You’ve seen him on Kill Tony. You’ve read his twisted novels. Now hear him go completely off-script. These are the podcasts where Chad Olshavsky shows up loud, laid-back, and unfiltered—talking comedy, writing, relationships, and whatever the hell else comes up.
Whether you’re a book nerd, a podcast junkie, or scouting your next guest—this is where it gets interesting.
This was ChadO’s first time on Kill Tony—and yeah, the nerves were loud. His one-minute set was shaky, but once the interview kicked in, something shifted. He opened up. He got roasted. And then he absolutely landed a joke that caught everyone off guard.
Right after Tony asked how he keeps his marriage spicy, ChadO hit the line that got a big pop:
“One day my wife came to me and said, ‘Hey, we should open our relationship.’ So far, I’ve met no girls… and there’s been a lot of guys coming over.”
Boom. That was the moment.
Dr. Phil (aka Adam Ray) fist-bumped him.
Sam Tallent told him people assume they’re friends.
Even Tony cracked a smile.
The Kill Tony that kicked off the madness. ChadO hits the Kill Tony stage with Sam Tallent and “Dr. Phil,” holding court with gritty stand-up, a side of chaos, and a few memorable mic bumps. Watch Now
In this fan-favorite episode, ChadO gets pulled from the bucket and fires off a tight set about almost dying, raising kids, and trying to figure out if his son’s going through a phase. Kim Congdon and James McCann roast him hard, but Chad shrugs it off with that signature Chicago cool. A funny, weird highlight in a stacked episode. Watch Now
Dating? Sort of. ChadO crashes Hans Kim’s laid-back love talk with unhinged advice and dirtbag charm. This one’s not safe for brunch. Watch Now
What happens when a deranged thriller meets open mic night? ChadO riffs on RoomMate in a casual hang with Tony Cruz that turns unexpectedly deep. Listen Now
ChadO talks shop, comedy war stories, and what it’s like being the new guy in Austin comedy. Watch Now
Cannabis, comedy, and completely off-topic. ChadO shows up lit and ready to vent about life, work, and the thrill (and occasional psychological warfare) of being married for over 20 years. Watch Now
