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The $385k domain we never should have bought
š„ Tips and stories about buying great domains for your new product or business idea
I bought a $375k domain name at my previous company.
(this is not the $385k mistake, that story is further down)
The owner lived in Greece. I sent him 12 cold emails over 12 months. He responded after I upped the offer amount to $50k.

Athens, Greece
He was using it for a travel tourism business in Athens, but the pandemic had just struck. He was open to selling the .com for the .gr domain (what it is today). He named his price and was firm.
We had just raised hundreds of millions of dollars in funding so we didnāt need to negotiate and speed was more important than cost at that time. We accepted.
I was sweating the entire time during the transfer process, especially at the end. I was scheduled to speak at our company all hands to tell the story of how we acquired the domain ā the transfer came through just 30 minutes before I went live š°
This story taught me an important lesson: every domain is for sale. At the right price.
Choosing a name can be complicated, time-consuming, and ā if done too hastily ā create unnecessary friction. Itās something you want to get right the first time and is extremely expensive and arduous to fix down the road.
Iāve named and launched half a dozen of products over the last five years, working with brokers, lawyers, designers, and branding agencies to come up with the best domains for new business lines.
Here are a few of the tips and tricks Iāve learned along the way.
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Is the .com still worth it?
This is a controversial one and thereās no right answer, but my philosophy is yes, it absolutely is and hereās why.
The dotcom makes a strong first impression (you only get one) that your new business or product is a serious company. It demonstrates youāre truly invested and itās more than a side project. All established brands have the dotcom.
Itās not a make-or-break issue (and there are workarounds, as youāll see below) but it does remove potential objections that come up when prospects are deciding to trust a new brand or not.
Should you add words to the domain to get the brand name or .com you want?
For example, if the brand name is a common word, such as āplateā - should you buy a domain like āgetplate.comā or ātryplate.comā?
Iāve found this strategy ends up making the domain the brand name: people start referring to the company as āGet Plate.ā For example, we were called āHopin Toā by some because the early domain was āhopin.to.ā
I advise purchasing the .co or .ai or something similar in order to get the pure brand name in the domain (āplate.coā) if possible.
Should you use a broker?
I do when itās a major domain purchase in the high 5-figures or 6-figures. The downside is the extra expense (usually 10-15% of the purchase price). The upside is the research - they can be really helpful to dig up other hard-to-find domains that are available.
Another benefit is a broker shields your identity from the seller, so if you work at a large company or are a wealthy individual, this is handy. You donāt want the seller to know youāre at a large company or flush with budget and then up the price on you.
Rather than use a broker, I use a burner email address to be āthe brokerā and inquire/negotiate on behalf of āa client.ā
Using creatively āmisspelledā words
When Hopin was getting off the ground, before we had any revenue or investment, the founder asked me if we should use āhopiin.comā or āhopin.toā for the domain.
In almost all cases, a misspelling carries a brand risk. Do you want the first impression of your brand to be perceived as a spelling mistake? It may not matter when youāre small (e.g., beehiiv) or if youāre serving consumers (e.g., TikTok), but an obvious misspelling puts you in immediate competition with autocorrect.
We chose hopin.to because there was a micro-story structured from the domain. You āhop into eventsā since virtual events were easy to āhop in and out ofā in any internet browser.
Check the competition. Does it exist already?
The last thing you want to do is create a name that sends more business to a competitor. Unless you have a ton of marketing budget to make a large, extended splash in the market, a similar name to a competitor will create confusion or worse, legal problems.
Always spend a good hour researching a name online before you plunk down the cash. Itās okay if something is similar but in a totally different industry. Speaking of keywordsā¦
Think about what keywords people will use to find your business
Itās an immediate SEO win if you can place keywords in your domain name. But thereās a drawback:
If your company pivots or expands into more categories (e.g., through acquisitions), youāre in trouble. The domain you bought is now too small of a box. For example, out of 13 rebrand stories, this was the most common reason why companyās rebranded and bought new domains.
For this reason, I wouldnāt be surprised if ComCast ends up rebranding its newly announced Netflix competitor āStreamSaverā ā far too literal and boxes them into being a bargain offering.
It also highlights perhaps the biggest drawback to buying keyword domainsā¦
Be careful with generic words
One of my biggest regrets at Hopin was we bought the domain āsession.comā for $385,000 to rebrand a video meetings tool we acquired called Jamm.
We called it āSessionā - it was a great tool, but it struggled to grow fast enough.
Part of the reason it struggled was the brand wasnāt unique enough to stand out. It didnāt have a strong narrative or imagery built into the word.
It also couldnāt be trademarked and protected because it wasnāt distinct enough - we tried, but it was too descriptive. To be trademark-ready, a wordmark needs to be new or invented.
However, many large brands use generic words:
Hereās the secret that I wish we did with Session ā always use ā.comā in the name. The domain is the brand name. This is how the list above becomes distinct and trademarkable.
Takeaway: if you can help it, choose esoteric over generic.
Another example: We ran into trademark issues with our video hosting platform āStreamableā because the term was too generic.
Legal tip if youāre in the USA: run a quick search using TMSearch (formerly TESS) - the free trademark search tool provided by the USPTO.
What story does the name tell?
Remote staffing startup Shepherd, cofounded by Marshall Haas, just announced today their rebrand to āSomewhere.comā šļø
More big news:
Shepherd is now Somewhere.com !
The best talent is all over the world. You should hire the best and most cost effective person for the job.
Find and hire them with Somewhere!
ā
We dug deep and spent over $400,000 on the domain.
This has been in⦠x.com/i/web/status/1ā¦
ā Marshall Haas š (@marshal)
3:27 PM ⢠May 15, 2024
In his tweet, he shares the story behind the name in one clear, memorable sentence. Itās good.
However, āSomewhereā fails the generic test above.
I wouldnāt be surprised if they run into trouble down the road, unless they keep the dotcom in the brand name (i.e., always refer to it as āsomewhere.comā). Otherwise, itāll get lost in casual conversation - imagine someone saying, āI got my gig from Somewhereā vs. āI got my gig from somewhere.com.ā The dotcom makes it clear youāre talking about a brand.
Last of all: Is it easy to say and spell?
This one is obvious but easily overlooked when entrepreneurs get desperate and swing too far into ādistinctā land.
Itās possible to invent simple yet new words.
Good examples: StreamYard, Mailchimp, Salesforce, Evernote, Google, Kizik, and Upwork.
Aim for two syllables, a straightforward spelling, and a no-pausing pronunciation.
Culture tip: ensure it doesnāt mean anything unintended in slang terms or in another language.
Finally, my last tip is to gut check it with people in your life.
At dinner parties.
With family.
Poll people in casual conversation with 2-4 ideas.
First reactions are extremely valuable feedback.
Itās subjective, but they symbolize a million other individuals who will have the same reaction.
Ultimately, buying a good domain is all about achieving a strong first yet lasting impression. Being memorable - it will serve you, your team, and most of all, your marketing efforts for years to come.
Best of luck.
Dave
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