Vault: Jeff Made A Big Mistake On his Voicemail

Summary

The Bert Show: Vault – Jeff Made a Big Mistake on His Voicemail

Episode Date: January 19, 2026
Cast: Bert, Jeff Dollar, Melissa, Jen
Theme: The hilarious chaos and pressure of recording the perfect outgoing voicemail message, especially in the context of vacation notices under a complicated phone system.

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Episode Overview

This episode dives into the all-too-familiar struggle of recording voicemail greetings, spotlighting Jeff Dollar’s recent blunder: accidentally leaving a garbled, outdated, and unintentionally public—sometimes even profane—voicemail greeting that played for two weeks. The cast shares their own mishaps, highlighting the relatable truth that voicemail systems are often more complicated and pressure-inducing than they seem.

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Key Discussion Points & Insights

1. The Struggle Is Real: Complicated Voicemail Systems

• The show opens with Bert and Melissa joking about how no one gets their voicemail recording right on the first try:
  • “It's never right the first time.” – Melissa [00:23]
  • “It's never right like the first 15.” – Bert [00:26]
• Jeff explains the step-by-step anxiety and button-pressing confusion that leads to mistakes, especially when under pressure to sound professional and provide accurate information.
• The group agrees that their station’s system is far from intuitive, increasing the likelihood of mistakes.

2. Jeff’s “Blooper Reel” Voicemail

• Jeff set out to record a simple vacation message—including an emergency contact (Tracy) for urgent matters—but kept flubbing the details and button sequence.
• The end result was a series of partial, unfinished, and occasionally expletive-laden messages that were actually broadcast as his voicemail greeting for two whole weeks:
  • “If I made a mistake...you push the button that starts over, and after you've had to start over a few times, you think you have the sequence of buttons memorized...But if you screw them up and somebody calls you, this is the outgoing message they hear.” – Jeff Dollar [01:53]
• Jen dramatically recreates the garbled collection of mixed-up messages, which included multiple versions, half-numbers, and even Jeff catching himself nearly distributing a private cell phone number over the air:
  • “...but probably not at that number because that's her cell phone number and she probably wouldn't appreciate me giving that out.” – Jen (as Jeff) [02:21]
• Bert confirms for listeners: every time someone called Jeff, they got some or all of this “blooper reel”—with the curse words bleeped out for the podcast.

3. The Pressure of the Perfect Voicemail

• Jeff and Bert discuss why it feels so important to get it right, despite evidence that most people won’t listen carefully or care:
  • “There is a lot of pressure in the outgoing greeting, the what you hear when you call.” – Jeff Dollar [04:40]
  • “So if I get through the whole thing and I get the details right, I won't listen again because I'll think you'll hear something wrong. It sounds stupid, I gotta do it again.” – Bert [04:48]
• The group agrees that, even among radio professionals, voicemails quickly go from a place of high effort to resigned acceptance, with Bert noting that Jeff's result was “basically a blooper reel.” [05:01]

4. Classic Voicemail Fails

• Melissa shares her own tale—a voicemail recorded while sick, never re-recorded, so she always sounds congested to callers.
• Jeff recalls his grandmother’s answering machine capturing a totally unrelated, candid message about church plans, highlighting analog-era fails.
  • “You would call her answering machine and you would hear a message that my aunt had left for her...‘We're going to church at 3:30. If you want to walk over with us. We're going with Margaret and Harold...’” – Jeff Dollar [05:18]
• Bert rounds out the segment by recounting his mom’s stilted, always-the-same greeting, with the classic awkwardness at the beep.

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Notable Quotes & Memorable Moments

• On voicemail anxiety:
  “I hate cutting those things, man.” – Bert [00:38]
• On the accidental “blooper reel” greeting:
  “So all of them, all five messages were the outgoing message for the last two hours.” – Bert [03:58] “Except the f word and the s word were in there, too.” – Jeff Dollar [04:04]
• Classic radio producer humor, after Jeff nearly gives out a cell number:
  “And Tracy just passed out. Cause you gave her number out.” – Melissa [01:44]

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Timestamps for Important Segments

• 00:01–00:40 – The group laments how hard voicemail messages are to record.
• 00:41–02:21 – Jeff details his attempt at the perfect vacation message, including a recreation of the ideal script.
• 02:21–03:58 – Jen performs the actual “blooper reel” voicemail as callers heard it, packed with confusion, corrections, and near-mistakes.
• 04:00–05:18 – The cast unpacks why voicemail is so fraught, and why perfection is impossible (and unnecessary).
• 05:18–06:11 – Personal family anecdotes about how voicemail fails are universal, not just in radio.

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Summary

The episode is an engaging, laughter-filled reflection on the universal perils of voicemail greetings, made extra relatable by the real blunders of seasoned broadcasters. Listeners learn that even the professionals can’t master the outgoing message on the first (or 15th) try—and that, in the end, a little imperfection is both expected and hilarious.

Transcript

[Jeff Dollar]

The Birch Show.

[Bert]

Jeff made a very common mistake that I think many of us around here have made on our outgoing voicemail messages, because we have a complicated system here. You think it's like, it should be so easy. You hit five, you leave your outgoing message, you hit three, or you hit star, and it's over. Right? Right. And obviously, when all of us go on vacation, we try to leave a message that says, hey, we're not gonna be around until September, blah, blah, blah.

[Melissa]

It's never right the first time.

[Bert]

It's never right the first time.

[Melissa]

You gotta do it over and over again.

[Bert]

It's never right like the first 15.

[Jeff Dollar]

Times, which is why Bert's just given up. And if you call Bert now, it says, hey, hey, listen, I'm just heading out on vacation, but I will be back on June 7, 2002. I hate cutting those things, man.

[Bert]

I really, really do.

[Jeff Dollar]

For this reason, I was leaving my message, my outgoing message before I went on vacation, and I was saying, hey, I'm gonna be gone until September 12th. And it sounds simple enough, right? But there could be urgent show stuff going on. Cause obviously, Jen and Melissa were here for the first part of the vacation, and Burt was back. So there could be important show stuff happening and maybe an interview possibility or somebody who is one of my contacts would have get a hold of somebody else. So what I wanted to do was leave Tracy's information, too, so they could contact Tracy. It seems simple enough, right? So ideally, you would call my voicemail and it would say, hey, this is. It's gonna be a miracle if I can do it. But, hey, actually, it's gonna happen now because there's no pressure, right? Hey, it's Jeff. Hey, it's Jeff Dollar with the bird show at Q100. I can't take your call right now because I am on vacation, but now. And I'll be out of the office until September 12th. But if you have an urgent show matter, please call TracyPaluso at 404-497-4837, or email her traceyalthehitsq100.com Otherwise, I'll respond to your phone message or your email when I return on the 12th. Thank you. Have a good day.

[Bert]

Beep.

[Melissa]

Done. And Tracy just passed out. Cause you gave her number out.

[Jeff Dollar]

So that's like the direct. That's it, right?

[Bert]

Yeah, Done. Cut. One. Cut.

[Jeff Dollar]

But if I made a mistake, let's say I said, hey, this is Jeff. I'll be adding till September 15th. Oh, no, I'm out till 12th. Okay, start over. So you push the button that starts over, and after you've had to start over a few times, you think you have the sequence of buttons memorized that you have to push to do the start over. But if you screw them up and somebody calls you, this is the outgoing message they hear.

[Bert]

Now, this was on your outgoing voicemail message for how long?

[Jeff Dollar]

Two weeks.

[Bert]

Two weeks. When people called Jeff's voicemail, they got this.

[Jen]

Hey, it's Jeff Dollar with the Birch show and all the Hits Q100. I'm out of the office till Monday, September 12th, and if you have an urgent show matter, you should contact Tracy Pa Peluso, the producer, at 40471, but probably not at that number because that's her cell phone number and she probably wouldn't appreciate me giving that up. Hi, this is Jeff thaler with the bird show at all the hits Q100 and I am on vacation until Monday, September 12th. If you have an urgent show matter, email tracypaluso R a c e y the hits q100.com or call her at 404SVA. We should invest one me. Hi, this is Jeff dalloway, the bird show at all the hits Q100. Amy, I am not available to take your call because I'm on vacation until Monday the 12th. If you have an urgent show matter, you can reach Tracy Peluso at T R A C E Y at allthehitsq100.com. Hey, it's Jeff. No. Hi, it's Jeff Dollar with the Birch show at all the Hits Q100. And I am not available to take your call because I'm on vacation till Monday, September 12. If you would like to contact producer.

[Jeff Dollar]

Oh, my God. Hi, this is Jeff and I am.

[Jen]

On vacation till Monday, September 12th. If you have an urgent show matter, contact producer [e-mail] or call her at 404497. Otherwise, leave me an email and I'll respond to you when I return to the Office next Monday, September 12th. Thank you for calling. Bye.

[Bert]

That whole thing. So all of them, all five messages were the outgoing message for the last two hours.

[Jeff Dollar]

Except the f word and the s word were in there, too.

[Bert]

And so the beeps that you heard were Jeff cursing.

[Melissa]

Oh, my God.

[Bert]

It shouldn't be that complicated. Like you go into our voicemail system in that voice tree, the first person greeting the second person greeting the.

[Jeff Dollar]

But the problem is how many voicemails.

[Bert]

Greetings if you're on the other line.

[Jeff Dollar]

Greeting and how many Voicemails, do you have number one. Like, you gotta know how to get into your cell phone, how to get into your home phone, how to get into your work. On top of that, like, for whatever reason, there's a lot of pressure in the outgoing message.

[Melissa]

You know what I mean?

[Jeff Dollar]

There is a lot of pressure in the outgoing, you know, the greeting, the what you hear when you call. So, like, normally I'll record it a couple of times.

[Bert]

Yeah. And so if I get through the whole thing and I get the details right, I won't listen again because I'll.

[Jeff Dollar]

Think you'll hear something wrong.

[Bert]

It sounds stupid. I gotta do it again. Seven or eight cuts. Mine. Yours is basically a blooper reel.

[Jeff Dollar]

Right?

[Bert]

People got a blooper voicemail message when they listen to you.

[Melissa]

Classic my voicemail message here at the station. And I don't know when I missed a comma voicemail to remind me of something. And I still have a cold from six months ago. Like, I still am congested on my voicemail message because I didn't want to recut it because I'm the same way.

[Jeff Dollar]

I don't know how it happened, but somehow at one point in the past, years ago, my grandmother was alive. You would call her answering machine and you would hear a message that my aunt had left for her. And I have no idea how they screwed up what the conversation is, but you would call it ring, ring. And then you click. We're going to church at 3:30. If you want to walk over with us. We're going with Margaret and Harold. So call me downstairs if you want to go at 3:30. We'll pick you up at 3. Then we'll go to the cemetery and get flowers.

[Bert]

Yeah, my mom's is always the same way. It's the same every time she tries to cut, it's like, hi, you've called Myra Weiss. Go ahead. Leave a message at the beep. I'm not available right now. Thank you. And then you hear.

[Jeff Dollar]

Beep, the Birch Show.