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The Power of Premium Domains: How Entrepreneurs Are Investing in the Future
By Monica Stankova access_time 28 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. Recognising 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 recognised the immense value of owning a highly memorable and easily recognisable 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 capitalise 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 emphasised 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 recognise 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 recognised PayPal.

In October 2022, Elon Musk acquired Twitter in a high-profile $44 billion deal. In July 2023, he took another big step by rebranding Twitter to X, redirecting the domain to the Twitter platform.

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

Elon Musk’s strategic acquisition of premium domain names continues to make waves. In February 2023, the tech community buzzed with the news that OpenAI had seemingly acquired to point towards ChatGPT. In a surprising twist, it turns out that Musk has acquired that coveted domain, and now is redirecting to, the billionaire’s latest venture into artificial intelligence.

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 acquired the highly coveted domain name During an appearance on the Lenny Rachitsky podcast, Shah disclosed that he had purchased for over “$15 million”, making it the most expensive domain name transaction he has been involved in.

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

Later in the year, Shah revealed in a LinkedIn post that he had sold the domain name to another party, for more than his initial purchase price. He donated $250k of the gains to Sal Khan and Khan Academy to “support their efforts to use A.I. to create personalized education at scale for the world”.

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 emphasising 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 recognised 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 the latest Whoxy data, Amazon Technologies, Inc. currently owns over 477,000 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 recognised 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 personalised 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 emphasising Benioff’s strategic foresight in recognising 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.

Unlocking Success: Marc Lore and Premium Domains

Marc Lore’s entrepreneurial journey is rich with instances of successful domain investments. He founded Quidsi, a company that excelled in using keyword .com domain names as standalone brands. Some of Quidsi’s most well-known brands included,,,,, and Quidsi’s success caught Amazon’s attention, leading to its acquisition in 2010 for approximately $545 million.

In 2014, Lore founded, once again leveraging a strong, simple domain name. His approach paid off handsomely when Walmart purchased in 2016 for $3.3 billion in cash. Subsequent to the acquisition, Lore was entrusted with the role of Walmart’s e-commerce operations’ CEO, a position he held until 2021.

His latest project, Mojo, is hosted on, showing his continued commitment to finding the right digital home for his ventures. His investment in companies like Tornado, which bought, and Wizard, a company that acquired the domain, further demonstrates this commitment.

Lore is also the founder, chairman, and CEO of Wonder Group, a food delivery app that operates on the premium domain

Building something that really pushes the boundaries on the customer experience will earn you true loyalty and customers that won’t stop referring their friends, the most cost effective form of marketing. And, assuming you’ve picked the right industry with a huge market potential, as you grow, you will get the advantages of scale that make your business economically viable. And, that scale combined with an amazing customer value proposition will create a powerful moat around your business.

Marc Lore

Marc Lore’s journey in the digital space highlights the influence of premium domains. He exemplifies how the right domain names can significantly boost online visibility and potentially add substantial value to a business in the long run.

Zuckerberg’s Domain Dynasty: The Facebook Evolution

The evolution from “TheFacebook” to the more streamlined “” in 2005 marked an early recognition by Mark Zuckerberg of the impact a domain name can have. This change was a strategic move to enhance user accessibility and brand recall. The investment in was just the beginning of Zuckerberg’s journey in understanding the power of a good domain name. In 2010, the entrepreneur expanded his digital portfolio by purchasing for $8.5 million from the American Farm Bureau Federation.

I’m here to build something for the long-term. Anything else is a distraction.

Mark Zuckerberg

In 2021, Zuckerberg announced the rebrand of Facebook’s holding company to Meta. To secure this new identity, Meta Platforms spent $60 million on the naming rights for “Meta” from the financial services company Meta Financial Group. Interestingly, the domain was already in Zuckerberg’s possession before the rebrand. This domain was part of a larger acquisition made in 2017 by him and his wife, Priscilla, for their philanthropic organisation.

Reflecting a comprehensive digital strategy, Whoxy data shows that Meta Platforms, Inc. holds a portfolio of over 112,200 domains, while Instagram LLC owns over 11,000 domains. This vast collection includes various extensions and domains that have been strategically acquired for different products and services. It also includes domains that account for common misspellings, ensuring users are directed to the company’s sites even when errors occur in typing URLs, such as,,,,,,,,,,, and many others.

Domains like,,,,,,,,,,,,,,, are only a small part of the rich portfolio of the company.

People don’t care about what you say, they care about what you build.

Mark Zuckerberg

Given his entrepreneurial acumen, it’s no surprise that Mark Zuckerberg has taken steps to protect his personal brand. He owns domains like,,, and, all of which redirect to his personal Facebook profile, showcasing a strategic approach to personal online branding.

Leonid “Leo” Radvinsky: A Visionary Entrepreneur and Domain Strategist

Leonid “Leo” Radvinsky is a Ukrainian-American entrepreneur with a diverse background as a businessman, computer programmer, and venture capitalist. You may not know him by his name, but there is no way you haven’t heard of his ventures like MyFreeCams and content subscription service OnlyFans.

Radvinsky’s business acumen is complemented by his strategic investments in premium domain names. He uses the rare and valuable two-letter domain for his personal website, a testament to his understanding of the value of concise and memorable digital identities. Radvinsky also owns the three-letter domain, under which he operates the venture capital fund. 

Radvinsky’s approach to domain names is a key component of his business strategy, as seen with OnlyFans. By securing both and the more succinct, he has ensured the platform’s strong online presence and easy accessibility, a move that has contributed significantly to the brand’s explosive growth and recognisability.

Radvinsky’s journey in the digital space began at an early age. At just 17, he co-founded Cybertania Inc., a website referral business. In the late 1990s and early 2000s, he developed over ten websites, including Password Universe, Working Passes, and Ultra Passwords, marking his initial steps into the online adult entertainment industry.

In 2004, Radvinsky launched MyFreeCams, and his interest in domain names grew in parallel with his business ventures. A Business Insider article notes that by 2014, Radvinsky had amassed a portfolio of nearly 1,000 domains. This collection included a range of adult-themed URLs, along with their various misspellings and extensions, demonstrating his strategic approach to maintaining control over digital spaces related to his businesses.

Radvinsky’s domain strategy has made headlines, notably with the acquisition of for just under $1 million. This purchase highlights the value he places on premium domains and his vision for their integral role in his business models.

Building a Billion-Dollar Brand: Whitney Wolfe Herd’s Domain Strategy for Bumble

Whitney Wolfe Herd is an influential American entrepreneur renowned for founding Bumble, an online dating platform, and serving as its executive chair and former CEO. Her journey in the tech industry began earlier as a co-founder and the Vice President of Marketing at Tinder, where she played a pivotal role in branding, notably inspiring the app’s name from the easily combustible material, tinder, aligning with the app’s sparking connections theme. Despite her early success, Wolfe Herd left Tinder after filing a lawsuit against the company, which marked a significant turning point in her career.

In December 2014, Wolfe established Bumble, a dating app where women make the first move. Recognised for her entrepreneurial spirit, she was named in Forbes 30 Under 30 in 2017 and 2018, and the Time 100 List in 2018. 

In 2018, she established the Bumble Fund, a venture that invests in early-stage businesses led and founded by women from diverse backgrounds. In February 2021, she became the world’s youngest self-made woman billionaire when Bumble went public, with the company reaching a valuation of $13 billion

For Bumble, Wolfe leveraged a comprehensive domain strategy to enhance the brand’s online presence. In addition to owning, the company has secured a variety of related domains with different extensions, added words, and common misspellings of the brand name, such as,,,,,,,,,,,,,,,, among many others. This domain strategy ensures that Bumble’s users experience seamless access to the platform, protecting the brand and maintaining its strong market presence.

Domain Mastery and Mental Health Innovation: Patrick Nagle’s Journey

Patrick Nagle is a tech entrepreneur and venture investor renowned for creating impactful internet companies. His current venture,, reflects a blend of his professional expertise and personal experiences, dedicated to advancing health technology and promoting self-understanding and connectivity.

Nagle’s entrepreneurial path started with, a platform he launched in 2001, allowing college students to review their professors. As an investor and CEO of this venture, Nagle propelled the site to become the top college website in the nation, a feat that culminated in its acquisition by Viacom.

In 2018, drawing from his personal experiences, Nagle ventured into the health tech space, raising millions in debt financing to acquire As the founding force, initial investor, and CEO, Nagle steered the company to support numerous individuals with rehabilitation, achieving significant growth and a successful business exit without relying on external equity.

Nagle’s most recent venture,, stems from his understanding of the global significance and complexity of mental health issues. As the website’s first investor and Co-Founder, he is applying his two decades of experience to spearhead innovation in the mental health field.

Patrick’s passion for domain names is evident on his personal website,, which showcases his interest in domains. He has amassed a noteworthy portfolio of premium mental health-related domains, including,,,,, and others. These domains underscore his commitment to advancing mental health awareness and support and demonstrate his strategic foresight in securing relevant and impactful online real estate.

A 2014 CBS News article sheds light on another aspect of Nagle’s domain expertise. He owned, which he purchased in 2008. Nagle redirected all traffic seeking basketball news on to his personal LinkedIn profile. He shared in an email to CBS News, “I’ve been buying and selling internet businesses for the past 15 years (since I was 16). I stumbled upon when I co-founded in 2008, an urban social network (later acquired by News Corp). I thought was a great domain, so I bought it.” He also stated that he owned or managed about 3,000 domains and web properties but has since shifted his focus to new business ventures.

Patrick Nagle’s journey underscores the immense potential of well-chosen domains in defining and bolstering a brand’s digital identity and overall impact.

The Visionary Behind Netflix: Marc Randolph

Marc Randolph is an American tech entrepreneur, advisor, speaker and investor. As the co-founder and first CEO of Netflix, Marc played a pivotal role in laying the groundwork for what has become one of the most influential entertainment services globally. His journey with Netflix, from its inception to becoming a household name, is just one chapter in a career spanning over four decades.

Marc’s vision for Netflix began in the late 1990s when he, alongside Reed Hastings, saw an opportunity to revolutionise the way people accessed movies. Interestingly, the company wasn’t always called Netflix. Marc recounts that the original name was “Kibble” before they switched to a more fitting name.

We’d decided that the best name for our company would combine two words: one related to movies, one related to the internet. The best name would combine both terms seamlessly, with a minimum of syllables and letters.

Marc Randolph

Marc highlights the significance of the name “Netflix,” emphasising its flexibility.

The name Netflix gave us the gift of flexibility, a must-have trait for every start-up.

Marc Randolph

Beyond Netflix, Marc’s entrepreneurial spirit has driven him to found or co-found six other successful startups. He co-founded Looker Data Sciences, an analytics software company acquired by Google in 2019 for $2.6 billion. His influence extends to mentoring hundreds of early-stage entrepreneurs and investing in numerous tech ventures, contributing to both successes and invaluable learning experiences from failures.

His extensive experience and insights are also captured in his internationally best-selling memoir, That Will Never Work: The Birth of Netflix and The Amazing Life of an Idea, where he narrates the story of Netflix’s rise.

Marc often shares his wisdom on the intricacies of naming businesses, an essential aspect he believes can make or break a start-up.

Picking a name is incredibly difficult. For one thing, you need something catchy, something that rolls off the tongue and is easy to remember. One- or two-syllable words are best…Too many syllables, too many letters, and you run the risk of people misspelling your website. Too few letters, and you risk them forgetting the name.

Marc Randolph

In a recent X post, Marc Randolph examines the multifaceted nature of naming a company, emphasising the importance of making it easy to remember, providing a .com domain name, and alternate spellings:

Netflix, Inc. owns over 35,600 domains with different misspellings and domain extensions, protecting its brand and ensuring broad accessibility. 

Marc Randolph still owns, a nod to Netflix’s original name, which now redirects to his official site, This site serves as a hub for his insights, advice, and resources, including his book and podcast, reflecting his lasting influence in the entrepreneurial world.

Anand Sanwal: A Leap from Analytics to Domains

Anand Sanwal, co-founder and CEO of CB Insights, is a prominent figure in the business analytics sector. CB Insights, a private company, stands at the forefront of market intelligence, offering a global database that sheds light on the activities of private companies and investors. This platform has become a key tool for those seeking data-driven business insights. Sanwal is also the co-founder of Yardstiq (, CB Insights’ expert network that conducts interviews with software buyers.

His expertise in analysing market trends and business strategies has informed his approach to the digital landscape, particularly in the realm of domain names.

As revealed in a recent tweet, Sanwal is registering domain names with an eye towards future projects and ideas. This initiative reflects his recognition of the value of domain names as vital assets for future branding and business development endeavours.

Exploring the World of Premium Domain Names

The entrepreneurs highlighted in this article represent just a small fraction of those who have recognised 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 recognisable 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 recognisable 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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