Doist

Amir Salihefendic, a developer, created Todoist in 2007 purely out of personal necessity—he needed a to-do list and wanted to avoid paying for server costs. He launched with a simple monetization strategy: make reminders a paid feature. Within the first couple of months of 2007, he had his first paying customer, acquired through his popular blog (mix.decay). This wasn't a grand vision to disrupt productivity; it was a pragmatic side project built while Amir was simultaneously co-founding a social network (2007-2010).

When the social network failed, Amir returned to Todoist full-time. By the end of 2007, the bootstrapped tool was generating "a few thousand bucks per month in profit" with over 200 customers—all while Amir single-handedly handled development, support, marketing, and design. Growth was organic and steady but flat until 2011, when he hired his first employee. The team grew slowly: by 2012-2013, native mobile apps launched, and by 2015, the company had reached 40-50 people. However, this growth masked dysfunction.

From 2015-2018, Doist hit a wall. Despite hiring aggressively, productivity plummeted. "We didn't ship anything," Amir recalls. The culprits: technical debt from a side-project codebase, a failed experiment with no-hierarchy management, and lack of organizational structure. Meanwhile, customer growth accelerated dramatically after the mobile app launch—the company passed 10,000 customers around 2012-2013 and 100,000 by 2015-2016. Todoist's freemium model meant a ruthless focus: $5/month premium pricing, a few-percentage conversion rate from free to paid, and brutal annual churn of ~70% (20-month LTV at $100). Amir remained zen about this, philosophically accepting that not every user would stick.

In 2019, Doist finished at ~$10M ARR. By the time of this interview, they'd grown to $14M ARR with plans to hit $20M next year—all bootstrapped, profitable, and fully remote since day one. The company now has 85-90 employees, 50 of them engineers, zero salespeople. Amir recently introduced employee stock options (25% pool) despite his initial skepticism, wanting to reward long-tenured team members. He's also building Twist, an asynchronous communication tool generating $600K annually. His next frontier: cracking multiplayer features to increase lifetime value and position Todoist as a collaboration tool, not just an individual productivity app. When asked about acquisition offers, Amir was blunt: he declines them without entertaining numbers. This is his life's work, and his goal is $100M in revenue within five years.