Listen To The Podcast
We talked with Sydney about:
- Advice for individuals or companies considering starting a podcast
- The importance of creating a detailed process and workflow
- The tools she and her team use throughout the process to create first-rate content
Kitces.com is considered one of the top “go-to” resources for financial advisors and is known for its relevant and engaging articles and podcasts. As managing editor, Sydney Squires gives insight into the processes it’s developed to be able to consistently roll out high-quality, integrated content across platforms.
- “Why Asana?”
- “How to Start a Podcast” with Libsyn
- “Why Coast?”
- Kitces.com Facebook
- Kitces.com Twitter
- Kitces.com LinkedIn
- Kitces.com YouTube channel
- Financial Advisor Success Podcast
- Apply or recommend a guest for the podcast
To learn more about our On Purpose guest, please visit Sydney’s LinkedIn page.
Full Audio Transcript
All right. Well, Sydney, thank you so much for joining us. We have been anxious to hear a little bit of background about the Kitces podcast and all that you all are doing. So why don't we just dive right in. I'd love just to hear about your experience and how did you get to where you are today?
Yeah, absolutely. Lauren, thank you so much for having me on board. So my process to Kitces is a little bit funny because I did not come with a financial planning background, which is what the whole company is focused on, making educational content for financial planners. I actually started out my career working in child publishing. I worked originally in educational curriculum, making a lot of content starting off with homeschooling programs and jumping into the print magazine side of it. I had a ton of fun. I have a lot of respect and love for print publishing, but especially for children's publishing, because it requires kind of those iterations on being really clever and being cute and fun. And you wanna be engaging, but not condescending and empowering. And it was a really great place to start off.
So the homeschooling company that I started at experienced a ton of growth in a really short amount of time and they needed managing editors to just kind of help fill slots, coordinate all the projects. So that was what I started doing fairly early on, just working with all of the other editors that had been hired as contractors and just sending things their way, helping to give feedback. That ended up being really positive. I started working a little bit more on the journalism side, on the app and media, production scheduling side. And then I kind of ended up landing at Kitces, at kitces.com. It was a funny way where COVID obviously just makes new plans for everyone, but so now I'm managing editor here.
I handle all of our front-facing engagement, which is basically all of our free stuff, which is a lot. That's three, 3,000-plus word articles that we run every Monday, Wednesday, and Friday; that's a podcast every Tuesday; and then a second podcast every other Thursday on top of social media management and all of that. And then I manage an awesome team of writers, editors, podcast producers, graphic designers, who obviously help me with all of that. So it's a great team and we definitely keep ourselves busy.
It's incredible. I know before we were talking and I was sharing that there've been so many individuals that I've talked with that are just in awe about the amount of content, but it's not just about content, but how rich it is. And how much value you're putting out there. And every piece is so thoughtful and I can personally share that having worked together, going back and forth on an article, it's a lot of work, but things that look easy usually aren't easy, right? So this is what we're excited to get into today. I know there's so much content that you're covering and the focus today will really be on the podcast. And I know that is new in the world of kitces.com, all things relative. And so why did you decide to start a podcast? I mean, I heard there was some chatter about possibly starting one, it seems like there was kind of maybe crowdsourcing or interest in that, but what was a trigger for you all? And how did you get the ball rolling?
Yeah, so that's a really good question. I think it kind of started from two things. We're a very data-oriented company. So I think there was a certain degree of like, a lot of people are doing podcasts, they're having a lot of success with their podcasts. And so on. I think that a second aspect is that Michael's brain never stops running. I think that if Michael had it his way and I was also twice as smart, we would have like 800 new things going live on the blog all the time. Fortunately, he works with my limitations there most of the time. But I think the kind of ironic thing with choosing to jump into the podcast was financial advisory success was started in 2017. At that point we were like, podcasting had gotten big like five years before that.
So relative to the whole industry we were really late to the game, so at that point it was pretty easy to look and point and start to realize like, oh, people have had a lot of success with it. And the actual mechanism to trigger it was literally Michael just pulling together a list of his friends and starting to just iterate, you know? And I don't think until you really get in there that you can figure out if it's something that's sustainable or feels natural or something like that, like you can flush out like the process side and start to figure out all the stuff that you would like to have. But until you jump in and you start to figure out what those conversations actually feel like, then it's just kind of the idea.
That's so fair, it's sort of this ivory tower idea. You can idea around it, then how does it actually come to fruition? And how do you get down to the heart of the conversation and how, as you moved through the podcasting world and we're figuring out what was working and what wasn't, how have you helped to manage that as part of the greater content strategy? You know, this is one element and how are you balancing that content with everything that you all have going on?
Yeah, so I mean literally, I joke that keeping the calendar running is my full-time job. That's just like 40 hours a week that I am sitting in there trying to figure out all those moving mechanisms. So one of the things that really helps is we track all of our articles and all of our podcasts in the same system. So that helps to give a really good overarching view. I sit down with the podcast producer and we talk and we can see the list of all the upcoming articles. We know who's already been there as a podcast guest. We try to do some sorting by topic, trying to complement each other. And one of the things that we've been trying to do increasingly is not to let things exist in a void, cuz sometimes you get a really great podcast guest and they're awesome.
And then like three years later they send us a note like, Hey, I would also like to write for the blog. Here's an outline. And we're like, oh my gosh, we missed out on three years of potential content with this person, you know? So I think that to kind of expand a little further on where I'm going with that, to me, one of the most important things with making sure that the articles and the podcast talk to each other and that everything flows well is to be always iterating on the podcast, or sorry, to be always iterating on the process. Just three days ago, we made a change to the podcast that’s been running for five years, to the process there, and it's something that's probably going to save us four or five hours a time.
Every week, you know? I think it can be really easy to just let things sit, you know? And to me that's another important part of just talking and making sure that everything gets coordinated because it's a lot of the same people doing the same stuff, you know? And so unless you are looking at it, not just from a content, but also from a process perspective, you might align one really well, but if the other's not also aligned, you can end up in trouble really quickly.
So you mentioned having it all in one kind of calendar. What system are you all using to see that? Is it simple as an Excel doc?
No, we work in Asana.
We love Asana. Awesome. It's so great.
Yeah. So we have our editorial calendar, which shows every single step for every single article that we have broken out. And then I have a podcasting production calendar because all of the steps for that are completely different. And so then I have all of the podcasts on their links, so they show up on the calendar. So literally anyone can check at any time, even if they're not directly involved with the podcast or the articles. The whole, our overarching view, is clear both to people within our team and people outside of it. Okay. That's really fun. That's the best part. Do you wanna just talk about Asana for the rest of the podcast? I know the automations I've made.
It’s great. Yes. I know there's so many features. It's pretty amazing. We're totally Asana geeks over here too. So it sounds like you have the separate projects, if you will, inside of there for podcasts versus content or other.
Yeah. So they exist on separate projects and each task is one podcast and so I make it set the tasks also populate on the article one because the article one is a center one.
Got it. Okay, so Asana to be able to see the overarching calendar and then also to do the workflow, project management of all that's going on, and then are you all actually scheduling out the content or like when it goes live, are you natively putting it up on social media? How are you managing that side of things?
Yeah. So there are a couple of programs that we use. So Libsyn is the one that we use for the actual distribution, that shows up in iTunes or whatever. And then we use CoSchedule to do all of the social media.
I know CoSchedule too.
I like CoSchedule. It is really awesome in a lot of ways. I also have many stories about the wrestling that we've done with it.
That's fair. It's got a lot of bells and whistles in there, you know. We have found
that they're not all needed at least for us.
Yeah. I feel like CoSchedule is one of those things where I'm like, I think if I was smarter, I think I would love CoSchedule, but I'm not quite smart enough to enjoy it as much as I should.
Okay. So, there's an element of live posting and then also scheduling out content as well.
Yeah. Well, and I should also be more specific where we have a third-party group, Cashflow Podcasting, that we work with and they're the ones who actually do all the scheduling and they upload the show notes that you see. Which is great because I hopped in there once to try to make some edits and nearly broke everything. So I'm really happy to let them do that side of things.
Yeah. That's fair, to have trusted partners, there's a lot of parts and pieces, which is pretty incredible. So just to back up a little bit, so we could talk a little bit about the planning that goes into it. Kind of the calendaring, the project management internally, and then we talked a little about the end part, right? When it actually goes live, what's kind of that middle part? So once you've identified a guest, which actually I'd love to know how you are identifying guests, that's a question, but then once you've identified them, what's the pre-podcast and post-podcast communications like for that guest? So maybe we'll start with how you identify and then go through that workflow?
Sure. Yeah. So I guess actually, I might even start a little bit of a step before that, because I think the guests that we choose are really guided by the goal that the podcast has. So the simplest way to explain the goal of it is just to highlight success stories in the industry. These are people who went out, they started their own business in an industry that's really hard to get started and they made it, but then more specifically within that, we also try to highlight that success doesn't look the same for everyone’ everyone has a different metric, regardless of what the metric is. It's really easy to look and be like, wow, like this person's firm is so amazing and not realize that it's been really hard, you know?
So for selecting a guest, like I mentioned, the podcast guest list literally starts out with Michael's friends in the industry; nowadays, we kind of choose from all over. We have a place on our website where advisors can submit themselves or people that they think would be great fits for the podcast. We check out awards lists. When I went to the XYPNLIVE conference last October, I think I found two or three podcast guests that I was more or less secretly sleuthing for. But the reason that we look in so many places is because what we're really looking for is less of the person and more of the story, you know? And if you're only looking in one place, you miss out on like this whole spectrum inside of stories, cuz every spot has its blind spot.
So what we really do is look for someone who has achieved success, no matter what that looks like. We have interviewed consultants, people who have started their own firms and are making millions, people who have started their own firms and are making like a hundred thousand a year, people who have enterprise-level firms, people who are just solo, you know? Everyone has a really unique thing that kind of led them on their path to success. Like whether they have a unique business structure or a niche that is just bonkers. We interviewed someone when I first joined that was specialized in being a financial advisor for competitive fishermen, I think.
So specific, so niche.
I know. And, I guess there's enough of them that you can make a living off of that. Interesting. You know? But, they all have their unique story and it's really that story and that hook that we look for more than the metric of success.
Yes. That makes sense. Yeah. Are you each individually reaching out to them then or how is that coming about?
So we have a meeting with Michael where we kind of talk through to people that we would like to feature on the podcast, get them greenlit or we could ask to bring in more information, all of that. And then after that, we usually just send them the invite. At that point, we've pulled up like their ADV, so we know how big their firm is and how much they’re making, we've looked at their website, we've done the basic amount of stuff to be sure it's a real person and not someone who's pretending to be a financial advisor or anything like that. But then, yeah, we literally just shoot them the email and set up the initial call.
And then what's the lead time? I guess the lead up? You have your conversation and then how does that go? I know for example with the article, there was a lot of lead-up work and then it was four weeks, six weeks, eight weeks sometimes out before things go live. So I'd be curious of what that timeline is like for you all, and how do you communicate with those individuals once you've got them on the books?
Yeah. So there's kind of two sides where the podcast has a little bit bigger of a buffer because we're trying to schedule the actual recording. So several weeks in advance, people will usually get on the calendar just to record about a month, ideally, in advance, three or four weeks. And then after it's recorded, it's usually four to eight weeks until they go live. We try not to let it run much longer than that because people do get so excited about being on the podcast. So then it kind of sucks if you're like languishing for months afterwards, you know? So that's weird. But on the prep side for that, our podcast producer reaches out, they do a whole prescreening, always send them a swag box that has the headset that they need, and everything like that. So we do a whole let's look and make sure that all of your technology works, which thankfully, since I've been here has not been a big deal to check that. And then once we get their technology squared, she runs them through a few practice questions and kind of creates an interview note checklist for Michael and then they're just clear until their recording date.
And then do you have, I mean, just with all the compliance regulations and this and that, do folks sign off on something ahead of time? Is it edited? How does that all work?
So I guess I'll say that for probably about 98% of people that we have on the podcast, what they say on the podcast, we may edit things down to be the length of time that we need. Like sometimes Michael has recorded for two hours and we need to be 90 minutes. So then we end up chopping a lot. But other than that, we have run into actually very few issues with compliance. We've had a few times where we've had to edit out. Michael asked a question and they're like, we actually don't feel good about saying that in front of tens of thousands of people. And then we just cut that question, like it was never asked. So that has a really friendly way of kind of helping to screen itself to make sure that people who are caught in compliance web can kind of filter out what they're comfortable with. And then every now and then we have someone who records ask if we can send it to them in advance to be checked by their compliance team, but out of the 270-plus episodes, to my knowledge that's happened like five times.
So at least in our experience, if it's live, it's a little different than if it's written, but these things are always changing and you get different advice from different folks. And so that's fair.
And then I think a key aspect that also helps is I think at this point when a lot of people come onto the podcast, they know what they're in for, which is Michael will ask them very in-depth questions about them and their firms. So there's probably a certain degree of self-selection they're going on as well, where the people who agree and show up are the ones who are really comfortable with being really transparent, which really helps.
That's fair. Yeah. And they've seen others lead the way too. You said 270 something.
It’s something like that. I don't know what's live right at this moment, but I think that we have 278 episodes recorded.
Holy smokes. That's a lot of work. And then, you mentioned the thousands of listeners, right? How did you get there? Obviously there's a base that you all had worked with, right? It's not like starting a podcast from scratch or publication from scratch. This has been in the works, but how have you promoted this? How do you keep promoting this, and kind of fueling the Google engine, if you will, and making sure you're adding valuable content. I'd love just to hear about that promotions plan, once you do go live.
Yeah. So there are a few things that honestly really help us. Ironically, the first one is that we publish our full 90-minute transcripts with our podcasts, which means that we have a ton of SEO-friendly headers and keywords and all of that, that kind of help people who are searching for it. Another aspect that helps is whenever we feature a big guest on the podcast, we get a huge jump in listeners and then the spike never fully comes back down. So, you know, I'm sure that you'll get a spike with me. I'm known and respected by tens of people. So that's the help that I will give. But I remember that when we interviewed Matthew Jarvis, who was really big in the financial planning industry, he gave us a spike where I think it was the first time that we broke 10,000 downloads on a single episode.
And then it did go down below 10,000 again, but it stayed probably 2,000 higher than it had been previously for weeks afterwards. We found really consistently that if we can get people excited about being featured on the podcast and if we can give them tools to share and to promote it themselves and even just communicate that we're excited that they were on the podcast with us—it's a process and a little nerve-wracking to sit there and get interrogated for like two hours, you know? That has almost become our best promotional strategy.
Yeah. Building that community. And being able to share that content, arming people, it sounds like, with the tools to be able to help promote it too. Then I'd be curious, you talked a lot about the data, right? Like all the data that's coming in, and it seems like that's not just something you're looking at with the podcast, but with the content platform at large. How often are you looking at that data coming in? I know you said you sit down with Michael, you go through the calendar and what's going on, what's working, not working, et cetera. Are you taking in those lessons learned, but what are you looking for? And are you just looking at Google analytics? Are you looking in the back end of your podcast platform? What are some of those key indicators to know if you're on target with your objectives?
Yeah. So our data lives in a ton of different spots. The primary one that we use for what's actually going live on the site is Google Analytics. If Asana is my first home, then Google Analytics is my second. Every single week, I'm in there and I input all the data from how people got there, how many people got there, whether or not it was SEO friendly. I don't know if your guys' site has been affected by this, but Google decided to mess with analytics twice in December and our organic search traffic tanked, and now we're making our recovery. The place where we look specifically for our podcasting data is on Libsyn, and so that will store a lot of the geographical data for the listeners, how many, for each episode. I feel like I might be freaking people out a little with how much we can track; just know that it's everyone and not just us.
So then we can really identify how many people are on the site versus just streaming it. Because if we were just looking at site numbers for podcasts, we probably would've shut it down a long time ago. That also helps us really identify when a podcast guest does phenomenally well. And then we start to look at, was this someone really well known in the industry? We had someone who got a ton of downloads because their topic was so controversial that they started a fight in our Facebook comments section, and then everyone clicked through to view it and listened to the whole thing and then came back and argued more, so it was seen by everyone. Hard to predict, but a neat thing. Like I keep saying, we need you to make some fake accounts and just start starting fights on Facebook, you know? Cause apparently that's the key to the success that we should actually be chasing.
Well, people wanna know what's going on. Right. You get a little look, and then are able to dig a little deeper.
And then when they click through and they see that it's a 90-minute thing and they're dedicated enough that they either read that whole 20,000-plus word transcript or listen to the whole thing and then get back and argue. That's when you know you've got a fanbase that cares, you know?
Yeah. Now I think one of the things—we were talking about this a little bit earlier—but you've got so much content. There's a lot to produce, but there's so much substance to it. And do you think that because you took the leap to be able to start this podcast, did you feel that, and do you feel that the financial services space or even within the wealth management RIA space needs more podcasts or is it more the objective that it's another platform to add more content that's of substance? What do you see out there when you look at other content platforms within the space and where do you see the gaps?
Yeah, that's a great question. So, and I'll admit that I'm a little bit biased in my answer because as it's probably clear at this point, I'm a very story-oriented person. So the perspective that I kind of lead with first of all, is that there's absolutely room for whatever the story is that the person has, whatever their platform needs to be to share that and I wouldn't want anyone to shy away from at least trying to get their voice out there because they feel like everything is oversaturated. I find that people really underestimate what makes them unique because like I have to live with myself 365 days a year. So in my mind I'm a pretty average person, but I did mention the tens of people who respect me, and who see the thing that's unique in me, hopefully, you know?
And so I think that's a really important thing. The second and perhaps a little bit more analytical angle I'll add is that there are always gaps that haven't been filled yet. Financial advisory success is a really great example, because a lot of advisors make podcasts that are aimed at their clients where it's very educationally focused and very much like, finance 101, kind of talking through and showing their expertise. I can talk with you about budgeting. I can talk with you about recessions. I can talk with you about all of that. And I'll admit that's a pretty darn full space. Financial Advisor Success is great because it's actually not aimed at clients; it's aimed at other financial advisors to create that space, but where I see a lot of gaps in particular is the financial advice industry is 80% male and 95% white, and that in itself means that there are a lot of spaces that just naturally get filled by a lot of people who have the same story, and there are different takes on the industry.
Everyone will have such a unique perspective on what the industry offers and what the industry needs to improve. So to me that's one of the most glaring holes out there, but I am positive that I have my own blind spots, and there's someone who's sitting there like, oh my gosh, obviously you missed that, there's this gap right here. How can I not have seen that? It's like, great, well then go and fill that gap. You saw it and I didn't, but the odds are that by the time I find you, I realize that you are actually filling the gap that I was totally going to.
And then what advice would you have to someone or a company perhaps, thinking to start a podcast? You all have not only just done an amazing job with the podcast, but just the content and the information and so many elements. So what advice would you have?
My main piece of advice is my mantra, which is: the task is just the task. What I mean by that is I think that people can hear a lot about what I've talked about. And I've talked about subcontractors and breaking 10,000 views and pulling in big names from the industry. And they think, oh my, there's an entire team doing this and contractors and fancy programs that I'd have to pay for. And if in order for me to start, I have to do all of that. But even a lot of how Financial Advisor Success started. There was not a podcast producer, like an entire person geared toward just making podcasts when it started. There wasn't even a managing editor to schedule all of it out. When it started, it started out with the deputy editor that was doing all the prep and all the editing.
And then that has grown into like three different jobs now, as things have grown. And so, I think that when you're looking to start a podcast, it can get really easy to get tangled up a little bit in the weeds of all the things to expand into. I think that people should always be looking at their process once it's started and starting to figure out where they can grow, what they can improve. It was just over the last year that we chopped it from a two-hour long podcast to a 90-minute one. And that increased our views and our downloads an immense amount, you know? But in order to be able to make those choices, first we had to start. So don't make starting any more complicated than it needs to be. It's okay to be investing some things down in it, but the task is just the task, making the podcast at the end of the day has all these really daunting elements. But at the end of the day, it's sitting down and having a conversation, then sharing it out in public, you know? And so don't get daunted by all the big picture things that you lose track of like—what the thing actually is.
And then just to take that back, cuz I think in the marketing world sometimes, it's kind of like going to performance, right? And things are looking amazing. You're sitting there watching this performance, but there's so much that goes on behind the scenes. You've talked about some of that here. Can you share a little bit just how big the team is? Maybe a little bit of that. We'll wrap up here soon, but I just to give folks some context around what it takes.
So on the editorial team, which is what I manage, we have, I'm gonna literally count, five people on it full time, and a special shoutout to Elissa, who is the oft-mentioned podcast producer in all of this. Then we have a contracted graphic designer. She's the one who makes all of our customized social featured graphics for the podcast, as well as everything we see on there and then we have our contract with the Cashflow Podcasting team. So that is everyone I interact with directly. And we have a video editor to help with the Kitces & Carl podcast, because that's also released in a video format. So I guess that's seven or eight people I interact with directly.
Just on the podcast side?
No. Sorry. So that is everyone who does editorial. People who work really specifically with the podcast, there's me, there's Elissa, the podcast producer. And then we have Cashflow Podcasting, Candice, our video editor. And then we have Ashley Hunter, our associate editor who helps prep it in the website, helps make sure it actually goes live on YouTube and catches all of our errors before we do something embarrassing.
Oh my gosh. Well, it's pretty incredible. And also just a shoutout to you. Having worked firsthand with you and just seeing all the back and forth, it's incredible the attention to detail, just the thoughtfulness. It's amazing. So I've learned a lot. I know our team's learned a lot just in interacting with the Kitces team and it's fun. It's really fun. And this passion for putting out really quality work doesn't go unnoticed. So, I appreciate all you do. It's seen and it's felt and it's pretty incredible. So appreciate you sharing a little bit more behind the scenes. Is there anything else you wanna wrap up with or share you think would be valuable?
Well, I guess first off I'll say that I'm very fortunate to lead a very capable team of people. I think if it all came down to me to be doing all the problem solving, things would not be running nearly as smoothly. So I'm so grateful. I think that one of the best things is to be surrounding yourself with like-minded people who work really hard and have a lot of fun, you know? And then it makes hard work, not easy, but it makes it fun, you know? And then I think the last note that I will leave on is something that I alluded to a little bit earlier: the whole point with the Financial Advisory Success podcast is that it highlights that success is not always easy and success looks bright and shiny on the outside, and is often really formed through a lot of really hard work and struggle and sacrifice before it starts to turn into something that is profitable and fun.
And that people start to be like, oh, look at you, you just did this, you know? So I guess that kind of with that, if anyone who is listening is still in the iterating on something endlessly and trying to figure out what works and still struggling and thinking that they're just kind of shouting into the void, I guess, I just wanna say, I've been there and it will get better, and if you just keep showing up consistently, like showing up every day puts you ahead of probably 80% of people out there in this space. So show up, be consistent and know that the difficulty of getting started is something that even the most successful people have gone through and are also going through probably present tense as you're looking at their very cool, shiny, successful thing.
That's such good advice. It's so true. You're right. And I think more than half the battle is not just getting started, but keeping on with it. And I think something like a podcast is easy to get started, but not always keep going with, and you can apply that same kind of analogy if you will, to so many things and you're so right. Success does not come easy.
So yeah. A lot of times in writing, we talk about the inner editor and that in order to write, you have to turn off the inner editor. My inner editor is very loud. She is really diligent and really hard to ignore. As I've mentioned, I'm all for making a good process. I'm all for improving on things, but that always has to be after you actually know what your process is. And after the thing has actually started, if you can keep your inner editor quiet for just long enough to gain a little bit of momentum, to have someone listening in or checking out your blog and being like, Hey, I will notice if you don't post, then you can start to really iterate and start to improve the thing, but first you have to get started.
That's such good advice. Well, thank you so much for taking the time. I greatly appreciate it. And thank you for just sharing some of the behind the scenes. I hope this conversation will impact someone else's life or next steps or just lessons learned. And to the theme of success, it certainly takes a village and a community to learn from each other. I appreciate you sharing the story, not only your story, a little bit about your story, but then the day to day to keep the engine running. So it's pretty amazing.
And thank you so much again for having me on. I had a ton of fun talking through at random, and again, if you want just jump into the Asana conversation sometimes.
I'm all for that. Well, thank you again. Appreciate it.