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A
Hey, it's Kendra and Taylor and we're here to make Advisor Marketing simple. Today's guest is Jesse, the writer behind the Best Interest blog and host of the podcast Personal Finance for Long Term Investors. He's also an advisor at Cobblestone Capital Advisors. Now Cobblestone's team of 42 have been helping clients for 39 years. And Jesse, he's been in the industry for for four. The firm manages around 3 billion in AUM and Jesse personally oversees about 80 million in assets. His five year goal is to grow his assets to 200 million. Welcome to Advisor Marketing Made Simple. Jesse, what's that big question you want to dive into today?
B
Hey guys, I think it's that I feel really good about my middle of funnel, but I feel much less good about my top of funnel. And so I want to bounce some ideas off you guys on how to focus and improve on that.
A
All right, we are all about marketing focus. So let's dig into a little bit about the show. Typically, who's the ideal client you're trying to attract with the show?
B
Yeah, so I've really struggled with this. I've only been in the industry for three and a half years now and so I think maybe from a scarcity mindset point of view, I haven't really wanted to turn too many people away, but I understand it's an important part of our industry and I knew you guys would ask. I have three archetypes in mind and I can cover them very quickly. The type A business owner or upper level executive with a business, busy family, busy life and a complex income structure. Number two would be more mom and pop type folks five years or less to retirement who have saved and accumulated a lot and now need help with the retirement plan and decumulation. And then the last one's very unique, but it's hardcore DIYers people who say I never thought I would hire an advisor but my life has now changed or but I realized that my spouse needs that support. And it's pretty unique because they might think they know more than most advisors, maybe some of them even do. They're right. But I think that's something that my middle of funnel is uniquely positioned to work with those kind of people.
A
Okay, and when you're thinking about the pre retiree five years out, what's your asset minimum?
B
Technically speaking, 500,000. But in reality it's more like 1:5,000,001.
A
Quick clarification around the type A business owner. You mentioned that, but then also maybe kind of like professionals or someone with equity comp. I caught something there. Which one is it?
B
It's someone with more of a unique, complex income structure. Yeah. So what that might mean. It might mean someone who's like, taking a large draw because they're a business owner. It might mean the director of XYZ at some large corporation who's getting RSUs and ISOs and that kind of thing.
A
Okay, here's an interesting question. When you think about the clients who are actively converting from your podcast, is it all three of these or is one kind of coming out as a front runner?
C
It.
B
For sure, it's the fact that almost all of my content is geared towards the latter two. In mind, that would be the mom and pop retirees and. Or the hardcore DIYers. There's a lot of overlap between those two in my experience. So a hundred percent those are the people who are converting.
A
Can you paint me a little bit of a difference in the contrast? You know, because a doir could be five years from retirement. What do you see between those two?
B
Yeah, I. I think maybe just the. The differentiator in my mind is that simply that idea of I never thought I would hire an advisor. I've met with advisors at four before, and I felt like I knew more than them. I consume so much of this kind of content. Maybe. Maybe that's one of the big ones. Is, is There are some DIYers out there who say, yeah, I listen to 10 different podcasts. I listen to Taylor, I listen to Jesse. I feel like I know so much of this stuff. Whereas maybe the more mom and pop style that I talk about is someone who says, I know I have to save, and I've saved for 40 years, and now I've got this $3 million nest egg. When you say Roth conversion, I don't know what you mean. When you say IRMAA, I don't know what you mean. Whereas the hardcore DIYers, they know what those things are. So I think that's. Does that help explain some of the differentiation?
A
Yeah, definitely. When you think about converting clients from the podcast, give me a breakdown. What percentage you think is that kind of mom and pop five years from retirement versus the hardcore D?
B
Yeah. In terms of people who have actually come forward and now are working with me as clients.
A
Yeah. Like 50% are the mom and pop. 50% of DIYers or some other configuration.
B
Probably 2/3 to 3/4 are the mom and pop. And then the last third or quarter would be the hardcore DIYer.
A
Okay. If you were to narrow down on one of These to really start to, you know, build this podcast for one of them. Is there one that speaks to you more than the other?
B
I. I just think they're probably for a. For a few different, different reasons. Not only are there probably more mom and pops out there, but they're probably a little easier to work with. Right? The hardcore DIYers, by definition, a lot of them are very intelligent and they know a lot of the stuff. It's kind of like advisors talk about. It's engineers and doctors and it's more of those types of people. My only hesitancy though is that, well, listen, it's like if no one's fishing in the pond of hardcore DIYers, because it's too hard to catch the fish there, and if I'm the only one fishing in that pond, maybe from a competitive business point of view, there's an opportunity and it's like, do I want to fish in the same pond as Taylor? I don't know. That's a pretty competitive pond. So that is part of my struggle.
A
My question would probably be, which way is the most enjoyable way to build your business?
B
Yeah, no, that's a good question. I think it's going to be working with mom and pop.
A
Now with that particular segment of those, you know, five years out with at least 500K, you know, ideally 1.5 or more. What a couple of those big pain points, you know, painful, urgent, expensive problems they're willing to pay you to solve. Like, you see those coming up. Big themes.
B
So the really big themes. Do I have enough to pull the trigger today? Can you help me feel more confident that I'll never run out of money? I've heard that the tax time bomb is ticking, that taxes and retirement can be this huge problem. It's this looming shadow. But I have no, I have no way to define that shadow. It's like a bad dream. Like I can't put my finger on it. I just know it's lurking out there. Those are probably the biggest ones that I see.
A
Okay, awesome. So let's talk a little bit about your actual funnel. So with your podcast right now, middle funnel's working pretty well. What kind of downloads are you doing monthly?
B
As we record this in July, it's gonna be an all time high month. Right now I'm at about 12,000 for the month with a week left.
A
Awesome. Okay.
B
Yeah.
A
And for the actual podcast, what kind of calls to action do you have, if any?
B
Yeah, a few different ones. Some subtle, some and. And pretty frequently I just try to drop that subtle hint of, here's a story of working with a client. Here's a conversation I had with a prospective client. Just those reminders. Here's something I'm dealing with at work. So it's just these subtle reminders that, yes, I do this professionally. When it comes to the really hard call to action, though, one of them is to ask listeners to subscribe to my weekly newsletter because then that allows me to kind of begin that weekly drip on them. Another one is to go listen to this specific episode I've recorded that dives into the details of the practice that I work at and kind of how this content ecosystem that I've created overlaps with my actual financial planning practice. So there's a couple of those that they don't maybe go quite as far as to say, reach out to me tomorrow and ask me if you want to. Let's, let's schedule a call. Like, I don't quite go that far, but I just, I move them kind of down the funnel.
A
How many people do you have on your email list right now?
B
I just pruned it a lot because I had a lot of inactive Downloaders, but about 4,000 with maybe like 75% open rates, 20% click rates.
A
That's awesome, man. That's great. And when you are booking calls, are you making calls to action in email that are converting or you. Does it seem like the podcast calls to action or converting?
B
I guess I'm not quite sure. I mean, I can give you a 30 second answer that, that might work. Is that part of my, my website? There's a work with Jesse page and I encourage people to go there. I have a bunch of different links that point there and once there, people submit their information via a form. And so that's really the way that people fall from my content ecosystem into maybe and becoming a prospect.
A
That's a manual form, right?
B
Correct.
A
Okay. And for your sales process, I know you're part of a bigger firm, but you essentially point everyone to that kind of standalone personal blog, correct?
B
Correct. That's where it starts. That's where it starts. And I do a little bit of vetting and a little bit of filtering. I try to get some more information from them. And then once someone truly is a qualified prospect, I would say such that we're really beginning those one on one conversations about them working with my firm. I mean, not that it really matters, but that's where I transfer over and I start using my, my work email address, as it were.
A
Okay, gotcha. That's really Helpful. And as far as, you know, the content roadmap, or how are you choosing the topics you're putting on the show?
B
A lot of it is listener inspired at this point, which I found to be this, like, kind of amazing, virtuous cycle. Because A, it helps me just create ideas. Like, you know, sometimes I feel like I'm running out of ideas and I never feel like I do now because I have all these listeners and readers writing in. And then B, I get to see the patterns of the questions that I'm getting. And it's just so natural. Like, okay, if my retiree audience wants to learn about X, Y, Z, that's what I'm going to focus on. My AMA episodes have been some of the most popular ones where I get five to seven detailed questions from listeners and I do these deep dive answers. And because it turns out that if people are asking, then other people have those questions too.
C
Absolutely.
A
That makes sense. What have you found so far to be effective for growing the show? Like, what have you tried and what's.
B
Worked specifically for growing the show? Probably two main things. One is podcast guesting, and then the second one is just trying to cross promote as much as I can between my blog, my newsletter and the podcast. Like every single way that there can be connective tissue, I try to do that. Every blog post, for example, says that the first line in my blog post is, here's what's going on over at the podcast this week. And then every blog post ends with, and here's my weekly newsletter. You should sign up and, and, and kind of like in any permutation you can think of, I try to get these pointers from one content to the other.
A
What's your monthly website traffic look like?
B
Kind of ballpark wise, probably about 20,000 visitors a month.
A
Okay, awesome. A lot of good stuff to work with. Taylor, what's coming up for you?
C
Yeah, I mean, Jesse, you're doing so many things really, really well. This is kind of, to me, the fun stage when you get to get a little bit more narrow and clear and just kind of pour gasoline on the fire here. One maybe clarification I want to make here and feel free to disagree because I'm just kind of thinking about this on the spot. You were talking about this like mom and pop investor versus DIYers. I like, I don't even think about that. I would argue that if you're hosting a finance podcast and we're talking before hit record here about like Dave Ramsey and some of these, like, more surface level shows so let's set them aside. I mean, the content on your show is. Is fairly technical. I mean, not overly technical, but, like, you're talking about technical concepts. So I would almost argue, like, most people that are listening to your show are somewhat educated, which is why I kind of call this education based marketing. And these people are fairly educated. They're coming to you fairly educ. It's hard for me to believe there's. There's a lot of people showing up on your doorstep that are just mom and pop investors who don't know what a Roth conversion is. Am I wrong there?
B
They've heard of it. They've heard of it, and that's. You're. You're not wrong. You're not wrong that people have probably heard of these concepts. They might not know how to execute it. It's like, have you guys ever heard of this? There's kind of like four stages of knowledge, and really succinctly, it's like, you don't know something. You understand it when it's taught to you, but you can't reproduce it yourself. The third stage is you can reproduce it yourself, but you can't really teach it to someone else. And then the fourth stage is that you actually know it well enough to teach it to someone else. And I feel like a lot of the people I'm dealing with are maybe in that second bucket where it's like, yeah, when you explained Roth conversions to me, it made sense. Then when I tried to sit down with a spreadsheet myself and execute, I couldn't figure out how to measure if I was actually getting tax arbitrage or not. It's that. It's that.
C
I think that's a. That's a really good example. Like, when I think of mom and pop investors, like, I literally think about my mom and my dad, who literally have no idea what a Roth conversion is. Like, I'm speaking a completely foreign language to them. They're my parents, and they're not even listening to my podcast. So, like, they just have no desire to learn about this stuff. So the people you and I are talking to, they have a desire to learn, and they are somewhat educated about these topics.
B
Yes, there's a.
C
There's a variety of listeners, some who, like, I know all of this stuff. I know I could do it on my own. But, Jesse, I don't really feel like doing it on my own. I'd rather spend my time elsewhere. So I just want you to implement it for me. And then there's those people, like, Gosh, Jesse, you, you know, said something on your show like, I didn't know about that thing. I. I don't really want to figure it out on my own. I can't figure it on my own. So I want to hire you to help. So I don't know. I'm just. We don't need to get too stuck on this, but I'm just don't really think too much about mom and pop investors versus DIYers. Just in my mind, they're all. They're all DIY. They're all people that are out there trying to learn this stuff on their own. And there's a tiny percentage of our audiences that just raise their hand and say, I. I can't figure this out, or I don't want to figure it out, or I don't want to do it on my own. So I would just. I think you're doing all these things really well already. Just, like, continue to produce the content you want to produce that speaks to the pain points of your ideal client, which you're very, very clear about. And I think you just continue doing that. And I think, you know, kind of where we started the show where you're maybe feeling stuck or just want some help is I know I have this awesome thing. I know I have this great podcast. 12,000 listens a month and growing. Um, I just need to get more people to listen to this show because I know more people listen to the show. The more people reach out to me, the more people become clients. And that is part of the challenge in the podcasting world. Just because discovery is so challenging, that is just like this kind of slow crawl. So you tell me, but we can spend most of our time here talking about how can we get more people to listen to the podcast. Maybe the first question is, you mentioned guest podcasting. Like, how did you go about guessing on other shows over the last few years?
B
That in and of itself can be a bit of a slog, but the method and. And my production team helped me with this because they kind of offload some of that. That work. The method was basically starting with identifying a list of potential shows that I might want to guest on. And one of my struggles is like, do I only want to guest on other money shows? And is that actually useful? Or should I branch out into, like, I don't know, like, you know, are there shows out there about lifestyle for retirees that have nothing to do with money? Like that. That's. So that was part of my thinking. But anyway, the first step was Identifying shows you want to guest on. I wanted to guest on, trying to produce really unique outreach. I mean, you guys both understand this, that like, we get so much outreach from people wanting to guest on our shows. And 99 of it is junk, just absolute junk. And it's like, how can I stand out from. From that junk? And now in the age of kind of AI email sweepers, sometimes you're just getting swept away before you even get a chance to get in front of someone's eyes. So if there's any sort of personal connection, that always really, really helped, like, how can I actually do real life networking or like LinkedIn networking to get in front of this podcast host? And then that to me is actually the hardest part because then once I have their attention, just trying to put together a compelling show for their audience and almost me taking like the lion's share of the work, like, here are all the things I will talk about. Here are the kind of things, like questions I' ask you or questions you can ask me. Like, you don't have to think about putting the show together, Taylor. I've done it for you. I found that to be. To be pretty effective.
C
How often are you guessing another podcast or how many other shows have you have you guessed it on?
B
I've got one that's recurring. That's pretty nice because it's a reasonably big show and, and probably like twice a month. I'm one of their guests on their Friday episodes.
C
Is that Stacking Benjamin?
B
Stacking Benjamins? Yeah, exactly, exactly. And then outside of that, there have probably been maybe like two a quarter for the last couple years. Some big and some very small.
C
Okay, is this a path that you want to go down? Do you want to build a better system process to guest on. On more shows, or are you thinking of other top of funnel activities?
B
I mean, it, it. Yeah, I mean it certainly would. It's not something I'm opposed to. And I enjoy guesting on other podcasts. I don't know if it's the most effective thing. And I mean, one thing, this is one of those, like, availability bias issues where if I go onto Facebook because of my search history, I get served with ads from other advisors. And sometimes I think to myself, like, huh, could I create some pretty compelling ads to capture leads that way? Like, is that the way I need to start pouring gas on this fire? And so I'll start with that one question. The second question I'll throw out there to you guys is there's this little disconnect between all this content work I'm doing and then actually using it as a tool locally here. Like when I think about this podcast and very few of them know that it's been reasonably successful. And so one of my questions for you guys is like, how can I start using this tool? Better to actually make these COIs realize like, whoa, this, this is kind of unique and interesting. Maybe I should be sharing it with, with my clients.
C
There's a lot to unpack there. Yeah, maybe, maybe I'll start with your comment saying, you know, I'm not sure if guessing other shows is very effective. I'd argue that's probably the most effective way to grow the show. The hard part is getting onto the show and getting onto a show where your ideal client lives. I'm good friends with the Stacking Benjamin guys, great people, giant show, but like their audience, there's not a ton of overlap between their audience and your ideal client. Right. So it's good visibility, it's good networking. I've been on their show before, it's fun. But it's probably not like a show that I would spend a bunch of time and energy on just because my target demographic is a little bit different. Nothing against them at all. So the challenge to me is getting onto those shows where your ideal client does live and then positioning yourself properly on those shows. Like I like the idea of guesting on, you know, lifestyle type shows, not your traditional retirement shows. Again, still there's a challenge of like getting on there. Your angle on that show just might be a little bit different. We're probably not going to get into the weeds of like Roth conversions and pairing them with donor advised funds. But it might be like, hey, I specialize in working with people in retirement. And what a lot of people don't realize is when you get to retirement, like you have this giant tax problem, you have all this pre tax money saved up and most people don't realize like what sort of tax issue that creates and just you kind of do keep it surface level but still talking about that ideal pain point. And then whenever I guess on other shows, the host is not always great about highlighting your podcast. And the purpose, in addition to showing value to that audience is to move some of that audience to your show. So I, I do think very intentionally ahead of time before going on these shows, like, how am I going to weave in my podcast to this conversation this very specific topic that I'm going to talk about. So I'll say things like, you know, just the other week on the Stay Wealthy retirement show, you know, a podcast that I host, I covered this topic, and so I'll slip things like that in there throughout the conversation. Doesn't feel, like, overly promotional. It's like, oh, yeah, we actually talked about that the other day. Or I had this guest on my podcast, the Stay Wealthy Retirement show, and I'll kind of weave that in. And every time I do this intentionally, I see a pretty large uptick in. In listeners on my end. It has been a really effective way to grow. But, yeah, the challenge is getting yourself onto those shows. I mean, I don't know if we're gonna. We need to go into the weeds here because you. You kind of need to figure out the best approach for you. And it could be. You know, part of it for me was in person, networking, going to fincon every year, going to podcast movement conference, shaking hands, staying up way too late, drinking way too much, just, you know, meeting people and befriending people. But, you know, it turned into a lot of great connections. You know, it could be cold emails, it could be leveraging your existing network. Somebody who knows somebody. Can you make an introduction. But, like, it is a very, you know, boots on the ground, pound the pavement, kind of find my way to these opportunities, short of hiring an agency, which would be really expensive, but I do think is really effective.
B
Did you find Taylor at. At this point, just because, right. What you're doing is working so well, Your podcast has grown so much. Do you filter based on the other podcast size at this point? Like, is there a point, like, some point in time where you're like, yeah, it's just not worth pursuing a podcast that quote, unquote, only has 500 downloads a month.
C
I haven't really been presented with that opportunity where smaller shows are reaching out to me. Like, please, come on my show. I definitely want there to be some momentum there. Not like, I just started my show. Come on. If it was a friend, I'd probably find a way to support them. But, yeah, I don't know, because I still think, like, hey, there's 500 people. If I come in and add massive value to the 500 people listening, and 200 of them jump over and subscribe to my show, it's not a small number in the podcasting world. Like, that compounds pretty quickly. So, yeah, but. But if I'm doing the outreach, I'm certainly not reaching to smaller shows. And still to this day, a very easy way to tell how big or small a show is is by the number of reviews. So, you know, it lines up like the math almost lines up perfectly with the number of Apple reviews that you have versus my reviews. And your monthly downloads. And my monthly downloads. Like, the math almost like works perfectly. It's really funny. So it's an easy way to kind of screen for those shows and determine how, you know, large or small, that show might be one thing that came.
A
That came up for me as we're talking about this is Jesse, you said you're doing this like twice a quarter, but it'd be a really interesting thought exercise if you said, I need to ramp this up to like twice a month. How would your process change? What might you do differently? Or four times a month? Like, have you really built a systematic, thoughtful approach? That's kind of one thing I would consider. The other thing that I kind of thought about this is like on the fly is, you know, we had a conversation with Tiffany Charles, who's a coi, you know, conversation. And the way I kind of think about networking, like behind the scenes, I love building relationships. So I really think about, like, how could you almost be a COI networker for podcasters who are in this kind of circle and like, really truly ask, how do I add value to that person and build a relationship and really see it that way first? And you could build, you know, some connections that way. Like, I think about, I heard this advisor who did like really badass dinners. I can't remember who it was. It was on the Altruist podcast for their ideal client and it's just like, cool. You know, what if you found a way to put together. I'm really reaching now, but a mastermind or even just simple one to one connections to connect with these retirement podcasters. Like, could you host a quarterly event where you invite these really high caliber people and you bring in like an expert on branding or speaking or, you know, Taylor got a voice coach. Like, how could you see yourself as like a COI kind of builder with podcasts who have your ideal audience? It's just like a completely different way. And it's not like you have to really go into this with like, how do I actually really help these people and give them something that, that I would also want? And it's, it's not just pie in the sky. Like if you listen to Tiffany Charles episode, like, she is very thoughtful and helpful and systematic. So building system of COI approach to podcasting for top of funnel guesting with the intent to, you know, increase your podcast guesting to two to four times a month. And then when you're on that Show. I love Taylor's tip about how do we really, in a classy way, weave in, like, a gentle nod to your show. And then at the end of the show, maybe you have like, you know, a stronger call to action show, or you have a different offer. So if they don't hear, you know, if they don't pick up on the show, like, hey, here's a really cool, you know, lead magnet or thing you've put together, that's another way that you could just capture more of that traffic on your email list. I think that's, you know, kind of a secondary thought approach, but that way it gives you a couple things to offer, a couple ways to connect since you already do have that email piece kind of rolling.
B
Yeah. Yeah, that's interesting. And I will share with. With you guys and the audience too. Like, I probably have a series of 10 poor failed lead magnets out there just trying different things. And then about three months ago, I actually switched over to Kit, which I think you're on Kit Taylor. And I know Kendra, you're familiar with Kit. And I was like, okay, let me revamp this. A lot of my email capture, let me revamp a lot of that. And I, I created a new lead magnet that's been, like, more successful than every other league magnet I put together combined. So that's one I need to start adding in more to and just promoting the fact that that's out there. And then you reminded me of something there, Kendra, which is like, okay, we're all, most of us listening are probably familiar with Josh Brown for Brit Holtz. And, and when I pick up on him talking, he clearly has so many connections in the media, right? The financial magazines, financial newspapers, Wall Street Journal, cnbc, all that kind of thing. And just some of the stories that he's told over time, I'm like, okay, this guy was clearly very deliberate throughout a lot of his career of just building those connections with journalists. And now, I mean, and for a long time, he's been reaping the rewards of that. So I see what you're saying. I need to kind of wrap my head around what that might look like. But that kind of deliberate coi building that doesn't directly lead to new clients, but instead leads to growth in the funnel. In the middle of the funnel. That's. That's a really interesting idea because because.
A
Really you're based off of what you share with us, your middle of funnel and bottom of funnel are working well. So you don't actually need the clients. You need the Visibility. If you pour people into the top of the funnel and you do it, you know, thoughtfully and you're clear on, you know, who you're talking to. As long as you keep those pieces consistent, like, you should attract more listeners and a small portion of them will, you know, convert to a call.
B
Yeah, yeah, exactly. Exactly. I think I. I'm sure you get this, too, Taylor. It's so nice. It's interesting. Sometimes, like, someone will start listening, and then a couple months later, they might reach out to you and they're like, hey, Taylor, I. I've listened to 40 of your episodes over the last 60 days, and you're like, okay, the middle funnel has clearly worked for that person. Yeah, right? And. And now it's just about right. How can I get more versions of that person? And the answer is, is. Is top of funnel exercises.
C
Yeah, yeah, I. I heard what Kendra said a little bit differently. I don't have, like, the perfect suggestion for you, but I agree with Kendra that she's really good at networking, and she's really good at doing it authentically and really good at building other people up without really expecting anything in return. Like, she's intentional about it. Like, she knows what she's doing. This isn't just, like, by accident, but she is really honest and authentic about it without expecting anything in return, but also knowing, like, in return she's going to have some great relationships, really, that she can potentially benefit from, lean on in the future. So it did make me think, like, in the podcasting world, think about growing your podcast. The reality is, is that if someone listens to my show, they're probably listening to Ben's show. They're probably listening to Roger Show. They're, you know, like, these listeners, they listen to all these different shows. And so, like, it's not as if I need to, like, protect my show. And I don't want any of my listeners to go elsewhere, because they already are. And so I have found a lot of benefit, like, lifting up other podcast hosts and, you know, you could experiment with a version of that. Like, you do have, you know, a fairly large audience in a digital world with your blog, with your email list. You know, I know you're linked to quite a bit by abnormal Returns. Like, you know, I see your name quite a bit. It's like, again, I don't know, this is like, the perfect solution here, a good solution, but, like, you know, you could write an article like, the five best or ten Best Retirement podcasts or finance podcasts that I love. And, like, you know, you throw Roger's name in there and you throw Ben's name in there and you write a nice thing and like, maybe you've already done this, I don't know. And you reach out to him like, hey, like, I wrote this thing, I included you in it. Like, like things like that. I think I'm thinking about Bolden or new retirement. You know, you write something about, like, some of the, the top tools for retirees to use, and one of them is Bolden. And you go to Steve and you're like, hey, Steve, by the way, I just wrote this article. You know, I get X amount of, you know, visitors per month. I wrote this article. I highlighted you guys. I hope it helps. Like, that's it. And you start to build some great relationships that way that you can potentially lean on in the future. And then the other way I was thinking about it was like coming at this from an angle of helping them out. I think this is what Josh Brown did really good. Like, it's not just like building the relationship with a journalist, but it's like, they have a job to do and how can I help them? How can I make their job even easier? And Josh is really great at, like, getting on camera and saying something really controversial that gets a lot of, you know, views and clicks, like, how can I help them out? And maybe you already know this, but when I was on Stacking Benjamin's for the first time, I was, I was on as a result of a cold email that I sent Joe at 4 in the morning because I went through this crazy journey with my house and this lawsuit, and I wanted to share it with a large audience to help, to literally just help other people who might be in a similar situation. And knowing his audience, and I was like, I got this crazy story, Joe. This is a shot in the dark, but here's what happened. It literally resolved this morning. And I just want to share it with. With your audience and try to help them. And he responded, had me on the show, like, so it was like a cool story because they love saying, you know, talking about cool stories and something applicable to their AUD audience and a way to like, help them. So I think coming out from that angle, rather than like, hey, I'm the expert, have me on your show to like, share my thing. It's like, I know that your audience has this issue and I've got a solution for it.
B
Yeah, yeah.
C
So lots of impact there.
B
Totally. But, like, you know, I don't know if you guys have read the Go Giver or if you've heard of that idea before, like the go get. I mean, that's kind of what you're talking about. And I admit, like, sometimes I struggle. In practice, it's like, in theory, of course, I understand what you guys are saying. And then in practice, there's always that. I go back to. I used the term before almost that scarcity mindset of just like, I get it. I'm a, I'm a career changer too. Like, I'm sitting here, I'm 35. I've been in this industry for three and a half years. I've got a baby at home. You know, like, I've got food on the table. And part of me is like, don't mess this up. Seize the opportunities you have. And this little voice in the back of my head is like, well, if you just give, give, give, give, give, and you never expect anything back, what if nothing ever comes back? Now, I know that's an irrational voice, but. But yeah, I, I appreciate you guys sharing those ideas because I, I have to do better to internalize your advice.
C
Yeah, I, I get it. I. My head goes there as well. And what I often fall back on. And this is a somewhat egotistical comment. I believe about myself that I just think, I think my show is really good. And if they go and listen to somebody else's show, great. I still think mine's better. Maybe I'm. That's not true. You know, there are other great shows out there, but, like, I just fall back on. If I just focus on creating really high quality content, I'm really intentional. I spend a lot of time on making it the best possible thing I can make. Then, like, who cares what else they go and listen to? They're always going to come back and listen to my show because I put so much time and energy into it. But I hear you. It is tough.
B
Yeah, yeah, yeah.
C
Go ahead.
B
Oh, a question for you, Taylor and, And Kendra. I mean, I mean, you, you might have experience with this, but do you have any thoughts on when it comes to podcast guesting that a lot of the financial podcasts out there, if they're really, you know, it's, it's. They're targeting towards fi. The financial independence movement. They're just helping people learn personal finance in general. They skew anti advisor, in my opinion, or at least they skew anti certain fee models. And so I'm just curious, like, what your two cents are on that. If you've guessed it on podcasts before, where you've kind of known that maybe there's this undertone of like, oh, we're having a financial advisor on. And so I've certainly done some of it myself and found mixed results. But I'm curious if you have any kind of expert advice on that front, Kendra.
A
A better question is, are they a good client for you? Even if they liked hearing from you, is a fire audience going to be, you know, those kinds of people? Are you going to be excited to get on a call with them? Are they going to be aligned with the problems you're excited to serve? So I, you know, I do see that there, there could be that, that bias for sure. But I've seen a lot of my clients who've specifically tell me I actually don't want those kinds of clients. So instead of asking whether audience like me, I first ask what I would I like working with their audience, you know, and then we can, then we can consider the bias. But I think, like, you know, if, if that personality fit isn't feng shui with who you're excited to serve, like, that's not a good audience for you.
B
Yeah, no, I, I, okay, I like that answer because it does help me maybe differentiate between growing the podcast downloads versus growing the converted clients. Right. And those are two different things. And guessing on some of those podcasts I know will increase downloads. I'm not convinced it'll increase the revenue. The bottom line, have you guys either, have either of you guys ever, whether it's you, Taylor, with your podcast, or Kendra with your clients. So it's like if we know that we have some DIYers in our audience who are just there to learn, and they're never going to reach out to us in the first place. Have you ever tried to leverage them as COIs in their little friend groups in their families, saying like, hey, listeners, I know some of you like to do this on your own, but I hope you understand that maybe some people in your life aren't in that same bucket. And so if they need a trusted financial planner, I hope you'll reach out to me. Is that, is that an avenue that you think would work?
C
I think it could work if it was positioned properly. I mean, it's a pretty passive call to action. You're expecting people to jump out of their seat and go tell all their friends about you. I guess I just think about it from, if I just provide a ton of value to these people and I'm a trusted expert, that if they come across somebody in their life, I mean, people love making referrals like Especially when it's on their own, they're not told to. It's like, you know, they come across a family member that needs retirement planning help and they don't know what they're doing. Like, hey, I listen to this guy every week on this podcast. Like I do it myself. But like, he's really sharp and you should reach out to him. Like, I think it just happens just organically. It'd be interesting to experiment and I'd probably put a little bit more thought into like, how can we try to squeeze as much juice out of the call to action as we can? But yeah, I haven't done anything directly to those people. It's like, I just assume, Jesse, you're talking about these other podcasts and maybe anti advisory, anti fee models, like who their audience is. I1 want to make sure like the audience meets my general criteria. High net worth, pre retiree, retiree, older demographic. Like as long as it meets that criteria, I don't really care what their philosophy is around advisors or paying anybody or what the host beliefs are. Like, doesn't really matter to me. I assume that 99% of my audience never gonna hire me anyways. Like that they don't wanna pay an advisor. Otherwise like I, my firm would be $20 billion. Like so I don't know, I just, I just assume most people aren't gonna hire me anyways, which is why I just fall back on, just create super high quality content that speaks to my target client and everything else kind of seems to fall into place. Now I do have to have some strong call to actions to move people. I've shared that story before. Like if you don't give people any direction, they just listen to you forever and just think, Jesse's a, you know, personal finance blogger, you know, that he doesn't, you know, actually have a firm and he's taking on clients. So there doesn't be that strong call to action. Before we run out of time here, I just want to make one comment. You mentioned cois and leveraging your cois to help grow the podcast. I don't think it hurts to make it known that you have this show and if you have some credibility around it, number of downloads it gets or an award that you won and finding ways to like include that in your email signature or weave it into conversations. Or maybe they're on their, your email list and they see it in your email. I just think like, it's hard to move somebody to go listen to a podcast that doesn't normally listen to podcasts like, if they're listening to personal finance podcast, retirement podcast, chances are they're already subscribed to your show. So I think it is potentially okay from a credibility standpoint, but I don't think it's going to be a huge needle mover. The other thing I wanted to bring up before we ran out of time was you had mentioned. Hey, in every one of my blog articles, I talk about the podcast or include a link to the podcast. I don't expect this to be a huge needle mover, but one issue I do see, I think I'm looking at the most recent one, is you just have this Spotify embed at the top. And so that's great for me because I listen to my podcast on Spotify, but 75% of people listen to it on Apple. And so what I've pivoted to is I just include a link to Apple, Spotify, and YouTube, but, like, specifically for that episode. So the little bit of manual work there that my VA does, but for every episode page, that user has three choices. You can also use like, link, fire, link, tree, some of those landing pages that can accomplish something similar. But, like, if I'm not a Spotify user, I'm not clicking on that.
B
Yeah, no, that. That makes sense. And I think with WordPress, the nice thing is that's like a reusable or recyclable block, so I could potentially just see, like, every so often, every two weeks, just go in, edit that one block. All my blog posts would then get updated with links to the latest episode. Yes. Yeah.
C
And you could also use something like. Like a fuse box that does something similar.
B
Okay.
C
You'd have to research some tools out there. I just.
B
Yeah. Some plugin.
C
Just. Yeah. Just keep in mind, just like, not everybody listens to Spotify and it looks nice, but there's probably just not a lot of people taking action there.
B
Yeah, totally fair. Okay. Okay, cool.
A
All right, Jesse, your funnel is actually already doing some remarkable work for you. I know we've talked about a few different ways that you could increase the visibility. Top of funnel. What are a few of your big takeaways here? Anything that you are looking at differently or you might change after this conversation.
B
Yeah, I think. Right. Honing in on that podcast guesting exercise. Maybe systematizing it a little bit more. Because. Because right now it is like a little passive background activity. It's like, oh, I've got some 30 minutes. I'm not doing anything. Let me go check my list of guesting and see who I need to follow up with. So trying to be more intentional with that, and trying to be more intentional with just like that, networking in the podcasting space and. And hoping that that will bear some fruit over the coming years. And then I think the second one is just being more intentional with my calls to action. I mean, I don't know if you guys are sports fans, but sometimes I think of this podcast as that, like that raw talent who has yet to be honed by a coach who actually knows what they're doing. And I feel like if I actually hone it, then there's really some potential there. And I think some of the ways I can hone it is maybe just being more specific about my ideal client, more specific about calls to action, and really trying to move people forward through the. Through the funnel.
A
Definitely. I think that's a really, really good recap. What I kind of jotted down here for your funnel and your action items are really straightforward. And, you know, your top of funnel for now looks like, you know, getting more systematic about show guesting. You know, potentially looking at ways to connect with other podcasters, either in person, podcast events, existing network, just being really thoughtful about how you connect with them and give value not in an exchange way, but a genuine, helpful way. So it's top of funnel for you. Middle of funnel is just your podcast content. I do think there's some opportunity there for you to get a little more clear on that avatar and refine that content just a little bit. Um, and then the bottom of the funnel is your sales process. So, as you mentioned, being more intentional with those calls to action, Taylor pointed out a couple really helpful things. You know, when you do guests on other shows being really classy in the way that you kind of, you know, mention your show, there are a few different ways for people to hear about it. And then in addition to that, being really thoughtful about not, you know, adding these other multiple channels. Like, sure, there's a few things you could probably squeeze a little bit out of, but really, this funnel is working. I think all channels are really difficult. Podcast has most. You know, the. The fact that the top of funnel visibility is really challenging, but the trust building and the surface time that you spend with someone is very unique. So this is a really beautiful platform. It's also a really challenging platform. And honestly, there's a lot of podcasters who also don't even have a middle of funnel or bottom funnel working. So you're. You're two thirds of the way there, man. So we're excited for you Please keep us updated and we just really appreciate you coming on the show, sharing your download numbers, your traffic numbers, all those pieces. We really appreciate it.
B
No, thank you guys so much. This was very helpful for me too and looking forward to more awesome episodes. Thank you guys for putting the show on awesome.
A
Thanks so much for joining us. We hope you enjoyed today's episode to get the resources shared or sign up to join us as a guest on one of our advice line episodes. Check out other links in the show notes. Thanks for listening and we'll see you next week.
Episode: Advice Line: How to Grow A Podcast That’s Already Converting (Jesse Cramer)
Hosts: Taylor Schulte & Kendra Wright
Guest: Jesse Cramer (Cobblestone Capital Advisors, Best Interest blog, Personal Finance for Long Term Investors podcast)
Release: September 3, 2025
This Advice Line episode addresses a common, but high-quality problem: How can a financial advisor with a successful, client-converting podcast expand their reach and grow their audience even further? Jesse Cramer, who already oversees ~$80M in client assets and manages a podcast pulling in over 12,000 downloads per month, seeks the hosts’ input on two fronts: fueling the top-of-funnel (audience growth) and systematically leveraging his media ecosystem to drive more business. Taylor and Kendra deliver tactics for focused top-of-funnel marketing, networking, competitive positioning, and actionable “next steps” — especially tailored for advisors ready to ramp up rather than start from zero.
On Differentiating the Audience:
“Whereas maybe the more mom and pop style that I talk about is someone who says, I know I have to save, and I’ve saved for 40 years, and now I’ve got this $3 million nest egg. When you say Roth conversion, I don’t know what you mean. … Whereas the hardcore DIYers, they know what those things are.”
— Jesse (03:25)
On Client Motivations:
“Do I have enough to pull the trigger today? Can you help me feel more confident that I’ll never run out of money? …I just know (the tax issue is) lurking out there.”
— Jesse (06:00)
On Guesting Effectiveness:
“I’d argue that’s probably the most effective way to grow the show. The hard part is getting onto the show and getting onto a show where your ideal client lives.”
— Taylor (17:58)
On Building Networking Momentum:
“It’s not just like building the relationship with a journalist, but it’s like, they have a job to do and how can I help them? How can I make their job even easier?”
— Taylor (28:29)
On Owning What You Create:
“If I just focus on creating really high-quality content... who cares what else they go and listen to? They’re always going to come back and listen to my show because I put so much time and energy into it.”
— Taylor (31:06)
Top of Funnel:
Middle of Funnel:
Bottom of Funnel:
Jesse’s “problem” is a blessing: his content and funnel convert, but visibility is the bottleneck. The keys are focus, systematization, and relationship-building—especially via guesting on other relevant shows, cross-promotion, and targeted networking. Don’t dilute the funnel with misaligned audiences; concentrate on the pockets where your future fans (and clients) already pay attention.
“Your funnel is actually already doing some remarkable work for you... This is a really beautiful platform. It’s also a really challenging platform. And honestly, there’s a lot of podcasters who … don’t even have a middle of funnel or bottom funnel working. So you’re two-thirds of the way there, man.”
— Kendra (40:59)
For financial advisors with podcasts: If you’ve solved conversion, it’s time to invest discipline and creativity in top-of-funnel growth—with a mindset of giving, connecting, and constant refinement.