The $385k domain we never should have bought

🔥 Tips and stories about buying great domains for your new product or business idea

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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 didn’t 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 — the transfer came through just 30 minutes before I went live 😰 

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 — if done too hastily — create unnecessary friction. It’s something you want to get right the first time and is extremely expensive and arduous to fix down the road.

I’ve 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 I’ve learned along the way.


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Is the .com still worth it?

This is a controversial one and there’s no right answer, but my philosophy is yes, it absolutely is and here’s why.

The dotcom makes a strong first impression (you only get one) that your new business or product is a serious company. It demonstrates you’re truly invested and it’s more than a side project. All established brands have the dotcom.

It’s not a make-or-break issue (and there are workarounds, as you’ll 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 “plate” - should you buy a domain like “” or “”?

I’ve found this strategy ends up making the domain the brand name: people start referring to the company as “Get Plate.” For example, we were called “Hopin To” by some because the early domain was “”

I advise purchasing the .co or .ai or something similar in order to get the pure brand name in the domain (“”) if possible.

Should you use a broker?

I do when it’s 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 don’t want the seller to know you’re 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 “the broker” and inquire/negotiate on behalf of “a client.”

Using creatively “misspelled” words

When Hopin was getting off the ground, before we had any revenue or investment, the founder asked me if we should use “” or “” 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 you’re small (e.g., beehiiv) or if you’re serving consumers (e.g., TikTok), but an obvious misspelling puts you in immediate competition with autocorrect.

We chose because there was a micro-story structured from the domain. You “hop into events” since virtual events were easy to “hop in and out of” 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. It’s okay if something is similar but in a totally different industry. Speaking of keywords…

Think about what keywords people will use to find your business

It’s an immediate SEO win if you can place keywords in your domain name. But there’s a drawback:

If your company pivots or expands into more categories (e.g., through acquisitions), you’re 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 company’s rebranded and bought new domains.

For this reason, I wouldn’t be surprised if ComCast ends up rebranding its newly announced Netflix competitor “StreamSaver” — far too literal and boxes them into being a bargain offering.

It also highlights perhaps the biggest drawback to buying keyword domains…

Be careful with generic words

One of my biggest regrets at Hopin was we bought the domain “” for $385,000 to rebrand a video meetings tool we acquired called Jamm.

We called it “Session” - it was a great tool, but it struggled to grow fast enough.

Part of the reason it struggled was the brand wasn’t unique enough to stand out. It didn’t have a strong narrative or imagery built into the word.

It also couldn’t be trademarked and protected because it wasn’t 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:

Here’s the secret that I wish we did with Session — always use “.com” 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 “Streamable” because the term was too generic.

Legal tip if you’re 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 “” 👉️ 

In his tweet, he shares the story behind the name in one clear, memorable sentence. It’s good.

However, “Somewhere” fails the generic test above.

I wouldn’t 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 “”). Otherwise, it’ll get lost in casual conversation - imagine someone saying, “I got my gig from Somewhere” vs. “I got my gig from” The dotcom makes it clear you’re 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 “distinct” land.

It’s 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 doesn’t 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.

It’s 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.


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