WorkFlowy

In 2008, Jesse Patel was drowning in complexity. Working on business development for a nonprofit tech company with 4 million active users, he was tasked with exploring 30 different monetization avenues simultaneously. Cycling through traditional to-do apps and project management tools, nothing could handle the hierarchical, fractal nature of his work. He found himself gravitating toward Word's outline mode—it was close, but it needed something crucial: the ability to zoom in and focus on specific sections without losing the broader context. This was the insight that would become WorkFlowy.

Jesse, self-taught in code since his days at Stanford, decided to use this idea as his learning-to-code project. "Everyone thinks they can make a better note-taking app," he reasoned, "so I'll just waste this idea on learning to program." Starting in 2008 with minimal technical skills, he built a prototype with a columns-based interface inspired by the Mac Finder. The first version bore little resemblance to the outline tool that would later captivate users—it was unconventional, but it worked for him.

In October 2009, burned out and convinced the nonprofit's business models wouldn't work, Jesse quit his job to go full-time on WorkFlowy. For the next four months, he worked solidly on the product. Remarkably, one of his earliest real users was Shafka Nusrulla, who would go on to found NewsCred. Shafka used that early columns version as his personal project management system—the only person ever to use that iteration seriously.

By early 2010, Jesse had something he loved using himself, but he was starting to lose momentum. Reading Navel Ravikant's Venture Hacks and essays from other founders, he kept seeing the same advice: find a co-founder or go insane. Jesse reached out to two technical friends in December 2009. One was already starting something else, but the other was Mike MacGirvin, a college dorm-mate who had recently left Google.

Mike wasn't interested in WorkFlowy initially. He found the note-taking space saturated and wasn't excited about another productivity tool. Instead, they brainstormed a different idea: an app to help self-help authors and gurus package their advice for followers. It felt like a safer bet. They decided to apply to Y Combinator together with this new concept.

By the time they entered Y Combinator's Summer 2010 batch, Jesse had moved back to San Francisco to be near Mike. The partnership was supposed to be on the "self-help guru" product, but during their time in the accelerator, everything shifted. Paul Graham was characteristically frank during office hours: "I've seen a million online collaborative whiteboards. This is not going to go anywhere," he told them about the guru platform. The feedback stung, but it was clarifying.

Meanwhile, a few other YC founders had started using WorkFlowy and kept giving Jesse feedback about what they loved and what annoyed them. Mike, exposed to the tool through the workspace, began to see what made it different. Jesse lobbied hard for a pivot. "We were floundering around, playing with Facebook apps," he recalls. "Once Mike started using WorkFlowy himself and saw how it was actually cool and different, he came around."

Their pivot was so unconventional that they didn't even tell Y Combinator until demo day. "Everyone in YC was like, 'We've never heard of that before,'" Jesse remembers. The reaction wasn't upset—it was relief. At least they were working on something real.

When WorkFlowy launched publicly after YC, the impact was immediate. Tech Crunch and Lifehacker covered it. On day one, 10,000 people signed up. Critically, unlike their previous small user base, these users didn't stop using the product. They had an 11-hour daily average usage and retention that would become the company's defining advantage. The high-retention users became natural advocates, and word-of-mouth started its own flywheel: people saw WorkFlowy over someone's shoulder, got curious, and tried it themselves.

Jesse and Mike made a deliberate choice not to raise venture capital. After YC, they talked to some investors for a few weeks, but no one was interested in a weird, hard-to-explain productivity tool without massive traction. Rather than chase funding, they decided they didn't want it anyway. "I don't like authority," Jesse explains. "I don't like the idea of having bosses who aren't me."

But the first few years were financially precarious. Jesse had spent all his savings on rent. Mike had stock from Google and didn't feel the pressure. For two years after launch, they didn't charge users—a decision that created tension in the relationship. Jesse kept bringing it up; Mike deprioritized it. The issue festered in silence until finally, Mike didn't realize Jesse had literally spent all his money. When they did eventually add a paid tier in 2012, they took a humble approach: setting a free quota of 500 bullets per month and emailing heavy users asking them to pay. On day one, nearly 30% of those users signed up for the paid plan.

The biggest lesson from those early years was about co-founder relationships. Jesse and Mike had very different working styles. Jesse is impulsive and extroverted; Mike is deliberate and needs deep focus. Jesse wanted to pair program and brainstorm constantly; Mike wanted to think alone and execute. These tensions festered until a walk to Dolores Park where Mike said, "I don't think I can do this anymore." They started therapy—actual couples therapy—and addressed the underlying issues. The tools they learned stuck with them: weekly check-ins about what's bothering each of you, addressing small issues before they become rifts.

Today, WorkFlowy generates approximately $800,000 in annual recurring revenue with over 100,000 active users, all built by just two people until recently. Users stay for an average of three years. They've grown entirely through word-of-mouth, never spending a dollar on marketing or ads. As Jesse puts it: "We've been very lucky in that the business has supported our pretty laissez-faire and lazy approach. It's entirely product-oriented."

About a year ago, after taking time off to raise twins, Jesse felt a renewed sense of purpose. WorkFlowy, he realized, is only capturing a fraction of its potential. "There's this whole other angle," he explains. "I know there's just a lot of people for whom it could be a very important part of their lives." The evidence is overwhelming: 20,000 new signups every month from word-of-mouth alone, but only about 5% convert to long-term users because the onboarding experience is confusing.

They've started hiring—three full-time employees now plus contractors—to finally realize WorkFlowy's vision. Key priorities include mobile redesign (the feature gap between mobile and desktop is enormous), better collaboration for teams, dates and reminders, and most importantly, fixing the new user experience so that fewer than half of signups fail to create their first bullet point. Jesse's motivation is that of a craftsperson: not to make money or go viral, but to build what this tool could truly be.