Founder: Steven Hannah 

Location: Turner, ME

Year founded: 2025

What inspired you to start this company? 

My 13-year-old daughter is neurodivergent, and despite being a smart kid, she struggles in school. About two years ago, she was diagnosed with dyslexia, dysgraphia, and ADHD, but even with the diagnosis, getting her the accommodations she needed in school proved a struggle.  As we dove into our situation, we found a huge network of parents dealing with very similar issues.

What did the earliest version of the business look like? 

The earliest version of our business was just a stand-alone app to help our daughter with spelling and reading.  We took the advice of her neurologist combined with some research and study on our own part to give her something that could help her.  From there, we found several other families that used a copy of the software for the remainder of the school year and got significant benefit.

What problem are you trying to solve, and for whom? 

The middle school transition overwhelms neurodivergent students’ existing compensation strategies, as increased demands for abstract thinking, executive function, and reading comprehension, causing capable students to fall behind, requiring remediation that schools are not equipped or funded sufficiently to deliver, resulting in long-term damage to academic confidence.

Why hasn’t this problem been solved well before? 

Improved detection and testing has increased the population of students needing accommodations, but schools have not been structured or funded to deliver unique learning options to individual students. The biggest blocker to solving this problem, though, has been the entrenched educational paradigm that has treated these challenges as skill deficits requiring more practice and effort, rather than as differences in information processing requiring different tools and approaches.  

What does your company do to solve this problem? 

Osage Learning applies real-time accommodations to students’ existing workload, refactoring reading and math content so students can process information effectively. Because different students need different accommodations, we put all accommodation options directly in students’ hands, allowing them to discover and apply what works for them without asking permission or calling attention to themselves. This builds both autonomy and self-advocacy skills.

What makes your solution different or better than alternatives? 

Existing solutions fall into two camps: more practice (tutoring, remediation, skill drills) or complete workarounds (text-to-speech that eliminates reading entirely). The first overwhelms students who already struggle with executive function and attention. The second bypasses skill development altogether. It’s the Goldilocks problem where adaptive learning tools either demand too much or too little, rarely hitting the middle ground where students can engage with the actual skill while receiving the accommodations they need to succeed.

Who are your customers today? 

Our primary customers are parents of middle and high school students with learning differences like dyslexia, ADHD, and dyscalculia. We partner with schools and districts to connect with families, creating a scalable alternative to the one-on-one interventions schools struggle to fund and deliver.

What’s the most important thing you’ve learned from talking to customers? 

Watching students use early prototypes, we saw how fear of being wrong made them hesitant. We learned to balance necessary skill feedback with judgment-free exploration. When students discover their own processing strategies, like highlighting patterns, we make it exploratory, not prescriptive. The goal is rebuilding confidence through self-discovery, not just correct answers.

What assumption turned out to be wrong early on? 

We initially assumed spelling would be our first module because it is a common struggle for dyslexic students, and we thought it would deliver high value quickly. After talking to 30 families, every single one prioritized reading comprehension instead. When we dug deeper, we learned that by middle school, spelling has largely disappeared from the curriculum. That insight shifted our entire product roadmap to focus on the skills students actually need to succeed in middle and high school.

What progress are you most proud of so far? 

We’re most proud of seeing real impact with real students. Our own daughter uses Osage Learning daily, and the difference between this year’s work and last year’s is amazing. It’s not some kind of miraculous transformation, but consistent progress. Homework that used to end in frustration now gets done. She’s engaging with challenging content and building confidence. Watching her and our early users succeed with grade-level work they couldn’t access before validates everything we’re building.

How did participating in Dirigo Labs support your growth? 

Dirigo Labs connected us with experienced founders who had faced similar challenges. That peer learning has been invaluable. The accelerator is now pushing us beyond product development to focus on go-to-market strategy, financial modeling, and what scaling actually requires. It’s forcing us to think like business operators, not just product builders, because impact at scale requires business success, not just a good product.

Where do you see the company heading in the next 6–12 months? 

Our focus is twofold: growth and impact. Our goal is for Osage Learning to reach over 100 families by year-end while deepening community connections within our user base. Parents and students need more than software. They need peer support and shared strategies. We’re exploring forums, virtual meetups, and ways for families to learn from each other’s experiences. Strong community creates both better outcomes for students and organic awareness that drives growth.    

What’s the biggest challenge you’re working through right now? 

Brand awareness. Our target customers are parents of neurodivergent middle and high schoolers. They aren’t actively searching for solutions like ours because they don’t know they exist. We’re working to identify the communities and channels where these families naturally gather and figure out how to authentically show up there.

What kind of help would be most valuable right now? 

Marketing and brand awareness are paramount. We need to make progress in two main areas: ideation of how to reach families thus converting awareness into paying customers, and connections who can open doors to the communities, schools, and organizations where those families already are. 

How can the Maine startup community support you? 

From a prescriptive standpoint, connections are the biggest thing.  Whether someone says “Oh, I know a family who has a dyslexic child.  Maybe they’re interested in hearing about this” or they know an administrator or teacher at a school that is struggling under the burden of IEPs and 504 Plans, making that connection to help us build awareness and brand will be the single act that makes the biggest difference for us.

But more broadly, entrepreneurship is a lonely endeavor, and one that most of us get into because we want to make a meaningful difference.  I think the ability to be in a community that acts like a community is a rare find in this journey. So the mere fact that the community is accessible, approachable, and open already provides a large bump in support.

Best way for people to reach you: 

Email: steve@osagelearning.com

Phone: 240-622-4335