The D2Z Podcast

The Power of Podcasting - 142

• Brandon Amoroso • Episode 142

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In this episode of The D2Z Podcast, Brandon Amoroso interviews Casey Cheshire, founder of Ringmaster Conversational Marketing. They discuss Casey's entrepreneurial journey, the transition from running a B2B agency to focusing on podcasting, and the importance of building genuine relationships with podcast guests. Casey emphasizes that the true value of podcasting lies not in the number of listeners but in the connections made with guests, which can lead to significant business opportunities. They also explore the types of businesses that can benefit from podcasting and the importance of having a clear strategy.

Here's What You'll Learn:
❗The transition to podcasting was driven by the need for thought leadership and content.
❗Building genuine relationships with podcast guests can lead to significant business opportunities.
❗The focus should be on the guest, not the number of listeners.
❗Many businesses can benefit from podcasting, especially if they can create valuable connections.
❗Market timing is crucial for business growth and success.
❗It's important to have guide rails in place to avoid scope creep with clients.
❗Podcasting can be a powerful tool for B2B marketing and customer connection.
❗The authenticity of the conversation is key to engaging listeners.
❗Working with professionals can help businesses avoid common pitfalls in podcasting.

Timestamps:
00:00 Introduction to the Podcasting Journey
08:40 Transitioning from Agency to Podcasting
12:44 The Power of Guest-Centric Podcasting
21:35 Identifying the Right Businesses for Podcasting

Casey Cheshire:
Linkedin - https://www.linkedin.com/in/caseycheshire/
Ringmaster - https://ringmaster.com/

Brandon Amoroso:
LinkedIn - https://www.linkedin.com/in/brandonamoroso/
Web - https://brandonamoroso.com/
Instagram - https://www.instagram.com/bamoroso11/
X - https://twitter.com/AmorosoBrandon
Scalis.ai - https://scalis.ai/

Speaker 1:

Hey everyone, thanks for tuning into D2Z, a podcast about using the Gen Z mindset to grow your business. I'm Gen Z entrepreneur Brandon Amoroso, former founder of Electric and now the co-founder of Scaless, and today I'm talking with Casey Chesire, who's the founder and chief evangelist at Ringmaster Conversational Marketing designing, producing and promoting customer connection focused B2B podcasts. Thanks for coming on the show.

Speaker 2:

Thanks, man, great to be here.

Speaker 1:

So before we dive into the world of podcasting unironically on a podcast, can you give everybody a quick background on sort of your entrepreneurial journey and how you ended up in this space?

Speaker 2:

Well, it all started a few years ago when I was a child selling raspberries in the neighborhood. It starts out small, but I had been iterating and trying to make little companies here and there for a long time. But my big breakout was about a decade ago when I launched a B2B marketing tech agency. We did a lot of work with Salesforce and Pardot and we just went from zero to 30 employees almost overnight over the for a couple of years and then just ran that for about a decade. So that was the. That was the real big one. But I had a lot of practice swings before that, um, and then now we're doing this podcasting business.

Speaker 1:

What made that one, the big one versus the small swings?

Speaker 2:

It's a good question. Well. Well, you can only pick so many raspberries. But I did some other projects. You know one example I wrote a play and I thought let me just publish that, maybe make a play publishing company.

Speaker 2:

I'm not totally understanding that. What a play publishing company is is basically reading a bunch of shitty plays to find the one diamond in the rough and then, after you've done all that front-loaded work, you publish it and market it and then maybe you'll get paid. So I think a lot of it was following passion but not understanding maybe the underlying business model beneath a company. And so that would be a bunch of the swings were just following passion, seeing if you could monetize, and then understanding what the core business was. Did I want to read a bunch of bad plays to pick one and then market the hell out of that and then have so much front-loaded cost? Not really. So then I realized that was not for me.

Speaker 2:

But with the Pardot business, I loved Pardot and I was using it in my marketing career just as a marketer. And so then what ended up happening is people were like, hey, that's a great story you told about turning that company around using that tool. Could you help me out with it and so and there was a model beneath it there was the ability to have consulting um and great ratios so you can hire really good people, charge a whole bunch and and grow the company, and then also, I'd say, a great partner, right. So we had a huge partner with Pardot and eventually became Salesforce, but they sent us the majority of our deals.

Speaker 2:

So we had like a very mutual partnership with them.

Speaker 1:

Oh, that's awesome. That's not dissimilar from how mine was able to scale.

Speaker 2:

Yeah, with Shopify, did they send you most of the love?

Speaker 1:

Klaviyo, a lot of Klaviyo. Some Shopify as well, but not as much as Klaviyo.

Speaker 2:

Interesting.

Speaker 1:

Yeah, there's a huge movement in 2019. I think it was 2019, 2020, when the Shopify-Mailchimp relationship was deprecated and they basically told their merchants you should migrate to Klaviyo. You know that caused a lot of migration, work, a lot of growth for Klaviyo, not a lot of service providers. Klaviyo Now there's a ton. You know there are a dime, a dozen, but at that time, you know, it was very much a white space for us to dive in Market timing.

Speaker 2:

man is crazy, right, you just hit that market timing right, but you couldn't just be there that moment. There's a little bit of that groundwork, the relationships, establishing some expertise, and then the market timing flipped and then it's like grab the fishbowl. Time to go hire, hire, hire.

Speaker 1:

Yeah, we were already very well steeped in the entire Shopify ecosystem. Yeah, yeah, we were already very well steeped in the entire Shopify ecosystem. Yeah, I was just sort of seeing the writing on the wall that we should oh we should double down on this and pivot our agency into just being focused on customer experience and retention marketing, versus trying to do everything for everyone. Yeah, being able to pivot into something and go head first versus trying to have our toast in too many or trying to have our hands in too many baskets.

Speaker 2:

Yeah, picking the battles is tough. You kind of want to do everything.

Speaker 1:

Yes, I remember firing my first client and how weird and bittersweet it was because it was like I'm losing revenue, but I feel awesome.

Speaker 2:

I remember the first time I someone asked if they could, you know, like a la carte, pick apart a program and instead of doing 12 months I just want to do one month, as like a POC, and my my response was no. And and they didn't go for it. Neither did I. I felt so good after that call. I told everybody I was like I just said no, it was awesome.

Speaker 1:

Yeah, I mean the amount of time and hassle that you saved yourself. There's almost no chance. I think that that person would have converted anyways.

Speaker 2:

Yeah.

Speaker 1:

Something that I saw all the time the more that you would bend for somebody to try and get them across the line, more often than not it was never enough.

Speaker 2:

Yeah, it's the whole. Give the mouse a cookie, you know, and then they want a glass of milk, and then they want a blanket, and then a nap, and then eventually pancakes. You're like why am I making pancakes for these people? It's crazy.

Speaker 1:

Yes, the scope becomes pretty tremendous.

Speaker 2:

Yeah, and I also find there's like an inverse relationship to that with their appreciation of it. The more you, you like sort of bend and you try to give and be flexible with that, the less they appreciate it, which is just so counterintuitive.

Speaker 1:

You're like what do you mean? Brandon's not available at 3am on Saturday night to deal with whatever shit I have to send over? Now that was a big transition for us, especially as we grew. You know my early clients. They were used to me 24-7 doing anything and everything for them. And then obviously that's not a sustainable, like long-term business model, and so as we grew, it wasn't me servicing the account, but also we had to have sort of guardrails in place. You know I couldn't work for $5 an hour anymore because I wasn't just getting started and helping them out, and that was definitely a tough, tough transition.

Speaker 2:

And it can be tough, especially if you're having fun, right? I had a great mentor who made me calculate it out. Okay, how much are they paying you per month? Cool, what are? How many hours are they paying you per month? Cool, what are, how many hours do you think you're doing? And the math turned into like, oh you're, you're getting paid a fraction of what your agency would charge for, like your, your entry level person. But I was going like I was just doing too much and I wasn't, you know, because I was having fun. But it was like, okay, you need to like rein it in and have some, some guide rails here, so you're not, you know, accidentally letting them take advantage of you.

Speaker 1:

Yeah, part of that maturation process for our business was instituting a time tracking process and then our worst offender was revealed and you know, especially during COVID, access to people was so easy via Slack, email, phone calls, you know, everybody was just always online all the time, and so I think our effective hour really late for that client who was paying us like $20,000 a month was like $16 an hour.

Speaker 2:

Weird right. You wouldn't think that You'd think oh, it's a great client.

Speaker 1:

I know, and without that time tracking I would have had no idea $16 an hour and you know the the one-off calls the slacks here and there the hey. You know, let me go down to the. Brandon said no, but let me weasel my way into the. You know the right person within the team to be able to get them to do something. For me it was.

Speaker 2:

It was never ending you might have been losing money on that 20k oh, we were for sure.

Speaker 1:

I mean, it made our top line look better and it made me feel better but, it. It didn't actually help or support the business, and when we fired them, the team was pumped and that was the easiest sign that we had done the right thing.

Speaker 2:

Priceless morale building right there Exactly. You know what top line metrics. You know, like I, definitely have fallen in the trap of like either revenue or even number of employees, being like a almost like bragging rights when you're early in, but then later on you realize yeah, not really, Because there's some construction companies with 80% lumber and cogs that might be a $20 million company, but really it's like a $1 million company. They just have all their expenses in there.

Speaker 1:

Right, exactly, the devil's in the details with anything. Yeah, so you did the agency game for a while while and then you decided to jump right back in again. So what was the catalyst for going back in? But also, you know, pivoting to focus on this B2B podcasting.

Speaker 2:

You know I started a podcast many years in for the business. I needed thought leadership, I needed content. And you know I'd done the whole thing where you'd write a blog post on LinkedIn and either 12 people see it or 1200 people see it. But was the difference was like, you know, random sometimes, and or what image you put on there which was just so lame. So I was like what's an easy way to do that? So I just I just went after it, just launched the podcast, and there was no group like what we have now to advise you. There's like audio nerds, here's the mic to get man, but no one's there to tell you like how do you do this as a business and what business outcomes can you achieve? And so I just winged it and I had some great success with it. Man, I used it to.

Speaker 2:

I know you have a book. I used it to write my book, interviewing different people. Each month I had a theme of people that I'd interview and then I'd combine those interviews into a webinar and then that webinar became the basis for the text of the chapter in each book. So after 12 months I had 12 chapters and all on a theme around marketing automation. It worked really well and it also became like a capstone project. Everything I know is in this thing so that I can go on to the next thing. But yeah, so a ton of content that actually very quickly became too much content, right. So content was not an issue the pod ever again, maybe finding the right content or using the most of it.

Speaker 2:

But what ended up happening magically? I had this amazing interview with this absolutely badass CMO of a medium-sized SaaS company and she was awesome, great conversation. So I interviewed senior level marketers on the pod and and then she was like, hey, by the way, we're offline right after a great interview, we're migrating from Marketo to Pardot. I was like, no, kidding, that's what we do. And she's like, really, I'm like, yeah, and so we didn't know, neither of us knew that that project was happening, but we just hit it off. We'd spent like an hour plus hour and a half time together recently, had great deep conversations, and she was like cool, let's get our teams together. We got our teams together, they scoped it out and it was like a friends and family deal. We were like, just get it done. And it turned into like an $80,000 deal with no sales cycle, no competitor shopping anything. It was just like, let's do this deal for my friend and I told my team hey, let's take good care of them. And she told her team let's work with these guys. And we just made it happen. I thought that's awesome and that was on accident.

Speaker 2:

What if I made that on purpose? What if I actually selected the kind of guests I wanted to talk to build relationships with? Not like, let me trick you into a call. It's like no, let me get to know you and if I can solve some of your problems, I'm here for you, right? So we started handpicking. We found all the people with Pardot in North America. Right, you know, use a little bit of you know code tracking to see who had the code on their site. You know rank, ordered it by size, invited the top 100 companies that had Pard on, invited all their CMOs to be guests on my podcast. And the majority of them said yes, made some great relationships, got some friendships out of them, partnerships, referrals and a lot of customers out of that.

Speaker 2:

And it was so much fun to do it that way, right?

Speaker 2:

Instead of playing all those games that we historically have to play in the marketing world, all those B2B games.

Speaker 2:

Let me give you a blanket to meet your boss. I'm going to give them socks and then they're going to remember me and then maybe they'll get on a call with my sales rep, like all this BS. I was like let's just skip that and do one of these things where we just have a pod, we connect with our customer and we learn more about them and then if we can do business and help each other out, let's do it. So for me that was just. It was so different than all the games I was playing doing marketing automation. Then when I had a chance to exit that company, it was like no brainer, let's do this pod thing. People had started asking me the same way. They'd asked me to be part on hey, cool story about your podcast, can you help me with that too? I was like I'd love to. Let's figure this thing out. So I had a chance to re, re, like, do an iteration again in another company and start over.

Speaker 1:

but but help people launch podcasts what are, you know, the biggest myths that you think around podcasts, yeah it's all about the listeners right and we get this.

Speaker 2:

You know, whether it's b2c, b2, anything, b2g, d2c, any of these things it's all about like you get so fixated on the vanity metrics and wanting to be famous and wanting to have those stats. It's so counterintuitive. If you do it the right way, if you make the guest the most important person, it doesn't matter if anyone listens right. If the listens matter, you're competing with Joe Rogan and he's going to win, and Tim Ferriss and everyone else. You're not going to win that right. You might. I know One out of many, many, many people might, but you're not. It's like trying to compete with Mr Beast. It's not going to work, don't do it. But you don't need to because if you make it all about your guest and your guest you know going in is someone you could actually help out, your team could help out then let's make a relationship with them and if the value of the whole program is in that conversation and a connection with the guest, then you've paid for the episode just by having that conversation.

Speaker 2:

But guess what? People do actually listen and they really like when they're listening to a show. That's not pandering. I mean that's one of the reasons why Joe and other people are successful is they don't care if you listen or not, right. And so it's like, hey, my guest is most important, I don't care if you listen or not, the show is for me. I want to learn, and if you learn, too cool. And people appreciate the fact that you're not just like you're just joined I'm letting you join this conversation, but like you can listen in, but otherwise it's me and this person right. And so they appreciate that. And what's cool is, if your guest had a great experience because you made it all about them, they're sharing it with their tribe, with their network. Who's then going and listening to it? And some of them are going to stay. So you, organically, are growing your pod by not focusing on organically growing your pod.

Speaker 1:

The authenticity shines through as well.

Speaker 2:

Yeah.

Speaker 1:

In the content and I think listeners can pick up on that, totally that aspect of it.

Speaker 2:

Totally If you're not into it. You know we always our number one tip for hosts is never ask a question you don't want to know the answer to. Because if you don't don't ask, because your reaction to that question will be like oh yeah, great, thanks, or okay, or next question. You know it's just like no. Ask something you actually want to know and if your audience can't follow along, that's okay. They don't need to, they don't need to listen.

Speaker 1:

Yeah, that's definitely like training a muscle memory too. Yeah, or training like you would for for a sport. I think you know, when I first started doing the podcast, I would script all of them you know have some boilerplate questions, at the very least, that I could fall back on yeah but now I think it's actually more of a detriment than it is a positive, because I'd rather just have a free-flowing conversation, and you know it doesn't. You can still, as long as you have your high-level objectives, the way you're trying to get across and can arguably sort of sprinkle it in here and there.

Speaker 1:

I think that's better than trying to be super scripted. Anybody who I have on the podcast who wants to have all the questions ahead of time, that's more like an interview. It's not really a podcast.

Speaker 2:

That's a warning sign. Right there, that's a red flag. Hello, podcast. That's a warning sign. Right there, that's a red flag. Hello, red flag. This might not be the guest for you. I need all of your questions in advance. Okay, I don't even know what the questions are all gonna be. Um, you know what I like have having the first question be the same every time. It's like kind of like your, your go-to, especially if it can just launch your guest into a tirade and then maybe have some milestones after that, but at least the first one's always going to be the same and then you just let it ride, you just go from there yeah, I mean, mine's super simple.

Speaker 1:

It's just give us your background. Yeah, the podcast in and of itself is about entrepreneurship and your journey, so and tell us your story.

Speaker 2:

Right? You asked right at the beginning what's your story, man?

Speaker 1:

and then from there there's probably 50 different directions that it could be taken, depending on what that response is like. But also on the guest as well, to be an engaged guest and provide some material. I've definitely had some people on where they answer that question. I'm just like man, that was, that was tough. That was like, uh, you took it too far when it comes to distilling the message into a, you know, a 10 to 15 seconds.

Speaker 2:

Seriously, man, you know I love doing a prep call on my pod. I'm totally, totally got to have you on my pod and uh, have you, you know, experienced that too? We can compare and contrast, but like I always do a prep call, and the reason why is I've experienced those things you're talking about where your guest is just like they're either unbeknownst to them, they're like really boring right or they like have a terrible answer that you've heard nine times.

Speaker 2:

You're just like I can't. So I do a prep call, mostly so I can tell them what I want to hear and what I don't want to hear. Like please don't give me your resume, like I don't care, I'm not going to listen to it and if I stop listening I'm not going to ask any more good questions, right? I actually try to avoid stories at the very beginning because I find people are historically really bad at them. So at the very beginning I'm like give me a nugget, teach me something real quick, so that myself and the audience are in, and then later on I'll ask you how you came upon that knowledge. And that's fun, man, some people. One time one of our clients had a pod where their guests went on like a 10 minute rampage about like I don't even know they're just talking about some story, and they never got to it, you know they're just sort of like telling the story that never ended up.

Speaker 2:

You have, it's like when you have those friends who keep telling a story and you're dude, where's he going with this? And it's okay if they've been drinking or something. You're like, okay, that explains it. But if they haven't, you're like, dude, where's he going with this? And it's okay if they've been drinking or something. You're like, oh, okay, that explains it. But if they haven't, you're like I need to get where's the exit button for this pod?

Speaker 1:

I imagine that person you know. If they had been drinking, you know how terrible it would be.

Speaker 2:

Yeah, yeah, or maybe it'd be better, we don't know.

Speaker 1:

We don't know answer. That is true. I do find that some social lubricant can help with some of the podcasts that I've watched, which unfortunately, is not a reality for me being able to do things in person, but one day I think that'd be really fun to have an in-person podcast, because it would just change entirely.

Speaker 2:

For me. You build rapport in the prep, call that other podcasters, like Rogan's, going to throw a whiskey at you. Oh look, it's the latest whiskey from my friend who hunts deer and he has this whiskey. It's really good, try it. Here's a cigar right just to sort of build that rapport and loosen people up so they'll actually say something or two on the pod, not just have those little answers.

Speaker 2:

One of the things I found is if people give you those quick, little, like quick answers, short answers can really lower the energy of the pod, and so i'm'm always trying to find, like, where do I get those like needy answers? And I find that if people aren't in that place where their passion and their expertise overlaps, that's when I tend to get those short answers. And so, on the prep, I'm always listening for, okay, do they want to talk about this? They do. Okay, cool, can they Do they have any layers beneath that? Or they're like, yeah, I love SEO. It's like, no, you don't Like me, I hate SEO and I know something about it, so don't ask me, because I don't want to talk about it.

Speaker 2:

But I could, but I don't want to, but. Or it's like asking me about a P&L statement. You know, yeah, I could talk about it. Am I experienced as a fractional CFO? No, probably, should ask them instead, right? So those topics? No. But you know, if you say, casey, tell me about pods, I'm like blah, blah, blah, blah, blah, blah, blah. So, like a prep can be great for identifying what you want to chat about?

Speaker 1:

Yeah, definitely, I think the prep is something that we could incorporate. It's just always a function of time.

Speaker 2:

Totally.

Speaker 1:

As a business owner. That's a, that's a big component and that's also why you know, I'm sure a lot of people work with you is because they they don't have the time I mean, like you know, part of its time, part of its expertise, obviously, but that was why so many people would work with us with shopify.

Speaker 1:

It's not like they couldn't learn how to do it or they couldn't figure it out themselves. It would just take them 10 times as long and probably, you know, 10 times as much money versus just using an expert to be able to leverage that.

Speaker 2:

So you know, I was talking to someone today. He asked me the same thing. He's like oh, that makes total sense, it seems so easy. And you know the question. He didn't ask it but it was kind of like so what, why should I have you guys? I want to just go to use fiverr in the meantime and I I was like, dude, go do that. But the problem is, as you're learning, you know the 400 episodes between where you're at and where, where you would be at if you're working with us, like you're going to look like an idiot. So that could be okay. But like, if you want to skip all that, right, even with you. Like if you want to skip all the stupid emails and all the like in all the non-successful results, but you know what ends up happening is people pod fade, right, they don't see those results right away. Like no, this is lame. Only 12 people are listening and it looks dumb.

Speaker 2:

And you know I'm just gonna quit and so, yeah, you definitely want to work with, like the pros if you want it to work that makes a lot of sense yeah well, I really appreciate you coming on and joining us um and taking the time.

Speaker 1:

I think you know. The one thing that I'd love for you to cover before we hop is just like, as a as a business owner, what types of businesses should be thinking about podcasting? You know, are there? Are there areas where you've seen it perform well and others where it doesn't perform well? You know who's the one that should be contacting you versus who's the one that should not be.

Speaker 2:

Yeah, it's a great question and I don't have a flowery answer. Like everyone, I kind of do feel like everyone should use it. But but the real answer is that it's it depends on the value of that connection. If the guest you're connecting with could turn into a 20, typically we say $20,000 or more either. It's like a single deal, it's a partnership, reseller deal, any kind of relationship that could be at least 20K every year for you, then it's worth it.

Speaker 2:

Where it tends to fall apart is again back toward that Rogan days. We have done pods for people where it's a cool concept, but they have this store and you have to have a whole bunch of people listening to have a certain number of people go to your store, to have a certain number of people buy the CBD there, so just the sheer number and you're competing now with everyone else's ears. You know everyone else's podcast. So the B2C can really fall apart. So B2C has to really think about reseller partners or you know some co-branded folks or some folks that might distribute them or resell them Like. So you really need to think about a relationship where that can really work, someone who might be just driving business your way and again, I love partnerships, so that works great. It's just they have to have value. Now, the company that I talked to recently, where one deal takes forever but it's $100K, it's a no-brainer Because in that case our services are like a rounding error. As a part of that, you know cost of acquisition.

Speaker 1:

Yeah, no, that makes a lot of sense. I appreciate you walking us through it. I'm obviously a big proponent of podcasts. I think that they be beneficial well beyond just who listens to them. I mean, it's a source of content, it's a source of, you know, getting to meet and connect with new people, and you know. The benefits are far beyond just how many people are listening to it, though it wouldn't be, you know, the end of the world if as many people that.

Speaker 2:

Listen to joe rogan, listen to my podcast and they should.

Speaker 1:

Yeah, I don't know if I'm that cool, but I'll. I'll take it.

Speaker 2:

I'll take it well, yeah, you do. You didn't offer many whiskey or cigar, so yeah, you're almost there. Eight out of 10.

Speaker 1:

Next time round two. Well, I appreciate you coming on. Before we hop, can you let everybody know where they could find you and connect with?

Speaker 2:

you online? Yeah, totally so. The website is ringmastercom. Shoot me a note on chat. I'm Casey at ringmastercom. If you just want to pick my brain on pods and you know hey, you want to do it yourself. But like just curious what are some of the ways that people can really screw it up? Just shoot me a note. I'm happy to give you my advice, shoot you a video, whatever. How I can, ever I can help. Pods are great. I just want to connect the world, one podcast at a time. So shoot me a note my podcast, which you. I want to get you on there so people we can link to it one day. But yeah, yeah, it's called the Hardcore Marketing Show and the core is spelled like the Marine Corps, so C-O-R-P-S, two words. So hardcore marketing. Maybe there's a link in the show notes. But either way, check that show out. That's a lot of what I do and one day, soon, we'll get you on there, brandon.

Speaker 1:

Awesome. I appreciate it. Well again, thanks for coming on, for everybody listening. As always, this is Brandon Amoroso. You can find me at brandonamorosocom or scalistai. Thanks for listening and we'll see you next time.