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"How Could This Bad Email Be Improved? Help!"

Help Wanted

Tue Sep 30 2025

Summary

Podcast Summary: Help Wanted

Episode: “How Could This Bad Email Be Improved? Help!”
Hosts: Jason Feifer (Editor-in-Chief, Entrepreneur Magazine), Nicole Lapin (Money Expert)
Producer: Morgan Lavoy
Date: September 30, 2025

Episode Overview

This episode dives into the art—and frequent failure—of cold email pitches, especially those aimed at media professionals and podcasters. The hosts dissect a real-life “bad email pitch” from their own inbox, analyzing its missteps, discussing what makes a pitch effective, and how it might be improved. The conversation is engaging, practical, and filled with relatable anecdotes and actionable advice for anyone trying to network, pitch, or make their work emails stand out.

Key Topics & Discussion Points

1. Opening Banter: Why Bad Emails Matter

Timestamp: 02:28–03:25

Jason and Nicole introduce their ongoing interest in the topic of “bad emails.”
Email is framed as “the most consequential communication medium of our time” for business (Jason, 04:04).

2. Breaking Down the “Bad Pitch” Email

Timestamp: 04:57–08:32

Morgan shares the pitch she received, which started off poorly by:
- Addressing her as “Nicole” instead of “Morgan.”
- Opening with: “I'll skip the usual bullshit pitch where I pretend I've listened to every episode of your show. We both know those emails are garbage. Lol.”
- Offering almost no detail about the proposed guest (no links, no context, not even a name), despite including a helpful bulleted list of possible topics.
- Attempting to “shock the narrative” awkwardly by being blunt.
The hosts highlight that while some tactics in the email are technically sound—attempting to stand out, summarizing topics for the host—execution is everything.

“It's like the right ideas and the totally wrong execution.”
— Jason Feifer [12:34]

3. What Makes a Good Email Pitch?

Timestamp: 09:13–16:47

Jason discusses Robert Herjavec’s “shock the narrative” sales advice (from Shark Tank), emphasizing the importance of breaking expectations in a genuine way.
Nicole emphasizes the value of specific, authentic references to the show, not generic flattery.

“You don't need to say, like, I've listened to everything you've ever done in the whole wide world... But just something.”
— Morgan Lavoy [15:53]
Both hosts agree:
- Personalization and real research matter.
- Throwing others under the bus is bad form.
- Providing clear, specific value is essential—don’t make the recipient do your work.

4. Other Common Bad Pitch Mistakes

Timestamp: 16:48–18:08

Morgan notes the absence of the show’s name and the lack of any indication the sender knew which podcast (Nicole hosts multiple).
Not providing hard numbers or concrete audience details when promising guest promotion.
The effort required to even learn about the proposed guest is not respected.

5. Critiquing the Follow-Up Email

Timestamp: 18:28–22:52

The sender follows up again, with little real improvement:
- Still addresses Morgan as “Nicole.”
- Claims to have “stumbled upon” the podcast recently.
- Asks where to leave a five-star review, instead of just leaving one.
- Leaves the recipient to dig up the original email.
“If you already found me on Spotify, it doesn’t take much work to just give me the five star review and then tell me you did it.”
— Jason Feifer [21:19]
The “I just stumbled upon” phrasing is called out as a generic, overused, and unconvincing bit of egoboosting.

6. “Stumbled Upon” Bingo – The Worst Cliché in Cold Email

Timestamp: 22:54–25:51

The team checks their inboxes and jokes about just how many pitches contain “I just stumbled upon your podcast/website.”
- They point out it’s lazy, inauthentic, and has become industry spam.
“PSA: All the publicists pitching something out there—please take that phrase out of your email vocabulary.”
— Nicole Lapin [23:15]

7. Advice & “Messing With” Bad Pitchers

Timestamp: 25:59–27:25

The team jokes about how to reply to such emails, and Nicole suggests:
“An honest review on Apple Podcasts would be great. Thanks.”
Morgan agrees to send the reply, expecting even more persistent emails in response.

8. Universal Email Best Practices

Timestamp: 27:25–28:29

Jason’s foundational cold email advice:
- Do your research, know whom you’re contacting, and respect their time.
- Personalize, be authentic, and make a genuine human connection.
Nicole echoes: Always remember the person on the other end is a real human being with limited time and attention.

Notable Quotes & Memorable Moments

On pointing out standard pitch mistakes:

“I don't know why. It’s always Jeff. It's never...I don't know who Jeff is.”
— Jason Feifer [05:19]
On insincere vs. sincere personalization:

“A lot of publicists say they listen to your show all the time. I really did love this episode. I cried at the end with you.”
— Nicole Lapin [13:23]
On overdone clichés:

“Just stumbled upon your website...What is this, The Purpose?”
— Nicole Lapin [24:31]
Email best practice summary:

“You are reaching out to human beings. I don’t care what it is that you’re pitching...the reaction has to be, ‘Oh, wow, this is something I want to learn more about.’”
— Jason Feifer [27:25]

Key Segment Timestamps

02:28–03:25: Why bad emails deserve attention
04:57–08:32: Morgan reads and unpacks the “bad email”
09:13–16:47: Good pitch principles; what’s wrong with “shock” tactics
18:28–22:52: Critiquing the follow-up; “stumbled upon” cynicism
22:54–25:51: Checking inboxes for cliché pitches
25:59–27:25: Joking about replies; crafting “mess with them” responses
27:25–28:29: Final best-practice advice

Episode Takeaways

Personalize with care: Even small, specific references show authenticity and effort.
Don’t throw others under the bus: Negative comparisons weaken your pitch.
Do the recipient’s work: Include necessary context, links, and concrete details.
Avoid spammy clichés: “I just stumbled upon...” is not only ineffective but actively off-putting.
Every cold email is a human interaction: Research, sincerity, and respect go much further than shortcuts and boilerplate.

Tone & Style

The episode is funny, conversational, and a bit irreverent, with the hosts poking fun at bad emailers and industry clichés, but always circling back to practical, empathetic advice for actual professionals.

For more help or to have your question featured, contact: helpwanted@moneynewsnetwork.com

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Transcript

Nicole Lapin (0:00)

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Chime Legal/Disclaimer Voice (2:09)

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Jason Pfeiffer (2:28)

This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, editor in chief of.

Jason Pfeiffer (9:13)

It is. I mean, the funny part about it is that it's doing a couple things that are smart and correct. It's just doing them incorrectly. So I just interviewed Robert Herjavec from Shark Tank and the most memorable thing that he said to me was that the. The greatest sales technique is to. And this was his language shock, the narrative. The idea being that when you go into any kind of pitch, you have to know that the person who you're Pitching has a narrative in their head. And that narrative is basically going to be, this is going to be really boring. I'm going to just sit around and wait for this to end and this person isn't going to have anything interesting to offer me. And so if you go in and then you just do your sales pitch, it will be boring and you will not land it. And so what you need to do is shock that narrative, get them outside of the narrative they already have in their head, so they're willing to pay more attention to you. And there are millions of ways to do that. The story he told me was that a young guy at his cybersecurity company, that's what Robert Herjavec actually does for a living. Outside of being on Shark Tank. As he built the cybersecurity company, there's this young guy who was really studied, knew the products, could not land a sale, just could not do it. So Robert tags along with him and watches him. And basically the guy, like, he's perfectly competent, but he's not making any connection to the person that he's pitching. And so Robert says, next time I want you to try this, I want you to go in there and I want you to sit down and then not say anything for a few seconds and then look the client in the eye and say, before we begin, I. I just have to tell you, I really appreciate you taking this pitch. I am extremely nervous right now because this is my first ever sales pitch. And the reason Robert wanted this young guy to do this is because this guy is mostly pitching to middle aged IT guys. And the middle aged IT guys are going to see this young kid sitting in front of them and they're going to think, that's my son. Like, that's that guy's just like my son. And I want to, I feel bad for him, I want to help him. And that shocks the narrative. It gets people to pay attention, and then you move on and you do the pitch. And this kid started closing and. And I love the idea of shock the narrative. And I now see it in all sorts of different ways. So that is what this person who has emailed you is attempting to do is to shock the narrative. Right? You get, he's basically, he's thinking, you get a million pitches. Let me acknowledge that I am not like those million pitches. So that's a good instinct. The problem is that the way he did it was not just super aggressive, but also just to really reinforce that he has spent absolutely no time getting to know you or the show or whether or not his client is relevant to you. And that, again, negates the next thing that he does where he is trying to do your work for you. If you're pitching, you absolutely should try to do the work for the other person. Never force them to spend the energy in their brain, like doing work to figure out if what you have to offer is actually right for them. You need to make that as clear as possible. But he's telling you, I have no idea if this is relevant to you or not. And like, as a result, it is forcing you to do that work, and that is a big turn off. So it was like, again, it was like the right ideas and the totally wrong execution.

Jason Pfeiffer (19:20)

Yeah, I agree. I, I have a number of problems with it. So first of all, it is still asking you to do work. In this case, it's asking you to track down the previous Email, right? Like, people forget that if, if I missed your first email and then your second email is, hey, did you see my first email? Then I have to go like, try to find your first email that is not useful. That is that I'm not going to go do that. Sometimes people will do this where they'll, they'll, they'll DM me on LinkedIn and they'll be like, hey, did you see that pitch that I emailed you five days ago? And I was like, I, I didn't, but. Or maybe I did and I deleted it. I don't know. But either way, I'm not going to go like, then go back to my email and go searching for it. What is the point? So he's asking, asking to do work. Don't love that. Also, this thing about, I don't know if this translates into other industries, but this shows up so much in media pitches, which is the idea of the stumble upon. I just stumbled upon your podcast. I just happened to find your podcast. Oh, I just glimpsed your pod. Does anybody say that? Like, if I am going and I'm pitching, I've got like a brand new kind of ice cream cone and I'm going into the ice cream shops, is the first thing that I say is like, oh, hey, I just stumbled upon your stupid ice cream shop. And I wondered like, it doesn't, this is not. Doesn't show intention. It doesn't show intention and you need it. Like you are when you are pitching something. I don't care what it is. When you're pitching something, you are a solution provider. You are trying to identify someone with a problem and then provide them a solution. And so even if that's pitching pr so that if you're, if, if this guy is pitching Nicole slash Morgan, then what he is really trying to do here is identify the problem that you guys have, which is, hey, we're producing podcasts. We need to deliver great value for our listeners. Delivering great value for our listeners grows our audience and therefore the business. And you know, that is resource intensive. And so if you have a solution for that in the form of a great guest that has been vetted and you know is going to be then like, that's solving a problem. But that does not come across at all. If it's like, hey, I just stumbled upon your crap, right? Like that, that says that you haven't spent any time understanding my problems. So I don't like that at all. The one thing that's like sort of okay, is the offer of the Five star review. But I would say, you know what, if you already found me on Spotify, it doesn't take much work to just give me the five star review and then tell me that you did it. Instead you've stumbled on me on Spotify and now you're going to send me an email to be like, hey, is this the best place to like, yeah, more work? How about. Yeah, more work. How about you just tap the button and then tell me you did it? That's kind of nice.