From ages four to twenty-two, Ben Gleib had a stutter and a vocal disfluency so severe that his chords would lock down mid-sentence. He'd sit in class dreading being called on to read aloud, convinced it was a kind of execution. And he wanted, more than anything, to be a comedian and a TV host.
He became one.
Twenty-five years of standup later, Ben has performed to arenas, hosted an Emmy-nominated game show (Idiotest, 210 episodes across Netflix and Game Show Network), appeared on Chelsea Lately, starred in a Showtime special now on Amazon, and is building the internet's first late night talk show (Goodnight with Ben Gleib) backed by Nikki Glaser and Scott Galloway. He also coaches executives on their TED Talks and wedding speeches. And yes, those are the same skill set.
Pia first saw Ben perform at a comedy club in Austin. Pia was front row, not by choice, watching him navigate a guy in a cowboy hat who wouldn't sit down and kept trying to make himself the show. Ben didn't flinch. He made the cowboy the funniest part of the night.
Watching it happen, Pia realized this is exactly what crisis communications looks like.
This episode is a masterclass in owning a room, staying composed under real pressure, and saying things that actually land. It applies whether you're in a comedy club, a boardroom, a media interview, or an all-hands meeting where your whole team is watching to see how you show up.
In this episode:
- Why comedians have become the last honest voices in public life and how truth is baked into every real laugh
- Crowd work as a communications framework: how Ben reads a room, finds the right people, and knows exactly how far to push
- The math that proves speaking to a thousand people is less risky than speaking to one
- What a childhood stutter that lasted eighteen years taught Ben about public speaking anxiety
- Why silence is the single most underused communication tool in business
- The coaching techniques Ben uses with executives on TED Talks and high-stakes presentations
- How building a late night show from his house on YouTube became the perfect format for an attention economy that rewards real over polished
- The idea-capture habit he shared with Chris Rock and has used for twenty-five years
- Why the moments that go most wrong are often the ones that build the most trust
If you’re an exec or founder looking to level up your communications skills, this episode is for you.
Ben Gleib is launching his new weekly late night show ‘Good Night With Ben Gleib’ on YouTube on Thursday May 28 and every Thursday at 10 pm EST / 7 pm PST. People can join his interactive worldwide virtual audience the night before and every Wednesday by getting a ticket at makeitagoodnight.com. You can follow along on his socials on all platforms @makeitagoodnight.
And make sure you subscribe to Well Said on all platforms to get new episodes every Wednesday.
TIMESTAMPS
02:12 — Front row in Austin, cliffhanger compliments, and comedians vs. politicians
05:00 — What is crowd work and why it's a masterclass in real-time communication
07:45 — "Stay in the pocket"
10:00 — The math of crowds
13:30 — Self-deprecation + admitting mistakes
17:30 — A childhood stutter
20:00 — The power of silence
24:00 — Coaching executives: timing, motion to stillness, and how to make a moment land
29:40 — "Goodnight with Ben Gleib"
39:30 — When things go wrong: the DJ, the muted audience, and Scott Galloway's mic
