In short
Live walkthrough of buying online businesses for cash flow in 2026—where to find listings, how to evaluate pricing/multiples, what due diligence to do, and common buyer mistakes (including lack of a post-purchase plan).
Guest
Joe Burrell, broker from WebsiteBrokerage.com; has helped broker 300+ online business sales totaling $7M+ lifetime value; started buying/selling in 2012, became a broker around 2018, and now doesn’t run his own businesses.
Key claims
Use Flippa (NDA required) and apply filters like budget, business type, revenue/profit, and age. Profit multiples are based on average monthly profit; e.g., 2.7x implies ~2–3 years to recoup if performance holds. “Passive income” is a myth—sites decay without active management. Diversify revenue/traffic; verify analytics, P&L, and concentration risk (few articles driving most traffic).
Notable examples
pestkill.org (13-year content site; claimed ~$675/mo profit, 97% margins; AdSense + Amazon Associates; potential upside via ad network swaps like Mediavine/Raptive). surf-store.com (20+ years old; ~$5k/mo; listed at $83k; concerns: outdated revenue graph, possible inventory/ops complexity, EU-only reach). Assignment GPT (AI SaaS; ~2% churn claim; warns about AI cost dependence and “lifetime sales” being a bad deal). Also discusses faceless YouTube channel risk (YouTube dependency) and seller financing (more common >$50k; usually not ideal for first buy).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOIntroduction to Buying Online Businesses
0:22 to 0:52
Explore the opportunities in purchasing online businesses.
“And that's why when you need to get it right, think this is a job for Indeed Sponsored Jobs.”
Introduction to Buying Online Businesses
1:00 to 1:48
Explore the opportunities in purchasing online businesses.
“This is a job for Indeed sponsored jobs.”
Exploring Marketplaces for Business Sales
1:48 to 3:53
Understand where to find online businesses for sale.
“And so if I want to skip that part, it's going to cost me some money because somebody is going to get paid for that effort.”
Analyzing a Business Listing: Pestkill.org
3:53 to 5:48
Learn how to evaluate the value and potential of an online business.
“So we're looking at a website called pestkill.org, an established 13-year-old content site that says it is doing$675 a month in profit at 97 % margins.”
Understanding Revenue Streams and Monetization
5:48 to 8:10
Discover various ways online businesses can generate income.
“So then the investment is paid off quicker and then it's all gravy from there.”
Evaluating Risks and Negotiating Price
8:10 to 10:15
Gain insights into assessing risks and negotiating business prices.
“the overall strategy that the existing owner has put into place.”
Benefits of Buying Established Businesses
10:15 to 13:52
Explore the advantages of purchasing a business with a history.
“Almost always, the seller is going to be negotiable on the asking price.”
Exploring Potential Growth Streams
14:00 to 15:02
Learn about different growth opportunities for online businesses.
“in this area, you know, combine the pest plus location and then make a referral to such and such company.”
Transition to Surf Shop Discussion
15:02 to 15:13
A transition segment introducing the next business to analyze.
“Big parenting milestone for us this month.”
Introducing Financial Tools for Kids
15:13 to 16:44
Discover how to teach children about investing and financial tools.
“I finally set up investing accounts for the kids.”
Show all 26 chapters
Analyzing Surf-Store.com
18:04 to 20:08
Examine the financials and operational complexities of an online surf store.
“It's sort of evening out a little bit as to why it usually revolves around the style of the business.”
Strategic Considerations for Acquiring Businesses
20:08 to 23:03
Discuss strategic questions when considering the purchase of a business.
“if I only didn't have to come up with the idea and didn't have to start the business from scratch?”
Using AI for Business Analysis
23:03 to 25:06
Learn how AI can assist in evaluating potential business acquisitions.
“Yeah, you got me thinking from a strategic acquisition standpoint of growing the email list, of expanding the body of content in one quick hit versus having to do a bunch of writing and research all on my own.”
Exploring Financing Options for Business Purchases
25:06 to 28:00
Understand various financing methods when buying a business.
“The thousand articles that you think you're acquiring, well, most of them don't meet your quality standards for these reasons.”
Understanding Business Partnerships
28:00 to 30:06
Learn about the nuances of buying a business through partnerships and rapport building.
“It's definitely been done, but it usually involves some level of partnership and you've got to build quite a bit of rapport with the person.”
Intro to SaaS and Business Mistakes
30:06 to 30:25
Explore common mistakes in buying online businesses and the SaaS model.
“But I mean, there's still, we're still talking about a lot of money changing hands here.”
Building Rapport with Sellers
32:37 to 34:35
Discover the importance of building rapport with business sellers during transactions.
“So one thing I would recommend that buyers do is get to know the seller a little bit, especially on your first deal.”
Evaluating SaaS Business Opportunities
34:35 to 36:54
Learn how to assess software business opportunities and common pitfalls.
“The tagline is we help you with your homework doing around$2 ,000 a month, asking only$20 ,000 slashed from 40 ,000.”
The Rise of Faceless YouTube Channels
36:54 to 38:19
Understand the growing trend of faceless YouTube channels and associated risks.
“What do you think about buying a faceless YouTube channel?”
Marketplaces for Buying Businesses
38:19 to 39:21
Explore various marketplaces for purchasing online businesses beyond Flippa.
“Because if they're unique, they're difficult to copy, they're more valuable in almost every situation.”
Investment Trends in Online Businesses
39:21 to 41:06
Discuss the investment trends in online businesses and market changes over the years.
“So we actually had one LOI on a business for four mil.”
The Impact of AI on Business Strategy
41:06 to 42:03
Discover how AI is changing business strategies and operations for entrepreneurs.
“It was very easy to buy a content business for maybe 1x, a bit less than 1x.”
The Numbers Game in Business Acquisitions
42:03 to 43:48
Learn how strategic acquisition can lead to successful business outcomes.
“You buy 10 businesses, maybe five or six of them don't work out, but the other ones do really well.”
AI and the Changing Landscape of Content Businesses
43:48 to 45:26
Discover how AI is transforming online business strategies and traffic sources.
“Do you still see buyer interest on getting into this space now that maybe expectations are adjusted to a new reality?”
Key Insights on Business Consistency
45:26 to 46:05
Understand the importance of consistency and dedication in achieving success.
“So Joe, really appreciate you stopping by, giving us an inside look at what's going on in the world of online business acquisitions.”
Due Diligence in Business Acquisition
46:05 to 47:18
Learn essential tips for due diligence and planning before acquiring a business.
“thing constantly over and over and over again and just showing up and doing the work, even when things are a little bit tough.”
Transcript
Automatic transcript. May contain errors.0:00When I started the show 13 years ago, it was just me wearing all the hats. But as it's grown, so has the team to support it. And I'm super grateful to Adam for his editing skills, for Ava, who produces the video versions that you see on YouTube, to Sheila, who does the detailed write-ups for the Side Hustle Nation website, and to Teresa, who uploads everything to all the different podcast apps. When you're a small business, the right hire can be make or break. And that's why when you need to get it right, think this is a job for Indeed Sponsored Jobs. Spend less time searching and more time actually interviewing candidates who check all your boxes.
0:35Less stress, less time, and more results. When you need the right person to cut through the chaos, this is a job for Indeed Sponsored Jobs. Side Hustle Show listeners get a$75 sponsored job credit to help get your job the premium status it deserves at Indeed.com slash podcast. Just go to Indeed.com slash podcast right now and support our show by saying you heard about Indeed on this podcast. Indeed.com slash podcast. Terms and conditions apply. Need to hire? This is a job for Indeed sponsored jobs. Let's go shopping for some cash flow. Today, we're taking a live look at real online businesses.
1:14You can buy how much they're making or how much they say they're making, how much they cost, and what might make a good deal for you. My guest has helped broker over 300 of these sales, totaling over$7 million in lifetime value. From just website brokerage.com, Joe Burrell. Welcome to the Side Hustle Show. Hello, Nick. Thank you for having me. You bet. So let's say I'm this person. And I'm bought into the idea of let somebody else do the hard part, the getting noticed on the internet part, the getting the business off the ground, that zero to one phase. That's really difficult. And so if I want to skip that part, it's going to cost me some money because somebody is going to get paid for that effort.
1:53But where do I want to go to see what types of businesses are available for sale? Right. Okay. So there are a few public marketplaces that you can go to, and we'll name a few of them as we go. But the one that we're going to look at most, it's the biggest, has the most listings on there is Flippa, Flippa.com. Yeah, let's take a look if you are willing to share some of the listings that caught your eye. Of course. Yeah. As you can see, most of these listings, you have to sign an NDA in order to get access to these. What's your take on that? Is it worthwhile to, oh, that looks interesting to me.
2:22What would make it interesting enough to be like, yeah, I'll go through the, jump through the hoops to sign an NDA. Right. Yeah. So let's just click on one of these and you can take a look. So there is some information that you'll see for one of these businesses before you sign the NDA to get an idea on whether or not you're interested. And that basically will be enough to sort of go, okay, I'm interested. I want to sign. And that will get you access to a lot more information. So it's just that basic NDA and you would click the button and click sign. That's basically it. I don't want to spend too much time on that because what's more important is finding a business that you're interested in.
2:52Right. So let's go back to the browse. Just browse for websites for now. and they have a lot of options for what you can search for lots of toggles you can search for traffic filtered by the business type and so on on the left here so say you've got a mass budget or an industry you want a certain amount of revenue or a certain amount of profit you can put those in there a certain amount of age and search that way and then it'll change your results now if you're a new person shopping what are some of the must-have filters for you so your budget would be in there let's just say your max budget would be say a hundred thousand and you would want to put in the website types so say i'm after only content sites so i just check the content sites there and to be honest i'd probably try and keep it quite broad to begin with especially if you're not sure what you're looking for if you've got some idea then go a bit deeper but having a wider pool to look through especially when you're starting out it's probably a good thing because the chances of you buying the first thing you look at is very unlikely.
3:51So this one's called pestkill.org. All right. So we're looking at a website called pestkill.org, an established 13-year-old content site that says it is doing$675 a month in profit at 97 % margins. I assume it's just hosting is the expense there. And it's been around for a long time. Probably, yes. So I just wanted to pause on this profit multiple. So this is typically how businesses get valued. they they're valued on a multiple on the amount of profit that it makes so this is calculated from the monthly profit so it takes the last 12 months averages it out and then that is what the multiple so 2.7x is 2.7 times the yearly profit so assuming it continues to make exactly as it is it would take two or nearly three years for you to make your money back on that investment if you paid all cash.
4:45Does that make sense? Okay. So in theory, for the$22 ,000 asking price, you could buy yourself$675 a month in cash flow, which whatever, that's 30-something percent annual ROI. It pencils out a lot better than a lot of dividend-paying stocks. And because of that, there's volatility involved. There's going to be work involved. It's not going to be completely passive. Or maybe that's the question. Well, how passive is this transition really going to be? Yep. So the myth of passive income is difficult to come by and it usually involves some form of automations, which need to be upkept anyway, or some stuff that need to be sort of managed.
5:23Yeah. I wouldn't go in with that mindset personally, because if you just buy this site and you just do nothing with it, it's going to suffer for it. Slowly decay. Exactly. The way that the most successful buyers do it is that they buy the business with a strategy in mind in order to improve the profit, improve the traffic, improve the business in order to get the profits higher. So then the investment is paid off quicker and then it's all gravy from there. So you almost have to come in with some webmaster experience in the example of buying a content site. If you've never logged into WordPress, if you've never written a website, blog article, SEO article, this is yeah it might make$675 a month for a couple months but slowly if you don't know what you're doing you're just kind of buying yourself a ticking time bomb right so let's dig into this a little more so every business will have a business description and this is usually written by the seller this graph that we're looking at here is essentially it's a line chart of the profit and the revenue per month so obviously we know that the profit margin is very high so there's not much of a gap between the revenue and profit but i wanted to just highlight this as well so So this AdSense revenue, Flipper has the ability to verify some of the revenue that comes in without you actually having to look at it.
6:41This is all done through the API, so you can trust that it's pretty accurate. You still want to double check the figures because they can be off a little bit, but this line here is AdSense revenue only. Okay. So that basic question, okay, well, what's the rest of it? There's obviously more revenue. So in May, it did 957 in revenue for AdSense, but the total revenue was nearly 1 ,200. So we'll come down here. If we click on this, it's opening up in another tab. But for an experienced eye, Amazon Associates screenshot of the revenue for the last month that they input. So that answers the question really quickly.
7:15That additional amount is going to be the Amazon Associates, which is Amazon affiliate. Okay. So relatively simple site, primarily monetized with AdSense and supplemented with Amazon Associates. We can monetize the informational-based content with display ads. Maybe as a buyer, you're like, oh, I have a path to get this into Ezoic or Mediavine or Raptive or something that is going to have better payouts than straight AdSense. And for the commercial intent content, okay, that's monetized with affiliate partnerships. So maybe you have a path where you could say, oh, I know how to increase conversions on that side.
7:54And if you're just looking at the site, like, oh, here's some things they aren't doing that they naturally could be doing. And on the revenue chart, there appears to be some seasonality, like, okay, spring is big pest control season. And so there's a spike there and it's kind of flat the rest of the year. But that's kind of, it gives you a sense of where the revenue is coming from, kind of the overall strategy that the existing owner has put into place. Absolutely right. Yes. And it was one of the opportunities that I quickly highlighted. Basically, AdSense is well known to be one of the worst display advertising networks in terms of how much they pay out.
8:29So just switching it to another one like Mediavine or Raptive, if they'll accept you on their platform, you're going to increase the revenue just simply doing that. Yeah. And at 10 ,000 page views a month, it may not be whatever their traffic thresholds are. So that's something to consider. but maybe if you can grow traffic, there's a path forward where if you can apply some of the existing skills you have, all of a sudden your breakeven window becomes much, much faster. Yes, correct. That's exactly what it is. That's the name of the game. Probably the most desirable thing for a buyer is diversification.
9:04So by that, I mean diversified revenue and diversified traffic mostly. If you're buying a business that has clients, then obviously you don't want to buy business that only has one client because obviously if that client disappears, then so does everything else. Yeah. And would they give you analytics access to say, okay, where is the traffic coming from? Yes, exactly. So one of the first things that most buyers will ask once they're interested in the business is, can I have access to Google Analytics? Can I have the P &L and anything else that's required to verify that P &L? So screenshots or a video call with the seller going through that information.
9:41And what you might find if There's like 100 articles on the site, like three of them drive 90 % of the traffic. And it's not altogether uncommon, but it's another risk factor. Like, well, if you lose ranking on one of those posts, then all of a sudden your expected income needs to be adjusted downward in a hurry. Yes, correct. You got to do some pivoting if that sort of thing happens and try and change the path of the course. Is this 2.7x on annual net income? Is that typical for what you're seeing in terms of multiples or valuations these days? This is the asking price. Almost always, the seller is going to be negotiable on the asking price.
10:21So just keep that in mind. Most of the time, you can usually go under it and get a better deal than what is currently listed. It depends on how good the deal is and how serious you are about purchasing, because we do have some buyers who are serious. And if it's a business that they want and they know they can do well with, they don't mess around like, fine, you can have asking. Let's just do the deal. But I wouldn't recommend that for most people listening. There's usually some negotiation that happens there. Given everything that you can see, at least publicly, what's a fair price for this pest kill site?
10:51We would need to take a closer look at the details. But essentially, I'd say that this is fairly well-priced. I wouldn't be surprised if this ends up selling for somewhere around$15k to$20k. That is sort of where I would be expecting it as a broker. This is without having looked into it. There might be some skeletons if you dig into it, something wrong with the business or whatever. Obviously, another very important thing is to obviously go to the website and check it out. So you're doing a bit of detective work, making sure that everything that they have claimed is true. So you're verifying that as best as possible.
11:24Yeah, it's an interesting one. And you're like, well, what other assets does the business have? Does it have a social following? Does it have a YouTube account? Does it have an email list? I was close to acquiring a business last year where there really wasn't any traffic to speak of, but it had an email list of like four or 5 ,000. So I was like, well, that would be interesting to acquire that database and fold them, fold the existing content. It was like case study, entrepreneurial content, fold that content into the Sine Hustle Nation umbrella and hopefully warm up this email list into the Sine Hustle Nation community as well.
11:58Yes, that's right. In Flipper, it will tell you more or less what's involved, what's included in the sale. So we can see here it's built on WordPress. The domain name is included. There's email addresses, website files, social media accounts, brand assets. And usually in the description, there will also be a detailed list on what's included as well. So make sure you look at that. And if anything's unclear, so if you find something that's connected to the business and it's not stated to be included, you need to make sure that it is, especially if it's an important part of the business. The other piece of this is kind of the, okay, we'll say it sells for$20 ,000 or that's going to be the fair price.
12:33The question is, well, could I, for less than$20 ,000, rebuild in my own way the content architecture of the site? And I guess essentially what you, I mean, you're buying a 13 year old domain in one way and you're buying like the authority and backlink profile that they've established over that years and not having to do the work of recreating, who knows, hundreds of articles that they may have. But there is a kind of a calculus of this build versus buy equation that comes into play. Yeah. So the biggest benefit, I think, of buying versus building is that I've built many websites in the past and two businesses can be more or less built in the exact same way or a very similar way.
13:18One will succeed and the other one will not. And it's a complete mystery as to why. And so you kind of essentially skip that process of trial and error to figure out what works and what doesn't. So that's one benefit. You're basically playing the shortcut key. I mean, this business here in particular, like it's only making 700-ish a month, but it's 13 years old. So I wouldn't be surprised if, you know, you dig into the history. It was probably once upon a time making a lot more than 700 a month for it to be that old. You know what I mean? Yeah. So that's one benefit. You know, you're shortcutting 13 years, essentially, of that.
13:53Yes. But perhaps a small price to pay for, you know, a decade plus of somebody else's effort there. The other thing, I mean, the thing that comes to mind specifically with this type of business is some kind of directory or lead gen angle for pest control companies where if I could build out that database of like, well, if you have a mouse problem in this area, you know, combine the pest plus location and then make a referral to such and such company. And there's more legwork involved with that in building relationships with the Orkin man or, you know, with the local service providers to come out and do that.
14:30But I think that would be another potential growth stream for a site like that. Very true. Very true. I will just say that directories are quite different from content sites like this one built on WordPress. But if your expertise is in directory sites, then absolutely. Like that could be your play. So it just depends on what your skills are, really. So yeah, one other thing I should point out is this is obviously not a recommendation to buy that business. No due diligence has been done. I just want to make that nice and clear. Don't go out and buy that business just because we've been looking at it.
15:01Up next, Joe pulls up a 23-year-old surf shop doing nearly five grand a month with a suspiciously low price tag. Coming up right after this. Big parenting milestone for us this month. I finally set up investing accounts for the kids. it had been on the to-do list for a while, but it was a chance to talk about the power of compound interest and making money without working for it directly. I think what was most exciting for them was the concept of owning a small piece of a ton of different businesses, and that a lot of the traffic on the road is people going to work for those companies, doing their small part to make them a little bit richer.
15:37We also offered a very generous parental match to incentivize them to continue to fund their accounts. But this brings me to my favorite financial tool, Monarch. It's the easy to use financial dashboard to track your spending, savings, investments, and more all in one place. I love the net worth tracker and especially zooming out 6, 12, 24 months and seeing how much progress we've made. I want to invite you to write your own money story with Monarch. Use code SIDEHUSTLE at Monarch.com to get your first year of Monarch core half off at just 50 bucks. That's 50 % off your first year at monarch.com with code side hustle.
16:18You know, when you're working for a company and payday just automatically happens every couple weeks, simple, reliable, easy, but now flip it. You're the boss. It's your business and you need to pay yourself and your team. That's where our partner Gusto comes in. Gusto is online payroll and benefits software built for small businesses. It's all in one remote friendly and incredibly easy to use so you can pay, hire, onboard, and support your team from anywhere. I've been on an automation kick this year so Gusto's automatic payroll tax filing is right up my alley. Plus you can set up simple direct deposits, health benefits, 401ks, you name it, Gusto makes it easy and affordable.
16:57There's no hidden fees, no surprises, and it's no wonder why half a million small businesses already trust Gusto for their payroll and HR needs. I want invites you to try Gusto today at gusto.com slash side hustle and get three months free when you run your first payroll. That's three months of free payroll at gusto.com slash side hustle. One more time, it's gusto.com slash side hustle. Do you have an e-com example or another one we should look at? Right. So this is another one that we were looking at. This one's making quite a bit more money when you look at the profit compared to the price. This is surf-store.com and it looks like they're selling water sports toys.
17:39Been around for over 20 years based in Slovenia, making close to$5 ,000 a month. Yes, that's right. So one thing that I noticed almost straight away is obviously this profit multiple is significantly less at 1.4x. So one and a half years and you'll make your money back essentially if it continues to make this amount. I typically see e-commerce stores selling for less than content stores, content sites. That's sort of starting to change. It's sort of evening out a little bit as to why it usually revolves around the style of the business. But I did look into this one a little bit ahead of the call and I could see that there's a couple of things to point out.
18:15So when you're browsing Flipper, you will see this revenue graph and it goes up to January and we're in August right now. So this hasn't been updated for a very long time, which means this graph here is probably very wrong. And so maybe the listing is several months old is the idea? The listing is probably quite old. And there's a big dip in revenue in December, January, but it's a water sports business. So that's not totally surprising, but you would want to see, well, what did 2026 year to date look like? Yes, exactly. And I would not be surprised if this particular seller doesn't respond because it's been on the market for so long.
18:52But I wouldn't be surprised also if you see the profit per month the last two months that were recorded were only$200,$400 a month. So something obviously happened around November, October, November, December in 2025. Yeah, are they holding physical inventory? Do they have a warehouse? There's more operational complexity surrounding selling physical products than just creating content on WordPress. Exactly, yes, 100%. So straight away, you've got a bunch of questions that you'd want to ask, especially if they're not listed in the description. Does it say if they're selling on Amazon or other marketplaces or only through the surfstore.com website?
19:30In most cases, it's only the surfstore. Okay. From my experience, it's very rare that you'll have, say, Amazon FBA, they call it, fulfilled by Amazon. It's not very common that you have a lot of overlap there. It does happen, but if it's built on Shopify, it probably won't. And if it doesn't specify, then it won't. Okay. Doesn't seem to in this case. So cool looking store, cool looking products, been around forever, decent historical data, at least as of 12 or eight months ago, but we'll see what the recent performance looks like. So some questions surrounding this one. And again, similar to if you've never run a content business before, I don't know, would you see people jumping right in and saying, I could be a great e-commerce entrepreneur if I only didn't have to come up with the idea and didn't have to start the business from scratch?
20:17It depends on what you're gravitating towards. I transparently have never operated a e-commerce store. However, I've brokered many of them and I know how they operate on the inside. That said, if you've had some experience selling things in the past and you'd like the concept of actually providing a product to a customer, because there is an appeal, I think, to actually providing a product of some sort. Yeah, in a way, it's easier to grasp because it's buy low, sell higher and go out and acquire customers. It's maybe simpler. Yeah. And profit margins obviously come into a play as well. So I like businesses that have high profit margins and e-commerce businesses typically have lower ones because you've got to purchase the products and potentially have to warehouse them.
21:01Although there are some businesses that are dropshipping, which is where the supplier ships directly from their warehouse to the customer. Those are a bit trickier. They're simpler, but they're trickier because they usually have a longer wait time to get those products. Yeah. And this one, shipping says international fulfillment model options for local slash EU warehouse and drop shipping. And so this is kind of the curious one. If I am looking at this and if I'm a water sports participant, like it says kite surfing, wind surfing, wing foiling, surfing, like if I am into that space. And I might look at this and be like, well, they don't have this brand or this supplier.
21:41And like immediately the bells start to go off and say, oh, I could add this supplier. I could expand geographically. It's like, well, if they're only selling to the EU, they're missing a huge section of the water sports market. Like what if we could expand and develop these relationships and maybe getting in at this price, you know, for a super established old domain, maybe that's a steal of a deal. Or maybe it's like, well, if I really want to get into it, maybe I just build that on my own. And if I'm going to have to drive paid traffic anyways, then why not just start from scratch? Cause I don't care about SEO.
22:13A hundred percent. Yeah. So you're thinking about it all the right way. And it really depends on the person listening's situation. Like, do you have another business? Do you have another side hustle that's currently going right now? And there may be some ways to potentially bolster those businesses. I like to call them bolt-ons. You get one business that's doing this thing and you bolt on this other thing and it becomes a much better business as a result of that yeah a very simple example could be say you have this website and you find a website that sells or that has a bunch of traffic from a surf store you could potentially buy that traffic essentially from the content or buy that content site and funnel a bunch of the traffic through to your store instead of amazon and generate a few sales that way or more sales that way that's just a simple example of some things that people do in order to bolster what they've currently got.
23:03Yeah, you got me thinking from a strategic acquisition standpoint of growing the email list, of expanding the body of content in one quick hit versus having to do a bunch of writing and research all on my own. Like maybe there's, and we've looked at a couple of these kind of some personal finance sites that are kind of on the downslope. They've been hit by algorithm updates or something. And it's like, oh, that would be kind of interesting. And one thing, I don't know if you do the same or recommend customers or clients do the same, was kind of plugging it in and all the information that you have about it into Claude or ChatGPT and kind of say, hey, given my situation and knowing what you know about this other business, like, what do you think?
23:46You know, just kind of starting the conversation of due diligence. It's not even due diligence. It's just like spitballing with an acquisition partner almost in the form of AI. Exactly. AI can be used to help verify a bunch of things. One of the things that we use it for, for our buy site clients, is we'll grab all of the information and put it into basically and prepare reports and things like that for the client. There are skills and stuff that you can create as well to help you do the due diligence once you've done it a few times. So I recommend like you can use AI to help bolster what you do or improve your system.
24:22It essentially gives you information, but just be really careful not to believe everything it says because it does sometimes give a bung advice. Like it'll say, no, I wouldn't recommend going for this one because of XYZ. And it reads very, it takes the numbers extremely seriously, which is a good thing because, you know, you want to verify everything, but that's just something to be aware of. The other benefit, usually, like your LLM of choice probably has a lot of information about you and probably your business as well. So using it to help you come up with potential ways or opportunities, fits that you haven't thought of with your current business would be something that you could also use it to help you with.
25:00Yeah, and I found it kind of tempered my enthusiasm a little bit. It was like, hey, here's a reality check. The thousand articles that you think you're acquiring, well, most of them don't meet your quality standards for these reasons. Only five of them are actually getting any kind of traffic. So you're paying for a lot of stuff that's probably never going to see the light of day. You know, it just kind of went through some of these reasons. There is no email database. It's like, oh, OK, maybe this is not what I thought it was going to be. So there is something like that. I was going to ask on this Surf-Store listing, asking price$83 ,000 is a pretty serious chunk of change.
25:39So there's some risk involved. But do you see people asking for seller financing or trying to get other creative financing deals done on these? Yeah, so there are a few options there. Typically, you start seeing seller financing start to be more of a talked about topic. I would say$50 ,000 plus. Just to explain seller financing for someone who's never heard of it before, It's basically just where you agree to purchase the business based on a set price. So let's just say 80K for this business. But you don't pay it all up front. You pay a percentage of it up front. So let's just say for easy math, 50 % up front.
Read the full transcript
26:14So you're paying 40K up front. When you've basically transferred that initial 40K to the seller, the business is now yours. But you have a seller financing period where you're essentially paying back the rest of the 40k that you agree the business was worth and that can take as low as three months all the way up to two years i would say uh usually doesn't go much past i as as a seller i don't like it going more than 12 months yeah if i'm the seller thinking i'm gonna get my 80 grand in cash all of a sudden well now i gotta wait two years for the last 50 percent sure exactly the setup is more difficult the terms are more difficult you have to have things in security so if the payment isn't made, if the buy defaults on the payment, then there's some recourse that has to happen.
27:01So it really depends on those sorts of factors, which makes it quite complicated. And I wouldn't necessarily recommend it, especially for a first buy. And this is where having a broker in your corner can help you guide you through these more complex scenarios where we know we've done so many of these, we know exactly what to do. Are there other sources of financing that are interesting to you. The example that comes to mind completely offline was Anthony in his vending machine business. He's like, well, I can finance the machine for, call it$500 a month. And I know it's going to sell a thousand bucks a month worth of stuff.
27:35So like my debt service is covered. My employee to go stock the machine is covered. And after whatever it is, 12 months, like everything is gravy. Like essentially bought a cash flowing asset for free. It was like this cool, like kind of a little life hack. It sounded like almost, and I don't know if there's anything similar here, where I can buy this cash flow for low out-of-pocket and kind of pay for it with the proceeds from the business? Yes and no. It is possible. It's definitely been done, but it usually involves some level of partnership and you've got to build quite a bit of rapport with the person.
28:07So if you're dealing with, say, a friend, so a friend comes to you online, I'm looking to sell this business and I think you might be interested. That's kind of a different scenario and you might entertain something like that with them. For most of the businesses that you would find on here, that's just going to say, you'll get a no. But then again, there's no harm in asking. And I think that if the terms make sense, you know, you would probably have to ask, you would probably have to agree to above asking price for something like that, for them to get to agree to the terms that you're asking for.
28:37So some buyers have got this ethos that they don't care how much I pay for the business, so long as the terms make sense. Sure. Yeah. So you can, and usually it's involved in some sort of profit share. It's more common with bigger deals, like sort of mid six figures and up, I would say, where that sort of starts becoming more reality because sharing 50 % of 700 a month is not really all that meaningful. Whereas if you're sharing 50 % of 50K a month, then that's a very different sort of scenario. Got it. Yeah, I'm on Flippa. There's a ton of different categories. There's e-com, there's websites, there's apps, there's software businesses.
29:16I don't know if you have any experience in those marketplaces, FBA businesses, YouTube channels. There's quite a bit going on here. Do you play in any of these lesser known categories? Absolutely. We've probably listed every type of online business there is throughout brokerage. I haven't operated many of them myself. So a bit of my background, I started buying and selling businesses back in 2012, and I pivoted to be a broker in about 2018. So since then, there has been a slow transition, and now I actually don't run any businesses myself personally anymore. I help broker. I help buy and sell businesses for my clients.
29:50So my expertise is more around actually the process of buying and process of selling them. What other mistakes do you see buyers making? Like it's easy to kind of come on and kick the tires and say, oh, that looks interesting. But I mean, there's still, we're still talking about a lot of money changing hands here. Joe's response in just a moment, plus the SaaS listing that's really just a clever wrapper on ChatGPT, facelists, YouTube channels, and the$4 million deal that had a single point of failure. Coming up right after this. Big parenting milestone for us this month. I finally set up investing accounts for the kids.
30:30It had been on the to-do list for a while, but it was a chance to talk about the power of compound interest and making money without working for it directly. I think what was most exciting for them was the concept of owning a small piece of a ton of different businesses and that a lot of the traffic on the road is people going to work for those companies doing their small part to make them a little bit richer. We also offered a very generous parental match to incentivize them to continue to fund their accounts. But this brings me to my favorite financial tool, Monarch. It's the easy to use financial dashboard to track your spending, savings, investments, and more all in one place.
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32:26That's three months of free payroll at gusto.com slash side hustle. One more time, it's gusto.com slash side hustle. Yeah. So one thing I would recommend that buyers do is get to know the seller a little bit, especially on your first deal. So get on a call, get on a video call and just talk to them how they started it. Try and build some rapport. Rapport is, in my opinion, underrated for most online business deals that we do. I've done hundreds of deals where the buyer and the seller have never even done a video call together. It does happen. And it happens often. You can do that. But it creates kind of gaps between them that if something goes wrong, the deal could potentially fall into those gaps.
33:08And so having that rapport to, okay, is this person like a trustworthy person? Can I talk to them? Are they not strange and weird or trying to hide things when we're on a live call? They're online entrepreneurs. Of course, there's going to be a little bit weird. they were attracted to this online business thing this non-traditional life there's going to be something there for sure no but i mean you know the difference you know the difference and usually talking to most people are fine but you you will probably tell and if your alarm bells are ringing when you're just talking to them it's like okay maybe this deal's not for me even if it does line up in other areas so that's one thing but a more practical thing i think for buyers in particular is not having clear roadmap after you've bought the business so the biggest mistake by far that we see buyers do they will purchase the business and then they'll do nothing or if they have a plan they don't action they just do nothing i actually sold a business a number of years ago for a very nice multiple i think it was like nearly four or five x and for some reason the seller just they didn't even change the monetization to their own it was still running online a year later so i was still making money on this business it totally blew my mind there are people out there they just don't take it seriously.
34:21They buy the business and they let it fall to the website. Yeah. Not switching it to your Amazon ID or whatever. Okay. So make sure that you've got a plan after the fact on what you're going to do. I'm looking at this one. It's a SaaS business called Assignment GPT. The tagline is we help you with your homework doing around$2 ,000 a month, asking only$20 ,000 slashed from 40 ,000. Because if you look at the revenue in page view chart, It seems to be in a downward trend, yet the description says it's a thriving, fully automated SaaS platform. Yes, that's another good point, Nick, because every seller, obviously, it's in their best interest to shine the best possible light on their businesses they can to make it sound good.
35:04We do it as well on the sell side. It's important to make it sound like it's a good business. We take the tact, though, that if we find some skeletons, we are going to mention it. So just be aware. If you come to us with a business to sell and there's something wrong with it, we're going to point it out to the suppliers so that they know what they're getting. But then we value it appropriately also. Everybody's attracted to software businesses. These are some of the most profitable businesses in the world, right? And the question is always, well, the customers, are they on recurring? This is a software as a service.
35:35And it says like the churn is really low, only 2%. But how are you acquiring new customers, right? Could you essentially fill the pipeline and give yourself a raise every month in a recurring revenue SaaS business. And in an AI space where disruption is weekly, how are you going to stay competitive with everything else that's out there and some of the alternatives here? So it's kind of an interesting one. For this one, I wouldn't buy it unless you have an AI background and you're very good with AI because this is obviously an AI-operated business. It's basically using AI as the service, essentially.
36:13Yeah, your costs here are your OpenAI, 17 bucks a month in API costs, basically. It's like, oh, okay. Created a clever layer on ChatGPT. Precisely, yep. And the other thing, actually, with SaaS businesses, you would probably want to avoid is lifetime sales. So we see some SaaS businesses, we've sold a couple actually even, where they have sold lifetime sales to their clients. For a buyer, that's the worst case scenario. Now I got to support these people for life. Exactly. You've got to maintain them. They are lifetime subscribers or lifetime users of your product, and you don't even get paid a cent from them.
36:50So just be aware of that, especially if you're building one, don't do lifetime unless it's like really early and it's not a plan moving forward. What do you think about buying a faceless YouTube channel? This has been kind of an up and coming asset in the past couple of years, it seems like. Yeah, it's because they're easier than ever to create them now you can have ai create the video and the voice you don't really have to do anything you just have to be able to prompt really well so they're very popular now and there are some that are really good in fact we've got one for sale right now that's in the anime niche i think that they're very interesting one of the more trickier parts to them one of the things i mentioned earlier is you want to have diversification a faceless youtube channel is not super diversified You're very reliant on YouTube.
37:36If YouTube changes the rules, that's your source of traffic or your source of revenue basically gone. Which they seem to do constantly as it relates to these businesses specifically. Because it's like the cost or the barrier to create this stuff has gone down, like their servers are just getting flooded with this stuff, which is a real cost to them. And they're like, well, okay, we're going to change the monetization rules, the incentives surrounding this type of business. It would come down to, okay, are you actually supplying some form of real value? And does it really matter that it's faceless?
38:06Those are the key things. But I mean, one of the biggest things, or one of the best things you can buy is uniqueness. So if your business is unique, diversified, it's high quality, and it's basically in a business model that you're familiar with, those are the sort of things that you typically want to look for. And they sell for more. Because if they're unique, they're difficult to copy, they're more valuable in almost every situation. Yeah, definitely. Aside from Flippa, are there any other marketplaces you think are worthwhile for people to shop around at? So I'd say the one that's very close behind.
38:36There's two that I would consider basically in the same realms as Flippa. Empireflippers.com. They are actually a brokerage, so they've fully vetted everything that goes on their platform, and they're quite selective about what they list there. But their hoops to getting in and involved on their platform is a little bit more involved. Then there's acquire.com. That one's also quite good, but you have to pay to be a member in order to get access to the information there. I don't think it's very much per month, but it is something to consider. And then there's other freer ones like investors.club, Motion Invest, Niche Investor, Money Nomad.
39:12I think is Empire Flip is a smaller version for smaller businesses. So that might be a place to start for some people also. There's a bunch of others as well, including my own. right and it feels like the higher the price point the more established the business is going to be and it's maybe in my mind i want to equate higher price with more legitimacy and even though it's more money like it feels less risky the business is better established and hopefully has more legs to stand on like it's not reliant on one algorithm change or one ad sense update and i'm out of luck Yeah, exactly. So we actually had one LOI on a business for four mil.
39:51It was by far the biggest deal that we'd ever been a part of. And during the LOI process, because this business was making loads and loads of money, it was like ridiculous the amount of profits it was making. It had basically one source of traffic and Google decided, nope, not today. And that can happen. More money does not necessarily mean that the business is secure. It means you want to look for things like diversity, uniqueness? How easily can I replicate this business? Those are the sort of questions you want to be asking more than the others if you want the business to continue moving forward.
40:25Right. What's the moat here? And this is what you can ask even AI for. Do a SWOT analysis. What are the strengths, weaknesses, opportunities, and threats in this business? What's going to make this deal go south and see what it comes back with? Exactly. Yes. Ironically, that's actually, we have a SWOT section on all of our listing descriptions. We find it very important to highlight all of it, including the bad stuff. How have you seen this shift over the last few years? I have to imagine maybe 2021, like peak of the market, everybody wanted to get in, maybe some algorithm updates or some AI influence.
40:55And now content sites are not worth what they once were. I don't know what's been your pulse on the marketplace here. Oh my gosh. So there's obviously been loads and loads of ebbs and flows. Back when I started buying and selling businesses, It was very easy to buy a content business for maybe 1x, a bit less than 1x. Wow. So multiples have gone way up compared to what they used to be. That's because the market was basically flooded by more traditional investors that are used to spending a lot more for businesses. And so they see these businesses being sold for peanuts and they go, oh, we can do that.
41:30Oh, okay. Okay. Okay, so if I'm an institutional investor, I'm used to buying the S &P at an 18 to 20 price earnings ratio. And all of a sudden I look at this website where I can buy it at a one to two PE. It's like, oh, okay, I'll do that all day long and I'll build a portfolio. Exactly. So that's actually a really good way to diversify. And it's what I did. I bought multiple businesses. I didn't just buy one. I had lots of them. They were all doing sort of similar things. But having more businesses that are doing similar things is a way to diversify. So there are probably lots of people out there that do this exact same thing.
42:03You buy 10 businesses, maybe five or six of them don't work out, but the other ones do really well. So it becomes a numbers game in that instance. Yeah, it's similar to real estate, where if I have one house and one vacancy, I have a crappy month. But if I have 30 houses and one vacancy, I can weather that storm. Exactly. Precisely that. Well, Joe, this has been super interesting. You've got me thinking about the strategic acquisition side again, something that kind of put on the back burner a little bit. But what's next for you? What's got you excited these days? I think like most people, AI has made a lot of changes in the industry and also in our business.
42:39We're now finding we can do things that we were never able to do in the past. For example, I'm beginning to relaunch my website by myself without a developer. I never would have tried to do that in the past because AI is so much more advanced now than it used to be. I've built internal tools for our staff to use. Lots of things that we use thanks to AI. So to me, that's what's keeping this business really interesting for me. What can I do next with AI, essentially? And how is AI potentially going to improve these businesses moving forward? What are buyers and sellers doing and using AI for to improve what's already been done?
43:13And we're seeing lots of different things there. And it's very exciting. And we're just getting and stop it. It's weird because the market for a traditional content business, even on a, on a, just a browser side, you know, I type in a question and the AI snippet answers it. It's like the zero click world, right? And so these content sites, they still exist. They still do get traffic, site installation included, but it's not what it once was. And so it's kind of just this downward expectation and maybe this long, slow decline of it. But I don't know. Do you still see buyer interest on getting into this space now that maybe expectations are adjusted to a new reality?
43:56Absolutely. Yeah, definitely they are. It's both a blessing and a curse. One of the biggest updates that ever happened was in 2023, where all small content sites, which was the bulk of my clients, basically just got erased. And that was because of basically this ai snippet that you talked about so the traditional content site where you've got articles that say how to mow your lawn how to you know clean your underwear all of those sort of informational type businesses are basically dead in the water now you can't have those sort of niche businesses anymore in that in that format and get traffic there are other ways that you can get traffic but it's usually not that way what's working instead if you have a sense of how these sites are kind of continuing to survive?
44:42So we saw some things starting to emerge. YouTube channels that we mentioned earlier is one that we saw a rise in. And in terms of traffic, we still sell these sort of small content sites, but they're getting traffic from other areas, things like Pinterest or social media, or they're using virality in order to get traffic. Whereas that existed before, but not quite in the same way. And they've sort of formulated strategies that really work around the specific niches that they're in. Okay. Yeah. So as you're shopping, you don't want to put yourself in a position of catching a falling knife and paying tens of thousands of dollars for the privilege of doing it, but looking for something with some diversity of traffic sources and hopefully systems in place to continue those after you take over the keys of that.
45:27So Joe, really appreciate you stopping by, giving us an inside look at what's going on in the world of online business acquisitions. Just website brokerage.com is where you can find him. Just website, brokerage.com slash 2026 is where you'll be able to download the state of online business sales report that you put together to kind of get that up to the minute look at what is going on in the world of buying and selling. And Joe, let's wrap this thing up with your number one tip for Side Hustle Nation. The thing that I attribute 90 % of my success to is consistently showing up, doing the same thing constantly over and over and over again and just showing up and doing the work, even when things are a little bit tough.
46:11When I started, it was part of a cohort of people. And out of that cohort, I would say only maybe 10 % of those people actually went on to do something with it. My point is, once you make your mind on something, keep going at it until it's proven to not work. Consistency and just showing up day after day is what has led to my success. Yeah, absolutely. What's the John Lee Dumas line? Focus, follow one course until success. I think there's a lot of truth to that. Consistently showing up and doing the thing. Joe, appreciate you stopping by. A couple of takeaways from me. Number one is this due diligence phase.
46:49Make sure if you go into any acquisition, make sure it's a fit for your interests, your expertise, your curiosity, your goals, right? Like start with the end in mind. What's your cashflow goal out of this? Have a plan in place. Joe said, look, that's a big mistake. What's my transition plan? What's my growth plan to take this thing over and hopefully earn back my investment even faster? And then kind of what we talked about is maybe don't let this be your first thing. Kind of build first, learn the game a little bit, get some reps, get some practice in on your own for free or for very inexpensive before you plunk down.
47:23And it's a reason why kids play t-ball before they go to the majors, right? Like there's a progression, there's a step up before you do this stuff. So don't forget to grab your free listener bonus for this week. It's my free AI assisted side hustle brainstorming worksheet to get you some realistic side hustles personally tailored to you. I think when you fill in the sheet and you feed that into your AI of choice, you're going to get much better suggestions than just Googling for side hustle ideas and they're going to be personalized tailored to you. Just hit the show notes link in the episode description and test it out for yourself.
47:57We've gotten some fun feedback on it so far and curious to hear what it comes up with for you. Big thanks to Joe for sharing his insight. Thanks to our sponsors for helping make this content free for everyone. You can hit up sidehustlenation.com slash deals for all the latest offers from our sponsors in one place. Thank you for supporting the advertisers that support the show. That is it for me. Thank you so much for tuning in. Until next time, let's go out there and make something happen. And I'll catch you in the next edition of the Side Hustle Show. Hustle on.
From the publisher
What if you could skip the hardest part of starting a business, the zero-to-one grind, and just buy your way into cash flow instead?
Joe Burrell runs Just Website Brokerage, where he's helped broker over 300 sales totaling more than $7 million in lifetime value.
He started buying and selling his own online businesses back in 2012 and pivoted to full-time brokering around 2018.
These days he doesn't run any businesses of his own — his expertise is entirely in guiding buyers and sellers through the deal process.
In this episode, Joe walks through real, live listings on Flippa, breaking down what the numbers mean, what red flags to watch for, and what actually makes a website or online business worth buying.
(Download Joe's State of Online Business Sales report at justwebsitebrokerage.com/2026!)
Tune in to Episode 761 of the Side Hustle Show to learn:
how to read a business listing's profit multiple and decide if the asking price is fair
the questions to ask before buying a content site, e-commerce store, or SaaS product
why diversification and a post-purchase plan matter more than the price tag
Full Show Notes: Shopping for Cash Flow: Buying an Online Business in 2026
New to the Show? Get your personalized money-making playlist here!
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About The Side Hustle Show
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