you know, there's always kind of one weird one out there that, you know, it's just that those are the ones that appeal to me. So that's the ones I record because I get to pick which ones I did.

Shannon Grissom (34:05)
Well, I love that you allow them to come out and don't filter you you know, you don't say this one's not commercial and this one's not this this one's not that you pick what resonates with you and you work with that and so that's authentic

Jason Shepherd (34:21)
That one song for his love, I was in church and we had a guest preacher and he was telling the story about this little bitty woman and she preaches to homeless people. So she lives or did, lived on the street and just the courage and the hope that she gave people. ⁓

I was like, man, there should be a song about her. So I wrote it and I was able to send it to her. And that was all the success that I needed for that song. I was like, that's just cool. And the Pardon My French, that was like a celebration of our trip. And so to be able to share that with Sam and his wife and sister, that was enough for me. I just thought that was cool.

Shannon Grissom (35:10)
That's great. It's so good for the soul. So where can folks hear your music?

Jason Shepherd (35:17)
Right now it's on that SoundCloud link. I do have, put Pardon My French on Spotify and Apple and all that. And as soon as I, you know, I have, I don't know, 34 songs recorded, but I need to get them mixed and mastered. And so I'll slowly start putting them on those other services as I'm able to. I went to a songwriting camp and you know, a lot of it, it's just not like...

man used to say around here, I ran out of knowing what to do. ⁓ I didn't know what to do with them. I had them recorded and I was happy with them, but I didn't know what's next. And I went to a songwriting ⁓ weekend and a lady from that experience has been kind of mentoring me on, hey, you should do, know, try this. And so that's how I ended up with those things on Spotify and whatever. And I'm gonna.

continue to try to release those as I can. And I'm sure that it won't make a ripple in the big pond, but it'll be cool.

Shannon Grissom (36:28)
There are people out there that need to hear your music and I'm happy to be able to share it. Wow. Well, do you have any parting words for songwriters or anybody who's creative and...

Jason Shepherd (36:43)
Well, I can't finish it without saying that you and I did a record together. We did. Virtually We did. it was usually, don't know, that camp was the first time I tried writing with other people, or, you know, not the first time. I've done, like, there's a gal around here who, she and I will text lyrics back and forth to each other, and then sometimes they'll end up being.

Shannon Grissom (36:51)
Hey

Jason Shepherd (37:11)
whole songs and sometimes it's just an exercise in playing with words. But you and I did, like, I would do my part and I'd send it to you and then you would take it to someplace that was way different than where I was. But it all turned out really neat, I thought.

Shannon Grissom (37:30)
Yeah, I thought so too. It's just the collaboration is just it's so wonderful because there are things that when you work with other people, they think of things that they're in a different vein and then you, you know, work them back and forth. So it's great that you have people and you're continuing to do that. I mean, it just ⁓ I think.

working with other people helps you and inspires me to keep going and keep creating when you might be, I might be dragging and tired and poopy and I'm like no, it helps light a fire under people so that's good. Well you're totally an inspiration, I can't wait to share your music with people. Thank you everybody, thank you Jason for being here.

And please be sure to like, subscribe and share so that I can make more of these and inspire you all. That's a wrap. We'll see you next time.

Jason Shepherd (38:27)
you