Advice Line: How to Grow A Podcast That’s Already Converting (Jesse Cramer)
42m 12s
Jesse, a financial advisor and podcast host, identifies three key client archetypes: complex-income professionals, pre-retirees with significant assets, and highly educated DIYers who consume financial content but lack confidence in executing strategies. His podcast, with 12,000 monthly downloads, serves as a strong middle-of-funnel asset, converting primarily mom-and-pop retirees and DIYers through educational, relatable content. He emphasizes that his audience is already somewhat educated, and their pain points—like tax uncertainty and retirement planning confusion—are central to his messaging. To grow his top-of-funnel visibility, Jesse strategically guests on retirement-focused podcasts, weaving in references to his show in a subtle, value-driven way. He also invests in network-building through in-person events, existing connections, and genuine value-sharing, avoiding transactional outreach. His content is refined to address real, urgent issues such as tax planning and decumulation, making it accessible without oversimplifying. Despite the challenges of podcast discovery, Jesse believes consistent, high-quality content creates trust and naturally drives conversions. He plans to systematize his guest appearances, improve call-to-actions, and deepen content alignment with his ideal client persona—proving that a well-structured funnel, especially with strong trust-building, can drive sustainable growth even in a competitive space.
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. In Jesse, he's been in the
industry for four. The firm manages around three 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? 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 to you guys on how
to focus and improve on that. 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 or trying to attract with the show?
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 to 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 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 it's hardcore DIYers. People who say I never thought I would
hire an advisor, but my life has now changed or but I realize 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
positions to to work with those kind of people. Okay, and when you're thinking about the pre-retire
three five years out, what's your asset minimum? Technically speaking 500,000, but in reality it's more
like 1.5 million. And one 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? It's someone with more of a unique complex income structure. Yeah, so
what that might mean it might be 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. 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? It for sure. It's the fact that almost all my content is geared towards the
latter two in mines. 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 100% those are the people
who are converting. Can you pick me a little bit of a difference in the contrast? You know,
because a DIYer could be five years from retirement, what do you see between those two?
Yeah, I think maybe just the differentiator in my mind is that simply that idea of I never thought
I would hire an advisor. I've met with advisors before and I felt like I knew more than them.
I consume so much of this kind of content. Maybe that's one of the big ones 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 Irma,
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? 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 DIYer?
Yeah, in terms of people who have actually come forward and now are working with me as clients.
Yeah, like 50% are the mom and pop, 50% of DIYers or some of their configuration.
Probably two thirds to three quarters are the mom and pop, and then the last third or quarter
would be the hardcore DIYer. Okay. If you were to narrow down on one of these to really start to
build this podcast for one of them, is there one that speaks to you more than the other?
I just think they're probably for a few 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, 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
you, 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. My question will probably be
which way is the most enjoyable way to build your business? Yeah. No, that's a good question.
I think it's going to be working with mom and pop. Yeah.
No, with that particular segment of those five years out with at least 500K, ideally 1.5 or more,
what a couple of those big pain points, you know, painful, urgent, expensive problems there,
willing to pay you to solve. Like, you see those coming up big themes.
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 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. Okay. Awesome. So let's talk a little bit about your actual funnel.
So with your podcast right now, middle funnel is working pretty well. What kind of downloads are
you doing monthly? As we record this in July, it's going to be an all-time high month right now.
I'm at about 12,000 for the month with a week left. Awesome. Okay. And for the actual podcast,
what kind of calls to action do you have, if any? Yeah. A few different ones. Some subtle.
Some 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 core 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 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 schedule a call. I don't quite go that far, but I just I move them kind of down the funnel.
How many people do you have in your email list right now? 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.
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 does it seem like the podcast calls to action are converting?
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 they're 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. That's a manual form, right? Correct.
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? Correct. 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. Okay. Gotcha. That's really helpful. And as far as you know,
the content roadmap, how are you choosing the topics you're putting on the show? A lot of it is
listener-inspired at this point, which I've 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 and the questions that I'm getting. And it's just so
natural. Like, okay, if my retiree audience wants to learn about XYZ, 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.
Absolutely. That makes sense. What have you found so far to be effective for growing the
show? Like, what have you tried and what's worked specifically for growing the show? Probably
two main things. One is podcast casting. 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 it kind of like in any permutation you can think of, I've tried to get these pointers
from one content to the other. What's your monthly website traffic look like? Kind of
all park wise. Probably about 20,000 visitors a month. Okay. Awesome. A lot of good stuff
to work with Taylor. What's coming up for you? Yeah. I mean, Jess, 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 poor gasoline on the fire here. One
maybe clarification I want to make here. And if you're free to disagree, because I'm just
kind of thinking about this on the spot, you're talking about this like mom and pop investor
versus DIYers. I don't even think about that. Like I would argue that if you're hosting
a finance podcast, and we were talking before I 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 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 educated. It's
hard for me to believe 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? They've
heard of it. They've heard of it. And that's 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,
if 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 convergence 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. I think that's a really good example. Like when
I think of mom and pop investors, 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. Yes, there's
a variety of listeners, some who like, I know all the stuff. I know I could do it on my
own. But Jesse, I don't really feel like doing it on my own or 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 set something in your show. Like I didn't know about that thing. I don't really
want to figure it out on my own. I can't figure it out 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 just don't
really think too much about mom and pop investors versus DIY. It's just in my mind.
They're all, they're all DIY. They're all people that are out there trying to learn
the stuff on their own. And there's a tiny percentage of our audiences that just raise
their hand and say, 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 this great podcast, 12,000 listens a month and growing. 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, we're 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? That in and of itself can be a bit of a slog, but the method 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, 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 up there about lifestyle for retirees? They have nothing to do with
money. 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 hear all the things I will talk
about, hear the kind of things like questions I'll 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. How often are you guessing another podcast
or how many other shows have you, have you guessed it on? I've got one that's recurring.
That's pretty nice because it's a reasonably big show and probably like twice a month.
I'm one of their guests on their Friday episodes. Is that stacking Benjamin stacking
Benjamin's yeah, exactly, exactly. And then outside of that, there've probably been maybe
like two, a quarter for the last couple of years. Some big and some very small. Okay.
Is this a path that you want to go down? Do you want to build a better system process
to guest on more shows or are you thinking of other top of final activities?
I mean, it, yeah, I mean, it's certainly with, it's not something I'm opposed to and
I enjoy guessing 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 on
to 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.
There's a lot to unpack there. Yeah. Maybe I'll start with your comment saying, you know,
I'm not sure if guessing on other shows is very effective. I'd argue that's probably the most
effective way to grow the show. The hard part is getting on to the show and getting on to a show
where your ideal client lives. I'm good friends with a 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 on to those shows where your ideal client does live and then
positioning yourself properly on those shows. Like I like the idea of guessing 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 shows might be a little bit different. Probably not
going to get into the weeds of like Roth conversions and pairing them with donor advice 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 you 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 another 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 the audience to your show. So 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? It's a very specific topic
that I'm going to talk about. So I'll say things like, you know, just the other week on the
state 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. It's like overly promotional.
I was like, "Oh yeah, we actually talked about that
"the other day or I had this guest on my podcast
"as Stay Wall Street Retirement Show."
And I'm gonna weave that in.
And every time I do this intentionally,
I see a pretty large uptick in listeners on my end.
It has been a really effective way to grow.
But yeah, the challenges 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 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 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, sort of hiring them
in agency, which would be really expensive.
But I do think it's really effective.
- Did you find Taylor 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.
- I haven't really been presented
with that opportunity where smaller shows
or reaching out to me, like, please come on my show.
I definitely want there to be some momentum there
and not like, I just started my show.
Come on it, if it was a friend,
I'd probably find a way to support them.
But yeah, I don't know, 'cause 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.
- Yeah, 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, 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 large or small that show might be.
- Well, they 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 as,
how do I add value to that person and build a relationship?
And really see 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 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 out, but a mastermind
or even just a 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.
Like how do I actually really help these people
and give them something that I would also want?
And 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 a systematic kind 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?
We then like a gentle nod to your show.
And then at the end of the show, maybe you have like,
you know, a strong call to action to show,
or you have a different offer.
So 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.
Yeah, yeah, that's interesting.
And I will share with you guys and the audience too.
Like, I probably have a series of 10
or 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 you can do your 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 created a new lead magnet that's been like more successful
than every other lead magnet I put together combined.
So that's one I need to start adding in more too.
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 Britholz.
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,
CMBC, 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 a really interesting idea.
- 'Cause really, 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 thoughtfully and you're clear
on 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 convert to a call.
- Yeah, yeah, exactly, exactly.
I think I'm sure you get this to 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'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, right?"
And now it's just about, right,
how can I get more versions of that person
and the answers is top of funnel exercises?
- Yeah, yeah.
- I heard what Kendra said a little bit differently.
I don't have 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.
She's intentional about it, she knows what she's doing.
This isn't just by accident,
but she is really honest and authentic about it
without expecting anything in return,
but also knowing in return,
she's gonna have some great relationships really
that she can potentially benefit from
leaning 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 show.
They're probably listening to Roger show.
So, 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 podcasts 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.
And 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 10 best retirement podcasts
or finance podcasts that I love.
And like, you know, you throw Roger's name
and there and you throw Ben's name
and 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 Bolton 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 Bolton and you go to Steve.
No, okay, Steve, by the way, I just wrote this article,
you know, I get X amount of, you know, visitors per month
that I wrote this article.
I highlighted you guys like, hope it helps.
Like, that's it.
And you started 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 up this from an angle of helping them out.
I think this is what Josh Brown did really good.
It's like, it's not just like building their 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.
It gets a lot of 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 on as a result of a cold email
that I sent Joe at four 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.
It was a shot in the dark, but here's what happened.
It literally resolved this morning.
And I just want to share it with your audience
and try to help them.
And he responded, had me in a show like,
so it's like a cool story 'cause they love it.
love saying, you know, talking about cool stories
and something applicable to their 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.
- Right.
- Like share my thing.
It's like, I know that your audience has this issue
and I've got a solution for it.
- Yeah.
- Yeah.
- Lots of impact there.
- Totally.
But like, you know, I don't know if you guys have read
the go-giver or if you've heard of the idea before,
like the go-giver.
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 use the term before,
almost that scarcity mindset of just like,
I get it.
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 a 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, my head is like,
well, if you just 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 yeah, I appreciate you guys sharing those ideas
'cause I have to do better to internalize your advice.
- Yeah, I get it.
My head goes there as well.
And what I often fall back on in,
and this is somewhat egotistical comment.
I believe it 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 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
and 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 gonna come back and listen to my show
because I put so much time and energy into it,
but I hear you, it is tough.
- Yeah, yeah, yeah, go ahead.
- Oh, a question for you, Taylor.
And Kendra, I mean, you might have experienced with this,
but do you have any thoughts on
when it comes to podcast gusting
that a lot of the financial podcasts out there,
if they're really, you know,
it's their targeting towards FI,
the financial dependence 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, Fran.
Kendra.
- A better question is, are they a good client for you,
even if they liked hearing from you?
You know, is a fire audience going to be, you know,
those kinds of people, are you gonna be excited
to get on a call with them?
Are they gonna be aligned with the problems
that you're excited to serve?
So I do see it there, there could be that bias for sure.
But I've seen a lot of my clients who specifically tell me,
I actually don't want those kinds of clients.
So instead of asking whether audience like me,
I first asked what I like working with their audience.
You know, and then we can consider the bias,
but I think like, you know, if that personality fit
isn't functioning with who you're excited to serve,
like that's not a good audience for you.
- Yeah, no, I, okay, I like that answer.
'Cause 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 we'll 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 tailor 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 gonna reach out to us in the first place,
have you ever tried to leverage them as COIs
in their little friend groups and 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
or I hope you'll reach out to me,
is that an avenue that you think would work?
I think it could work if it was positioned properly.
I mean, it's a pretty passive call to action
near 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, listen to this guy every week on his 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.
Like, I'd probably put a little bit more thought into it.
Like, how can we try to squeeze as much juice
out of the call to action as we can?
But I haven't done anything directly to those people.
It's like, I just assume Jesse,
you're talking about these other podcasts,
maybe anti-advisory, anti-fee models,
like, who their audience is.
One, want to make sure like the audience meets
my general criteria, high net worth,
pre-retire, retiree, older demographic.
Like, as long as it needs that criteria,
I don't really care what their philosophy is
around advisors or paying anybody
or what the hosts beliefs are.
Like, that doesn't really matter to me.
I assume that 99% of my audience
never gonna hire me anyways.
Like, that they don't want to pay an advisor.
Otherwise, my firm would be $20 billion.
So, I don't know.
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 get people in a 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 taken on clients.
So, there doesn't even be a strong call to action.
Before we run out of time here,
I just wanna 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 find ways to include that in your email signature
or weave it in the conversations
or maybe they're on 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.
It doesn't normally listen to podcasts.
Like, if they're listening to personal finance
podcast and retirement podcasts, chances are
they've already subscribed to your show.
So, I think it's potentially okay
from a credibility standpoint,
but I don't think it's gonna be a huge needle mover.
The other thing I wanted to bring up
before we ran out of time was you had mentioned,
hey, and 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
'cause I listened to my podcast on Spotify,
but 75% of people listened to it on Apple.
And so, what I pivoted to is I just include a link
to Apple, Spotify, and YouTube,
but specifically for that episode.
So, the little bit of manual worked out that my VA does,
but for every episode page,
that user has three choices.
You can also use link fire, link tree,
some of those landing pages
that can accomplish something similar,
but if I'm not a Spotify user, I'm not clicking on that.
Yeah, no, 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, and you could also use something like a fuse box
that does something similar.
Okay, you'd have to research some tools out there.
I just, yeah, some plug in, 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.
Yeah, totally fair.
Okay, cool.
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?
Yeah, I think, right, honing in on that podcast,
guesting, exercise, maybe systematizing it
a little bit more, 'cause right now,
it is like a little passive background activity.
It's like, oh, I've got 30 minutes.
I'm not doing anything.
Let me go check my list of casting
and see who I need to follow up with.
So try to be more intentional with that,
and try to be more intentional
with just like that networking in the podcasting space,
and hoping 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 raw talent who is yet to be honed
by a coach who actually knows what they're doing.
And I feel like if I actually hon 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 funnel.
Definitely.
I think that's a really, really good recap.
what I kind of drawed it down here.
for your funnel and your action items are really straightforward.
You know, your top of funnel for now looks like, you know, getting
more systematic about show-gesting, 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, this 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.
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 guest and 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.
Podcasts is most, you know, 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 are a lot of podcasters who also don't even have a middle of funnel
or bottom funnel working.
So, 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.
No, thank you guys so much.
This was very helpful to me too.
And looking forward to more awesome episodes.
Thank you guys for putting the show on.
Awesome.
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 the links in the show notes.
Thanks for listening and we'll see you next week.
Podcast Summary
Key Points:
Jesse focuses on three client archetypes
His middle-of-funnel podcast content is highly effective, with 12,000 monthly downloads and strong engagement (75% open, 20% click rates), primarily converting mom-and-pop retirees and DIYers.
He identifies a key distinction between DIYers (who know financial terms but struggle to apply them) and pre-retirees (who need education on concepts like Roth conversions and tax planning).
Jesse has improved his funnel by weaving podcast mentions into blog posts and newsletters, using subtle call-to-actions to guide listeners through the funnel without direct pressure.
He strategically guests on podcasts with overlapping audiences, focusing on retirement-focused shows where he can naturally reference his content and build visibility without being transactional.
His top-of-funnel growth strategy includes intentional networking, in-person events, and value-based outreach to podcasters, emphasizing authentic relationships over direct conversion.
He is refining his content to better serve his ideal clients by aligning topics with real pain points—like tax uncertainty and retirement planning—while avoiding overly technical jargon.
Jesse recognizes that while podcast growth is slow, consistent, high-quality content that speaks directly to audience needs builds trust and naturally drives conversions over time.
Summary:
Jesse, a financial advisor and podcast host, identifies three key client archetypes: complex-income professionals, pre-retirees with significant assets, and highly educated DIYers who consume financial content but lack confidence in executing strategies. His podcast, with 12,000 monthly downloads, serves as a strong middle-of-funnel asset, converting primarily mom-and-pop retirees and DIYers through educational, relatable content. He emphasizes that his audience is already somewhat educated, and their pain points—like tax uncertainty and retirement planning confusion—are central to his messaging.
To grow his top-of-funnel visibility, Jesse strategically guests on retirement-focused podcasts, weaving in references to his show in a subtle, value-driven way. He also invests in network-building through in-person events, existing connections, and genuine value-sharing, avoiding transactional outreach. His content is refined to address real, urgent issues such as tax planning and decumulation, making it accessible without oversimplifying.
Despite the challenges of podcast discovery, Jesse believes consistent, high-quality content creates trust and naturally drives conversions. He plans to systematize his guest appearances, improve call-to-actions, and deepen content alignment with his ideal client persona—proving that a well-structured funnel, especially with strong trust-building, can drive sustainable growth even in a competitive space.
FAQs
Jesse targets three client archetypes: Type A business owners or executives with complex income structures, mom-and-pop investors five years or less from retirement, and hardcore DIYers who say they never thought they would hire an advisor but now realize they need financial support.
Mom-and-pop retirees often lack familiarity with financial terms like Roth conversions and are seeking help due to uncertainty about retirement planning. DIYers, on the other hand, know these terms and may have tried to manage finances independently but lack confidence in executing complex strategies.
Jesse is averaging around 12,000 podcast downloads per month, with 4,000 email subscribers who have an average open rate of 75% and click rate of 20%.
Jesse uses subtle cues like sharing client stories or behind-the-scenes insights to build trust, and includes direct calls to action such as subscribing to his weekly newsletter or listening to specific episodes that highlight his financial planning practice.
Jesse strategically guests on podcasts with audiences aligned to his ideal clients, such as retirement-focused or lifestyle shows, and weaves in references to his own podcast to drive traffic. He also emphasizes genuine value and relationship-building rather than overt promotion.
Jesse’s content is listener-inspired, with frequent questions from his audience shaping episode topics. He especially values AMA episodes, where detailed listener questions lead to high engagement and reveal recurring pain points in retirement planning.
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