Transcript: Non Tech Saas Founder & Future of Content Sites – Jason Paul Hendricks – DS528

Doug: Hey, what’s going on? Welcome to the Doug show. I’m Doug Cunnington and today I’m live at location at the tasty weasel. This is the Oscar blues brewery. I’m sitting outside with my buddy Jason Paul Hendricks. And we’re just having some beers. How’s it going today?

Jason Paul Hendricks: Going good.

Doug: You’re in town and you were like, Hey, I’m going to be around.

I’m going to come by Longmont. So we should meet up for beers. And we’ve been chatting for a couple of hours. We decided to record an episode and we got a couple of topics we’re going to cover today. We’re going to talk about why you’re here in Colorado, juggling various projects, which can be very challenging.

Saas as a non. Tech, uh, founder, right? You’re, you’re doing a couple of things in content sites in general, probably a few other things, maybe some tangents. So did I miss anything? Is there anything else we’re covering?

Jason Paul Hendricks: That’s a lot of ground. I think that’s good.

Doug: So Jason, for the people that don’t know you, who the hell are you?

What do you do?

Jason Paul Hendricks: A question I ask myself sometimes too. The day job, if there is one is in the finance industry specifically FinTech. So I do consulting work for financial technology companies. These are companies that are mostly selling B2B software. And I specifically am based in Asia.

I currently reside in Hong Kong. I’m trying to change that, but So I help folks that are usually U. S. or maybe Europe based to sell into Asia. But the reason we know each other is because I’ve also dabbled in websites. I’ve had, I’ve had multiple sites and also done some side projects in terms of SaaS in the marketing space, digital marketing space.

I’ve been online for a very, very long time. I also recently launched a podcast with your help. So that’s how we know each other.

Doug: Awesome. And you were one of my top three students in the whole program. So congratulations on that. It’s a, there were three in the program to be clear. There’s your shows. Great.

We’ll link up to it. So people can check it out.

Jason Paul Hendricks: Appreciate that.

Doug: Well, thanks for joining me today. Thanks for getting in touch. Now, why are you in Colorado?

Jason Paul Hendricks: I’m, so I’m in the U. S. For some business meetings. I was in New York City. That’s where I landed. Also some personal catch up. Cool. My brother lives in Denver, so I’m, I’m in Colorado for a few days.

Excellent weather. I’m loving it. Crisp, clean air. Yeah. Something we don’t always have in Hong Kong. And then after this, I’m heading to Southern California to see my son.

Doug: Very cool. Well, I’m glad you got in touch with me. Let me know you were in town. I was excited to come out here. And, uh, yeah. So if people were around the, the Longmont or Denver area, there’s a lot of breweries, as many people know in Longmont, just a few miles from where I live, there’s a ton of great ones.

Jason Paul Hendricks: It’s my first time in Longmont. And really nice town come to Longmont, but not too many people don’t want to spoil it.

Doug: So let’s talk about content websites. Cause I think like you first you and I first connected through content websites, like in general. So do you still have some sites out there?

Like what’s going on with that?

Jason Paul Hendricks: I do. So I guess the first ones I can talk about are I do consulting for a bootstrap founders. So I have a consultancy focused on that. So small Saas startups, small founders you know, for a very long time, you can see all the gray hair I’ve helped with operations and also business development, you know, with larger companies, but I think a lot of those same ideas and practices translate into smaller companies as well.

I’ve also been a founder and done startups myself. Nothing with some huge payday, but again, lessons learned from the, from the failures, you know, not just sometimes more so than the, than the successes. So, so a bunch of folks on the, mostly on the digital marketing Saas startup space that I’ve been helping out.

So I got a site over there. I’ve got a site associated with the podcast. I help with operations on a food blog. On a travel blog. And each of those, the, the sort of face of those sites are subject matter experts, not myself, but I, but I help sort of behind the scenes on those. And I also have a test or yeah, sort of a, I guess it’s a test site.

This is a site that I started last year for Spencer Hawes, AI site challenge. Okay. And. I joined that competition largely to experiment and try out some things that I wouldn’t really want to necessarily try on the other sites.

Doug: Okay.

Can you talk about some of the stuff, some of the things that you tried?

Jason Paul Hendricks: Yeah, well, I mean, it’s heavily, that content is heavy AI, you know, usage. So, for any folks that don’t know, the that, that challenge started in September. I think it was, yeah, I think late September. Maybe it officially started beginning of October. And it concluded at the end of March of this year. And, uh, six months.

And you had to build a new site from scratch. And you had to use AI in some way, shape, or form. He wasn’t very prescriptive about exactly how you would do it. I sort of went, I went heavy, you know? Sure. Why not? Yeah, it’s a test. Yeah, it’s exactly, whatever. So, but I had, I still had a, I had a nice process.

And, and that was part of what I wanted to test. So. We did, if you want to know, right, so I did I used AI to help with outlines, and then I had an AI content writer that did the first draft. I did not do anything with the draft. I had one, one team in the process would, would take it and do very basic stuff like gathering external link candidates for the article.

I gave, I gave a process for all of these things. And they’d gather together, uh, basically. The sort of extra stuff you, like images and that sort of thing. Gathered it all together and then it went to an editor who would go through and do like proper human editing on it. Tweak the title if necessary, fix the headers, you know, break up wordy paragraphs.

The sort of things you need to do with an AI written piece of content. And so that was the process for that. And so a big part of the personal experiment of that site was to, validate whether that SOP works. I don’t know. I can, I can tell you a little bit about what happened to the site towards the end and you decide if it worked.

But but one of the other things that I did with that site was, so it was in a self improvement niche, specifically motivation and people can just go and see it. I mean, I’ve disclosed it’s a motivation pay. com which is It’s an odd URL. It’s an odd domain, which I actually had one a couple of years earlier in a random drawing.

So I never would have bought motivation pay. com, but I, I had it in my, my collection and I thought if I, if I don’t use it for this, I’m not going to use it ever. So it was a motivation related site. So this other thing I as we got into December, I wanted to do a press release campaign. And but.

To do a press release, you need to be announcing something. And so, I decided I wanted to try and do a like a motivation, an AI motivation mentor app, right? But my first impression was to do a GPT. So this is a, it was very popular at that, at that moment. OpenAI had made this marketplace available and you could build a GPT and so, I did a little research and there were some other motivation mentor type apps there.

But, but I thought like, why the fuck am I going to build something on their site? And you know, and then do a press release for it and then send links to open AI when I want to build links to my site. And so that sort of set off a cascade of other ideas about what I can do. Long story short, though, I ended up doing a press release campaign, got some extra links and Ended up 15th out of, out of about a hundred.

So I started at like, I started at like 98 in the rankings on the very first a month and I ended up at 15, I think 13 was my highest position. So not bad, but like I didn’t win the competition. Is that ranked on based on effort? Yeah, yeah. It’s, I would have, I would have ranked much lower if it was trying to run effort but no, it was the last month.

traffic, but it was specifically Google traffic. So it wasn’t all traffic.

Doug: Okay.

Jason Paul Hendricks: So, so, and that was his experiment, which was, it was a nice contest and nice experiment was, can you build AI based content and and will Google specifically reward you with traffic for that?

Doug: Okay. And we’ll come back to that.

We’re going to have maybe, I don’t know if it’ll be a debate on content sites and search and whatever. We’ll come back around to that. You mentioned that project, you mentioned a podcast, you have a full time job, you have other things. So how do you actually manage and prioritize your projects?

Jason Paul Hendricks: It’s a non scientific method I use.

So, yeah, I, it’s it’s, it’s difficult to actually, I I try

I should have a better answer for this question, but yeah as best I can. I, I, the consulting thing, you know, it’s lumpy business, right? So sometimes I’ll have more work to do than other times. And so one of my, one of those clients, for instance, they, they were doing a tour through Asia and they, they needed more meetings.

And so there was sort of a hyper intense period where I was trying to. you know, set some things up for that client. And so I kind of have to drop other things, right? And then at other times I have more bandwidth and I have more control over my schedule. And, uh, and then at that point, I feel like I have to prioritize the, you know, the short, medium and long term.

So as I told you offline and by the way compliments to you. You don’t know, but Doug waited till the third round to turn on the, the, the, the recorder.

Doug: Yeah, I’m not doing much talking. I asked like three questions. You gave me the questions.

Jason Paul Hendricks: There must be a strategy to that. But yeah, so, so as we were discussing earlier though, I I’m, I’m trying to sort of put a bunch of bets down, set up, set up sort of potential opportunities or projects that could pan out.

And you know, so the sometimes I’m invest, I feel like I’m investing too much time into one thing that doesn’t have an immediate payoff, but yeah, I, when I do have the time, I try and balance it across these different projects, some of which may be more time sensitive and and maybe have a short term benefit.

Others. maybe more time intensive, right? Require more time investment, but there’s a longer term potential payoff. So

Doug: is there one, maybe a project that you haven’t even mentioned where you thought it was time sensitive and it was going to work out and then it turned out that it did. And you thought, Oh, I really, I, I’m going to really focus on this thing for whatever weekend or month.

And you’re like, Oh, this. It’s so time sensitive that I really need to work on it. And then it turned out to be a flash in the pan or not actually nothing at all.

Jason Paul Hendricks: Some of the specific tactics that I, that I tried for that website for that test website, I thought would pay off better than they did. I think for that site, I, I kept my expectations low.

So I, I can’t, I can’t say I was really surprised or disappointed. I was like, keep, keep expectations moderate. I was co founder in a, in a startup many years back and that, that, that was not a week or a month. That was a sort of a two year process. And, and that I think my, my experience then probably informs how I handle a lot of things.

That was an extremely you know, that was that was long and an intense investment of time and energy and ultimately didn’t pay off. And, and I, I attribute most of the problem there to that being a startup that was consortium based. So it was dependent on investors and it was in, it was, it was dependent on other people, you know, sort of giving their blessing or buy in like industry players.

And I think that Everything I’ve done since then has been informed by that being, that being, you know, the SAAS I’m on now or the content sites or whatever, I want to do things that I have more direct control over and things that have sort of already been validated. Like, I don’t want to, like, I don’t want to try and create something brand new.

I’d rather sort of take inspiration from what I know already works and maybe do a little spin on it or something so I have a higher confidence. So, so I guess the short answer to your question is I try to avoid these situations where I put too much investment into something and have too high an expectation on it.

Doug: Yeah, I know there were so many various projects or usually they were just like one specific website and I was like, ah, really? I need to work on this now because I feel like this is the one that’s really gonna take off. None of them did, by the way. None of them did. But it felt like so urgent, like I really needed to do it.

And maybe I needed to do that just to understand that, like you said, the expectations maybe should be more moderate. Longer term projects work better for me anyway, where it’s just like consistency over a long period of time versus like, I’m not gonna do anything super amazing in a short amount of time.

Hardly anyone is, you know?

Jason Paul Hendricks: You know, you, I remember a long time ago, you mentioning your short experiment with agency work. Like working with clients. Yeah. And I don’t, I don’t know, was that, that was a few months maybe, but yeah. Six months max.

Doug: Yeah, probably six months. Yeah.

Jason Paul Hendricks: That seemed like it would require a lot of attention and energy and you were like, fuck this.

Doug: Right. It was horrible.

Jason Paul Hendricks: Thank you.

Doug: Yeah. Well the thing, I mean in, it’s a great way to get started. And at the time like I had just gotten laid off and I needed revenue coming in and it was, you know, One of the six areas that I was putting focus into. But yeah, at the end of the day I didn’t want to work with clients and I probably sort of knew that up front, but it took, um, six months of like working with actual clients and I was like, yeah, no, not for me, but it’s a great way to get started.

And then some people like technically one could hire account managers to work with a client to deal with the painful part. But then you, yeah, but then you have another problem where you’re like managing the full team and basically

Jason Paul Hendricks: narrow margins and all that. You know, you know what’s interesting though about it is I have a, uh, an article I wrote long ago, but it was, it was kind of, I’ve changed titles on it a few times, but it’s basically like lessons from the financial world, but for.

marketers or for business owners. And I think, I think the, the example here though is cut your losses and let your, and let your winners run it. Right. So yeah, if you do do one of these things and you realize it’s not going to pan out, it’s okay to, to, to take the L just cut it and move on

Doug: as quickly as possible.

Exactly. Is this some cost and just go? Yeah, yeah. So with the the AI site challenge, like you started doing that, you finished 15th, you got that sweet participation trophy. Yeah. Any other takeaways from that?

Jason Paul Hendricks: Try things. I mean, because I mean, talking about competitions, the, you always learn. So I set out not to, not to win.

I mean, the winning prize was 2, 500. It wasn’t like gonna, there wasn’t life changing money or even bragging right. But I knew I would, it would force me to, you’d have this sort of accountability factor. Cause, cause he was, he had a community set up around it. It was like Slack or Discord or something.

And made some connections through that. And could see what other people were doing. Like, the winner ended up being a non English language food blog from A smaller European country.

Doug: Wow.

Jason Paul Hendricks: That, that managed to just get critical mass in that community.

Doug: Wow.

Jason Paul Hendricks: And, and so there are all kinds of interesting takeaways from the actual winners and the ranking, you know, the folks higher up or whatever.

And even the losers, like people were very vocal about like, I, I can’t keep up, whatever. Some people have personal issues or whatever. One guy like started with like 50 sites. And Spencer was like, sure, as many sites as you want. One guy, he’s doing programmatic. Uh huh. That didn’t work out at all, right?

Didn’t, it’s, everything was at the bottom, you know, because you just can’t, you can’t invest the necessary time. Even if you’re, you can turn on the machines, but there’s still human involvement necessary. But, um, but one, you know, contest, another software development contest in this case, that I had participated in many, many years ago, Kind of also yielded similar outcomes.

Like in that case we won, but it was sort of the, the lessons learned from the process and the, the connections we’ve made along the way that really mattered. So I would, the best lesson I learned from it is keep participating in things, try stuff, you know, challenge yourself.

Doug: So you Saas projects you’re working on.

Can you tell us about those? And you’re a non technical, like, non software background person, right?

Jason Paul Hendricks: Correct.

Doug: So yeah, what are the projects? And we’ll dive into, like, the challenges of working on that. As a really non coder.

Jason Paul Hendricks: Yep, yep. So the first one that you know of is SerpSonar. It’s a Chrome browser extension.

So it’s meant to derive and Do analysis on the data from the Google SERP. And also from the ranking pages. So basically it’s a browser plug in, you search for a keyword, and it scrapes a ton of information from the top 100 results, from the actual pages, but also from the Google SERP itself. Generates reports, does these derived stats, other stuff.

It’s, it’s probably too much to be honest. There’s so much data in there. So I’m still working on how to, Best present all that and whatever. I could talk at length about it, but that’s been a pet project. Honestly, it, it, the first one or two problems that I had that compelled me to start that project, which is over two years ago specifically was around the KGR and so in a nutshell the all in title, Google’s all in title.

It. pretty janky these days. It doesn’t generate very clean results. So I wanted to basically make a plugin that looked at the top 100 results for a keyword and then did an all in title count manually based on what was actually presented. And that’s sort of snowballed into a lot more features, right?

It’s free plugins. So I encourage folks to go check it out, surf sonar. And, uh, that’s, that’s been a good, Experiment and project for me to, you know, sort of figure out how, as a, a guy with an idea, how to manage a software team and do all that sort of thing. So I can talk about the second one, but I don’t know if you have, let me ask questions about that one.

Doug: Let’s see. So I remember you contacted me pretty early on and it, it’s the only, uh, Fully licensed KGR usage. Some of the, if anyone knows, uh, tools that are using the keyword golden ratio, let me know. They’re not supposed to.

Jason Paul Hendricks: So I asked, I asked Doug for his blessings and I, he, he wasn’t, he wasn’t quick with his response.

I, I had to, you know, really explain it, go into some detail and

Doug: I’m often a slow on email but

Jason Paul Hendricks: I thought you were being thoughtful.

Doug: Yeah. Yeah. People can take it as that. Yeah, so, I was going to say, I remember even in the early version, and I know you took at least a little of my feedback but yeah, it’s like, so much information where it can be overwhelming to a beginner, like I could parsed through much of it, but at the same time, I was like, Ah, like, part of the KGR is this, the simplicity.

Jason Paul Hendricks: Yeah, that’s right.

Doug: And if there’s too much data, it’s overwhelming and some people just like, seize up. They don’t make a decision.

Jason Paul Hendricks: That’s right.

Doug: So anyway, cool project. We’ll link up to it so people can check out totally free plugin that helps the KGR work. Yep. A little bit. What’s the other project?

Jason Paul Hendricks: So the other one is a newer one. It’s this year only. Okay. And it came out of actually that that site competition. So a little bit of background there. It’s a self improvement niche. I think as I mentioned and I, I hadn’t realized that when I started the site, I guess in October, but January is like high season for self improvement and specifically motivation related.

Right. I mean, I, you never think of that as a seasonal, but it really is. Losing weight, whatever, self improvement, anything like that. So in December I was thinking about the press release campaign and I thought I would create some sort of destination feature that I could do a press release about.

And at the time the, the hot topic was open AI’s GPTs. So you could sort of create a GPT on the open AI site. The only people that could use it, though, of course, were people that were paying the 20 a month, right? Now, I think they’ve changed that since then. But, you know, I don’t know, I thought about it for a day or something, and I’m like, why do I want to build something on their site and then do a press release about it?

What, am I going to send links to OpenAI? They don’t need help, right? So, I had the idea of building an AI app on my own site. And so I went on Upwork, I found, you know, I have my process for, for sort of filtering and combing through Upwork profiles, but I found a software developer, some guys based in India, and started working with them.

And it was like, I gave them the spec at the very end of December, and by January 10th it was live. Like 10 days.

Doug: Oh wow.

Jason Paul Hendricks: To build and deliver.

Doug: And are you, um, so you’re not a tech person, but do you have, Skills and like business and technical requirements. So you like actually wrote up good requirements for them.

Jason Paul Hendricks: Yes. Although, I mean, we could really geek out on this in ways that I think you would understand. So, yes. So in my, my, my career in the finance industry, like I’ve, I’ve had stints as a product manager and but in the group side was always part of it was a business facing function. Like we were more talking to customers and then You have to translate what you think they want into, that’s right.

And put it into a spec.

Doug: But you had to approve them so you knew that actually.

Jason Paul Hendricks: Right, right, right. And also know how to, you know, put on the kid gloves and deal with developers and all of that stuff. So I had general ideas about how to, you know, manage these projects. But I don’t have my PMP though. But, uh, But yeah, in this case though, it’s interesting.

The guys that I use for the Chrome plugin, like we use JIRA, you know, we, we, we we basically use a lot of the standard tools of the trade and the guys for the other process, like they’re using a ticketing system, but I was like, so you want to give me access to the project and then I can do tickets directly into your site.

Like we don’t usually do that. And I was like, okay. I mean, Should I use a, just make a Google Doc or something? And so I’ve had to sort of come up with a separate process for these guys. And I’ve, I’ve, it’s all in a Google Doc. Like I’m trying to still put it together, give like, I put numbers next to each of the main features.

And I’m, I didn’t do it at first, but I’ve started to number even subtasks, you know, exceptions and things. Like I’m trying to come up with my own sort of, you know, Ticketing system, even though it’s all on Google Docs. Um, that’s a whole separate thing. But, you know, it’s okay, it’s worked out. These guys, though, they, they got the idea.

They had done some work with OpenAI’s API before. They’d done work with WordPress backend, but they’d never built plugins specifically. And the thing is, I didn’t know they were gonna deliver a plugin. I didn’t ask them for a plugin. I, I asked them, I said, I need an app on my site. And then they delivered it.

And then I looked in my plugin list and I saw that part of how they did it was, and this is like silly me. I, I didn’t, I didn’t go look in the WordPress marketplace first. So I didn’t, I don’t know why I didn’t do that. Like I’ve, I broadly had looked at AI, but I, I didn’t, I didn’t really scour through, but when I saw that they had done it this way, I was like, Holy shit.

Like maybe, and I went and looked and. There’s a couple of like sort of AI toolkits that you can do AI chat bots and, and a lot of them will allow you to do content writing in your WordPress backend. But who wants to write articles in the WordPress backend? Nobody does that, right? And so nobody was addressing this specific need, which is building a, an app or a form based app for your website, for your website visitors.

that utilizes open AI or one of these foundation model APIs. Nobody, nobody offered a plugin for that. So that’s where the idea came from. And I said, okay, I went back to the team after and I said, you know, would you be up to, for a bigger project, we’re going to build this as a proper WordPress plugin. And they said yes.

And so that’s where we’re at.

Doug: Can you talk about, or can you share how much it costs to get that developed?

Jason Paul Hendricks: Yeah, so for, for, for reference, the Serpsonar, I’ve been, uh, I can’t even tell you. It’s like the, the, the hourly rate is thirty something dollars an hour for, for that, those developers. It’s a pair of guys that, that I have.

And total for the life of that product, which has been over two years, I probably, I’m around six grand or seven grand total. Okay. For AI app on site, which is the name. I didn’t come up with a really clever branded name. It’s AI app on site, AI app on site. Don’t go to the website yet. It’s not ready, but it’s not launched yet, but although I guess now I have to launch it before you.

Doug: Yeah, unfortunately. Yeah.

Jason Paul Hendricks: Okay. But, but that one, I probably I’m probably around five grand total for it so far. Okay. Interesting. My hourly rate is lower.

Doug: Okay, but there’s just a lot more.

Jason Paul Hendricks: But there’s a lot more, that’s correct. Yeah. Yeah, that’s right.

Doug: Okay. What’s the overall vision you see for, for that the AI on site?

Jason Paul Hendricks: Yeah. The AI app on site is, uh, I think it, it serves two general purposes. So, my original use case that I stumbled across was basically as a link magnet. So yes, I was launching a, uh, you know, an AI assistant on this website and I was doing a press release about it, but a business that wanted to really do something clever and interesting.

And I think, I think people generally recognize these days that, that with enough prompt engineering, you can get some very interesting responses and consistency out of the models these days. And you can build all that into the back end of this thing. So, so one is link magnets, right? Just creating destination pages on your site instead of just the usual about page and the whatever the brochure page is for your business.

Doug: So, so just to break it down for folks.

Jason Paul Hendricks: Sure.

Doug: So you mean so, someone has a website and they want to build a, an AI, uh, tool, something like that, to attract the links because it’s something interesting that’s just normal. Maybe they, maybe they did research and they wrote some skyscraper article.

Jason Paul Hendricks: Right.

Doug: Who cares about that?

Jason Paul Hendricks: Correct.

Doug: Now they have a tool and they actually can like do a press release on it. People are like, Oh, this is a fantastic new AI tool for

Jason Paul Hendricks: whatever that specific business sub niche is, you know, now you’ve got an AI interactive AI app on your site.

Doug: Got it.

Jason Paul Hendricks: The second though, I think what probably will over time be the bigger use case, which I hadn’t thought about it before, but as I started speaking to folks about it, I realized is that it’s like a contact form on steroids.

Most people are used to going to a site and at most you’re lucky if you get like the name and the email address from someone, right? People don’t want to give more information. And even if it’s a I don’t know, like a more specific, it could be, it could be an IRL business, like a local business. It could be any kind of software business, whatever.

But, but getting people to fill in more detailed information about them as a prospect is difficult, right? Generally you, you get them to get in touch with you and maybe you have like a sales development person or a salesperson reaches out to them. Hopefully they take the call, blah, blah, blah. This is this interactive app that’s going to give sort of instant gratification.

And so in the form, you can get people to give more information because some of that information is going to be incorporated into the prompt that goes and gives them back this snazzy AI powered report that they’re going to see in real time. And of course you request their email address as well so they can send the report to your email index and And, and that information, of course, then gets sent to the site owner.

So I think this conversion optimization factor is is going to be the bigger selling point for this WordPress plugin.

Doug: Got it. Interesting. Would so let’s say you could sort of pick the outcome and I’ll, I’ll give you two choices. You can make up another one. So one is you run with this. Say for like two years and like you try to grow it and like you’re getting some traction and there’s a whatever say Say 5, 000 users or something, which is pretty good.

Jason Paul Hendricks: Sure. Yeah, sure.

Doug: Would you prefer to like keep growing it or Have a company acquire it because I think

Jason Paul Hendricks: That’s a good question.

Doug: Interesting thing because I’ve seen some people Honestly, put together some like shoddy bullshit. And, um, they get acquired now for a huge amount, but maybe say tens of thousands of dollars and they’ve put in whatever, a couple of weekends, like I’ve, I’ve seen some pretty shitty tools get acquired and I’m like, like this was not that great, but potentially it was acquired because of the leads or the email list or some other thing.

And the user base, not the actual tool or the technology. So. Would you rather, you know, have a good user base and keep growing it or have a good user base and then like acquired by a company where you’re like, Oh, you know what, let’s say it’s not a typical acquisition where it’s like two, three, four X, but it’s like a 15 X or something.

I had a friend, he sold a, it was a real estate related software company and he got like 5 million for it. way more than what he should have gotten, but it was a hot market. Good timing. He worked his ass off on it. But like, what do you think? What’s the best outcome? What would you rather do?

Jason Paul Hendricks: I mean, what did you say?

Two years, three years.

Doug: I don’t know. 18 months.

Jason Paul Hendricks: So it’s interesting. Ask this right? Because the first site I mentioned to you, I said I do Consulting for bootstrap founders, right? So this is like separate from the finance stuff that I do, right? So they’re part of my reason for doing that is to is, is lead deal flow.

So I have a handful of investor groups or buyers, right? That, that, that I, I mean, I’m not the only one, lots of people look out for potential deals for them. And there’s a thing where, you know, if you introduce. Potential acquisitions, you can get a finder’s fit. So, so, so part of my motivation for that consulting business, not like I’m trying to extract money from these bootstrap, their bootstrap founders, they don’t have a lot of money, right?

So, so, but the point here is that there’s this very active marketplace, say, between a ARR and 5 million ARR, right? There’s a lot of businesses in there. There’s a lot of buyers and sellers. And I think that that’s, that’s kind of what you’re, referring to. So if I was in the shoes of one of those founders, what would I do?

You know, I think this, I think I’m, I really have to get this thing live before you publish this because I think, I think I’ve somehow stumbled onto something that seems really obvious to me, but there’s no sort of direct, there’s no product that’s directly serving this need, but it’s, there’s no moat either.

So I think that if I grew it really fast, And I, we’ve got like a long roadmap of all sorts of enhancements that we could do. And by the way one of the extra sort of income levers that I was thinking of for this thing is, not everybody that wants to use the plugin would be willing to or able to do all the prompt engineering.

Like, cause we’re, it’s a blank slate. You have to do your own prompt writing. So we could, we could like do a service add on to that thing. So there’s extra potential income there and it’s going to be a subscription thing. So yes, there’ll be recurring, but I don’t see this like, this is going to grow to a certain point if I’m lucky.

And maybe there’ll be some sort of consistent revenue over time. But I think the best outcome would be if someone wanted to buy it.

Doug: Yeah.

Jason Paul Hendricks: So the question is would I sell it or not for the right price I would sell it, you know. And two years is a good window. If I can’t get it to a point where it’s sellable.

For a number that’s at least a little surprising to me, then in two years, then I’m doing something wrong. Not so with surf sonar. I mean, that’s, it’s kind of a weird sort of, it hasn’t found its identity yet, but I feel like this thing, even though it’s like brand new, I think I know exactly where it needs to go.

Doug: Yeah. And it’s AI related, which makes people like it. So quick, quick idea for. SERP sonar, SERP sonar AI. Just a little rebranding then it’s a hot, hot thing.

Jason Paul Hendricks: Okay. So side note, you know, I think six months after chat GPT hit, I had actually already worked in AI feature into SERP sonar, so you can add your open AI key to SERP sonar, and there’s a separate report that will give you.

Title ideas and, and meta description ideas, which is table stakes at this point. But the third thing it’ll do is it’ll give you a, uh, keyword intent determination. So it’ll give you two suggestions, like a highest con confidence and a second highest confidence. And yeah, and by the way, everyone thinks they know how to do keyword intent determination themselves, but that’s because they think they see best in the keyword and they go, oh, it’s commercial.

But try and do intent determination for all the other keywords, right? It’s, it’s not so easy and actually, so, so our little, our little prompt does a good job of it. But I think your point is taken. If I added, if I added more AI features to it, it might help.

Doug: Yeah. Yeah. So, okay. Very, very interesting. And I, I mean, every, everyone would have a different answer.

Different opinions. Some people would be like, Oh, I would want to keep growing it. But yeah, working on something for two years. And it’s like, I mean, the thing is like, if it’s a good idea someone’s going to take it, some, someone with more resources, a bigger company is just going to be like, Oh, WordPress is going to be like, Oh yeah, you know what, we’re going to do that.

And then they’re just gonna have

Jason Paul Hendricks: Honestly, they could. Well, you know who I realized my biggest competitors were? Fuck, I gotta get this live before this goes. But, like, you know, what is it, like, Contact 7 or something? You know there’s some plugins that do the form plugins? Those guys! They’re gonna be all over this.

So I gotta go fast.

Doug: You should get some I don’t know if you can get patents on certain portions of it. That could be a little rough. Then you just have to like for that

Jason Paul Hendricks: one patent idea for surf sonar, but I haven’t thought about it for this one

Doug: And it can get expensive like just doing the trademark stuff is like a couple thousand bucks if you hire a lawyer Okay, so let’s let’s move on Unless you is there anything else with the Saas that you want to talk about?

Jason Paul Hendricks: No, but one one Thought about selling versus keeping so Your big site sale from a few, some years back out of three, three, four years back or something like that. You guys intended to sell into the growth. There was, if I recall correctly, there was something existential. Maybe it was the Amazon thing or something.

Doug: It was like, yeah.

Jason Paul Hendricks: Okay. So you took a hit before you got a soul, but you intended to sell it on near the high, right? Like into growth.

Doug: Yep. Yeah. Yeah. And it it,

Jason Paul Hendricks: You were like doing technical cleanup and stuff, so there was a delay and then this thing happened, right?

Doug: And yep, and just for context, so this was the project with Rob Atkinson.

Jason Paul Hendricks: Correct.

Doug: And he had a site, and I, he needed help in a certain area, so it was like, hey, I’ll come on, I’ll do that portion of it. Right. We’ll sell it within a month. six months, whatever our target was. And yep. So we, we did the stuff. It was growing and we listed it like while it was at a peak retail season.

We expected it to come down a little bit, but then Amazon changed their commission rates and it dropped even more. Yeah. This was 2017 and that that was pretty big drop in revenue, like, uh, 35%. But yeah, the point is, yeah, we were selling to grow.

Jason Paul Hendricks: Yeah. So that’s what I would do with this. And if I can add one more sort of analog, uh, a real estate, a property that I sold was, this was post global financial crisis, but it was in, it was in a Metro area.

It was in New York Metro area. So even It was, it was a few years after the, the initial drop. And so this is an area that recovered quite quickly. But there, the, the point of getting rid of it was, like, we were aware of other issues with the property. Like, there were other risks. And I think, I think this is probably going back to my, like, financial lessons for marketers.

Like, it same happens with sites, right? Content sites, everything. Like, Every month that goes by, you might be earning income, but there’s also risk, right? Of something unexpected happening. And so that’s why I was happy to get rid of that property. Probably not as much as I could have gotten for it, but I was happy.

And I think for this Saas product, if I can grow it fast and I can sell it for a good price, even though I’m giving up some future growth, I’ll be happy to sell it also.

Doug: Yeah. And I’ve, I’ve tried to state it. No one will take this advice until they’ve made the mistake. So I realized that, but it’ll make sense later.

You understand it. You’ve been burned in this way and you took advantage of it in that example, but like you should try to sell things when other people, your peers will be like, why are you selling it? Like it’s just growing, just keep growing it. And that never lasts forever. And you, you can give up a little bit on the top end, but you, you, you’re ahead of the curve.

And the thing is like every thing that I’ve sold was a little bit late by a few months. And if I just would have sold a little sooner, it would have been like six figures or, which is a lot in the long run. Um, and I’ve tried to I’ll tell ya when we stop recording, but I’ve tried to give the advice to other people and they were like, Yeah, like, everything seems fine.

Yet these external factors, they pop up every year. Somehow. And, you know, they were a little too hungry, a little too ambitious, a chip on their shoulder or whatever. And it’s just like, they could have walked away and then taken a decade off or whatever. But instead They’re like struggling through it. So, yeah, but no one will take that lesson because you got to,

Jason Paul Hendricks: well, I mean, even sometimes we, we, we experienced those lessons firsthand and we still don’t remember them next time.

Doug: Yeah. And then sometimes you miss it. Sometimes you’re like, Oh, like you get surprised or whatever, but yeah, you give it, if you get rid of it, when people are like, Telling you not to do that. It’s probably a reasonable idea and it gives the buyer the upside too

Jason Paul Hendricks: That’s right,

Doug: and they feel good about it

Jason Paul Hendricks: them future growth

Doug: and like they feel good about that They do business with you in the future.

So, right. All right. So as we we wrap it up, so we talked content sites opening up and I Haven’t started a new site that actually put time into in like four years It’s I’ve gotten a little bit more it. There’s other things that I enjoy more. The, uh, I don’t have the hunger anymore. You, you mentioned you had a couple of sites.

You started the AI stuff, like you’re continuing to build a new stuff. And you mentioned when we’re taking notes, you told me all the ideas. You’re my AI today. You just told me the outline. You mentioned that you’re favorable. You, you think content website. A future. So can you expand on that?

Jason Paul Hendricks: I think recency bias is a thing.

It always is, it always will be. It’s the way humans are wired. Everybody thinks that whatever diSaaster is right in front of us is the way it’s always going to be. I think that I think, I think the duration of the Google drought that we’ve been in. If I could call it a drought, a drought of traffic for independent sites.

How about the duration of that drought is, is unprecedented. It’s longer than it’s usually been. They’ve got core updates after core updates and, and, and the wheel, you know, we keep getting, you know, trampled and, but it doesn’t, it doesn’t last forever. And besides, I think that. The part that, the lesson I think that people will take away from all this is diversification.

Like, nothing, nothing lasts forever either. And that includes Google. So there will be, there are and there will be other sources of traffic. Now I think things like, you’ve said this, a bunch of other people have said this as, you know, people I call thought leaders. People that actually have thoughts and happen to have mics too.

A lot of people have mics, but not, not everyone with a mic, I think has like thoughts worth spending time with. But, but I think, uh, one of those ideas is to get to build a business and not a site. Right. And I think that’s, that’s always been true. I think it’s logical and you know, I’m friends with people that do programmatic and they just want to let it shit out like a site with a thousand pages and stuff like that.

I mean, okay, maybe that’s interesting and stuff. It doesn’t necessarily have a, I think it, I think it has a, I think it has a negative effect on the overall ecosystem, but it’s not like, it’s not like littering, you know what I mean? Which, which has an impact on the physical environment. I mean, it’s like whatever, it’s an experiment, but it’s a waste of time in my opinion.

Right. I think, because I, I think it’s always been the case that if you want to have a longterm sustainable business, including a content site based business, you need to. Put thoughtfulness into it yet. Need to have a brand. You need to put quality content on, on that site. And that you can use AI to come up with outlines and stuff like it’s a tool.

AI is a tool. And I think if you do those things and you know, niche selection and stuff, not like, I do respect to the the, the, the air purifier site guys and stuff like I’ve never been down with. That approach, right? Doing an affiliate site. I mean, exact match domains is fine, whatever, but, but I’ve never been down with building a site that’s just around one product or something and just doing reviews.

It worked for a while, but fine. Like I have nothing against anybody that does it, but I would never do that, right? I’ve always wanted to put, create a brand, create some identity, put people and faces. So even the AI site for the content. We put faces on the about page. I was one, I had an editor, Filipino based writer and editor, a woman there, and I got a third person there who is a certified therapist.

Cause it’s a self improvement niche. And I asked him like, you want extra links to your site? And I said, would you be willing to do this? And so he’s the third person on the about page and, you know, humanize it. And that’s the way I’ve done all the sites, right? Like I mentioned, the travel site. Right. Both of those have real human beings with, with actual qualifications or, or at least some history, some story behind that.

And, and so I think those things, it hasn’t gotten harder, you know, is Google going to be the single source that, that you can depend on as to build your business on. You never should have done that. You never should have done that. Like I, I share your set. I’m almost done. I’ll pause and you can ask questions.

You’ve, you’ve I know your, well, your, uh, view on social media, right? But you know, the fact is you, you create those, what do they call it? I think, uh, Matt Diggity or Kyle may call it like social fortress or something, you know, new business, create the handles, you know, have a presence there, at least put a few posts up to start or whatever.

Personally, I never would build a business on Instagram. Some people are making millions of dollars just selling through Instagram. Same with TikTok. I mean, fuck that platform. Like, I don’t even go near that platform. But, like, the point is, like, you know, be in all these different places. You know, at least have a presence.

Some of them are gonna, Pinterest might bring in more traffic than others. Great. Use it. I, I, I would never suggest people only depend on Google. I, I would have said that five years ago. But, So, are content sites dead? I mean, of course not. There has to be content. You’re, you’re, you’re, in order to sell things, you want to give people a place to come and learn about you, and learn about your product or your service or whatever.

You know, is it, if it’s just about tricking the algo into giving you traffic, then yeah, that’s gotten a lot harder, but that’s not something you should have based your business on in the first place. Pause.

Doug: I I do, I agree with most of what you said, and one of the key things is, you mentioned like, Google may not be around forever, and I, luckily I’ve recorded, uh, many thousands of hours of content, so there’s at least a handful of times where I’ve said, someday Google may not be there. All it would take is maybe Apple.

Not using Google as the default search engine, which the week that we’re recording this, or within the last week. That’s right. Google has declared a monopoly, right? That’s right. And one of the things is like them paying Apple and other companies to be the default search engine.

Jason Paul Hendricks: That seems like one of the main reasons for that determination.

Doug: That could drop their search

Jason Paul Hendricks: Dominance, yeah.

Doug: Yeah, and the, the whole market share by 30%, which would be,

Jason Paul Hendricks: That’s correct.

Doug: Very dramatic. So, you know, it just takes a change like that to completely, like, flip everything upside down. And the thing is, like, the Google search results are not as good. So, I told you about this podcast, Omnibus, with Ken Jennings, the Jeopardy winner, that, that guy, right?

He’s mentioned on a few episodes, he’s like, yeah, AI has killed these Google results. Like, what is this nonsense? And he said it on a few episodes, which is great. I haven’t, I haven’t like taken

Jason Paul Hendricks: that’s not a digital marketing.

Doug: No, it is a random like general population. Ken Jennings is not a tech guy. He’s just a dude.

Jason Paul Hendricks: That’s interesting.

Doug: Yeah. So he specifically called it out. And so like, People widely understand that like, Google results are worse. They have all this bad press, so I wouldn’t be surprised if like, things got, you know, shifted.

Jason Paul Hendricks: You know, you mentioned

Doug: Which would be great, because fuck Google, just to be clear.

Jason Paul Hendricks: I second that. So, so, it’s funny you mention that though, that, that alongside that case news, I heard on another podcast The Apple crawler seems to be showing up a lot more frequently and a lot more widely than it used to. So I think the early assessment is that they’re probably scraping for training content for their own AI, but maybe they’re also hedging that they’re finally going to launch an Apple search engine.

Doug: And they must have something.

Jason Paul Hendricks: Something already, that’s right, that’s right.

Doug: Yeah. That’d be very interesting. Yeah, so I don’t know, I know from my own personal interest, like I said, I have been less enthusiastic about building sites because it’s harder, it takes longer, I’ve done it for a few years, and there’s other things that are more interesting.

And I tend to get bored after about five years, I think, and then I kind of stick around.

Jason Paul Hendricks: You know, of anything.

Doug: And then I’ll keep kind of doing it while I start other things in the next three to five years. So when I look back for about twenty years, that’s held true every five years or so.

Jason Paul Hendricks: Okay, I have a question about that, but first I have to say, just as an additional anecdote to your last point, my brother, who I said I’m here to visit, right, he, he’s I mean, he’s in the finance space, but he’s, he’s as normie as it gets, right, when it comes to this stuff.

He Some time ago, somewhere in the pandemic, completely fired Chrome. He’s on Firefox without my influence. Cause Firefox is my browser of choice, right? I have to use Chrome because I have a Chrome plugin, but you know, and he also uses duck, duck, go, okay. And he did that a couple of years ago, like for his version of privacy reasons, you know, cause I don’t think he’s, he’s not overly paranoid about this stuff, but it’s interesting.

I want to ask you about your cycles, your five year cycles. So is the, cause, cause I’m wondering with your, with your five stuff and your, your mile high fi podcasts, all of your interest in, in the financial days, which we’ve talked about before, is your, is your book with Carl about laziness actually sort of a punctuation mark at the end of one of your five year cycles?

Doug: Oh yeah. Yeah. Yeah, I think so. So just to give people context, my, my podcast partner and myself are working on a book on laziness, which to be, we’re still working on it. It is a book on laziness. So it’s taken a long time to be clear. I finished, I finished my stuff last October. I probably need to rewrite most of it, but Carl’s still working on it.

He’s like three pages to go or something like that. But I think, yeah, potentially because working on my own business for several years was a lot of like extra hours, a lot of efforts. And as I got to a point where I didn’t need to work as hard anymore, I intentionally made sure that it wasn’t working as hard because it’s easy to, you know, in certain circles, People like, I just want to learn more and more and do more and more and grow more and more.

And I was like, well, I don’t want to do that. So I need to make sure I stay far away from that and don’t get pulled into that. Yeah. So, so yeah potentially a little bit of that. Yeah.

Jason Paul Hendricks: But you don’t, I mean, I noticed that you don’t your, this cycle thing is interesting. Now I got to look at my own life and see if I have some sort of.

Like the cicadas or locusts, seven year locusts or something. I have my own cycle.

Doug: Yeah. And it could be, you know, shorter or longer or whatever, but, but yeah, yeah. It’s like you get to learn something new, which is usually pretty exciting. And then you get a little bit better at it. And then at some point it becomes mundane unless you add some extra layer.

But a lot of this stuff, if you go too deep, like I was talking to my wife about pickleball, right. We’re chatting about pickleball. She’s very good. And the thing is like, once you, she’s good, but she’s not too good. Once you get too good, then you can’t play with that many people. Cause there’s not that many people that are that good.

And then your peers are fewer and it’s less fun and they take it too seriously. And basically I was like, Oh, that makes sense too. Cause at some point people take things too seriously. And I’m like, well, that’s not that interesting to me. Right. I don’t care enough.

Jason Paul Hendricks: Fortunately for your wife, and I think my wife was also much, much better than me at pickleball.

They’re still not nearly as good as the best pickleball players. Oh yeah. There’s plenty of headroom still to go. So,

Doug: yeah. And it’s like you just hop on the court with another player who’s a little bit better. And then you’re like, Oh, I’m not as good as I thought. Cause she played with like one of the pros locally here.

And she was like, Oh yeah, I’m not, I’m not that good. I thought I was pretty good. She was playing with like. Old ladies in her league or whatever.

Jason Paul Hendricks: So spin on it, doing the smash and all that.

Doug: Yeah. Yeah. So, okay. So I think, I think we, we covered all this stuff that we wanted to cover. Any other topics before we let people know where they could find you and your stuff?

And you can think for a second.

Jason Paul Hendricks: Knowing, knowing, yeah, I think I, we could talk about a lot of different things. Maybe we’ll save it for another episode.

Doug: All right. Perfect. So where can people find you?

Jason Paul Hendricks: They can check out jphendricks. com, which is, especially if you’re a founder, you want to start a project, if I can help in any way, you can check out the site and see there.

JP Hendricks on most of the socials and um, digital downshift, my podcast, please check out my podcast. I haven’t gotten the next episode out for a while. It’s been about a month and a half, but I declared at the very beginning with, yeah, it wasn’t against the advice of my, of my mentor and teacher, Doug.

I declared at the very beginning that I was not going to be consistent with my podcast episodes, but, but I, I, I didn’t say that I wasn’t going to release them. So a month and a half is probably too long. I apologize in advance, but yeah, digital downshift is the podcast. Please check it out.

Doug: And it, I think, uh, you’re going to be okay.

Cause we, we did talk about it. And the thing is like, once you get, once you get on a regular schedule, then it’s important to keep it up. But you declared ahead of time that it was going to be sporadic cause you’re busy. You’re busy, right? You got a lot of stuff going on. And a lot of people have that. So, but once you start publishing on a regular basis,

Jason Paul Hendricks: I better keep it up.

Doug: Yeah. Cause people want like, I like it. The last episode that’s out. By the time this comes out, the other half should be out.

Jason Paul Hendricks: You’re right, actually.

Doug: You put out a part one of a fantastic interview with Glenn Alsop.

Jason Paul Hendricks: Yes.

Doug: And I’m waiting. Every day I check my podcast player to see if the new episode’s out.

Part two.

Jason Paul Hendricks: Part two, yeah.

Doug: But by the time this comes out, it should come out.

Jason Paul Hendricks: Yes, chef.

Doug: Alright, this has been awesome. Thanks a lot. We’ll link up so people can find all the stuff. And, uh,

Jason Paul Hendricks: Thank you, Doug. Thank you, guys.