20 Questions To Ask When Buying a Website (2026 Edition)

Buying an online business can be one of the smartest financial decisions you ever make. I say this from experience after years of buying, growing, and operating revenue-generating websites, I’ve seen deals that were life-changing and deals that were landmines.

The difference between them?

Asking the right questions before you buy.

Below is a completely updated 2025 list based on current market realities: AI content, traffic volatility, platform risk, compliance, and what I’ve learned helping founders exit on Flippa.

My experience is truly unique as I’ve been actively buying and selling business on Flippa since 2012, and then in 2024 I stepped into a new role as M&A advisor at Flippa where I help entrepreneurs exit their business and investors find great assets to acquire.

This particular article is focused more on investors looking for a great asset, so if that’s you, let’s dive right in!

Buy Smarter. Buy Faster. Buy with Confidence.
Flippa provides everything you need to buy an online business.

Why Read What I have to Say?

If you want to talk about questions, here’s a great question to ask before reading an article. Why should you pay attention to what “this guy” has to say? Looking at my second interview with Flippa back in 2021, I can tell you that since 2021 my beard is not the only thing I have grown. Returns on the websites I bought are steady after 5 years of investing and almost another 5 years of passively collecting revenue. I made all my money back in March 2022, and I still own around 10 websites making around $1000 per month of passive income.

Why such poor results? I spend most of my time working on my company WhoAPI, and the websites that I just mentioned were purchased for passive income. On top of that, they were and still are a great learning experience. I would say this culminated in 2024 when I joined Flippa as an M&A advisor.

Returning back to 2012 when I bought my first website, I really wanted to be involved in this growing industry, even with the limited funds I had at the time I started. I was looking for where to park any cash savings that I had. 

I began with only a $1000, because that’s how much I had to play with. I was clueless about crypto and didn’t like the risk. Then I realized I have experience in web hosting, domain name, WordPress, and other skills that make a good foundation for a website investor and operator.

This allowed me to buy an apartment and move on to a beautiful island in the Adriatic, with amazing beaches within walking distance. Quaint cafes, amazing fish restaurants, and spectacular beach bars are also included and part of everyday life.

One Question for You

Before we start with the list of questions, I have one question for you. Would you like to make $1000 per month passively? Because that’s what I was able to achieve, working from home and buying an apartment on an island. Or better yet, would you like the opportunity to grow the websites you purchased and sell them for six figures? Because that’s how much I think one of my websites could sell for.

If the answer is yes, then here are the questions you need to ask the sellers. Some of these questions you need to ask yourself, and some you need to ask the seller.

1. What is My Situation, and What Set of Questions Do I Need to Ask?

As you can see from my introduction, I was in a very particular situation when I started buying websites. It’s probably quite different to the situation you are in. Maybe you have $1,000 to buy a website, and maybe you have $1,000,000. The questions you will ask are different and won’t even make sense in other situations. For example, if you buy your first website for $1,000, you can’t ask the owner to sign a non-compete agreement. It doesn’t make any sense!

When Blake Hutchinson, the CEO of Flippa, interviewed me in 2020, he asked me what my number one tip for new buyers would be. This is exactly what I told him, understand the scenario you are in and what it is that you are looking for. Very briefly, these are the different factors that can impact your situation:

• Size of the deal. Small website (up to $10,000), medium website / small business (up to $200k), big “website” (over $100k)
• Your experience in buying websites. (First five acquisitions, every acquisition after that)
• Your experience in managing websites (No technical, design, sales, or copywriting skills, some skills, seriously skilled)
• Type of the website. Content, eCommerce, SaaS, starter site, no monetization, dropshipping, or YouTube channel, app portfolio, games and other digital assets.
• Your sweat equity (Part-time like a side gig, full-time like a new career, or are you flipping)

Buy Smarter. Buy Faster. Buy with Confidence.
Flippa provides everything you need to buy an online business.

2. Is This Too Good to be True?

The golden rule of buying anything holds with buying websites as well: if it seems too good to be true, it probably is. Air Jordans for $40? Used 10-year-old Audi TT with 40,000 miles on it for $5,000? A website making $1,000 per month on sale for $12,000? 

No matter how much due diligence you put into it, if something sounds like the deal of the century, and you think that you are the lucky one who found it… Then you will make the same mistake I did and waste $2,000 on your first deal. The problem with websites, unlike cars or fake sneakers, is the only thing you are left with is a worthless domain name you have to renew for $8.57 annually.

3. What Does the Website’s History Look Like?

Bookmark Web Archive (Wayback Machine), and check what the website looked like a year ago, 5 years ago, and 10 years ago. Doesn’t have that much history? Why not? Is there a different domain name where the website originally started? Which domain, why was it done that way, and what does the history look like on those domains? Are there any people mentioned on the about us page, are these the same people selling you the website? On some deals, I spend more time on Web Archive than I do on flippa.com, and you should too.

4. Is the Domain Name Worth Anything?

What’s the first thing you see when you look at a website? What’s the first thing you say when you want to tell someone about the website you purchased? That’s right, a domain name. Since my business WhoAPI deals a lot with domain names you could say I know a thing or two about domain names. Having said that, I have also paid thousands of dollars for a domain name because a domain name is like a location of your office space.

5. What Impact Does the Seller have on the Business / Website?

When you are buying a website, you essentially have to make plans to take over. Taking over from someone else generally means that you or your team can resume where the old owner left. In a best-case scenario, you can improve upon what’s already built. With that in mind, it’s a great idea to learn if the seller was an SEO wizard, a social media mogul, a fantastic engineer, an outstanding designer, a slick salesman, or a shrewd business person. What is their overall online reputation? In other words, will you fit into those shoes, or will they be too big?

Buyers often ask how much support seller is willing to provide. This can be more valuable than a paid course, but it can also be a setback if the seller quickly disappears.

Buy Smarter. Buy Faster. Buy with Confidence.
Flippa provides everything you need to buy an online business.

6. What is the Real Reason they are Selling this Website?

Flippa is always making an effort to vet both the websites and the sellers listed on their platform. That said, just like everything else in the world, you will have reputable sellers asking for a premium price and a newcomer offering their websites below average asking price. In my experience, price alone is not a guarantee that the website or the seller is reputable or the reason someone is selling. So you have to find another way and try to understand the real reason someone is selling a website.

7. What Level of Expertise is Required?

Similar to question number 5. Speaking of experts, do you have what it takes to take the website to the next level? If the seller states he never worked on the site’s SEO, could it be that executing good SEO is really hard? Or just that the seller doesn’t have those skills? Don’t let this put you off your first acquisition, but understand what you are getting yourself into. 

Having said that, have in mind that sometimes it pays to take a risk. In 99% of my website acquisitions, I didn’t buy a website that’s built on Django. Do you want to guess which framework is under the website’s hood that brings me the best returns? I’ll give you a hint, it’s not WordPress. I am not saying Django makes money, but stepping outside of your box sometimes does.

8. Was the Website Ever Sold in the Past?

Not only can you find out if the website was ever sold, but you can also check if the domain name was bought on the aftermarket. Well, at least if the sale was reported. Our third question was all about history, this question expands on it. You should check the website’s sale history, including any website or domain name sales in the past.

If you are buying a website on Flippa, ask support if this business sold in the past on Flippa.

9. How Old is the Website?

A particularly important part of the historical check of the due diligence is age. How old is the website, how old is the domain name, and how old is the traffic? Flippa has partnered with SEMRush for a good reason. Open a free SEMRush account, and check what the traffic looks like over two years or more. You can check the history of any website, so do it before you bid on a website. Check Google Analytics, and go back as far as you can.

10. Are There Any Potential Legal Issues?

Here are some questions you need to ask yourself about legality. Is the website infringing on any name marks or trademarks? Is content that’s published rightfully owned or scraped from Web Archive and then plastered on an expired domain name? Why ask these questions yourself and not the seller? Maybe the seller is ignorant of the registered trademarks, and maybe they think it’s not a big deal. Maybe they bought the website from someone else. Since 2024 a lot of the content is written with AI, so check that as well.

If you need help with comprehensive due diligence, Flippa’s team offers that service. It’s worth looking into that if you want that advantage on your side, especially if you are a first-time buyer.

Buy Smarter. Buy Faster. Buy with Confidence.
Flippa provides everything you need to buy an online business.

11. How Does the Website Make Money?

You want to be clear and understand how the website makes money. Or “monetization”, as the seasoned website investors like to say. Furthermore, will you be able to continue making money in the same way, diversify the revenue and even increase it? You can also look into customer acquisition channels, customer acquisition costs, and conversion rates. Is the website getting traffic from search engines or social media channels? Are you proficient in those skillsets? Are you good at conversion rate optimization? Can you make considerable improvements in any of these areas? 

12. What Does the Website Look Like (UX, UI)?

When you open the website, do you like what you see, or does the website need a major redesign? Are you a great designer, or know someone who can help you? Can you update the design with your skillset? Is the website’s usability great, does it make you want to read another article? Do you see thought-provoking content? Is bad design an opportunity or a challenge for you?

13. What Does the Website Look Like from a Technical Perspective?

There’s so much you can do to check the website from a technical perspective. You can check the website’s speed with Google’s PageSpeed Insights. You can check on-page SEO, link structure, and dead outgoing links. Speaking of backlinks, this might be a great time to mention checking the backlink structure. Do you see any suspicious websites sending a lot of backlinks to the website you want to purchase? Will those backlinks remain or miraculously disappear after the sale? Again, is this something you can fix?

14. Who are Your Competitors?

If you buy a website for anything close to six figures, you definitely want to check your competitors. The last thing you want is your seller starting a new business with your money and then competing with you. During the due diligence process, you want to check who is competing with you on traffic, who is selling similar products, and who is the 800-pound gorilla in this space.

Buy Smarter. Buy Faster. Buy with Confidence.
Flippa provides everything you need to buy an online business.

15. What’s Your Exit Strategy?

There are so many questions I can write, and you can see that up until now, I haven’t asked just 15 questions; it’s way more. Exit strategy is how you will end your website acquisition. Even if you don’t have an exit strategy, you actually do. It’s death – or end, if I am not allowed to be so stoic about it. End of technology (Flash), end of a trend (PBNs), end of content writing (ChatGPT) or end of something else. On the other hand, you may plan to sell to one of your competitors, a strategic buyer, or “return to the source” and sell the website on Flippa, where you bought it. 
Ask yourself, will I sell this website or own and operate it for as long as possible?

As an M&A advisor I have brokered several six-figure deals for Flippa during my first year. Including one in record speed (just 10 days). I’ve heard thousands of questions potential buyers ask sellers. So here are 5 most common ones, that I maybe missed in the first 15 questions, because they are more tactical (as opposed the first 15 being more strategic and more of a 30,000-foot overview).

16. Can I Get Added to Google Analytics?

Buyers want to get a better view of the traffic to the website. It’s important to distinguish between SEO traffic, paid social media traffic or AI traffic such as ChatGPT and Anthropic.

This will help you understand not only how many users access the website on a daily basis, but also where they are coming from geographically and from which traffic sources.

17. How Long has the Seller Owned the Site and How Did it Come into Their Posession?

As soon as you step into mid 5 figures and 6 or 7 figure territory, it’s all about the P&L. This is a spreadsheet with “Profit and Loss” which essentially conveys how the business is making money and what expenses are absorbed in order to generate revenue.

A Shopify store will have a different P&L from a SaaS, or from a YouTube channel. There is a lot of scrutiny when it comes to P&Ls because sometimes the sellers don’t list all the expenses, and then you as a buyer have to determine what other expenses (unforeseen or not) impact the business and it’s profitability. Ultimately, this will determine what kind of offer you can make, and impact how quickly you get an ROI.

Buy Smarter. Buy Faster. Buy with Confidence.
Flippa provides everything you need to buy an online business.

18. Why are You Selling Your Business

Honestly, I never really cared about this question, because sellers can make stuff up, and there’s really no way you can find out the real reason why someone is selling a business. 

However, working as a broker, I’ve learned that this is one of the most frequent questions! Don’t get me wrong, I understand that buyers want to detect risk, and in hope that the seller will “spill the beans” and confess why they are selling the business. So even though you should definitely ask this question, I always take the seller’s answer with a grain of salt.

If you are lucky, a seller’s answer could potentially give you leverage.

19. How Many Hours do You Spend Working in the Business?

“Passive income” gets thrown around a lot, but buyers aren’t looking for that. They’re simply trying to make sure they’re not buying a job.

When someone spends six figures on an acquisition, they want a business that runs without requiring 40+ hours a week from them. This question helps buyers understand:

• What tasks the seller handles personally
• How many of those tasks can be outsourced
• Whether the business can run smoothly without the founder

The less the business relies on seller’s daily involvement, the more attractive and valuable it becomes.

20. Bonus Questions from a M&A Veteran

I’ve reached out to mergers and acquisitions veteran Joe Bardenheier. I met Mr. Bardenhier a few years ago while he was working for Endurance International Group (now Newfold Digital). He worked there for over 17 years while completing 80+ deals worth more than $1.75 Billion. Here’s what he likes to ask:

1. What value can I add in revenue generation and/or cost reductions to this asset that might bring down my effective purchase multiple over the next 12-24 months?
2. Does this asset fit my overall strategy and core competency, am I going to have time to manage it well?
3. If the price is on the lower end of the scale, is it “too good to be true”?

If you are having second thoughts about your first purchase after reading this article, that’s normal. You want to be a little scared going into your first acquisition, but remember that this has the potential to turn into excitement if you are well prepared. Hopefully, this article did just that. Feel free to use these questions as a checklist when you are evaluating a website. Good luck with your purchase!

Buy Smarter. Buy Faster. Buy with Confidence.
Flippa provides everything you need to buy an online business.