E03 w/ Craig Hewitt: Restarting growth after stuck at €16k/mo

The STARRING TIAGO FERREIRA. The star of today's episode of Smart Bear Live are two founders of a podcasting content tool who quickly bootstrapped to 16K in MRR in just 18 months, with tens of thousands of trial users, and turned down an acquisition offer last year.

That's a pretty strong move. I like that. But with 15% to 20% churn and only 500 of those trial users converting to paying customersright now, growth has already plateaued. So we're going to use systematic methods to diagnose what's going on and figure out how to restart growth.

And so who is this "we," you might ask? Well, me. I'm Jason Cohen. I'm known online as Smart Bear. I've founded and run two unicorns over the past 25 years. That's Smart Bear and WP Engine. I've both bootstrapped and raised hundreds of millions of dollars.

I've invested in 60 startups. And for 20 years, I've written long-form articles about everything I know. And I just finished a book called Hidden Multipliers, which has all my best ideas for how to grow with your existing budget and team.

Now, joining me as the co-host of this episode is someone with deep experience in the podcasting market and has talked to the founders that you'll meet in just a second as well. So he has insider information, and I don't.

And I think playing off of that is going to be very interesting. So that's Craig Hewitt, the founder and CEO of Castos, which is software for podcast hosting and analytics. And Craig also has his own great podcast called Rogue Startups.

So Craig knows everything about selling software in the podcast market, having bootstrapped a great company himself. So welcome, Craig.

Hey, thanks so much for having me.

So let's turn to the stars of the show. And this is Tiago Ferreira and João Amaro—they'll correct me later, of course—out of Lisbon, Portugal, with their bootstrapped startup called Podsqueeze. So they've tried things like free trials. They've landed Portuguese companies who want to build podcasts, sometimes with AI, sometimes not, sometimes with distribution, sometimes not, sometimes cutting things up into shorts or squeezing all the ums and ahs out of a podcast, which I assume is where the company name comes from.

And by the way, maybe that's too many things, and maybe that's part of the problem. But anyways, they've landed some Portuguese companies, haven't really broken out in terms of big customers into other countries. And maybe they've been a little distracted with some side projects, which I also want to talk about.

And anyway, the issue is that Podsqueeze has plateaued, and they need a way out. And so, guys, welcome. And thank you for your bravery and generosity, really, coming here today, being willing to expose yourself, your business, your numbers, your challenges, so that others can learn how to analyze and solve things like this too.

That's very wonderful. And we all thank you for that.

Of course. Yeah. Happy to do this.

Thank you very much. Yeah, I have to be honest, I'm a bit nervous to expose everything, but, you know, it's all in the idea of building in public. And it's awesome to be here with Craig, which has so much experience.

And we spoke, as you said, we spoke a lot. So he has a lot of experience in the podcasting world. And I loved the episode you did with Dimitriu, so I'm quite excited to dive in.

Let's dive into things. So maybe you guys can kick us off by, besides correcting the pronunciations of your names, which you should do, filling in a little more detail. What's the situation? We don't need the entire history of the company, just what do we need to know now?

If you want to throw up some stats and stuff, that's fine. Just things that's going to help us understand what's going on and what we should do next.

Maybe I can do a little introduction. So it all started when GPT came around in 2023, I think. And we were brainstorming together what would be our next product. And so we tried to think about creating something that could benefit from GPT that just came out.

Tiago was podcasting back then, and he still does. And so it came the idea of creating something that would transcribe the podcast and write show notes. So we launched that MVP. It was very buggy, but it is the bootstrapped way.

So we launched something very simple. And it got a lot of traction, traction that we have never seen before in other products that we built. And so, and I think word to mouth was a big part of it.

But also, in those two first weeks, we did a lot of different things, like cold email. We did a very successful launch in Product Hunt as well. So the product got a lot of traction, and that's why it got to 14K fairly quickly.

Then.

I'm sorry, can I ask what timeline is that, like 14K? So from launch to 14K?

Maybe six months.

Shall I show the graph? Since I have the graph, I can show it. So here we go. Three, two, one. Let's make it public. Right, so I think this is basically what João is talking about. So this is the growth

that it all happened in the first, you know, few months. And then you can see.

That's amazing. So it was what, like six months or even less to get to 14K?

Yeah, yeah. Exactly.

And then how long has it been flat?

For maybe two years, almost.

Yeah.

So here you can see as well. Sorry, João. So this is in euros,right? So we were charging in dollars as well. So this, there's like this dip here that came.

No, that stuff's not, that doesn't matter. Here's what's interesting. You've done lots of things in this two years to try to change this curve, yes? And yet nothing has changed it at all.

Correct.

Why this one little rise? You're talking about noise. So this is actually already an interesting thing. When you've tried many different things, and it makes no difference at all, that's especially interesting. Like not even more people coming in, not even fewer people canceling, or something simultaneous like, oh, a lot of people came in, but they were all bad.

So I'm curious, like what are the set of, like obviously you added free trials. What are the set of things you did in these two years, which we know now made no difference at a macro level?

Where we start.

Yeah, that's so many things. We really tried, so.

I just wanted to add another note. There was a little thing that we did that increased the MRR in 2K, but it's not showing here in Stripe, which was the B2B. So we invoice our B2Bs outside of Stripe, and we were able to get around 2K to that MRR.

But.

Okay, good. So let's separate the, let's separate that in our minds. You already have it separated in your data, which is probably a good thing. It's bad to combine everything onto one chart because then it's very hard to tell what's going on.

It's true that that's the whole company, but when you diagnose stuff, it's best to try to segment it out. Because often it's true that like this segment doesn't behave like that one, not just in revenue, but many things, even in the actions you take to talk to them or sell them or retain them or what features they need.

Like often many things are different. So it's useful to segment. So let's keep it segmented, even in the conversation. So I feel like people say B2B when what they mean is sales versus self-serve, which is not what B2B means.

Yeah, yeah, yeah.

Right. So that's probably what you mean. So, okay, this is the self-serve. So you say you've done lots of things. So I'm guessing ads and SEO and social stuff, and you've had a podcast for years, and none of that matters for this,right?

Yeah.

Can I, can I maybe, I'll, of course, if I'm going to be here and explain everything we've done, we can stay here for hours. But I can do a quick recap. So basically, when we first started, as João said, it was a very basic product.

So show notes and transcript and so on. And the marketing was, I think we took a bit

a ride from, you know, the whole GPT trend. So we didn't do any SEO. We did a lot of cold email, Reddit, you know, product hunt launches. And that was, you know, enough to grow to basically 14K. And then from September on, we started seeing less people coming to the website, and we started focusing on SEO.

And since then, I think we have made great efforts, and we were very successful in bringing a lot of traffic.

No, we weren't.

In terms of traffic. Not in terms of MRR. That's exactly the argument that João and I always have is that we were successful, and I can show you the metrics on the traffic we're having, not, you know, converting them into MRR.

We launched.

Yeah, that's the other side of writing, that's the other side of writing a hype wave is you can get a lot of traffic, but since it's hype, it's either ephemeral, they're not serious, or they buy, but cancel quickly.

You know, one way or another, it's not real when it's hype. That's not always true. I mean, I'm sure we all use AI a lot in various ways. So it's not just hype,right? Like clearly it's not just hype, but there is also a lot of hype.

There is also a lot of noise when there's hype. That's okay. That just means, allright, well, that's just what this business will have to process and understand. That's allright. Like it's not a failure or anything. But it just means, like you said, like, oh, we got a lot of traffic from SEO.

That's better than not getting traffic,right? But clearly, like it's not working. Now, of course, maybe that means the website is the problem. Maybe they are interested. There is a signal there, and your positioning is not good. It's possible,right?

Right. To give you some context, so, and I think Craig will definitely have more insights here. It's an industry with churn, which is quite high. You know, there's this innate churn of people that just start after a few episodes, and then they quit.

And I think the fact that we were able to get this SEO going is the reason why the business didn't die. This is my opinion. Because also we saw a lot of our competitors just, you know, eventually dying.

Since then, we introduced a few major features. We introduced video clips. Again, you don't see the difference. So I don't know. Maybe it's not needed. We do have people using it. We introduced a bunch of other things. We improved a lot that I will skip the details here.

And then even.

Right, but what does that mean? What does that mean to you when you realize, okay, we're great at SEO, we've added, we've like, have all kinds of features, which you do, and it just doesn't seem to matter?

We actually, I mean, we spent so much time looking at analytics and our conversion and our traffic and all that stuff. The reason it's not growing is that SEO also plateaued. So our distribution actually plateaued.

No, that's not why it's not growing. Because if your cancellation were lower, you'd be growing with a plateaued SEO. Because you'd still have X people converting to a paid customer per month. And if cancellation wasn't so bad, you'd be growing.

No, I mean, there are, of course, in order to grow, we need to either increase traffic, conversions, or lower churn. I guess these are the three main factors.

Right. And you just said you got a lot of traffic from SEO.

Exactly.

So the reason you're not growing is not because you need even more traffic than a lot. That's probably not it. That's probably something that's going well.

Yeah. So assuming that conversion and churn stays the same, we were not able to increase the traffic enough to see any difference in growth.

No, no, no. So the point is, if you're already getting a lot of traffic off of SEO, then what we would say at a very high level is you're doing well with SEO.

Yeah.

So of course, if you're doing well in something, you should lean even further into it and try to do more with it because it's the strength. So that's true. On the other hand, we wouldn't expect like 10X more traffic from SEO because you're already doing well with it, and you're already getting a good bulk of traffic.

So that's probably, so while it's good to stick with that, that's not what's going to like dramatically change the company. It's already going well. We have to ask what's not going well. Because let's put it this way. There's more, one or more things that are going so badly that despite being good at SEO, it's not working.

Despite having enough traffic coming to the website, we're stuck.

Are you talking about conversion and churn?

Well, I mean, those, sure.

Yes.

But what I would say is conversion and churn are both lagging indicators of what I'm actually talking about,right? So yes, you can measure it there. But churn means either they weren't that serious, like you say, most podcasters aren't.

Most podcasters start and then end. And Craig can probably give us some data about that. And so guys, you guys can probably get too, like everyone here but me can probably do that. So, but some podcasters stay for years.

I wonder which one you want as a customer.

Well,right now.

Which kind do you want? Someone who's had a podcast for five years and is going to continue having it for five years, or someone who just started a podcast where you guys can tell me what the likelihood is that they'll still be doing that in a year?

The answer is, I think, neither. We want agencies that manage multiple podcasts. Those are the clients that have been more sticky that manage 40, 50 podcasts because the likelihood of them stopping using Podsqueeze is quite low.

Okay, I love that. Just to put a number on it, because we have the experts here, what is the answer to, I know there's a lot of new podcasts created per month, but I'm curious, like how many is created per month or year?

How many last a year or six months or however you guys, and maybe Craig, maybe you have this, but like what are those, like roughly, what's that look like?

I don't know the number. I know that like as an industry, the number that kind of like net number is pretty flat, I think, like number of new podcasts versus people who kind of stopped. Like the industry as a whole is not growing like on a net basis, Jason, like you had a tweet about this.

I just want to offer two, I think Tiago just said the most interesting thing of the whole conversation, but I just want to like add my take on like the growth conundrum for the kind of PLG motion in like two things.

One is

I don't think the problem of the PLG motion is like customer acquisition. I think it's churn. Because like our churn is like 1%. And so I think that like, I think that the nexus of a lot of growth problems is just the business model.

Like your business model is contingent on people continuing to publish content for them to get value from your product. Ours isn't,right? Like Jason, if he hosted with Castos, which he doesn't, which is super unfortunate, but that's okay. If he stopped this show tomorrow, he would still pay $19 a month to keep his show alive.

Otherwise, it would go away. That's not true with you guys. Like if someone stops publishing their content, the value of your solution goes to zero. So there's like a fundamental thing that like you can engineer things to solve.

So like that's part of it. I think the other just comment on SEO, it's super hard, but more nuanced is like you probably are getting a bunch of traffic that isn't qualified traffic,right? So like top of funnel, the bottom of funnel, high buyer intent or not.

I would suppose that like if you said like SEO is the place you want to go, focusing on theright kind of traffic is like the better question rather than like are we doing good or not. But I think like focusing on agencies solves the value of the product and churn issue altogether because as long as they have clients, they're getting value from your product and they're not going to leave because it's also like a core like business solution for them.

Yeah, especially if they incorporate it into the pitch that they give to their clients. Like if it's part of what their clients are now paying for, they can't stop without changing the contract with their client.

This is interesting that this is so steady. I'm actually shocked at this. Like I'm not shocked that it's high because I agree with Craig. That is the problem. Maybe you could convert more from the homepage because the homepage is confusing to me because it's like many different products all at once.

And so I'm confused by the homepage. But so I do think probably there's a thing in conversions to be looked at. We're not going to do all this on the call, but I would say that's an area to look at.

But especially if you have a lot of traffic, then that means A/B tests actually work. So many people, A/B tests don't work because there's not enough N. But if you're getting a lot of traffic, they do work. So that is something we could talk about, but it's probably more tactical.

Strategically, like I am shocked how steady this is at your cancellation rate at around 10% per month. Why is it so steady?

It just increased recently because we introduced the free trials, by the way.

Okay, but why is it so steady for two years? That's amazing. Is it because like it's an annual plan and they just don't, then nobody renews? And so it's always one year. And so one year is roughly 10% per month.

Like what is this?

I think it's very connected with the churn that there is in the industry. So we call this in the industry pod fade. So this is more or less the percentage of people that start a show. And it's true, Craig, you know, your churn is much lower because

it's a hosting,right? So people, even if they stop their show, they still want to show it to their friends. So they want to keep it. For us, people can, even though they can start before,right? So they will start, okay, they start the show.

Maybe they will go even for a free hosting provider, but then they want to use us. But as well, then they stop, then they stop using us. I think it's probably connected to that, I would say.

So 10% per month is something like everyone's gone in a year. I say everyone. I'm being, you know, obviously rough about that.

So is this just another way of seeing the industry? I think you're saying this is another way of seeing the industry data, which is nearly everyone who starts a podcast stops doing it within a year. And you're looking at thatright here.

What do you think, Craig? I think so, yeah, but.

Yeah, I think probably. I think on the whole, I think maybe the one caveat I might give to that is these are, Tiago and João, I don't know, are these new podcasters or existing podcasters who are already have a show on Libsyn or Castos or Transistor or whatever coming over to use your solution?

I think that might be one thing because like for us, a customer who comes to Castos from another provider is worth way more than someone just starting a new show. So that might be like a cohort analysis you might want to do.

But yeah, I don't even think it's a year. I think probably the average life cycle of a customer is like four months probably, like of like actually publishing content. I think it's like whatever. There's a stat, like most shows don't get to 10 episodes.

Right,right.

Yeah.

We can dive into the reasons why people are churning if you want. I have a board that logs this.

Well, it's not just that the show ended.

Mostly, yeah, but I think it could be interesting to see that. I don't know if you want to see it or not.

Let's just go to the next most biggest one because see, again, like staying at the high level, you want to dramatically change the curve, not move from 14K to 16K, 16K to 17K. That's not the goal,right?

Right.

So going to like, well, you know, 15% of the people say this, and maybe we could save a third of them if we did that. See how that's not going to do anything? Because now we're down to 5%.

Okay, we can move your revenue curve 5%. It's okay. Like it's probably a good idea, like all things being equal, but that's not going to solve the problem. So let's, okay, so what's the next? We can still look at it.

I agree that that still might be interesting. So what's the next one or two biggest things that aren't the show ending, which is clearly the issue that you need to reform your company around, like Craig was saying?

So I will share the board.

Let's see, I have a lot of data here. Here you can see per week.

Well, just what's the biggest thing that's not show ending? What's the next biggest thing or two?

In the last week, it seems to be too expensive.

No, I love it. It's too expensive because this is my hobby horse. Do you know what I'm going to say already? Because I say it so often.

It's probably that we are targeting the wrong clients or something.

So here's why I think it's so funny. It's so common that the biggest reason, other than, okay, project ended,right? The biggest reason often is it's too expensive. We see that too at WP Engine, and lots of other people see it.

I've seen other people's data, and many, many people, this is either number one or close. But here's why it's never the reason. Because what did the customer do already? They came to your website, they looked around your homepage, they looked at your pricing page, they looked at competitors maybe, and they decided, yes, I'll buy this for this price, which means they decided it was not too expensive.

They already decided it was not too expensive because they signed up.

Yeah.

And then they were here for four months or six months or a year or a month, and then they quit. Now they didn't quit because it was too expensive. We already know that. Now there's something else which they're saying too expensive, and there's lots of reasons why they would say that.

So for example, they may have thought the product will do X, Y, and Z for me, but it turns out it doesn't, or it doesn't with their other systems, or they don't understand it, or,right, there's all this like misunderstanding or expectations that were missed.

So since the product does less than they thought, it's now too expensive for what it does for them, or the value it's generating for them. And so they say too expensive, but it's not too expensive in the sense that you should change your prices or packaging.

Because when you hear too expensive, you think, well, we'll make it cheaper. But that doesn't solve what I just said, which is they expected the product to do X, and it didn't. Now maybe they were wrong to expect that, and you targeted the wrong segment.

Maybe they were correct to expect it because you said so on the homepage, and you're the one who didn't fulfill it. Like there's so many things that could go, that could be true here,right? So there's still lots of reasons it could be.

But what it isn't is too expensive. That's like the one thing it's not true because they already bought it.

Yeah, I agree. But let me just say something, Jason, by the way.

This reason that too expensive is quite new, and it started since we started the free trials. So I was actually surprised because it's been a while since I watched this. The free trials, by the way, the way it works is we offer a few plans.

We give a free trial in the more expensive plan. So we give the starter plan for very cheap, and then they have to acquire to use it. And then if they want to start with the pro, they have a free trial, okay?

And I can see started growing. The 2X man started growing since we implemented that.

Well, you obviously have to segment this cancellations by that.

Yes. And I do have that as well, if you want to see it.

If they think of this as too expensive, the question is, I'm just going to use Claude, which I think is how some people are saying it's too expensive because I have basically a free solution that I'm already paying for somewhere else.

Claude can make shorts.

Yeah. You could use like Hyperframes with Claude and do it, but you sure enough can do show notes and transcripts.

But wouldn't their customers, I mean, aren't they immediately lost from what you just said?

Yeah, this is, I don't know. I mean, I think over time, like this is becoming easier to adopt.

But we're talking about what's happening now. Like I don't believe that their customers are using Hyperframes and Claude to make shorts instead of using Podsqueeze and things,right? Like you are.

Right? I've even tried doing, I'm trying to do stuff like that, and it's really hard.

It is.

I'm not an idiot about it. I'm not an expert, but I'm not an idiot either. Like it's too hard. So what is the reason in your mind that's obviously not, it's too expensive. What is the reason for the churn that's not, that's the real reason besides the show ending, since we know that's the main reason?

What do you think, João?

The main reason, I guess, is targeting the wrong people. So we have a lot of people coming to the website that just want to transcribe one file and then disappear. So mixed with the pod fade thing, the not using enough, we have actually segmented the kinds of people that are choosing that option when they churn, not using enough.

And many of them, we actually went and see the episodes they uploaded, and many of them were just like webinars and like voice recordings and stuff like that, and they were not exactly podcasters. So the next reason after is too expensive, and the pod fade is switch to an alternative product and quality issues, but these are like a small percentage of the churn.

And in these past two years, we have heard the feedback from the customers. Actually, we have implemented, you said that the homepage is quite confusing because it has a lot of different features, but all of these features were implemented after hearing the customers.

So we had a lot of people asking for clips when we were offering the show notes. So we implemented the clips. And then all the other little features were things that made sense to us to implement in the flow that the users were already using.

And so we could not exactly pinpoint or could not find a relevant pattern

among the quality issues reason.

Okay, so this just concludes to the same thing as we said earlier. These little details are not the main thing.

Yeah, yeah, yeah.

The main thing is you are mostly getting people that either aren't serious users of this. In other words, they're wanting to like use a free trial or use a one-month plan, quote unquote, to do something real quick, which is not a real user that you want.

So that's,right? Or they are sincere in making a podcast, but we know that almost all of them will fail at that, despite being sincere. So while the sincerity is appreciated, that's also not something you can build a business off of.

And those two things account for almost the entire business model.

I must say one thing that I think is very important and something we found out in the next two years, which was the B2B sales that added 2K to our MRR. So here in Portugal, we actually got the main media companies here in Portugal to be our clients, and we are charging them around 400, 500K.

So this is the most we could charge to these kinds of clients. But doing this actually changed our MRR a little bit, and actually most of these clients, actually all of them are staying with us for more than one year.

So none of them churned. We tried to replicate this in other countries. We actually went to conferences in other countries. We spoke to the media agencies and the big media groups in other countries, but we could not reproduce what we were.

No. And do you know why you can't reproduce it?

Why?

Because the reason the Portuguese companies picked you is you're Portuguese.

Yeah, yeah, yeah.

It's not because your product is 10 times better than the competition. I'm not saying your product's bad, and maybe it is better than the competition. I don't know. But I know it's not like overwhelmingly super better than the competition, because there's lots of good products like this,right?

I mean, I think that's probably true of everybody on this call. Castos is a great tool. There's other great tools. WP Engine's great. There's other good ones. Let's be honest. We all have our reasons why, but we're better at this, we're better at that, and for this segment, we're better, and we'reright about that too.

But it's not like it's a shutout. It's not like Linear and Jira, where it's just like, holy moly, shutout time. There's not like 10 tools like Linear,right? But there are 10 tools like Jira. So none of us on this call are in that position.

That's okay. We all are running successful businesses. We don't have to. But my point is just, okay, that's not what you haveright now. Maybe you could build that, but at the moment, it's not it. So there's no reason for anyone else to pick you.

The reason the people in Portugal picked you is you spoke Portuguese to them and you're native and everything, which is a good reason. In fact, it makes me think there's got to be more to do in Portugal.

But I must tell you something. We actually hired someone from Latin America to speak Spanish with the media group.

It's not just that you're speaking Spanish. You're the founders of the company. If I were in Portugal, I want to support a Portuguese company for sure.

Yeah, yeah, yeah. I can see. I can hear you.

Right.

So what are you telling us is that we should have been born American or?

Well, no.

Bigger market.

No, no, no, no. I think you have vastly underestimated how much there is to do in Portugal, number one. And number two, there's just going to be a different move you're going to have to make outside of Portugal.

There's just going to be a different move. It's not going to just be the same thing because you don't have this natural advantage elsewhere. But I don't believe you that 2K per month is the only MRR possible in Portugal.

What are those companies like?

These companies are like.

I'll call them enterprise companies that you've sold to.

These companies are like the major media companies in Portugal that everyone knows about and own the main TV channels and all that stuff. The reason we cannot charge more to these companies is because they pay per podcast,right? They pay per minutes consumed.

And these media companies, the cap is like 50 podcasts. So the maximum we could charge is around maybe 500, 500, 300 per month. And there are not many major media groups here in Portugal. We could maybe count seven, eight, and maybe six of those are already our clients.

So

yeah.

Right, but that's not the end of who does podcasts, including agencies in Portugal.

Yeah, in Portugal, it's pretty much the end.

No, it's not the end. You mean if I go to Googleright now and look for people that will help me produce a podcast in Portugal, who live in Portugal, I can't find anybody? That's what you're saying?

I think you can't find anybody that we haven't talked to already, probably, because you have done all of this.

Or you couldn't find anyone that is producing more than five podcasts or something like that.

We have been cold calling people. We closed a few deals with smaller agencies. It's just a very small market, 10 million people. It's like.

No, that's not the market. That's how many people live in Portugal.

Yeah. I mean, those are the people that consume what these.

No, no, no. People who happen to live in Portugal and are agencies can produce podcasts around the world.

I mean, mostly they don't, but

they mostly produce for the market.

What about like, so you've sold to the public media brand in Portugal.

Yeah, yeah, yeah.

I think what Jason's saying is like the kind of adjacent thing, like podcasting agencies who happen to be in Portugal or big news brands who happen to have a production arm in Portugal or like a big YouTuber who happens to live in Portugal.

Like I know like one of our customers, Bob Dunn,right? Like lives in Portugal. He's a pretty big media brand in the WordPress space. But he's American. There's got to be a lot of those types of folks that are not, I'll use like NPR version from America, but like are pretty big creators.

And maybe it's not 500 bucks a month, but it's 100 bucks a month.

The problem is, again, we don't need someone that has a big profile or has a lot of views. We need people that produce a lot of podcasts. That's where the money comes.

So one issue that we had, by the way, was doing this transition from being a B2C self-service SaaS to a more sales-oriented SaaS, because we would go to them, and this is a learning process. And by the way, this is why I love this conversation.

We are just learning here,right? We would go to them, and of course, we cannot, if they are this big, let's say Joe Rogan, like huge, a lot of money, but he only has one podcast. How can I go to him and say, "Okay, I will charge you 1,000 bucks per month."

And then he goes and checks my starter price. He's like, "But your starter price is 9 bucks. Like why do I need it?" So this was one big issue that maybe you can give me good insights here because it was very hard for us to figure this out, how to like actually have both the self-service and the sales-oriented.

Yeah, I guess I'll leave that question in the air.

I'd love to hear Jason's approach this for my own well-being, but I think I'll just say is you are not an enterprise buyer. So you don't know how they think. I've been on enough enterprise calls to know that just the way they want to buy software, it would make me vomit.

But that's how they want to buy enterprise software. And so I think you have to not think like a bootstrap or trying to sell to enterprise, but think like an enterprise customer who's buying a solution. Because I think you have a pretty severe limiting belief that like my solution is not worth $1,000 to Joe Rogan.

It's 100% it is. But I'd love to hear how Jason thinks about like us as bootstrappers selling to enterprise and like value difference between like self-serve and like whatever, sales-driven.

Yeah, there's a couple of things here. One is Joe Rogan's not enterprise.

Microsoft is enterprise. And perhaps the major media brands might be enterprise in Portugal. Enterprise refers to the company and how they buy and think. I guarantee you Joe Rogan does not think in any way like those media buyers think.

So that's the first thing is like you got to separate what is the company, what is the way that they think about software, buy software, just like Craig was saying.

So

the issue with pricing for everybody is very real, which is why generally you don't do it. It's not true that companies generally sell $9 a month thing and also sell multimillion-dollar packages to enterprises. In fact, name me one.

Name me a company that does that. I can. Try it.

Slack? Riverside?

Slack? Riverside does not sell multimillion-dollar packages to enterprises.

Multimillion? Okay.

Yes, multimillion a year. Slack is large.

But they do sell a lot to enterprise, I would say.

Yeah, but they don't charge $85 million a year,right? But Slack does. So Slack works because Slack has both features that they need, special features that they need and will pay up for, like auditing and all kinds of weird legal stuff and control over things.

And there's an issue of seats. It makes sense for Slack to charge by the seat. It makes sense for 30,000 seats to cost a lot more than five seats,right? So there's two dimensions by which Slack can charge more to enterprise and make sense.

So for Slack, it makes sense. Another example would be cloud compute,right? A startup might pay zero because of a special offer, but let's even ignore the special offers. They may pay a dollar a month because they use so little, but a big enterprise might spend $100 million a year on Amazon because they use a lot.

Because again, usage in that case, not monthly, but usage now makes a whole lot of sense because it does cost a lot to use it. Like that's just true,right? So I can come up with companies where they can charge $5 a month to some people and $100 million to others.

There has to be a really good reason like that. Usage and maybe also like the features on top of that, like Slack has both. So you roll back to you and you're like, "So do you have that?" And the answer may be yes or no, or maybe we should construct that.

But when you can construct that, and just saying it's custom doesn't construct that. There has to be some specific reasons. So for example, with hosting, there's all this security and governance stuff. People often say security when they mean, well, they don't know what they mean.

They just say security because they don't know. But it's security, but it's also what's called governance, which is things like being compliant with something like a 409A, or I mean, not that. Sorry, being compliant with something like

SOC 2 or an ISO standard or HIPAA in the US for health and so forth, or sometimes just financial compliances. That's not security. That's governance, meaning you've defined certain processes and you've addressed certain risks, and it's all documented, which is not the same as security, interestingly.

So an enterprise who looks at hosting cares about that because they have internal policies requiring them to care about it so that their own governance is satisfied because all their vendors plug into it. And Joe Rogan doesn't care about any of that, which is again, why the size of the deal or how much the money they make or whatever it is, is not the same thing as what kind of company it is and how they buy.

So all those kind of things probably don't make sense in your case. They're probably just not relevant. Maybe they are. Maybe they are, but probably they're not. And so an interesting question is, what does it mean to have usage, or what does it mean to have features?

Because those are the two dimensions that often make sense in a pricing grid. I think of it like usage on one axis, features on another. In your case, you might say, "Look, it's not that complicated. We're just going to have one axis where it comes together."

Bigger plans have both more usage allowed and more features. And that's fine. Slack kind of can afford, you might say, to have two axes. Zendesk is another example where you buy more seats and/or you buy more features separately.

So these companies, it makes sense. It's very natural why there would be both. In your case, it may or may not be natural. And you don't have to do any of this, but it's an answer to this question of, "Wait a minute, how do I have radically different prices?"

It has to be tied to something that the customer values and requires, which can again be features or usage or ideally both. That's the best scenario, but not required.

So we thought a lot about that, a lot. And the only thing we came up with

was per podcast. So we would go to them and say, "Okay, for every new podcast, you get seats can also be a possibility, by the way, because normally they have a lot of people working there, but we would think of four podcasts."

We ended up not implementing that. What we implemented was basically giving unlimited minutes. But that, again, this goes to the minutes, and we say, "Okay, finally, you get unlimited minutes and plus support." You can see their priority support, feature requests, try to sell this and package this into an enterprise deal.

That's not really what though. You are not really listening to what they need. There's no enterprise that says, "Oh, I'm going to buy that one because it has feature requests."

Yeah. I mean, but they need the pro, the agency,right?

I'm just saying, you have your enterprise pricing up and it's like, "Oh, you get now priority support, yes." You need to define that somewhere, but yes, that is the kind of thing that larger companies will pay for. So I like that.

But feature requests, I don't know what that means. Does that mean you implement anything I want? No. So it just means I can ask. Anyone can ask. It just doesn't mean anything. You're just making stuff up.

It's not what the customer is saying.

And that's why that doesn't make any sense.

That's true.

So here's something interesting. It's very important. And I think Craig was getting at this too. You, of course, were thinking things like, "What are my costs?" Because obviously pricing has to cover and then some costs. And you're also thinking, "How hard is this for me to do?

Or how much work was it for us to do?"

Now, the customer doesn't care how much work it costs you. They care about how much value it is for them. What's the alternative for how they do this if it wasn't for you? That's what they're thinking. They don't know how much effort it took you.

They don't care. Cost is kind of in between because if it costs you more, they kind of understand that. Like another podcast, more AI, more everything, it just sort of stands to reason that would cost more. Without spreadsheets and numbers, it just stands to reason.

Same with hosting. This site has 100 times the traffic of this other site. Okay, it should cost more. Maybe not 100 times more, but maybe 100 times more. But anyway, it should cost more. That's just reasonable. I just expect that somehow.

It just makes sense,right? So cost is there. That's okay. It sort of justifies it. But the main thing is, what is their alternative and how much value are they really getting out of it? So if all they do is transcribe it and it just sort of goes on a page and nothing really happens after that, they've just ticked a box that said has transcription, that's almost no value.

So they may be willing to pay a little bit for that, but not much. And if there's another alternative that comes along, whether it's CloudCode or a competitor, fine, because who cares? I'm just ticking a box that says we have a transcription.

I just don't care. Now, on the other hand, if having great transcriptions means their SEO is so dramatically improved that they actually increase traffic to the websites or increase listens or something like this, and they can see that, now it has a lot of value.

No, it probably doesn't have that much value. I'm just trying to say, if that's true, then it has a lot of value. If not, then it's just a bullet point and it's not a reason to buy. It's not interesting.

You're never going to win against competitors because nobody really cares. They're just ticking a box. Same with shorts. You cut up in shorts. We all know there's 100 products, maybe 1,000, where you feed in a podcast and it cuts up into shorts.

We know that. So is it just to do it? Is it to drive traffic? Does yours do it better? And if the answer is like, "I don't know, it just cuts it up in shorts," like, "Okay, well, then it doesn't have a lot of value," because you're saying it doesn't.

Can I ask you a question, Jason? How do you figure out what kind of feature ticks that criteria?

Yeah. What we did is we called a whole bunch of customers. And we did some surveys too. With pricing, we did a variety of things. With pricing, we did some surveys and some calls. Calls are always better, but of course, they're so much harder and take more time.

It's okay. And you can look online, and there's good books actually also about how do you structure a pricing call in particular,right? There's a whole lot of best practices around there. So we don't need to get into that here just because that's findable.

But what you're really looking for is what is it that they feel is a good unit to buy? So in your case, is the unit a podcast? And they're like, "Is it easy?" When you say like, "If you were to add another podcast, if that was an extra $5 a month, how does that feel?"

That may or may not be theright exact question. Again, I don't want to get into the details of that because there's other experts for that. And if that's easy, they're like, "Yeah, of course. If I had podcasts, I expect to pay more."

And now we're only arguing about how much,right? There you go. But minutes might be something. And again, I don't know if this is true. You'd have to find this out. And in fact, maybe Craig knows. But with minutes, I could imagine something like this.

Let's say you wanted to charge by how many minutes processed or something like this,right? Where someone could go, "Oh my God, I'm going to have to start counting the minutes. I don't know how to budget for that. I don't know what my bill will be next month because I don't know how many minutes I'm going to like, 'Oh my God, you're just putting all this on me.

I don't understand.' Just I have a podcast." Now, you know minutes is somehow correlated with cost. So you'd like to put minutes on there to cover your costs. And you're not totally wrong about that. But the way you should be thinking about that is, whatever your costs are, plus, of course, profit and blah, blah, blah, that's the minimum you can charge.

You should just think of it as the minimum. Because if you go below that, you're just not profitable or whatever,right? So it sets a minimum internal bar in your mind, but that's not how the customer thinks about it.

So it's just for you. For the customer, it's like, "How do they think and how do they want to be how do they want to be charged?" Because of course, they're willing to pay for value. The ones that aren't aren't good customers anyway.

So of the ones who are,right? And so if in their mind, it's like, "Yeah, I have a podcast. I'll pay for a podcast." Then in your mind, you go, "Okay, well, I know what the median podcast is or even like the 90th percentile podcast is in terms of minutes."

Because we all know some have a lot of episodes, some don't, some are long, short. I know. They're not all going to be the same profit. It's okay. But like in general, the 90th percentile podcast costs you XYZ, blah, blah, blah.

And so if you charged whatever per podcast, you're going to be fine basically all the time,right? And then you could say something like unlimited minutes, which is awesome. Or you could put a super high limit, but again, if the limit's going to be very high and the customer doesn't value it, unlimited is a very strong thing to say because you will have, again, in my hypothetical, you will have figured out the customer doesn't want to think about minutes.

Ooh, if they don't want to think about minutes, then give them that by saying unlimited minutes. And then if they're like, even begrudgingly, like, "Yeah, of course, if I launch another podcast, of course, I expect the bill to go."

Okay, well, there you go. That's where you do it because they agreed. That's a natural thing that they would expect. And anyway, they think it's fair. So I'm just guessing that that may be kind of what they're thinking.

I don't know that. But this is actually one of the things that I think is horrible about cloud compute is that it's all about usage,right? It's all tied to their costs. And everyone hates it,right? The only reason they don't go somewhere else is because everyone else does it the same way.

But that's one of the nice things about DigitalOcean is they're just like, "Hey man, here's a VPS. It's 10 bucks a month. The limits are pretty good. Let's move on." It's like, "Yeah, that's so nice,"right? That's like a big advantage of DigitalOcean.

And there's whole companies whose product is to help you understand your costs in the cloud because it's so freaking complicated. So that's like the worst-case scenario,right? Now, I know you're not doing that. I'm just bringing that up as an example of the worst way to price that they do,right?

So anyway,

so yeah, you sense out with your customers what do they feel is kind of fair or expected in terms of what things, whether that's features or usage like podcasts. And seats is a good example. My intuition is don't charge by seat because the more people that use your software, the more you'll have things like word of mouth and just more usage in general, including when people leave company A and go to company B, they take with them the knowledge of your product.

And that is also word of mouth in a funny way. So the more people that use it, the more you can grow. Anytime I think of a feature where the more people use it, the more you'll grow, I don't want to gate that.

I don't want to limit that. I don't want to charge for that because that's helping you. That's like market share, mind share, whatever you want to call that,right? So anytime it's like, "Wait a minute, that's helping you. Don't gate it.

Don't charge too much so that not as many people know about this. That's bad." But more podcasts, okay, that's probably just normal course of business, as you say, for an agency or maybe a bigger something or other. So that's where it makes sense.

So obviously, everything I said, each of these things in detail might be incorrect in your specific case, but that's the mentality. That's the model I'm going through of like, "What do I want to charge for and what do I not?"

Same thing with your I know I'm just going on and on, but just so I don't forget, same thing in trial period. Anything in the trial period that they really value, you should charge for that. But anything in the trial period which helps you with the word of mouth and stuff I just said, you should not charge for that.

So that you have more people doing whatever that is,right? In fact, you might even allow people to continue using a trial if they're referring people successfully because that's another way for you to grow that allows them to offset how much you're charging them because they're giving you value in a different way, which is not just spreading the word, but doing so in a way that's resulting in people buying.

Now, that probably wouldn't work. I don't know that that's the first thing I would do. I'm just giving an example of what I mean by even in the trial period, give away the stuff that adds value to you or growth in the company.

And yeah, one thing that is interesting here from our experience with B2B. When we first started, again, for the Portuguese people listening, I don't know if there are any people here in Portugal, mostly they don't want to pay,right?

It's kind of more poor country mentality. They always say it's too expensive. So when we first started, we started very cheap in big companies. And then we sat together and said, "This was a mistake. It's super cheap." The next year when they renewed, we said, "No, now let's charge them properly."

And funny enough, they didn't even question. So that was incredible because I told them, "Okay, here's the new price. It's five times more expensive. You get basically a little bit more minutes, something like that." And they said, "Sure, just bill me or send me the invoice."

So this was incredible for me to realize that at some point, they don't really care about the price, especially because the person signing off on paying is not the person using it.

Well, that's what Craig and I have been saying. Now, here's the thing. So you quintupled the price and they said, "Okay." And so what are you going to do this year?

I mean, I guess there's a limit,right? I cannot keep.

Are you anywhere close to the limitright now?

Again, sorry, I didn't hear.

Are you anywhere close to the limitright now?

I don't know.

Yes, you do. You just said you raised the price 5x. They didn't even blink. If you were at the limit, they would have blinked. They'd have said, "Oh my gosh, I don't know about that. Look, I get it.

You got to charge more, but I don't know if I have budget for that. Let me get back to you," blah, blah, blah. And maybe they still would have paid, but blah, blah, blah, blah, blah. If they're just like, "Okay, anyway, is that it?

Because I got other things to do," then you see how you're nowhere close to the limit.

Now, that doesn't mean you quintuple again necessarily. Maybe you double.

You could suss out what this means. But what it means is you're nowhere close to the limit.

Right. Agreed.

Craig, I think I've cut you off a few times.

No, no.

Go for it.

What's

a little painful, but so interesting is the reason I like this kind of format so much is I see my business in this discussion a lot. And

I think this applies to many people who will listen to this show is selling a $9 a month thing is very hard to grow a substantial business. We have thousands of customers and very low churn. And we're not growing either.

It's really hard. I think the answer to all this and Jason, I think this is interesting in this discussion. We're talking about like, "Oh, should we price this and what's the value metric and all this kind of stuff?"

I think that none of that is the issue. The issue is who is your customer? And your customer are agencies or media brands. They're the same, let's say. It's not the individual who has a podcast. And so if I'm looking at this, I'm like and I'd love to hear how WP Engine did this because you sell to both.

We were a customer of WP Engine before we left WordPress. It's great. Also, a shit ton excuse me, a ton of

hosting providers would essentially white label WP agencies, marketing agencies would essentially white label WP Engine for their customers and pass the costs through and stuff like that. But because to me, I think back to the very first graph of flat revenue and high churn that's very consistent, let's just say, and this is no shade at you guys, you can't make this business work selling to individuals.

Let's just say that,right? Unless you add 5 million followers in a podcast or a massive YouTube channel or some kind of unfair marketing advantage that makes top of funnel so enormous that that 10% churn just doesn't matter. That's like a huge outlier in the marketing world, but I don't think I don't, and I don't think you guys do.

And so you have to just sell a more expensive thing to stick to your customers who stay longer and they're less of a pain. That's the whole thing. And there's a lot I think the macro thing in SaaS is

that unfair advantage used to be easier to achieve through content marketing and SEO. Now it's really super hard. And so that alpha has eroded for a lot of a lot, a lot, a lot of us. When I talk to all the tiny seed companies, a lot of us are struggling because that was our go-to-market motion.

Maybe it's not really marketing. It was like we were lazy and bad marketers, and that was kind of cheating. But that opportunity is kind of largely gone. And so a lot of us should be looking at like, "Okay, I need to change who my customer is, sell stuff to them, charge more money, and not rely on me typing words in Google, sending me free leads who are kind of like not amazing customers by retention and metrics perspectives."

But Craig, by the way, this is great because also one of the reasons why we wanted to do this is to get the confirmation for a lot of things that João and I already kind of think we know.

And this is the first one. And I would love to hear Jason's opinion as well. So do you agree based on this information, of course, which is not a lot, that there is nothing major we can do that will double our MRR for the, let's call it, B2B self-service?

I mean, it's hard to say never, but I think it might be easier to say you would be fishing in a difficult pond, so you had better be amazing fishermen. It might be smarter, more strategic to be in a pond that's just a better pond in the first place.

You still want to be the best fisherman you can be, but why are you making it harder for yourself by being in an almost impossible starting position? Because I think Craig isright. Again, it's no fault of yours, and it's not saying in fact, I think your data shows that your product is good and works.

That's what I think your data shows. I think what your data shows is there's a whole bunch of noise in the market either because of people kind of abusing what you have for their own stuff, which is fine.

Again, that in itself is actually not a problem. You would just ignore those metrics and you say, "Allright, some people join for a month, they do some transcription and leave." And you know what? Who cares? As long as we're not talking to them in tech support, it doesn't matter.

Of course, that's not how we're going to build our business, but we're also going to ignore it because it doesn't matter. So there's all that. It just doesn't matter. And then there's this huge chunk of people, which is most of them, that generally want to start a generally want to do a podcast, but it doesn't work out.

Once again, you're fine with that,right? You just don't want to focus on them. That's not how you're going to build your business. You're not going to make features for them. You can't stay on tech support a long time with them.

They're going to have to just figure it out on their own. You can get great knowledge base. You can set up an AI for them to answer questions. You can answer maybe some questions a little bit here and there, but in the main, they need to just be on their own because it's just not going to work out.

And that's what we did, by the way.

Yeah, yeah. So that's fine. There's nothing wrong with that, but just that's not where the healthy business is,right? And so it's in.

Because the market is small.

You multiply the price by five for essentially the same product, and they go, "Who cares?" That's the best market for you,right? Obviously. Now, there is an exception. So it's fun to talk about, well, what would it look like if this self-serve high churn market worked?

And a good example is Shopify, but you have to ask what else is true about the product or market that makes it work anyway? Because Shopify's cancellation rate is 7% per month. Now, yours is much higher, so okay.

But still, 7% per month is ludicrously high for a company of their scale. If you just heard that, you would think, well, there's no way they could be big, even though, of course, yes, they are. They're enormous and very healthy, very great company,right?

But 7% per month cancellation rate means that at the end of one year, one-half of their customers have left.

See what I mean? That's terrible. How could they become a big company if half their customers leave every year? What the heck,right? So that's what I mean. That should be too much. However, what else is true about their business and business model, some because of the market they're in and some because they're excellent at their business, that offsets that?

Well, one is there's an enormous constant inbound. There's always tons of people starting a new store. So it's just a tsunami of inbound. And they're known as the best place to do it, so they get a lot of the inbound.

Okay. So they have this huge inbound. So even if a lot of them die off, oh boy, it's just the end is so big that even if a trickle stay, that's still good,right? You can almost think of this first year as a trial period that's paid for,right?

And when you think of it that way, you're like, "Oh, well, if it's a trial period that's paid for and the end is enormous, okay, now I'm starting to see why it works." And here's the other piece of the people that do stick around, they generally grow every year.

And so whatever that amount is.

And the biggest share.

It's not even 50. Let's say it's 25% that sort of stick and really grow. Yeah, but when the end is big and then those people just grow, grow, grow, grow, then you're just stacking growing customers and growing, growing, growing and stacking them.

And that is an insane growth engine. So why does it work even though they have, let's just call it high churn, quote-unquote, like you have in a market where most people who start a store fail, just like most people who start a podcast fail?

And let's ignore the detailed numbers. Those are still true. But the reason it still works is, one, inbound is huge and consistent. And two, those who stay then grow in their revenue. And therefore, really, it's like a big paid trial period and then this big growth engine underneath.

Okay. So is there a way for you to be like that? I don't know. Again, if I had to bet and I were you, I would rather fish in a better shaped market. That's what I would do. But could you say, "Well, we have okay, we're not Shopify, of course.

We don't need to be Shopify either. That's not the point. It's just a great example of the mechanics,right? But maybe we do have enough of those pieces like Shopify because we do have a lot of inbound thanks to our SEO and the fact that people start podcasts.

And yeah, we have high churn, but the people that stay make a podcast and it's important to them. Once they stay, it's an important marketing thing. That's what it means to continue is that it's important to them. Okay.

But what we're missing is the piece where they grow. So we don't have that piece of the Shopify business model that I said in my little reductive analysis here. We don't have that part. If we did, if of the, let's call it 25% that really do make a podcast and stick, it's probably not even that high, but okay.

I'm just making up numbers. If they grew how much they're paying you by between 25 and 100 percent per year every year on average, you'd have a decent business all of a sudden,right? And these bigger customers, if they were doing that too, okay, so once they're at a bigger number, they're not doubling every year, but whatever, they're growing a little and they're at a bigger number.

Now it's interesting. So you could go and maybe we should, I think, talk about the better market as a good use of our time here probably, but I think as an exercise to come away with for you guys.

No, but it's good.

To explore this option of, well, wait a minute, could we I mean, and again, I don't mean to say copy Shopify, but I'm just using that as just a name for that. Is there enough other things that could be true about this low end that would make it good that we could actually do?

And again, my guess is probably actually, if you explore that option, it won't be as good as other options. But I think you should explore because maybe it is. And also, maybe if you chose a second option, you could say, "If we implemented some things for this low end, maybe we could get it from 15K to 20K, 25K, and that would matter."

That would matter.

And so we can't afford to spend a lot of our time on that because we need to go to the better market. But if we could spend 10 to 20 percent of our time on that and maybe, in fact, double that business or add another 10K of MRR on that business with 10 to 20 percent of our time by adjusting some things with that new mindset.

I don't know. Maybe that's not a bad use of 10 to 20 percent of time. Now, I generally like to say you guys are too small to split your focus on different things. And I would say it's better to just pick one option and put all in.

Yeah, I agree.

But I know you guys, especially you, Tiago, are guys that like to do many things at once. And so I would say rather than more different projects that have nothing to do with this, which I think is a bad idea, sorry.

I think if you want to spread your attention on different things, maybe this is a better way to spread your attention. Spread it on different segments and ask what's best for that segment. I still think it's not a good use of your time.

But if you've got to if you insist on having different projects, I would suggest that's a better use of your time.

It's a great idea.

One thing that's.

And then.

Sorry, just our own data that might be helpful here. We have almost no expansion revenue, which is kind of like what Jason's talking about. We have almost none. Our pricing is on downloads in one and features. So we kind of double value metric, which is not how I think it should be, but just what we do.

You guys kind of do too. The only expansion revenue we see is people upgrading plans based on features. And so I think what's interesting with your pricing model, and again, I think this is not the lever to pull,right?

But I think what's less and that we could abstract away to other people listening or watching is your value metric is minutes, largely, from a usage perspective or podcasts, which very few people in podcasting would increase the amount of minutes they publish.

Like Jason, you're going to publish this podcast every week or every other week. You're not going to suddenly do one a day.

Yeah.

That would be amazing, but you're probably not. A show might be more successful. Usage would go up, which is like cloud compute or traffic on a website if you're a WP engine or something like that. But rarely, and so I guess the takeaway for other folks is don't bet on your expansion revenue value metric being a thing that a customer is unlikely to do.

Right.

It's like Shopify is very aligned. A show or a store sells more stuff. They pay Shopify more, but not opening more stores or something.

Yeah. And this is really interesting. One thing that came to my mind is, and what a lot of people in our industry do is to. So yeah, minutes won't grow, but listens might grow,right? And how do we make money from our customers having more listeners?

And normally, that's with ads,right? And that's actually, Craig, you're in a better position than we are to explore that,right? And you have ACAS and these kind of players that they say, "Okay, we will give you the ads. We get a percentage.

And if your show explodes, we get a percentage." So maybe or something kind of Patreon-like, but again, it's a very divergent type of features. We would go to a different place, but it makes sense in a way.

Here's, I think, still there's a confusion that's happening here, which

that makes it sound like you're confused and that you're not good at this, but everyone does it. Also me. Also, we did this so many times at WP Engine. So I just mean it's a confusion that happens, okay?

It's not an accusation. It's a fact, okay, of all of us, allright? Which is we're still confusing. What is the customer value that you do for them with you want to make more money off of certain kinds of customers?

So in other words, even these minutes, I don't understand that. I would understand something like the more minutes there is, the more transcription costs are. That I get. Listeners, though, what does that have to do with you? Now, maybe in your hosting side, and again, this is why I'm a little confused myself because you have a lot of different products, and yet I don't see different products on this pricing page.

So that is a little confusing because if you're charging me for listens because you have a hosting page, but I'm not using you for that. I'm using Castos for that. I'm using you for this other for shorts, but then you're charging me for listens.

That doesn't make any sense. You see what I mean?

No, but that's not what I meant, Jason, though. What I meant is we could use this.

But

I don't want to

if your shorts generated more traffic for me, I want to pay for that because that's the value I expect from shorts.

Yeah, yeah.

Right? Now, you may not be able to track that. That may be a bad something you can't actually measure and do. So fine. But I would certainly more podcasts. I mean, you'd have to find out, but I've got to think that someone would agree that every time there's a podcast, there's a whole bunch of stuff you do for it.

It should cost more somehow. The minutes, though, it's just like, what the hell? What difference does it make the minutes? And if you say, "Oh, but I just want if they're a big podcast, I just want them to pay me more," I would say, "Okay, I hear that."

But that's not the metric that they value it. So somehow, what else would a big podcast need where they would pay you a lot? And it's probably more like features. A big podcast needs certain features that a little podcaster doesn't even know they need or something like that or doesn't occur to them or whatever.

And it's probably something more like that where your desire to charge the big guys more money, which I agree with, and you'reright, needs to be aligned with what they want to pay for. And so if those are misaligned, you'reright.

You're charging big guys more, but not in a way they like, and that doesn't work.

Yeah, I got it. What I was trying to say is that I was brainstorming some ideas to find a more kind of Stripe model where Stripe, the more money you make, they take a percentage and they get more money.

So I was thinking, let's say we would sell ads. So the more ads, so most of the money would go to our customer. We are connecting them. So that's why I said it's a different type of model, but it could make sense in this industry because even though it's not a big industry, some people get really big.

So if you could get a percentage of that, not by selling a different feature, but by selling ads. That's what I meant.

Once you get big, you don't outsource ads once you're big, isn't thatright? Maybe Craig knows.

Yeah. I think that's I don't know. I don't know.

Yeah. I don't know that market, but I think my understanding is it's small people that want to do that because they don't have buying power. And it's when you get big and have buying power, what you don't need is an agency taking or just some random podcast software company taking 20%.

So either you're going to take it in-house and keep all that money because that's your revenue. It's a huge amount of money. Or you're going to use some agency that's actually good at it, which you guys are not.

Yeah, but you have, for instance, Patreon or Buy Me a Coffee type of model, which.

Yeah, they don't need you for that. They just have a Patreon. What do they need you for?

I mean, you can't compete with them,right? You can compete with.

Yeah, with Patreon. No, come on.

Yeah, I would say that's a worse if we're stacking up business models, that's worse than your current one, which is like beta prosumer. That's kind of entrepreneur type, which is because we do a bit of that. And I'll just tell you, on our entire platform, we have one customer who makes $100 a month from ads or more.

Oh my God.

Yeah, it's very little. Yeah.

There's actually another trick we could do that I've seen other platforms that create content doing is charge for

usage rights. So for example, we could charge if you have a podcast and you have an audience for 10,000 people, for example, we charge a fee to use our content. And for these enterprise media organizations that use our content for their websites that have a lot of traffic, we could charge

a usage rights fee. I don't know if that makes sense to you.

I understand what you're saying. I just personally have no experience with that to know if that's very exciting or not and what their alternatives are or not and so forth. So I just don't know how special that idea is.

But anyway, what you guys are doing, I think, is still theright way of thinking about it, which is, okay, is there something that could grow as the customer grows or grow as the customer has more value in their podcast?

What I mean to say is that would grow as the customer values their podcast more. One way in which they might value their podcast more is that it grows in downloads. But since we all know that usually doesn't happen very much, I would actually encourage you to think about when people care about it more instead.

For example, I don't make any money off of this podcast, and I don't care. I don't run ads. I don't want to run ads. I want to see the best and most really just a genuine, authentic conversation and not have things like ads and not have it be produced and I don't have any freaking

special effects during the day. I don't want any of that. I just want it to be this. Now, will I ever get big? I doubt it. But as I get more episodes, I care more about it, and I might want more stuff.

I actually should do shorts. I don't know how to do it. And oh my gosh. But I probably should do that. But my first episode, I did. But then eventually, I will,right? Or once there's a corpus of, let's say, 50 episodes or 100, I bet there's stuff I should be thinking about or doing at that point that don't make sense now when I don't have that many out yet.

And I don't even know what that is, but maybe I should do that. And I would pay more to have that thing done, whatever that is,right? And so it's not necessarily downloads. And maybe it's number of episodes. That might be actually better.

Maybe that shows the maturity, longevity, and that means I want or maybe not. I'm not entirely sure myself because I haven't done it. And Craig, and actually you guys probably know, but it's this general concept that I'm trying to get across of

when the customer cares about their podcast more, what will they want so that you can give that to them for more money? And that's why they upgrade. And it could be things like listens or downloads, but it could be other things and other things that they want.

And when you charge by the listens or downloads, of course, as a hosting company, it makes sense to charge by downloads because now it makes sense why that's proportional to costs that my vendor has. So now it makes sense to me.

When it's shorts, making shorts, it doesn't make sense to me. Who cares how many listeners I have if I'm making shorts?

But whether I can make shorts or not, well, yeah, that makes sense. Here's a plan where I can't make shorts. Now, I'm not saying you should do that because that's probably the wrong division. But if that were the case, oh, that would make sense.

This feature of making shorts with AI and it's like, "Oh, yeah. I mean,

I understand why that would cost more." Maybe in the free trial, you find the areas where shorts would be smart. And then when I pay, you actually can make the shorts and put the text and say, "Four hours later," and all that shit.

And that's what I pay for is that you actually make it. Maybe that makes sense. I don't know,right? But I'm just trying to emphasize this thing of where the customer values it more, which might be a usage metric, but might not.

And how do you align the features and things to that? And then we should continue talking about these particular plans, actually, and also this thing about agencies because that's still, I think, the answer. And at least that's what Craig is saying too,right?

And that's where you haven't even found the limit of what a big one will pay. And duh, isn't that a huge signal? You haven't even found the ceiling yet.

What are you guys?

Maybe you should find it.

What are you guys doing to sell to agenciesright now besides this custom plan on the site?

So what we've done, we've tried a lot of things. We tried cold calling. We tried cold emailing. We tried none of this really worked. What worked, but again, maybe that's because we're Portuguese. That's what we're trying to figure out is we go to conferences and we just demo the product to the people.

And obviously, we go to conferences where relevant people are, people that are working in these media agencies or newspapers and companies, and we show this to them. And then we go through the full enterprise cycle of, "Okay, do you like it?

I will get you a trial so that you can try it out." We will accompany the full process. And then eventually, if they like it, we convert the sale. But it takes months. So it's a big investment from our side, first of all.

And second, we haven't been able to replicate that outside of Portugal. So those are the challenges, I would say.

Any ideas?

I mean, I hate to ask an obvious question. Why do you think you haven't been able to replicate it outside Portugal besides the fact that you're Portuguese? Is there something else?

We actually, as I was mentioning, we hired a girl in Latin America. And we connected, I guess, with almost the same as we did in Portugal. We connected with the major companies in countries like Brazil and other Latin American countries.

And we actually went through all the phase of connecting with them, demoing,

chasing them, trying to collect the feedback and all that stuff, but we never reached the point where they converted.

That's because what?

Sorry, what?

Because why?

Many of them just, I don't know, maybe Tiago can

say a little bit more.

I think they never really tried.

Okay. And why did they never try?

They're busy. I don't know.

But they took the sales call.

They did.

Well, you don't take a sales meeting. I get cold emails every day for crap. I don't take the meeting. I only take sales calls if I'm in the market to buy it. Now, it's true, they may just be exploring and they didn't have a serious project.

That is possible. But when it's 100% failure rate, that doesn't explain it, just that every single person didn't really have a project and was just curious. That's not the case. So why did they take the meeting and then decide not to proceed?

Well, part of the.

That's why I'm here to figure out.

Well, you can't ask me because I wasn't in the meeting. So first of all, you can't just if you yourself don't know how to sell the product, then you can't just hire someone in some other country and hope that she just figures it out.

That's true.

You could do that if you hire a really great person who knows how to be the first one into the sale. In other words, sorry, you can do that if you there's certain people you can hire who can build a sales organization from zero and figure out how to sell it and then sell it.

That's a very special kind of a hire. Most people can't do that. Shoot, most founders can't do it and their companies don't work,right? You guys haven't been successful yet in doing that. There you go. It's very hard. It's a special skill.

It is.

So yeah, so it's kind of not surprising unless you had a very special hire.

I think part of the reason was, well, first of all, sending emails didn't work. So we had to be a little bit more aggressive. So what we did was having this person that we hired messaging people in certain departments in these companies directly through WhatsApp.

And so connecting really personally to their phones. After we connected, we did a demo with that person. So maybe that person wasn't really the decision maker, but it was the relevant person, at least from our understanding, that could be.

But you're still not answering what? So why did they take the meeting and do all that stuff and then never talk to you again?

Yeah, so then they did the meeting.

Why did they never talk to you again? Just what is the answer?

But they did. They talked with us again. Actually, Tiago was chasing them for.

Okay, and then why didn't they buy? Just what's the answer to why, despite this interest, they didn't do it?

I guess the real answer is probably they did not see immediate valueright away. And they were just too busy doing other things. And it wasn't just worth for them to spend more time experimenting the product. I guess that would be the real.

So you're saying they did experiment with the product or they never did that either?

No, no, no. I think they did.

We mean you think they did.

Sorry, what?

What do you mean you think they did? Did they pay to get an account and use it, or did they not do that?

Yeah, yeah, yeah. We did the demos. They had an account. They converted a few episodes, but it never went beyond converting maybe two or three episodes.

Okay, so the product didn't do anything valuable for them, so they didn't want to continue?

Possibly, yeah, yeah.

What do you mean possibly? If it was valuable, why would they stop?

I guess that's the reason, but again.

I'll tell you why there's this confusion. Because we have the same with the Portuguese folks, where they would start and then they would I guess, I don't know, you probably know this better than I do,right? In these enterprise things, they have so many things going on.

And then they would start and then they wouldn't put the focus on it. And then only when we actually went to this enterprise and we met them and we created a connection, then they say, "Okay, let me really put focus on my team and myself."

That's just what sales looks like.

But how can you do this as a bootstrapper?

Generally speaking, a person at a larger company has a couple of priorities on their desk. It may be their quarterly priorities or something like that. Sometimes it's an emergency,right? So sometimes they're like, "For this quarter, I've got two things I got to do that my job is depending on.

I'm being measured by. We're talking about every week in our stand-ups or whatever,"right? There's usually just a couple of things at a time that a person at enterprise has. Now, they may be attacked with a dozen things at all times, but that's not affecting their job.

If they dropped one of those and said, "I'm too busy," they don't lose their job. But there's usually one or two critical priority things where if they drop that, that's their job,right? Now, when you're one of those, you get the attention.

And if they need to get shorts up, they are going to buy something to do shorts if it's one of those things that's like, "This is my job. I have to get shorts up this quarter. That's the deal."

If it's one of those. So when you're selling to someone who's in that position, this thing of like, "Well, I don't know, I moved on," that doesn't happen. The reason that happens is what you're describing, which is very common, which is sure, they'd like to do shorts.

Sure, they'd like to have the transcript, whatever. It's all night. Sure, all else being equal, they would take that. That'd be good. But it's not one of those top one, two, maybe three things that's on their plateright now.

The other thing that happens is emergencies. So you often start the quarter with one, two, maybe three of these things. But then something happens in the middle and you're like, "Oh, I have to do this,"right? And that becomes one of them too,right?

And they have even less time for other stuff or maybe one of their other priorities gets pushed. Often happens,right? So it's their priorities, and I'm including emergency priorities in that bucket of stuff. So if you're in there, this doesn't happen and the sale works.

And if you're not in there, then people will say you'll experience exactly what you experienced. This is the symptom. What you're seeing is the symptoms of this disease, where the way I put it is, if you could just have this for free, and by free, I don't just mean money.

I mean your time. I mean if just magically this just happened to all your podcasts and you never thought of it again, it just happened. Do you want that to happen? And it's amazing how often the answer is still, "No, I don't," in which case that's a product.

See, and if that's the case, we got a more fundamental problem with the product,right? I can name products like that. For example, if I said, "Here's a new email product from a vendor you've never heard of before. I'm going to move all your email over there and you have to use them for email from now on."

You want that? It's free. You would say, "Wait, no, no, no. Email's very important. I don't want you to just give it to some random person." No, no, no, no, no, no, no. Hold on. No, no, no. Email, no.

Not even for free. See what I mean? So it's not necessarily okay. So in your case, probably the answer is, "Yes, I'll take it for free." And I mean free in this broad sense, yeah? So that's why they take a meeting.

In this case, if when they would take it, if it were free, but it's not one of these priorities, then what happens is they take the sales meeting, they take the demo, they might even try it, and then they don't buy because it's not one of their top priorities.

So my guess is that's what's going on because this is the symptoms of that disease.

Right. How do we fix it?

Now, this could be now, here's another question though. They didn't buy from you. Now my question is, did they buy from someone else? If I went to those peopleright now, do they have shorts on their podcasts? And if the answer is yes, then the problem is, no, they did buy.

And what I just said is not true. They did buy, but not from you. And that's the thing to figure out. On the other hand, if they didn't buy anything, if they just had a no buy, then it's not a question of how you're different from the competition.

It's an issue of you didn't find people where this is in their priority and you need to find in your marketing and sales people where this is in their priority list now. Not just people who could want it, but this isright now what they're activated on.

I mean, I guess.

If that's the case. So did they go with a competitor? If you check them, will you see shorts and transcripts and stuff or not?

The problem is not the competitor. The problem is offering a solution to something that they are already doing in the company. So they already have a person editing the videos manually. They already have someone writing the articles manually.

So what we are offering is something that is going to save time, not something that they suddenly are able to do.

Yeah, see, that's even harder because it is true that people are asked, especially in marketing, are asked to do more with less or at least do with less,right? Cutting costs in marketing is a common theme, especially now, but also always.

So I get it. Also though, you'll have a bunch of people who don't want you to do that because it's their job. So you'll have internal back pressure. That's really hard. So here on the one hand, you have something that saves money, which is not that interesting of a not that interesting of a proposal.

And you just named people who will push back on this and say it's not very good, whether it is or not. So that's headwinds going against you. And I can't imagine, again, that this is a top priority of whoever is the decision maker and all the things that their purview is.

It's hard to believe that this is a very important thing for them.

Yeah, yeah, yeah.

So if I was following through all that, it's just not that valuable, just not that important, just not thaturgent.

I

actually I am not the person to say this, but I actually think this is a product and a capabilities problem. To your point, Jason, about hyperframes and Claude kind of doing this, I think that if this was if you could have this for free and you wouldn't have to do anything, this would magically be taken care of.

For the agency customers, I think all of them would say yes because they should be doing this for their clients,right? They're going to edit the podcast and that's probably still manual, but then all the other stuff kind of downstream, the transcripts and the show notes and the titles and the publishing and the shorts and all that kind of stuff, they should be doing that.

I think they are not doing that with a solution like Podsqueeze because it's not that good. And that's not a slam on you guys, but I don't think it solves the entire problem because they're still going to have to go through it.

They're still going to have to edit it. They're still going to have to upload it to Instagram. They're still going to have to do all this kind of stuff. So I think it doesn't solve a painful enough problem in a complete enough way to justify the pain of switching from not doing this at all or a human kind of driven solution.

I mean, that's like we have an agency kind of arm at Castos. We don't use a solution like this because it's not good enough to take a significant amount of work off our team. And for me, as a user, I don't use this or Opus or anything like that because it's just not amazing.

And that's not a knock on you guys. I just think that we're trying to do this thing with AI that is not always amazing. We've all seen the results of this stuff.

Right, so you're saying if the humans were completely out of the loop, you would save time. But instead, it makes a reasonable draft that a human still spends a non-trivial amount of time on. And so while it saves a little time, it's just now we're just it's such a sliver at this point.

It's just not worth the effort of implementing a whole new tool and dealing with stuff and blah, blah, blah. It's just like the overhead isn't worth it.

Yep, that's my experience.

Wouldn't that mean though that the ones that are actually paying us would also not use the product?

I think they're are for what good enough is is different than other people.

Yeah, in fact, looking at your homepage, I got the feeling that some of your customers have AI voice podcasts. They don't even record it themselves. Is that true?

No, most of them they have their own podcast that they record, yeah.

Okay, I think I saw that in a testimonial or something. Anyway, but a person who does that doesn't care about the show notes. As long as the show notes are okay, it's fine. They already don't care.

I didn't get the question. So the person that makes an episode with AI doesn't care?

Yeah, if I'm already using an AI voice to do my podcast, I probably don't care that the show notes are AI generated. They're good enough. I already am just making a podcast that's just kind of okay at that point.

I wouldn't agree with that. I think there's a lot of big channels that are fully AI and they make it a business out of it. So I think they would care about it, I would say.

But not enough to actually make a podcast themselves?

I mean, I guess we could speculate about that, but at the end, what we want to figure out is how can we reproduce what we did in Portugal in other countries? If we.

Yeah, I think that's a good question. So

I think what we haven't put our finger on, so maybe you guys can tell us what the answer is. Craig has said, for a lot of people at least, it saves some time, but not enough time, or it does some good, but not enough.

So I guess some people will think that Craig does,right, and some won't. We've also talked about how it might help, but it's just not critical for them. And we've also wondered how it's different from other there's a lot of other tools that do this.

So we've also wondered how it's different from other tools. I didn't even say better, just different.

What will happen with Podsqueeze that doesn't happen with something else that some people might prefer? What we know is that people in Portugal will like that it's a Portuguese company. So to answer the question, how do we replicate this outside?

We obviously have to take that advantage off the table for other countries. So okay, so we take that away. And now we're left with, okay, so

for a large media company that wants to spend thousands of dollars a month on various AI-related things to support their work, whether or not they take it as is or whether they edit it afterwards, either way, I don't care.

Anyway, they have dozens of podcasts, let's just say, and they agree. This saves us time. We like it, and it's worth thousands of dollars. Let's say they agree. Done. What Craig said, they're like, "No, no, no, it's great.

It saves us time." Okay. Now, what is special about Podsqueeze or different to where if I were going to spend 1, 2, 3 thousand dollars a month, whatever, for these things, I would need to pick Podsqueeze over a competitor because why?

And the answer can't be we're Portuguese because we know that's one of the reasons in Portugal. And maybe it's not. I don't know. But let's take it off table anyway. Let's just pretend it is and ask, why would they buy Podsqueeze over you name it?

So you're asking us,right?

Yes, because I've just constructed the perfect customer for you. They have the problem. They know they have the problem. They have a budget of 3 grand a month to solve the problem. They understand it's going to be AI generated, and they may need to edit it afterwards.

They understand that already. They go to your homepage, they're like, "Yep, these are the features. These are basically the features I need, more or less." I'm stipulating all that is true. Now, why would they buy Podsqueeze? Now, given that, they're going to buy something.

I'm stipulating it. They're going to buy something. Why would they buy Podsqueeze over some competitor?

I don't see if that's theright question.

Well, what's the answer to the question? Why would they buy because that's what's going to happen?

Well, in these enterprise plans, I guess timing and the way you follow up, the way you present the solution, making sure that the.

No, no, no. I'm not asking how do you sell it. I'm asking if the customer's already going to buy something like Podsqueeze. They're either going to buy Podsqueeze or a competitor to Podsqueeze. We're just saying that. I'm not asking how you will sell it.

Let's just assume you are perfect salespeople. Whatever the answer is, you will sell it perfectly. Perfect process. Take that off the table. Why should they, in fact, genuinely choose Podsqueeze over a competitor?

I can tell. So for instance, if we see Cast Magic as a competitor, they don't do shorts. At least as far as I know, they don't do any video shorts, for instance. If we take Riverside, Riverside, they do remote recording, but they are not as flexible as our product is to generate the show notes.

It's more made for recording. So each competitor will have a different we have a different edge on each one of them. But what João is trying to say, and this is something we have been realizing a bit in our bootstrapping journey, is that the distribution sometimes is more important than the product.

Riverside is not a competitor. You're just making up competitors so that it's a good answer. Riverside is not a competitor.

Why do you think it's not a competitor?

They record stuff. They give you a transcript, which is good because you can also edit the stuff in place, which I imagine some people do and some don't,right? Some people use Riverside to do it and some don't. But they give you a transcript to begin with.

They give you shorts, but obviously, it's nonsense,right?

But it's a competitor. I mean, they do also show notes, though.

No. Anyone who's serious about shorts is not going to use Riverside for that. No, there are hundreds of competitors for making shorts, and you didn't name them. What's a good competitor who makes shorts pretty well?

Opus Clip is one that comes a lot.

Okay, Opus Clip is a competitor. Why should they pick Podsqueeze over Opus Clip?

In that case, I think it's because we have a more complete solution that does both. So we also do the show notes. We do the text part, which is quite important for them.

Okay, we are getting here somewhere. Are you as good or better are you as good at Opus Clip as they are at making clips?

Let me just ask, why is that question relevant? Because.

Well, are you or not?

In some use cases, I would say yes. In other.

Okay, which use cases?

Well, if you need control over each word, we allow people to edit the clips in a very efficient way.

Okay, and they don't?

Yes.

I'm not. I think the fair answer to this is that if we are only focusing on shorts, we are probably not better.

Yeah, I would say so.

So the feedback I get, and I think it's easier to tell about the feedback than rather what I think,right, because I'm biased. But the feedback I get is that sometimes Opus doesn't identify theright clips. But again, they also say the same for us.

Yeah, yeah, yeah.

It does give you some more control, Opus, in certain things. So yeah, it's not that everyone says Opus is much better than Podsqueeze, but they also don't say the opposite for shorts specifically.

Okay, so it's maybe kind of a tie?

I would say so, yeah.

But does the market if I poll 10 people in the market, would they say it's a tie?

For podcasters, I think so, yeah.

For short clips, they would say it's a tie?

For short clips that includes other types of clips, like YouTube and stuff like that, maybe they would go more for Opus.

Okay. So you can see what I'm prodding at here. I'm trying to figure out why would someone buy Podsqueeze over competitors? And you have an interesting thing that could be an advantage or a disadvantage, or I guess I would say and a disadvantage, which is that you do many things.

So the problem is if I zoom into one thing, I probably can find a better vendor because that vendor does nothing but think about that. So they will probably do a better job.

Yeah, true.

The underlying thing might be better, the UI for whatever it is after it might be better,right? But to your point, it's hard to find a vendor that does all of it.

Yeah.

Like here's Castos. You guys both do hosting, but Castos doesn't do some of that. I don't know, whatever it is,right? So the all-in-one is something that you have that many others don't.

Yes.

Okay. So

also, I don't know that you have to beat everyone else. Again, when there's hundreds of products that do stuff like transcription, I'm not sure you have to beat everybody. I'm not sure that's what's going on with transcriptions or even shorts.

I think you have to be not worse.

If I use Podsqueeze and the transcriptions are just garbage, which I know they're not, but let's suppose they were just garbage, then if you're trying to sell it by saying it's all-in-one, but the transcripts are garbage,

that's just if I care about my podcast, that's just not acceptable. On the other hand, if your transcripts are fine and it's like, "Oh, this other tool, it's almost the same, but they do this one other thing," you can compete with that,right?

The fact that you do many things, that's fine. You just can't lose outright to some of these other ones because then I'm really giving up something by going with Podsqueeze,right? So that's why I was harping on this with Opus.

So

there's no way you're as good at newsletters and blogs as some kind of very specific blogging AI thing. But does it have to be the perfect, amazing thing? No, probably not. For a lot of your customers, can you be good enough?

I would guess yes, probably. And the fact that it's all integrated and I don't have to so the good news of so the good thing about an all-in-one product is one vendor, one throat to choke, one tech support line, one budget line item.

Once I pay the thousands of dollars a month, I'm in. And I can stop thinking about this stuff. I'm not having to see demos of millions of things. And it all works together. You've ingested my podcast and bam, all this stuff comes out in a beautiful UI where the whole pipeline of my episode going to publish is all together.

And the transcription and the show notes and the socials, they're all connected. So I have this beautiful connected UI. Oh, this is so good. So that feels awesome. And now you can sell against things like Opus clips and other things by saying, "Oh, sure.

If you wanted to, you could literally buy nine different tools from nine different vendors, all of whom are charging you in weird ways and upping their price every year." And then you could figure out how to be the project manager to glue all this crap together and copy and paste stuff all over the place.

Yeah, you could do all that. But god dang it, why would you want to do that? With Podsqueeze, what's beautiful is it's all in one place. And so see what I mean? So I'm now because if I can build if the answer to my question, which is why should they pick Podsqueeze, if the answer is because it's all in one, which means all in one is actually not the answer.

All in one is a feature, is a fact,right? But if the answer is what I just said, it's so easy, the UI, there's a pipeline, it's my whole thing. And you say automate your podcast, but automate isn't what I'm saying.

And so maybe I'm wrong with my pitch, but you see what I'm getting at. Because you said automate, and Craig says it doesn't automate everything, actually. So this might be the wrong positioning, but okay. If this is how I do everything in my podcasting in one shot without having to wire up nine vendors and still have all kinds of problems with that integration and project management, that's pretty sweet.

I get that. Now, again, you can't be terrible at transcriptions or terrible at clips or terrible at making blog posts. Fine, fine. Because then it's like, "Yeah, I like the UI, but god dang, guys, I'm not actually getting all these things, really, because it's so bad."

You see what I mean? You still would need to say, "Ah, there's this minimum bar." What you can't do and you shouldn't do, and I don't think you are doing, is say, "We've got to beat every competitor at every piece."

You can't. You can't. And that can't be the strategy, and that can't be the promise to the customer. What you could do is say, "It has to be good enough that they're like, that's good enough that the fact that it's all in one is just winning the day for me."

Now, not every customer will agree that doing all in one wins the day. Not all will agree, but some will, and that's where you're going to win. But if someone said, "Look, the only thing listen, I already get transcripts out of Riverside, and then I edit it.

I already do the editing myself. I don't need you for that." And the show notes, I just pick a Google Doc and other people type in what they want, which is PS, what we're going to do. And so I don't need AI for that.

But the shorts, that's the only thing I need. Okay, well, then you know what? Maybe occasionally they'll still get Podsqueeze, maybe. But it's okay if they don't because that's not how you win. If they only wanted the one thing, sure, there's probably some competitor out there on the one thing.

If they already wired everything together, okay, I guess, sure. But to me, again, okay, fine. Now, that's all assuming the strategy of the all-in-one pitch is theright one, which it may not be. I'm just giving you an example.

But this is why I was asking these questions, why it matters, because what I'm trying to get at is what is it that you have that you can win on? And it's probably not head-to-head on one of these bullet points with a vendor that's super good at it.

It's possible. If you tell me I'm wrong, we're actually best in the world at newsletters and blogs. I'm like, "Great." I would say, "Great, then say that." Right now, I see on your website 10 bullet points of all of equal weight, but if you're telling me one of them is the best in the world, well, freaking say it then.

Then sell it. So that could be. That could be. No issue. No problem. These are all examples of how could this work? And notice we're not saying Portugal. This is why I'm getting at this. Why will people buy this that aren't in Portugal?

That's what we're getting at.

Yeah, makes a lot of sense.

Yeah, but again, there's a lot to unpack there. I think in these past two years, we have worked on improving the product. And so we haven't yet seen

a relationship between improving the product and converting better, more clients.

Well, that is because you're adding features and you're not doing anything I just said.

No, no, no. I'm not talking about adding features. I'm talking about improving what we already add according to the feedback from the clients.

Yeah, yeah, yeah. But again, that's not what we're talking about. You'reright. You've proven that just improving the product the way that paying customers have asked for isn't working for growth. It's good work. I'm sure it's good work. That's not the question.

But what you've proven is that incrementally improving the product in whatever direction, quality or features, whatever, for people that already value the product, we've already proven that does not create new growth. So what we're trying to do here is say, "Wait a minute, what should the product be and positioned and sold how that would be substantial new growth?"

Because just adding a feature or making the quality a little higher is not the answer to that question. So we're focused on this new question now, and we're isolating our brains to just this question of because this all came because Tiago said, "Well, how do we get more sales like these media sales or big agency sales outside of Portugal?"

That was the trigger for this latest part of the conversation. So for just that part of the conversation alone,right, the answer is like, "Okay, it's about positioning in sales for this product that you have now."

It's not adding another feature because you already have big media companies happy with these features. So adding a feature, so should you incrementally improve it? Yes, of course, of course. But that's not the answer to how to get someone from Germany to buy it or Central America, as you've already proven.

Yeah. I think it makes a lot of sense.

So even just this phrase, "Automate your podcast production and promotion," is that what the big agencies are doing? Are they automating their podcast and promotion? Is that what they would say they're doing? If I ask them, "What are you doing with the software?"

would they say, "Oh, it automates our production and it automates our promotion"?

Yeah.

We also have that difficulty trying to figure out exactly what Podsqueeze did for these enterprise companies.

Well, I'm not asking what it did for them. I'm asking how they would describe why they love it and what they do with it.

Yeah, yeah. They mostly mention I mean, we have different enterprise clients that use mostly the clips, and we have. But mostly of them, I think the biggest edge for them is the transcripts and the way they can interact with the transcript and create content out of it.

Okay. So if they're interacting with the transcript, then that's not automation.

So I'm not saying you have to go change everything now. Again, what I'm getting at is this is why what we're talking about now is different from incrementally improving the product. We're talking about positioning and selling the product now, the product that you already have, that people already love, people who will pay you five times more and then maybe another two times more, let's imagine.

Those people already love this, and there's a reason for that. And if we can put our finger on it, and we won't do it all here, you might need to talk to them more or review the text and hear what are the words, the actual words they use,right, which won't be the same words that you use always.

Sometimes it will,right? And what do they say? Because that thing, what they say about it, that's what it is that you want to position for. And so another interesting question will be, do they love that it's all in one, or do they not care about that?

I don't know the answer. But if that is something they value, then that might be a again, it is something you have, so is that something to put forward? But if they say, "I never really thought of it that way.

I just like the transcripts. I never really thought of it as all in one. In fact, I don't use most of the stuff. So no, I don't use it as a quote-unquote all-in-one. I use transcripts." See, if they say stuff like that, then leading with all-in-one won't be a very good idea because that's not what the successful customers who do love you, that's not what they that isn't what they value, even though it's true.

So now, of course, it's going to be hard because like you said, not everyone's the same. So you're not going to get the identical answer from everyone. But you see, this is what I would try to go do to get the positioning of and answering what are those customers saying?

Because that is the message to take to Central America, to Brazil, to Mexico, or to anywhere else,right? Is it like there's tools that do transcripts, and there's tools that do editing, and there's tools that do shorts. But the problem is

the transcripts don't understand that what you need to do next is editing. And the editors don't start with a good transcript. The only way to get a fantastic edited good transcript is if you do both. Now, it's possible that what I just said is a pitch that your customers would say, "Yes, exactly.

Exactly. Yeah, that's it." It's possible. Maybe probably not because I don't know what I'm talking about. But they could say that, in which case, it's kind of an all-in-one argument,right, because it's about multiple pieces that are integrated. And then maybe it is that argument, but in that particular way, just under that hypothesis.

Craig, do you have any thoughts on that?

Yeah. So you said something that I think is for this answer to the question Tiago had of how do we sell more of this to agencies? You kind of said the answer, which is you do customer interviews. And now there's jobs to be done and all this kind of stuff.

There's a bunch of frameworks and books on it. April Dunford has written books.

I might even have a framework and a book on it.

You probably have.

You probably do. I actually have AI skill at skills.asmartbear.com. But I do. I have AI skills specifically for finding good questions to ask your customers. So you can check that out.

And I think the most important thing here, and this is why I think early on it's so hard for new companies to get traction, is because you don't have what you said, Jason, which is the same people saying the same stuff over and over about what they want.

And there's three things. You need the same people, so you need agencies saying the same thing, "Oh, it's this transcript," or, "It's the clips," or, "It's the whatever," and you need it happening a lot. You need all of those things to be true a lot to be able to have the conviction for yourself of saying all the other five bullet points on this page and the words are not important, but this is the only thing that's important.

And actually, I think

that is hard when you have two different types of customers you're selling to, which is the case for you guys, or it should be. Or it is currently. Maybe it shouldn't be. But if you only sold to agencies, that answer would be this.

And if you only sold to individual podcasters, the answer would be this. And then you try to smush those two together, and this page looks like a mess. I'm not saying this page looks like a messright now, but I'm saying if you did that, then the messaging and the positioning would be inconsistent for each of them, which is the risk.

And so if you guys do that and you have the conviction to only sell to agencies, then only put the agency stuff on this page.

Yeah. Yeah.

Probably the answer to how to grow this company.

I wouldn't say the page is a mess, but when I looked at the page in my notes ahead of this, I was specifically saying, "This is for so many different people. I don't understand what's going on here." If you told me it's all in one, I would understand better.

But you didn't even say that. And so you're the host of the podcast, but you also distribute and help get people to view the podcast, but you also edit the podcast and make content, adjunct content for the podcast.

Now, if you paint it so I'm so confused. And also, it says manage multiple podcasts. Oh my God, what? Another thing? Multiple podcasts? And it's because you're speaking to your different customers all at once, and it is a mess.

I don't know what to do. And then I go look at your pricing page. I still don't really know what to do. There's Pro, but then there's Agency, which is about the same price as Pro. I don't even know why it's different.

Is it different?

So it is confusing because you are mixing your personas on the homepage. Now, either you pick one and focus, like Craig is saying, which I think is a good idea, or you acknowledge you have that and you paint that story off the homepage.

Podsqueeze is used from everyone, from individual creators just getting started, all the way to some of the biggest podcasts on Earth, blah, blah, blah, or agencies that run hundreds of podcasts because everyone needs the same great stuff, blah, blah, blah.

Now, if you said that, now when it's like now you can even say a whole page just for individuals and getting started people, a whole page just for agencies, a whole page, and you could send me there, and now it's making sense to me, and now I can see that on your pricing page.

Now that can make sense to me now. But you didn't say that,right? It's just automate everything, which is not even reallyright.

But what are you saying, Jason, is that we shouldn't do that? What we should do, it seems, is, okay, we've tried the B2C, the individual creators. We have done everything we could. We realize that our customers that will stay with us for a long time are big agencies.

Let's do the same we did for the small customers to the big agencies. Let's figure out why they are using it. Let's figure out how we sell to them, and let's put that in the main page. Let's put it in the pricing and somehow ignore, in a way, that other tier,right?

Well, that could be. That would be pivoting the company. You could choose to do that. Another choice you could have is to say, "Listen, we're a bootstrap company. We can't afford to just not run the business we have and have the profit we have."

That's not an option.

And so what we want to do is, yes, we would like to change our mix of revenue so that more and more comes from agencies, and maybe eventually we full pivot away from the previous company. But we can't afford to just turn off the spigot now.

And so what we're going to do is we are going to have dedicated pages for the individual or whatever you want to call that and for the agency so that when we are in control of where we send the traffic, we'll send them to theright place.

So when we run ads and SEO for individuals that are getting started, we will send them to the getting started page. And when we talk to agencies and run those ads, have that SEO, or make those sales calls, we're going to send them to the agency page.

And our homepage is going to indeed say, "We cover everything from here to there because our stuff is so universally useful, and here's links to this and that,"right? And so if someone goes to our homepage anyway, they'll get directed.

And that's what we're going to do so that we don't just tank the business we have. I think that's a very reasonable thing to do. And then again, of course, over time, you can always elect how much are you emphasizing one or another.

Maybe the homepage does switch to agencies, but you still have the other web pages for the other stuff, so you can still funnel people over there. And maybe eventually you decide you never want the other business anymore, and you really do want to shut it off.

All under your control. So yes, the more focus is better, complete focus is best, but there's also the from a strategic perspective, but there's the practical consideration of you're here now, you use this for income, and you need to fund all this other stuff.

Yeah. Of course.

So we have to consider that. So I think that's very reasonable to do.

Hey, Jason, I have a question for you on behalf of these guys because I'm sure it's something they're wondering. You mentioned in the intro they turned out an offer for 500 grand last year. I know that podcasting is a challenging industry.

I think AI is challenging for SaaS in general. I think these guys are in a kind ofultra-hard spot because of the ongoing value kind of that people get from the business.

That's fair.

We've talked about pivoting the business to agencies. It would probably be easier for them to sell to. But I think at an even higher level is if you look at the opportunity cost that they have, is this the best place for them to spend their time?

I mean, nobody knows.

Yeah, it's exactly a question.

Because you could say AI will eat all SaaS, and in particular, you're using AI for this, which means other people will, whether it's competitors or the agencies themselves. So your days are numbered and you should stop and you should try to get out of it and sell before that's too obvious.

You could say that. I think that's a very reasonable thing to say. Very reasonable case to be made for that.

The reason I'm hesitating is, is there a SaaS business out there where you couldn't make that case? No, you could always make the pessimistic case that AI is going to eat your ass. Okay, so everyone should sell? No.

In fact, lots of SaaS companies are quite profitable and doing fine, including the big public SaaS companies whose valuations are tanking like crazy. I understand that. But whose revenue and profit are often up. So valuations, okay, yeah, I get the valuations, but actually the businesses are healthy.

A lot of them are super healthy, actually. So if we back apply that here to a bootstrapped situation where you may not care about your valuation, quote-unquote, that much, and you do care about whether you can grow it and make profit, it could be that getting this to double the profit—notice I didn't say revenue—double the profit with this idea might be a whole lot easier than selling it and then trying to find another business that's profitable.

That also sounds really risky. So again, I feel like both of those are very excellent paths forward. They're very logical. They obviously come with different risks and trade-offs, and they're both smart. It's smart to take money off the table and go do the next thing.

And it's smart to say, "This is working.

You have an avenue for much higher profit that you could potentially unlock that'sright there at your fingertips." And you know why the other rest of the business is not good. And it's actually not because of AI. It's because the customers themselves go out of business, which actually would be true if you were doing this business 10 years ago.

So you know that, though. So it'd be logical to say, "I don't feel like going after these agencies and making a different kind of business model. I don't want to do that." So I want out. That's logical. But so is to say, "Yeah, of course, I understand why that part of the business isn't good.

Let's go do this other thing, the agency thing."

Because if you also think about it, since we started, everyone said, "But why don't we use GPT?" And as you can see, we are neither growing, but we are also not

falling. So yeah, I always thought that maybe, and eventually, it could be that AI will just replace us fully. But I guess another question would be, who would buy such business? Who would buy a business that is not growing?

Yeah. I mean, this is a different question. It's an interesting one. There's lots of answers because you're small enough. What's really hard is these companies at 20 million, 100 million, 200 million revenue because then the answer of who buys it is a small list.

Especially the big race is a small list.

And good luck. But lots of people want to buy a small company who they believe they could take you from 16K to, let's say, 80 or 100K in MRR over a couple of years because they look at the business and say, "Oh my God, this is a marketing and sales play.

You guys don't know what you're doing." I'm exaggerating now because I'm telling you what the other person would think. "You guys don't know what you're doing with marketing and sales." I mean, first of all, you should be charging three times as much to those media companies, and I know how to go get 100 more of those in the US.

So I'm just going to go do that. The end. Get out of my way. I'll buy your business, and I'm just going to go do it. And of course, there's people that think that. They may beright or wrong, but it's a very logical thing.

Any other insights?

An investor won't buy it because there's nothing to invest in. It's a sideways business. There's no big payoff. Now, there could be with agencies. That's what we were just saying. But you haven't proved it yet. So an investor needs that proof.

So as an investor, I don't want that because you haven't proved that it can be different. But if I'm buying the whole company as an entrepreneur and I'm the one who's going to do it, awesome. Investors don't buy and then run it.

They want to buy and then see that it grows.

Yeah, of course.

And de-risk that idea. Okay, this is not a de-risk growth story. Again, I'm not putting it down. I'm just saying it's not an investable thing. So what? It's just not one of the choices. But there's all kinds of entrepreneurs out there who don't want to build a business from scratch, can't build a business from scratch, and see a lot of opportunity in the podcast world.

I mean, I don't think podcasts are going away. So I believe in the podcast market as a whole market. I do believe it's changed a lot. And of course, Craig can talk, and so can you guys, about what does that mean.

I don't imagine we're going to stop seeing new podcasts appear, but I also don't imagine we're going to start seeing them convert to real podcasts any higher either. I imagine it's going to be like that. And some older ones will stop as they do.

Maybe they run their course or whatever. Nothing's forever. I mean, Seinfeld stopped making Seinfeld episodes. I mean, kind of, okay, sure,right?

And AI will have lots of roles to play. And I think that so let me give you an opinion that's not that informed because I'm not the podcast expert here. I do not believe that people want to listen to AI-generated content.

Period. So I think people that do real content—I hate even the word content. I don't make content. I try to make good shows and good articles because I think content sounds throwaway. That's what most people do. But anyway, I think people want to see good stuff by humans.

And I think we want to automate all of the busy work bullshit that doesn't add any human value to it. Like this, like all the stuff you have. The shorts, I don't—sure, shorts can be whatever because they don't have any value other than like an ad.

So I agree. I want to use AI for shorts too. Show notes. Yes, of course. It's just busy work to pick out all the stuff and find the links. Please do that for me. That has no value for a human being doing that.

So of course, I want to automate that. Transcription. Of course, I don't want to type all the words while I'm listening. Are you crazy? So the more accurate, the better. And just as you say, I want to also use that as part of the editing for all the reasons you say already.

And actually, I love the fact that with you, I can start with a short clip that AI made to pick out a good area, but then I can edit it so that it's as good as I think it can be.

I love that. You're getting rid of busy work and allowing me to still make the thing. I like that.

Audio enhancement. Sure. Great. Again, making a blog. Okay, I understand why that's useful sometimes. For me personally, that's not useful because my blog is so sacred to me and what that is. So I wouldn't do that. So what?

I just said I wanted seven out of eight things. That's great. What the hell? That's really good. I don't have to do eight out of eight.

We can get you a free trial so that you can experience now with this episode.

So I think you could be very well positioned to not be disrupted by AI if the attitude is, "We don't want AI doing the episodes. We want AI to remove busy work that no one cares whether a human did it or not."

I do care if a human being wrote or did the podcast. If this podcast we're doingright now, where AI is, of course, no one would or should look at it. The only reason they're doing it is because we're real humans.

But I'm sure no one listening would want us to even want us to try to transcribe it or maybe translate the close captions to another language. It's like, "Of course, of course, please do that." Right? And so

I think that's the perfect place for entertainment or infotainment, or in this case, it's kind of maybe it's infotainment. I don't even know what you call it. I don't care. It's what it is. It's your get to listen in on real founders.

All four of us are real founders trying to solve this stuff, bringing everything we know to bear. Do you want to listen to that or not? That's what it is. And the instant it's AI or content or we read something, it's like, "What?

That's not why I'm here." I'm not trying to sell a consulting contract on the other side of this or some nonsense. It's just we're just trying to do it. I think that's compelling, and AI can't take that away.

I mean,right now, everybody I know, if they notice that AI made the YouTube video, then they hide the channel. Nobody wants that shit. So I think if you're at this intersection of, "Of course, AI to automate the busy work and make some of the stuff like marketing better," hell yeah.

Okay, well, why is AI making that go away? I don't understand. You are using AI to make the busy work away. You're doing it. So why would ChatGPT make it go away? You have all this stuff around it.

The stuff I said about, "No, you're going to own the whole pipeline of getting it out there and the project management." ChatGPT doesn't do that. Now you could say, "Oh, but you can make skills and project management and use Obsidian or freaking Notion or whatever."

Yeah, I know, but almost no one builds all that. Only people like us do. That's 0.001% of the population's doing that crap.

Did people stop using Basecamp because now you can do that in Obsidian and AI? No. UI matters.

I'll just kind of give my perspective on the podcasting industry. I agree. I think in a lot of ways, it's stronger than ever because of AI, because people need and want this human connection. I think that that's both for consumers of it and for brands wanting to create content that is really genuine.

Pretty tough to fake this kind of conversation. So I think as a medium, it has a lot of tailwinds. It has a lot of support. I think the question for you guys, to me, of just back to you had this offer for the businesses, you turn it down because you believe there's a path to grow.

And maybe that's the prosumer route. Maybe that's the agency route. I don't really know. To me, I think selling to agencies seems like an easier thing. Agencies get sold to a lot because everybody says the same thing. "Wow, I can go sell to agencies.

They have a bunch of people that are their clients that they can pass through to, and they're easy to identify and stuff." So selling to agencies maybe isn't as easy as Jason and I make it out to seem, but selling 8 bucks a month is also hard.

So I think that's kind of the I don't know the answer, but I would guess since you turned out an offer, the answer is you believe there's a path to grow. I think podcasting is about as AI-resistant of a market as there is in certain applications of the market.

So I think you're relatively safe there, especially the more you get to critical tooling and infrastructure for serious creators or agencies.

Yeah, I mean, for the thing that

we are making around 200, close to 200K RR,right? So

of course, that half a million is a lot, but it's something that we could also since the business seems to be so stable and it can change, but it's something that we can, "Okay, we wait two years and a half or something, and we get that."

So maybe we value that more. And of course, we always think that we can improve. And you did give us some great ways on how to look at or what to look at in the next months. Yeah, so it's been really I really appreciate your time and your insights because I think that this is also how we grow, bootstrappers together, exchanging ideas.

And this has been really, really helpful. And I really appreciate both of you being here and accepting well, I kind of invited myself to the podcast, but I do appreciate the fact that you accepted that, Jason.

That was awesome. And I would say there's one other way you could think about or one other way to at least one other way an acquisition can happen, which is that an agency buys you for themselves. So let's suppose I'm an agency and I need to do everything you're doing, but I want to own all that code and do all that stuff so I can just do whatever I want with it forever.

Now, this is a bigger agency, to be clear, not like a three-person agency, but a bigger agency. How would they build this in-house? If they've already decided strategically, "We need to bring this in-house." Let's say they've made that decision.

How will they bring it in-house? Well, one is they could build it themselves. One is they could buy something that already exists and go from there.

The vibe code.

Building it themselves takes longer and it still takes millions of dollars because one team at a big company costs multiple millions of dollars because it's not just their salaries and taxes, and if they have equipment, maybe they have office space, they won't get it allright the first time.

There's opportunity cost lost in the amount of time it'll take before they have something that works. And they don't have experience. They have to develop the experience in-house to build it at all, etc. You just said, "We added all kinds of features customers needed, and it took us two years."

Right. That's what it's going to take though. It's the new way of it. That's not good. So

that's going to cost them a lot of time and millions of dollars. So shouldn't they just give you a million dollars to stop doing it, to just bring Podsqueeze over there and forget your customers or wind them down or whatever?

Or maybe they want to keep them because now I don't know. Who knows? But even if all your customers had to just go away, it's so much cheaper to just give you guys a million dollars, half a million dollars each, or even a million dollars each to say, "Hey, stop that.

Bring all your stop that with your customers. Bring all your crap over here. And from now on, let's make what we want starting from here and startingright away." So we're going to roll this out on our 200 blogs that we manage now, and we're going to do whatever we want in the future because now we own it.

And you'd say, "Okay, so I'm just painting a picture." Whether you want to call that an acquihire or a real acquisition, I don't care. I don't really know how people set that bar, and I don't care. But that is another way to get to a valuation, which in terms of a financial multiple is unreasonable.

Paying a million dollars or two million dollars to this business is not reasonable. It's too high if you only looked at it financially. But I just gave you a scenario that's quite possible. They're not looking at it like that.

They're not computing it like that. So they're asking, "How do we get this in terms of time and money?" And oh my gosh, a million bucks is actually the and we get it today is a really good deal.

Right? And so they don't care what your finances are in that case. Right? So that's why I bring it up. It's a way to get an amount of money that's more than what it is sort of let's just for the sake of argument, say, objectively worth financially.

I know that's not really a concept, but okay. In the ballpark of what it should be worth financially, how would you get more money than that? Why would that happen? Actuallyright in your backyard, agencies.

Right. What do you think would be a price we could actually sell it to?

I just said, it depends on why they're buying it.

Well, if it's not that

low. What is low? What would it's like 2X?

I don't know. Likely the answer is you can't. The answer is there's no lowest price because sort of like my thing from before, if you gave me this business for free, but I had to run it, I'm not sure I want it.

If you guys leave, you gave it to me for free and you guys leave, I don't think I want that. It's too hard.

Why?

Because I have to hire people as good as you and pay them what you're making. And I've got to solve the problem we just talked about on this call. That's a lot. A lot of risk, a lot of people.

Man, I can't take on all that risk, and that's too difficult. I've got to enter a new market with a new team. I mean, that sounds really, really hard. Now, again, if I was an entrepreneur buying it, okay, then that's different.

But you have a sideways company. So even 1X revenue is pretty good.

That half a million, even that would be maybe possible, but pretty hard.

Because again, I'm going to need to hire somebody else. You guys take off. Well, okay, the new entrepreneur replaces one of you, but I got to hire somebody else. Again, there's stuff to be done that costs money and risk.

Right?

Even though, to be fair, the other scenario I gave, I think a million dollars is easy. I don't say easy. A million dollars is possible. Maybe even two. A million each is maybe possible in a strategic buy like I was talking about where we're not talking about finances.

Got it. So at the moment, we are not putting out, as you know, and you mentioned that, we are not putting our full-time. Podsqueeze almost runs itself.

So that's even worse.

Why?

That's even worse.

Why is it even worse? If I just told you that you don't need to hire two people.

Because you so don't believe in this company and what it can do that even you're not spending time on it. Even the founder doesn't believe in the future of this company.

Sure.

Okay. Got that point. So it's like a passive asset that is there.

It is not a passive asset.

Generating.

A passive asset is I bought stock on the public market and I'm holding it. That's a passive asset.

A passive asset is I wrote a book and I get tiny

royalty checks from the publisher every quarter. That's a passive asset. It wasn't passive to begin with. Okay, now it is. Right? Then it is. That's a passive asset. This is not a passive asset at all.

Okay. Okay.

You have to do a whole bunch of work just to keep the business where it is.

So what you're telling me is that no business like ours has or hasn't been sold for 2X. So you cannot sell a business like this unless it's for the other scenario where you told me.

What I'm saying is financially.

What people just can't get the software.

It's all bad news because it's not growing. Cancellation is super high. You've been unable to grow marketing or sales despite trying, which suggests that it's impossible. I don't think it's impossible, but if I'm just taking the outsider view,right?

Yeah, of course.

Right? It's been flat for two years despite you trying every kind of thing you could think of. Nothing works.

And then even you don't believe in it, so you went part-time. And if you're going to argue with me that that means it's a passive asset, then I would turn it back on you and say, "So is what you're telling me that if you went full-timeright now, you could double this business in a year?"

Is that what you're telling me? Okay. Well, then it's bad news that you're part-time. It's because you know there's because you think there's nothing that could possibly be done. It's not even worth your time working in this business.

See what I'm saying?

All of these were yeah, yeah. And we discussed all of this.

I'm not saying all this is true. I'm just saying as a buyer, this is why financially, I can't value this very much. Right? Financially. That's why. Because that's the story I see.

Right? And as an investor, especially, I'd be like, "What?" Now, as an entrepreneur, I can see it differently. "Oh, you guys don't even understand the opportunity. You don't know how. That's why you're not working on it. I'm going to go do it now.

I'm not going to overpay, but I could do this." That's a possibility.

But you just told me you wouldn't even get it for free.

That's me. But there's a different person out there like Craig. Now, maybe Craig doesn't get rid of Craig's like, "Dude, I already have the hosting locked. I don't have other things to upsell." He just said, "I don't have a lot of things.

I have features to upsell, but I could use more." So maybe Craig's like, "Okay, if I could upgrade all these if I could upsell these features, first of all, he could take your customers and try to sell them the hosting, and he could take his customers and try to upsell them your features.

And maybe he could get another million dollars of ARR in total out of all this." Okay. What can he afford to pay for that? Certainly half a million, not probably a whole million. I know it's ARR, but there's a lot of risk and timing in this.

That's why I'm saying that. Right? And it's not profit, it's revenue. So that might be a quick thought powers of 10 thought process of how that could work. Right? But then the best way is if it's not valued financially at all because I'm an agency, I'm thinking completely differently.

And as an agency, I'm thinking, "Oh, I already charge many millions a year for this kind of stuff. I want to have a special and highly optimized thing so that's a hyper-profitable thing that I can continue to get clients all day long with this awesome story of AI that I have that my consulting rivals do not have.

And if I'm going to build this in-house, it's going to cost me several million dollars and a year. Instead, it could cost me one or two million dollars, and I get it tomorrow done." See how they don't care what your financing is.

No, no. Makes sense. One last question is I know that you probably also need to go, but what about the brand? For Craig, actually, this is a good question for you. We don't offer only the business,right? We have a good ranking on Google.

We have tons of people. So inside the podcasting world, you could easily take this and pivot towards your business or start another business. So isn't this value as well if you're trying to sell, especially to another company in our industry?

I don't know categorically. I think you could say it's either neutral, a benefit, or a risk. I don't know. I think for you guys, as it relates to I think as it relates to us, it would be neutral.

If we bought Podsqueeze, we would just fold the product into our solution and sell it to our customers. Podsqueeze.com would just go away. I think the agency model

Jason mentioned, it would be

nothing,right? Because they would just use it internally. I think that the only place it would be added to is if you

were going to operate next to, on an ongoing basis, another brand to where they could share SEO and content and cross-selling and all this. But if it was like, "Hey, we're going to buy you and just fold you into our product," it's almost nothing.

So you just think all the 30, 40 thousand views we get every month, you just ignore it?

I mean, we would redirect all that into our site and bring your content over and stuff like that. But yeah, I don't.

Okay. But then there's value,right?

I don't know. Yeah. I mean, yes, there's some value, but to quantify that into a dollar amount, I think would be tough. That's definitely not the thing you're selling.

Interesting. Okay.

Everybody has a degree of that.

Again, you've kind of proven that traffic's not that valuable.

Well, I guess people bail. Yeah. I can understand.

Now, you could say.

For our business.

That's what I mean. So you could say, "Oh, but for another business, it would be valuable." And I would say, "Great. Name that business where this particular traffic is really valuable," and then maybe they would value it a lot.

But if we can't name it, and it's like, "No, it's just kind of the same," then I think what Craig said isright. Is it worth a dollar? Would Craig pay $1 in order to get all your content folded in?

Of course. Is he going to pay a million dollars just for the content to fold in it, just the SEO? No. Okay. So we've established it's valuable, but not that valuable for Craig. And again, if you could name someone else where they would call it very valuable, then you've answered your question.

But if not, then it's okay.

No, no. That's why I asked Craig as well. Because if it was the opposite, I would say, "Greg, I want those users. I want those podcasters because I'll put them in my funnel, and there's a conversion, and I'll definitely get something, some value out of it."

So that's why I posed this question, but it's definitely interesting to me.

And it would be some value. The problem is when you go down that whole thing of and the conversion rate and which of them stay after a year because their podcast didn't fail, and you end up in what is the actual value of it, you probably end up with a pretty small number.

And so then the question is, if you tried to LTV it, which I don't even like LTV, but suppose you just did a basic LTV on it,right? The LTV is probably not that good. And then the question is, what will you pay?

Let's say the total LTV for a year of this traffic is, well, shall we say, 100K of revenue?

How much we would make in LTV?

Yeah.

We have a competitor that they did a lot of these, and they made way more.

No. What would you make an LTV off of all what do you make an LTV off of all this SEO? Remember, most of them cancel.

How much revenue do you drive from inbound?

Yeah.

Yeah, yeah. I think that the lifetime value of each client is around $200. So

that would mean.

No, not when you count everyone that comes to the site.

No, no, no. The ones that convert,right?

Yeah. Not with the 20% cancellation rate. No.

You are talking about the lifetime value,right?

Yeah. No. Because they're on the $9 plan and the 20% cancellation.

That's a $50 LTV for those people. And that's surely the majority of the people.

I mean, we do have those metrics here on Stripe,right?

Well, that's the metrics. At $10 I know it's euro. At€10 a month and a 20% cancellation, it's $50 LTV. If it's 10% cancellation, then it's $100 LTV. So it's something like $100.

Yeah, but our starter,

I think

most of our clients subscribe to the Pro most of our revenue comes from the Pro plan, not the Starter plan.

Oh, is thatright? Okay. That's unusual. That's really cool.

So here it is.

So it's 150?

Euros. So it gets close to 100.€150? Yeah.

Okay.

Just what's the answer? What's the LTV total for a year of your inbound, of your SEO inbound, not your sales, but your SEO inbound?

I don't have that number on the top of my head. We have to see the I think from Google, we have a conversion of around 1%. So if we are bringing 40,000 people a month, that would be.

That's not the question. So the point is the company is flat at 200K a year,right?

Yeah.

I mean, in this segment, in the SEO segment, it's flat at 200K a year-ish or less?

Yeah.

Less,right?

A bit less. Yeah, that's it.

It's flat at 150K a year in this segment?

Yeah. Yeah. Under 50, under 60K dollars. Yeah.

Okay. So it's about 150 because that arrives and leaves every year,right?

So there's about 150K. Okay. So that's the answer. It's worth about 150K in revenue, not profit. In revenue, not profit. That's what your SEO is worth to you in this business currently, 150K,right? In revenue, not profit. So what would I pay for that?

Well, not 150K because the profit how long would it take the profit to pay that back? A long, long time. Less. Now, you could say, "Yeah, but you could do something better with that traffic." And I would say, "I know, but that's the acquirer is going to do that."

And they may not. That's a risk. So you see what I mean? So maybe they pay only 100 or 50, or maybe they pay half a million. Maybe. We don't know. But we've set sort of the ballpark of what is that traffic worth even to you in this business in revenue, which isn't profit,right?

So we can't put a number on it, but we can put a power of 10 on it. It's something like that.

Got it.

But really, it's in the eye of the buyer because the agency example, they value that zero, but they might give you a million dollars anyway,right? And so it's someone else the other way around. They're like, "Who knows?" Right?

Yeah.

Yeah. But I think what Craig is saying is Craig wouldn't this is Craig's target audience, and he's not valuing it very much. More than $1, but not a lot is the answer.

Yeah.

Guys, I unfortunately need to also get going.

Yeah. We definitely need to wrap up. It's gone long. I always wonder if we can do this in an hour and then it goes two hours, but I think. Have a lot of meat. So it's okay.

Guys, thanks again so much. You were so generous to do this and to expose all this. And you know this because you saw it yourself on other episodes, but it's so valuable for everyone else too, for you to be vulnerable and see that, "Oh my gosh, it helps other people see and ask themselves, 'How would I think about this for my business?'"

And very often, we were like, "Well, that part's like me. That part's like me." And so I think it's great. And whatever you decide to do, maybe in the future, once you're further along, whatever that path is, if there's a new challenge to solve, maybe we can come back again, whether it's like, "Allright, we've talked to 20 agencies.

We've got a couple more on board, and how do we scale that?" Or maybe we decided to sell. How do we structure that? Who knows what you decide to do? But

maybe we can do it again.

Definitely. I appreciate your time again. And there's a lot of things now to discuss, a lot of things to think about. And I love this. And keep doing this with other founders because it's very helpful. I'll definitely listen.

I would just say you guys got a lot of constructive, hopefully critical feedback and stuff, but you should be very proud of building the business that you have. It's not something to take lightly, to be making 150 grand a year and owning your time and building a real business that has enterprise value.

So you should be really proud. But business is tough, especially these days. So don't undersell what you've done so far.

Yeah, yeah. Definitely. I mean, we are very proud.

Yeah. It's awesome.

We know that we could be making more, and we want that, but coming from working a 9:00 to 5:00 to having this freedom, it's incredible. So we're definitely very happy with this.

It's great stuff.

Yeah. I would echo that. And I would say

my bet is Podsqueeze has a lot more life in it, whether you want to call that value or what you want to but I mean revenue and profit is what I mean, whatever that ends up resulting in. I think you got stuck on a shitty market.

You tried everything you could inside of a shitty market, and guess what? It didn't work, proving it's a shitty market. Okay. Then you found the hint that there's a not-shitty market, and legitimately, you're like, "Jeez, I don't know how to attack that not-shitty market."

And hopefully, we've gotten some progress here and anyways, a mindset for how to continue. And you might want to talk to more people who are great at building a new sales motion, and there's positioning on the website. There's all kinds of things to do,right?

And having seen like, "Jeez, there's a better market out there, but our initial attempts didn't work. It's a new motion we don't understand." So rather than doubling down and figuring that out and getting other people to help or whatever, I'm just going to go part-time and do other crap.

And so the business suffered because rather than saying, "Oh, this is a new thing we have to figure out and do, let's go figure out and do it," and spend all of our time figuring out and doing it until it's done, instead, you took your eye off the ball, "Let me go do something else because I don't know."

You could do that, but then you shouldn't expect it to change,right? I think this has a lot more legs. Now, who knows how much? I'm not saying it's going to be a $100 million a year business, but who cares,right?

That wasn't the goal. Who cares? But I'm saying, "Oh my gosh, of course, there's more legs in this. Of course, there's a lot more to go do." But it's different from the market you've stayed in that's crappy. It's a different market with different motions that you're going to need to do.

And you could decide, "I don't want to. So instead, I'm going to sell," or, "Instead, I'm just going to continue doing it part-time and make it as part-time as possible so you can go do other things." Those are all totally legitimate things.

I'm not judging. I'm just saying, "If you want to, I think this has a lot of legs, but you have to decide to go do the thing where the market is good."