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The Power of Premium Domains: How Entrepreneurs Are Investing in the Future
By Monica Stankova access_time 15 min read

A domain name is vital in building an online business presence, often the first touchpoint for people when searching for a company. It functions as a virtual address that directs customers to a company’s website, where they can interact with its products or services. However, not all domain names carry the same weight.

Premium domain names, highly sought-after in the digital marketplace, stand out due to their brevity, memorability, and ease of spelling. These attributes make them incredibly valuable for businesses aiming to establish a robust online presence.

Beyond simply establishing brand identity, premium domain names can significantly enhance a website’s visibility. Possessing a memorable and easily identifiable domain name attracts more traffic, potentially leading to increased sales and revenue.

A premium domain name also lends credibility and professionalism to a business, fostering trust among potential customers and spurring them to engage with the brand. Recognizing the considerable impact a premium domain name can have on a business’s success, entrepreneurs are often prepared to invest substantial sums in acquiring one.

A better domain name will lower your lifetime marketing costs.

Frank Schilling

This article takes an in-depth look at the inspiring success stories of entrepreneurs who have made substantial investments in premium domain names. These visionary business leaders recognized the immense value of owning a highly memorable and easily recognizable domain name, understanding that it could significantly impact their brand’s growth and online presence.

We will explore the factors that motivated these entrepreneurs to invest in premium domain names, as well as the strategies they employed to capitalize on their investments. By examining the challenges they faced and the victories they achieved, we aim to provide valuable insights and lessons for aspiring entrepreneurs considering a similar path.

Michael Saylor: The Domain Name and Bitcoin Advocate

Michael Saylor, an American entrepreneur, is the CEO and founder of MicroStrategy, a leading provider of business intelligence, mobile software, and cloud-based services. In addition to being a prominent advocate for Bitcoin and cryptocurrency, Saylor has demonstrated a keen understanding of the value of premium domain names.

If you own a word that is easy to spell and remember with positive connotations, like Apple, Amazon, etc., it will be very useful. If you own such a word, you can put a business on it. The logic of this is if a billion people see the name and they can remember and spell it, surely, they will be able to type it. If I have a company name that has a difficult name with no positive connotation, people will have a harder time remembering it.

Michael Saylor for BtcBox

In 2019, MicroStrategy made headlines when it sold the domain name for a staggering $30 million. The sale set a new benchmark for domain name transactions and emphasized the potential value of premium domain names.

Saylor’s involvement in the domain name industry extends beyond the sale of MicroStrategy has owned and managed a portfolio of premium domain names for many years. The company has a long-term vision for these domains, either using them for their own projects or selling them to other businesses that recognize their value.

Another important factor is the dotcom domain. If the word that you own is not on the dotcom domain, it falls off in value. People have a harder time remembering it if it was dot io, dot org, or dot tv. Moreover, if the word is too long, it falls off in value too. If 65%~ 80% of the money on commerce around the world is in English, and if you own one of the 1000 most important words in the English language, you can treat the domain as a business. For example, imagine what Apple would pay to get today. If you own that word, then you are owning an asset similar to digital real estate. It’s like owning a block in Manhattan, the biggest city in the world except if you own a precious domain name, it’s like owning the central block in every city in the world.

Michael Saylor for BtcBox

Michael Saylor’s philosophy on premium domain names is in line with his belief in the growing importance of digital assets. He sees domain names as a form of “digital real estate” that can appreciate in value over time, much like how he views Bitcoin. This perspective highlights the potential for domain names to serve not only as a branding tool but also as a valuable investment.

Elon Musk: The Visionary Entrepreneur

Elon Musk, CEO of SpaceX, Tesla and Twitter, has long demonstrated a keen understanding of the immense potential that premium domain names hold. In 2017, he made headlines by reacquiring the rare single-letter domain name from PayPal. is of historical significance for Musk, as it was the domain name associated with the online payment service he founded in 1999, which later merged with Confinity to create the globally recognized PayPal. While the future plans for remain uncertain, the acquisition underlines Musk’s commitment to securing high-quality domain names for his groundbreaking ventures.

In addition to, Musk’s Tesla Motors made a significant investment in acquiring the domain name in 2016, a move that was crucial in solidifying Tesla’s branding and online presence. Prior to the acquisition, the domain had been held by Stuart Grossman, a Silicon Valley computer network engineer since 1992. However, after a decade of negotiations, Tesla successfully acquired the domain for a reported $11 million.

Buying took over a decade, $11M & amazing amount of effort. Didn’t like even when we were only making cars.

Elon Musk, Tesla

The acquisition of was a strategic move by Musk, who saw the value in having a simpler and more encompassing domain name that better reflected Tesla’s expanding product line beyond just electric vehicles. Musk envisioned Tesla as more than just a car company and wanted to reflect this broader vision through the company’s online identity. The acquisition allowed Tesla to streamline its online presence and create a stronger brand image that encompassed its energy solutions and other innovative products.

Dharmesh Shah’s Take on Domain Names

Dharmesh Shah, the co-founder and CTO of HubSpot, is also a strong believer in the power of premium domain names. In March 2023, Shah purchased the highly coveted domain name for an undisclosed eight-figure amount ($10M or more), marking the most expensive domain name transaction he has ever been involved with.

The reason I bought is simple: I think Chat-based UX (ChatUX) is the next big thing in software. Communicating with computers/software through a natural language interface is much more intuitive. This is made possible by Generative A.I. is absolutely brilliant in terms of simplicity, shortness and being totally *on point* and meeting the moment. It immediately creates user trust. Somebody (not me) will build a massively successful product/company on it.

Dharmesh Shah

It appears that Dharmesh Shah had his eye set on another high-value domain name in addition to During an interview on the popular YouTube channel “My First Million,” Shah revealed that he had also acquired in a separate seven-figure transaction.

This isn’t the first time Shah has made a significant investment in a premium domain name. In 2022, HubSpot acquired for a whopping $10 million, further emphasizing the value he and his company place on prime digital real estate. Following the news of the acquisition, Shah shared his thoughts on LinkedIn, confirming that it was a personal transaction not tied to HubSpot.

Over the decades, I’ve learned about the importance and value of domain names. (my word-game) has hit 150 million games played and 16 million users. I know for a fact that a lot of this is because the domain is easy, memorable and fun.

Dharmesh Shah

While the exact acquisition price remains undisclosed, Shah’s commitment to securing high-quality domain names demonstrates his foresight in strengthening the digital presence of his ventures.

Mark Cuban: The Domain-Savvy Billionaire Entrepreneur

Mark Cuban is a well-known American entrepreneur, investor, co-owner of 2929 Entertainment and owner of the Dallas Mavericks NBA team. With a net worth of over $4 billion, Cuban has made a name for himself in the business world as a savvy investor and innovative thinker. One aspect of his success that often goes overlooked, however, is his strategic use of domain names for his various companies and personal brands.

Cuban has been acquiring a rich portfolio of top domains for many years, using them to establish and promote his brands in a variety of industries. Some of the domains he owns include,,,,,,,,,,,,, and many more. These domain names are carefully chosen to reflect the values and goals of Cuban’s businesses and to make it easy for potential customers to find them online. If you’re interested in learning more about Mark Cuban’s companies and the strategic domain names he has chosen to represent them, be sure to check out our comprehensive article on the subject.

Make your product easier to buy than your competition, or you will find your customers buying from them, not you.

Mark Cuban

Cuban also greatly values personal branding, as seen through his domain names and He has also secured domain names for his family members, including,, and

In 2019, Cuban made headlines for his acquisition of the domain name He reportedly made the purchase on a whim “to make sure someone didn’t do something crazy with it,” according to an interview with The Times. This move is a testament to Cuban’s forward-thinking approach to branding and his willingness to invest in domain names that have the potential to become valuable assets in the future.

Overall, Cuban’s use of domain names is just one example of his innovative and strategic approach to business. By carefully selecting and investing in high-quality domain names, he has been able to establish and promote his brands effectively, both online and offline. As he continues to expand his portfolio of companies and investments, it will be interesting to see how he continues to use domain names to his advantage.

From Cadabra to Amazon: The Domain Name Journey of Jeff Bezos

Jeff Bezos, the founder of Amazon, is widely recognized as one of the most successful entrepreneurs of our time. In addition to his well-known business acumen and vast wealth, Bezos has also demonstrated a keen eye for strategic domain names. According to latest Whoxy data, Amazon Technologies, Inc. currently owns over 210,000 domain names, which is a testament to the importance that Bezos places on this aspect of branding. However, the journey to the iconic name “Amazon” was not without its twists and turns.

Jeff Bezos initially named the company “Cadabra Inc.” as a nod to the magical nature of online shopping. However, due to the risk of the name being misheard, he wisely changed it to Relentless, securing the domain. Despite considering other options such as and Bezos eventually settled on “Amazon” – a name that encapsulated his vision of a company as vast and powerful as the Amazon River. Even to this day, Amazon still owns these domain names, highlighting the importance of securing them as long-term valuable brand assets.

A brand for a company is like a reputation for a person. You earn reputation by trying to do hard things well.

Jeff Bezos

With his forward-thinking approach to branding, it’s no wonder that Bezos has achieved so much success over the years, and it will be exciting to see what other innovative strategies he will employ in the future.

Marc Benioff’s Strategic Domain Name Collection

Marc Benioff, the founder of Salesforce, is a seasoned player in the tech industry. He has long recognized the importance of domain names as a key aspect of a company’s branding and marketing, and his extensive collection of premium domain names attests to this fact.

In 2020, the launch of, a startup seeking to create a more efficient and personalized search engine, quickly garnered attention. The company raised $20 million in funding in 2021, with Marc Benioff leading the investment round. Notably, Benioff was the previous owner of the domain, which he had acquired as part of his collection of premium domain names, including high-profile names like,, and

Benioff’s strategic use of domain names extends beyond his own ventures, as evidenced by his gift of the domain to Steve Jobs, the late co-founder of Apple. The story recounted in Benioff’s book, Trailblazer, reveals how Jobs planted the seed of the idea for the first enterprise app store and how Benioff eventually paid Jobs back with the gift of the domain as a gesture of appreciation. And to date, the domain redirects to the Apple App Store, further emphasizing Benioff’s strategic foresight in recognizing the potential value of domain names.

You need to get to the future, ahead of your customers, and be ready to greet them when they arrive.

Marc Benioff

Jordan Fried: A Serial Entrepreneur and Brand Builder

Jordan Fried is a renowned serial entrepreneur who, over the years, has built an impressive roster of successful businesses such as Buffered VPN, Hedera Hashgraph, Immutable Holdings,, and, to name a few. 

Recognising the immense value and potential of premium domain names, Freed has strategically invested in these digital assets throughout his entrepreneurial career. This approach highlighted the impact that a strong brand and a compelling domain name can have on business growth and exposure.

Don’t be cheap! A good brand can make or break or business and domain names are a crucial extension of your brand. A brandable domain name will cost some money but will more than pay for itself in the trust you build with your customers. Domain names are investments. Think of a domain name like internet real estate. It used to be unfathomable that a domain name could be worth millions but now domain names regularly sell for over $1 million. The domains I’ve purchased consistently go up in value.

Jordan Fried

Freed also recogniсes the importance of personal branding in today’s business world. His ownership of and is a clear demonstration of his commitment to developing and protecting his personal brand. These domain names serve as powerful tools that allow him to establish a consistent online presence, demonstrate his expertise, and build trust with his target audience.

Exploring the World of Premium Domain Names

The entrepreneurs highlighted in this article represent just a small fraction of those who have recognized the immense value of premium domain names in establishing a successful online presence. From Michael Saylor’s view of domain names as “digital real estate” to Mark Cuban’s strategic use of domain names for his various companies and personal brands, these business leaders understand the importance of owning a memorable and easily recognizable domain name.

If you’re interested in exploring the world of premium domain names further, we recommend checking out our articles on the topic. At SmartBranding, we have a wide range of resources that can help you navigate the complex landscape of premium domain names and understand their value. Some of our articles include:

It’s essential to do your research and stay informed, whether you’re a business owner looking to secure a memorable and easily recognizable domain name or an investor seeking valuable digital assets. By understanding the importance of premium domain names and the factors that influence their value, you can make smart and strategic investments that will help you achieve your goals.

A premium domain name can make all the difference in building a successful brand. If you want to take your business to the next level, consider investing in a premium domain name. Contact us today for more information and assistance in finding the perfect domain for your brand.

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