How to Buy Online Businesses in 2025 – Digital Investor Show interview
Updated on August 29, 2025
Transcript
Hello and welcome to another episode of the Opportunity Podcast. I'm your host, Greg Elfring, head of marketing over here at Empire Flippers.
Today’s episode, like the last one—or maybe it’s one coming up, who knows—is a bit of a unique take. We usually don’t do this, but I want to start doing it more because I feel it’ll be really, really valuable to you as a listener. So, in this episode, I’m not actually interviewing anyone—I’m the one being interviewed by a friend of the company, Matt Reed, at Matt and Liz.
Matt and Liz have a background in M&A, private equity, all that kind of stuff in Australia. Now, they’ve been spending a lot of time teaching people about buying micro sites and micro businesses, growing them, and flipping them. He's also recently been talking a lot about buying and selling agencies, too. He invited me onto his podcast to discuss all things M&A, and I thought it was a great conversation. I figured, why let it sit there when I can promote him a bit, but also share the conversation with you guys because it was a fun discussion.
With that said, I hope you enjoy the conversation between me and Matt, and I'll see you on the other side.
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Matt: Today we are talking about buying and selling online businesses in 2025 and, in particular, where the opportunities are. As we all know, in 2025 the online space has changed dramatically thanks to Google updates, but of course, the big one is AI. The impact of AI, particularly on the sorts of sites we have been buying and selling for the last decade, makes it a very interesting space.
There are challenges out there, and we're going to look at those today. But in particular, we also want to look at where some really good opportunities lie. Like everything in tech, this is a constantly moving—and now, thanks to AI, a very fast-moving—space. We’re excited about it, but we do want to address the challenges.
So I was thinking today, who should we speak to? I’ve got the perfect person for us on the Digital Investors Podcast. His name is Greg Elfrink. He is the content manager—well, actually, the head of marketing—at Empire Flippers. Greg has deep experience not only in content marketing but also in our favorite topic, SEO. Thank you, Greg. But also, Greg is very passionate about buying and selling online businesses, all styles. The great thing about talking to someone like Greg is he’s across all the deals on the Empire Flippers platform, plus he has friends and lots of associates who are doing six and seven-figure online business deals. So Greg is a great person to get first-hand experience and the real stats of what is happening out there because he’s at the pointy end of the stick when it comes to online business sales.
Greg, thanks so much for coming along today on the Digital Investors Podcast.
Greg: Yeah, thanks for having me, man. I started off as content manager, but now I’m the head of marketing. But you and I have just said the word “content” so much offline, so I forgive you.
Matt: Yeah, sorry. You’re the head of marketing. But basically you and Andy are running Empire Flippers and driving the business. So you see a lot of deals. You’re very hands-on, I take it, at Empire Flippers across all the deals?
Greg: Yeah, yeah. So it’s Andy, me, and two other managers who are primarily running the business these days. I see a lot. Andy is more in the weeds than me, obviously, because he’s in on the actual deals. But I’ve done consulting, I’ve helped a lot of my friends exit. We’ve created, I think the number is 89 millionaires at the moment of exit. In my view, we’ve created well over a hundred millionaires because we don’t count the 900k exits—which there have been a lot of. I was employee number four at EF.
When I first joined the company, I remember talking to our co-founders. We had this deal; I think I was in the company for like two months. The deal was $150,000, and one of our co-founders at the time, Joe, was like, “Oh Greg, everything changes at 150k. Like, it’s a way different deal.” And then earlier this year, Andy and our team helped sell a $13.5 million e-commerce store. So times have changed.
Matt: Wow, what a difference, Greg. This is really cool. Also, to put it in context for our listeners, Greg, it’s particularly relevant to our community. Share your background real quick. Like, where did you start? Here you are now, an online business legend. Greg speaks at conferences all around the world; you’re constantly traveling and talking about online businesses, content marketing, SEO, and stuff. But where did you start, and where are you from?
Greg: Yeah, yeah. So I started, like many internet marketers, as an oil field roughneck in Alaska. I’m from Alaska—Alaska born and raised. I worked in the oil field for about eight years, on rigs, six miles off the north coast of Alaska—so even colder than what people normally think.
I have a lot of funny stories—like, I saved my welder from a polar bear attack, I fought a rabid fox with a squeegee… you know, things you do in the tundra. But I hated it. So I taught myself internet marketing. I failed at a lot of different things—from agencies, to affiliate sites, you name it. Toward the end, I had given up on any optimism and just had this gritty cynicism to everything, but I thought, “I don’t care how long it takes, I am going to figure this out.”
I started doing freelance writing because I’m a very fast writer. I write novels and poetry for fun. And I knew one thing for certain: all the SEOs at the time absolutely hated writing content. So I undercut everyone. I charged half a cent a word— even the guys in India and the Philippines couldn’t keep up with me, doing this in the evenings.
Matt: On the oil rig and stuff where you…
Greg: That’s right, yeah. Literally moonlighting. I would work my 12-hour shift from midnight to noon, then I would go up into the TV room in the camp—there was this one corner of the room where you could see frost bleeding through the building, and I had a decent Wi-Fi connection. So I would write for my clients for an hour or two after my 12- or 13-hour shift. One of my clients, I wrote so much plumbing in Ohio and roofing in Perth articles for him. He found out I was just freelancing and said, “I would be burnt out if I were you.” Like, dude, I’ve been burnt out for years, but you still gotta pay your bills, you know what I mean?
Fast forward: I saw Empire Flippers put out the content manager’s job and I thought, “Well, here’s another job I’m never going to get, I might as well apply.” I personally love marketing and have loved it since high school—I find it the most applied form of art. The issue I always had is I had no college education, so no one would look at me. I was just an oil field roughneck, right? And I purposely did not go to college because, at least in America, I view most of those degrees as a culturally acceptable scam. But with HR software, you don’t have that tick, so they just auto-reject you.
But EF hired me. I moved out to Vietnam for training, and now I do the whole digital nomad thing. Helped the company become close to a nine-figure company, starting at very low six figures. I’ve helped sell over 2,400 businesses at this point—from small entrepreneurs to private equity family offices. We kind of created the FBA aggregator boom; I always call them our stepchildren because whenever they raised money, how they’d get their first few deals was registering an Empire Flippers account.
Matt: Yeah, right. You guys did a lot in that space. So you’ve worked with a lot of big buyers with big budgets for online businesses?
Greg: All across the board. Whether it’s someone looking to do a side hustle, maybe they’re still working a 9-to-5 and want to buy more of a side business, all the way up to family offices, private equity, strategics. We sold a business—not sure if it was the $13M deal; might have been another one—but we sold it to an international conglomerate. So, very diverse experience across multiple different buyer and seller types. Probably more than almost any other broker—I don’t know anyone who has as much as us.
Matt: All right. So, you’ve seen a lot then, like all of us have, but you are seeing all these deals right now as we record—seeing the impacts of AI and the Google algorithm updates. What I’m interested in: let’s start out—
Although, I will just mention—it just hit me there—here you are, an Alaska oil rig worker, and you’re known for writing about roofing in Perth.
Greg: I wouldn’t say I’m known for it—I never got credit for those articles in terms of author names, you know.
Matt: You became an expert in roofing in Perth, Australia! Before we move on, I think this’ll be a funny story for you and your audience. So, once I got into Empire Flippers, you know probably as well as me, most niche site owners are very secretive about their sites—especially with other SEOs, right?
Greg: But since I work at EF, I know all the secrets because you gotta tell me if you’re going to sell. So once I started becoming a bit more known in the SEO/affiliate crowd, a few friends who are very famous SEOs started asking me, “Could I sell this type of site on EF?” And I’d be like, “Is it thissite.com?” They’d say, “How do you know that?” “Well, I wrote all the content for it, because you hired a content agency that farmed it out to me.” So I ended up selling a lot of the businesses that I, funny enough, wrote the content for when I was on the oil rig.
Matt: Well, that’s really cool. Now I think this really puts it in context for our listeners—why you’re such a great person to talk to and pick your brain about what’s happening in the marketplace now. So, what are some of the opportunities? In a nutshell, with sales, what have you seen for the difference between, say, this year (as we record this—2025) and the last couple of years, which have been an absolute boom time for all of us online, no matter what we were doing? How are things shaping up so far with the new changes we’re seeing out there?
Greg: Like I mentioned to you, I think the industry—at least the affiliate site industry—is wounded, but that doesn’t mean it’s over. There are still opportunities here.
A few years ago, like 2020 to early 2023, it was an absolutely insane time to be a digital entrepreneur. We were selling a million-dollar business a week. It was wild. You couldn’t go wrong—everything looked so easy. But easy times always lead to hard times, and hard times shake out the people who got too used to the easy times.
If you look at multiples right now, yeah, they’re worse than they were in 2022 and early 2023, but they’re also better than 2019 and earlier. That’s the thing people always forget. I have a lot of seller friends who are like, “Oh, I’m going to wait till another 2020 thing happens.” But you’re going to wait for three different global black swan events to all happen in perfect unison? This is unlikely to ever happen again in your entire life—or a couple of lifetimes—where all those events work perfectly together.
If you look at multiples in 2025, like, we’re still selling affiliate sites on average for between 25x to 29x. If it’s a high-quality one, like 30x to 34x. In 2019, we were selling a lot of them for less than 20x; before 2019, some were at 16–18x. I still think it’s a great time to sell. It’s harder—much harder than 2020–2023. But when I say harder, I also just mean normal, because 2020–2023 was abnormal.
Matt: Abnormal. Okay, so for us buyers, good news?
Greg: Yeah, yeah. This is a great time for buyers. For people who know what they’re doing, this is a fantastic time to be looking at buying online businesses of any kind, but especially affiliate sites.
Matt: What’s changed for buyers? Are things more negotiable? I know you’re saying the multiples are the same—and obviously you’re from Empire Flippers, you want to talk that up—but come on, Greg, I want to buy. Are things a lot more negotiable now?
Greg: Absolutely. We’re super buyer-friendly. Our philosophy is we want both the buyer and the seller to win in a deal. And if they do, then we win via repeat customers. For a good broker, it’s not the seller—it’s the buyer. And often sellers become buyers because they’ve got capital. We want everyone to win in a reasonable way that everyone is happy. Unlike some people who jack up the price to try to pressure the buyer into a bad deal—which I can share some horror stories about.
But in general, from 2020–2023, because there was that absolute feeding frenzy, it was really difficult to negotiate anything. Even private equity people—for the first time, as far as I’m aware—were buying businesses worth less than a million dollars, which are usually too small for them. Even they were getting pushed out, it was so competitive.
Right now, ironically, a lot of those private equity people are dead in the water because they had no business buying businesses at those multiples, nor running them. They just did not operate them.
This is a really good time for buyers because 2024 was a worse year for both buyers and sellers than 2025, regardless of the business model. In 2024, a lot of the buyers (not the crazy private equity people) were like, “I can’t get a good deal,” because sellers still had unrealistic expectations. But now, sellers are waking up to reality, which I always joke about: for sellers, my job is to help break your dream so I can help you wake up and become actually rich. “My business is worth $3M!” No, it's worth $1.5M, but I’ll still make you a millionaire.
So now is a really good time. Sellers know that buyers in general are more hesitant. They want to—you really need to justify it to them. They’re also way more flexible on things like seller finance, earnouts, even full-on price.
Matt: So, this is all very good news for buyers—less competition in the market, less dumb competition. By dumb, I mean people who raised, like, $100 million. I had a guy in 2021 make fun of me for no college education—he went to Wharton—and he put in an offer on a deal, but I told him he hadn’t even done due diligence. He said, “Yeah, but Thrasio is putting an offer on it, so good enough for them, good enough for me.” I was like, “Didn’t you go to Wharton?” So, I knew that wouldn’t end well.
But yeah, now is a very good time from a buyer perspective to get in on some businesses.
Matt: One of the things I’m really interested in with Empire Flippers that’s always impressed me is just how flexible you are. I come from an M&A background; I used to do bricks-and-mortar businesses in the multimillion-dollar range. It was tricky—brokers didn’t like facilitating vendor financing or creative deals. But you guys seem to be very flexible. Is that an easy thing for me as a buyer, if I come and buy a website through you guys and want some kind of creative structure, is that normal?
Greg: We’ve always seen plenty of such deals. Anything above $500,000 usually has some kind of seller finance or earnout, even sometimes above $200K. Anything under $200K is typically bought with an all-cash offer. So yeah, we’re very open to seller finance, earnouts, and similar deals. Our team manages all of that—unless the seller and buyer ask us not to—because we only get paid our full commission once everything is done, so our incentives are aligned. We’d never recommend a deal we don’t expect to get paid out on.
A lot of brokers don’t like creative deals because most are, at their core, similar to real estate agents—they want their commission. They rarely understand investing; they’re usually just good at selling. But we see value in leveraging all these different tools and have even done vendor financing and revenue-based finance. In fact, we sold one business recently where the buyer did no money out of pocket using RBF plus seller financing.
Some buyers, though, may not be sophisticated enough to use these structures effectively—they’re using someone else’s advice but don’t fully understand the risks. For us, it’s a buyer risk, not a broker or seller risk—the seller still gets paid, the broker gets their commission. So, it’s no problem on our end.
Matt: That’s great. So, if you’re listening and looking to buy, you can negotiate with Empire Flippers, and earnouts are possible. It’s a really nice way to buy. Like you said, both parties have to be reasonably happy. My mentor in bricks-and-mortar M&A always taught me that.
It’s also something to remember for our listeners: as a beginner, realize that as a buyer, you’re building a relationship; people often become repeat buyers. It’s a long-term relationship game.
Greg: Absolutely. There’s no reason both parties shouldn’t be happy. Inexperienced buyers and sellers come at negotiations with the wrong angle, like some cowboy showdown, when it should be a collaboration. You as the buyer should want the seller to get a payday; the seller should want the buyer to buy their “baby” at a fair price.
Often buyers and sellers keep working together, even on other projects. We’ve had deals where the seller and buyer later came back as business partners. Why ruin a great connection?
Matt: Agreed. We’ve bought several websites from the same seller over the years—it’s a relationship based on trust and understanding. So it’s all about relationships and playing the long game.
Greg: Absolutely. The buyers are the most frequent customers. Sellers might sell once every few years; buyers might buy several businesses a year. We had a guy buy 15 businesses from us in a single year.
The myth is you make all your money when you sell; that’s true, but you can make more money by buying, because then you can sell way quicker. If you buy a business, you already have its track record, so you don’t need to wait to build that up yourself.
Matt: That’s a good point. I think that will be interesting for our community—especially for beginners and intermediate buyers. It’s a long-term game and about relationship-building. The buyers are the ones making the money by buying multiple businesses.
So, let’s look at the challenges, particularly with affiliate sites and adsens/broker sites. Let’s start first with bigger ones—what’s working now in 2025? What advice do you have for people who want to get into that space?
Greg: If you were going to get into content sites, I told you offline—I’m a lot more leery of starting one from scratch these days because Google is so random. But buying one still has a lot of different opportunities.
Businesses valued above $500K in the content space typically have true brand elements or strong brand value, which makes it easier to rank. They’re often monetized through affiliate and display ads. But for me, the game of digital business is: how do I diversify and hedge my bets so I’m not so reliant on a single tech giant? For SEO, it’s Google; for e-commerce, it might be Facebook, Amazon, etc.
So, when you’re looking at these $500K–$1M content businesses, the serious traffic they pull is a serious opportunity to upgrade the business. For instance, we had a seller list a site with us—about $1.1 or $1.2M. Traditional display ad site, almost no affiliate. Maybe 2–4% of revenue came from a course he had on Udemy. If you know about selling courses, Udemy is a terrible place—you have no control over your product, and they’ll discount it massively without telling you.
This buyer saw the huge traffic, took the course off Udemy and put it on his own platform, directed all that traffic to his own course, and increased the price from $9 or whatever Udemy was charging to $97. The total addressable market was huge—it was a B2B course in a common software.
I don’t know what he ended up doing with it specifically, because he bought it four months ago, but that was the opportunity: take something sitting at the margin in the business and massively multiply its revenue simply by controlling the funnel.
So, for me, the real game with affiliate and display sites is: how do I take this business and grow the margins? You can still do display and affiliate, but I always recommend thinking, “How can I control the funnel with my own products and services?” That allows you to be less reliant on SEO, because now you have margins to work with paid ads or other channels.
Matt: This is gold, and it’s exactly what we teach. We love information products—we’ve been doing that for a decade. And I’ve always said, everything old is new again. Email lists are hugely valuable; now even more so, in the AI age.
If you’re buying a site, make sure you can add a community or an email list, and maybe convert it to selling info products if the niche suits.
Can you share your strategy around affiliate sites—converting them to other monetization? I’m not a big fan of e-commerce, but can you talk about why that can be a smart move?
Greg: Before I dive into that, I want to share the email list story because it’s important. One of the big critical points of failure with affiliate sites is SEO. Everyone knows AI is coming for everything. I met a speaker at Affiliate World Bangkok who said he always gets the email first, then does the affiliate stuff. He had a Buzzfeed/ViralNova-style site back when that was hot for organic Facebook, but when that stopped working, everyone else in the niche crashed. But he’d built an email list of over 1 million, so he could send out affiliate offers every week. He hasn’t worked in six years.
That’s what I mean. You need to find ways to control as much as possible—affiliate, e-commerce, digital products, owning the customer data.
On e-commerce—Kevin Espiritu is a friend of mine; he started epicgardening.com as a basic Amazon affiliate site, a typical “bog standard” niche site. Over time, he focused on building community and a real brand. He became an e-commerce store selling specific gardening products, so much so that now he’s one of America’s largest online gardening retailers.
When all the AI doom happened for affiliate sites, I checked in with him. Even though he had tons of SEO, he’d diversified—now SEO is less than 20% of his traffic. Most of his traffic is organic from other channels—YouTube, Instagram, podcasts—because he treats the website as a magazine: entertainment and education, then funneling to the store. He can also run ads, because his margins are thick enough.
The crucial step: he built an email list, fostered community, and when he wanted to develop a product, he simply emailed his list, “What would you buy from me?” They told him, he created pre-orders, used the pre-order money to buy inventory, and every launch still sells out.
Matt: That’s brilliant. So, for our newer listeners, is there a “snipering” opportunity to find good but cheap affiliate sites not currently leveraging lists? Buy them, build the list, and re-monetize?
Greg: 100%. We’ve sold entire “newsletter” businesses with barely a site at all, just audiences. Most affiliate site owners are still brochure websites—someone comes, picks up a brochure, throws it away; they don’t subscribe to anything. You want to convert to a magazine/brand approach. Newsletters are key.
If you don’t want to buy, reach out to affiliate site owners and pay them per email subscriber—they’ll think you’re crazy, but you play the long game. If you know you’ll make $50 per subscriber in the first month, offer to pay $5 per referral. That can scale very fast.
Matt: And what about the direct transition to e-commerce? I know you’re a big fan. Not my thing, but there’s a lot of opportunity there, right?
Greg: Absolutely. I always tell people, buy a business where you can do all the monetization models. Back to Kevin at Epic Gardening: he focused on community, built the list, asked what products people wanted, launched one SKU at a time using pre-orders—so he massively de-risked the cash flow. Sold out every batch. Plus, he diversified his traffic channels.
So, moving an affiliate site to e-commerce works if you’re focused on building a brand, a list, and testing products with your audience. It’s how you avoid being beholden to one tech giant.
Matt: That’s huge. For our listeners—even if you want to start small, you can look for these kinds of “transition” opportunities.
Switching gears, I want to ask about entry-level sites—sub-$50K, maybe even smaller. Are there still opportunities here? Are they selling?
Greg: Little-known fact: EF still sells businesses at the 50k price—sometimes in days, even hours. They move quickly, so people don’t realize we have them. The market is softer now, maybe a week instead of hours, but as long as it’s a quality site, it’ll sell.
A lot of your audience are hitting goals with micro sites—making $1,000, $2,000 a month. If they want to sell and roll up, they can come to us and, as long as the quality’s there, probably move quickly.
My advice for beginners: start small and smart. If your budget is $50K, split it into three buckets—you can’t acquire any one asset for more than a third of your budget. That way, even if you make a mistake (or get hit by a random Google update), you’re still in the game for a second or third try, learning more each time. Give yourself room to learn without being knocked out early.
The crazy thing is, once you get going and figure out what works, you can dramatically change your life. We had a guy buy a $180,000 Amazon FBA business, and 22 months later he listed it for over $1.1M; he became a millionaire in under two years. That’s almost impossible with any other asset class.
Once you know what you’re doing, I think it can become safer to buy bigger businesses. They’re less fragile and you can use more creative financing structures—seller financing, using existing contracts as collateral, all that. So start small, but don’t be afraid to scale once you understand the game.
Matt: That’s awesome. Do you have options for people wanting to start really small, like at the lowest end?
Greg: Yeah, we just relaunched MoneyNomad.com. As long as your business makes money and is under $2,000 per month profit (which is the EF minimum), you can list it there. It’s a DIY experience—we connect buyers and sellers, and promote the listings via EF. Early days yet, so only a handful of listings so far, but over time we expect a ton of content sites, KDP, faceless YouTube channels, info product sites—most likely in the $5k–$20k range.
If you’re listening and try it out, Andy and I would love your feedback, even if you hate it. We want to make sure it meets the EF standard, so let us know.
Matt: That’s a great new option for our listeners—check out Money Nomad for both buying and selling. Do your due diligence, as always, but it’s an exciting way to dip your toe in.
Greg: Absolutely! And if you use it, let us know what works and what doesn’t. We want it to be the best micro-acquisition marketplace out there.
Matt: Well, this has been fantastic, Greg. I’d love to have you back on to cover even more opportunities. Thanks so much for sharing your knowledge and firsthand experience. There have been some really good ideas for listeners of every level. We’ll make sure to get you on again.
Greg: There you have it, folks. I hope you enjoyed it—I hope it got you inspired about all the possibilities happening in this industry. If you want to buy a highly profitable business, you can always go to empireflippers.com/marketplace. If you want to make an exit, go to empireflippers.com/sell-your-site.
I’ve been your host, Greg. If you enjoyed this episode, make sure to leave a review, give us a like, a follow, share it across social media. Talk to you all soon. See you on the next episode!
