About Decision Files
Decision Files is about how people think about decisions — how they frame them, how they approach them, alone or in a room full of stakeholders, and how they come to a conclusion. We’re leveling up how decisions get understood, starting with business decisions: technical, financial, operational, human. Fundamentally, we’re telling human stories.
“Technology should work in service of human cognition. The interface between people and machines should tilt toward the human.”
The pattern behind Decision Files goes back to NSS Labs: smart people making million-dollar decisions with zero empirical data. That gap — between the weight of a decision and the evidence available for it — never went away. It just moved to new markets. Decision Files closes it, one documented decision at a time.
An analyst interviews the person who made the call, and keeps the doubt in — the weak evidence, the disagreement, the option nearly taken. That’s what makes a file useful before your decision, not after it.
Each decision is mapped to the visual framework that names its pattern — one hand-drawn diagram that makes the shape of the decision legible at a glance. Underneath sits the same structured anatomy every time: question, stakes, signals for and against, missing evidence, alternatives, outcome, counterpoint. The analysis runs on UpSight, with every claim traced to what was actually said — and how we stay independent is on the independence page.
Rick is a multi-exit founder, CEO, CPO, and CMO with over two decades building and scaling B2B SaaS companies in cybersecurity, AI, and cloud networking — a career spent creating clarity and value for decision makers, and exits for investors.
As co-founder and CEO of NSS Labs, Rick created a new market category called “Real-world Testing” — testing cybersecurity products the way attackers would actually try to evade them. It was hugely controversial at the time; eventually it became the standard, adopted industry-wide.
He has held executive roles at ESET, AccuKnox, Acalvio, Tempered Networks, and Websense, and today builds UpSight, the AI-powered customer intelligence platform behind these files. An active startup advisor, investor, and Techstars mentor in the San Diego ecosystem, Rick continues to help organizations find clarity and make better business and technology decisions — through research, analysis, and the application of appropriate AI technologies.