About
Built by
an attorney, for attorneys.
Explain Once was born out of a common frustration faced by attorneys: the time-consuming, repetitive task of explaining basic legal concepts again and again.
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For founder Elliott Stapleton, a seasoned estate attorney, this challenge came to a head one day in 2020 after explaining the rule against perpetuities section of a revocable trust to three different clients - all in a single day.
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He realized there had to be a better, more efficient way to clarify legal language and improve client satisfaction.
Elliott wanted to automatically embed his explanations in line with the text of the estate planning Word documents to answer clients' questions before they were asked.
After exploring the market and finding no solutions, Elliott hired a programmer to develop an in-house software solution to achieve this goal.
This solution streamlined client communication, boosted client satisfaction, and saved approximately 200 hours yearly.
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The efficiencies created by this tool allowed Elliott to scale his business and position it for a successful sale. ​​
From idea to solution.
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.
Ryan Rodriguez
Product and Sales Manager & Co-Founder
As a co-founder 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.
Neil Mattis
Senior Solutions Manager
With a strong background in consultative strategy, he has worked closely with clients across industries to identify pain points and deliver technology that simplifies complex processes. His ability to bridge the gap between technical solutions and business needs makes him a valuable resource for professionals looking to optimize their workflow.
From his MBA studies, Neil brings a deep understanding of how organizations can position themselves for sustained growth. His expertise extends beyond product implementation—helping clients think strategically about efficiency, scalability, and long-term value. He believes that the right tools, paired with the right approach, can transform the way professionals engage with their work and their clients.
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At Explain Once, Neil is committed to empowering professionals with solutions that simplify communication and improve productivity. He takes pride in providing a product that helps users save time, enhance client interactions, and stay ahead in a competitive landscape.
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.
