For New Disruptors

Disruption Now® exists to make emerging technology more human, accessible, and actionable. This week, I’ve been reflecting on how easily institutions hide behind complexity. Hospitals, banks, school systems, and even local governments depend on paperwork and processes to stay unchallenged. For generations, they’ve controlled information. Now, ordinary people are learning to fight back, with precision, not rage. Artificial intelligence is giving citizens a way to investigate power itself.

The Family Who Faced a $195K Bill

The scene could happen anywhere. A family sits around a kitchen table, the hum of the refrigerator filling the silence. A hospital envelope lies open between them. Inside: a $195,000 bill. The charge? Four hours in an emergency room after a fatal heart attack.

The widow can’t process the number. Her brother-in-law, a quiet, analytical type, takes the papers home that night. He’s not an expert in healthcare billing. He’s an ordinary citizen with an ordinary laptop. But he decides to try something new.

He uploads the itemized bill to Claude. Within minutes, Claude starts decoding the impossible language of medical bureaucracy, line by line, code by code. It identifies $162,000 in likely Medicare violations and duplicate charges.

The brother-in-law prints the AI’s analysis and submits a written challenge. Two weeks later, the hospital revises the total. The $195,000 bill drops to about $33,000. Still painful, but survivable.

He didn’t threaten, beg, or hire a lawyer. He investigated. And what he uncovered was not just one hospital’s mistake. It was a pattern, a glimpse of how complexity shields institutions from accountability.

The Hidden Strategy of Complexity

Across nearly every system, complexity isn’t an accident. It’s a defense.

Hospitals bury patients under CPT codes and Medicare modifiers. Banks hide fees behind shifting disclosures. School districts cite regulations that parents rarely read. Tax assessors rely on formulas that no homeowner can verify without an accountant.

This asymmetry of information creates a quiet imbalance of power. Institutions don’t need to deceive you directly; they only need to make the truth too expensive or time-consuming to uncover. They rely on exhaustion more than force.

AI changes that equation. For the first time, anyone can read what once required a specialist. A parent can review an Individualized Education Program (IEP) and identify compliance failures in the law that guarantee their child’s learning support. A homeowner can compare their property tax assessment to official valuation formulas. A student can check whether their loan servicer’s fees violate federal disclosure requirements.

When knowledge becomes accessible, silence becomes a choice.

AI as an Investigative Ally

AI is not replacing lawyers, advocates, or journalists. It’s replacing helplessness.

Used responsibly, it turns overwhelming systems into transparent ones. It can analyze bills, contracts, or policies and explain them in plain English. The key is to use it as an investigative ally, not a replacement for human judgment.

The brother-in-law who challenged the $195K bill didn’t ask, “What should I do?” He asked, “What rules govern this?” That single question changed everything. He shifted the frame from emotion to evidence. From begging for mercy to demanding compliance.

AI doesn’t give you the correct answer; it gives you a map. It shows how the system is designed, where it breaks its own rules, and how to use its standards to hold it accountable.

The same technique works far beyond healthcare. AI can flag inconsistencies in student loan disclosures, detect illegal late fees, or identify when a local government fails to follow its own zoning procedures. It’s not magic. It’s literacy—digital, legal, and civic.

The Investigator’s Mindset

To wield AI effectively, you need the mindset of an investigator, not a petitioner. Three strategies form the foundation of that mindset.

1. Investigate before you negotiate. Emotional appeals are easy to dismiss. Documentation is not. Build your case first, then engage.

2. Control the frame. Institutions prefer to define the issue on their terms. “We’ll see if you qualify for charity care” reframes a compliance issue as a favor. Don’t accept that frame. Keep the focus on documented errors.

3. Treat every response as data. When a company or agency replies, that’s not the end—it’s intelligence. Their tone, timing, and language tell you how confident they are. AI can help analyze these responses, spotting patterns in language that reveal pressure points.

Once you internalize this mindset, you stop reacting and start diagnosing.

The Eight Principles of Institutional Self-Defense

1. Make the AI Read the Fine Print

The first step is often the hardest for humans: reading the rules. Upload the billing statement, insurance policy, or statute into your AI tool and ask for a breakdown of what each section means. AI can summarize, translate jargon, and highlight sections that seem inconsistent.

2. Cross-Reference Multiple Sources to Find Gaps

Violations often hide in the gray space between systems. Ask AI to compare your bill to official government guidelines, or your school’s policy to federal education mandates. These cross-references are where many errors live.

3. Adopt the Institutional Register

AI can help you write like a professional. Instead of “This seems unfair,” your letter can read, “This billing structure appears inconsistent with CMS bundling regulations.” Language signals competence. Institutions respond accordingly.

4. Find the Official Rulebook

Ask your AI which laws or regulations govern your issue. Nearly every system has a rulebook: the Fair Credit Reporting Act, the IDEA, Medicare’s fee schedule, and the Fair Debt Collection Practices Act. Knowing which one applies turns a complaint into a compliance audit.

5. Identify Clear, Categorical Violations

Focus on facts, not feelings. Instead of “You overcharged me,” point to the exact code or standard that was breached. An institution can debate opinions, but not documented contradictions.

6. Establish Objective Anchors

Build your argument on verifiable data. For medical bills, this could mean Medicare’s official rate for a procedure. For property taxes, use the assessor’s published valuation formula. For loans, cite the APR disclosure rules. Facts are the anchor that keeps your argument from drifting.

7. Let AI Collapse Investigation Costs, But You Stay in Control

AI can do most of the heavy lifting—researching laws, identifying inconsistencies, and drafting letters. But before sending anything, verify citations manually. A single false claim can weaken an otherwise airtight case.

8. Use AI to Fact-Check Itself

Ask the model to critique its own work. Prompts like “Review this draft for incorrect citations or logic gaps” often catch subtle issues. The best investigators double-check the machine’s findings with the machine itself.

My Disruptive Take

For centuries, institutions have maintained power by controlling access to information. They created the maze, then sold the map. That monopoly is ending.

AI is a literacy amplifier. It allows ordinary people to see behind the curtain, to understand the systems that shape their daily lives. When used with care and discipline, it restores balance between citizens and institutions.

This isn’t about rebellion. It’s about accountability. It’s about turning AI into a civic skill as ordinary as reading or writing.

For the first time, every citizen can read the fine print. And once you can read the fine print, you can rewrite the story.

Disruption Now® Podcast

This Week LATEST EPISODE Upgrading Government Tech: Startup Thinking for Public Service, we’re joined by Pavan Parikh, Hamilton County Clerk of Courts, who’s bringing a fresh, startup-minded approach to modernizing government. Pavan breaks down how agility, innovation, and data-driven thinking can transform public service from the inside out.

Keep Disrupting, My Friends.

Rob Richardson – Founder, Disruption Now® & Chief Curator of MidwestCon