Buy Fast, Not Blind: 15 Minutes Will Save Your Ass

I almost spent $8,500 for a domain last year. I was ready, finger hovering over the confirm button. Then I decided to do A trademark search.

Turns out there was an active trademark filed three months earlier. Same exact name. Same industry I was planning to use it in. Would've been a complete disaster.

Fifteen minutes of checking saved me from what could've easily turned into a $20,000 legal mess. And I've been doing this for almost twenty years - you'd think I'd learn to just automatically do the checks first. But that FOMO hits hard when you find a domain you love.

Most due diligence posts read like you need to hire a team of lawyers and spend a week researching every domain. That's great if you're buying premium .coms with six figures. But most of us are making decisions fast, sometimes in a live auction with two minutes left on the clock.

So here's what I actually do now. Takes me about 15 minutes, catches most of the problems before they cost me money. It's not perfect but it works.

Stop trying to justify the purchase

That's when I make mistakes.

So now I flip it. I'm actively trying to find reasons NOT to buy. I'm looking for dealbreakers. If I can't find any after running through everything, then yeah, probably worth buying.

How I actually do this

I go straight to the USPTO database. The interface is basic but whatever, it works.

I search the domain name without the extension. Then I'll try plurals if it makes sense, maybe the singular version if I'm buying the plural. Sometimes I'll search related terms if I'm feeling thorough, but honestly sometimes I skip that if I'm in a hurry.

I'll also hit the Global Brand Database for international trademarks if it's a domain I'm spending real money on. Takes maybe three extra minutes. The EU database too if I remember, which honestly I don't always on cheaper domains.

Then I Google "[domain term] trademark" or "[domain term] brand" just to see what pops up.

What I really care about is whether someone's actively using this in the same space. Here's the part that trips people up - trademarks exist in different classes. There's like 45 classes total. Class 25 is clothing. Class 36 is financial stuff. If I'm buying a domain for a SaaS product and there's a trademark in Class 25 for t-shirts, I'm probably fine. Different worlds.

But Class 35 and 41? That's advertising, business services, education, entertainment - the broad stuff that bleeds into everything online. Those make me nervous no matter what I'm planning.

The question I ask myself: Could a regular person think my buyer is connected to whoever owns the trademark? If yes, I'm out. If maybe, I keep digging but I'm already getting nervous.

Generic terms are safer. "BlueFinancing" is probably fine because it's just two regular words. But if it sounds like a made-up brand name that already exists - like "Zyltrix" or something - I'm way more careful. Those coined terms are usually trademarked hard.

Dead trademarks don't keep me up at night. Something that got abandoned in 1994? Ancient history. But if I see a trademark application filed in the last year and it's still pending? That person is actively protecting that brand RIGHT NOW.

Dealbreakers at this stage:

• Famous brand anywhere near it
• Made-up word that someone else clearly invented first
• Multiple active trademarks in the same industry

I Google the domain term without quotes and look at the first couple pages of results.

Is there a company already using this name? Do they dominate the search results? Is there already a .io or .ai site ranking for this term?

If one company owns the first page of Google and they don't own the .com, it's complicated. Sometimes that's opportunity - they might want to upgrade. Sometimes it's a legal nightmare waiting to happen. Depends on the situation.

Then I search for news about the term plus "lawsuit" or "scam" or "complaints." I'm trying to avoid buying a name that's tied to something ugly. I'll also search the UDRP databases - WIPO's is public. If the domain was involved in a UDRP case or some public mess, I usually pass. Not worth it.

I'll also do a quick check on Twitter, Instagram, LinkedIn for the handle. If the same company has the handle everywhere with thousands of followers, they probably consider it their brand. That's useful information even if it's not a dealbreaker.

Checking the history

Wayback Machine is next. Takes like twenty seconds. What was on this domain before?

If it was a gambling site, pharma spam, or adult content, that's baggage I have to price in. Maybe the domain is still worth buying but I need to factor in cleanup time and potential buyer concerns. Google doesn't forget. And if the trademark owner sent nastygrams to the previous owner, guess who they're coming after next?

If it was a real business with actual content, I look at whether there's still value there or just problems. Sometimes old content helps. Sometimes it hurts.

I'll look at WHOIS history if I have access. If the domain has been flipped five times in two years, that tells me something. Either there's a problem with it or nobody can figure out how to sell it.

Quick backlink check too - I'm not buying domains for SEO but I don't want to inherit a toxic link profile either. If it's all spam links, buyers will see that too.

Then I write down three types of buyers who might want this. Like:

• SaaS company doing receipt tracking
• IT services company rebranding
• Fintech startup in SMB lending

Last few minutes: Money and final check

I look at what similar domains have sold for. Not trying to find perfect comps, just a ballpark. Is this a $2,000 domain? $8,000? $25,000? I need to be in the right range or I'm wasting time.

Then I write down two numbers - what I think I can sell it for, and what I'd accept as a floor. If I hold this for two years, does the math still work? If my gut says no, I let it go.

Final gut check on three things:

• Trademark clean enough?
• Reputation clean enough?
• History acceptable?

Red flags I've learned to respect

Made-up words that aren't yours - If it looks like an invented brand name, it probably is. Just not by you.

Regulated industries with aggressive lawyers - Crypto, healthcare, financial products. These spaces get litigious fast.

Bad reputation that won't die - If Google ties the name to a scandal or lawsuit, you're going to spend years trying to outrun that. Not worth it.

UDRP history - If the domain's been in disputes before, assume the next owner inherits that attention. If that domain already lost a UDRP and you're buying it from auction, you're just inheriting someone else's loss.

Only one obvious buyer - That's not a buyer map, that's a gamble.

Good signs

• Clear category fit that works for multiple industries
• Clean history - parked, light use, or old defunct site with normal content
• Works as both a product name and company name
• Easy to say on the phone - person hears it once and spells it right
• Active brands using the exact term on .io or .co (means someone might want to upgrade)

How this changes what I'll pay

If I find a small flag - like trademarks in unrelated categories - I don't always walk away. Sometimes I just change my pricing. Maybe I was thinking $5,000 but now I'm at $3,500 and targeting smaller buyers with clearer use cases.

But a big flag like famous brand adjacency? I'm out completely. Rather miss a good domain than buy a legal problem.

The actual checklist I use

Trademark check:

• USPTO TESS search - exact matches and close variations
• WIPO/Global Brand Database for international (if over $2K)
• Google "[term] trademark" - confusion risk?
• Check trademark classes - especially 35 and 41

• Google first two pages - who owns this term?
• UDRP database search (WIPO, others)
• News search for lawsuits/scams/complaints
• Social media handles check

• Wayback Machine - previous content acceptable?
• WHOIS pattern - stable ownership or churning?
• Backlinks - normal or spam farm?
• Write down three realistic buyer types

• Comparable sales range
• My ask price and floor price
• Final red flag recap

Speed vs certainty

I've walked away from domains I really wanted because something in this process flagged. And I've never regretted it. What I have regretted is the times I skipped steps because I was in a hurry or excited about a name.

But I can also say I've never lost a UDRP (never had one). Never gotten a cease and desist letter. Never had to hire a lawyer to defend a domain purchase. That's worth fifteen minutes every single time.

The point isn't to predict everything that could go wrong. It's to catch the obvious stuff - the trademarks that will come after you, the reputation problems that will kill buyer interest, the names that only ever had one imaginary buyer.

I'd rather have a smaller portfolio of clean domains than a big portfolio with problems scattered through it. This process helps me sleep better at night.

The one time you skip these checks is going to be the time you buy a $3,000 problem that costs you $10,000 to fix. I've seen it happen to other investors. Not interested in learning that lesson the hard way myself.