Jake Silberman wasn't a theater kid. He'd never been in a play or even given a speech. So when he got onstage for the first time at an open mic in his hometown of Minneapolis, and found 120 sets of eyes staring back at him, Silberman was terrified—and it showed.

"You know, you just freeze," he says. "I was so nervous, I couldn't get the mic out of the stand, so I just left it there. I made all these weird, desperate comments about jerking off."

Though he practiced in his basement for weeks, solo rehearsals can't really prepare someone for facing a crowd of strangers and their self-esteem-shredding silence. Silberman's material landed with a thud—his last-gasp cracks on masturbation didn't elicit even a courtesy chuckle.

As Silberman made his way to his seat after that laughless set, he was stopped by one of the club's established comics gathered in the back with the other performers.

"I thought he was going to give me some advice, like, 'Hey, you didn't do that bad.' Instead, he was like, 'Your fly was down the whole time,'" Silberman says. "It was just like, 'You suck and you didn't even pull up your pants.'"

It was a brutal introduction to comedy, but it didn't deter Silberman from trying again. In fact, the experience had the opposite effect. The surge of adrenaline had a stronger lasting imprint than the gut-sinking sense of failure. As soon as he finished, he wanted to get back up there.

A month later, Silberman arrived in Portland. He was looking for a more permanent home after living out of a backpack while traveling abroad. It was 2013, a time when all the comedians in town were tripping over themselves to get big laughs and become the next Ian Karmel or Shane Torres, two of the scene's heavy hitters.

"It was a good example of like, oh, this is what good comedy looks like," Silberman says.

Nearly six years later, Silberman has risen into the top tier of Portland comics. The climb has been more of a slog than a saunter. But he can boast co-running several showcases that are well-regarded and highly attended, like the Alliance at Alberta Street Pub, and Comedy Bender, where he also shares emcee duties and manages to pack every booth and barstool at noon on a Saturday in a hole-in-the-wall tavern attached to the Aladdin Theater.

Since Silberman isn't the type to hunker down with a notebook and compose jokes word for word, no two of his acts are ever the same. One night, he may be scratching his beard and wondering, in an exasperated tone, why Portlanders hate white people in dreadlocks but have openly embraced the Nazi haircut—"real short on the side, anti-Semitic up top"—which he'll then attempt to demonstrate by sweeping his wild mane of bushy curls to one side of his forehead. During another set, he may be working out a new bit based on a recent experience, like the time he delayed an orgy of half-cocked old folks by performing standup at a sex club.

Silberman admits his interest in pursuing new ideas rather than polishing a joke to perfection is partially fueled by his ADHD. It has its downsides—he claims he doesn't "have a ton of A-level material" because of his frenetic thinking, which seems to be mirrored by the constant back-and-forth pivoting of his tall, lean frame onstage. But the content always feel fresh and conversational. Silberman also has a penchant for pulling viewers into his act. His large eyes will lock into an intense gaze with anyone in the crowd he chooses to interact with.

"I have a hard time reciting the same thing over. I just get bored pretty easily," Silberman says. "So I go through a lot of material, but also do a lot of crowd work because it gives me something I can be in the moment with and it gives the audience like, 'This is only going to happen for us. He can't do this again.'"

But Silberman's lack of an established script and eagerness to say yes to pretty much every gig can sometimes get him into trouble. "When you're at this level of comedy," he says, "you take any show you can get," even if it's in a dead guy's basement. While he's delivered jokes in some pretty odd places—backyards, streets, speakeasies—that was one of the most bizarre venues in which he's been booked. Turns out, a group of buddies decided to honor their late friend by buying his house complete with a subterranean bar where they all hung out. As a way to keep his spirit alive, the group would occasionally hire comics to perform in the corner while they drank and took bong hits. Though it sounded odd, Silberman was game until he noticed a lack of interest. The material just wasn't registering. So he started to improvise.

"I look around on the wall. There's like all these second- and third-place amateur beer-brewing ribbons," Silberman says. "So I was like, 'Looks like Phil wasn't much of a winner in his life!'"

The room let out an uproarious and offended, "Whoa!"

"What?" Silberman continued. "Can't we roast the dead? It's all in good fun."

"He died last year," someone responded.

Even when a show goes sideways, Silberman embraces the experience.

"People think laughter is great anywhere. It just doesn't work like that," he says. "It's an art form. You need conditions. Like, you wouldn't ask a painter to paint in a fucking hurricane. But I will never turn down a show, because I would rather have it be awful and learn how to be quick on my feet."

Silberman came to comedy at 26, somewhat late compared to most of his peers. During what he calls his "average American upbringing in the Midwest," he was always the funny friend in his group, but never followed standup or immersed himself in comedy. It was during a yearlong trip through Latin America—specifically, one night when Silberman was alone in a hostel on the border of Ecuador and Colombia, doubled-over and dying while watching YouTube clips of Bill Burr—when he decided he wanted to try telling jokes once he got back to the states.

In an effort to get better and put in stage time, Silberman would bicycle to shows around the city, often two or three per night, sometimes seven days a week. At open mics, he'd almost always be the last one up, often performing for a room occupied only by the table busser. But that repetition paid off. It taught him how to fail with grace.

"It keeps you humble, because you bomb all the time," Silberman says. "Even when you start to think, OK I get this, you bomb and re-evaluate."

Silberman still relies on his bike for transportation but is now even busier balancing a regular 9-to-5 job as a writer. That typically means he's home for less than an hour after work before pedaling back out to mic stands scattered across town until 1 am. It's an exhausting schedule, but the rush keeps him hustling.

"If I go more than a couple of days without being onstage, it starts to bother me. I just feel restless," he says. "At this point, I almost need it. It's kind of like a drug."