Startup to Last

This week, we take a look inward and discuss what we can do to get more listeners for this podcast. We discuss how to identify an ideal audience, customer development, and more.

Show Notes

In this episode, we talk about why we started the podcast, who we think our ideal listener is, and how we plan to grow our audience.
After going back and forth, the following framework emerged for marketing a podcast
  • Why did we start the podcast?
  • Who is our audience and ideal listener?
  • What problem are we solving for our audience?
  • What makes our podcast unique?
  • How will we measure success?
  • How will we achieve success?
Takeaways include: 
  • Our ideal listener is someone who:
    • Wants to achieve freedom through entrepreneurship
    • Wants to build something sustainable that will last for many years
    • Does things the way they see is the right way to do them
    • Doesn't feel like they have a sufficient peer group for the hard conversations
  • Control, freedom, flexibility, and doing things the right way (as we define “right”) are important to our ideal listener
    • Our hosts (Tyler and Rick) share these values
  • There is a hole between the venture capital communities and serial entrepreneurs who are flipping companies
    • And that hole is build startups to last with sustainable impact and value creation for customers, employees, and owners
  • We think the Startup to Last podcast is unique in the following ways:
    • We have a deep-dive topic each week
    • We do not follow the guest-interview framework
    • Our hosts (Tyler and Rick) have skill sets that cover the whole spectrum in a way that most other podcast hosts don’t
    • We cover the spectrum in terms of company size and maturity
      • Tyler is 10 years into his company while Rick is in the very early stages of his company
    • We are both comfortable with the essence of entrepreneurship: not knowing the answer and being OK with talking about it until we find it
  • Startup to Last has achieved basic traction since launching in June 2019:
    • 200+ downloads across multiple platforms:
      • 33% are on Apple
      • 22% are on a web browser
      • 12% are on Spotify
      • The rest are on various other platforms.
    • 11+ subscribers (Thank you)
    • 95% of our downloads and subscribers are from the U.S
      • We've got a couple in Mexico, and then some in Europe
    • From July to August, we doubled the number of downloads month-over-month
  • We will measure success going forward by making the following metrics go up:
    • Subscribers
    • Downloads per most recent episode
  • We will achieve success by:
    • Talking to our existing listeners
    • Doing customer development with potential listeners
    • Experimenting with various growth channels and tactics
  • We think our ideal listeners hang out in the following places:
    • Online bootstrapper communities (e.g. people engaging at Indie Hackers and attendees at MicroConf )
    • Social media sites (e.g. people who follow similar podcasts on Twitter)
    • Q&A sites (e.g. people who are asking / answering related questions on Quora)
Why did we start the podcast?

Tyler: For anyone listening, you haven't been listening for long because this is our ninth episode ever. When we started this podcast, we were planning on just focusing on how do we make the content, so recording it, having a schedule, picking topics, editing, producing, publishing it. All that stuff, and at this point, we feel like we've kind of got it down. I mean, I'm sure we'll get better over time, but we've got a system where we can get podcasts published pretty regularly, so now the next question is, how do we get anyone to actually listen to this, and so we're going to talk about that today. 

Tyler: Keep in mind that neither of us have ever done a podcast before, so this is going to be very speculative and maybe every idea we have here is going to fail, but basically, we need to have this conversation anyway, so let's record it, and maybe people will find it interesting, what we're planning here. So with that said, you're more of a marketing person than me certainly, Rick, but I was thinking one thing we could potentially do is go over some ideas we already have or maybe you could start high-level and just talk about how you think we should even approach getting listeners to a podcast like this?

Rick: I think one challenge that we have, Tyler, is that the reason we created a podcast was pretty selfish. It wasn't with a customer in mind or an audience in mind. For background, we started this podcast because we want to spend more time together. Right? You live in St. Louis. I live in Utah. Well, you came out every other quarter or every few quarters or so. I recently made a trip out to St. Louis. We had a great time, and we both said, "We'd like to spend more time together. How do we do that?" I think both of us were thinking podcast when we said that. Two reasons. One, we want to spend more time together. Two, it's kind of interesting to see if a podcast would work. Neither of us have ever done that. Let's try it. And so we did that, and now it's been, you said, nine episodes, I think?

Tyler: Yeah. We did two or three that we kind of threw out before we started actually publishing them.

Rick: Yup, yup, and so now, what is kind of weird here is we have content that is valuable to us. I'm getting value out of this every week when I talk to you. I think you're getting value out of it. But the content that we've created was made for us. It wasn't made for some market out there of potential listeners that we have a high confidence that will get value out of this.

Tyler: Yes. Although, I listen to a lot of podcasts that are, if anything, even less for an audience than this. I listen to maybe five podcasts where it's two founders talking, and some of them don't even have deep-dive topics like we do. Some of them are just, "Hey, what did you work on this week? What did you work on this week? Okay. Bye," and I think they all have thousands or tens of thousands of listeners.

Rick: In marketing, that's luck. Right?

Tyler: Yes, but there's an audience that wants to listen to founders talking to each other I guess is my point.

Rick: I can't disagree with that. We're coming at this from a product-first standpoint or not even a product-first. We're coming at it from a, "Hey, we want to spend more time together, and then see what happens," which is a little different than, "Hey, there's a problem out there," like a normal business venture or something that you're designing to actually be sustainable and make money. You go, "Hey, there's a problem out here that I know about, or that I heard about, or I've witnessed, or I've felt myself, and there's a market for people who had this problem. I've talked to them, and they're... They don't tell me what the solution is, but based on their symptoms, what's out there currently from a current solution standpoint, what they are looking to achieve, what their ultimate outcome or job-to-be-done is. You go, "Okay. Well, this person is trying to get from A to B. There's a problem getting in the way. I'm going to solve that problem, and then we're going to create a solution for that." We really didn't go through that process. So, we're in our ninth episode. We've got some traction, and we could talk about that, but I don't know where to start

Tyler: Yeah. Well, one of the differences between you and me here is that I am a consumer of this product and you are not.

Rick: Yes.

Tyler: You don't listen to any podcasts, right?

Rick: Yes. Well, I should back up. I read [podcast] transcripts. And I just realized I do listen to podcasts, but they're only when Sable (my wife) makes me listen on long drives.


Why do people listen to podcasts like this?

Tyler: Okay. Yeah. I've been thinking about this a little bit. So to your point, yeah. Normally, what you do is you'd identify a problem, and then build the product around how you want to solve it. In our case, if we identified the way to solve the problem is to interview a guest every week, we wouldn't do that, so we're a little constrained here, but I've been trying to think like why should a podcast be valuable to anybody, and when I say podcast, I'm talking about this unscripted, not a lot of effort put into the production of it like this type of podcast. Not an NPR one where it's like really super polished. Every blog post and every book on startups is going to be more edited and polished than the content we produce here, so why would anyone listen to this? But we know people do, myself included, and so I was trying to think, "Why do I listen to it?" I think the reason is one of the ways we learn is by absorbing content, but one of the ways is also by observing how people we admire carry themselves. Babies mimic how adults make noises, and that's how they learn to talk, and then in adulthood, we listen to people we think are smart, or interesting, or whatever, and mimic them. I think I listen to these podcasts primarily not for the content, but to say like, "These are two smart, interesting people I otherwise would have no access to, and I get to see how they actually talk to each other, talk through problems, think about their businesses." The process is maybe more valuable to me than the actual conclusion of the content.

Rick: In other words, watching two types of people, two different types of people, problem-solve together and how they go about the problem-solving. You can learn by imitation. You can even identify patterns. Let me ask you the question. As you listen to these podcasts, have you identified specific talking patterns or problem-solving patterns that you can call to, or is it less specific and more just a generalist, "I'm learning. I know I'm getting something out of this?"

Tyler: Yeah. When I listen to our episodes to myself recorded after I get over the initial shock... Everyone hates hearing their own voice, but after that, when I hear myself talk, I think I sound like the people in the podcasts I listen to more than I probably did. I only started listening to these maybe two or three years ago. I absolutely think it affected how I talk even though I was not aware of that at the time. There's no conscious change on my part.

Rick: Got it. Interesting.

Tyler: Yeah, and I've... I was talking to one of my friends who... He listens to more of the NPR type of podcast, but... or I shouldn't say that, but it's not like his focus is this where it's about business. It's just, "Oh, interesting facts. Did you know that yadda, yadda?" But once again, he listens to them. He said, "Because smart, interesting people talking in an unguarded way is like a valuable thing for him."

Rick: Interesting. Okay, I get it, so one way to look at this is from ourselves, why do we listen to podcasts, and try to craft a plan to grow our audience based on people who are like us. Is that what you're suggesting?

Tyler: That's certainly one approach. I also think we should be very aware that there's an existing audience for this listening to other podcasts, and is there a way to market specifically to these people?


Who is our audience and ideal listener?

Rick: Okay, so where I would start with this if I were looking at this from a venture standpoint is I would go straight to the question, who or what. I guess it's who. Who is our ideal listener? I don't know who that is. I don't know a lot of people like you, for example, so where it falls... where that approach that we just discussed falls for me is... If I knew a lot of Tylers, I'd be a lot happier. I'd have a lot more people that I admire.

Tyler: What's the difference between me and the people you do now? Like you know other founders, you know CEOs, you know programmers. Right?

Rick: One, I think we've gone through some experiences together that have built trust between us, and that allows us to speak very candidly with each other, and so words aren't minced. If they are, they're clarified very quickly. Time is not wasted. We work through learning together and problem-solving together at a very fast pace. There are not many people who I've... who either... There may be two functions here. One is the trust. I haven't built trust with them enough to get to that point, or there's something else different about you that allows you to banter in a way that is extremely informative to me.

Tyler: It sounds like this might be something that develops over relationship and it's not like a fundamental characteristic about you. I feel the same way about everything you just said, but two other random people could equally well form that relationship with each other, but if you met one of them, you wouldn't have that. When we're thinking about our audience, it probably needs to be more like an innate characteristic about them rather than something that is built up via your or my relationship with them. Right?

Rick: Yeah, so I guess... Let me just ask the question. Who is our ideal listener in your opinion?

Tyler: I mean, it's got to be someone who's interested in business at least and probably startups. I'm really big on the whole "bootstrapper" thing, as you know, and I think there's a whole ecosystem of bootstrapped founders or wannabe founders. Most of the advice out there is for venture-backed like kind of Silicon Valley style startups, and I think anyone who's interested in startup like technology style entrepreneurship, but not going the Silicon Valley route I think is going to be up our alley, and I would guess we'll skew more favorable towards technical or product crowd than we would towards a business crowd. That would be my guess.

Rick: Why is that?

Tyler: One of the things I really like about what we've done so far at this podcast and the other ones I listen to is they're very like tactical and detail like getting-it-done-oriented, and certainly, there are business people that way, but that's a characteristic that I think really, really meshes with the programmer versus the person who's like going and building a brand strategy or something like that.

Rick: So builders?

Tyler: Yeah, makers. That type of thing. Yeah.

Rick: Okay, and those could be executives?

Tyler: Yes.

Rick: Right? That could be someone building a company. It could be someone building a department. Something creating. It's a maker, a creator type person.

Tyler: Yeah, and I'll also add all the people who listen to this type of podcast... All the other podcasts I listen to that are of this format are... All those people are in a community that I would refer to as the MicroConf community. Do you know MicroConf?

Rick: MicroConf?

Tyler: It's a conference.

Rick: Oh, okay. It's a conference?

Tyler: Yeah. It's a conference. So the podcast Startups For the Rest of Us with Rob Walling and I'm forgetting the other guy's name. That podcast. Those two people put on MicroConf. There's this whole community of bootstrap-ished startup, software people. All of the other podcasts are also people who go to that conference, so that's a community that definitely likes this type of podcast.

Rick: And this is a community of people who are saying no to venture capital and building "lifestyle" businesses?

Tyler: Maybe not... Some of them are lifestyle businesses. There's this whole movement right now for funding a business, but not with venture capital. TinySeed, Indie.vc. Well, one of the people who puts on MicroConf is the creator of TinySeed. I don't know if you're familiar with TinySeed?

Rick: I'm not.

Tyler: There's all these funding mechanisms for... it's not bootstrapping at this point, in my opinion, but it's not VC either.


What problem are we solving for them?

Rick: What are they trying to accomplish that's new and different? Okay. Let me go back up. I think what's happening here is we're saying that you see a problem. I don't know if you've experienced [this problem] personally. I want to know what that problem is," and then you also have identified an existing solution out there called MicroConf and this Startups For the Rest of Us podcast that seems to be trying to solve this problem. Can you go through what you see?

Tyler: Yeah. Well, I can tell you how they talk about it. They talk about it like anyone who's not in the VC Silicon Valley style. There's a sense of a lack of community. Entrepreneurship is very lonely. You need peers. You need people to talk to and relate to, but if you're not raising money for investors, you're not in these Y-combinator-style incubators or anything. The community isn't accessible to you, so this is like... That's what Startups For the Rest of Us means.

Rick: Sorry. What community?

Tyler: Well, any community, but like people you can relate to. If you work in a big company, you go into work. All day every day, you're surrounded by people, by peers you can talk to. If you're an entrepreneur who hasn't yet gotten to the point where your company has a lot of employees, you need peers or people to talk to from some other source, and that's the community they're trying to build, I think.

Rick: The community's differentiation between the... let's call it the Y-combinator [companies] or the venture-funded companies is what?

Tyler: They're not trying to take over the world. They're not unicorns. I wouldn't quite say they're lifestyle businesses necessarily.

Rick: But what are they trying to... What are these groups... What are they trying to accomplish? If they're not trying to do VC and they're not trying to build a lifestyle business, which I think we should define, but what is it that they're trying to accomplish?

Tyler: There's a whole spectrum of outcomes they want. I think both of us are in this spectrum of anywhere from ambitious, but not willing to give up control of the company, so control, and freedom, and flexibility are I think one of the big things. Some of them are straight-up like, "I want the four-hour work week." Anything along there, but the thing is investors don't want to invest in someone that isn't trying to create a unicorn for the most part.

Rick: Okay. I think when you said I'm part of those. I think I am too. I want to define what this is and give it a name, and I think we call it Startup to Last, right, which is not starting up to go with a 1% chance of success; Building something that sustainable, right? Sustainable is the phrase.

Tyler: Something that's sustainable. Although, I would say a discouraging number of the companies in this other community are looking for exits. I would say they're more like serial entrepreneurs hopping from thing to thing than I personally think this podcast is about.

Rick: Okay, so you see a hole between the venture capital communities that are, "Let's go make a ton of money, or fail, and/or die trying and these serial entrepreneurs who are flipping companies.

Tyler: Mm-hmm (affirmative).

Rick: And that hole is building something to last that has sustainable impact and produces value for the customer, the market it serves, the people who work at it, and the owners.

Tyler: Yeah. I hope so. It's possible that that specific niche is small enough that there's not a huge audience, but if I could drill down one layer more specific than just the whole MicroConf crowd, I'd say it's that sustainable, "I want to run this for the rest of my career type of outlook."

Rick: Cool.

Tyler: Do those people exist? I don't know.

Rick: Cool. I think that's the characteristic actually that you were asking for earlier. That's what I like about you is you're not... I'm going to take a step back, I'm halfway through The Fountainhead. Have you read this book?

Tyler: No.

Rick: It's by a woman. I think it was in the 1940s. It was written by... Her name is Ayn Rand, and she's a philosopher.

Tyler: Yeah, I know who she is.

Rick: Yeah. You're laughing. Okay, so... there is something in the book that I don't fully understand in Rand's philosophy. I think it's called objectivism. I don't really understand it, but one thing that is coming out of the book very clearly is that she believes strongly that the ideal man or the best version of man does not compromise his or her ideals.

Tyler: Okay.

Rick: Okay? I think you don't do that, and that's one thing that I actually like about you is you are pretty uncompromising with being less annoying and doing things the way that you want to do them because you believe they're right, not because it's what everyone else is doing.

Tyler: I appreciate that. I'll try not to be compared to Ayn Rand in the future, but I appreciate that.

Rick: I don't even know if that's actually what she's saying.

Tyler: She's like the god of libertarians basically, so politically, we do not align, but I appreciate the comment nonetheless. Yeah, and I guess there's one possibility here, which is no one wants to listen to this. In which case, we'll keep making it and just stop trying to market it. Right?

Rick: Yeah, or we stop recording it altogether. Although, I get value out of the recording, so it's probably worth it...

Tyler: I go back and listen to every single one of these at least once.

Rick: I'm the guy who does the transcription. We have an automated transcription service, but I'm the one who polishes it a little bit before we post, so I listen to it too. I would not want to stop recording it either. Okay, so I think there's some ideal that we share, and it gets into freedom, not giving up control, doing things the way we see is the right way to do them as an entrepreneur and as an employer. And we're young. I think that that our ideals and what we think is best is changing based on learnings. Would you agree?

Tyler: Yeah, absolutely.

Rick: But it is this idea of freedom, and doing... creating... living and being the way you want to be without working for the man.

Tyler: Yeah. Freedom is a huge topic on Startups For The Rest of Us. Yeah, it's basically... You could even pursue the exact same goals that a venture-backed company does, but you're doing it because you want to, not because you raise money and you're forced into that one path.

Rick: Got it. All right, so our ideal listener is someone who wants to achieve freedom through entrepreneurship or by building something, and I guess the subset is doing that in a way that lasts a long time versus going through a quick exit and flipping a company, but building something that is sustainable and will keep on keeping on for years to come.

Tyler: Yeah, and probably somebody that doesn't feel like they have a peer group to have these conversations with personally or at least not big enough one. That may mean someone working at a big company who's aspiring to go into this world but doesn't know people yet. It might mean someone who's an indie founder working remotely, but yeah.

Rick: Okay. Cool, so I think there's a lot of people out there who are interested in this, and even if they weren't like “ideal”, I think there's a huge circle around the big one, which is, "I want to achieve freedom through entrepreneurship."

Tyler: Yeah.

Rick: I think that group could get value... maybe not as much as the ideal person that we just described, but maybe interested in listening.

Tyler: Okay, so let's dive into the actual... we've got some kind of persona we want to make this for. How do we get anyone to pay attention to this?

Rick: So I wouldn't go there yet.

Tyler: Okay. We've got 15 minutes.

Rick: Yeah, so I think the second question is... What is it that we are doing uniquely? What do we have to say about this topic that is unique or interesting. And what podcast episodes can we provide that would actually be interesting to them?

Tyler: Yeah, although... So first of all, I'm not sure it has to be unique in the true sense of the word. Like all these other podcasts that do this, there's only so much for any two people to talk about, and so they publish it most once a week. Normally, 30-minute episodes. It's possible people just want more content that's the same. That's one possibility. What I'll say is different from the ones I listen to is having the deep-dive topic each week. Honestly, we might run out of topics. We might hit a point where we can't come up with 52 unique topics every single year, but for now, that's a bit unique, and then I think one difference is that most of them are either two business people or two technical people. I think it's interesting that your skillset and my skillset right now overlap a little, but cover the whole spectrum in a way that most of the groups don't.

Rick: Interesting, so one, we have both been CEOs of a web startup and where I'm weak, you cover that really well, and where you're weak, I cover that decent- maybe not quite as well as you cover mine, but okay.

Tyler: I think so. I think absolutely.

Rick: Yeah.

Tyler: I also think it's great that you are in the very, very beginning days of your business. I'm 10 years into mine, so we also cover the spectrum in terms of like the size and maturity of the company as well.

Rick: Yes. Okay, so that's unique. I agree that bringing a problem is a topic and having that be discussed is unique. I haven't heard of that before. It's just like most podcasts are guest-based or purely unstructured conversation-based like you discussed.

Tyler: Yeah, and almost all startup podcasts are interviewing guests. I fucking hate that style. There are a million of them out there, and I think just by virtue of us not having guests, we're immediately different from the majority of podcasts.

Rick: Cool. OK. Here's the question. What do we know about the space that other people find difficult to know, or what is easy to us in this space that may be difficult to someone who's trying to get into this space?

Tyler: Yeah. Well, I don't know if this is universally true to everybody, but I'll say a lot of people I talk with like when you're an experienced entrepreneur as we both are, one thing you get very, very comfortable with is not knowing at all what you're doing and just do... Like what we're doing right now. Neither of us started this conversation with any clue what our outcome would be. Maybe we won't have a conclusion, but I do think it's valuable for people having gone through that to hear two people that are comfortable just brainstorming a topic hear that.

Rick: Can I summarize it? Two people who are comfortable not knowing the answer to the question and not letting that stop the conversation.

Tyler: Right. It probably makes the insights a little worse, but maybe the process is more valuable.

Rick: Interesting. Okay.

Tyler: That was just the first thing that came to mind for me.

Rick: That's the essence of entrepreneurship. That's what it takes. You have to be okay with uncertainty, okay with not knowing, okay with change, and when you're scared... this gets into leadership at its core, when you're scared... it's very hard to be a good leader whether you're a one-person show or a 100-person company. Okay. That really helps me, so it's this we're comfortable being exposed [for] not knowing something, and confident that by talking about it openly and asking questions, we can get to an answer.

Tyler: Yeah. I mean, I think that we have not validated that that is true that like this is going to be our differentiator, but I buy that it is just on intuition.

Rick: Let's call it a hypothesis and ultimately this podcast is the test of that. But I agree that that is the unique thing about this.

Tyler: Okay.


How will we measure success?

Rick: I know you want to get to this, so can I run through some stats of where we are right now? Like at the end of the day, we want to increase these. Right?

Tyler: Yeah, yeah. We want to make those numbers go up.

Rick: Yeah, so we really launched this in late June. So far, we've had about 200 downloads, which means someone has either played an episode on our website or downloaded it on Apple Podcast or played it on Spotify. Right?

Tyler: Yeah, and probably a lot of downloads... For a mature podcast, a lot of downloads are not necessarily people listening to it because it happens automatically in the background because they're subscribed.

Rick: Yup, and then our podcast host does this thing where they estimate the number of subscribers based on how many people have downloaded versus streamed, and they come to an estimate. We don't know how that works, but it says we have 11 consistent subscribers.

Tyler: Thank you all 11 people.

Rick: I'm going to reduce that by two because...

Tyler: Because you and I both do it.

Rick: Yeah, yeah, so it's probably nine subscribers. Thank you whoever you are out there. In terms of where they're listening, 33% are on Apple, 22% are on desktop, and 12% are on Spotify.

Tyler: Desktop meaning streaming through the website?

Rick: Streaming through the website. Yes.

Tyler: Not downloading it?

Rick: Correct. The web browser. And then, 95% of our downloads and subscribers are from the U.S. We've got a couple in Mexico, and then somewhere in Europe. It wasn't specific. I think the big stat that is interesting is that from July to August, we doubled the number of downloads month over month, so there is an upward trend here. September is just starting. We just had Labor Day weekend. If we could double our downloads every month for the rest of the year, we'd be pretty happy. Right?

Tyler: Yeah. Although, I think a more interesting thing to look at is how many downloads are we getting of each episode, and that number has not... Like the peak was three episodes ago, and then we more or less leveled, but it certainly hasn't been going up since then.

Rick: Yup. Yeah, so how do we make the downloads go up per episode for our most recent episodes, and then how do we make the subscriber number go up? Right? That's the question.

Tyler: Yeah, I think that's right.

How do we achieve success?

Rick: Okay. How do we do that?

Tyler: Yeah. Well, let's talk about the framework we're using here. We have a Google Doc that has three sections. What is on autopilot, what are we experimenting with, and what ideas we want to try. The idea is... we don't have anything yet that works, but once something works that we just need to keep doing, we're going to move it to autopilot, and then we're going to take things from the backlog and put them in the experimental category, and one or both of us will do those things to try and make it work. So, what we're really talking about here is what are our backlog of ideas that we're excited about?

Rick: Yeah. Basically, the way we're going to right now is in the experimentation model.

Tyler: Mm-hmm (affirmative).

Rick: I think what we just discussed actually hones our experimentation a little bit, so one is I think we gave a much better idea who our ideal listener is now, and so we should... I want to kind of... I think one thing we should do is really think about where those people hang out. I think you're further ahead of this than me because I think you always had this ideal listener in your head.

Tyler: Well, because I'm more of our ideal listener than you are.

Rick: Exactly. I'm entering the space of the ideal listener. Right? I'm new to the space, and I need... I actually would be a really good person to start consuming this content if I wasn't producing it.

Tyler: Right.

Rick: Where are these people hanging out? Let's start there. I think you've... Maybe you can talk about Indie Hacker. I don't really know what that is still.

Tyler: Yes. There's a variety of online communities. Reddit has some stuff. Hacker News has some stuff. Indie Hackers is a website. Stripe acquired it, so technically, it's owned by Stripe, but there's basically no relationship.

Rick: Stripe owns Indie Hackers?

Tyler: Mm-hmm (affirmative).

Rick: Why did they buy Indie Hackers?

Tyler: Stripe's mission is something like “increase the GDP of the web,” and I think they're saying Indie Hackers is a place for aspiring entrepreneurs to get over the hump of getting their business started to help Stripe.

Rick: Okay. Cool. That makes total sense.

Tyler: But yeah, it's mostly very, very early entrepreneurs on Indie Hackers. It's a message board with some other features. You can like write blog posts similar to Medium. They have a podcast. They interview founders. Things like that.

Rick: Okay, so there's online communities where these people hang out? We could go there.

Tyler: Yeah, and what I've done without any real strategy behind it. I'm moderately interested in participating in that community anyway. I've already done an interview with them years ago that still gets a little traffic. I've started trying to leave about one comment per day on Indie Hackers. Not promoting the podcast or anything. Just maybe someone will see me and it will help Less Annoying CRM and Startup to Last hopefully.

Rick: Well, I was looking on our Google Analytics. I think it's 70% of our traffic over the last week came from Indie Hackers.

Tyler: Oh.

Rick: Yeah.

Tyler: That's wild.

Rick: I didn't know you were doing that, so it makes sense.

Tyler: Yeah. I'd be interested to know what worked. So in order to market this podcast on Indie Hackers, I think what I have to do is market Less Annoying CRM because that's a much more interesting story at this point because it has millions of dollars in revenue and stuff like that. Most of the engagement I got was I posted a milestone about Less Annoying CRM that we hit our 10-year anniversary and not a lot, but maybe 5 to 10 people commented like, "Hey, great job. That's awesome." I wouldn't be surprised if that's the main way people saw this podcast.

Rick: I agree. Yeah.

Tyler: I can't do that every day obviously.

Rick: Yeah. Yeah, exactly. It's totally like we're marketing our milestones individually, and as they look through our bio online, whether that's Twitter, LinkedIn, Indie Hacker, they're seeing that we have this thing going on, and clicking through, and checking it out.

Tyler: Right.

Rick: Okay, so we've got... We should definitely identify more places like Indie Hacker where these people are hanging out. I guess how do we get people to actually start listening intentionally? Do we have to be really patient about this and passive about it like you were just talking about, or do we get aggressive?

Tyler: Well, so from what I understand, podcasts are a very quickly growing medium, and it's possible that without us doing anything, in order of magnitude, more podcast listeners will enter the potential audience over the next five years that exist now, so one thing that might be important here is trying to like... There's a question. Do we try to go out and find our typical person, but who isn't necessarily listening to podcasts and base it more of interest, or would it be better to say, "People who are already listening to podcasts are going to understand how this works. They know how to subscribe and all that. Let's really focus on them?" So Indie Hackers has a whole group just for podcasters, for example.

Rick: I'm thinking right now. I'm realizing we're kind of getting into the weeds, and I just remembered a book I recently read called The Audience Revolution, I think, and it's by a guy named Danny... I'm going to get this wrong, but I think it's Danny Iny. It's a short book like a hundred pages. This guy has an audience, right, and he's built a book about how to build an audience because most of his audience are people who are thought leaders, consultants, writers, and want to build their own audience. Right?

Tyler: Yeah. I'm rolling my eyes real hard right now.

Rick: Okay. Why are you doing that?

Tyler: Well, go ahead, and then I'm going to rant for a second.

Rick: Okay, so I think that there... There's a framework from the book that I'm going to try to recall, and one is that before you can really market the podcast aggressively, you've got to create some foundational listeners. Ultimately, what grows an audience is having true fans in your audience, and so getting to that like foundation.

Tyler: It's like crossing the chasm, right?

Rick: Yes.

Tyler: You start with your cutting-edge early adopters, and then gradually move more mainstream.

Rick: Exactly, and so maybe like one way to tackle this is to not worry about just generally growing the number, but really focusing on getting some number. Maybe it's a hundred. I don't know what the right number is, but of really raving, highly-engaged audience members versus just going after everyone.

Tyler: My instinct is if we want that, we should be going after the people that listen to the other similar podcasts just because…

Rick: Okay. Go after the existing market.

Tyler: Yeah. We don't have to change their behavior. They already have... This is a habit, and all we have to do is be as good as the other ones, and they'll just add it into their line-up.

Rick: Okay.

Tyler: By the way, if I can give my rant for a second.

Rick: Yeah. What's the rant?

Tyler: Almost everybody who is like a "thought leader" is good at building an audience and potentially good at nothing else, and so they're giving advice about something without necessarily actually being good at that. What they're good at is being a thought leader, and so if you follow them as a model, you end up developing skills to be a thought leader, not the skills to do whatever it is you thought you wanted to do, and this really applies in entrepreneurship, so anyway, which is actually crazy.

Rick: Yeah. Yeah, I totally hear you.

Tyler: Yeah. We don't need to dive into that. I just had to put that off my chest.

Rick: Heard and noted. We could rant on that all day.

Tyler: Yeah.

Rick: What I'm getting to is, so I... So high level. There's a market out there of people who want to learn how to generate freedom through entrepreneurship. Ideally, they want to do it by building a business that they own, control, and will run for a long period of time, maybe for the rest of their lives, and some subset of those people out there are already listening to podcasts. How do we go get those people? I totally agree. Focus on them.

Tyler: Okay, so one option I think... I realize advertising probably should not be our go-to here for cost reasons like... We don't have any plans to make money off this, so it's not like we have a huge budget to do this, but if we wanted to, it's pretty easy to see who on Twitter follows these podcasts or the hosts of these podcasts to get a pretty good sense of who their audiences are.

Rick: Yeah.

Tyler: We can either advertise to them directly, or maybe there's some kind of more subtle gorilla type thing. There's trying to guess post or not guest post, but the equivalent of that like be a guest on their podcasts. I think that's hard because they all have huge networks of entrepreneur friends that you and I are not in, but those are two things that come to mind.

Rick: Interesting, so basically, look at the podcast hosts as the key influencers and really try to build relationships with them, or by going on their podcast and using them as basically a key audience member for us or being pretty competitive, and going in, and finding out who's listening, and going, "Hey, like I saw you listen to this already. You should check out... Will you check out ours and give us some feedback?"

Tyler: Yeah, and once again though, this isn't like selling software where they're going to use one or the other. I don't think it's competing. As a matter of fact, my absolute favorite podcast is called Art of Product, and one of the hosts on that regularly makes a call for more entrepreneurs to do exactly what we're doing. He's like, "I love listening to this type of podcast, and there's only like 10 of them. I want a hundred."

Rick: It seems to me that the people who have relationships with the people that we want to go get in this first segment, which is our ideal listeners who already listen to podcasts. If we could build relationships with these podcasts and they would help us promote our podcast, whether that's advertising on their podcast, retweeting, or even just telling people about us, that would be high return on investment.

Tyler: It would. None of them have advertising on their podcasts.

Rick: Okay.

Tyler: They occasionally do guests, but like us, the format is not guest. It's normally one of the people is on vacation and they need someone to fill in, and I get the impression always someone they know, but if we somehow knew them, that would be one way. I imagine that they just get absolutely swamped with wannabe podcasters like us doing this. This is the classic problem with marketing anything is when you're just... Like now with Less Annoying CRM, I can go somewhere and say, "We have some credibility. We have revenue. We have users. Look at our 300 reviews on G2 Crowd that say five stars." We can't do that.

Rick: I know. You're right. We're not there yet. The first step is reaching out, finding ideal people, and reaching out to them individually and saying, "Hey, will you check out our podcast?" and talking to them, and getting feedback. It's interacting with our audience.

Tyler: Yeah.

Rick: Whoever you are out there who's listening to this, please like reach out to us and talk to us about this because honestly, just interacting with you is going to help us, and I think at the end of the day, in fact, we could have more interactions with our ideal listeners, and maybe some of you aren't ideal listeners. We'd love to hear why you're listening. Ideal listeners as we just described them at least.

Tyler: Yeah. One of them is my dad.

Rick: Oh, that's great. Yeah. Well, he has an interest in this space.

Tyler: Yes. Yes, he does.

Rick: I guess what I'm getting to is yeah, let's go find these people, reach out to them, and see what they say, and talk. Let's just talk to our audience more.

Tyler: Yeah. There's a chicken or the egg thing here, which of the nine subscribers, let's say five of them are listening, and one is my brother, and one is my dad, so we've got three people. We need to be able to get some listeners. The way I think about marketing at Less Annoying CRM is you plant a seed, and you hope that the seed is completely disconnected from your existing network because a network of people is going to saturate itself. Eventually, everyone in the network has heard about whatever. By the paid advertising and things like that we do, you plant a seed and hope to build a new network that didn't previously exist. I feel like we need to be able to plant some seeds before we have enough of an audience to really engage.

Rick: I see it so clearly now. We're starting a business. You don't start marketing on Twitter. You call your customer and you talk to them, and maybe people don't want to be called about this, but you reach out and say, "Hey, I have something of value I think you'd like," or maybe you don't even pitch it. You just say, "Hey, I want to walk through The Mom Test with you about this." Use basic customer development, and some percent of those turn into listeners.

Tyler: So walk me through specifically though. Generally, I agree with you, but who and how?

Rick: I'm going straight to Twitter for some reason because I feel like that's the people who are willing to be open about conversations, and have light touches, and interact. There's also data on Twitter around who is more influential than everyone else.

Tyler: Twitter is definitely the network of choice for the people who I'm aware of in this podcasting space also.

Rick: Exactly. They're not trying to make a quick buck on LinkedIn by spamming all of the people who were kind enough to accept their connection request. All right. Talk about rant, right?

Tyler: Yeah.

Rick: The Mom Test is a book about how to go do customer development by interviewing your potential customers and asking them questions without selling them, and generally, you, through asking these questions, do provide value to them by asking them about this, and you can even give them an Amazon gift card or something for their time. At the end of the day, I think that's what we should do. We should develop some questions that we want to ask these ideal listeners, and then if we each do one interview a week, like…

Tyler: So are you saying just DM them on Twitter?

Rick: Yeah.

Tyler: Like find people who follow our product, and Startups For The Rest of Us, and podcasts like that, and just DM them?

Rick: DM 'em. I was thinking that the best thing to do would be like go answer a question on Quora and see who responds, but no. I want to confirm that we have like an ideal listener here and that they do want to listen to our unique approach. Then, I want to invite them to come here and see what happens. If they come and they started interacting with us, and they give us some feedback, we should be able to improve, and then once we build a foundation, we can start talking about like, "Okay. How do we plant more seeds?"

Tyler: Yeah.

Rick: I feel like the plant seeds conversation is premature, I guess what I'm trying to say.

Tyler: That's fine. Yeah. I guess my point is planting seeds comes before engaging with an existing audience or some sort of audience building has to come before we engage with the audience that we have.

Rick: Exactly, and I guess what I'm saying is I want to avoid planting marketing channel seeds and have more customer conversations.

Tyler: Customer development type stuff?

Rick: Yeah, yeah.

Tyler: Yeah. Okay. I buy that. Cool. Well, obviously, we need to go actually do this. I'm going to keep up some of my Indie Hackers stuff. I have a handful of other ideas related to that. I still don't think the Quora thing is a bad idea, but whatever. We should each pick some things. It sounds like you're at least going to try this Twitter thing. I'm happy to, but...

Rick: Well, I don't know of this Twitter thing. I think my biggest takeaway is that I wasn't clear about who our ideal listener coming into this, and I'm glad we had this podcast [topic] because we now have a hypothesis that we think may be true. I'm ready to go test if that's true or not, and whether what we're delivering or contemplating delivering is a value to them, and I think I can get an answer to that by the end of September, so for me, that's the number one thing coming out of this, and I'm happy to keep experimenting. I think we should experiment with a bunch of different things, but for me, that's the number one thing is just go talk to people about what we're doing and seeing what they say.

Tyler: Yeah. We still don't exactly have the most immediate next step though. Like talking to people is a good goal, but like something along the lines of finding five people on Twitter that follow this thing and DM them or something like that.

Rick: Well say that. I love that idea.

Tyler: Well, I don't want to do that. That makes me nervous.

Rick: I think Indie Hacker is your community that you need to... However you do it, it'd be interesting to see if you could have some interactions with people you don't have a relationship with that aren't biased, aren't your mom...

Tyler: I already know how to do that on Indie Hackers because they have a podcast channel thing that I'm going to go post on and say... I think you only really get one shot at this, but I'm going to say, "I want to do some customer development calls. Who will get on the phone with me?"


Takeaways

Rick: Exactly, and maybe that's what I need to do is ask for customer development calls on Twitter with whatever Twitter features are for this and see what happens.
“What I need to do is ask for customer development calls. That’s my takeaway.
Tyler: Yeah. Okay.

Rick: That's my takeaway.

Tyler: Great, so we've each got a goal here. This was great. I think we moved the ball forward. It's going to be really interesting. Hopefully, in a month from now, we can come back and give some updates on how this is going.

Rick: Yeah, totally.

Tyler: All right. Cool. You want to sign us off here?

Rick: I guess I just wanted to ask real quickly. Do you have any other takeaways?

Tyler: No. I don't, but I guess I'll just say this is a little different from the other episodes we've done in that neither of us knew what we were doing. In a lot of ways, we didn't reach like a super satisfying conclusion the way we do when one of us is an expert on the topic. Like to your point about, "If people are listening, let us know," I'd be very interested to know if that's an interesting thing to listen to or if someone was sitting here like, "I just spent an hour of my life, and they didn't even figure it out," so I'd love to know that.

Rick: Yeah, likewise. All right, so everyone, thanks for listening. You can join the conversation on this topic and review past topics by visiting www.startuptolast.com. We'd love to hear from you. We want your thoughts. We want more interaction, so all you.. I think it's 11 now. That's what I said. Come talk to us. Even if you tell us we suck, that's something. Again, it's startuptolast.com, and we'll see you next week. It was good talking to you.

What is Startup to Last?

Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.