Root.com: The 30-Year Journey of an Iconic Keyword Domain—From FreeBSD to $1.3M Insurance Acquisition

Got root?

In computing, the term "root" holds foundational significance. It represents ultimate authority and access. In Unix systems, the root account—also known as the superuser—possesses unrestricted control over the operating system, capable of modifying any file, process, or configuration.

Root also represents the underlying structure of file systems, where all directories and paths originate from the root directory (/).

The matching .com domain, Root.com, was registered in early 1994, at a time when domain registrations were free. The domain would change hands several times over three decades before being acquired for $1.3 million by Root, Inc., an insurance company, in 2022.

The story of Root.com is the story of the early internet itself—registered by a Unix pioneer, used to promote open-source software, sold to a CPA with the matching name, and finally acquired by a tech-forward insurance startup that needed the perfect brand match.

1994: The Free Registration Era

Root.com was registered in early 1994, during the brief window when domain registrations were completely free. At the time, the commercial internet was still in its infancy, and the strategic value of single-word domains wasn't yet understood.

The original registrant? David Greenman, a co-founder of the FreeBSD project—a version of the Unix operating system.

This wasn't a lucky coincidence. Greenman (known as "DG" in the Unix community) understood the significance of "root" better than almost anyone. As a FreeBSD co-founder, he was working on the very systems where "root" meant ultimate control.

Registering Root.com for a Unix pioneer was like registering Drive.com for a car company founder. The domain matched the work perfectly.

1999: Promoting FreeBSD

By 1999, Greenman had web content live on Root.com, using the domain to promote FreeBSD. Archive.org captures from this period show the domain serving as a resource for the FreeBSD project.

At the time, FreeBSD was (and still is) a powerful, open-source Unix-like operating system used in servers, embedded systems, and network appliances. Companies like Netflix, WhatsApp, and Sony have used FreeBSD in their infrastructure.

Root.com served as a promotional hub for this critical open-source project, living up to its name by supporting the very systems where "root access" mattered most.

2001-2003: The Business Pivot

By 2001, the domain's content had switched to Tera Solutions, a RAID systems company where Greenman served as president. RAID (Redundant Array of Independent Disks) is a data storage technology that combines multiple disk drives—highly technical work that fit the "root" theme of foundational infrastructure.

By 2003, Root.com presented content from Download Technologies, another company owned by Greenman. That domain's content hasn't changed much in the past 20+ years, suggesting the company may have been inactive or the website simply never updated.

For nearly a decade, Root.com served as Greenman's primary business domain, evolving from open-source advocacy to commercial enterprise.

2004: The Name-Match Sale

By November 2004, Root.com had been sold to a CPA services company. The owner? M. Darren Root.

This wasn't a strategic tech acquisition. This was a founder buying his own name.

For M. Darren Root, owning Root.com was personal branding at its finest. A CPA firm with the exact-match domain had instant credibility and memorability. While we don't know what M. Darren Root paid for the domain in 2004, it was likely a significant sum even then—single-word .com domains were already valuable by the mid-2000s.

The CPA firm held onto Root.com for nearly 18 years, from 2004 to 2022. That's an unusually long hold period for a premium domain, suggesting the business was stable and saw no reason to sell.

2022: The Insurance Match

In early 2022, Root.com was sold again—this time to Root, Inc., an insurance company founded in 2015.

Root insurance is a tech-forward car insurance startup that uses telematics (smartphone sensors) to determine rates based on actual driving behavior. The company went public via SPAC in 2020 and needed a domain that matched its simple, powerful brand.

Root, Inc. had been operating on JoinRoot.com since its founding in 2015. While functional, JoinRoot.com lacked the authority and simplicity of Root.com. For a company competing against giants like Geico and Progressive, the exact-match domain was worth the investment.

In March 2022, Root, Inc. acquired Root.com and began forwarding it to JoinRoot.com.

The $1.3M Discovery

So how much did Root insurance pay for Root.com?

For years, the answer was unknown. Domain sales between private parties are rarely disclosed publicly, and Root, Inc. never announced the acquisition in a press release.

But DomainGang, a domain industry news site, dug into Root, Inc.'s SEC filings and found the answer buried in financial statements:

"In March 2022, we purchased the Root.com domain and recognized $1.3 million, including transaction costs, as of December 31, 2022 in other assets in our consolidated balance sheets."

There it was: Root.com sold for $1.3 million.

The discovery came after DomainGang received a mailer from Root insurance that included the Root.com domain, prompting them to investigate when and how the insurance company acquired the domain. Their research uncovered a seven-figure sale that had gone completely unnoticed by the domain industry.

Why $1.3M Made Sense

At first glance, $1.3 million might seem expensive for a domain that Root, Inc. is simply forwarding to JoinRoot.com.

But the price makes sense for several reasons:

1. Single-Word .com Premium

Root.com is a single-word, dictionary-term .com domain. These are among the most valuable domains on the internet. Comparable sales from around the same period:

• Jump.com: $7.5M (2021)
• Voice.com: $30M (2019)
• Poshmark.com: $175K (2011, much earlier)

In the context of single-word .com domains, $1.3M was a reasonable price—perhaps even a bargain.

2. Brand Authority

Root insurance operates in a crowded market against established players with decades of brand recognition. Owning Root.com gives the company:

• Instant credibility: The exact-match domain signals permanence and authority
• Easier marketing: "Go to Root.com" is simpler than "Go to JoinRoot.com"
• Email addresses: [name]@root.com looks more professional than [name]@joinroot.com
• Future flexibility: If they ever want to rebrand away from "JoinRoot," they already own the perfect destination

3. Public Company Optics

Root, Inc. went public in 2020. For a publicly traded company competing in insurance, owning the exact-match domain is a signal to investors, partners, and customers that the company is serious about its brand.

The $1.3M expense was also a rounding error in Root's financials—the company had raised hundreds of millions in funding and reported hundreds of millions in revenue by 2022.

The 30-Year Journey

From 1994 to 2022, Root.com had a journey that mirrors the evolution of the internet itself:

• 1994-1999: Registered for free by a Unix pioneer
• 1999-2001: Used to promote open-source software (FreeBSD)
• 2001-2004: Supported commercial tech infrastructure companies
• 2004-2022: Owned by a CPA firm with the matching surname
• 2022-present: Acquired by a tech-forward insurance company for $1.3M

Each owner used Root.com in a way that fit their needs:

• David Greenman used it for technical credibility in the Unix community
• M. Darren Root used it for personal brand alignment
• Root, Inc. uses it for corporate brand authority

The domain's value compounded over time, from $0 in 1994 to $1.3 million in 2022—a reminder that premium domains appreciate like real estate.

The DomainGang Investigation

This story only exists because of investigative work by DomainGang.com.

When DomainGang received a promotional mailer from Root insurance that included the Root.com domain, they noticed something: the company had been using JoinRoot.com for years. When did they get Root.com?

DomainGang searched WHOIS records, archive.org snapshots, and social media mentions. They found that Root.com started forwarding to JoinRoot.com in March 2022, but the acquisition price wasn't public.

Then they dug into Root, Inc.'s SEC filings—the quarterly and annual financial reports that publicly traded companies must file. Buried in the "other assets" line item of the consolidated balance sheet was this note:

"In March 2022, we purchased the Root.com domain and recognized $1.3 million, including transaction costs..."

Most domain sales are never disclosed. But public companies have to report material acquisitions, and $1.3M was significant enough to appear in Root, Inc.'s filings.

DomainGang's research uncovered a seven-figure sale that would have otherwise remained hidden. It's a reminder that some of the most interesting domain stories require digging through SEC filings, WHOIS history, and archive.org captures to piece together.

The Keyword Domain Playbook

Root.com's story illustrates the enduring value of keyword domains.

"Root" is a foundational term in computing, finance (root cause), botany (root system), and general language (getting to the root of something). It's a word everyone understands, with strong associations across multiple industries.

For Root, Inc., owning Root.com wasn't just about matching the brand—it was about owning a word that conveys foundation, origin, and trust. In insurance, where trust is everything, that association matters.

Keyword domains like Root.com don't age. They don't go out of style. They remain valuable decade after decade because the words themselves remain foundational.

The Forward vs. Rebrand Question

One interesting detail: Root, Inc. is forwarding Root.com to JoinRoot.com, not using it as the primary domain.

This raises a question: why not rebrand entirely to Root.com?

There are a few possible reasons:

1. Brand equity: JoinRoot.com has been the company's domain since 2015. Seven years of marketing, SEO, and customer recognition is valuable.
2. Technical complexity: Migrating email, internal systems, and integrations from JoinRoot.com to Root.com is a large undertaking.
3. Future strategy: Root may be planning a gradual migration, starting with the forward and eventually making Root.com the primary domain.

Either way, owning Root.com gives the company optionality. They can rebrand when it makes sense, or simply benefit from the SEO and type-in traffic that Root.com generates.

The Takeaway: Free to $1.3M

Root.com's journey from a free 1994 registration to a $1.3 million acquisition in 2022 is a 30-year case study in domain value appreciation.

The domain has served:

• A Unix co-founder promoting open-source software
• Tech infrastructure companies
• A CPA firm with the matching surname
• A publicly traded insurance startup

Each owner extracted value from the domain in different ways. And each sale increased the price.

Root.com is now in the hands of Root, Inc., where it will likely stay for years—or decades—to come. The company has the exact-match domain, the brand alignment, and the capital to hold it forever.

For a domain that started at $0 in 1994, $1.3 million in 2022 is a reminder: premium domains don't depreciate. They compound.

And sometimes, the best domain stories are hiding in SEC filings, waiting for someone to dig them up.

Research credit: DomainGang.com for uncovering the Root.com acquisition details through SEC filings.