Our Story
Built by
an attorney, for attorneys.
Attorneys spend countless hours repeating the same explanations in contracts and estate planning documents — slowing down client understanding and draining valuable time.
Founder Elliott Stapleton, an experienced estate attorney, faced this daily. One day in 2020, after explaining the same complex clause to three different clients in a single afternoon, he realized there had to be a better way.
That moment sparked Explain Once: a tool to clarify legal language instantly, so attorneys save time and clients gain confidence.
Elliott envisioned a way to embed plain-language explanations directly inside Word documents — giving clients clarity before questions even arose.
Finding no solution on the market, he partnered with developers to build one. The result: a tool that streamlined communication, improved client satisfaction, and saved attorneys hundreds of hours each year.
What began as an in-house solution quickly proved invaluable, enabling Elliott to scale his practice and paving the way for Explain Once.
From Frustration to Innovation
Strategic Advisor & Founder
Elliott Stapleton Esq.
Elliott is the creator of Explain Once and a seasoned attorney with a background in estate planning. With 17 years of experience, Elliott built his legal career on precision, efficiency, and a commitment to delivering exceptional client service.
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Motivated by a drive to cure inefficiencies in client communication, he developed Explain Once as an in-house solution. Between 2020 and 2024, Elliott used the software to help double the size of his practice, positioning it for a successful sale.
As an advisor to the Explain Once team, Elliott is dedicated to helping other professionals enhance their workflows and deliver greater value to their clients through efficiency.
Michael serves as CEO and Co-Founder of Explain Once, where he leads company strategy, product development, and operations. A former Software Engineering Manager with an MBA in Information Systems, he brings deep experience in scaling technology solutions that solve real-world business challenges and bridging the gap between technology and business outcomes.
At Explain Once, he guides the product from MVP through market validation and growth while ensuring the platform delivers measurable value to customers.
Driven by a philosophy of building fast, lean, and customer-focused solutions, he is dedicated to building Explain Once into a company that helps organizations save time, simplify processes, and operate more effectively.
Michael Stadtmiller
CEO & Co-Founder
Advisor & Founder
Ryan Rodriguez
Product and Sales Manager
& Co-Founder
As a co-founder and Product and Sales Manager of Explain Once, Ryan focuses on sales acquisition, product management, and strategic development.
Driven by a commitment to saving users time and delivering immediate value, he is dedicated to ensuring the product exceeds expectations from day one.
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Ryan served as a Naval Officer with nine years of experience flying jet aircraft, where he honed his precision, discipline, and ability to tackle complex challenges. His MBA studies focus on Digital Technology Management; he is passionate about creating innovative solutions prioritizing customer needs.
Leon is a seasoned software engineer with a passion for building high-performance applications that solve complex problems.
With over two decades of experience in software architecture, AI integrations, and enterprise application development, he’s worked across industries—from cybersecurity to telephony to IoT.
He started his career as an Aeronautical Engineer and Air Force Officer before diving deep into software development, launching Gravity Storm Software, LLC, the first Security Patch Management software for enterprise networks.​ Leon has since developed and delivered 100+ commercial software products, leading projects in AI, cloud computing, and Microsoft Office integrations.
He’s a master of C#, .NET, and cloud-based AI services, with expertise in RAG (Retrieval Augmented Generation), speech-to-text, and GPT-powered applications.
