Current Initiatives
Project Invisible Ladder
Project Invisible Ladder
Project Invisible Ladder
Most small business owners in Appalachia don’t fail for lack of grit—they fail because no one ever showed them the rungs. The skills, systems, and connections that make success easier are often hidden, passed quietly from one insider to another.
Project Invisible Ladder is our behind-the-scenes effort to uncover those hidden rungs and put
Most small business owners in Appalachia don’t fail for lack of grit—they fail because no one ever showed them the rungs. The skills, systems, and connections that make success easier are often hidden, passed quietly from one insider to another.
Project Invisible Ladder is our behind-the-scenes effort to uncover those hidden rungs and put them within reach for every entrepreneur in Appalachia. Every project begins inside Invisible Ladder.
The first visible rung is Main Street MBA: Teen Edition—a 12-month, hands-on training program that lets small business owners put their own teenagers on payroll, save thousands in taxes, and equip their kids with real-world skills that belong on a résumé and fit beautifully in a college admissions essay!
Tom Grayscale
Project Invisible Ladder
Project Invisible Ladder
Modernizing small businesses for long lasting success requires the use of AI. There's no way around it. At Deep Rooted, we built our own AI Agent, Tom Grayscale. He's the AI brain we unleash on all the messy, outdated, overly complicated parts of running a business. He's reviewed thousands of Appalachian small business websites. He genera
Modernizing small businesses for long lasting success requires the use of AI. There's no way around it. At Deep Rooted, we built our own AI Agent, Tom Grayscale. He's the AI brain we unleash on all the messy, outdated, overly complicated parts of running a business. He's reviewed thousands of Appalachian small business websites. He generally works while we sleep, gives us analysis that doesn’t sugarcoat, and he definitely doesn’t tolerate “that’s just how we’ve always done it.”
From forgotten software subscriptions to customer flows that feel like obstacle courses, Tom finds the fix and serves it with a side of sass. He enjoys teaching and occassionally writes a blog for us. Think of him as your digital operations whisperer — minus the whispering. We hope you like brutal honesty; it's how we trained him to communicate and the no fluff approach has led us down some wonderfully rich paths of thought.
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Project Tall Oak
Project Invisible Ladder
Project Tall Oak
Project Tall Oak is our ever evolving plan to deliver solutions to Appalachia, all 423 counties across 13 states. Out first Tall Oak is Bristol, TN/VA to test our hyper local business tools to businesses across the Tri-Cities. In 2026, we'll be expanding our footprint across Appalachia's South Central Region (Virginia, Tennessee and Nort
Project Tall Oak is our ever evolving plan to deliver solutions to Appalachia, all 423 counties across 13 states. Out first Tall Oak is Bristol, TN/VA to test our hyper local business tools to businesses across the Tri-Cities. In 2026, we'll be expanding our footprint across Appalachia's South Central Region (Virginia, Tennessee and North Carolina). By mid year, we'll launch another Tall Oak in Pennsylvania to reach Appalachia's North Region (Northeast Ohio, Southern New York, a small piece of Maryland and the majority of Pennsylvania).
We are currently developing strategic partnerships in Pittsburgh for a large, high-impact financial project that, if we can pull it off, will change everything. We're calling it Project Switchback.
Operational Clarity for Local Prosperity
Deep Rooted Future Foundation is structured as a nonprofit — a regional think tank and community intelligence hub.
It listens to the voices of Appalachian business owners, gathers and maps their most pressing challenges, and asks bold, imaginative questions: What if there were a better way? What if the tools fit the people?
Closely aligned with Deep Rooted is Main Street Intelligence — a software design and deployment trategy firm focused on making those ideas real and delivering them to Appalachia. It turns insight into action, designing smart, practical systems that small businesses can implement for Rooted and MSI work hand-in-hand with a shared mission: to empower small and mid-sized businesses across Appalachia by transforming pain points into progress.
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