Note By Note With Cole Cuchna

We explored Sacramento with the “Dissect” host to discover how he became one of the voices of the podcasting boom — and discuss what’s gained (and lost) as his platform has grown

Cole Cuchna, host of Dissect, pictured on a hot August day in his hometown of Sacramento (Photo by Cesar Jimenez)

 

This piece is a cover story from Creator Mag.4 — physical editions are available now.

 
 

“I’m my brother’s keeper if you listen and you dissect / All I talk is money if you listen to my dialect”Pusha T, “Pray For You”

From the outside looking in, the capital of our most populous state is often defined by what it’s not.

It is not the sprawling tech metropolis found a mere hour-and-change drive away in San Francisco, nor the entertainment hub of Los Angeles situated to the south. Yet in late August, I find myself in Sacramento for the next 24 hours, curious to explore a city I know barely anything about while diving into conversation with a creator whom I feel like I’ve known for years.

And just like this place, a place where he’s lived for pretty much his whole life, that creator can tell you a lot about being overlooked and counted out . “One of my nicknames in high school was Fieval,” Cole Cuchna tells me, referring to the young mouse from the 1986 animated film An American Tail. “I was super small,” he says, before motioning to his head, “and I used to wear a big hat.”

For additional viewing, check out the remastered story on our channel.

But the similarities extend past Cole’s stature and to his odyssey through the music world, an odyssey that’s seen him do everything from sleeping on hardwood floors while touring with his indie rock band to launching one of the world’s most acclaimed podcasts while raising a family.

“I started doing these little episodes in my garage…now this thing is having a slight impact on the way people think about music,” Cole says. “Which is the overarching goal of the show, of course.”

And, fittingly, it’s here, sitting at the coffee shop he worked at before achieving a long-held dream — making a living off his own creative venture — that we dissect his odyssey.

It’s been a busy year for Cole. When he’s not preoccupied raising his two young daughters, he’s spent time chatting it up with Grammy-nominated rapper Cordae and working on his first-ever TedTalk, the latter which he delivered to a Berkeley crowd in the spring. This October, he began rolling out the tenth season of his show — thirteenth if you include all three mini-series, like the one about Bo Burnham’s comedy special Inside that wrapped in June.

Past the sheer numbers in his booming back catalog, since he started Dissect in 2016, recording soliloquies in his closet late into the night, the aperture of people that have come to appreciate his work is growing wider. According to analytics tool Chartable, Dissect regularly ranks as one of the most popular podcasts in the music genre, boasting a 4.9-star rating (out of five) across nearly 12,000 reviews. Quartz named it the “Best Podcast of 2017”; the following year, New York Times critic-at-large Wesley Morris wrote that the show “thrives as an achievement of contemplative audio”; and in 2020, Dissect took home a Webby, an Oscars-esque award show that “celebrates the wide variety of things that happen online.” 

However, Cole will be the first one to tell you that his show isn’t for everyone. Its ninth season analyzes Mac Miller’s two companion albums, Swimming and Circles; each episode — running anywhere from thirty minutes to a full hour — tends to dive deep on the meaning behind every note and every line of a single song.

This amounts to eighteen installments and roughly fourteen hours of audio throughout Season Nine. For anyone who’s not a superfan of Miller (or podcasts themselves), that’s a lot of time spent getting familiar with the late rapper’s work, a true commitment in today’s highly-competitive and content-laden media landscape.

Cole knows this is a big ask, sustaining interest when attention has become such a coveted asset. Therefore, to complement his longform work across seasons of Dissect, he started experimenting with quick-hitting TikTok videos that analyze some of his favorite verses in less than a minute. Like many creators looking to reach a larger audience, he’s been successful in driving increased brand awareness, growing to over 600k followers on the app. It’s also given him an excuse to experiment with different styles and formats, as well as cover a wider array of artists in smaller doses, from MF Doom to Olivia Rodrigo.

With the six hours he spends writing every day – and five thousand words he strings together every week – one would think that throwing shortform video production on top might be a bit overwhelming. Though he now manages a small team of producers and co-writers, Cole is somehow working just as much now (if not more) as he was when Dissect was nothing but a passion project, stealing moments in the hours after he put his first daughter to bed.

“I never want to turn my back on what got me here,” he says. “So I thought if I gave away too much, you naturally run the risk of it turning into something else.”

That dedication has clearly paid off in more ways than one, but a certain April tweet stands out by representing how wide that aperture has truly opened. Cole’s audience had become fit for a king — or rather, The King:

Yes, LeBron James reacts to viral clips on social media pretty often, and sadly, he quote-tweeted a Twitter user who had reposted Cole’s TikTok, not the original creator’s account. Yet the NBA superstar’s post felt emblematic of something more, a manifestation of how far Cole’s come — and the growing influence of his platform within the entertainment industry and beyond.

This was the backdrop for our first conversation over a Zoom in May. I kick things off by asking Cole if he thinks that a set of lyrics from Pusha T’s new album (“I’m my brother’s keeper if you listen and you dissect / All I talk is money if you listen to my dialect”) were a direct reference to the show, especially given fans were theorizing as such. The creator doesn’t want to jump to any conclusions, as he’s never talked directly to any of the artists he’s covered. But through the tweets and the name drops, the signs are there, confirming the respect he’s gained from all types of different tastemakers.

“I’ve heard though grapevines, from camps and stuff, they’re aware of Dissect and what we cover,” Cole says. “I do think it’s reached a certain level…especially because the industry is so small. It seems really large, but a lot of these publications and streaming services, they’re all in talks, all the time.”

Breaking into that industry, an industry where connections are paramount and insiders hungrily search for the next big thing, is certainly no easy task. Five years ago, a betting man would probably not have tabbed Cole as one of the faces — or rather, voices — of the podcasting boom. Given he was on the older side of 30 and had no real celebrity status attached to his name, Spotify’s decision to acquihire the creator and his show was not the slam dunk it appears to be in hindsight. 

It’s the core Dissect community, though, that’s powered him along every step of the way. In an era where art is fleeting and meaning gets swept away in an algorithmic current, Cole’s listeners relish in the continued conversation around contemporary masterpieces. Dissect, therefore, acts almost as a subreddit come to life, steered by its classically-trained and culturally-literate audio creator. 

“There’s a world in which…I ended Season One. I had probably 1,000 listeners at that point,” Cole says. “And I was like, ‘Am I really gonna spend x amount of hours of my life producing something for 1,000 people?’”

“But there was a small audience I could tell really, really cared,” he continues. “And I kept doing it because I loved it.”

As I step outside my Airbnb, the sun is just rising over the city, yet to reach its steamy apex. Cole had mentioned how Northern California is experiencing a late summer heat wave, and a quick glance at my phone confirms his note, with the afternoon temperature estimated to reach triple-digits. Therefore, we agreed to meet up at 9 a.m. to maximize our time outside, and with a stroke of luck, it appears like Helios is holding up his end of the bargain.

Save for a couple runners and a light breeze, it’s pretty quiet as I amble along the banks of the city’s titular river. My path soon turns into a walkway over the Tower Bridge — a structure more golden in nature than its younger cousin over in the Bay — and I stop to watch the water glisten beneath me, ultimately crossing into Old Sacramento.

As its name implies, this area of town houses architecture dating back to the 19th century. Historical Gold Rush-era buildings, such as the Pony Express’ western terminal, neighbor local attractions like the California State Railroad Museum. It’s pretty empty right now, but by midday, the old-fashioned riverboat cruises will power up their engines and guide tourists around the city.

Our photographer, a friend-of-a-friend named CJ, is a transplant by way of Santa Cruz. We meet up about thirty minutes before the shoot is scheduled to begin, and I ask him to dish his perspective on the city he’s now called home for the last eight years. The vibe stands in contrast to the beach town where he grew up, CJ tells me, but he came here for college and never left. Between paying gigs and nights out with friends, he loves to dedicate his time to discovering new spots through the local music scene, which he describes as thriving.

It’s fitting, then, that the conversation continues on when our subject arrives. As we start with the Tower Bridge and proceed to various backdrops, CJ and Cole swap stories about that same music scene, and how it’s evolved. Along our walk, Cole points out various venues and speakeasies where he once performed throughout the aughts.

Cole pictured in front of the Tower Bridge, a golden landmark spanning the Sacramento River (Photo by Cesar Jimenez)

Sporting a plain white tee, dark pants, and a black-and-yellow pair of Air Jordan 1s, Cole’s minimalistic style pairs quite naturally with his lowkey demeanor. Confidence — in himself, his work, and his belief system — oozes from the second we first shake hands, a carefree coolness accentuated by his unostentatious swagger. Throughout it all, his silver hair shines in the Sacramento sun, complementing his shades in an effortless fashion.

That style was born out of his teenage years, when all he wanted to do was skateboard. “Ironically, I was probably dressed like this,” Cole laughs. “Here I am, twenty years later, still dressed the same way because it’s now in fashion.”

The sneakers, the culture, the bootleg VHS tapes filled to the brim with trendy tricks and copyrighted David Bowie tunes. It was Cole’s first obsession, hanging around the skatepark after school and for “more than eight-to-ten hours a day” during the summer months. “I was just a skater kid,” he recalls. “I had no interest in girls.”

Towards the end of high school, however, Cole decided to try his hand at something new. Red Top Road — a local indie rock group— had quietly grown a small-but-loyal following for over a year by the time he joined at 18. A self-taught guitarist and pianist who had played with friends since middle school, Cole embraced band life to the fullest, performing from basements to clubs —even hitting the road after a short stint in undergrad.

“I actually had a lot of success at that age,” he reflects. “We were signed to a little record label. We did some tours, we put out three albums…I took it for granted back then, but I look back and am like, ‘Man, that was a lot to do at 19.’”

After traveling a bit, sleeping on floors and living off of fast food, Cole was hooked. With the initial experience under his belt, Cole decided to leave Red Top Road and join forces with a childhood friend under the pseudonym “The New Humans.” As they looked to artists like Muse and The Killers as inspirations, the group picked up a bassist and drummer while ushering in a unique sound: no guitars.

“That’s a big thing right now…it’s so common,” Cole says. “But back then, having just piano and synthesizer in a band that sounded like a rock band was kinda a novelty.”

In late 2009, they began to generate some buzz ahead of their debut album, with music magazine SubMerge describing their sound as “sugary, glam-y, coked-out even.” When scouring the internet, one can find some old camcorder footage of The New Humans performing that EP, Avalanche, on stage the following year. A young Cole appeared to be in his element on stage, a feverish spirit at keyboard as raucous audiences reciprocated his energy.

The goal was to take it to the next level, to sign a deal with a major label and graduate from those hardwood floors. The group never quite put it all together. 

“It was very much a challenge to be in a band with people that weren’t as committed as you were, that weren’t pushing themselves to be better all the time,” Cole says. “At some point when you’re trying to make it, your band members become your business partners. You’re like, ‘I love these guys, but can I rely on them for my livelihood long-term?’”

It’s a cliché tale, the band breaking up and going their separate ways. Yet Cole can’t help but think about the what-ifs. “I felt like we had a chance if we gave it more time,” he reminisces.

After a decade of teaching himself how to write, produce, and perform, he decided to hit a soft reset, attending college to study classical theory and composition.

Thus began his first foray into music education.

We stop to take photos by the Kings’ new-ish arena, the Golden 1 Center, which opened in 2016. For years, insiders believed the franchise would pack its bags and move up the coast to Seattle; however, new ownership struck a deal with the city, and a state-of-the-art venue was erected. It’s been part of a growing effort to revitalize downtown, and Cole mentions that in a couple weeks, he’ll be seeing Kendrick Lamar perform here as part of the rapper’s Big Steppers tour.

Cole wasn’t listening to as much hip hop—or any chart-topping music, really— when he arrived at Sacramento State as a 27-year-old freshman in 2011. He was more preoccupied with the fact that many of his peers were nearly ten years his junior, and he had a lot of catching up to do.

“I’m suddenly surrounded by musicians who have been formally trained for their entire lives, and they were just exponentially better than me,” Cole says. “It was just a huge reality check…I think everyone’s a little more arrogant, or egotistical, in your young twenties. You feel like you have the world figured out.”

He felt like a “transplant,” a “foreigner” in this academic setting. So when he struggled to keep up in some of his classes, he started looking for alternative sources to supplement his education. There weren’t the same amount of easy-to-access resources found online as there are today; MasterClass wouldn’t be started for another three years, and YouTube was known more for viral clips and sketch comedy (for a bit of a time capsule, John and Hank Green’s beloved show Crash Course had just debuted that fall).

What Cole did find was “The Great Courses,” a series of college lecture-esque audio and video courses originally conceived as VHS tapes in the nineties. One of the most well-rated collections came courtesy of Dr. Robert Greenberg, a world-renowned composer and then-professor at Berkeley, who — through the courses — explained composition from the Mozarts and Beethovens of the world. Greenberg also explored his theories around how to, quite simply, “listen to and understand great music.”

“I was taking every single course,” Cole says. “I must’ve listened to literally hundreds of hours of his courses.”

The creator realized that he really liked learning over audio in this fashion, these thesis-driven lectures that served two purposes: explaining why we should care about an artist and diving into the detailed analysis of their music. As he continued to pursue his degree and unlocked a passion for education, something about the classes he took didn’t quite resonate the same way that Greenberg’s courses did. Even as Cole himself had trimmed his listening diet and dedicated his studies to unfamiliar genres, there was a key insight he made from observing his peers.

“Anything contemporary was 100% absent from what you study musically in college,” he explains. “And I always thought that was odd. Even among the really talented people who were playing classical music, they would also be listening to Kanye West.”

Sacramento's downtown renovations center around the Kings new arena, where Cole often attends concerts and Kings games (Photo by Cesar Jimenez)

Cole graduated in 2015, and things started to settle into more of a steady routine. During college, he had begun working with Temple Coffee Roasters, a beloved local chain of upscale cafés; he trained new employees and took on a role as Creative Director, building out the brand’s online presence. Family became an even more important part of his life, too, as his wife gave birth to their first daughter and they spent more time with his parents, who still lived nearby.

However, that steady period wouldn’t last. Something came along and disrupted his life in ways he could have never predicted. It was an album by an artist whose rise Cole had completely missed out on during his time in college, Kendrick Lamar’s Grammy-winning record To Pimp a Butterfly.

Cole was blown away. He’d skipped over a whole era of hip hop, yet he wanted to pick apart every little detail all the same, investigating every note and every line. And while Kendrick was finally getting his accolades (with no Macklemore to get in the way), Cole felt like the reviews and critiques out there fell short in giving this piece of art its proper due. He wanted to explore the music in a similar way that Greenberg had done with Mozart and Beethoven — by immersing himself in it — and he believed that a lot of people out there shared his same interest, too.

“There’s this initial pressure to have a take [nowadays], to form an opinion…it’s becoming quicker and quicker. And then the conversation dies, and no one talks about it anymore,” he says. “And it’s just, like, we can’t do that to art. I know the Internet makes us do that even more now, but there has to be spaces where we take our time, or we can revisit pieces of art.”

Given the amount of time he spent taking care of his baby daughter, he was listening to more podcasts, such as the uber-popular true crime show Serial. The medium seemed like a good space for more in-depth storytelling, so without overthinking it, he grabbed a mic and recorded his now-trademark intro. Welcome to Dissect, longform musical analysis broken into short, digestible episodes. I’m your host, Cole Cuchna.

“The name Dissect was literally the first one I thought of,” Cole says. “The first thing you hear in Episode One was the first thing I ever put on paper. I had an idea, and I hit go.”

There was no product roadmap. There was no go-to market strategy, and certainly no pitch deck. There was a creator, and a makeshift studio in his garage.

All that was left was to make the damn thing.

As the dry California heat slowly seeps in, we finally arrive at the Temple Coffee Roasters Cole once worked at. Set amidst the bustling neighborhood east of the capitol building, the shop’s K Street location in Midtown trades sterile corporate office parks for a more flavorful slate of diverse restaurants and punchy murals. The baristas greet our interviewee warmly, and upon continuing our conversation at a table outside, he mentions that he helped design this space in his past life, even laying pennies by hand to give the floor its copper sheen.

Cole has gotten more comfortable with this part over the last several years, the photos and the talking about himself. It’s more familiar terrain now that Dissect has reached the highest levels of the podcasting world, and interviewers like myself regularly come calling.

Still, straying away from his natural disposition doesn’t come easy. “Chit chat about whatever…I just suck at that,” he explains. “I’ve always been really bad at parties because I couldn’t sit there and bullshit for that long. I’d end up in a corner with someone, talking about something…”

“Like, ‘Nietzsche has this to say,’” I interject, referencing the German philosopher who Cole used to analyze a track from Season Two. “Yeah,” the creator responds. “I’ve always been that way.”

One fan of the show picked up on its host’s introverted tendencies back in 2017, the first time he reached out over DMs to set up a call. “The way Cole brings a certain degree of humanity into what he does is why he’s good,” the fan tells me over Zoom. “And I saw that early on…Cole is beautifully awkward.”

“I say that in the best possible way with respect, because I would consider myself to be somewhat awkward as well,” the fan continues with a grin. “But that awkwardness is really about him being open and curious, smart and creative. And I think it all comes together in someone who’s honestly and authentically himself.”

That fan is Courtney Holt, the former Head of Studios and Videos at Spotify. Over the last several years, Courtney played a major role in the company’s podcast push, landing exclusive deals with talent such as the Obamas, Prince Harry and Meghan Markle, and Joe Rogan. But in 2017, he was a new hire tasked with formulating Spotify’s original content strategy, when there were only 2,000 podcasts on the service. His team decided to hone in on the medium after a company hack week, where “a bunch” of engineers — who had started to get hooked on said medium themselves — were testing out different ideas to better integrate podcasts into the platform.

“When we were trying to think about different angles to take the podcast business in, I thought music storytelling was one that was really important. And I realize that it’s a category where you’re either really good, or not so good,” Courtney says. “I started listening to what Cole had done with To Pimp A Butterfly…here’s a person who feels like he has a really deep connection to — and understanding of — the music, and he’s doing something that I had never really seen or heard before.”

We settle into conversation at Temple Coffee Roasters, where Cole once worked before going full-time with Spotify (Photo by Cesar Jimenez)

During Season Two, Dissect began to pick up more traction. That original thousand listeners proved to be a small-but-mighty group, standing behind the creator’s work and referring it to friends in droves. Plus, a handful of music blogs wanted to talk with him about this innovative new show. Ironically, they were the same publications who inspired Cole to launch Dissect in the first place due to a perceived gap in their coverage, but the positive publicity was a win nonetheless.

“I can point to a Complex article about Season Two that really kicked things off in terms of the visibility of the podcast accelerating,” he says. “Obviously all of the work I had put in up until that point had gotten me to that position…but I think everyone has little benchmarks in their life that they can point to.”

That’s when the offers came pouring in, too, from companies, managers, and networks alike. Most were simply exploratory, a chance to peek under the hood of the next big thing in audio storytelling. Some wanted to place ads on the podcast and take a cut. Others wanted to beef up their production team and bring Cole in as talent. It was a learning experience for the creator, as he was finally in the driver’s seat, a distinction from the years spent touring in his twenties.

“People only come to you when you have something already, right? You realize very quickly, like, people come to you when they perceive you to have value to what they’re doing,” Cole recalls. “So it’s all a fucking game…we all understand I’m looking for you to benefit, and you’re looking for me to benefit, and you just try to find the partnership that works the best for both people.”

While the business side was starting to come into focus, deep down, Cole knew his current creative pace wasn’t sustainable. His days were starting with a pen, paper, and cup of coffee at 5 a.m. before heading off to his job at Temple. His evenings consisted of family time with his wife and daughter, and when they nodded off, he was back in the garage, or closet, recording past midnight. And the next day, he’d wake up and do it all over again.

“The show would not have existed past Season Two if I didn’t have the capacity to do it full-time,” Cole states matter-of-factly. “My wife probably would have divorced me because I was doing way too many things, spreading myself too thin.”

Going back to his band days, though, the creator never really cared about the fame or the riches. He stood behind the artist’s mentality: he just wanted to make “the thing”— whatever that thing was at different stages of his life — to the best of his abilities, keeping it “as pure as possible.” He didn’t want to spend his days selling the ads, and while he spun up a moderately-profitable Patreon that peaked at $2,500 in monthly revenue, it had a ways to go before it matched his full-time salary.

So when Courtney reached out — first as a fan of both music and Dissect, then as a corporate figure with a strong vision for what the show could become — the pitch was clear. “The goal was for him [Cole] to be a producer of podcasts and collaborate with different teams, because it’s important that we extract the value of what his DNA is,” the former studio head says. “Cole was, far and away, the first in-house creative executive…his job was to do what he did, but also to scale it so that we could figure out how it was meaningful to the company.”

For the creator, the decision was even simpler. Out of all the people who had reached out, Courtney was the only person who was able to explain what Dissect was and articulate why it worked. Therefore, Cole could continue to do “the thing” under the umbrella of one of the biggest music streaming platforms in the world, changing his life and career through more resources and a steady income.

Or, he could quit after Season Two and stop doing the thing altogether.

Unsurprisingly, Cole chose the former.

At the end of every season, Cole posts a brief message in the official Dissect subreddit, usually in the form of a Notes app screenshot. The host asks members to think about their biggest takeaway from the season, condense those thoughts into a thirty-second recording, and send them to him over email. As the outro music fades in during the finale, Cole leaves the audience with all of the submissions, stitching together half an hour of extra audio and letting it roll.

What follows is often deeply personal looks into the hearts and souls of fellow listeners, echoing not just what the art of a Kendrick or a Beyoncé or even a Bo Burnham means to people, but also Cole’s work — and the creator himself.

Hi, my name is Sarah, and I’m from Chicago, we hear from one Season Nine submission. Swimming is one of the first albums that really helped me process my father dying — he died about six months after its release from addiction. This is one of my favorite seasons so far, and I kinda realize that as long as I keep moving, I can swim forward. So thank you to the Dissect team.

This is the community Cole has so carefully crafted, the trust he’s gained by showing empathy to both the artists he covers and the listeners who keep tuning in. He knows how intimate this form of audio storytelling can be — when we turn on our headphones and press play, his voice is speaking directly in our ears, after all. That’s why he continues to go the extra mile, cultivating the relationships he’s formed.

“If someone recognizes me, or is interested in me, I understand that’s cool because the show is super nerdy. It’s not just because they saw someone’s name on TV a lot…no, they actually are really invested in this thing that I’m really invested in too,” Cole says. “Anyone I meet that’s interested, I’m like, ‘Oh, I’ll probably get along with this person.”

“The community around Dissect, I’m really proud of, just because we’re all probably like-minded and interested in the same type of things that I think are important,” he continues.

The people drawn to his podcast are anything but a monolith, however. Listeners span state lines and continents, backgrounds and professions, brought together for different reasons yet sharing nothing more than a WiFi router and a love for music.

Nick, a 19-year-old college student from Montana, was looking to multi-task during nighttime DoorDash shifts, and he discovered Dissect when looking for a way to learn about a topic (music) he was interested in. As a fan of Tyler, The Creator, Nick gave Season Four — centered on Flower Boy — a listen, and he’s been hooked ever since. “Having someone to be able to concisely say some of the more abstract things and put it in a really approachable way is really, really nice,” he tells me over Zoom.

“What I love about Cole is you can always feel his passion, coupled with his superior technical knowledge… that’s why the way he gives off takes stays with you,” Muhammad, a 31-year-old pharmacist from Jordan, DMs me over Reddit. “Even though I’m a firm believer in the ‘death of the artist,’ I’ve never felt that Dissect imposes an interpretation, but more highlights possibilities and intricacies that the artist themselves might’ve not been consciously aware of.”

Pursuing this piece forced me to look inwards, too. Like many listeners, I started following Dissect after a friend recommended the show in 2018. A longtime fan of hip hop, I was initially captivated by Cole’s educative cocktail mixed with a shot of cultural commentary.

I stayed, however, because of the fascinating group of peers like Sarah, Nick, and Muhammed, some of whom I’ve gotten to know through interviews and Discord channels over these last several months. Cole has explored countless concepts and themes that have resonated with me, but I can point to a specific moment when this collective genuinely changed my life.

We stop by the California State Capitol Rose Garden (Photo by Cesar Jimenez)

In December of 2020, I was driving home for the holidays, having just wrapped up my fall quarter of classes. The fourteen-hour road trip wound its way through monotonous midwestern highways, leading to quiet introspection, asking myself why I was at such a low point mentally, creatively, and even spiritually.

As the pandemic continued to force many of us inside, siloed off from friends and family, I had pretty much accepted that my senior year of college had ended before it even began. Hell, I could buy a beer legally for all of two months before the lockdowns commenced in earnest. If this is what my personal transition from adolescence to adulthood was going to be like, so be it, yet it felt as if an entire chapter of our lives was ending with a silent whimper.

Which is why Season Seven couldn’t have come at a more optimal time for me. I listened through all of Cole and co-writer Camden Ostrander’s dissertations on Because the Internet, a Donald Glover album about finding meaning and connection in the age of, well, the Internet. As highway rest stops came and went, one episode led into the next, and I found myself reexamining the pure loneliness that I had internalized over the several months prior, feelings driven by a misguided belief that things couldn’t get better. Because, as it turned out, a lot of other listeners were struggling, too, and they voiced their vulnerabilities as the final credits rolled.

I tell Cole all of this, about how his show reinvigorated the sense of purpose – connecting people around an underserved niche – I’ve found through my creative work. I ask him what it’s like to hear stories like this, the impact he’s had on listeners such as myself, all because he persevered and kept hitting record.

The creator pauses before answering. “I think in the beginning, it felt really good,” he finally responds. “Mostly because it all revolved around art, and music. I think that in Season One, there was probably 10 minutes of [fan] submissions, or maybe even less than that…to see how that’s grown since then has definitely been really cool.”

Cole states multiple times that he doesn’t take that love for his work, that commitment, for granted. Underlying his sentiment is a palpable current of tension, though. For someone who’s spent years listening to artists he’s never met, Cole knows what it’s like to form parasocial relationships. I can sense that — even ten seasons in — he’s still grappling with the fact that many of his audience members have now done the same with him, too.

“Like, you just shared a really great story. I really appreciate the story,” he explains. “And having been on the other side of a parasocial relationship, I understand the feeling deeply. But being on this side…it almost can cause, like, guilt. I get these emails [from fans] — really sincere emails — and I just feel totally inadequate with what to respond with. Because the connection is just not the same…the relationship is inherently one-sided.”

He expands upon this “strange” dynamic, stressing that he wishes he could explain it better, as he doesn’t want to sound ungrateful. But he believes these feelings are also important to communicate because in the vast world of influencer marketing, social capital is the currency. It’s the reason shows like Dissect can exist. Whether through advertising, products, or something else entirely, creators are selling trust, and not everyone leads with the same pure intentions as Cole.

“I guess I’m being much more transparent about that relationship aspect… because I don’t think it gets talked about enough,” he says. “And as more and more creators find independent, niche audiences, it’s something we need to be more conscious about, especially when [some] people are exploiting those fan relationships for money.”

The thoughtfulness Cole has for this topic — and empathy he holds for artists and his community alike — truly shines through. That’s how I’d summarize pretty much every topic we cover, as he constantly provides authentic insights in his own quiet, quirky fashion.

Or, as Courtney might put it, that trademark “beautifully awkward” way.

As we finish up our drinks and head back towards the Old Sacramento waterfront, the sun nears its apex, congratulating our productive morning with a cruel, unforgiving sneer. Cole mentions that the city had been “getting really exciting” in the years since the Kings’ new arena opened, and with rent prices skyrocketing across the state, transplants were moving here, chasing the California lifestyle without burning a hole in their pocket. The creator thinks that the pandemic put a dent in this momentum, yet if outsiders continue to sleep on Sacramento, so be it — he’s not leaving anytime soon.

Besides, things seem to have once again settled into a more steady rhythm for him, as steady of a rhythm as can be when raising two young daughters. His parents still live nearby, and he mentions how nice it’s been to have them watch the kids every once in a while. 

When I ask what’s next for the creator past Season Ten (which covers Tyler, the Creator’s IGOR), Cole says that he’d love to write a book one day, maybe even a movie script. The main goal, however, is pretty cut-and-dry: he just wants to keep making the thing, continuing to put out seasons of Dissect at its current pace for as long as possible.

The creator often wonders how the external recognition will affect the engine that’s powered his show since its inception. He couldn’t be more proud of the expansive back catalog he’s built, of course, yet he might have to rethink the way he distributes his content.

“As the numbers get bigger, the community itself is less,” Cole surmises. “It almost can’t sustain that much exponential growth. Because some of the conversations that are starting to happen in the comment sections, I’m just like, ‘Really?’ Some of it’s out of my control…I can definitely feel the shift as the accounts grow.”

We make our way under the K Street underpass, home to various murals and graffiti (Photo by Cesar Jimenez)

He’s struggled with this responsibility at times. When more people are tuning in, the pressure to live up to their expectations can mount. Plus, there’s the added element of success people don’t usually talk about. 

“For me, I had this 20-year-long goal of doing something that you love and making that your living. Once you achieve the goal, you kind of had this scenario…like, whatever you imagined that would mean, doesn’t actually end up being the reality of it,” he shares. “And that can really throw you for a psychological loop, for sure.”

At the end of the day, though, the creator acknowledges that his more basic, day-to-day problems have minimized in scope. His arrival on the international podcast stage couldn’t have come at a better time, and he was put in a unique position: Spotify has since restructured the way they draw up contracts for talent, and Cole was grandfathered in as their first full-time podcast hire.

“At least weekly, I think about how crazy it is that I get to do this for a living. The shock was never lost on me…I get to do what I love, and I get paid fairly well for it,” he says. “It’s really great because there’s a part of me that’s always needed a creative outlet, or else I feel gross. Even though I have a great family and great wife and all of that…I think most creatives understand that.”

What he’s continued to have control over since the onset, though, was the dedication to his craft, finding a niche people really cared about and stewarding a differentiated product that put their interests first.

“I don’t think Cole is taking anything for granted,” Courtney observes. “But I also don’t think Cole is unable to acknowledge the reason that he is successful is because of himself. And we were lucky enough to meet at a point in time when I could be participating in this ride with him. But candidly, he would have gotten there with or without me, and that’s what I truly believe.”

The longtime media exec adds on his belief that podcasting is “now seen as a viable format for global storytelling,” and early adopters like Cole have helped usher in a new golden era of audio. Progress might be a squiggly line, sure, yet creators across domains don’t always need to craft a venture on their lonesome. Sometimes, joining an organization or team with one’s best interests at heart can pay off in a big way. It helps that Dissect is performing well, of course, but Cole praises Spotify for staying true to their word, continuing to support his editorial independence.

“I think the biggest takeaway for other people would be, like, don’t say yes to the very first thing that comes along because it feels good,” he says. “I get the pull of, ‘I’ve been working on this thing for so long. Finally someone’s paying attention.’ And you can really easily say yes to a lot of bad things. You really gotta see if it sits right with your gut, if it’s the best move for you long-term.”

As we approach the waterfront and say our goodbyes, I wonder what the skater kid with the big hat would think about where his odyssey has taken him. While his career did eventually take off in unexpected ways, some things have never really changed. His bands never quite made it, and he’s still right here, having never left his hometown. He still stops by the same coffee shop where he once worked, wearing the same clothes, flying under the radar as he slowly types away in the corner. Even the scripts he spends his days writing aren’t too far off from the papers he once penned during college.

Yet there’s something reassuring about those consistencies within the context of Cole’s grander arc, something beautifully human in its cohesive messiness. It’s a reflection of the lengths it takes nowadays to plant roots, the intentionality necessary in building something that creates true meaning in people’s lives. It’s a testament to the benefits of longevity and perseverance at a time when those values aren’t held on a pedestal the same way they once were.

Through the power of his community, he’s paved his own way over the course of two decades, finding his voice in an industry infamous for its volatility. The rhythm he’s currently in will not last forever — it’s the nature of the game, after all, and Cole might know that better than anyone. But that fearful realization continues to keep him motivated, pushing him to new heights and benchmark moments.    

While some things stay the same, his story, like all of us, is still being written, the same way Cole dissects every album on his show:

Note by note, line by line. 

For a physical copy of the magazine, check out our shop here. Coverage from Creator Mag.4 continues on.

Thanks to Jansen Baier, Cesar Jimenez, and Peter Warren for contributing to this story.