Rightly

Sam Schalache and his co-founders—including Steve Schalache who had built FullWrite, a word processor that competed with Word 1.0—noticed two emerging browser capabilities: content editable and JavaScript. In October 2005, they decided to experiment with building a word processor in the browser, not as a grand vision but as a simple exploration. "We just decided to try it," Sam recalls. "Like, what's it like to build a word processor in the browser?" The team was armed with deep domain expertise in both application building and word processors, yet they were pessimistic about the browser's capabilities. Sam overruled their concerns, proposing a rapid experiment that took only a couple of days to get running.

The first breakthrough came almost accidentally. As Sam and his co-founders typed in the same document simultaneously without any locking mechanism in place, they discovered something magical: real-time collaboration. "We immediately realized this was really cool," Sam says. "We could both work in the same document at the same time." But they also immediately realized the hard problem: collision detection and managing concurrent edits. What followed was years of engineering work. Operating transform techniques hadn't been invented yet, so they built a three-way merge system—a gnarly problem because HTML documents don't have a canonical representation. Firefox and IE rendered blank paragraphs differently; attributes could reorder; the DOM tree itself could differ. "It was a really hard merge problem," Sam admits. Yet they stayed motivated because they'd glimpsed the "what if"—the vision of collaboration—before understanding the complexity.

The team decided to test whether they could build a subscription business by advertising on Google to measure customer acquisition costs. This simple marketing move got them noticed. They became one of the earliest TechCrunch features (Michael Arrington was deciding between covering them or focusing on his blog at the time). The launch created enormous momentum. "We got noticed like we were the hot thing for a couple months," Sam recalls. VCs flooded in. They recognized that after Gmail came as the first point on the curve showing web-based Google applications, Rightly was the second point—one that proved real, complex apps could run in the browser. The implications were clear to the market: if documents could work, why not the entire Office suite?

The product's simplicity was intentional and powerful. Rightly required no email at first—no friction, no signup, just open and type. After two minutes, if users were still engaged, a gentle prompt asked for an email so they could retrieve the document later. This minimalist approach contrasted sharply with Microsoft Office's thousand-button complexity. By making a trade-off—giving up most advanced features in exchange for zero-install convenience and real-time collaboration—Rightly solved a real problem people didn't know they had.

Sam spent significant energy on offline editing, which "never turned out to matter that much." Other early priorities, like supporting complex formatting and pagination, proved less critical than expected. Word count came up repeatedly from students writing essays—a signal Sam hadn't anticipated. The lesson: you have to put it in front of people to learn what truly matters.

Google acquired Rightly, and Sam brought the core team and product to Google. The migration story is telling: they put Gmail into maintenance mode for eight hours on a Sunday, migrated all data to Google infrastructure, and brought the new system online. Three days later, when Sergey Brin asked when they'd move to Google infrastructure, Sam got to say: "Oh yeah, we did it this weekend. No one noticed." Only a blogger in Germany caught the IP address change.

Today, Google Docs has over 1 billion active monthly users and has fundamentally changed how the world creates documents. Sam has moved on to Microsoft as a Corporate Vice President, but the lessons from Rightly—about optimism, rapid experimentation, understanding user laziness, and the power of the "what if" question—continue to shape his approach to disruptive innovation in AI and beyond.