AI Leadership & Perspective

I started an AI company that creates lesson plans for teachers – here are the biggest learning lessons I’ve faced when getting Chalkie off the ground

By Phillip Daneshyar

When we started working on Chalkie, the vision was straightforward: simplify life for teachers. Educators spend countless hours crafting lesson plans, customizing materials for diverse learners, and navigating ever-changing curriculum demands. We saw an opportunity for AI to ease that workload. What we didn’t fully expect was how much we would learn from teachers themselves, and how those insights would shape everything we do. 

One of the most memorable moments came during our beta launch. We invited about 50 to 100 teachers from our personal and professional networks to try the platform and give feedback. The response was incredible, teachers quickly began incorporating Chalkie into their daily routines. But what stood out most was what happened next. 

Without any marketing or outreach, teachers outside the beta group started signing up and even paying for the platform. At first, we couldn’t figure out how they’d heard about us. Then it became clear: teachers in the beta had been sharing Chalkie online, showcasing how they were using it in their classrooms, and recommending it to others. This organic word-of-mouth growth brought us our first 200 paying users and was a powerful reminder: when you create something genuinely useful, your users often become your best advocates. 

Another key takeaway came from seeing the many ways teachers used Chalkie. We originally designed it to help create curriculum-aligned lessons and classroom materials. But as more educators joined, we saw them using it in unexpected ways like adapting lessons for students with varying needs and building entirely new resources we didn’t know the platform could make! 

While this was exciting, it also brought challenges. With so many feature requests, prioritizing became tricky. The only way to navigate this was by staying close to our users and listening to their needs, asking questions, and understanding the deeper reasons behind their requests. That “why” became central to how we set our priorities. 

For anyone building a product, the best advice is to launch quickly and keep iterating. It’s easy to spend months perfecting an idea, but nothing accelerates progress like real-world feedback. You might find that the problem you’re solving isn’t as critical as you thought, or that your approach needs adjustment which isn’t failure; it’s part of the process. The sooner you learn, the sooner you can improve. 

Y Combinator’s philosophy had a big impact on how we approached Chalkie. One of their core principles is simple: build something people want. In today’s world, you can create almost anything with the right tools. The hard part isn’t building but solving a real, meaningful problem.  

Reflecting on Chalkie’s journey so far, the biggest lesson is this: successful startups don’t happen because founders have all the answers. They happen because founders are willing to listen, learn, and adapt based on the needs of their users. For us, those users are teachers and they continue to guide everything we do.   

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