Entrepreneur School

If you’ve ever pitched yourself to be on a podcast and gotten total crickets… this one’s for you.

I’m spilling the tea on podcast pitches—the good, the bad, and the so-bad-I-hit-delete-before-I-finish-reading. As someone who has a background in public relations and has hosted this show for over two years, I get dozens of pitches every week. And honestly? Most of them are awful.

So I created this episode to help you do better.

I’m breaking down the 9 red flags that make me delete a pitch instantly. These are the things I see over and over again from cold pitches, especially the kind written by AI or PR agencies that clearly don’t know me, my show, or my audience. But don’t worry—I’m also sharing the exact steps to write a thoughtful, strategic pitch that actually gets a YES.

In this episode, I share:

  • Why cold pitching rarely works (and what to do instead)
  • The most cringe AI-generated language that screams “template”
  • What I actually want to see in a guest pitch
  • Why doing your research gives you a major edge
  • The power of leading with generosity and relationships

This is the no-BS guide to getting visible through podcast guesting—without being annoying, lazy, or robotic.

>>Your Next Steps:

🔹 Grab the 90-Day Visibility Sprint Starter Kit — your mini system to stay visible all summer long (with an AI assistant built in!)

Want support building your visibility strategy?

🔹 Get Valerie the Visibility Auditor, your strategy sidekick!

🔹 Book a call to talk about working together

🔹 Follow on Instagram (just not this summer!)

>>Thanks for Listening!

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Transcript
Unknown:

Visibility grows through trust, not cold

Unknown:

outreach, right? Because the best pitches, they feel like a

Unknown:

continuation of an existing relationship. That's to me,

Unknown:

that's what creates the best episodes.

Kelly Sinclair:

This is the entrepreneur school podcast

Kelly Sinclair:

where we believe you can run a thriving business and still make

Kelly Sinclair:

your family a priority. This show is all about supporting

Kelly Sinclair:

you, the emerging or early stage Entrepreneur on your journey

Kelly Sinclair:

from solopreneur to CEO while wearing all of the other hats in

Kelly Sinclair:

your life. My name is Kelly Sinclair, and I'm a brand and

Kelly Sinclair:

marketing strategist who started a business with two kids under

Kelly Sinclair:

three. I'm a corporate PR girl turned entrepreneur after I

Kelly Sinclair:

learned the hard way that life is too short to waste doing

Kelly Sinclair:

things that burn you out on this show, you'll hear inspiring

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stories from other business owners on their journey and

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learn strategies to help you grow a profitable business while

Kelly Sinclair:

making it all fit into the life that you want. Welcome to

Kelly Sinclair:

entrepreneur School.

Kelly Sinclair:

Hello, hello and welcome back to another round of the summer

Kelly Sinclair:

strategy snack series. This is your quick hit guide to staying

Kelly Sinclair:

visible in your business without creating content or relying on

Kelly Sinclair:

social media. In case you didn't know, I'm taking the entire

Kelly Sinclair:

summer off of social OMG. I'm writing about it in my email

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diaries. So make sure that you are on my email list and

Kelly Sinclair:

following along to this series, because every episode dives into

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one visibility strategy that you can start implementing now. And

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I've also created a free resource to help you build your

Kelly Sinclair:

visibility habit over the summer. It's called the 90 day

Kelly Sinclair:

visibility sprint starter kit, and you can find the link to

Kelly Sinclair:

grab these actual tools that I use for planning and tracking

Kelly Sinclair:

visibility in the show notes. Okay, so I feel like I have been

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saving up to record this episode for months. Today, we are

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talking about podcast pitches, The Good, the Bad and the Ugly.

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I get pitched by dozens of people every single week, and

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honestly, most of these pitches are really bad, so sorry, but

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not sorry. Today I'm pulling back the curtain on what makes

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me instantly delete a pitch, the reasons I say no, and what

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actually makes a pitch stand out, which are few and far

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between. But you are going to learn all of the secret sauce to

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making that happen if you've ever pitched to be on a podcast,

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or you're planning to this episode, could seriously shift

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your strategy. So I want to start with like, the real

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problem of podcast pitches, and this is coming from. One, I've

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been a podcast host now for over two years. And two, my

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background is public relations. So one of the things that we do

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a lot in PR is media pitching. So pitching to get clients on

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media, different media channels, so, TV, radio, newspaper, online

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articles, you name it, I have pitched all of these things, and

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the core philosophy behind this is media relations, aka which

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now includes podcast outreach is a boat demonstrating value. You

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have to think about the value that this can bring to a podcast

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listener. So the host job is to provide value to their

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listeners. Your job, if you're pitching, is to show them how

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you're going to help them to do that. And I have to say, I'm

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going to take a stance here. Whole pitching rarely works.

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Most of my guests, 99% of my guests, are people that I know

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personally or were referred by a collaborative partner, and I

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have never personally cold pitched to be on a podcast

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myself. This is not an approach that I take as part of my

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visibility. And I have been on probably over 50 podcasts at

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this point, maybe more, I don't know, and that's because you

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have to think about this podcasting, created podcast is a

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very time intensive process. It requires planning, recording,

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editing and promoting, and if you haven't seriously,

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extensively listened to a show, I do not recommend that you

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pitch to be on that show, because there are going to be so

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many nuances and elements that you're missing that just

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demonstrate that you're not an avid listener. And. And that's

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something that we want to know as podcast hosts, that you

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really understand what we are all about and who we are really

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for, so that you can make that easy connection of why what you

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want to talk about is going to be valuable to our audience. So

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if you're pitching, you can just shift your mindset from how do I

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get featured, to how do I make this a valuable conversation for

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the host and their audience, and focus on that that's the number

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one thing to bring in to a pitch. And again, that pitch can

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be to somebody that you've met that makes it way easier, like

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100 times easier. So there's my like, fast hot take off the top

Kelly Sinclair:isode, but I do have for you,:Kelly Sinclair:

to not do in your podcast. Pitch when you're reaching out. So

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again, if you're already moving away from cold pitching to

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pitching people who you have a relationship with, that's

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already going to take you so much farther. But here's what I

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don't like when I see things that I don't like.

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Number one is fake personalization. I get a generic

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loved your most recent episode. It has no detail, no proof that

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they've actually listened to it. All they have done is gone into

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my history and, you know, dropped to the title of recent

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episode or conversation like that I did, like, last week, one

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time I got an email from a podcast, like, from a pitch that

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was an episode that had been released like, 12 minutes ago.

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Like they couldn't have even possibly listened to the episode

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because it just went live, and I got the email so early in the

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morning, it was like, how, how did you even get this in here?

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So it's just so obviously fake personalization. It's like lazy

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flattery, and that's a big red flag.

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Number two is the obviously AI generated language. Okay, I have

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to actually read you some podcast pitches that I have

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received to talk about what not to do here, and I will remove

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names for the sake of privacy and, you know, embarrassment. So

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first of all, there are some AI phrases that just completely

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make me cringe. Like this episode really hit home, or it

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resonated with me, or quote was a refreshing perspective. Or,

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here's my favorite one, it struck a chord. Who says it

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struck a chord? Nobody says that, don't write that. Don't be

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a robot. Okay, so for example, here are a couple of literal

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quotes that I'm taking from that just it's just like a repeated,

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like templated, obvious pitch quote. Listening to your recent

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episodes has been a highlight for me. I particularly

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appreciated the latest in the vanity metrics detox series,

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which is a series that I did and how you talked about

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opportunities hiding in the momentum of past achievements,

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it reminded me of guest pitch name whose approach aligns

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seamlessly with that idea. I think guest would make a

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fantastic guest for your show. Great next one. Your latest

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episode on performative visibility really struck a chord

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with me. Well, there it is. The idea of spending so much time on

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quote, looking visible rather than generating real business

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results was an eye opener. The mantra for detoxing busy work is

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something I've already pinned to my wall, and then they go into

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pitching the guest? Yeah, I just can't like it's just so

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obviously fake, and I'm not into it. I'm a relationship person,

Kelly Sinclair:

so that's not happening for me. All right, try not to make this

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too much of a ranting episode, but that's where we're going. I

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guess

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Number three red flags are the can I pitch you messages? Okay,

Kelly Sinclair:

so I appreciate that you're trying to keep things simple by

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like having a short email that says, you know, are you the

Kelly Sinclair:

right person? Is this your process? I want to make sure

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that I'm following but probably you could have found that out

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online, on the website, if there's a section on a regarding

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podcast guests and how to how to apply. But I really feel like

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this is adding a step right. And if you are being a respectful

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person who understands that a podcast host gets dozens of

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pitches, plus all of the follow up pitches, like a lot of them

Kelly Sinclair:

are doing, like three to five follow ups within two weeks, and

Kelly Sinclair:

I just haven't gotten to that yet. So what you're doing by

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adding a Can I pitch you email is just really clogging up my

Kelly Sinclair:

inbox and adding a step, just go ahead and pitch, pitch right off

Kelly Sinclair:

the bat and and you could add at the end if you wanted. You know.

Kelly Sinclair:

So if this isn't where you like pitches, please let me know. I

Kelly Sinclair:

would happily, you know, fill out your form or do whatever

Kelly Sinclair:

else if you want to make a point of, like, just showing that

Kelly Sinclair:

you're ready to be flexible and do whatever the host is looking

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for. But I'm not gonna respond. I recently just got like, two to

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three emails from the same person asking if they could

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pitch before like so they still haven't pitched me. They've just

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sent me multiple emails about whether or not they could apply

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to be a podcast guest, and that's just taking up time that

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I don't have.

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Okay, Red flag number four, pitching just your story. So

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personal journey without a clear takeaway, that is not going to

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land for most podcasts unless the podcast is very much just

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about stories. But I don't think that there's that many that are,

Kelly Sinclair:

you know, doing it that way anymore. You need to know that.

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You need to know what the takeaways are, what the

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actionable insights that the audience is going to get out of

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it, not just like Cool story, that's what we're sharing today.

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So I just skip over those ones that that don't have a clear

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takeaway.

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Number five on my red flags list is boastful BIOS with no topic.

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So I get a lot of pitches, and usually these are from PR firms,

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or people who are pitching on behalf of somebody else, not

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somebody themselves, generally, that's just like a really long

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this is how much money this person has earned, or how many

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companies they've built and sold, or they've they're

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featured in Forbes cool. But what is your angle? Like? If I

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have to ask a question about what would this conversation if

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I can't clearly see what this conversation would be like on my

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show, I'm skipping over this pitch,

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which takes me to number six, which is irrelevant topics you

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need to do research. Okay, okay, I'm sorry. I feel like I sound

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like a jerk. I am mostly irritated by pitches that come

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from PR firms. And I will circle back to why at the end, this is

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just like, I think it's bad practice. You should know

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better, because you have training in this area. And I can

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say that because I do not to do these things. So this is who I'm

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talking to, primarily, and you get to learn from my like rant

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against them, on how to adapt this for your own personal

Kelly Sinclair:

podcast guesting journey. So irrelevant topics, you need to

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know what the podcast is about. Don't pitch things that have

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nothing to do with the show. Like my show has a very general

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name. It's called entrepreneur school, which makes people think

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that they can talk about anything related to making money

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at all. But I don't talk about real estate, I don't talk about

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cryptocurrency, I don't talk about investments like there's a

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lot of things I don't talk about on this show, in fact, and if

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you actually listened and did research, you would know that.

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So don't pitch irrelevant topics to a show. Make sure that it's

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very aligned or it's not going to go anywhere.

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Which takes me to number seven, which is clearly no show

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research, no reference of past episodes, how they align, no

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awareness of what has and hasn't been discussed, because that's

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the other thing is, if something has been like recently published

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on my show, I'm not going to do it again, right? Like I have

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talked to, you know, finance people, accountants, mindset

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people on the show, but I don't put those episodes out close

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together. I like to space it out so that we have a variety of

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topics and guests and things like that happening. And so

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would most podcasts. So make sure that you have done the show

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research

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Number eight, trying to match past guests. So I see a lot of

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like, my client is like your last guest, and what I really

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want is how you're different, right? I'm looking for fresh

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voices, not more of the same. So don't say that. You know, we are

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aligned, and I can talk about the same thing. I don't want to

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talk about the same thing. I want to talk about different

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things. So talk about where there's a gap and where there's

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something that you can fill in and bring a different

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perspective on and

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number nine is mass pitches from PR agencies. Okay? Zero

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personalization here. No clarity. I think the problem

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really is that you know, and speaking to somebody who worked

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in media, and I know what clients want, I know that the

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result they want is placements, right placements, meaning they

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get featured in the media. But we cannot guarantee that as PR

Kelly Sinclair:

people, and we can also not guarantee how many podcasts we

Kelly Sinclair:

can get you on. Hmm, which means the only thing that they can

Kelly Sinclair:

guarantee is how many podcasts they pitch for you, and then, as

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a result, there's probably, like, a percentage that they'll

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likely get. But I think that's the issue, is that PR agencies

Kelly Sinclair:

are promising quantity, and that is really sacrificing quality of

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alignment. And I think I have accepted maybe one guest pitch

Kelly Sinclair:

about from a podcast in the past, and it was very early on

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before I had more established relationships for podcast

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guests, so I don't think I would maybe even ever accept a PR one

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again. And that's not just because it's coming from a PR

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firm, but it's just so clear that this I feel bad for people

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who are paying somebody to pitch for them and they're getting

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this kind of result like this is what's happening on the back

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end. So if you're currently in that place, and you've hired

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somebody to pitch for you and you're not seeing good results,

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I would go and ask them to share the pitches and make sure that

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they're not setting off any of these red flags that I've shared

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in this episode.

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So let's turn this around and make it a little more positive

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and action oriented for you into what makes a pitch stand out,

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and the first one is genuine listener engagement, like if

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some of the cold pitches that I have received, that I've

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actually accepted onto my show have mentioned a specific

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episode, have screenshotted a review that they left, I thought

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that was An extra great step to take somebody who's actually

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listening like, and I know that they're listening because of the

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way that they reference my show, episodes that weren't just like

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the one that came out yesterday, but ones that came out, you

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know, months ago, or they've really, like, dug into the

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archive, or they really get the theme, and it just is so clear

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In the pitch.

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The second thing I love about pitches that stand out are

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relationship based approach. So do you have a connection to

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somebody who's been on a show that you can like, speak to, oh,

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I saw you had my friend. Insert person's name here on your show.

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You know, here's our relationship. Or I tend to also

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speak to that kind of audience, but this is my different

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perspective. Like I love that. I love a good, honest and

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authentic name drop that helps.

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The third one is show understanding. So please do tell

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me where you see a gap or a unique angle that hasn't been

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covered. That's what I'm looking for. I recently just got a

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pitch, actually, that I will reply to that said, I haven't

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seen you talk about this on the show before. And I was like,

Kelly Sinclair:

You're right. I haven't talked about that. I am interested to

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hear more about what you have to say about that. So that's a

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really great way to to show how you are engaged, aware and know,

Kelly Sinclair:

know the topic and the audience of the podcast.

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And as I was saying from the outset here, another pro tip is

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audience first framing. So tell me what my audience will gain

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from hearing you. My job as a podcaster is to provide value to

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my audience, and you have to think about how you can help me

Kelly Sinclair:

to do my job. That's the same when it comes to media. That's

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the way that we get media coverage. Is I know who your

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audience is, what they want to know, and here is how we can

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talk about that. So it's about the audience. It's always about

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the audience.

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And the last one I want to share on the pro tips that make your

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pitch stand out are keeping it clean, like, don't give me six

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different paragraphs of topics that you could cover. Pick one

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to two, I like it's okay to have options. I think that's a good

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thing, but I don't want to read a really long, heavy worded

Kelly Sinclair:

email. So things that have, like, really clear bullet points

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in them, of talking points, and then maybe you attach a one

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sheet with your bio, with links to previous things in it. That's

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kind of, again, the same approach that I use for media

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pitching, which is what we call a pitch note, which highlights

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the key points, but then there's more information available if

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the journalists that you're pitching is interested, and that

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keeps the inbox clean. It just keeps it easier to read and

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review. Because I tell you, like, I'm going to be honest,

Kelly Sinclair:

I've been struggling to set up the proper system to manage all

Kelly Sinclair:

of these pitches, and so as a result, what happens is I don't.

Kelly Sinclair:

I just ignore them all. That's why I only have had guests who I

Kelly Sinclair:

know, who I'm having conversations with, directly in

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other ways, who I'm doing podcast swaps with, whose shows

Kelly Sinclair:

I'm also being featured on. And part of that is that, you know,

Kelly Sinclair:

I just get there's just too many there's too many emails, and

Kelly Sinclair:

there's too many follow ups. And sometimes, like these ones that

Kelly Sinclair:

come from PR agencies, they're sending me multiple pitches for

Kelly Sinclair:

different clients with the same template and the same timeline,

Kelly Sinclair:

like I have, I think, two or three, because I, I was just

Kelly Sinclair:

looking back, for the sake of this episode, I wanted to, like,

Kelly Sinclair:

get some real kind of data and review the podcast pitches that

Kelly Sinclair:

I get, just to make sure it wasn't me just being, you know,

Kelly Sinclair:

too lazy to read them or something, but I have one person

Kelly Sinclair:

who sent me like, it's the same subject line, but as the

Kelly Sinclair:

different guest name was, like, terrific guest recommendation,

Kelly Sinclair:

colon, And I don't mind that, like it's obviously a pitch in

Kelly Sinclair:

the in the subject line, that actually makes it easier for me

Kelly Sinclair:

to organize things, but I end up having all of these podcasts,

Kelly Sinclair:

pitches, too many to review, too long, too many follow ups before

Kelly Sinclair:

I have chance to even get back to them, and it just becomes a

Kelly Sinclair:

big mess in my inbox, and it's overwhelming, and so I just

Kelly Sinclair:

don't deal with it. So that's what happens. And so therefore,

Kelly Sinclair:

you know, think about that too. If you've done cold pitching

Kelly Sinclair:

before, that might be the case. The get the host may just be

Kelly Sinclair:

like, completely overwhelmed with pitches, and that doesn't

Kelly Sinclair:

mean that your pitch was bad, but maybe there's a different

Kelly Sinclair:

way to reach out and connect with them, to start that

Kelly Sinclair:

relationship, because that's the bigger theme that I want to

Kelly Sinclair:

leave you with here, is that it is about relationships, so

Kelly Sinclair:

visibility grows through trust, not cold outreach. I think it's

Kelly Sinclair:

just a reframe on podcast.

Kelly Sinclair:

Pitching can be about building a relationship with somebody who

Kelly Sinclair:

has a podcast, instead of doing podcast research and sending

Kelly Sinclair:

three cold pitches a week. If that's kind of how you hide your

Kelly Sinclair:

mindset, maybe you could flip that right, because the best

Kelly Sinclair:

pitches, they feel like a continuation of an existing

Kelly Sinclair:

relationship. That's to me, that's what creates the best

Kelly Sinclair:

episodes, the people that I have on here, that I have, like

Kelly Sinclair:

previously talked to, the conversations are so much

Kelly Sinclair:

better. The ones that I have accepted from cold pitches are

Kelly Sinclair:

maybe somebody who I thought, you know, could fill in a gap

Kelly Sinclair:

that I hadn't talked about before, but that conversation

Kelly Sinclair:

was much more, you know, transactional, and it's obvious

Kelly Sinclair:

if you've listened to the show you can you can probably pick

Kelly Sinclair:

those out. Feel free to send me an email with your suspicions if

Kelly Sinclair:

you want to chat through this episode afterwards. But in the

Kelly Sinclair:

end, this is all about being visible and being generous, and

Kelly Sinclair:

then opportunities will start to come to you. So it's entirely

Kelly Sinclair:

possible to be podcast pitching in under 10 minutes because it's

Kelly Sinclair:

more of a like, Hey, I just need to drop a voice note to this

Kelly Sinclair:

other person. Like, latest podcast I just booked for myself

Kelly Sinclair:

came from a Voxer conversation. It was somebody that I met an

Kelly Sinclair:

event A few months ago. So there you go.

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So here's your takeaway, most podcast pitches fail because

Kelly Sinclair:

they're too self focused, too generic or just plain lazy, but

Kelly Sinclair:

you you're going to do better. Your pitch will be thoughtful,

Kelly Sinclair:

strategic and generous, and that makes all the difference. And if

Kelly Sinclair:

you're loving these snack sized visibility strategies, remember

Kelly Sinclair:

to grab the 90 day visibility sprint starter kit. It's your

Kelly Sinclair:

key to building your visibility habit with low lift strategies

Kelly Sinclair:

that you can implement in under 10 minutes a day, and the link

Kelly Sinclair:

is in the show notes. Now next week is a total treat. I am

Kelly Sinclair:o grew her email list by over:Kelly Sinclair:

subscribers in under six months without a huge audience or an ad

Kelly Sinclair:

budget. She's going to walk us through exactly how she did it,

Kelly Sinclair:

what worked and what surprised her along the way, and you won't

Kelly Sinclair:

want to miss this. I'll see you next week.