Richard Wilmore: Podcast Stories That Build Connection

Wendy & Rich 0:01
Coming to you from the Freedom Federal Credit Union Studios Hartford County Living Presents, Conversations with Rich Bennett. 

I love it! I love it! I love it! I love it! I love it! I love it! I love it! I love it! I love it! I love it! I love it! I love it! I love it! "I love it!" (Laughter) I never went off to watch. I want to be with you today. It's kind of a few seconds of hours of work. And I can't do it. It's kind of a little bit of a little bit of a bit of a... It's fun to watch. It's fun to watch! 

Rich Bennett 0:27
It's fun to watch! It's fun to watch! It's fun to watch! It's fun to watch! It's fun to watch! It's fun to watch! It's fun to watch! Some people spend their life searching for their calling. Richard Wilmore discovered his while watching a rerun of the Rosio Donnell show in the summer of 1997. What he saw was more than entertainment. He saw how one person could create a joyful, judgment free space where others felt seen, heard, and valued. That moment inspired a kid in Wisconsin to transform his bedroom into a television studio and begin practicing for the career he hoped to have one day. Since 2011, Richard has hosted and produced thousands of episodes of award-winning talk shows and podcasts, led in arts and health non-profit, and even learned the art of connecting with strangers from behind the wheel of a fashion truck. Today, through Make Your Day, Richard uses more than 15 years of media experience to help experts uncover the story that makes them unforgettable, prepare for meaningful interviews, and reach audiences who are ready to listen. But, he turned a childhood dream into a lifelong mission, and what separates someone who is simply talking from someone people genuinely remember. And those of you listening, if you've been listening to the show for a while, you remember, Richard, because he's been on... Alright, so the last time you were on with six years ago... 

Richard Wilmore 1:56
Yes. 

Rich Bennett 1:56
And I think I surprised you because Stacy came when it was for your birthday. 

Richard Wilmore 2:02
But 

Rich Bennett 2:02
I do believe you were on two or three other times before then. 

Richard Wilmore 2:08
I... in person, 

Rich Bennett 2:10
Yes. 

Richard Wilmore 2:10
yes. in real 

Rich Bennett 2:11
Yes, 

Richard Wilmore 2:11
life. Yes. Yeah, we did a cook, yes. I real life. 

Rich Bennett 2:14
Those of you listening right now, this is AI Rich and AI Richer. 

Richard Wilmore 2:19
Not another life, just real life. So the two different 

Rich Bennett 2:23
things. Now, here's the scary thing because we're going to be talking about podcasts and then guest scene and everything. And... in the green room, I mentioned how I was on mouthful graffiti, Brad Cox's, and it just felt we're being in the guest scene. If I'm not mistaken, your podcast was the first time I ever guessed it, and that was nine years ago. And your basement when you lived in Maryland. 

Richard Wilmore 2:51
Yeah, yeah, yeah. Oh, I remember that was... I loved my studio. 

Rich Bennett 2:55
Yeah, but nine years ago. 

Richard Wilmore 2:57
That's a long time ago. 

Rich Bennett 2:58
I know. It's crazy. It's 

Richard Wilmore 3:01
I've... 

Rich Bennett 3:02
not. It's not that you had me on first of all. 

Richard Wilmore 3:04
Well, because I thought you were doing something similar to what I was doing. 

Rich Bennett 3:09
Right. 

Richard Wilmore 3:09
You and I thought, well, what are the chances? One, that someone's so close and such a 

Rich Bennett 3:15
In a local 

Richard Wilmore 3:16
remote... 

Rich Bennett 3:16
area. 

Richard Wilmore 3:16
Remote, yeah. Would be doing that and I just thought what you were doing was great, so I wanted to talk to 

Rich Bennett 3:21
Yeah, 

Richard Wilmore 3:21
you. 

Rich Bennett 3:22
and that was... the good thing is you made it comfortable. I got it. Which made it easy for me, because there are other shows I've been on, and it's like, I'm a nervous wreck. Even before Brad's, I was a nervous wreck. My wife kept saying, "Why are you so nervous?" It's like, I'm not used to this. 

Richard Wilmore 3:40
Yeah. 

Rich Bennett 3:40
I'm not used to being in the other... the chair on the other side. All right, so... 

Richard Wilmore 3:44
Control. 

Rich Bennett 3:45
Last time you were on, you were in Texas. 

Richard Wilmore 3:47
Uh-huh. 

Rich Bennett 3:49
If... actually, I'd... well, let's see. So you went from Maryland, Wisconsin, Maryland, South Carolina, right? And then to Texas. 

Richard Wilmore 3:57
No, I went to Maryland to Texas to where I'm at now. 

Rich Bennett 4:00
Where you at now? 

Richard Wilmore 4:01
South Carolina. 

Rich Bennett 4:02
Uh? 

Richard Wilmore 4:03
Yeah. It ended in South Carolina. You just put it in the wrong spot. 

Rich Bennett 4:07
I thought I could have sworn you were in South Carolina or in North Carolina before Texas. 

Richard Wilmore 4:11
No. I was... I was with you. 

Rich Bennett 4:14
What? Well, what drew you to South Carolina? 

Richard Wilmore 4:17
I'm kind of throwing a dart at a map. We had 

Rich Bennett 4:22
Okay. 

Richard Wilmore 4:22
never... Ben here before. 

Rich Bennett 4:24
Right. 

Richard Wilmore 4:24
We had about a house without seeing it in person. Yeah, it just felt like we made a list of places we would want to live. 

Rich Bennett 4:35
Right. 

Richard Wilmore 4:35
was time to leave Texas. 

And Charlotte was one of them. And so we're like 40 minutes outside of Charlotte. 

Rich Bennett 4:43
It 

Richard Wilmore 4:45
And in about two months, we had a house sold in Texas, packed up and moved here. 

Rich Bennett 4:50
That fast. 

Richard Wilmore 4:52
Yeah. It went really fast. 

Rich Bennett 4:53
Alright, so, because I was just talking to somebody, and apparently this is a problem in Texas, mainly Arizona. Uh... no, you were in Austin, right? 

Richard Wilmore 5:03
I was in San 

Rich Bennett 5:04
Antonio. I knew that, I was gonna say that. But did you experience any of the killer bees that they have out there now? The African bees. 

Richard Wilmore 5:28
Oh, I was just gonna say, I thought the cockroaches in Texas were bad. I... those things are disgusting. 

Rich Bennett 5:32
Do you put saddles on them? 

Richard Wilmore 5:35
Yeah, you can hear them. I remember when I lived in my apartment, I could hear them hitting the siding outside. 

Rich Bennett 5:41
Ooh! 

Richard Wilmore 5:42
Yeah, they're huge. Huge. 

Rich Bennett 5:45
What the hell? 

Richard Wilmore 5:46
I don't know. 

Rich Bennett 5:47
That's nuts. 

Richard Wilmore 5:48
It's 

Rich Bennett 5:49
Alright, 

Richard Wilmore 5:49
gross. 

Rich Bennett 5:49
so since the last time I taught you six years ago... What has Richard been up 

Richard Wilmore 5:56
to? Let's see, six years ago. So I would have... what have I done since then? I moved... Was I divorced yet? Yeah, I was probably... 

Rich Bennett 6:07
Yes, I believe you were. 

Richard Wilmore 6:08
Years ago, uh... I quit a job that I thought I would have for the rest of my life. I started... I literally... I quit my job without a backup plan, 'cause it needed to happen. 

Rich Bennett 6:26
Right. 

Richard Wilmore 6:26
And I... I literally sent in the resignation letter and said, "Well, I guess I'm a full-time podcast producer now..." And that's what I've been able to do. 

Rich Bennett 6:36
It occurred me if I'm wrong, but do you just go somewhere to be on a game show? 

Richard Wilmore 6:41
Okay. Yes, I'm not at liberty to discuss it. However... Um, I did go on a game show. That's a national TV show 

Rich Bennett 6:55
Right. 

Richard Wilmore 6:55
that you'll be able to watch. We're trying to figure out how to do a virtual watch party when it comes on. I don't know when it's coming out. 

Rich Bennett 7:03
Ooh, 

Richard Wilmore 7:04
they're supposed to be filling us in as soon as they get the 

Rich Bennett 7:07
of... 

Richard Wilmore 7:07
schedule 

Rich Bennett 7:08
Right. 

Richard Wilmore 7:08
And then I'll let everybody 

Rich Bennett 7:09
Well, 

Richard Wilmore 7:10
know. 

Rich Bennett 7:10
you gotta let me know about that virtual watch party. Give me a fun. 

Richard Wilmore 7:13
Ye. Yeah, yeah. And what I found out is that... If you win And I can't tell you if I did or 

Rich Bennett 7:22
money... 

Richard Wilmore 7:22
not. 

Rich Bennett 7:22
Right. 

Richard Wilmore 7:22
But if you won money... You don't get... They send a check 120 days after your episode airs. 

Rich Bennett 7:31
What? 

Richard Wilmore 7:33
Yeah, so if you're thinking about going on a game show next week to fix your car, that's not how that works. 

Rich Bennett 7:40
So, but you had to pay your expenses too to get there and everything, right? 

Richard Wilmore 7:45
Yeah, I got off a towel. 

Rich Bennett 7:48
hopefully you won and you can be reimbursed 120 days after your 

Richard Wilmore 7:53
So 

Rich Bennett 7:53
episode 

Richard Wilmore 7:54
120 

Rich Bennett 7:54
air. 

Richard Wilmore 7:55
days. I don't know if that's all of them but 

Rich Bennett 7:56
Right. 

Richard Wilmore 7:56
that's how this one works. 

Rich Bennett 7:57
Wow. 

Richard Wilmore 7:58
Yeah. But because there's so many reasons between now and an air date, a year from now. Or that could change that it doesn't air. And so if your episode doesn't air, then you don't get the money. 

Rich Bennett 8:10
Wow. So even if you didn't win... 

Richard Wilmore 8:16
Wait, what? 

Rich Bennett 8:16
All right, you said if the episode... So if you win, you get the money 120 days after the episode 

Richard Wilmore 8:21
Mm-hmm. 

Rich Bennett 8:21
airs. 

Richard Wilmore 8:22
Mm-hmm. 

Rich Bennett 8:22
But if you didn't win, do you still get money for becoming on after the episode airs? 

Richard Wilmore 8:28
If you didn't win any money, no. You don't get like money just to show up, no. 

Rich Bennett 8:33
Who could happen to the days of a... You know, just a price for me 

Richard Wilmore 8:38
Yeah. 

Rich Bennett 8:38
and there. no. If it 

Richard Wilmore 8:40
No, 

Rich Bennett 8:40
was like a lifetime supply of hot dogs or something... 

Richard Wilmore 8:43
I know. We were even looking up, like, what are the tax rules, you know, on like Wheel of Fortune 'cause you can win so much money on Wheel of 

Rich Bennett 8:50
Yeah. 

Richard Wilmore 8:50
Fortune. And, I mean the taxes are so high most people, you know, just give it back 'cause they can't afford it. 

Rich Bennett 8:56
Wow. I didn't do that. Yeah. All right. So let's get into the podcast and... 

Richard Wilmore 9:00
Okay. 

Rich Bennett 9:01
100 different questions here, Ri. 

Richard Wilmore 9:04
I am scared 'cause you're the one that knows it all. 

Rich Bennett 9:06
No idea. I haven't looked at any of these questions. 

Richard Wilmore 9:09
Oh, where there's like a quiz? 

Rich Bennett 9:11
Well no. So remember when I was on your show nine years ago? 

Richard Wilmore 9:15
Yeah? 

Rich Bennett 9:16
Do you remember what you did at the end? 

Richard Wilmore 9:18
Yeah, we played a game. 

Rich Bennett 9:19
Yeah, which I didn't know we were gonna do. 

Richard Wilmore 9:22
Okay. 

Rich Bennett 9:22
th-- But 

Richard Wilmore 9:22
Yeah. 

Rich Bennett 9:23
that's okay. So pick a 

Richard Wilmore 9:24
Oh, 

Rich Bennett 9:24
number 

Richard Wilmore 9:24
I was 

Rich Bennett 9:24
between what and 100? 

Richard Wilmore 9:26
21. 

Rich Bennett 9:28
21. 

You know what? And this is perfect. And I know you have a good answer for this because you're good at this. What is a storytelling trick or editing technique that you think instantly ruins a good conversation? 

Richard Wilmore 9:58
I had a couple answers, but I feel like the one that popped in my head was what ruins it for me in this format is when either party cuts the person off and goes on a different tangent. And there's no, and there's no follow up if you have a, if you are trying to tell a story and if it's a good story and then you just go 'oh!' and then you move on. 

Rich Bennett 10:24
Right. 

Richard Wilmore 10:25
Yeah. 

Rich Bennett 10:25
Well, ehm, I think a lot of people, especially guests, again, come on other podcast and I always say this even about business owners and entrepreneurs. Storytelling's important. And 

Richard Wilmore 10:38
Yeah. 

Rich Bennett 10:39
everybody should be getting on podcast and telling their stories 

Richard Wilmore 10:43
and 

Rich Bennett 10:44
you've been producing for years. I mean, how many different stories have you heard? 

Richard Wilmore 10:50
Yeah, yeah. I would add to that, like, maybe not tell all of your stories. 

Rich Bennett 10:56
Oh, yeah. 

Richard Wilmore 10:57
Because that's a whole different route, especially with like, nonprofit people, they think, you know, you have to know everything that they've 

Rich Bennett 11:02
said. 

Richard Wilmore 11:03
ever 

Rich Bennett 11:03
Yeah. 

Richard Wilmore 11:04
And that, yeah, also, as does the opposite of what you think it's going 

Rich Bennett 11:07
do. 

Richard Wilmore 11:07
to 

Rich Bennett 11:08
Tell the important stories because as you know, even with a nonprofit, uhm, a lot of times the people want to know the person behind it. So tell the important stories that really highlight you so people will donate to that nonprofit. Don't tell them you spent 20 years in prison for something or another. 

Richard Wilmore 11:33
Yes. Well, yes. Yes. Or, yeah, or like, yeah, or everything. I think there could be an oversharing. 

Rich Bennett 11:40
Yes. 

Richard Wilmore 11:41
And then by the end of the episode, a listener doesn't know what they, what the takeaway is or what they should be what the action item is because you've said everything you've ever done in your entire 

Rich Bennett 11:51
Right. 

Richard Wilmore 11:51
life. 

Rich Bennett 11:53
Or you, and you get guests booked on other shows. Do you, so do you actually sit down and like consult them and stuff like that in the storytelling? 

Richard Wilmore 12:02
Yeah. So, one of the, yeah, like my, my starting process is like meeting with them 

Rich Bennett 12:08
Right. 

Richard Wilmore 12:08
and figuring out what they're going to talk about anyway. Like, what is or do you have a personality to be on a podcast? 

Rich Bennett 12:14
Yeah. You know, 

Richard Wilmore 12:14
do you have enough to say is do you know how to tell that story? So that's the first, I mean, that mistake of not doing that. And 

Rich Bennett 12:22
you 

Richard Wilmore 12:23
learn, you live and you 

Rich Bennett 12:25
You 

Richard Wilmore 12:25
learn. 

Rich Bennett 12:25
do. 

Richard Wilmore 12:26
Especially. Yeah. Uh, so yeah, that's exactly what I do. 

Rich Bennett 12:30
I'd say rich, pick another question. I mean, picking. Yeah, another number. 

Richard Wilmore 12:34
Um, uh, 40. I just turned 42. So 42. 

Rich Bennett 12:38
Wait 

Richard Wilmore 12:40
a minute. What? Yeah. Well, I don't know when this is coming out. 

Rich Bennett 12:42
you 

Richard Wilmore 12:42
But 

Rich Bennett 12:42
just turn 42. Really? Well, happily birthday. Have I missed 

Richard Wilmore 12:48
that? I don't 

Rich Bennett 12:49
know. 

Richard Wilmore 12:50
You're busy. 

Rich Bennett 12:52
Okay. So again, relate to podcasting. What is the true measure of success for a creator? 

Richard Wilmore 12:59
Oh. 

Rich Bennett 12:59
Numbers, impact or personal fulfillment? And why? 

Richard Wilmore 13:05
I think it. I think it's like, why I just start doing this. 

Rich Bennett 13:09
Yeah. 

Richard Wilmore 13:09
You know, and I think I talk about this a lot of like what? What? What is success in your podcast? Like when I first started. I would sit in front of YouTube and just refresh refresh. Then I'd be like, why is no one like? 

Rich Bennett 13:24
Yeah. 

Richard Wilmore 13:24
How come no one's watching? Um, but then I had other goals of like, I wish I could do this in front of an audience. And then when I moved to Texas, I got to do that. 

Rich Bennett 13:34
Right. 

Richard Wilmore 13:34
I had, I did it at a comedy club. And in that moment like that, five years before that, that would have been such a huge success. 

Rich Bennett 13:42
Right. 

Richard Wilmore 13:43
And then in that moment, it was like, well, how come you didn't sell any, well, how come you didn't sell enough tickets to sell up? You know, like then there was like an added word. It's only successful if. And I think in this space, we can just keep raising that bar every single time. And so really I've learned to like get excited about a success like 

Rich Bennett 14:03
Yeah. 

Richard Wilmore 14:03
that. I want it. And then not just going to the next thing because you've got to put out another episode or go on another show. Like it's, I think defining what that is, especially in a world of like celebrity driven podcast now that are, they're making 30 million dollars a year. Well, I mean, come on. You know, like, do I want to do that? Maybe, I don't know what comes with that 30 million, but like that's not success for so many podcasters, but, but there is success in 

Rich Bennett 14:34
other thing is, too, when you talk about those celebrity, who's the podcast and all honesty, I think that's a fact, I don't think it's going to last too long. You're already seeing problems pop up with the podcast, if you want to call podcast on Netflix. 

Richard Wilmore 14:53
that. The 

Rich Bennett 14:54
And even there was one just on YouTube, got bad. The guy has no. Podcasts, you saw the parent that 

Richard Wilmore 15:02
yeah, 

Rich Bennett 15:03
yep has no idea why you got banned and can't get in touch with anybody. And now, granted, that's not a celebrity driven pie case, but still. But you were

I think the other thing is too, and you and I knew it is, podcasting is, to start a podcast, it's still tougher, harder than starting your own business. What is it? I think it's less than 6% of podcasts out there are successful for independent podcasts. 

Richard Wilmore 15:34
Yeah. 

Rich Bennett 15:35
And I think too many people that get into it, focus on the numbers at first. They're looking at the downloads, they're looking at the views, they get discouraged, and they quit. 

Richard Wilmore 15:45
Yeah. 

Rich Bennett 15:47
And, yeah, so you have to know why you're getting into it at first. And I still think to me, the biggest reward, yeah, the sponsors are nice, it's great. 

But I still think the biggest thing that I get from it, at least, is when a listener contacts you, 

'm. 'm. 'm. 'm. 'm. 'm. 'm. 'm. 

Richard Wilmore 16:17
'm. 'm. 'm. 

Rich Bennett 16:17
'm. 

Richard Wilmore 16:17
'm. 'm. 'm. 'm. 'm. 'm. 'm. 'm. Yeah. 

Rich Bennett 16:19
And I'm sure you've ran into that a lot. It just, it worms your heart, you know? 

Richard Wilmore 16:26
Yeah. I mean, to me, I've only done it. It's all about connection to me. And so, I've been able to do that for so long and the same thing. I know that people have gotten jobs because of someone that they saw as a guest on my show or show I produce. Like, that to me, I mean, maybe a finder's fee would be nice, but I love that I get to do that. 

Rich Bennett 16:51
Yeah, oh, absolutely. All right, you ready for the next one? 

Richard Wilmore 16:56
Okay. 

Rich Bennett 16:56
Give me another number. 

Richard Wilmore 16:58
My dad just turned 69, so I'll take 69. 

Rich Bennett 17:04
69. Good number. Good year. Good cars. 

Wow. All right. Man, this is a deep question. 

Richard Wilmore 17:19
Uh-oh. 

Rich Bennett 17:21
What is the psychological weight of carrying other people's vulnerable stories and traumas out into the world? 

Wow. 

Richard Wilmore 17:32
We did a lot of work when I was at the nonprofit about that because we were working with people who were probably not going to leave the hospital. And walking into a room, knowing that, you know, and we know that they know that, but you're still there to provide joy. 

Rich Bennett 17:52
Yeah. 

Richard Wilmore 17:53
And maybe some laughter or a smile or something. And we're often the only people. We were often the only person that that patients would see because they didn't have family because they were too far away. You know, they didn't. And so we heard a lot in there about all of that. And so it's, it's, um, I don't know. I would guess we, we build up the same thing as like nurses do, right? Like we, there's so much incoming. 

Rich Bennett 18:21
you 

Richard Wilmore 18:21
How do 

Rich Bennett 18:22
do 

Richard Wilmore 18:22
to yourself? Um, and I've learned that it's just like, it's not my weight to carry. 

Rich Bennett 18:28
Right. 

Richard Wilmore 18:28
sense. Like one of the things we taught a lot was like, do not become friends on social media with your patients. Do not 

Rich Bennett 18:36
Makes 

Richard Wilmore 18:36
take phone numbers because your world is just going to be, uh, bombarded by that. And we had a patient. Who was there? She had her pets at home. And no one looking after them. She didn't have anybody. 

Rich Bennett 18:50
God. 

Richard Wilmore 18:50
And in the moment, I remember the artist who's super like she's, she's a visual artist and she feels so deeply. She was like, there was a moment where I was like, well, what's your address? Let me go check on them. 

Rich Bennett 19:02
Right. 

Richard Wilmore 19:02
Um, but then she was like, I can't, I can't, you know, I had, I didn't say that, but I wanted to so badly. 

Rich Bennett 19:09
Yeah. 

Richard Wilmore 19:09
I knew that was going to cross that boundary. And it's not my, it's not mine. Like as much as I feel for her, it's just not mine to do. 

Rich Bennett 19:18
Well, it could be a liability issue, too. I mean, it's, yeah, how many times have you actually, especially at the hospital, when you were finished and you just needed to clean next? 

Richard Wilmore 19:32
Oh my gosh. I literally, for the, literally for the first year, I worked there every day. Would you find me in some closet, somewhere, or so I had my car. I cried every day. 

Rich Bennett 19:43
Yeah. 

Richard Wilmore 19:43
And then eventually you do kind of, I don't know, build up a tolerance to it. I don't know if that's good or bad. 

Rich Bennett 19:52
No, because you know deep inside you still had the feelings there. 

Richard Wilmore 19:56
Uh-huh. 

Rich Bennett 19:56
I mean, just me from knowing you all these years, it's great. It may not show on the outside, but you're still feeling it in here. And I think that's what helps tell the stories even better. 

Richard Wilmore 20:09
Yeah. 

Rich Bennett 20:10
Uh, yeah,I  can't tell you how many times, you know, while I've been recording somebody's telling their story, and I'm literally crying. because it is, it's touching, but... At the same time, if I wasn't a granny, I know my Parkinson's in the audio, but you can tell when somebody's crying even and people can sense that and they feel that and I think it makes them more genuine that way as well. But man, I didn't, I forgot about that for you being at the hospital, that had to be hard. 

Richard Wilmore 20:46
Yeah, but then I mean, you really have to flip it into like, you know, what are we giving? 

Rich Bennett 20:54
Exactly, yeah. 

Richard Wilmore 20:55
How is that changing and suddenly they're not having the most depressing moment of their life, you know, and that was important too? 

Rich Bennett 21:02
Well, the other thing is too, I mean, how many people have you were you able to help doing that? 

Richard Wilmore 21:07
oh my gosh, I mean, literally thousands of 

Rich Bennett 21:09
Yeah, 

Richard Wilmore 21:10
people, you know, 

Rich Bennett 21:11
I mean, 

Richard Wilmore 21:11
over the course of just me working there. 

Rich Bennett 21:14
I mean, that's, that's the big thing. And you said these were people were on the podcast, right? it was 

Richard Wilmore 21:21
No, 

Rich Bennett 21:21
just you working there. 

Richard Wilmore 21:22
Okay. Yeah, that was just me. Yeah, yeah, we have, well, I started a podcast there. I wanted to. 

Rich Bennett 21:27
Okay. 

Richard Wilmore 21:28
And the executive director at the time said I couldn't do that. So I settled for a podcast. 

Rich Bennett 21:33
Okay, but were you were telling their stories there, right? 

Richard Wilmore 21:36
Yeah, yeah, yeah, teaching people how to what arts and about arts and health and how to do it in your own life before you get sick. And we would talk to patients and 

Rich Bennett 21:45
so all those listeners too that you helped, which 

Richard Wilmore 21:48
yeah, 

Rich Bennett 21:49
there's guarantee you rich just knowing you there's probably a mess loo that you helped then didn't even know it because they heard 

Richard Wilmore 21:58
it. Yeah, 

Rich Bennett 22:01
man, let's get off the steep stuff. No, don't pick another deep one. All right, 

Richard Wilmore 22:05
okay, 

Rich Bennett 22:06
sorry. Give me another number 

Richard Wilmore 22:08
three. 

Rich Bennett 22:09
Oh god, now I got to get backwards. 

Richard Wilmore 22:11
Sorry. 

Rich Bennett 22:12
That's all 

Richard Wilmore 22:12
New 

Rich Bennett 22:12
right. 

Richard Wilmore 22:13
work. 

Rich Bennett 22:13
know you like making me work. All 

Richard Wilmore 22:15
I 

Rich Bennett 22:15
right. Number three, 

I like this. Uh, and this is a good question for podcasters because I think every podcaster should be, they should have a year that they liked. What was the very first audio show or podcast that completely hooked you and made you fall in love with the medium? 

Richard Wilmore 22:48
I mean, for me, it wasn't podcasts. It was, it was, throws you it almost 

Rich Bennett 22:51
right. 

Richard Wilmore 22:53
Um, so I had looked it when I first started, I got lumped to podcasts and I think I wasn't even really a podcast. I just, there was no other space for me when I started like, I looked at it as a TV show. 

Rich Bennett 23:04
Well, you're strictly YouTube. 

Richard Wilmore 23:07
Yeah. Yeah. I wasn't even on podcast platforms. And so when people started telling me that I was a podcaster, I was like, Oh, I guess, sure. I, yeah, that's the box I could fit in. I suppose. 

Rich Bennett 23:21
Vodka, I spec'd it is what it was called. 

Richard Wilmore 23:23
Yeah. Yeah. 

Rich Bennett 23:24
When it was strictly video, you're interviewing. 

Richard Wilmore 23:27
Yeah. 

Rich Bennett 23:27
Unless it was on. 

Richard Wilmore 23:27
So right. Yeah. Yeah. So there were, I was not, I, even when I started the podcast for the Arts and Health Nonprofit, I'd never listened to one before. 

Rich Bennett 23:38
Really? 

Richard Wilmore 23:39
No. 

Rich Bennett 23:41
To this day, you don't? 

Richard Wilmore 23:42
I listened to a couple, but I watched them. I like, 

Rich Bennett 23:45
Right. 

Richard Wilmore 23:45
I'm a visual person. So if they have a YouTube channel, I will 

Rich Bennett 23:51
watch it. Wow. Okay. Well, you could still, I guess even on YouTube as you're driving, you can listen to it as you're driving. Just don't watch it while you're driving. 

Richard Wilmore 24:00
No, no, no, no, I know. But yeah, I watch. 

Rich Bennett 24:06
Yeah. 

Richard Wilmore 24:07
Yeah. Cause. 

Rich Bennett 24:07
So, 

Richard Wilmore 24:08
how, I've, 

Rich Bennett 24:09
what are some of the ones you're watching 

Richard Wilmore 24:12
now? Um, I love good hang with Amy Polar. 

Rich Bennett 24:14
Okay. 

Richard Wilmore 24:16
Um, but to me, like, is that a podcast? I don't know. Like, none of these podcasts that are filmed in that way are podcasts to me. They're, they're talk shows, but with a big mic in your face 

Rich Bennett 24:28
Well, yeah, and if you can't listen to them on like pocketcass and all that, then I want to consider it a podcast. 

Richard Wilmore 24:33
and you. 

Rich Bennett 24:33
It would be a talk show. 

Richard Wilmore 24:35
Yeah. I mean, you, they're, they are on all those platforms, but I think that it's it's so amassed. 

Rich Bennett 24:42
Right. 

Richard Wilmore 24:44
That, I mean, what is it? 

Rich Bennett 24:45
You know, yeah. 

Richard Wilmore 24:46
Oprah's got a podcast, but she films it in front of a studio audience. 

Rich Bennett 24:50
Yeah, that is fun, though. 

Richard Wilmore 24:52
I mean, you know, I would do that in a second. 

Rich Bennett 24:54
Oh, I've done a couple of them. It's fun, but it's also scary. Me and it, it, when it comes the editing part, you talking about a nightmare. 

Richard Wilmore 25:04
Yeah, 

Rich Bennett 25:04
but all right. Another number, if you go backwards, that's fine, because you pick three. 

Richard Wilmore 25:10
Okay. Well, I'm gonna go number one. 

Rich Bennett 25:12
Number. 

Richard Wilmore 25:13
There. 

Rich Bennett 25:14
Oh, my God. Okay. Really? 

Richard Wilmore 25:18
Oh, 

Rich Bennett 25:18
I'm 

afraid to ask this one. 

Richard Wilmore 25:23
I'm scared. 

Rich Bennett 25:25
What is the absolute worst podcast interview question you've ever been asked as a guest? 

I got an easy answer for that one. 

Richard Wilmore 25:39
What's your answer? 

Rich Bennett 25:41
well, is that really, it can be a statement but it can also be a question. Can you tell us a little bit about yourself? 

Richard Wilmore 25:50
Hmm, 

Rich Bennett 25:51
because you stick about it a lot of times, that's in the introduction. 

Richard Wilmore 25:55
Hmm. 

Rich Bennett 25:55
And most of the time when you go on a podcast, it's, I mean, there are somewhere to pitch. You're throwing a pitch. But to me, that is probably one of the worst ones. 

Richard Wilmore 26:13
Yes. Yeah, that's a good answer, I feel like, because, um, I mean what does that even mean? Like how is this a 10 minute long conversy, you know, like, 

Rich Bennett 26:23
Just 

Richard Wilmore 26:23
yeah, I 

Rich Bennett 26:23
a 

Richard Wilmore 26:23
think 

Rich Bennett 26:23
little 

Richard Wilmore 26:23
that's 

Rich Bennett 26:23
bit 

Richard Wilmore 26:23
the- 

Rich Bennett 26:24
about yourself. Well, I was boy, I remember being in the womb. Yeah, I mean, eh, see, when it comes to those questions, one of the ones I do like to ask sometimes, especially if I'm talking to an entrepreneur or a business earner is back in high school, what was your career path? What was it you wanted to do? But I'm not going beyond that, you know, unless it's something with childhood trauma or 

Richard Wilmore 26:53
something. Yeah. 

Rich Bennett 26:54
That's, that's another tough question though. Because not everybody asked that. 

As far as Toss, can you tell us a little bit about yourself? 

Richard Wilmore 27:05
Right, sometimes I'll ask people, especially if they have very interesting careers, I'll ask them, um, or if they have really boring careers, I'll ask them, like, what do they want to be when they work it? 

Rich Bennett 27:17
Yeah, 

Richard Wilmore 27:17
how 

Rich Bennett 27:17
we, 

Richard Wilmore 27:18
does that a lot? Yeah, like, how does that align with what you're doing now? 

Rich Bennett 27:21
Which is similar to what I said about us, you know, what was your career career path in high school? 

Richard Wilmore 27:27
Yeah, 

Rich Bennett 27:27
yeah, I don't think we had that in high school. 

Richard Wilmore 27:30
You didn't have a little, we had the test and it would be like, clown. And then you'd like to take this whole big test and then everybody came back as they could be a clown. 

Rich Bennett 27:38
We may 

Richard Wilmore 27:39
I was 

Rich Bennett 27:39
have, 

Richard Wilmore 27:39
like number one, 

Rich Bennett 27:40
we may have, I don't remember a lot of that high school. Look, Rich, okay, I was a long time ago. Keep in mind, I'm so old that back in my days of high school, we were chiseling on a stone, that was our paper. 

Richard Wilmore 27:53
Of course, yes, 

Rich Bennett 27:54
no, I'm not that 

Richard Wilmore 27:55
You 

Rich Bennett 27:55
old. 

Richard Wilmore 27:55
couldn't even, so podcasting was certainly not in your future. 

Rich Bennett 27:59
It was rock casting. 

Richard Wilmore 28:00
Yeah. 

Rich Bennett 28:02
God. Oh, babe, why did, why didn't, never mind, did I go, just cracking all myself already? All right, pick another number. 

Richard Wilmore 28:12
Um, 22. 

Rich Bennett 28:15
That's how, that's how Rich looks for those of you listening, 

Richard Wilmore 28:19
but

Rich Bennett 28:20
22. 

Oh, man, is okay. 

This, okay, man, what does it take to turn a casual chat into a truly transformative experience for both the guest and the listener? 

You're listening to the conversations with Rich Bennett. We'll be right back. W H F C 91.1 F M. That's right, Harvard Community College Radio Station. It's more than just great music. It's about community, and they're showcasing the talents of the students and community volunteers. W H F C is designed for and run by the Harvard County community. It's focused on teaching and learning. W H F C student learning lab is for anyone interested in radio and podcasting you heard me right. So if you want a career in radio or podcasting, Harvard Community College is the place for you, and you can learn at the radio station, go to W H F C 9 1 1 dot org or tune in on the dial at 91.1 F M and give them a listen, I guarantee you, you'll love the music. And if you want to get into broadcasting or podcasting, then check them out. 

Richard Wilmore 29:48
I feel like as a listener, you really like same thing when you're watching TV, like when it feels like there's chemistry 

Rich Bennett 29:55
like, 

Richard Wilmore 29:55
there, 

Rich Bennett 29:55
yeah. 

Richard Wilmore 29:56
It feels, I think that is a major one. I think it's, what did I learn or what did I teach? If it's, it doesn't have to be rocket science, but like, what's the takeaway from it? Did I do that? And did I receive that? I had another one, but now I forgot it. 

Rich Bennett 30:14
Yeah, I think the main thing is, is if people are learning from it as a host, if you're learning from it, then you know, that usually the listeners are. And even with this, just now, you and I talking, I'm learning stuff because I never seen these questions. And your answers, some of your answers are different than what I would say. But as long as you and I have been doing this, doing the podcasting, 

there's a lot that we can offer to other podcasters, which other podcasters do listen. But there's also a lot we can offer to listeners that want to. be a guest on the podcast because I'm sure you've seen this too. You probably get a ton of emails for somebody who wants to come on the show, but they don't know why they want to come on the show. 

Richard Wilmore 31:12
Right. 

Rich Bennett 31:14
And it's, I mean, I've had people email me and say, "What do you want to come on the show far?" And they'll say, "Let's talk politics." Well, first of all, obviously you don't listen to show because we don't talk politics. You know, or, "Let's talk about I don't know." So and so. 

Richard Wilmore 31:32
Yeah. 

Rich Bennett 31:32
No, you have to know what you want to talk about. And then even the host can turn it around. I mean, how many times have you turned it around on me? Come to think of it the first time I came on. 

Yeah, that's all right, Richard. I'll still let you. I forgive you for that. I pick another one. 

Richard Wilmore 31:56
Okay. 

75. 

Rich Bennett 32:00
75. Really making me jump forward now. Richard saying, "Yeah, well, that's your age. Rich, isn't it?" And he's saying, "No." Okay. It's the saying of Beard. Oh, oh, okay. Ooh, I like this question. I've had this happen before and I'm sure you have too. What is a time you had to cut a piece of tape? Oh my god. 

What is the time? Okay. These questions definitely were focused towards me because I remember working at a radio, we used, 

Richard Wilmore 32:35
I'll 

Rich Bennett 32:35
tape and how to cut it. When is the time? I'm going to keep that in there. When is the time you had to cut a piece of tape or edit out a segment that broke your heart because it didn't serve the listener or I'm going to add to that or not publish an episode because of the same thing. 

Richard Wilmore 32:59
The first time I ever had to not air an episode was when I lived in Maryland. 

I went and it was like an on-location type situation and I went and I mean, I was like, it was like I got invited to this open mic night or something. 

Rich Bennett 33:18
And 

Richard Wilmore 33:19
so I went to and there were people performing all different things and I went and there were singers that really wanted to be on the show. Like and so I filmed it and it was just so bad. Like the singers were not that you know like nobody was really, I didn't want to I didn't want to embarrass them by putting that out there and so I just never did anything with it. That was the first I mean I've had others since then but that was the first time that ever happened. 

Rich Bennett 33:50
What are some of the others? If you could just 

Richard Wilmore 33:52
yeah. Yeah sure. So I did one that just felt odd 

Rich Bennett 33:59
yeah 

Richard Wilmore 33:59
and it was it was with our friends over at pod match. and I reached out to Alex and said this I this didn't go well but I mean you give me money for these interviews so like what's what's the rule? And he said if it's not good don't put it out. Like he's 

Rich Bennett 34:17
Yeah 

Richard Wilmore 34:18
like I don't care do not because it's it's your face and their face so do not and so I didn't do that but it was just like I don't know I maybe someone who wasn't very well prepared for the interview or had never really done it or you know people who try to cram like I ask one question and they try to cram everything into an answer and that always makes me sad because I'm like no stay let's there's like a little bit of a roadmap here and we can't take every exit that we see. 

Rich Bennett 34:54
right right. 

Richard Wilmore 34:54
So those are usually the ones you know or nonprofit founders who just love to tell their story and sometimes that story goes on for too long and they're having a great time but I would need to be a little shorter. 

Rich Bennett 35:08
Yeah yeah it's hard. I've only had a few to where I couldn't publish them as far as the editing part there are a couple things I had to take out especially when I first started I'm sure you did the same thing you know you would take out the swear words. And I stopped doing after a while because it did add to the story come to you know when I listen to it back then especially people on recovery. But there are other things that you just either have to edit it out or there's just episodes you cannot publish because it's just awful. And I'm sure you ran into this I know I remember one of the worst ones I had was and I was asking open-ended questions and the guy was giving me short 

Richard Wilmore 36:02
answers. 

Rich Bennett 36:03
You know like now just he wouldn't go into detail 

Richard Wilmore 36:05
and 

Rich Bennett 36:06
I felt so bad it's like dude come on. 

Richard Wilmore 36:11
Yeah When- When that happens to you, if it starts off like right away, you just know, you know, you're like, 'Do you- Do you just do the full interview?' Do you try to shorten it? Do you, like, what's your plan usually? 

Hmm. 

Rich Bennett 36:40
And, I mean, even my co-husks were asking, and it would have been a great interview, but he was just very low-turned like he was shy.The  funny thing is, after we were finished, and the two women left. Then he opened up, as I'm putting the gear in my car, he opened up, he would not shut up! 

Richard Wilmore 37:01
But- 

Rich Bennett 37:02
Where the hell were you while we were recording? That granted it was his first podcast, but still, it's like, I cannot publish this, nobody's 

Richard Wilmore 37:13
get it. 

Rich Bennett 37:13
gonna 

Richard Wilmore 37:13
Yeah. 

Rich Bennett 37:14
I think out of it. And there was another one I did where, um, unfortunately, I got- I wish I could have published it, but when I went back and listened to it, there was nothing people would have gotten out of it. I didn't- and I don't want to mention what that one was about because it involves some people that, you know, 

Richard Wilmore 37:37
are- that are- that are in the room right 

Rich Bennett 37:38
No, that are close to me. 

Richard Wilmore 37:40
now. 

Rich Bennett 37:40
Nobody- we're not gonna be 

Richard Wilmore 37:42
I 

Rich Bennett 37:42
anybody. 

Richard Wilmore 37:42
was like, I was now trying to think I was like, is every time I went on the show, did that come out? Do I 

Rich Bennett 37:47
I'll 

Richard Wilmore 37:48
remember? 

Rich Bennett 37:48
tell you after we finish, 

Richard Wilmore 37:50
Okay. 

Rich Bennett 37:50
there's more of the man behind the green curtain. Oh, I picked another number. 

Richard Wilmore 37:57
Um, 94 from my grandma. 

Rich Bennett 37:59
Ninety- 

Wow, okay. And I- I think I know the answer for this one, but- how do we- how do you prevent your show from becoming repetitive when you've been talking about similar themes for years? It's easy. 

Richard Wilmore 38:23
I mean, I do two things. One, I feel like everyone's story's going to be 

Rich Bennett 38:26
Yeah. 

Richard Wilmore 38:26
different, so that's pretty easy. Um, I think that's also the fun in like what we do that our shows are always so, um, random. There's such a variety to our guests that when I first started with Pod Match, I was doing like five or six interviews a day, five days a week. 

Rich Bennett 38:44
Wow. 

Richard Wilmore 38:44
And, um, I did that for like two months and I was like, okay, well now I- that's when I started feeling like, I can't talk about this anymore, but that was my fault, 

Rich Bennett 38:54
Right. 

Richard Wilmore 38:54
you know? Because I- I was doing that to myself, or I take a break, like then that's also a sign for me like, oh, maybe my season is over. 

Rich Bennett 39:02
Yeah. 

Richard Wilmore 39:02
And maybe I take a break for a couple of weeks. 

Rich Bennett 39:04
And it is okay to take a break. Those of you getting into podcasting, it's okay to take a break. Sometimes you have to, you know, and people do get what's called Pod Feed. So it does happen. Uh, let's see, you said 94. I pick another one. 

Richard Wilmore 39:26
Um, a hundred. 

Rich Bennett 39:27
Damn. 

Richard Wilmore 39:28
Oh. 

Rich Bennett 39:29
Oh, no, I'm sorry. I- 

Richard Wilmore 39:30
I- I- Do you want to pick a number? 

Rich Bennett 39:31
I snuck a peek at one. Um, okay. We- Ooh. Oh. This is- 

this is great. This is great. 

Richard Wilmore 39:44
Okay. 

Rich Bennett 39:44
When you look back at the entire archive of your life's work as a host, what do you hope people say about the space you created for others? 

Richard Wilmore 39:58
Um, 

I mean, I got into it for that exact reason. Cause that's what Rosie did for me. It was like, created a space where I felt like, oh, I belong there. Um, and, um, 

That's- my goal always is to 

Rich Bennett 40:17
yeah. 

Richard Wilmore 40:17
create that space where people feel like they get- they're safe to break about themselves and that it's okay to do that. Like, that's my favorite thing is getting to hear and see people get excited about what they do. Cause we don't get to do that all the time. 

Rich Bennett 40:31
No, we don't. And- and the other thing is too is you could have, somebody on- well, prime example. Like with you, uh, the other times you've been on and then this time is completely different from any other time you've been on. 

Richard Wilmore 40:49
um, 

Rich Bennett 40:49
So it- it's not repetitive and there's our other even podcasters I've had on where everything is different. I don't know, you know, uh, aerial nussent black uh, podcast and Hall of Fame. She, um, 

uh, uh, what was it? Uh, squat. I think she was involved in starting squat cast, I believe, but she's got a ton of podcast out there. But everything that she talked about was different, say, from when Alex, Alex and Philippa had on, from what he talked about. 

Richard Wilmore 41:24
Mm-hmm. 

Rich Bennett 41:25
So everybody has different things and you're still learning. Alright, uh, man, I'll might pick a question later. Pick another one. 

Richard Wilmore 41:37
Um, 

15. 

Rich Bennett 41:40
50. 

Oooh. 

..like, be a little legacy thing here. 

Richard Wilmore 41:52
Uh-oh. 

Rich Bennett 41:53
When- Ha, ha, ha-ha. What do you mean, uh-oh? Heh. I- when all the episodes are recorded, and the archives are closed, what do you want your digital footprint to say about who you were? 

Richard Wilmore 42:12
Uhm, I think, because I've been doing it for a long time. Already, like, to see the growth in me, as a host, as a person, as a human, I think is probably- I don't know if I would want people to watch the early shows, because I don't even have microphones. But, uhm, ha- ha, I never thought about that. All I wanted was to talk to people, 

Rich Bennett 42:37
Right. 

Richard Wilmore 42:37
and so I started recording- I at least had something to record with. Uhm, 

yeah, I think growth in-in-in me and the guests and-in the shows that I-that I'm help with and make, yeah. 

Rich Bennett 42:53
Definitely the way you have changed things, because I've had guest on that we're on your show. 

Richard Wilmore 43:00
Oh. 

Rich Bennett 43:00
And I've even said this about your show, uh, because you've changed it up throughout the years. 

Richard Wilmore 43:05
Mhm. 

Rich Bennett 43:05
From, from, you know, being the Richard Wilmore show, to now make your day richer, and I say change it up, I'm- I'm mainly talking about, the background, the studio, 

Richard Wilmore 43:17
uhm, 

Rich Bennett 43:17
and then the production, when you-when you produce it and put it out there, as if you're talking to somebody on the TV, and it- to me, that, that was wild as hell. That was good. But the other guests, they have come on and they always talk highly of you. So you're already- you're definitely leaving that, I don't want to say digital footprint, you're leaving the legacy. 

Richard Wilmore 43:43
Hmm. 

Rich Bennett 43:43
Yeah. When people talk highly of you that you've- you know that, been on your show, that is good- and I always do too. I mean, you're like my long lost brother. And 

Richard Wilmore 43:56
we're starting- we look more and more alike every day, we need... 

Rich Bennett 43:58
Yeah! You 

Richard Wilmore 43:58
glasses. 

Rich Bennett 43:58
Yeah, you're just going to have to, you know, be my backup Santa Claus. I'm not even going to ask one. I'm going to go with, uh- 

oh, okay, I was going to go with my age, because see, I did something that not a lot of people get to do. I turned- my age this year, I turned the same age- I turned the age of the year I was born. 

Richard Wilmore 44:24
What's that called? 

Rich Bennett 44:25
I don't know. Is it called a thing? 

Richard Wilmore 44:27
Yeah. There's a- yeah, there's a name for it. 

Rich Bennett 44:30
Okay. So yeah, I turned 63, because I was born in 63. A lot of people that were born in 99, they're not good, or even in a- 

Richard Wilmore 44:37
Never. 

Rich Bennett 44:38
period. They're 

Richard Wilmore 44:38
It's 

Rich Bennett 44:39
not going to get that. 

Richard Wilmore 44:40
That's so true. Oh, that's so sad. 

Rich Bennett 44:41
So I'm gonna say- 

Richard Wilmore 44:43
(laughs) 

Rich Bennett 44:44
Wait, but which part's sad about the people that I turn to, the fact that I turned 63? 

Richard Wilmore 44:48
No, the people won't be able- I forgot the term, but that people won't be able to celebrate that. 

Rich Bennett 44:53
Alright, I like this one. What is a piece of editing, magic, or production choice that you feel completely transforms the soul of 

an episode? 

Richard Wilmore 45:05
Of an episode? I mean, I love a good backdrop. 

Rich Bennett 45:08
Yeah. 

Richard Wilmore 45:09
You know? The whole feel of it, I think. 

Yeah. I like- I just filmed an episode the other day and I had pulled a clip from- to- to- to for the guest and the look on their fake Sometimes I think people always say to me like, "God, I feel like I was on the tonight show." Like, that's the usual, 

Rich Bennett 45:31
like- of 

Richard Wilmore 45:31
like, I 

Rich Bennett 45:31
it. 

Richard Wilmore 45:31
feel- and like, to- when you get to- throw to the clip with a guest, you know, that's not used to that, like, all those random stupid things that I do because I want to be a TV show host, like watching the guest get excited about something that they didn't see coming. 

Rich Bennett 45:46
Yeah. 

I think, for me, definitely the software has been a big change. And even the hosting company I use because, you know this, there are sometimes you get guests on especially when you're recording virtually and their sound level's not as good. Or they have air conditioning or- they have all the background noise. And out days with the stuff that we use, you can take all that out. 

Richard Wilmore 46:18
Yeah. 

Rich Bennett 46:19
And actually, it'll take it out automatically for you. All right, I'm gonna let you pick another one, Rich. 

Richard Wilmore 46:26
Um, 

um, 36. 

Rich Bennett 46:36
Ooh. All right, I think I know the answer to this one, too. What is the heaviest idea or concept you've ever tried to unpack through your show? Oh, maybe I don't know the answer to that. 

Richard Wilmore 46:53
Gosh. 

I mean, I don't think I've ever done an Oprah type episode where I'm trying to unpack anything 

Rich Bennett 46:59
Yeah. 

Richard Wilmore 47:00
like that, but I've, I, I, we've had, um, people talking about mental illness a lot. I- that's a, um, I have a lot of nonprofits on my show so that can sometimes be some really Tough subjects. 

Yeah, I mean, 

yeah, I would say probably mental mental health stuff. 

Rich Bennett 47:33
Yeah. 

Yeah. Yeah. Yeah, that is hard. All right. So as far as your company goes because you're helping people get on podcast and everything, when did you actually start doing that? 

Richard Wilmore 47:48
Um, when I started helping other people with their shows. 

Rich Bennett 47:53
Okay. 

Richard Wilmore 47:53
So I would, then I started doing the shows and helping them find, and it kind of, it was another, one of those things that kind of just happened because other people would be like, "Oh, well, can you do that for me then?" And then I was like, "Oh, right. This is like a service." 

Rich Bennett 48:09
well, yeah. But it's another 

Richard Wilmore 48:11
So 

Rich Bennett 48:11
way to help you grow your podcast as well. 

Richard Wilmore 48:17
Yeah. Yeah. I mean, I saw how excited people would get when they would come on my show or show I was producing. And they acted as if they couldn't do it again. And like they didn't, that seemed so unobtainable to people. So it's been really fun. 

Rich Bennett 48:32
So have you, when it, because you're getting a lot of people on shows, have, and you talked to them before you beforehand, are there any that you had to turn away 

because you just, 

Richard Wilmore 48:50
um, 

Rich Bennett 48:51
they, 

Richard Wilmore 48:51
I've never, I've never had to say no to someone, usually that type of person is the person who's going to just kind of fall off. 

Rich Bennett 48:59
Right. 

Richard Wilmore 49:00
Anyway, and so I've never, we've never gotten to a place with someone like that that I've had to be like, I don't think this is going to work. It usually like works itself out. 

Rich Bennett 49:12
I still, 

I want to become, I want you to walk me through the process. I call you. I contact you, which how can people contact you, 

Richard Wilmore 49:23
uh, make your day richer calm, 

Rich Bennett 49:26
because I want to get on other podcast. 

Richard Wilmore 49:28
Uh-huh. 

Rich Bennett 49:29
So I contact you. Walk me through everything. 

Richard Wilmore 49:32
So the first thing is you feeling out of form. That's kind of my first, like, is this, does this person have a business, a story, whatever that, that I think I can help with? So that's the first thing is, is getting through that. And then we jump on a call, and I hear more about you and why you want to go on podcasts. Um, and the form basically gives me everything I need to know to start pitching, um, to podcasts. And then every Monday, you get an email from me of these are the ones that want you. Are you available this day? Circle, yes, or no? 

Rich Bennett 50:03
That's it. 

Richard Wilmore 50:04
That's it. 

Rich Bennett 50:06
That's pretty, 

Richard Wilmore 50:07
I try to keep it easy, because otherwise I feel people that's going to feel like work. And then people are going to stick with it. And I think being a guest on podcast and or hosting a podcast, like that's a long term commit. 

Rich Bennett 50:19
Yeah, that's true. 

Richard Wilmore 50:20
It should be. And so I try to make it easy where it doesn't feel like I'm sending them an email every day and like I'm spamming them. Um, and yeah, I do all of it. 

Rich Bennett 50:30
When's the book coming out? 

Richard Wilmore 50:35
I've been I, what do I write about? I don't 

Rich Bennett 50:38
know. Well, I mean, I don't know. I said the same thing, but I had somebody on and now I have to write the book because she told me I have to 

Richard Wilmore 50:47
see. Well, I'll get her on my show. So then, 

Rich Bennett 50:49
through what? 

Richard Wilmore 50:50
Well, I'll get her on my show and then we can go on like a joint release tour. We could just go together on. 

Rich Bennett 50:55
You may have had her on your show. Nicolette Holliday. 

Richard Wilmore 51:00
Oh, my gosh. Um, 

Rich Bennett 51:03
she helps all she helps authors. 

Richard Wilmore 51:06
I don't think so. 

Rich Bennett 51:07
Okay, all right. Well, watch out because if you get her on, then she's going to have you write in a book. 

Richard Wilmore 51:12
Uh 

Rich Bennett 51:13
oh. 

Richard Wilmore 51:14
He's a 

Rich Bennett 51:14
urge. 

Richard Wilmore 51:14
high 

Rich Bennett 51:15
No, she's she is good though. She's good. And, um, I don't think she's a ghost writer. I think she just like helps people with their book helps them write it and get it published and all that. Yes. 

Richard Wilmore 51:28
So helpful. 

Rich Bennett 51:29
Oh, it is. 

Richard Wilmore 51:30
It is. Yeah. 

Rich Bennett 51:31
Now, are you still doing the actual podcast, or are you just gesting a lot right now? 

Richard Wilmore 51:37
Um, I host a couple podcasts. Um, 

Rich Bennett 51:40
what would you meet a couple? 

Richard Wilmore 51:42
Yeah. Yeah. I host a local one for the area that I manage. Do that every Wednesday. 

Rich Bennett 51:47
Oh, 

Richard Wilmore 51:47
Like 

Rich Bennett 51:47
wow. 

Richard Wilmore 51:47
a live show. Um, Um, I host the Wolf Media Fest podcast. I've been doing that for like three or four years. Um, it's a media festival and so anybody making media from podcast, you could submit your podcast to a movie, music fit, like any type of media. 

Rich Bennett 52:05
really? 

Richard Wilmore 52:06
Um, yeah. Yep. And so I get to talk to all the winners of it's a monthly festival and I get to talk to all the winners of that festival. 

Rich Bennett 52:14
And that's a virtual festival or in person. 

Richard Wilmore 52:17
Um, so it's a virtual festival and then I yearly, they'll have an in person event. 

Rich Bennett 52:23
Where's that at? 

Richard Wilmore 52:25
Um, she is based in Florida. 

Rich Bennett 52:28
Okay. 

Richard Wilmore 52:29
Yeah. 

Rich Bennett 52:29
How did you find out about that? 

Richard Wilmore 52:31
Did you? Oh, okay. So first of all, you know the guys of Big Infinite. 

Rich Bennett 52:34
Yeah. 

Really? 

Richard Wilmore 52:46
Uh, award, big infinite one award, 

Rich Bennett 52:48
yeah. Did they? 

Richard Wilmore 52:48
And, 

Rich Bennett 52:49
Oh, that's all. 

Richard Wilmore 52:49
yeah, for their documentary. And, um, so they came down Jordan and Megan came down. I got to hang out with them in Florida. 

Rich Bennett 52:57
Oh, man. That is awesome. 

Richard Wilmore 52:59
Yeah. 

Rich Bennett 53:13
For now. 

Richard Wilmore 53:13
Uh, I stopped that. When did I stop that? 

Earlier this year. 

Rich Bennett 53:20
Okay. 

Richard Wilmore 53:21
Um, I don't know. I, I was going to start a podcast about local nonprofits. 

Rich Bennett 53:27
Yeah. 

Richard Wilmore 53:27
Um, and I had filmed my first interview that was going to start coming out. And then I just, um, didn't feel like it. 

Rich Bennett 53:36
Yeah. 

Richard Wilmore 53:36
And I thought, I, if I make myself do this, I'm not going to. And so I'm going to roll it into the week the other show that I do. But, um, yeah, I don't know. I love, I'm really loving finding shows for people and connecting people to other, other shows. I, I have a blast doing that. Because I get to meet the podcasters. I get to meet the guests and, um, that's been really fun. 

Rich Bennett 54:03
Really? 

Richard Wilmore 54:04
Hmm. 

Rich Bennett 54:05
Alright, wait a minute. I don't recall you ever contacted me about a guest coming on. 

Richard Wilmore 54:12
Well, I have one for you. 

Rich Bennett 54:14
Okay. 

Richard Wilmore 54:15
I do have one for you. Yes. 

Rich Bennett 54:19
Alright. Do you get a lot of authors as for as clients? 

Richard Wilmore 54:24
Um, so the one, um, we'll talk after this about what he does, but he does have a book. 

Rich Bennett 54:30
Okay. I bring that up because I also, because I, as if I don't have enough to do, launched another podcast. 

Richard Wilmore 54:38
I saw that 

Rich Bennett 54:39
strictly for authors and it's short form. Thank God, it's short form. Yeah. Because otherwise, I'd be, um, going all my hair out, whatever, I have left. And you know, there's not a lot 

Richard Wilmore 54:53
left 

Rich Bennett 54:53
done. 

Richard Wilmore 54:53
that 

Rich Bennett 54:54
So. Alright, 

Richard Wilmore 54:54
we've 

Rich Bennett 54:55
so Rich, is there anything that you would like to add before I get to the last question, which has nothing to do with podcasting? 

Richard Wilmore 55:02
Um, no, I want to know what this question is. 

Rich Bennett 55:06
So do I. Alright, so now I need you to pick a number between one and five. 

Richard Wilmore 55:12
He's such a prepared podcast host, um, wait. One number, 

Rich Bennett 55:17
one through three, one and five, 

Richard Wilmore 55:19
three, 

Rich Bennett 55:20
three. See, I have these emblocks. These are different question. This is what I usually ask. I really sort you in. Now I need to pick a number between 41 and 60. 

Richard Wilmore 55:28
This feels like that one thing we used to do when we were kids. Um, one through, uh, 

Rich Bennett 55:34
no, 41 through 60. 

Richard Wilmore 55:36
Oh, 45, 

Rich Bennett 55:37
45. 

Wow. I don't think this question's ever been asked. What does it mean to live a good life? 

Richard Wilmore 55:55
Um, I'm really liking loving my life right now. Um, it hasn't usually been like that my entire life. And I've got through a lot of therapy about how to enjoy this. Um, but I have so much piece at home. And, um, support and quiet time. 

Rich Bennett 56:17
Yeah. 

Richard Wilmore 56:18
And true, true friends and that's been just the best, um, last five years I could have ever asked for that feels like it feels like a really good life right now being able to do what I love. 

Rich Bennett 56:30
Yeah. 

Richard Wilmore 56:31
Um, and just having fun. I get to laugh every day. 

Rich Bennett 56:34
That's important. That makes you, I think that always adds more years onto your life. If you can laugh every day and just 

Richard Wilmore 56:43
happy. 

Rich Bennett 56:43
be 

Richard Wilmore 56:43
Yeah. Yep. 

Rich Bennett 56:44
So Rich, it's always great seeing you. Don't wait another six years. 

Richard Wilmore 56:50
okay. 

Rich Bennett 56:51
You know, I don't know how, how it is that you're still looking 

Richard Wilmore 56:58
younger. It's a filter. 

Rich Bennett 56:59
And those, you know, those things on your beard there that you, 

Richard Wilmore 57:03
uh, 

Rich Bennett 57:03
it's not great. I think there's like wisdom spots. 

Richard Wilmore 57:07
Oh. 

Rich Bennett 57:08
Is 

Richard Wilmore 57:09
that what that is like wisdom teeth, like they're just coming in. 

Rich Bennett 57:12
It just shows how wise you are. 

Richard Wilmore 57:14
Yeah. 

Rich Bennett 57:14
You know, not, not like age spots. 

Richard Wilmore 57:18
No, no, definitely not. I can't know, 

Rich Bennett 57:23
oh, man. Rich, thanks a lot. Always good. See you still love your brother and don't be a stranger. If you ever get back up to Maryland again, if I find out you were up here. Like the last time when you were up here and you did not contact me, 

Richard Wilmore 57:38
to have 

Rich Bennett 57:38
we're going 

Richard Wilmore 57:38
I was, I didn't go to where was I? I was in Delaware. 

Rich Bennett 57:43
Yeah, they go through Maryland. 

Richard Wilmore 57:46
When I flew. 

Rich Bennett 57:47
Oh, you flew. Nevermind. 

Richard Wilmore 57:48
Yeah, I flew. Yeah, 

Rich Bennett 57:49
Fly 

Richard Wilmore 57:49
yeah. 

Rich Bennett 57:50
over Maryland. You could have jumped out. 

Richard Wilmore 57:51
I waived. I waived. 

Rich Bennett 57:53
Okay. I never mind. I had a feeling because I felt like somebody was waving to me. This conversation with Richard Wilmore was a great reminder that podcasting is about much more than downloads, views, or chasing the next milestone. It's about creating a space where people feel comfortable sharing who they are, helping listeners discover something meaningful, and recognizing the impact of conversation can have long, long after the micro-french returned off. Richard offered an honest look at the responsibility that comes with telling someone else's story. We discussed knowing what to share, protecting the listener, recognizing when an episode should not be published, and setting healthy boundaries when carrying other people's pain. Through Make Your Day, Richard helps people identify the stories that matter, connect with the right podcast and become heard, seen, and remembered. Perhaps the biggest takeaway was Richard's definition of a good life. Peace at home, true friends, meaningful work, support, quiet time, and the opportunity to lay off every day. Success may look different for each of us, but genuine connection and a life that feels fulfilling will always matter more than the numbers. Until next time, I'm Rich Bennett. Thanks for listening and remember, every great conversation starts with someone willing to listen and someone willing to share. Now, it's your turn. Join the conversation by sharing this episode, leave in a comment, or reaching out to me directly. Take care, be kind to one another, and I'll talk with you again soon.