The SkyePod - What Improv Teaches Us About Faith

Summary

The SkyePod - What Improv Teaches Us About Faith

Host: Skye Jethani
Guest: Jeff Ash (Owner, Westside Improv Theater, Wheaton, IL)
Date: September 5, 2025

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Episode Overview

In this episode, Skye welcomes his friend and improv coach, Jeff Ash, to discuss the unexpected intersections between improv, life, faith, and community. Together, they recount personal stories, explore the core principles of improvisational theater, and reflect on how the lessons of the stage carry over into relationships, spiritual practice, and personal growth. The conversation moves beyond performance, focusing on connection, presence, relinquishing control, and rediscovering playfulness in faith and daily living.

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Key Discussion Points & Insights

1. Jeff's Improv Journey & Origins

[02:20] – [08:24]

• Early Beginnings:

  • Jeff always had a knack for humor and storytelling, often asked to give toasts and entertain friends.
  • His big break into improv came after a boss in L.A. suggested he try comedy.
  • Initial class at Second City Hollywood was unexpectedly dull:

    “We stood in a circle, there were like eight of us, and we bounced a tennis ball back and forth … for three hours. It was really boring.” – Jeff Ash [04:19]

  • Almost quit after day one but returned (reluctantly) at his wife’s insistence, leading to a pivotal period of personal growth.

• Learning Through Practice:

  • Jeff describes how the initial “boring” exercises were, in hindsight, foundational—fostering connection and presence.

• Instructor Philosophy:

  • Jeff’s own experiences shaped his approach to teaching improv; he intentionally sought to make classes engaging and fun from the start.

2. Building Community at Westside Improv

[09:42] – [13:28]

• Westside’s Origins:

  • Jeff didn’t move to Wheaton with an improv theater in mind; he noticed local talent via Wheaton College and small local shows.
  • Expected the theater to be a three-year hobby, but it quickly became a vibrant community hub.

• Contrast with LA/Chicago:

  • In LA, improv is a career stepping stone; in Wheaton, people participate for enjoyment and connection.

  • Skye notes the unique diversity at Westside, likening it to a church in its cross-sectional representation of the community.

    “I can only think of one other place where I’ve seen that level of diversity, which is a church, it’s a congregation… Westside is an interesting cross section of this community.” – Skye Jethani [13:00]

3. Improv Fundamentals: Connection & Listening

[14:03] – [17:55]

• Long Form vs. Short Form:

  • Jeff explains Westside’s focus on “long form” improv—extended, open-ended exploration akin to a play rather than punchy games.
  • He values long form for its deeper dive into “exploration of humanity” and authenticity.

• Listening & Presence:

  • Improv’s key skill isn’t quick wit, but deep, judgment-free listening and synchronization with scene partners.
  • Practicing being “unprepared” is a form of spiritual and relational growth:

    “If we want to do anything well, we have to practice at it... So it’s weird, if we want to be unprepared well—we need to practice being unprepared, and that’s improv.” – Jeff Ash [16:18]

  • The act of relinquishing control and being okay with oneself translates into family and life as well.

• Personal Impact:

  • Skye reflects on how improv made him more present and responsive in his marriage:

    “I actually told [my wife], I think this is going to make me a better husband. She was like, ‘What?’” – Skye Jethani [17:55]

4. Faith, Fear, Control, and Trust

[18:00] – [22:59]

• Religion and Control:

  • Skye draws a powerful parallel between improv practice and religious attempts at control:

    “All religion begins with fear, and we sense the world’s a dangerous and threatening place. In our fear, we want control… Whatever your system of control is, it’s all rooted in fear.” – Skye Jethani [18:56]

  • Many come to religion (or improv) looking for a “script”—predictability and security. But real growth involves surrender and trust.

• Trust as a Spiritual Principle:

  • Improv’s demand to trust the process and your partner mirrors the leap of faith believers are called to make:

    “So what does it look like to go, ‘I’m just going to trust my partner here, and in this case, in a spiritual sense, my partner’s God.’ But it’s also the people I’m doing life with.” – Skye Jethani [20:17]

• Parental Wisdom & Presence:

  • Jeff shares how releasing control as a parent dramatically improved his relationship with his daughters:

    “When I released trying to manage everything and just showed up for them as a dad and as a human, everything changed.” – Jeff Ash [22:59]

5. Rediscovering Play & Childlike Wonder

[22:59] – [24:05]

• Childlike Discovery:
  • Skye and Jeff celebrate the idea of “playing” as adults, observing how children approach life with curiosity and flexibility—qualities improv aims to revive.
  • “Yes, and…” is identified as improv’s most famous rule, and a philosophical anchor for embracing the unexpected.
  • Skye hints at more lessons and stories to come in the subscriber-exclusive portion.

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Notable Quotes & Memorable Moments

• “$380. You’re going to go back.” – Jeff Ash, quoting his wife, on why he stuck with improv after a bad first class [05:14]
• “In Hollywood, everyone was there to grow, get better. But the thing here [at Westside]... people are really here to do this thing. Improv isn’t a stepping stone—it’s the thing they’ve fallen in love with.” – Jeff Ash [11:35]
• “Long form is the exploration of humanity… we’re going to do it in a way where we have complete creativity, and we can be really authentic in the moment.” – Jeff Ash [14:03]
• “How do you really connect with a person? We do a silly exercise… you can’t speak to somebody until you make eye contact with them. Just really being present.” – Skye Jethani [17:55]
• “We don’t have a script. When you wake up in the morning, you don’t pull a script out of your nightstand… you don’t know.” – Jeff Ash [19:46]
• “Having kids is waking up in the morning and thinking of all the things you want to do that day and not getting to do any of those.” – Jeff Ash [21:38]
• “When I released trying to manage everything and just showed up for them as a dad and as a human, everything changed.” – Jeff Ash [22:59]

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Timestamps for Important Segments

• Introduction & Jeff’s Background: [00:00] – [08:24]
• Community at Westside & Comparison to LA: [09:42] – [13:28]
• Improv Fundamentals: Long Form, Listening, Presence: [14:03] – [17:55]
• Faith, Fear, and Surrender: [18:00] – [22:59]
• Play, Parenting, and “Yes, And…”: [22:59] – [24:05]

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Tone & Style

The conversation is candid, warm, humorous, and reflective, matching the playful-yet-deep vibe of improv itself. Skye’s earnest curiosity and Jeff’s thoughtful insights make for an engaging listen that blends spiritual wisdom with practical, accessible life lessons.

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To access the remainder of this conversation and more, listeners are encouraged to subscribe at holypost.com/skyepod.

Transcript

[A]

And I actually told her, I said, I think this is going to make me a better husband. She was like, what? Hey, everyone. Welcome back to the Sky Pod. I am here with a friend of mine and a guest named Jeff Ash. Hi, Jeff.

[B]

Hello.

[A]

So Jeff is the owner of the Westside Improv Theater here in downtown Wheaton. And for those of you who are part of our. Was it December? Our live show in December, we hosted it at Westside.

[B]

Yeah.

[A]

Jeff was kind enough to let us use the space. And you, you did a brief introduction and warm up the crowd kind of thing.

[B]

I emceed it. You MC'ed it in air quotes.

[A]

Right. Although your part did not actually make it into the broadcast, into the podcast. No. So sorry about that.

[B]

That's okay. That's why I'm here now.

[A]

Right. This is my payback. So Jeff and I have known each other for a couple of years because Josh, Lindsay and I. And you may know Josh from the Movie Proposal podcast. Josh, Lindsay and I signed up to do improv classes. Was that two years ago?

[B]

Two years ago, yeah. Yeah.

[A]

Jeff taught Level 1 improv at Westside, and Josh and I continued in level two and level three and gotten more involved. And now I am part of. Of sort of the west side community. Is that I'm on a team that you coach.

[B]

That's right.

[A]

That performs with some regularity.

[B]

Yeah.

[A]

Okay.

[B]

Yeah. You are the Westside community. We're building the community around you.

[A]

Hardly. Although I will tell you, it's been. It's been a real joy and just a great release and outlet and a fantastic community that I've really enjoyed. Anyway, I wanted to have you on the Skypod because I'm intrigued by your story. I enjoy talking to you, and there are lessons I've learned through being involved in improv of that I think are applicable to life, to faith, to theology, to all kinds. So we're just going to see where this all goes. But, Jeff, I want to begin just by hearing more of your story so we don't have to hear the whole story.

[B]

Yeah.

[A]

But I'd really love to know, how did you begin in improv? What was the introduction for you?

[B]

Yeah, I really love. I've always been kind of the funny one in any setting. You know, I was the guy who was like, I wouldn't be part of a wedding party, but my friends would say, can you do the toast? Like, I was that guy. Okay. So I got a job in Los Angeles, and I was working there, and I was living nearest to Hollywood, and I had a Boss who one day say to me, you know, you're pretty funny. Have you thought about ever doing comedy? And I was like, 30 years old at the time.

[A]

Did you move to LA with the thought of maybe something in the entertainment industry would happen, or was it unrelated to you?

[B]

Unrelated. Okay, Completely unrelated. I had my dream my entire life was to be on Saturday Night Live. I just have always loved the show. I've loved sketch comedy and. But I wouldn't have the first clue how to make that happen. Right. So we were. I was talking with this boss, and he said, you know, you should do comedy. And I was like, well, I'd love to. I don't know how to. I wouldn't even know where to begin. And he said to me, he said, well, I think there's a second city in Hollywood, and I know they offer classes. And so I went back to my desk and I, you know, asked Jeeves at the time, you know, and turned out there was a class just a few days later that was starting a level one class. And I got out the credit card and I signed up, and that was the beginning of the journey. And I really didn't care for the class the first time. It was boring. We didn't do a whole lot. I think I told this story for your level one class, but we stood in a circle, there were like eight of us, and we bounced a tennis ball back and forth.

[A]

Literally?

[B]

Yeah, literally. Okay. And it started out with, like, five minutes of bouncing the tennis ball. Inevitably, you're finding out who has hand eye coordination and who doesn't. Right. And then you were. When you bounced the ball, you were to say your name. And then after a while, when you bounced the ball, you said the person's name who you're bouncing the ball to. And then you made a sound, and then you made an emotional sound. And we literally did that on and off for three hours. It was. It was really boring.

[A]

And you're thinking, I. I paid money for this.

[B]

I'm thinking I made a huge mistake. Yes. Yeah. So I went home and my wife was waiting for me, very excited. I think her comment was, how is my comedian? Like, you know, when I walked in the door, how's my comedian? How was. How was it? And I said I didn't enjoy it, and I don't think I'll go back.

[A]

Wow.

[B]

You know, and so she said her. Her next thing she said to me, changed, kind of changed the course of my life. She said, it was $380. You're going to go back. So I was like, yes, ma'. Am. And I did. And the process that I went through over the next seven weeks, because it was an eight week class, was, aha. I get it now. I get the tennis ball thing. I get the connection. I get that piece of the experience. And I think after week two, I was hooked. Like then I wanted to go back every night, pretty much did that experience.

[A]

I don't remember what we did the first day of level one improv, when you were the teacher. But did that experience impact your approach? Did you want to make it more engaging right away or do you deliberately want to kind of weed people out?

[B]

No. Okay. I 100% wanted to make it more engaging and more fun. You know, I knew that people were here for a different experience. It, I mean, I had to understand too that I was in Hollywood where all of my classmates were actors trying to make it who's who. Their agents said, you need some improv. And so they're coming. And really what they need to learn is how to connect, right? How to, how to like, be in a moment with someone else. That's part of their acting process. For me, I was there to have fun.

[A]

So then after you initially started your classes, what happened? What was the rest of your initiation into improv and where did it go while you were in la?

[B]

Yeah, well, more classes because, you know, Second City has bills to pay. So, you know, it was always. There was always another eight week class to go. But I did have a little bit of success early on. I got the opportunity to perform with a few groups and do a couple different things. And you know, that I think that maybe accelerated a little bit of my journey through their program. But eventually what I did was I went into their conservatory program. You had to audition for the conservatory and get in, and then you did a series of, of classes and eventually it kind of came together in with a sketch show that you created with your. With your classmates. So that was kind of the process in the journey for me. And really what's funny is I go back to the first class I took, which was the tennis ball bouncing class. And that was really inspiration for me to start thinking about improv at a deeper level than just entertainment. Because what I loved was to entertain. Like I love, I love the concept of comedy. Getting on stage, making people laugh, doing funny, crazy things. I love that. But I really kept going back to that first class and thinking about the way we connect as people and the, I don't know, the profound kind of viewpoint that improv takes of that.

[A]

So that was what I was completely unprepared for.

[B]

Yeah.

[A]

When we signed up for that Level one class two years ago, I did it for a couple reasons. One, I'm a public speaker. I've done that for a long time. And I thought, I'm good when I know what I'm doing and it's scripted and prepared. And I actually, when I was preaching or when I speak someplace, I write my entire talk out. I write a full manuscript and I more or less memorize it and I go up without the script, but I know what I'm doing. And I thought improv might help me be more improvisational and handle things on the fly and field questions from people. So I thought it was a skill that would help me. But perhaps more importantly, when I was talking to Josh Lindsay about signing up for this class, I just need something to do. I just wanted to goof off and do something fun. Josh and I are friends, we laugh a lot, and I thought this would be a good time. I was not prepared. And I think I didn't really catch this until a couple weeks into Level one, that there were transferable lessons here way beyond just improving as a performer or thinking on your feet. So fast forward a little bit, you end up moving out here to Wheaton and you open west side. Why did you think Wheaton was the right spot to do this or was it not that thought through?

[B]

Yeah, yeah. Let's not give me too much credit. I don't, I don't think much. I make choices. Right. So when I, when I moved here, I got connected with some people at Second City, downtown Chicago. So I was doing some shows and, and doing some other things. And I, I met some people affiliated with Wheaton College and they have an improv program there for the students. And they actually asked me to come in and do some coaching. And so I was like, oh, wow. The, the Wheaton College improv program is. It's pretty alive, pretty vibrant. It's a good program. So. And I met a few improvisers out here that were just kind of stuck, you know, they didn't want to go into the city and they were doing shows here at like a library and things like that. So I thought, man, if I open something out here, I bet you there's enough of a community in Wheaton to make something work. But in reality, when I opened Westside, I really thought, I'll do this for three years. It's a three year lease. I'll have fun, I'll offer some classes, I'll do some shows, maybe no one shows up. It's a small risk. Let's just see what happens. So that's really how I approached it.

[A]

You already mentioned how in la everyone's trying to get into acting and they're taking improv classes as a career development move. Obviously not the case out here in Wheaton. What has been your observation of the people who've come in through the theater, taken the classes, and folks like me who then end up on a team? Like, how is this community different from either the one in LA or other theaters you've been a part of?

[B]

Yeah, well, every community is like the improv. It's pretty powerful for whatever reason. Like, the teams I was on in Hollywood, they were great, were very talented people. They, they did a lot of really cool things and everyone was there to grow, get better. But the thing here that I love and I think the difference between like Wheaton and like a Hollywood is people are really here to do this thing. There's no goal, you know, now some people have a goal. They're like, oh, I'd like to get on a team or do whatever. So they're smaller type of goals. But. But it's not improvised itself, is not a stepping stone for people here. It's a thing they kind of fall in love with. Doing the community is really important at Westside. It's a big thing. Like, it's supportive. A lot of people develop friendships here where the community at Second City and Hollywood felt like there were so many people coming and going, it was really hard to build a firm group that you would be consistent with for a period of time. So I think that's a huge thing that I see here. People kind of fall in love with the community and doing the thing. It has maybe a little bit of a deeper place in their world than it did at the other theaters I've been a part of.

[A]

Yeah, I was in the level one class we were a part of. I was surprised at the diversity that it drew as well. I mean, there was one father and son that was there, if you remember, there was a teenager with his dad. We had some college students, we had some middle aged people, single people, married people, retirees, widows. I mean, it was like a crazy mix of people. And I. I can only think of one other place where I've seen that level of diversity, which is a church, it's a congregation. And I'm not saying Westside is a church.

[B]

Yeah.

[A]

But in a time when so many people are segmented and siloed and we tend to homogenize our communities. Westside is an interesting cross section of this community. Let's talk about some of the. The basic lessons of improv. First off, the type of improv that we do at Westside and that you coach us in is long form as opposed to short form. Short form, for those who aren't familiar, it's like whose line is it anyway? Kind of just games that you play in really short. Define what you mean by long form improv so people have a sense of what it is you're teaching us.

[B]

Yeah, long form tends to feel a little bit more like a play. For those of you that haven't seen your team, your team tends to feel a little more short form because you guys play pretty fast. But overall, like long form improvisation, we're going to, we're going to have one interaction with the audience at the top of a show or a top of a set and we're going to explore that interaction for, you know, it could be 10, 15, 20 minutes. And the exploration of that is, is the long form. You know, there's no structure, there's no game, there's no patterns where we're spelling out and playing. We're just going to see where this thing goes. To me, I love long form more because of the possibilities. I've done stand up, you know, I've done short form. They're great, they're both great. But to me it just seems like set up punchline, where long form is exploration of humanity. And I think that's where improv comes into everyday life is like we're going to explore the human element and all the wonderful and strange and weird aspects of it. And we're going to do it in a way where we have complete creativity over it and we can be really authentic in the moment. So I love the space longform gives you just to explore.

[A]

So one of the assumptions I had going into improv was, well, it's going to train you how to be quick witted and funny. Sort of that short form idea of set up and punchline. Set up and punchline. And I was kind of surprised to discover that wasn't the critical element. It's not just how quick witted you are or funny going back to the tennis ball exercise, it's how well can you connect with your scene partner or partners. Which means listening really well and really getting in sync with them. Which means you got to get out of your own head. So talk about the listening component and the connection idea of improv. How does that work in a Scene. And then how do you carry that into other aspects of your life?

[B]

Yeah. Well, anything. If we want to do anything, well, we have to practice at it. Right. So it's weird if we want to be unprepared. Well. Or be able to navigate being unprepared. Well, we need to practice being unprepared, and that's improv. And so how do you practice being unprepared? You learn how to be in the moment. You learn how to listen, especially listen without judgment. Right. So hardest thing. Hardest thing in the world to do because we're already formulating, like, how we want to respond. We're thinking about, ooh, how does this make me feel? And all those things. And that's, you know, very. That makes sense. Right? It's very logical to go through that process. But we're. We're learning how to listen without judgment. We're learning how to just be in the moment, and that's just preparing to be unprepared. We don't know what's going to happen. Part of the process, too, is learning how to be okay with you in a moment where you don't have all the answers. Because I feel like in the world, we're trying to navigate everything and control it. Right. Because it protects us. It makes us feel comfortable. The more predictable things are, the better we feel as we do improv, as we learn how to communicate through improvisation, be in a scene where. Work with other people, listen to them, we learn that ourself is actually enough. Like, we kind of learn how to be okay with us. And that spills over into everyday life, I think. I mean, it's helped me a ton. Yeah.

[A]

I came home to my wife after a couple of lessons in the class, and she said, you know, you join it. What's going on? And I'm like. And I actually told her, I said, I think this is going to make me a better husband. She was like, what? I'm like, but it's exactly. What you're saying is, how do you really connect with a person? We do a silly exercise where you were standing in a circle, a bunch of us, and you can't speak to somebody until you make eye contact with them. And so you're able to give, they're able to receive, like just really being present, but your point of expectation. And a lot of the books I've written, a lot of the stuff I've taught over the years, have been about this dynamic of fear and control, that all religion begins with fear, and we sense the world's a dangerous and threatening place. And in our fear, we want control. And that's, you know, throw a virgin down the volcano to get the gods on your side. Say a certain incantation, or go to church and give money or take the sacrament or memorize Bible verses. Whatever your system of control is, it's all rooted in fear.

[B]

Right.

[A]

But that. That's what the improv stuff is kind of brought to the fore is, hey, you gotta give up the control, give up the fear, and just be present. Oh, my gosh. It sounds simple, but it is the hardest thing in the world. So hard to actually do. And it's the antithesis of my training, which is I had a preaching Prof. When I was in seminary who told me it's okay to have butterflies as long as they're flying in formation. Which was his way of saying, when you get up in that pulpit or that's, you have to be 100% prepared. And improv is, like you said, it's the. The training yourself to be okay, not being prepared.

[B]

Yep.

[A]

And that's crazy wild. But that's life.

[B]

It's life.

[A]

That's life.

[B]

So we don't have a script. When you wake up in the morning, you don't pull a script out of your nightstand and go, oh, at noon today, I'll eat chicken parm or whatever, you know, you don't know.

[A]

That's what people want. They want the script. And I think that's why a lot of people come to relig. It's why they come to church. It's why they. They buy certain Christian books or follow certain gurus. It's. They're going to give me the script.

[B]

Yes.

[A]

This is how I raise my kids. This is how I have my marriage.

[B]

Yes.

[A]

This is how I appease God. This is how I vote whatever the script is. And it's all to mitigate their fear.

[B]

Yeah.

[A]

So what does it look like to go, I'm just going to trust my partner here, and in this case, in a spiritual sense, my partner's God.

[B]

Right.

[A]

But it's also the people I'm doing life with.

[B]

Right.

[A]

And that's not easy.

[B]

It's not easy. Oh, so many thoughts. I think that when we are. When. When we are trying so hard to control things, when we're. When we're really out there, you know, wanting things to be predictable, I think we're robbing us of the opportunity to live life. Like, life is pretty amazing. Like, an improv scene is pretty amazing. I don't care if I'm Bombing on stage or if I'm crushing it, it's pretty amazing that I get to explore this moment and be excited about where it could go. And I think that's the thing in life is we're afraid of where this could go. I always say the same thing. I'm like, having kids is waking up in the morning and thinking of all the things you want to do that day and not getting to do any of those. Right. That's having children.

[A]

And you're responsible for the depopulation of the world now, Jeff.

[B]

Oh, okay. I'm sorry. But I'm going to stick with it. That's what happens.

[A]

No, there's truth there.

[B]

There's truth there for sure. And it took some time. And I remember thinking one day recently that I was like, I'm not being a good improviser to my children. Meaning I'm not allowing this day to do what this day is going to do. Like I'm so busy trying to keep them under control and do all this stuff and I really, about two years ago I really released that and I just decided to be present with my kids. I decided to follow the day where it takes us. And I'll tell you, I have an amazing relationship with my two daughters now. Just like they, I have a 14 year old daughter who refuses to watch a movie with me unless she can snuggle with me. 14 year old daughter who in front of her kids she'll say, I love you dad. Or in front of her peers. To me that I can look back two years and go, when I released trying to manage everything and just showed up for them as a dad and as a human, everything changed.

[A]

I'm thinking about when my kids were little, one of the things, part of the vocabulary of improv is we talk about we're gonna go play together. Which is a very childish way of talking, but it's true. We're just, we go out on the stage and two of us or a group of us are playing, we're just figuring things out. We're discovering what happens and what comes of it. And when you look at little children play, that's how they approach the world.

[B]

Yep.

[A]

They just go out in the world and go, what can I discover?

[B]

Yeah.

[A]

What can I find? And there's a, an innocence to it and a wonder about it. And as we get older, we kind of lose that and it becomes more control.

[B]

Yes.

[A]

How can I make sure that what unfolds today? I'm on top of yes. And I've got and to rediscover that as a dad, in your case, with your daughters, is is fantastic. If there's one rule of improv that people listening to this probably know, it's the yes. And yeah, you say yes and then you add to it. Do you know who Bob Goff is, if you're familiar with that name? He's a Christian writer and crazy, crazy guy.

[B]

I'm gonna say yes, just say street credit.

[A]

He's bizarre. But anyway, years ago, my wife and I were at an event with Bob and he ended up we were on a sofa and he ended up sitting on the floor in front of us like crisscross applesauce. And he's older, probably 20 years older than me, and he was giving us parenting advice. And one of the things he said to us was, don't worry, this is not the end of the episode. There's actually plenty more. But to listen to the rest, you need to be a Holy Post plus subscriber. So head over to holeypost.com skypod and sign up for just $5 a month. Not only will you get uninterrupted episodes of the Skypod, which means you'll never have to hear this dumb announcement again, but you'll also get access to everything else at Holy Post plus, including episodes of Getting Schooled by Caitlin Shess, bonus interviews, live streams, the Holy Post Book Club, exclusive merchandise, and a whole bunch more. And you'll get the warm, fuzzy feeling of knowing that you're supporting our work of creating smart, pro neighbor Christian content. So head over to holypost.com skypod and subscribe.