Building Avery: A Year of Lessons

The Problem

Most task apps require you to manage them. You have to open the app, set the reminder, check things off. It’s ironic—if you’re already struggling to stay organized, the last thing you need is another tool demanding more of your attention.

That gap between intention and action was the itch I couldn’t shake.

Early Attempts

I tinkered with versions of Avery long before the recent AI wave, using more traditional approaches. It worked to a point, but it never felt like the leap forward I needed. Then the new generation of large language models arrived, and suddenly it seemed possible. A year ago, I decided to really build it.

What Went Wrong (and Right)

The first few months were all about speed: get something working, see if it sticks. I got messaging and a simple task system running quickly. It worked, but not reliably enough to be something people could depend on.

So I hit reset. I stripped away overcomplicated experiments and rebuilt Avery around a solid foundation: WhatsApp for communication, a smarter task engine that could handle recurring reminders, and a focus on timing and context.

Along the way, I learned that:

Mature, well-documented libraries are your best friend. AI thrives on good documentation.
“Simple” features—like detecting the right time to nudge you—are anything but simple.
Reliability matters more than cleverness. A feature that works 95% of the time is better than one that dazzles… half the time.

Launching for Real

Eventually Avery became more than a prototype. She could send proactive reminders, break down recurring tasks, sync with calendars, and even use context—like day of the week or recent activity—to reach out at the right moment.

I launched quietly. No big announcements, just a soft release to see what would happen. To my surprise, the first paying customer came in quickly. That was the moment it felt real. Not “done,” but real.

What I’m Learning Now

The past year hasn’t been smooth. I’ve had production issues, scrapped features that sounded brilliant in theory, and navigated the usual founder mix of excitement and panic. I’ve also seen people start using Avery in ways I didn’t predict—talking to her, not just about tasks, but as a conversational companion that helps them think.

That’s the spark that keeps me building.

Closing Thoughts

Avery isn’t another productivity app. She’s a different way of closing the gap between “I should do this” and actually doing it.

It’s still early days, but if you’ve ever felt like task apps don’t stick—or that your brain works more in conversations than in lists—you might get something out of Avery too.