October 6, 2017

Just Hit Record

by StartUp

Background show artwork for StartUp

The Story Earlier this year we asked listeners to call us with questions for Gimlet Founder Alex Blumberg. Alex answered a bunch of them in an 

episode last season. But one caller’s question was so big, it needed its own episode. Skyler Gronholz had decided to make a podcast about starting up his life again after several years in prison. But he was anxious about making something bad, and wanted Alex’s advice. In this week’s episode, we find out: can making a podcast about your life actually change the way you live it? 

The Facts Mark Phillips wrote and performed our theme song. Build Buildings wrote and performed our special ad music. Additional music by Bobby Lord, Patrick Bower, Oatmello, and the band Hot Moms Dot Gov. Andrew Dunn mixed this episode. ** If you or someone you know is struggling with substance abuse, the Substance Abuse and Mental Health Services Administration has a number you can call. 1-800-662-HELP. That hotline gives referrals to local treatment facilities and support groups. And it is completely free and confidential.

Where to Listen


ALEX BLUMBERG: Hello, you’re listening to Startup. I’m Alex Blumberg, guest-hosting, as I sometimes do, for the regular host Lisa Chow. Lisa will be back in the hosting seat next week. But I’m here this week for a reason. Some of you might remember an episode we did last season. It was an episode where we asked listeners to send in questions to the show. Questions for me to answer. We had people asking us all sorts of things. Questions about how it felt to grow so fast, questions about all the TV projects that we have going on. It was a whole range of stuff. But there was one caller that we didn’t include in that episode. His question was just too big to fit in with the other ones.


ALEX: Hi, this is Alex Blumberg calling from the StartUp podcast.

SKYLER: Wow, okay, first of all it's amazing that I'm talking to you right now. I'm kind of freaking out about it. My name is Skyler Gronholz. And then you want me to tell you a little bit about why I wanted to talk to you…

ALEX: Yeah yeah, where am I talking to you from.

SKYLER: Okay, so I'm actually literally in the middle of a drive from Seattle to Bellingham. I'm moving up there to like try to officially start over my life. I got released from prison a year ago and since I've been out—so like a year ago I started listening to StartUp and loved the show. And probably by like episode four or five, I was driving to this really crappy job where I was like cleaning out rat poop and pee from like crawl spaces underneath houses. Yeah, it was really, really bad. And so I started listening to your show. And like on my way to work, I was like, “What if I started a show where I'm doing what you...you were doing for startup. But like for someone starting up their life coming out of prison?”

ALEX: I talked to Skyler that afternoon for almost an hour. And over the course of my career, I’ve talked to people who have been in prison. I’ve talked to people who have just gotten out of prison. I’ve heard plenty of stories on the radio about people getting out of prison and trying to start their lives over. But I’d never heard anyone talk about it like Skyler did. And in talking to him, there were a lot of surprising parallels between what he was going through and what anybody who’s ever tried to start something new for the first time goes through. There’s the self doubt, the fear of failure, the yearning for people to care about this thing that you’re doing. And so, today, we’re devoting the entire episode to Skyler’s story. To his attempt to restart his life. To what he did to upend that life in the first place. And to the strange, radical, and surprisingly familiar to listeners of this podcast strategy he came up with, to get everything back on track again. A warning, there is some swearing in this episode.

ALEX: Skyler told me that his path to prison started not long after high school. He’d had to drop out of college because he’d lost his scholarship. His grades weren’t where they needed to be. He was newly married, and working a job he hated.

SKYLER: I'm working construction for you know this just asshole dude. And like, I get my wisdom teeth pulled and so I start taking vicodin. The vicodin progresses into a full-blown addiction six months into my marriage. I'm going to rehab. At that rehab my roommate is a heroin dealer. So like I walk out of that rehab not with just a vicodin habit but like with a heroin habit. That's within, I think, the first week of graduating rehab, I was getting introduced to that whole world. And like, so then there was like six years of, you know, of pretending like I had it all together. Like pretending that I wasn't an addict so that my wife wouldn't freak out and like all my friends and stuff—none of them were drug addicts. My wife was getting her master's in psychology. And I'm like going into heroin dealers’ houses that are just disgusting like every single day and being this other person, being like just total total fraud. And, yeah, it just kept getting worse and worse. And so it eventually led me to stealing a projector and a few computers from the local college that we lived next to. So that I could not use the little bit of money that we had left in our account, so I could get high. And got caught.

ALEX: Oh man. And then it all came out, and your wife found out.

SKYLER: Oh yeah. She left. Yeah yeah yeah. I mean, it's my own doing, like I…Yeah, it was really bad. It sucked.

ALEX: In prison, Skyler kept himself busy with work shifts and classes. Did the crossword every day. Got himself clean. And due to his good behavior, he ended up serving just three years out of his five year sentence. After his release, he moved back in with his parents. Got that rat poop cleaning job that he hated. And he was struggling to stay positive. He was feeling more and more like if things didn’t change, he’d slide back into addiction, end up back in prison. And that is when he had a thought I would not have predicted from somebody facing what he was facing. He thought,  “I’ll start a podcast about my own life. This is what’s gonna save me.”

SKYLER: And the second I thought about it, it was like I could breathe again. It gave everything like this new kind of context, and again definitely gave me a sense of purpose, which is what I just desperately needed. And so I was kicking around the idea and like didn't know exactly how to do it. And I was actually talking to my probation officer, who's like a screenwriter by—a screenwriter by trade. He was ike a ridiculously amazing probation officer.

ALEX: Wait your probation officer is a screenwriter by trade? What does that mean?

SKYLER: Yeah, like that’s his first love. Like he's written for movies and stuff like that.

ALEX: That’s awesome.

SKYLER: Yeah, it was really trippy when I first met him.

ALEX: So your probation officer, who is a screenwriter, you're telling him about this, that you wanted to start a podcast.

SKYLER: Yeah. And so he tells me the story of like, “Oh yeah, like my first screenplay, like I was sitting on it for years until one day, I just like grabbed some...grabbed some buddies and like hit record or whatever and just started making a movie, and all of a sudden like I was making my first movie.” So he’s like, “So, when you leave here today just pull out your phone and pull up a voice memo thing and just hit record and you will be making a podcast.” So I was like, okay I'm going to do it, and like...

ALEX:  Man that..he is a good probation officer.

SKYLER: Oh, he was the best. We would we would have like two- or three-hour long conversations, and I'm supposed to just be going in there to pee in a cup for him.

ALEX: Uh huh. Wow.

SKYLER: So like I get my in car and I hit record.

SKYLER (recording): Well, I’m just leaving my probation office…This is actually my first recording of this podcast…

ALEX: This is that very first recording that Skyler made. He’s recording it into his phone as he gets in his car and starts driving.

SKYLER: I’m not starting a small business. What I’m doing is I’m starting a life. I’m 31 years old. I am two and a half months out of a 60-month prison sentence for…nine felonies. Oh no, ten felonies.

ALEX: He talks for about 40 minutes. When he finally gets to where he’s going, he turns off the engine and keeps recording. He’s rambling a little, sounding sad. And then he starts talking directly to the people he imagines listening.

SKYLER: I’m learning how to live, and I want you guys to learn with me. Um, I need your support. I need to know that you’re there listening to this. I need to know that…you care about whether or not I choose to go right or choose to go left. I need to know that my life has purpose and value. Because right now it seems like my parents are the only ones to whom my life really matters. And that’s lonely.

ALEX: After this first recording, Skyler kept at it. He recorded conversations with his brother Shane, a meeting where he applied to get food stamps, talks with his mom and dad. And all sorts of just mundane stuff.

SKYLER (unlocking door): Gosh, I have got to get this key fixed. That was horrible.

ALEX: Like this recording, where Skyler gets back to his parents’ house late one night. He walks in, plays with the dog for a minute.

SKYLER: Hi, hi hi hi, hi hi hi. Come here.

ALEX: And then you hear the voice of his mom, Debbie, who it sounds like Skyler has just woken up.

DEBBIE GRONHOLZ: He’s been so funny tonight.

SKYLER: You guys are on the air.

DEBBIE: We’re on the air?

SKYLER: Yeah. The whole world is hearing you. In the future.

DEBBIE: Oh goody….

SKYLER: I have acquired just hours and hours of tape about like my life.

ALEX: This is Skyler and me, back on that first phone call in the studio again.

SKYLER: You know seeing people again that I hadn't seen since before prison and like court dates that I had to go to. And I kind of feel like if I wasn't recording, I might not have done them. It didn't have any weight to me. Like I was kind of already expecting me...myself to fail, given that like it's like 75 to 80 percent of everyone in prison will return to prison. I set out to like I was going to defy those odds. And then all the sudden, you know after the tenth hoop that I'm having a jump through, that just seemed so stupid. I was already questioning like if I had the fortitude to actually get through this thing. And so then once I started recording, like it gave me a sense of purpose to do that stuff.

ALEX: I get that. Because because I think...I've had that experience too where...where like sometimes…like I know there's a conversation that I'll have to have or there's a thing I'll have to do or there's a thing I'm afraid to do or there’s a thing that feels like a pain in the ass to do. And if you're not recording it then it's just going to be something that happens. That doesn't matter.

SKYLER: Yes. Yes.

ALEX: But if you're recording it, then you're like well maybe it’ll matter somehow. If I share it with somebody else.

SKYLER: Yes. That's exactly how it felt.

ALEX: Okay. So, so, so, what's your question.

SKYLER: Right okay. So if I can just be like brutally honest with you.

ALEX: Absolutely.

SKYLER: Like, okay, so I—I feel like if there was anyone that I could talk to about this idea, what I want to do, like you would be number one. But like I'm not even really sure what exactly the question is that I need to ask you. I wasn't planning on saying that, but I don't want to ask you this question. I was like why did I ask him that.

ALEX: Uh huh. Right.

SKYLER: Yeah, like so I've been, I've been so obsessing on like story formula and creating a great product and you know my standards are super, super high and even though Ira Glass talks about this gap thing and like I should be okay with that. I'm not okay with like putting out an episode that sounds like crap.

ALEX: What's the gap thing?

SKYLER: You haven't heard that?


SKYLER: Oh well maybe. Maybe so…

ALEX: That guy's a hack man. No, I'm just joking. He taught me everything I know. I was just joking. Go ahead.

SKYLER: No, he, so he talks about when we first start, when you first starting creating anything, like your taste is like let's say it's set very high. But when you're just starting out, like there's this huge gap between your ability currently and, and—you need to be okay with that and you need to just start creating, regardless of the fact that like it's not anywhere close to what you want to be putting out there.

ALEX: And I would add that like…

SKYLER: Please add!

ALEX: That's like essential. Like the only way that you can get better is by, is by sucking and then learning exactly how you suck and then sort of trying to like okay well what if I do it different this time. You know? There's no other way.

SKYLER: So how do you, how do you prevent the total despair that—I've been feeling like “Oh, I'm just being a complete fraud.” It's almost like I'm fighting against this tension of like, I can't afford to waste time. Like if I screw up, if I make the wrong step here, I'm going back to prison. Like my freedom and life is at stake here.

ALEX: Is that what it feels like?

SKYLER: Totally.

ALEX: It feels like the stakes are that high? Like it's not just my podcast will suck but my podcast will suck...Get, get me from like my podcast sucks to I'm back in prison.

SKYLER: Okay, okay so. Anytime I feel sad. Like anytime I feel—even anytime I feel glad. Like any kind of emotion, like in recovery and stuff, like they talk like that it can all be a trigger.

ALEX: A trigger for what, a trigger for what?

SKYLER: Oh a trigger to go and do drugs again. And so if I let the sense of being a fraud start growing roots, or if I let shame start growing roots in any kind of way, that will possibly lead me to relapse, and if I relapse, all bets are off. I'm going to make some drastic mistake and go to prison. Like that—the line is no longer like a gigantic, you know, great wall of China. It's a, it's a little crack in the concrete. That's that's how I feel. Yeah.

ALEX: Yeah. So this thing that felt like it was saving you to get good at it..It also feels like it puts you at risk.

SKYLER: My gosh that that's exactly it—that's exactly it. So much so that like now, I just over the last few weeks…So I built this whole home studio thing and like just kept being like, “Okay, if I can just listen to enough of Alex Blumberg talking about how he does it, like I will be able to make a good product.”

ALEX: I wish it worked that way. I don't think so. I don't think you can get, get good at anything like that without, without exposing yourself to fear and feeling bad. I've never seen it happen. I've never seen it happen. But, but I also feel like I don't think you can live a life without exposing yourself to fear and feeling bad. So, I don't think it's putting you at any more risk than you're already in, you know?


ALEX: I’ve never been to prison. I’ve never used heroin. My circumstances couldn’t get more different than Skyler’s in many ways. But it was shocking, during this conversation, how familiar what Skyler was going through felt to me. We both started podcasts out of a feeling of not knowing what else to do. This vague sense that if we documented what we were doing, then maybe what we were doing actually mattered. That if we imagined success, imagined a big audience out there listening to what we were making, that one day success would actually come. And in fact, starting a podcast did bring me success. It helped me start a company. Could starting a podcast possibly help Skyler with his project, too? Restarting his own life? After the break, we find out. We send StartUp producer Molly Messick to Bellingham, Washington to catch up with Skyler. And to find out—can making a podcast about the story of your life, actually change the way you live it? That’s coming up after these words from our sponsor.

ALEX: Welcome back to StartUp. Molly Messick picks up Skyler’s story from here.

MOLLY MESSICK: A couple of months after Skyler and Alex talked, I flew out to Bellingham, Washington to meet Skyler. I found him outside his apartment building. But before we went in, we walked to a grocery store nearby so he could pick up dinner.

MOLLY: So is this sort of your normal routine? Is this a thing you do?

SKYLER: Yeah. Either walk or ride my bike.

MOLLY: When we get to the store, Skyler heads to a juice section along one wall and picks out a protein drink and a smoothie. Then he walks to the back wall of the store, steering clear of the center aisles, and gets some yogurt. Smoothies and yogurt are what he eats most of the time, he says. He’s had a fair amount of anxiety since prison, and he thinks it’s affecting his stomach. But that’s not the only reason he eats this way.

SKYLER: I’m really bad at decisions now. Which is...I mean maybe I’ve always been a little indecisive, but I think this is why I kind of do this is. That...

MOLLY: He gestures to the whole middle of the store—the produce and snacks and frozen foods.

SKYLER: ...freaks me out.

MOLLY: Like the whole grocery store.

SKYLER: Oh yeah. It gets me totally panicky, almost.

MOLLY: Do you connect that with all the decisions that get made for you in prison?

SKYLER: I mean, it has to be. It has to be. The thing that I don’t like that I judge myself, almost, for, is I wasn’t in there that long. I haven’t sat down with anyone yet, I don’t think, that did 15 to 20 years. I can’t imagine. I don’t feel like I earned the right to have these kind of anxieties. I don’t know if that makes any sense.

GROCERY STORE CLERK: Do you want a bag?

SKYLER: Yeah, please.

MOLLY: When we get to the checkout, a couple of Skyler’s cards get declined before one finally works. It seems like he knows this checkout person, and like they’ve been through this before.

SKYLER: I think we did this last time.

CLERK: Yeah. Want to try again?

MOLLY: It was just a quick trip to a grocery store, but it summed up a lot about where Skyler is right now. He’s pretty anxious, and he doesn’t have much money. And he’s constantly thinking about how prison changed him. It’s not what he expected when he was still in prison and looking forward to getting out.

SKYLER: You know those little cars that you twist up? Like the ones that you pull back and like the wheels are winding and then you let go and then you just, boom. That tension was building exponentially almost like the closer I got to actually getting out. You know my parents came and saw me like every week and the closer the date came, like the more tension was being built of like, I finally get to be me. And then I get out and the car is released. And like it just boom right into a wall and like crashes and turns upside down and you know gets set on fire. That's how it felt. Like all of that...that...that excitement and ambition just totally crashed.

MOLLY: Starting over was a lot more challenging than he thought it would be. At 31, he was back home with his parents, having a hard time finding work. His old friends from before prison weren’t around very much. And a couple of the friends he made during prison weren’t doing well.  They were back to using drugs, or back in jail. Skyler was lonely, and struggling with his urge to use again. It seemed like it was all going very badly. Which scared him, because that meant he was on a path toward failure. And in his mind failure meant relapse, and maybe prison. Skyler had started listening to podcasts pretty early—in 2006. He was a big fan of “Radiolab” and “This American Life.” And after getting out, he started listening again. With a kind of crazy intensity, by the way. At one point he subscribed to 126 shows. And one of the things he listened to was “StartUp.” When he heard it, he had a flash of inspiration.

SKYLER: It was something like, “Start recording my life as if I have 50,000 listeners every week. And start living my life as if I had 50,000 people that cared.”

MOLLY: We’ve listened to a lot of the recordings Skyler made in his first year out of prison. It’s more than 100 files. Skyler’s mom, Debbie, is on the tape pretty often. She’s an artist who used to paint illustrations for a stationary company and now teaches at the local high school. In one recording that Skyler sent, he and his mom are looking through a stack of Skyler’s old stuff from when he was a kid. They find an assignment from when he went through the DARE program in elementary school.

DEBBIE: Oh this DARE thing is…

SKYLER: Hilarious.

DEBBIE: Hilarious!

MOLLY: Debbie and her husband Marc have done a lot to support Skyler. They emptied their retirement account to pay for detox and rehab facilities. They hired a high-priced lawyer when Skyler faced prison time and when Skyler was in prison, they visited and called often. After he got out, they welcomed him back home, even though they worried a little about what it would be like to have him there. Debbie picks up the DARE assignment and reads from it.

DEBBIE (reading): “In my future I plan to be a good athlete, have a good job as a Disney artist, have a family and stay healthy. If I take drugs ,all of this could be taken away from me.” Oh! That’s a sad sentence. This is a very sad thing to read, Skyler… And then you have a scene, too. “Freeze, up against the wall. Spread ‘em.”

SKYLER: Oh my gosh, are you serious?


MOLLY: I’ve asked Skyler about this tape. He says he sounds excited because he thought this recording could be good for his podcast. And he also says that in the moment he probably didn’t want to think too much about himself as a kid, drawing a cartoon that would turn out to predict so much about his life.

DEBBIE: “Officer, what’s going to happen to me?” That’s very sad, Skyler.

SKYLER: That’s wild.

DEBBIE: You’ll have to read that on your thing.

SKYLER: It’s like a prophesy of some kind.

DEBBIE: It’s very sad.

SKYLER: I’m sorry.

DEBBIE: I’m sorry, too.

SKYLER: At least I have you to help walk me through it.

DEBBIE: Always. You were a sweet little boy.

SKYLER: You’re a sweet mom. Still are.

DEBBIE: You still are sweet.

MOLLY: When Skyler was young, he was singled out for his talents. At nine, he won an art competition and met President Clinton. In junior high, he was elected student body president. In high school, he was a good athlete, sang in an a capella group that performed for the governor, and went on summer mission trips with his family’s church. But looking back Skyler thinks he always struggled. He had a hard time focusing, and he could be impulsive. He thinks that’s why he started shoplifting when he was still in high school. He mostly took small things, he says, but he did it pretty often, and went years without getting caught. In some of his most memorable recordings, Skyler is looking backward. He’s examining his past and trying to reconcile it with where he is now, or trying to take some lesson from it. Occasionally, in those moments, he’ll learn something completely new. For example, the whole time he was in prison, he told one version of his last arrest before he got sent away. He was the victim, and the police were super aggressive. But after he got out, he read the police report. And then he went to West Seattle, where the arrest took place, and recounted the story to himself, on tape.

SKYLER: Basically my arrest was really messy. I was high on methamphetamine. I was high on heroin. I was high on Xanax. I was a mess. An absolute mess. And I get pulled over by a cop.

MOLLY: In 2012, when this happened, it was a bad moment for Skyler to get pulled over. There was already a warrant out for his arrest. So he gave the police officer a fake name. It didn’t work. The officer, a woman, asked him to step out of the car.

SKYLER: And at that point I tried starting my car again, which began a chaotic rumble and tumble and struggle. I fall out from the car on top of her, at which point she chipped a tooth? I don’t know if I was like trying to strangle her? I cannot imagine how terrifying that would be. I know I’m not a violent person. I’ve never been one to start anything. I just remember feeling this desperation. It’s like, if I could just tell you that I’m not resisting and you could let me stand up and I can explain, I would have the opportunity to keep running. To run away, you know? So I was yelling out, “I’m not resisting! I’m not resisting!” While I was completely resisting.

MOLLY: If you search Skyler’s name, the top results are about this assault. The police officer’s tooth was knocked loose. And another officer who jumped in to help had torn muscles in his chest and shoulder.

SKYLER: I don’t like thinking that I’m a bad guy, I don’t. It’s so disturbing to think that it was me doing those things and not just a stranger. Because it feels like it was a stranger.

MOLLY: Skyler told me that, at the time he recorded this, seeing himself as the bad guy was a new thing for him.

SKYLER: I do remember feeling almost excited in a terrified sort of way, I guess. That, like, I was getting to the bottom of things, and how hopeful that was, in a way.

MOLLY: He says telling the story on tape helped him see himself more clearly. It was like he lifted a delusion he’d been living under. And that was painful, but it also felt like a good thing.

SKYLER: I think it’s because if I can understand why I’m here in this shitty existence—that’s too bleak, but like—why am I here and not where I thought I’d be at age 33? Why did I go to prison? Why did I ever start doing drugs? Why did I get divorced? Like why? How did that actually happen? Because I still don’t really get it. Especially when compared to the rest of my family and my friends. Like, how did this happen? Why would I ever compromise things? Like how…

MOLLY: Why is this my life.

SKYLER: Yeah, yeah. Anytime I can answer in any way those questions, it’s like another brick that I can put into the new foundation for this new life that I’m trying to live.

MOLLY: Skyler told me that honesty is a big part of that new life he wants. When I asked him to explain what he meant by that, he told me how he used to pay for drugs before his heroin addiction got found out. He stole computers from college campuses. He would walk in, pretending to be a student, and slide a laptop into his bag. He specialized in MacBooks, and resold them through Craigslist. The people he was closest to when his heroin addiction first got found out—his wife and his friends and his family—all thought he had a paid internship, working in architecture. He would get up in the morning and dress like he was going to an office, but actually he’d go steal computers, or go to his dealer, or download a movie and watch it at a coffee shop.

SKYLER: My parents would ask, “So how’s work, you know?” “Yeah, it’s good but, boy, is it a challenge. You know, geez. I didn’t realize architecture was going to be so mathematical,” or whatever.

MOLLY: He made up co-workers he would talk about.

SKYLER: Like oh okay so, “My new boss’s name is Ryan. And he’s the nice boss. And Jake, like he’s the assistant boss. And he’s more of an asshole and rides me all the time, but he’s not in all the time.”

MOLLY: There’s a question that Skyler says haunts him. Am I still doing the same things I’ve always done? Recording helped him believe he wasn’t slipping back into that groove of telling lies about what he was doing with his life. He was documenting things. Committing them to tape. Creating a record that wouldn’t lie. Recording helped him in more straightforward ways, too. It kept him company. Most of his friends had moved on while he was in prison. They had families, moved up in their jobs, moved away. He wanted connection, and wanted to make new friends. But when he tried, it backfired. For example, he told me this story about finding an ultimate frisbee pickup game one time, after he’d been out of prison for about six months. It used to be one of his favorite sports, and during the game, he hit it off with one of the other players.

SKYLER: We were just joking around the whole time and so yeah afterward he invites me to go get a drink with them down the street. And I was like, heck yeah like this night is like awesome.

MOLLY: Skyler texted his mom to let her know he was hanging out with some new people he’d met. He says the guys he was with seemed pretty successful. Like they all had pretty good white-collar type jobs.

SKYLER: And so then they’re like, “What do you do?” And I’m like working construction.

MOLLY: Skyler felt embarrassed about it, so he said something like, “It’s not my life’s work.” They asked a few questions, and he wound up telling them about his addiction and serving time. Pretty soon, two of the guys, including one who had given Skyler his number, moved to a different place in the bar. Skyler didn’t think much of it. He just kept talking to the guy who was still there. But the conversation was different.

SKYLER: The connection was all the sudden just gone. And then I kind of start being like, oh wait are they being, like did that happen because of like me telling my past. And then after like I don't know half an hour or so of that, the guy that whose number I got, he comes up to me. He's like, “Look man, I got I got a wife and kids ,and you think you could delete that number from your phone.” Yeah, it sucked.

MOLLY: Was that like the first time you’d really tried to make friends after prison?

SKYLER: I think so. Yeah, yeah. Yeah. I...it affected me. It...it. Like I think first of all I was kind of embarrassed with how excited I was. You know, and…

MOLLY: You mean like telling your mom about it.

SKYLER: Yeah, it's, it's kind of embarrassing. But way worse to then go home and like... yeah... I can't believe I'm actually—I haven't thought about it, but, I'm sorry I'm getting emotional. Yeah.

MOLLY: Did you tell your parents about it? Did you tell them what had happened?

SKYLER: No, not...not...not like, not for a while actually. Why are you asking me that? No, because I didn't...like I…I think I just probably said it was great.

MOLLY: Skyler wanted real connection. But in the absence of that, he had his recorder and those 50,000 listeners he imagined to help him feel less alone. Sometimes he would perform for the microphone, like he was entertaining a friend. There’s one piece of tape that sticks out as an example—a time when Skyler was really hamming it up. He’s alone in his car. Driving.

SKYLER: Oh hi. Oh, what’s that? Oh I’m just in the middle of one of my crazy moments. Just going to another appointment and I’m hella late. I mean I just don’t even know if I can ever figure this shit out. Ugh. Oh oh, the appointment that I’m going to? Oh, it’s for a psychiatrist to maybe help me with being late. First time I’ve ever—ooh, no that’s not the right turn! First time ever seeing a psych doctor. Um, I think this means I’m moving closer and closer into insanity. At least that’s how I take it. I mean I don’t know how you would take it. If you can’t tell by my voice right now, I’ve lost it. The caboose has left the station. The train has left the station! The train has been derailed. The caboose isn’t even attached no mo’. You know what I’m saying? So uh, I’m parking and then I’m…I’m gonna run inside. Maybe I’ll even walk you to the door. Because that’s what a gentleman would do. He’d walk his guest to the door. Hey, and, and like it or not you’re one of my guests. And I’ve got to treat you with respect and with dignity. More so than I’m treating—hopefully—my new psych doctor. Because right now I’m treating him like a piece of shit.

MOLLY: There were other times when Skyler was performing in a slightly different way, like with his parents. Skyler says one of the most important things recording did was help him talk to them. In the past they’d struggled to listen to each other. But with a recorder rolling, their dynamic shifted. Tensions eased up, and they talked more openly. There’s a conversation between Skyler and his dad, Marc, that’s a good example of this. They’re at a place called Gators, where they’d go together for dinner sometimes. Before you hear the tape, there are a few things to know about Marc: he’s a Presbyterian pastor. And not long after Skyler got out of prison, he got a job at a charity that serves homeless people, working with men who are addicted. In other words, he’s spent a lot of time learning about addiction and trying to understand Skyler’s problems. But he also gets frustrated sometimes. He worries about how much money he and Debbie have spent trying to help Skyler over the years. That’s the jumping off point for this conversation—Marc’s sense of responsibility for Skyler, and the conflicting emotions that come with it. Skyler’s playing the part of the interviewer, asking his dad about it.

SKYLER: What does it feel like?

MARC GRONHOLZ: It feels like it’s a rock and a hard place. If I say, “Gee, I’m sorry, son, you got yourself into this situation, see you later.” Not “see you later,” but “figure this out on your own.” There’s that option. But that’s not the way I’m wired. At the same time, the flipside of that coin is it pisses me off.

SKYLER: Yeah, I hear you.

MARC: I think we just have to say those feelings are on the table, and we still love and care for each other, but it is what it is. So how does that make you feel?

SKYLER: I mean before prison, I don’t know if I ever really had much of a realistic view of life. I used to just take from you and mom. I abused the assumed roles of you being the dad and mom being the mom and me being the son. And I get myself into predicaments and you guys are supposed to take care of it. I don’t like that person. And you know I don’t see that as your guys’s role. Really at all. Now I rely on your guys’s help, but that assumed quality, I don’t think is there anymore.

MOLLY: What we’re hearing there may not sound like the most emotional connection in the world, but Skyler and his dad are both actually saying what they think and feel. And Skyler says that wouldn’t have happened if he weren’t recording.

SKYLER: For whatever reason, bringing the mic and setting it up at the table, it changed the dynamic in this way that made me look forward to sitting down with my dad or with my mom or with both. It was kind of like it was somewhat of a therapist in a way, holding us accountable, even though it was just a piece of machinery.

MOLLY: Before you started recording, what would a conversation like this have been like?

SKYLER: Well, yeah, my dad and my fighting is not…like it stays pretty cordial most of the time, but the emotion that would be there. I can’t speak for my dad, but I know for me, like, it would override my...my thinking. I would just become like this scared little child that was making his dad upset, or something. Scared child that then either acts out by totally shrivelling away and wanting to die or responds by saying hurtful things and being an asshole, kinda.

MOLLY: So recording did a lot for Skyler. But it didn’t fix everything, and it didn’t make Skyler’s challenges easy to overcome. In his tape, there are signs of trouble that Skyler often doesn’t explain or directly address. A conversation with his dad about needing legal representation. A recording of him calling the local court to try to deal with a warrant. Skyler had a few run-ins with the police during his first year out of prison. Not long after he got out, he got caught stealing a lamp and some other things from Target. A few months after that, he shoplifted two microphones that he thought would help him make his podcast. And then there’s an incident from last September, just over a year ago. According to the police report, Skyler was alone in his car, not far from where his parents live. Someone in the neighborhood saw something that concerned them, and they called the police. When the officers arrived they found Skyler with a pipe and a small amount of meth. I’ve talked to Skyler about the report. He told me he used meth a handful of times during his first year out. Maybe three, maybe seven. Definitely no more than ten. He says he doesn’t really understand that decision, and feels a lot of shame about it. And he seems both surprised and unsurprised when I tell him that it’s not something he talked about in his recordings, at least not directly. He explains that he didn’t think his mistakes had a place in the story he was trying to tell. Because his idea of what his story should be comes from church. He’s been going his whole life, and he’s heard a lot of conversion stories. Testimonies, they’re called. And those stories follow a simple and redemptive plot.

SKYLER: When you share testimony, you talk about how you were and who you were before you met Jesus, and then you talk about your conversion, and then you talk about your life afterward. And it's this very neat way of thinking about your life. And I think I really want to think about my life in the same kind of way as like prison being the conversion moment. And since then, yeah, it's been a struggle emotionally, but I haven't done the same things. And that's not true. And so I don't know how to even go about like talking about that. It's not something that I even like thinking about.

MOLLY: There’s a mantra that’s familiar to anyone who’s struggled with addiction. Relapse is part of recovery. Skyler believes it’s true. It certainly has been for him. But he still has a hard time accepting his mistakes. After he’d been recording for six or seven months, Skyler pulled together a pilot episode of his podcast.

SKYLER (on podcast): I mean I grew up in the suburbs...

MOLLY: This is a clip from it.

SKYLER: ...playing baseball in my backyard and going to church on Sundays. But at 28, everything was different. I was in jail, waiting to be sentenced to prison.

MOLLY: The episode is short, about ten minutes long, and it doesn’t include any of the tape Skyler recorded. His parts are all scripted or acted out. Like in this part.

SKYLER: For my entire life prison was the antithesis to my world. And now I was stepping into a place I could never fully prepare for. I wanted to yell out. “Hey CO, I’m fixed. I’m ready to go home now. I’ve learned my lesson.”

MOLLY: I’ve written a lot of first drafts, and Skyler’s has some classic problems. The tone’s wrong. He’s not using any of his great tape. Skyler was disappointed with it, too. It made him think, “Who am I kidding? Who’s going to listen to this? I’m never going to get an audience.” But at some point he decided that maybe he was okay with that.

SKYLER: Once I finally realized like this is way harder than I thought, it started becoming more just for me than for this make-believe audience, which I'm glad it did. I'm glad that I didn't give it up. I realized, oh, this thing has been comforting to me, and just having this phone up to my mouth in my car when I'm scared, you know, has been empowering. And I don't really want it to stop.

MOLLY: Skyler wrapped up probation early this year, in March. Not long after that, he decided he wanted to move to Bellingham, a couple of hours from his parents’ house. He’d reconnected with an old friend who lives there, and visiting made him feel hopeful. Around sunset one night, when I was in Bellingham to see Skyler, he took me to a place called Boulevard Park. It’s one of his favorite spots in the city. It’s on a big bay, and you can see craggy mountains poking up on the far shore. A couple of his friends were going to be there, and he wanted me to meet them. When we got there, there were sail boats heading in for the night and a lot of people standing around watching the sky change. A new friend of Skyler’s showed up with her puppy. And then a guy named Andrew, who Skyler met not too long ago. Skyler was happy to see them both, and pretty hyper. He was taking sunset selfies, playing with the dog, striking up conversations with strangers. Andrew wanted to know what Skyler and I had been up to all day.

ANDREW: Did he play you any of his music?

MOLLY: No, we were talking about that! Should he?

ANDREW: Oh, heck yeah. Yeah, Skyler’s the best. No, he’s got a voice of an angel. I can’t believe you haven’t heard him play.

MOLLY: So a little while later, Andrew and Skyler and I all headed back to Skyler’s place.

SKYLER: Oh that’s uh, that’s, uh, “Death of Me.”

ANDREW: Play that one.

SKYLER: Play that one?

ANDREW: Play that one first, yeah.

SKYLER: (strumming) Watch this is going to be too high now. Okay. (starts singing) Working hard to numb the pain. She turned my heart and turned insane. My life is so unordinary. I dream of when the days are plain. I can’t believe the pain I caused my friends and family…

MOLLY: Lately, Skyler has been working on something. A simpler version of his podcast. Interviews with friends and family and people he’s met, mixed with music he’s writing himself. He’s got three episodes in the works, and he’s almost finished with them. He’s not sure how great they are. In fact he thinks they’re probably a little embarrassing. But he’s trying to follow Alex’s advice. If he wants to get better, he’s going to have to work at it.

ALEX: Molly Messick is senior producer of Startup. Coming up, a Canadian startup grows into a billion-dollar unicorn. Then hits a wall. Their plan to battle back leaves investors confused.

TED LIVINGSTON: I tell them about this, and they’re like, “So we're going to build an economy around a new cryptocurrency and we're not going to make any revenue. Is that what you're saying?” I’m like, “Yeah, yeah, yeah, that’s what we’re gonna do.”

ALEX: How that crazy-sounding plan brought in $100 million. That’s next time on StartUp. Startup is produced by Bruce Wallace, Luke Malone, Simone Polanen, Emanuele Berry, and Amy Standen. Our senior producer is Molly Messick. We are edited by Annie-Rose Strasser. Production assistance and fact checking by Max Gibson. Mark Phillips wrote and performed our theme song. Build Buildings wrote and performed our special ad music. For full music credits, visit our website. Andrew Dunn and Ian Scott mixed the episode.  Special thanks to Debbie and Marc Gronholz, Shane Gronholz, Zach Siegel, and Pat Walters. When his episodes are ready, Skyler plans to start posting them at fellpodcast.com. That’s F-E-L-L podcast dot com. If you or someone you know is struggling with substance abuse, the Substance Abuse and Mental Health Services Administration has a number you can call. 1-800-662-HELP. That hotline gives referrals to local treatment facilities and support groups. And it is completely free and confidential. To subscribe to StartUp, go to Apple Podcasts, or whichever app you like to use. Or check out the Gimlet Media website: GimletMedia.com. You can follow us on Twitter @podcaststartup. Thanks for listening. Lisa Chow will be back next week. We’ll see you then!

Music: “The Death of Me” by Skyler Gronholz

We do our best to make sure these transcripts are accurate. If you would like to quote from an episode of StartUp, please check the transcript with the corresponding audio.