Ep 389: 300+ deals! Here’s What Most Buyers Never Find Out with Joe Burrill

Everyone wants to know how to buy a great business.

Almost nobody talks about how great businesses quietly become bad deals.

After more than 300 business transactions, Joe Burrill has seen it happen time and time again. Sellers mentally check out months before they list. Buyers obsess over valuations while missing the risks that actually matter. And now, with AI changing the way online businesses are built, bought, and grown, the gap between good buyers and great ones is only getting wider.

So what should you actually be looking for?

In this episode, Jaryd sits down with Joe to unpack the lessons he’s learned from brokering hundreds of online business sales. They explore why the best deals aren’t always the fastest-growing ones, how experienced buyers think about traffic, revenue diversification, and risk, and why a simple conversation between buyer and seller can be more valuable than another spreadsheet.

They also dive into how AI is reshaping acquisitions. Why content businesses aren’t dead. Why SEO still matters. And where new buyers are getting due diligence completely wrong by relying too heavily on AI instead of using it as a tool.

If you’re thinking about buying your first online business – or your next one – this episode will change the way you evaluate opportunities.

Because finding a business to buy isn’t the hard part.

Knowing which one is actually worth owning is.

🎧 Hit play and learn what 300+ deals have taught Joe that most buyers never find out until it’s too late.

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Episode Highlights

03:32 – How Joe Turned One Website Into a Career—and Eventually 300+ Business Deals 

08:31 – The #1 Mistake Sellers Make That Quietly Destroys Their Business Value Before an Exit 

12:02 – The $15K Deal That Used a $2K Holdback to Get Both Buyer and Seller to Say Yes

18:24 – The New Rules for Buying Content Websites in an AI-First World 

24:08 – Why AI Won’t Replace SEO—and the Costly Mistake Buyers Keep Making During Due Diligence

29:18 – The $172K Valuation Error AI Completely Missed—and Why Human Judgment Still Wins

37:15 – If You Had $20K–$100K Today, Here’s Exactly What Joe Would Look For in an Online Business

Key Takeaways

➥ The fastest way to kill your exit? Stop running the business before it’s sold. Buyers don’t buy potential—they buy momentum.

➥ Deals close on trust, not spreadsheets. Strong buyer-seller relationships solve problems that contracts can’t.

➥ One traffic source is a liability. Diversification is a premium. The more ways a business earns traffic and revenue, the more valuable it becomes.

➥ AI is a powerful assistant—not your deal advisor. It can speed up due diligence, but it can’t replace experience, judgment, or pattern recognition.

➥ Content websites aren’t dead. Generic content is. The winners are building brands, authority, and original insights that AI can’t replicate.

➥ Creative deal structures create better outcomes. Seller financing, holdbacks, and flexible terms often turn stalled negotiations into closed deals.

➥ Buy the business you’re best positioned to grow—not just the cheapest one you can afford. Your competitive advantage matters more than the asking price.

About the Guest:

Joe Burrill started buying and selling websites in 2012 with a $700 acquisition. He’s since closed over 300 transactions totalling more than $6.8M on Flippa, where he’s been named the platform’s most successful broker. As founder of Just Website Brokerage, Joe is the only Flippa broker to hold every badge the platform offers. He’s the rare operator who’s lived on both sides of the deal table many times over.

Connect with Joe Burrill

Transcription:

Most of the people who are coming to me wanting to sell their business have sort of checked out already. They're sort of like, I'm done with this business, and I have been maybe for even a year.

And I'm just I just don't want to have to deal with it anymore. So the biggest mistake is just letting it go. We see many, many times that one of the directives that we even give in, like the broker agreement before they even sign up, is to keep running the business as you have.

Please just keep running the business because the worst thing that you can do on a sale is if the business starts to come down while it's for sale. And we have to keep lowering the price, and it doesn't show a lot of confidence about the business. Even if it's a great business, the reason it's declining is that they're not spending time on it.

Buyers are still gonna see that as a trend that is going to continue after they take it over. That would be the number one mistake that I would see most of my clients doing. And I would advise, you know, if you're gonna list it for sale, just don't check out. Keep running it until you've got a buyer.

I'm Jaryd Krause. I'm the host of the Buying Online Businesses podcast. And today I'm speaking with Joe Burrell. He started buying and selling websites in 2012, a little bit before I did, and he bought his first business, which was a $700 acquisition. He has since closed over 300 transactions, totaling more than 6.8 million on Flippa, where he's been named the platform's most successful broker.

Now, as a founder of just Website Brokerage, Joe is the only flipper broker to hold every badge from the platform's offers, and he's the rare operator who's lived on both sides of the deal table on the acquire side and the sell side, mostly on the sell side now. And in this pod we talk about how Joe got started in online business and why.

We also talk about what type of online business you should be buying for, say $20,000 to $100,000 in today's market, what that would look like, and why it's not generally advised; why it should be more specific to you.

We also talk about deal structures in that price range of 200K and under. And are there seller notes, and how are deal structures, it mostly cash or not? We also talk about the number one thing that sellers do get wrong when trying to sell a business.

And we share it and mention the elephant in the room: AI traffic, Google search, the state of content sites, what it looks like now, why we're still bullish on content sites, why they're necessary, how to build them into the future or build a portfolio of businesses. We talk about SEO.

GEO branding. We just talk about why deals fall apart, and I share some AI due diligence risks as well. Now there's so much value in this podcast. Obviously you're listening to this because you want to buy a business, but before you do, do yourself a massive favor and dramatically decrease your risk of buying a lemon by getting my due diligence framework. That's what I use; it's what my clients use. And it's not only made people millions of dollars, but it's saved people millions of dollars. It's free.

And there's a link in the description. And lastly, I'd also love to give you some money. I do pay finders' fees for up to two grand or more for anyone who refers me to a deal that we actually go away and acquire. So if you know anyone with a business doing or yourself, doing 250k net per year or more, reach out. I'm interested. It might be exciting. If we acquire it, I would love to send you some money.

Now let's dive into the pod.

Joe, welcome to the pod. Hey Jared. It's great to be here, mate.

Yeah, absolutely. We've got an Aussie business acquirer seller on the pod. Now we chatted a couple of years ago. It's been a long time now since we chatted last, right? Yes. And you've done some really, really cool things. But I don't think I've asked you how you got started? Like, I know it was twenty twelve you bought your first website, but what drew you to this?

That's right.

So the origin story actually started with my older brother, who gifted me Cash Flow One, which is like a Robert Kiyosaki cash flow game, and it just taught me about investing. Through school in Australia especially, you don't learn about investing, you don't hear about, you know, any financial stuff pretty much.

And so that was my first arena into it. I had a full-time job as an office clerk, and I was always pretty good at like conserving my money. And I just had a bank of money. There wasn't much, but enough to sort of go, well, what do I do with this? And that led me into investing. I met Matt and Lesrad, who I'm sure you're aware of.

They're also pretty big in Australia. And I did their high-end mentoring course for a year. Ended up finishing top of the class. I got their big it was called the Dead Set Legends Cup back in the day. I got awarded that, and that sort of set me on my path. I bought and sold businesses both for myself and for some JV partners that I had partnered with who sort of helped me with the cash.

I was sort of more like the operator for a while. And then in around 2019 or so, I realized, well, before this, I realized my main skill set was when it came to selling. I was really good at selling, getting high multiples, and had a good strategy for doing that.

And I started getting reached out to by people, people reaching out to me to ask me, like, what can you sell one of my businesses for me? And I'm like, Well, never considered that, but okay, let's give it a go.

And just Website Brokerage was born, which is my company, and now that's all I do. I don't actually buy and sell businesses myself anymore; I help my clients do that.

Similar to me, I no longer buy I buy for myself; I buy for my clients. And you no longer sell for yourself; you sell for your clients. And congrats, congrats. That's so funny, the Dead Set Legend Cup. That's very Aussie. It's very, yeah. But yeah. Yeah. I got into this actually. I think I might have heard about buying websites in twenty thirteen.

They call it something else now. I don't know what it is.

And I bought my first one in twenty fourteen. I think I ran into Yarrow Starik at a which I'm sure you've maybe seen talk or met maybe met. Have you met him?

Yeah. Yeah, he was on my podcast when I first started my podcast in twenty twenty nineteen, and he was one of the first guests, actually. And then I sort of found out about it 'cause I heard him speak about buying websites or buying small internet businesses. It was still called the internet back then when I met him.

We call it the internet now; you look like a dinosaur.

What are you supposed to call it now?

I don't know, it's just yeah. Yeah, cool. So how did people start finding out about you selling deals and being good at that? And how do they start approaching you before even a website broker, yeah, website broker?

I think it was just because I listed basically exclusively on flipper.com back then. And I guess it was just that my listings were getting a lot of attention. Back then, the algorithm was a bit different. The higher the engagement that you had in your listing, the higher up on all of the searches you would be.

And so because I basically engineered that to get as much engagement as I could on each of my listings, it got lots of attention, which meant it got lots of beards and lots of eyes and lots of fires wanting businesses that I listed. And you know, I would even buy some businesses.

My whole period was usually around twelve months. So it wasn't very long. I would do what I could with it, and then I would sell them. And it was almost always content sites too. So that's sort of my background also. I I it's I do broker e-commerce and SaaS businesses as well, but my expertise is probably closer to content businesses.

I think that just because it was a public marketplace, it was getting lots of eyeballs. There were people out there that were seeing me getting good results and not doing so well themselves. And they're like Can you do it for me? I think that's where it was. That's what it happened.

It's so cool because it's such a great market for you being on Flipper and a lot of people hearing about it and going, I can sell my business not knowing how to do it, trying to list it, failing, and then going, Hang on, Joe is a beast at this. Like, how do we? So it's a really good place for you to be, isn't it?

Yeah, yeah, for sure. And especially back then. Like, even now there's just don't know what they're doing, despite there being heaps of resources out there, and the marketplaces are better at helping you design the busin the the listing.

Back then, there was none of that stuff. So you kind of just had to figure it out. And I had obviously figured it out. So they were like, Well, save me having to do it, I'll just get you to do it.

Yeah. No, it's so cool. Now I've got so many questions.

You've done over three hundred transactions, you know, and what's, you know, what's the single biggest or the most common sort of mistakes that people who want to sell their business make? Why do they fail and have to come to you? What are you know, what's what kills this deal or just you know.

Yeah, I mean I would say that, you know, it depends. You've got businesses.

Most of the people who are coming to me wanting to sell their business have sort of checked out already. They're sort of like, I'm done with this business, and I have been maybe for even a year. And I'm just I just don't want to have to deal with it anymore. So the biggest mistake is just letting it go.

For sure.

You know, we see many, many one of the directives that we even give in, like the broker agreement before they even sign up, is keep running the business as you have. Please just keep running the business because the worst thing that you can do on a sale is if the business starts to come down while it's for sale.

We have to keep lowering the price and lowering the price and lowering the price. And it just doesn't show a lot of confidence about the business. Even if it's a great business, the reason it's declining is that they're not spending time on it.

The buyers are still going to see that as a trend that is going to continue after they take it over, which is not always the case. So that would be the number one mistake that I would see most of my clients doing.

And I would advise, you know, if you're gonna list it for sale, just don't check out. Keep running it until you've got a buyer, and at least until it's an LOI, you know, you've got an offer.

Yeah. Yeah. I think even whilst there is an LOI, it's worth staying pretty involved in case that LOI or, you know, something happens in DD. Obviously for smaller deals, you know, they move a lot faster than, say say an e-commerce brand or a software business.

You know, when I'm acquiring something in the seven-figure range is due diligence can take a little bit longer, and finance can slow it down. When you're looking at, you know, what a hundred K to two hundred K deals, even up to t300K, mostly cash.

They're moving a fair bit faster than these seven-figure deals, right? Yep. Yeah. And that's typically the range you're in. Now whilst we're talking about ranges, what range do you roughly go from, like ten to five 100K ish.

That's right. So we have prided ourselves in always representing the little guys, so we want to continue to be able to service them in some form or another. The field has changed a little bit. It's a little bit harder now to sell smaller businesses than it was back in the day.

But we still represent businesses as low as ten K, even a little lower, depending. And then all the way up to, well, we don't really have a limit. We had a LOI on a business for four mil recently. So, you know, we can play around those ranges, although I think our sweet spot's sort of around the low to mid six figures. Yeah. That's where we took it.

The reason I asked that as well is because with that many transactions in that range, I mostly share with people that those transactions are mostly cash. Are you seeing that? Maybe you've got like ten, twenty, thirty, maybe forty percent seller note earnout type performance space. But that's right. Are we looking at most like, would you say like under a 100K is like just pretty much straight cash? And then a 100K to 500 is like a little bit of like seller note.

Yes. We are seeing more and more of that, especially things like holdbacks. Because the market is quite turbulent, buyers are a little bit hesitant. And if the business has only got, like, if it's volatile or if it's only got one or two sources of traffic or revenue, that can put buyers in a bit of a position where, like, well, what happens if to this to this?

To sort of offset that, I'm a deal maker. I come up with ways to make the deal happen. And if that means negotiating some seller financing, which is, as you refer to it, seller notes- same thing.

Then I will do that in order to make the buyer feel a little bit more comfortable in the deal. Holdbacks are something that I've been doing more often, especially for smaller deals. In fact, ironically, we've just done one, or we are close to closing on one that's for 15K with a 2K holdback. So the holdback is conditional.

Yeah.

Sixty days? Sixty-nine days?

Something like that.

Yeah. So it's not long. It's not like it's just, okay, we need some confidence before we're prepared to pay what you're willing to pay for it. We want some time to see this working.

Yeah. Okay.

We release that last amount. Typically with a holdback, the money is in escrow. So it's being held, and and it's it's on the table. It's not being used. It's not for capital or anything like that. And so that way there is some security for the seller as well.

So long as the business continues to perform. And it's also good for the buyer as well, because you've got the the seller is going to want the buyer to succeed. So they get the last amount. So they will be helping maybe a little bit more through that support period.

For sure. It sort of ties a seller into keeping the relationship alive. Even on a s fifteen K deal, it's so valuable. The relationship is so valuable, and so you said it was conditional. It was- what was there any other condition, or was it just sixty days? Like what other conditions were there?

This one was based on revenue, but you can make it on traffic. So, you know, it just depends on what's important to the buyer. And obviously it has to be reasonable; it has to be something that both the buyer and the seller would be happy with if it hit.

But obviously you're trying to go higher. But that's it shouldn't be, okay, so let's just say the the business is making a thousand a month and it's a six it's a ninety day, so three months. You can't have the minimum at three thousand.

You know what I mean? You want it lower than that so that there is some room, so that there is still some security. And, you know, if, say, it's at like two thousand nine hundred, it's like, well, that's still pretty close.

It's gotta be okay. Even if it was a little bit lower than that, so on. But this is what I do, you know, I'm a deal maker. I love coming up with solutions to solve both the buyer and the seller's concerns because they both come to the table wanting different things. It's like, okay, where's this middle ground? What is it that's important to this, and to this that is in the middle to make this thing happen?

And sometimes there isn't a middle ground, and you just have to walk away.

Yeah. Yeah. I'm a deal maker as well, you mostly on the sell side, and me mostly on the buy side. It's also my job to make sure we can meet in the middle. And one of the things that I share that is the most important is for my buyers to straight away start to build a great relationship with the seller.

Because the tr the level of trust that you have in each other the buyer and the seller means when these little things come up or something even big comes up, you can sort of allow some that relationship, the better the relationship is, the more trust you have, the more you can start to go, okay, well it's fine, we'll work it out.

We'll, we'll both meet where we can meet versus I'm here, and I'm stuck, I'm stuck here, and I'm staying here no matter what. Stuff you on one side versus and that's just that's where deals don't happen, right?

So do you do you want to have you done any deals in person where you've actually gone or had the buyer and seller meet? Yeah. So I'm beginning to realise, especially when you're starting to get seven figures, that that is like grease to the to the to the cogs of the deal. Yeah. And it can go a long way to make it happen.

I've got a seven-figure econ brand where I'm gonna have an initial call. It's looking good. We're probably gonna go to LOI, and if we do, we'll get them to meet because they live twenty minutes from each other. states.

That's lucky. Yeah. It's our leverage in the deal actually is the closeness, the relatability to each other, and then also makes it harder for people in other locations to not acquire as well because of the location thing.

But also, I have clients that would go away and find, like, they would live about thirty minutes from each other, and they went into one of the stores. They didn't let themselves know that they were possibly buying the business, but they just bought a bunch of stuff and tried it on and then went back to the store when we had one of our calls with the seller.

We mentioned that, and that was just over the moon. They were like, Okay, these guys aren't just here to just like kick the tires; they've gone bought from us, checked out the customer experience, all that sort of stuff, and it helps so much. As you said, it's a pretty valuable tool.

Well, that can happen online too. Yeah, it happens all the time. It's part of due diligence. If they're selling, like, a digital product or even a physical one, it's like, okay, I'm gonna buy something and see how it goes. Pretend to not just be a customer.

Yeah, and just to understand the buyer's journey, the process of where it's good and where it's not so good, and see what value you can add to it. With these deals, I don't know which avenue to go down, like the content space, the content website space now as it lands after all the craziness, or talking about where sh somebody should start if they're looking at something for it between the 20K to a 100K range.

So maybe, maybe let's just start with the content and then content like where the content space is now and valuations and content websites because that's a big subject and we'll move on to like what you think is a good deal in that specific range.

So I guess I'll just open the mic up for you to share because I can go down different routes and what's happened and why. But yeah, just what where are you what are you seeing and how it's evolved, I guess, since twenty twenty three.

Yeah. So I mean, first and foremost, if you're new, it doesn't really matter what happened in the past. It's just a matter of looking forward. Okay. What's working now and what's working what might continue to work, and moving forward. But content sites have definitely changed.

You know, it used to be all about SEO and Google and getting organic search traffic. The days of that are more or less in the past. Today it's more about brand, and most of especially for the smaller content sites, you'll see they're getting traffic through creative means, which means things like social media and YouTube.

I've even seen one where they're advertising with Taboola and then selling an affiliate product. So little sort of arbitrage ways, tr clever ways to get traffic in the door. So those are the typical content sites that we see. So like the classic example is something like a recipe site. Recipes are massive on Pinterest.

They generate a lot of traffic. Get the advertising dollars from the traffic from Pinterest. There are obvious risks in there because you've only got basically, in most of those cases, one revenue source or one traffic source. And if that, you know, Pinterest or wherever the traffic is coming from decides to change the rules on you, you know, then it's basically game over.

So what we want to really look for are things that are a little bit more diverse. You want something that's got at least two revenue sources and at least two solid traffic sources. So then if one of them disappears, at least you've still got something to work with.

And again, depends on how small you're going here. If you if you're looking at like a 50K business, the chances are there's not going to be a huge amount of diversity.

And when you start going up to, you know, six figures and up, you start to see a bit more diversity. And I would be requiring it at that point. Revenue, yeah. Revenue mostly, because that's, you know, and then you can, depending on the profit margin, you can play with those profit margins a little bit more easily. Yeah. I will just mention, I want to say in revenue, you mean revenue on traffic.

Yeah, absolutely.

Yeah, that's what I mean.

Yeah. It's a double-edged sword. It's both really, really good for content sites. People can shine content out so quickly, and it's really quite good.

Yeah, it's ranking. It's crazy to see.

And it happens quickly. And you can build things so, so quickly these days. And I mean, I'm quite bullish on AI. I think that for the most part, it's really, really good for the market long term.

Short term, people are reeling, going, Whoa, what's going on? Like, you know, the whole landscape just changed completely. When Google started doing their AI modes and stuff like that with the snippets and stuff, things like this, it's like they're stealing all my traffic. I think that, along with running a business, a content business, I think that thing you need to focus on is if AI really is the future, how do you appear in mentions and things like this to a consumer who is using AI to find that?

And the only way that AI, at least as far as I'm aware, can find out about things is by doing Google searches or searching. So you have to still start with SEO. You have to start with the SEO and have the foundation solid. Otherwise, the AI is gonna find you anyway. So I think that's an important point.

You've answered it so well. SEO is not going away. And your search traffic from Google has been going away for many years. Zero-click searches are a thing. If you go into Google now, you can kind of prompt it like Claude and ChatGPT, where it's moving, and you can have way longer questions and get snippet answers without having to click through the sites. So those websites aren't gonna be generating that much traffic from Google.

Yes, you need SEO to be able to rank in Google and to appear in LLMs. At the same time, what's happening with Google is zero click; it can also be zero click in LLMs as well. Because I'm not, I will rarely go and click on a website to go away and check something and how it's written to view the website.

I just stay on the platform, and I get the answer. And so the way I like to think about it for content sites is, and you probably were gonna go into this anyway, or you mentioned it earlier, is brand. Like, how do you turn your content and website into a brand and sell products, even if they are drop-shipped or affiliate type products, because where ChatGPT and they're just releasing it now, and Claude's going as well, is like I'm not gonna go away and click to check an answer that I can get on platform from Claude or ChatGPT.

But if I'm gonna buy something, I'm not gonna buy it I'm probably not gonna buy it straight through Claude or ChatGPT yet. Maybe in a year when I can see how it works. But even if I can buy it through ChatGPT and Claude, I'm still making the money because they're buying it through that; like, the ClaudeBot will be buying it through my website anyway.

So that's the way I see it. And it's crazy that people might think, well, why would I not c why would I create content and continue creating content? Well, you need the content to rank, and you need the content to build the authority. And you need the content to bring in the user to show authority in that space before they go away and buy your product and service anyway. And that's how I think about content sites moving forward. There's still so much value in them.

It might be challenging to be a media site where you have a lot of people land and a lot of eyeballs to promote and advertise, but you can still draw a lot of money from these content websites. It's they're important. What do you think about that?

Yeah, so I think that the days of ranking and getting traffic from how-to and what is those sorts of informational base keywords. For sure. You're not gonna get much traffic, especially through SEO for articles and blog posts or whatever like that, as you used to.

What you need to focus more on, I think, is brand, like you said, or service, something that is yours that you can sell. So things like agencies we see doing really well. SaaS businesses are still solid.

Like they're still super desirable. They're still probably the best source of monthly recurring revenue, which is very desirable, especially if it's predictable. And, you know, I think that those are probably one of the most important things to remember.

If you can do what you said before about the authority. So using those articles instead to prove that you know what you're talking about and as a source of authority is the play. You can still get backlinks and things like that.

To those articles from other sources that boost your business and your website's authority. I think that you have a new, yeah, yes. And you know, if your SEO is bad, AI is not gonna know about it. So you've got to rank to show up first in what are they calling? GEO this these days.

Yeah, G E O I E O whatever.

Yeah. There are so many.

It's basically the same thing, in my opinion, because how are the how's the AI gonna know about it? The w only way that they know is through search.

Yeah. AI is obviously gonna search and look for authority as well. Right. Like, why would they get an answer for somebody from an important subject that's not an authority? All right. It's like, yeah. They're an authority, and you know, AI is really struggling with this anyway. It's how answers are not that accurate and how it's not accurate anyway.

So they need to tighten this up and get better at their SEO anyway, in my opinion. That's their game now. It's lagging, in my opinion. Humans have caught up, and we are holding these LLMs accountable now to be better, which is good. No longer are we like, Whoa, hang on, how good's this AI thing? It's like, hang on, this thing still needs work.

We're in the tech space, though, you know, like I think most of the people who are listening are very involved in AI, and I occasionally just ask my completely non-technical friends. I'm like, So what are you using AF AI for? And they're like, just an image here and there or something.

They're just they just don't understand how impactful it can be and why it's such a big deal. Like, like you and your audience do. Which is so awesome for my buyers and people looking to buy a business is what I'm trying to share.

It's like, yeah, it's like you said, there's some perceived volatility on buying a business because people could be worried about AI and search and whatnot. But it's the best time to be an online b it's one of the best times to be an online business ever. Where I actually agree with you. It's insane. Where you can buy a business that hasn't got its operations streamlined by AI.

You can cut operation expenses so fast and so easily and make a business so much more profitable when you go away and buy it. It's for a buyer right now; I think people are crazy to sit on their hands. And this is: I don't care if people don't buy businesses.

That's fine.

Like it's I'm not trying to; I am biased towards it, of course. It's my job, and I make money from this. But if I don't make money from this space ever again, that's all good. Like, I just still think people should be out there, whether you help get help from me or anyone else, like go and buy a business. Like the leverage right now is insane.

If you don't want to buy. It's never been easier to start one. I remember when I first got started, learning how to use WordPress, learning all about how to, you know, host, and I even learned some HTML and, like, using c panels and all of that crap, man. You don't need to do any of that anymore. That's a good point. So hosting and stuff like that is just taken care of, as AI can just pay for your host.

Run into a problem, you take a screenshot, and you go, This is my problem, and it will solve it for you. It will tell you exactly what to do, the menus to go to to fix the thing. Like it's never been easier. And you can build anything you can think of.

And you know, a lot of people are worried about, like, AI taking jobs. We've recently promoted one of our staff to be full-time so that they can work on all of these ideas that we can now implement. You know, just a really simple example of something that we use internally.

That we built with AI- I built with AI in like one or two days. It's a QA for me. So, say a buyer comes to me; they have a lot of questions about the business. We've already done all the work. We've got all the documentation.

This is what AI is good at. Figuring out the answers to these questions. So long as we've got the questions in here. So this internal tool that I built, you paste in all of the questions, and it answers them for you in a way that we can literally copy and paste.

Yeah, and just create a building. Yeah. I mean, just I think about that when I look at listings now. I'm like, this is a hundred percent AI. Like, I can tell this because I know what AI spits out. And why wouldn't you use it? It's attractive. It's written in a way that, like, a buyer is gonna go, Pfft, this is a great business. Obviously for me, looking at thousands of tens of property towns with thousands of deals, like I can tell I can see what's not what's invisible, right?

But it's very attractive, and it works very, very well on the sell side. It's super dangerous in due diligence. Super dangerous. It's great because it can reconcile numbers and everything like that, but it can't see what an advisor, say for myself, that's done this so many times, it can't see what's not seen, and it can't ask questions it doesn't know to ask.

Spending X amount of time on the business, and I haven't got a really good example to cite that's coming to my head. But sorry, I'll give you an example. Two now that have just come to my head. The first one is I put a business in, analyzed it, looked at it, and AI said, but this business is going backwards by ten percent year on year. And I'm like, this is not accurate.

Like I looked at the I looked at the thing and was like, it's going up ten percent year on year. And if anything, it should be valued more. And Corb was like, My apologies. Yeah, you're right. It's a good it's a better deal than it looks like. And but I got a better one. I got an even worse one as an example. But this I just say this as an example- this first one, because people will just go, I walk away from that deal.

How long ago was that? That's a bit two, three months ago.

But that's an amazing opportunity that is more valuable than what people can perceive. But I was able to see it because I've looked at so many of these before. Right. Now we've also analyzed, and we're about to go through finishing up on a deal where they had somebody in the business that only started, like contractors only started four months from listing the business, but it got itemized out as though their contracting wages were over twelve months.

So their per-month contracting fee was a lot shorter because they got itemized out over the twelve months, not just the four months. And so obviously the business looked far more profitable, but it wasn't because I think it was about a hundred and a hundred and seventy-two grand. And I created a separate YouTube video on this if you want the full example for people listening. It was about 172 grand; we misvalued the business by.

well. Up or down. Down.

Because I down. We, it was gonna be yeah, it was gonna cost us more. A hundred and seventy-two grand more, sorry. Yeah.

I think that at the end of the day, it does make more sense for the AI to be more cautious. I wouldn't I would prefer it be more cautious and say, this is not so great; don't do this, than " This is fantastic; do it. And it's really not. Do you know what I mean? So I think that if you're gonna pick one or the other, it would be this way. I think that it is unwise to be implacable. If you do that and you re rely too much on it, I feel myself doing this, and I'm trying to resist it.

Precaution as well.

Jaryd, can you hear me? Jaryd, can you hear me?

Yeah, I've got ya.

Okay.

Sorry about that mate.

Gosh, I lost my train of thought now. Where was I?

Wood is talking about how cautious AI is. I would prefer AI to be more cautious than just make me feel good and happy and keep me on the app. But that's what they want: they want us to be happy with the service and give us answers that make us feel good to continue working with it and continue using it. But the accuracy is and I'm sure there'll be different LLMs for more accuracy as this goes on- but it's sketchy, man.

It's sketchy for people buying businesses. You know, I just think people are gonna go away and copy and paste a flip listing and put it into the chatbot and go, Should I buy this? What are the red flags? What am I missing? And you just, like, but some people will be doing it.

But that's the lazy way.

Yeah. Well, hopefully none of your listeners are gonna be doing that. Because we're telling them, don't do that. You wanna you wanna basically customize your systems, right? So you've gotta think first and foremost, before you go on any AI, what do I want? What do I want? What is most important to me?

What am I looking for? And it could just be what we've been talking about today, you know, diversity and so on and whatever. And figure out what it is, and then from there, go input that information into the LLM of your choice. Give it as much context as you can. It's okay. This is my background.

This is what I do. This is what I'm good at. This is what I'm not good at. The more context you give it, the better the result is gonna be. And you can tell it. It's like, don't tell me to buy this. Don't tell me not to buy this. Just give me the facts. Just tell me what I want to know and nothing more.

Don't make those decisions for me. I'm gonna do that. That's my job. And you can make that very clear right at the gate, right at this at the start. And that's the way to avoid a lot.

You're ahead of most people just simply by doing that.

Yeah, totally agree. Yeah. The reason I bring it up is just it's a word of warning. People need to be very careful. It's like your life savings on the line, and yeah. Maybe your life savings, I don't know. It could be- yeah, hopefully not life savings.

Yeah. This is why if you've got, if you're spending a decent amount of money, you should be hiring somebody or at least having somebody look at your work and your due diligence, right? Or just hire a due diligence service to do it.

Well, hopefully not.

At least buy or sell side. Yeah.

Yeah. Both. Yeah. Absolutely. Yeah. Buy or sell side. What about somebody that's coming to the space and they've got anywhere between 20K to a 100K to spend on a deal? What do you think they should what's a good deal looks like between 20K and a 100K? What should they prioritize? Like should they be trying to prioritize niche, revenue model, traffic? What are your thoughts? Like if you had 50K or something around there?

And you're gonna buy your first site as a beginner.

This is super individual. If I was having a coaching call with somebody, I wouldn't just give them the answer. I would be asking them questions like, okay, what is your background? What do you do? What are you good at? What do you think that you want to do once you've purchased the business?

How involved in the business do you want to be? Do you want it to be passive? Do you want it to be yeah, those are the most important things. But let's assume that you figured those sorts of things out. Some things are generically across the board desirable. Growth. There needs to be some element of, at the very least, stability.

And if the business has been around for a long time, that's obviously more desirable. Even if it had previous, like, you know, in COVID or something, it had a massive spike or whatever, and then it's come back down, but is now stable. Like that's something that typically you want to see. We've already discussed it. Diversity.

So diversity in traffic and revenue, those things are most important. To be honest, outside of that, it really just comes down to personal preference. You know, if you're, you know, really into sports and you really love watching sports, like maybe you can take that.

And look for sports sites specifically. If you really love, I don't know, fashion, maybe an e-commerce fashion store might be something that you'd be interested in. I think the c the mistake that I think I made when I was getting into this is not following my passion. I would just follow the money.

If it was the sites that did the best for me, they were the ones that I was legitimately interested in the content about. Like creating content about this thing was interesting. So one of the things that I do as a hobby is CrossFit. And so I built a CrossFit site. Well, it wasn't CrossFit.

Cross it adjacent.

Before CrossFit, yeah.

No, it was this. It was, yeah, right. I think it was about 2015, 2014 that I built it. So it was still very much a thing. And anyway, the point is that I really, really enjoyed doing content for that site, and it did really well. Yeah.

I don't own it anymore, and I did sell it, but ultimately, like, that was exciting. That was fun. And I think that that's first and foremost. It does need to be exciting. If you buy a business and you think it's boring, you either need to have someone else run it for you or don't buy it. So I think that would be my advice.

Both Crossfield was still around. Okay.

The price that's realistically for any price range. I think this advice can be for anything. It doesn't matter how big it is. You've got to be into it. And if you're not, it's probably, unless the systems are super, super strong and there is a good team around it, chances are you're just gonna get bored of it in a year or two, and then it won't be doing as well.

So yeah, I agree with you on when you first started looking, just chasing the money, I was the same as I was just buying businesses just to make money and get out of my plumbing job.

Absolutely.

And what I found is that I didn't fall in love with the products. What I fell in love with was business. I fell in love with working out how do I how do I grow this business. And so the niches and things weren't something that I was super passionate about. Like, I bought a suit business, and I bought a furniture business.

And a drop shipping directory site. Like, I couldn't, like, surfing is my, like, passion. But there aren't really surfing sites out there. I've seen some, but they're just not very good, and I don't want to buy them.

Yeah. But I did find value and excitement in learning to grow the business, which is something that could help people as well. It's just cause when some people are like, I'm passionate about this thing, it's like sometimes it can be pretty hard to find that, and they might be looking for like two, three years to find something, and when they do.

Good point. Yeah, you've got a very, very good point. And I agree with you. You know, my dad, when I was first getting into this, he's like, Can you find any fishing sites? And I'm like, Yeah. That's pretty hard to do. They're pretty few and far between. You've got a good point.

It's not great.

Yeah.

Like fishing and pets are like great, amazing niches to be in.

I think that, you know, the site that I mentioned I built myself from scratch. So that's probably more that angle.

The other, I mean, once you've got one site under your belt that is performing well as well. So if you've already got a portfolio of businesses, you can buy other businesses that complement that.

And I think that that's another strategy that a lot of portfolio buyers do very successfully. Because then later on, you can package all of that together and sell it all together, and it'd be more valuable because again, you have diversity. You've got multiple things here.

Yeah. Yeah, it's like what we mentioned: say you're buying a 50K content site in fishing, right? And it's got a lot of fishing tutorials, and it's got a lot of value around fishing. And it's making a little bit of money from affiliate revenue, and then you SEO optimize it to get picked up by LLMs, and it's doing quite well. It's got a single source of revenue. And then you go, Well, I wanna grow this, but maybe I just go buy a fishing e-commerce business for 50K or 100K, and you run those alongside each other and cross-pollinate traffic and revenue from that.

Yeah. And you can build, then you build like, say, a 150K portfolio of two businesses where you can merge that into a brand. Maybe you could if it merged two sites somehow. Maybe the fishing e-commerce brand doesn't have a big authority, but the content site does, and you go under one banner and one domain and build out, you know, bigger authority that way. It's obviously, you have an SEO check. This is just an example. You'd have an SEO do that work for you. But it's an example of how you can grow a content site today in 2026 and moving into 2027 and make it work. Because you're right, like I don't think content sites have no place on the internet ever again. That's not what I think. It's more about people that have come to this space.

They've gone from these sites were crushing it in twenty twenty two, twenty twenty one, and then twenty twenty three happened, and then we see the big decline. But for the last two years, we've seen a lot of these content sites stabilize and settle out, and that's what you want to buy is stabilization in a business for sure.

I think that there's a point that you made there that these LLMs are trained on the content that was produced in the past. They know as much as they do because the content was out there, put out there by humans. I think human-generated content is going to be, at least for the next couple of years, underrated in that the AI can put all of this information together really quickly and easily, but there's very, very rarely going to be any original thoughts in there. That's where the humans come in.

You need to have these original thoughts. You have to. It's important. And I think that the more originality you can have in your business, the longer it's going to last.

Yes, absolutely. And the more trust. That's probably going to be the longer it's gonna last 'cause there's gonna be more trust in it.

So yeah, Joe, thanks for coming on and sharing. It's been so good. You've got something to share with the audience that you built. Report tells us.

Yeah, so I spent some time. I was thinking like, what would be really good for both buyers and sellers interested in this space? And I've got a lot of experience buying and selling businesses, and I've done a lot of research over the past few days, and I've put together this report, which is basically a state of the market for 2026.

You can easily download it by going to just website brokerage.com forward slash 2026. That will take you to the landing page where you just enter your details, and you can download the report; it'll just get emailed to you.

There's quite a bit of information in there, but I've made it extremely bullet point worthy and easy to consume. So you can just rip through it in just a couple of minutes, and you'll get a baseline.

Yeah, I've gone through it, and it's a lot of research condensed into easy-to-consume content.

Yeah, I didn't want it to be this bloated, boring I've gotta read this. Because I hate I don't know about you, but I really struggle reading nonfiction because I just I'm like, it just goes on and on. Some's fine, but man, if it's I'm not; I don't learn from reading; I learn by listening to podcasts like this. Yeah. And I presume that your audience is similar in that, well, you know, it's easier to listen to it, and because I have to do it as a bite-sized thing, it's better that it's just boom boom boom.

For sure.

A multiple chart and things like that for different business types and other things like that in there. So hopefully it'll be of value to your audience.

I'm sure it will be, guys. There'll be a link to that in the show notes. I'll also put it in the show notes. Well, it's just website brokerage.com, Joe's site.

So check that as out as well there if you're looking for businesses. He's got a bunch for sale.

And Joe, thanks again for coming on. Really appreciate you.

Absolutely.

Everybody who's listening, thank you for listening. Also, before you go, I don't normally ask for favors ever, but if you've listened to maybe five of these podcast episodes, or maybe ten, maybe, I'm sure you've got some level of value because you keep listening.

My pleasure. Thank you for having me.

And if so, please be open to just putting in a review and letting me know what you think. I'd be super grateful for it.

Thanks, guys.

Host:

Jaryd Krause is a serial entrepreneur who helps people buy online businesses so they can spend more time doing what they love with who they love. He’s helped people buy and scale sites all the way up to 8 figures – from eCommerce to content websites. He spends his time surfing and traveling, and his biggest goals are around making a real tangible impact on people’s lives. 

Resource Links:

➥ Connect with Jaryd here – https://www.linkedin.com/in/jarydkrause

➥ Buying Online Businesses Website – https://buyingonlinebusinesses.com

➥ Download the Due Diligence Framework – https://buyingonlinebusinesses.com/freeresources/

➥ Sell your business to us here – https://buyingonlinebusinesses.com/sell-your-business/

➥ Google Ads Service – https://buyingonlinebusinesses.com/ads-services/

Buy & Sell Online Businesses Here (Top Website Brokers We Use) 🔥

➥ Empire Flippers – https://bit.ly/3RtyMkE

➥ Flippa – https://bit.ly/3wGa8r5

➥ Motion Invest – https://bit.ly/3YmJAmO

➥ Investors Club – https://bit.ly/3ZpgioR

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