The Business Duck

Don Reynolds

I am a tech-forward, business-minded builder who believes, with Socrates, that the only good is knowledge and the only evil is ignorance. My work centers on learning, teaching, and using evidence to challenge assumptions. I design systems that help people do more with less friction, and I focus on small business because it is one of the strongest tools we have for individual empowerment. I write about judgment, technology, and practice at Philosophy Duck: https://substack.com/@philosophyduck

Don Reynolds

Business Philosophy

Evidence over ego. Clear reasoning over comfortable stories. I look for disconfirming data, share what I learn, and build processes that others can follow long after I leave. I am optimistic about new technology and practical about how to apply it. AI and automation are levers to create measurable value for individuals, teams, and communities. I am a committed advocate for individual liberty, empowerment, and equality. I have deep experience working with LGBTQ communities in both professional and volunteer settings and work to make sure that everyone, regardless of creed or identity, has a part in the American Dream.

Experience

Product, operations, and compliance leadership

Over more than a decade at At Your Pace Online (AYPO) and Certus, I built teams, shipped software, and scaled regulated education products.

Certus (American Safety Council). Compliance Manager overseeing thousands of courses and many thousands of agency relationships. I negotiated complex approvals, aligned systems with evolving rules, and kept large portfolios audit-ready.

AYPO. Program Director, then Chief Operations Officer, then Software Product Designer and Program Manager. I grew the writing organization from 2 to 15, expanded content into more than 600 markets with over 1,000 courses, and helped the company reach about 8 million dollars ARR with eight consecutive years of double-digit growth. I led the design of a custom LMS and a content platform that cut production time from weeks to hours, created clear KPIs and incentive structures, and partnered with marketing on ROI-driven roadmaps. AYPO was acquired in an eight-figure deal.

Founding and consulting

I have helped launch two companies and consult with founders on the path from idea to execution.

  • Rogue Party Bus. Guided the founder from concept to market leader in the Rogue Valley, including licensing, hiring, pricing, and a high-visibility launch strategy. The business reached breakeven in 18 months and profitability within two years.
  • Two Goats Sewing Repair. Helped shape the business plan and go-to-market for a mobile sewing machine repair service in Southern Oregon.
  • Independent consulting. Ongoing work in business planning, regulatory strategy, and operational design for small businesses.

Community leadership in the SCA

I have spent a decade as an officer in the Society for Creative Anachronism, serving communities that value craft, discipline, and service.

  • An Tir. Kingdom Cut and Thrust Marshal (safety officer) for three years, serving a kingdom with more than 2,000 paid members. Designed and launched a digital authorization system that reduced processing times from weeks to minutes and now supports thousands of users.
  • Summits. Seneschal, the executive role for a principality of about 500 members. Led operations, governance, and policy implementation across the region.
  • Honors. Member of the Order of Defense for mastery in sword fighting, and Member of the Order of the Pelican for exceptional service to the community.

Military service

Oregon Army National Guard, 2002 to 2008. Deployed to Afghanistan as an infantry soldier. The experience grounded my approach to leadership, logistics, and accountability.

Achievements

  • Grew AYPO to about 8 million dollars ARR, expanded into 600 plus markets, and produced 1,000 plus online courses while sustaining double-digit annual growth for eight years, contributing to an eight-figure acquisition.
  • Designed a custom LMS that met complex legal requirements across hundreds of markets and improved student experience and developer velocity.
  • Built a content platform that automated publishing and cut production time by about 5x, with immediate live-update capability.
  • Led the Texas real estate pre-license program to top-five statewide performance, generating over 2 million dollars ARR and creating a custom online proctoring solution with 400 percent ROI that later unlocked adjacent markets.
  • Launched the An Tir authorization web app, encoding multi-discipline rules and officer permissions, and supporting 4,800 users with 14,000 authorization records.
  • Advised and supported the launch of multiple small businesses, including a regional market leader that expanded from one to two vehicles and reached profitability on an aggressive timeline.

Credentials and tools

MBA, PMP, IBM Gen AI Product Manager Specialization, and Harvard Extension coursework in C, Python, JavaScript, and React. I write user stories, design ERDs, run Agile cadences, and partner closely with engineering and compliance. My default mode is measurable outcomes, humane processes, and clear communication.

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