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Keep Going: How this comedian survived a career in comedy
“When you're going through hell, keep going." This podcast is about failure and how it breeds success. Every week, we talk to remarkable people who have accomplished great things but have also faced failure along the way. By exploring their experiences, we can learn how to build, succeed, and stay humble. The podcast is hosted by author and former TechCrunch and New York Times journalist John Biggs.
He also hosts The Innovators, a podcast focused on brand new startups and C-Level Executives and Creators.
If you’d like to appear on either show, email john@biggs.cc.
Our theme music is by Policy, AKA Mark Buchwald. (https://freemusicarchive.org/music/policy/)
Keep Going: How this comedian survived a career in comedy
I sat down with comedian DC Pearson and what struck me wasn’t the success. It was the patchwork.
From the outside, it looks clean. Comedy group, Sundance film, books, writing for TV. A straight line. But it isn’t.
“Our life is composed of days,” he told me. “And this is one of them.”
That’s the job. Not the career. The day.
Because most of the time, it’s not the dream. It’s the gap between dreams.
DC spent the last year working in social media advertising. Not because he wanted to pivot. Because the work slowed down. Because strikes happened. Because the industry does what it always does, it dries up and then floods again.
“It was challenging to my identity as a creative person,” he said. “But then it was also cool… and I was grateful for it because it’s a job and it allows you to be alive.”
That’s the truth nobody puts in the highlight reel.
You don’t “make it.” You stitch it together.
You jump from one thing to the next. You write jokes for someone else all day, then try to find enough energy at night to write something for yourself. You take the corporate gig, then try not to let it eat the part of you that wanted this life in the first place.
And most of the time, it almost does.
The only thing that saved him was simple. Another person.
Someone else in the same situation. Same background. Same problem.
“We would kind of be accountability partners… I’d say I’m gonna write this thing this weekend… and then I’d come back and say, I did it.”
Not a system. Not a course. Not a master plan.
Just two people refusing to let the work die.
That theme came up again when we talked about how he started. It wasn’t strategy. It was proximity.
Five people. One group. Each doing a different thing well enough to make something real.
“We had… the ability… to go and make sketches that looked better than a lot of stuff that was out there at the time.”
Not because they were perfect. Because they were there.
This is the part people miss now. Especially with AI sitting there, ready to do everything faster.
You can generate the thing. You can fake the output. You can make something that looks right.
But you lose the reason you started.
“I would rather come up with ten dumb toilet puns… that nobody’s ever going to notice… and be like, I did every single one of those.”
It’s the quiet satisfaction that you made the thing yourself, even if no one sees it.
We talked about AI, and he didn’t panic. He didn’t celebrate it either.
He just called it what it is.
“Plausible.”
It looks right. It feels right. It passes at a glance.
But it doesn’t hold up.
And more importantly, it doesn’t carry the weight of a real life behind it.
“A server farm can’t do that,” he said, talking about the weird, difficult experiences people put into their work.
That’s the bet now.
Not that AI disappears. It won’t.
But that the connection between a person and the thing they made still matters.
Even if it gets harder to make money. Even if the pipeline gets worse. Even if everything gets noisier.
Because the alternative is easy.
Too easy.
And easy work rarely means anything.
At the end, I asked him where this is all going. Where media goes. Where attention goes.
He didn’t pretend to know.
But he said something I keep thinking about.
“There are things fomenting that we don’t even know what they are… it’s probably already happening, and the algorithm is not picking up on it.”
That’s where the next thing is.
Not in the feed. Not in the obvious place.
Somewhere small. Somewhere ignored. Somewhere real.
And if you’re paying attention, you’ll find it.
Or better, you’ll build it.
You’re currently a free subscriber to Keep Going - A Guide to Unlocking Success. For the full experience, upgrade your subscription.
If you’ve been reading or listening to Keep Going for free, you’ve already seen the value of having independent work that isn’t shaped by corporate sponsors or the news cycle’s noise. But independence has a cost. If you find something useful here, if these words make you pause or think, I’m asking you to step up. A few dollars each month means I can keep doing this work without compromise. Without your support, this project stays fragile, balanced on the backs of a few.
© 2026 John Biggs
548 Market Street PMB 72296, San Francisco, CA 94104
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