The Bert Show

Episode: Vault: What Did You Do That You Knew You Should Have Been Fired For?
Date: December 11, 2025
Podcast by Pionaire Podcasting

Episode Overview

In this lively and confessional episode, the Bert Show takes a humorous and unfiltered look at workplace mishaps so risky or outrageous that the participant could—maybe should—have been fired. Listeners call in to share their own near-miss stories, ranging from accidental oversharing to wild company credit card abuse, while the hosts riff on each situation with their trademark banter. The theme is all about those moments we look back on and think, “How did I get away with that?”

Key Discussion Points & Insights

Host Banter: Setting the Tone

• The episode kicks off with the hosts joking about office misconduct, notably referencing a colleague, Crash, and his not-so-subtle office antics.
• Notable Moment: The discussion of “flashing the boss” sets up the open, real, and often irreverent tone the show is famous for.

Listener Stories: Escaping Consequences

Sleeping on the Job as a Lifeguard

[00:55 - 01:23]

• Caller: Jennifer
• Story: Jennifer admits she “used to go to sleep at work at a senior citizen pool” where she was the sole lifeguard.
• Despite repeatedly falling asleep and the employer discovering it, she kept her job.
• Bert (Host): “Oh, you’re kidding…And they found out and they didn’t fire you?”
• Jennifer: “Found out, didn’t fire me.”
• The hosts are stunned but amused, highlighting how some workplaces are more forgiving than others.
• Notable Quote:
  • Jennifer: “Just for a whole entire summer.” [01:13]

Wild Expenses on the Company Credit Card

[01:26 - 02:31]

• Caller: Unnamed male
• Story: With potential clients, he spent $1,500 on lap dances one night at a club and feared he'd be fired when reviewing the receipts.
• The charge went through, and the next day, management only laughed about the incident rather than punishing him.
• Host: “It must have been a good client. You know, you obviously made the client happy.” [01:51]
• Discussion includes digging into how some businesses disguise these expenses on receipts.
• Notable Quote:
  • “Four in the morning, I’m counting up the receipts. I’m like, oh my God, we just spent fifteen hundred dollars.” [01:47]
  • Host joke: “More like Herpes books.” [02:36]

Getting Caught with the Boss’s Daughter

[02:43 - 03:15]

• Caller: Emily
• Story: She was caught fooling around with her boss's daughter in the copy room. The twist: the boss didn't even know his daughter was gay.
• Despite all this, she kept her job. The hosts marvel at the story and question her luck.
• Memorable Moment:
  • “You should’ve saw the look on his face. It was priceless.” — Emily [03:10]
• The panel jokes about office romance and being "caught in the copy closet."
• Notable Host Exchange:
  • Host: “You couldn’t get axed for that, could you?”
  • Emily: “No, I don’t know why.”
  • Host: “Having sex in the office, yeah.” [03:06]

Hot-Mic Mishap on a Conference Call

[03:28 - 04:26]

• Caller: Unnamed female
• Story: During an all-company conference call, she accidentally spoke derogatorily about a client, believing she was on mute, but everyone heard it.
• She describes the chaos as her phone and email “blew up” immediately after.
• The hosts relate, telling their own almost-fired-by-phone stories.
• Notable Quote:
  • Caller: “I click back, forget I’m not on mute and tell a coworker that this is the S-bomb that I got to deal with. The whole company was…” [03:49]
  • Host: “I've done that too—think I'm on hold, say something stupid about the person, and they're still listening.” [04:01]

Notable Quotes & Memorable Moments

• Host: “Crash has done this before. It’s not his first time flashing the boss.” [00:20]
• Jennifer (Caller): “I used to go to sleep at work at a senior citizen pool...Just for a whole entire summer.” [00:56, 01:13]
• Lap Dance Caller: “Four in the morning, I’m counting up the receipts. I’m like, oh my God, we just spent fifteen hundred dollars.” [01:47]
• Emily (Caller): “You should have seen the look on his face. It was priceless.” [03:10]
• Conference Call Caller: “I click back, forget I’m not on mute and tell a coworker that this is the S-bomb that I got to deal with.” [03:49]
• Host: “I've done that too—think I'm on hold, say something stupid about the person, and they're still listening.” [04:01]

The Bert Show’s Signature Tone

• The episode is upbeat, fast-paced, and irreverent—hosts and callers alike share stories with candor and a sense of fun.
• The hosts poke fun, riff on workplace taboos, and connect with callers as peers, leading to some laugh-out-loud moments.
• The conversation is honest and relatable, with plenty of laughs and a sense of “we’ve all been there,” making listeners feel included.

Episode Highlights with Timestamps

• 00:20 — Hosts joke about “Crash” and his repeat HR-worthy antics.
• 00:55-01:23 — Jennifer’s story: Lifeguard sleeping on the job, not fired.
• 01:26-02:31 — Caller admits spending $1,500 at a strip club on company card.
• 02:43-03:15 — Emily gets caught in the copy room with the boss’s daughter.
• 03:28-04:26 — Caller’s hot-mic disaster during a nationwide conference call.

Summary

This episode of The Bert Show is full of jaw-dropping listener confessions and witty host commentary. Centered on one simple but dramatic question—“What did you do that you knew you should’ve been fired for?”—the show delivers stories that are as cringe-worthy as they are hilarious, all wrapped in the show's authentic, teasing, and supportive vibe. If you’ve ever wondered “How did I keep my job after that?”, you’ll feel right at home here.