November 17, 2025
Article
Insurance: The Industry Where Most of Your Assumptions Are Wrong Think You Understand Insurance?
Insurance is one of the few industries in the world where even the smartest business people consistently learn that most of their assumptions are wrong. The insurance industry operates on principles that defy conventional business logic, from invisible products to distribution controlled by aggregators, success measured by loss ratios rather than revenue growth, and insurance technology that can accelerate churn if implemented incorrectly.
Success in this sector requires navigating capital requirements, insurance compliance frameworks, and core systems running on mainframes older than the internet. There are industries that look inefficient from the outside—ripe for disruption, bloated with legacy systems, seemingly allergic to innovation. Then there's insurance: an industry so counterintuitive that even the most brilliant, well-funded founders routinely walk in with confidence and walk out humbled.
It's one of the few sectors where intelligence and ambition alone aren't enough. Even founders with billion-dollar track records learn—painfully—that almost every assumption they brought from "normal" business doesn't apply to insurtech insights and operations. Let's explore why this is the case—and what it teaches us about other industries that only look simple from the outside
The Product Is Invisible Until Something Bad Happens
In most businesses, your product delights people when things go right. With insurance, your product only truly matters when things go wrong. You spend years building, marketing, and servicing something that your customer hopes they will never use. There's no daily engagement, no immediate gratification, no unboxing moment.
Most customers only think about their insurer twice a year—when they pay their premium and when they file a claim, and the latter is almost always under stress or frustration. This creates a paradox for insurance & technology providers: you're selling peace of mind, not a tangible experience.
That means your marketing isn't about features—it's about trust. And trust is a brutal currency to earn, especially in a category where every competitor makes the same promise and every bad claim story goes viral. For insurtech news startups used to rapid iteration and feedback loops, this lack of visibility is disorienting. You can't A/B test your way to trust, and by the time you learn whether your risk models actually work, you're already writing checks for losses.
Distribution Is Owned by Aggregators, Not Brand Love
In most consumer markets, building a beloved brand can win you distribution. In insurance, distribution owns you—especially for Brokers & MGAs. Aggregators, brokers, and comparison sites dominate the customer journey. When people search for "cheap car insurance," they don't start by Googling a brand—they click on an aggregator that presents dozens of indistinguishable offers sorted by price.
Your painstakingly crafted brand identity, customer experience, and clever slogan vanish behind a wall of price filters and cookie-cutter policy summaries. That's why many early insurtech insights startups underestimated the power of the middleman. They assumed they could build a direct-to-consumer brand and win with better UX or lower prices, but the reality is that acquisition costs are crushing.
The customer's loyalty lies with whoever saves them $50 on renewal—not with you. This is why so many "digital disruptors" end up becoming another broker, because that's where the distribution power—and the data—really lives.
Success Is About Loss Ratios, Not Revenue Growth
In most startups, growth is everything. You can burn cash to gain users because more customers means more data, more revenue, and eventually more profit. In insurance, that logic can kill you.
Every policy you sell is a liability, not an asset. The more you grow, the more risk management challenges you underwrite. If your loss ratios—the percentage of premiums paid out in claims—get even slightly out of balance, your entire business model collapses.
This is why insurance executives obsess over "underwriting discipline" and underwriting technology. It's not about growing fast—it's about growing safely. A company that grows too quickly without understanding its risk exposure is like a car accelerating downhill with no brakes.
Investors who come from tech often struggle with this mindset. They want hockey-stick growth, but insurance rewards patience, precision, and actuarial prudence through artificial intelligence underwriting and robust risk management systems.
Tech Alone Can Accelerate Churn or Risky Customers
At first glance, insurance technology seems like the perfect lever to modernize insurance operations. Automate the underwriting with artificial intelligence underwriting company solutions, digitize the claims with document workflow automation software, and personalize the premiums.
But the irony is that tech alone can make things worse. If you use algorithms to acquire customers faster, you might also attract the wrong ones—high-risk profiles that sophisticated insurers already learned to avoid. If you automate claims without careful fraud detection, you can end up with systemic losses at scale.
If you make switching providers frictionless through easy-to-use platforms, you reduce your ability to retain your best customers while subsidizing the riskiest ones. Tech amplifies whatever's already in the system—good or bad. And in a risk-based business, that amplification can destroy you before you even notice it happening.
The best AI insurance companies realized this the hard way. Technology isn't the disruption—it's the infrastructure. The real innovation is in how you manage risk through underwriting technology, structure capital, and build trust.
Capital + Compliance Drain You Before You Launch
Startups thrive on velocity: build fast, ship fast, learn fast. Insurance moves at the speed of regulation and insurance compliance. Before you can even sell your first policy, you need licenses, compliance officers, capital reserves, and actuarial validation. In some markets, you might need approval from multiple state or national regulators.
Each change to your pricing or product may trigger a new filing or audit, requiring comprehensive regulatory reporting and audit trail documentation. That means millions of dollars and months of legal work before you generate a cent of revenue.
This barrier isn't a bug—it's a feature. Insurance is deeply entwined with public policy and consumer protection through insurance compliance frameworks. The rules exist because when insurers fail, real people lose everything. But it's also why so many bright entrepreneurs give up before they even get to market. The cost of entry is measured not just in cash, but in stamina.
Core Systems Run on Mainframes Older Than the Internet
Many insurers still rely on systems written in COBOL and running on mainframes from the 1980s. That's not hyperbole—it's literally true. In fact, some core insurance databases are so old that only a handful of programmers in the world can still maintain them.
Modernizing these systems with cloud-native insurance technology isn't as simple as migrating to the cloud. Every policy, claim, and pricing model is entangled in decades of regulatory history and custom integrations. One wrong change can have downstream effects on insurance compliance, solvency reporting, or customer data.
That's why new insurtech news entrants often underestimate the complexity of legacy tech. It's not just outdated software—it's the institutional memory of how insurance actually works. To rebuild it with document management dms and modern insurance tool kits, you need to understand every legal, actuarial, and operational dependency that has accumulated over half a century.
The Lesson: Stop Trying to Disrupt It. Start Trying to Understand It.
The smartest insurance technology innovators aren't the ones shouting "we're going to disrupt this dinosaur". They're the ones quietly embedding themselves inside the system, learning its rules, and finding leverage points that others overlook through insurtech insights.
They partner instead of antagonize Brokers & MGAs. They respect the actuaries and compliance officers who keep the system stable through regulatory reporting and audit trail management. They build cloud-native insurance technology that complements, rather than replaces, the complex human judgment that risk management requires.
In short, they stop trying to make insurance normal. Because it isn't—and that's exactly why it's so important.
Other Industries That Humble Outsiders
Insurance isn't the only industry that punishes naive disruption. Here are a few others that look simple until you're inside them:
Healthcare: "Just fix healthcare" is the most dangerous sentence in Silicon Valley. The U.S. healthcare system is a maze of payers, providers, regulators, and incentives that often work against each other. Every startup learns the same lesson: the customer isn't who you think it is, the user doesn't control the payment, and the data you need is locked in a hundred incompatible systems requiring document management solutions. The best healthtech companies don't try to replace hospitals or insurers—they work within the system to make one process, one workflow, or one patient experience slightly better through easy-to-use technology.
Education: Everyone thinks education just needs better software and document workflow automation software. But education is cultural, political, and deeply human. Teachers, unions, parents, and students all have different goals. You can't "disrupt" learning outcomes with an app. Edtech startups that survive are the ones that support teachers with insurance tool kits and workflows, not replace them.
Real Estate: Real estate looks simple—buy, sell, rent, repeat. But behind every transaction lies an avalanche of regulation, local politics, zoning, financing, and emotional attachment requiring comprehensive document management in sap and document management on sharepoint systems. Platforms learned that housing isn't a marketplace problem—it's a human one. People don't buy houses the way they buy shoes.
Logistics and Supply Chain: Founders often assume logistics is just about optimization—make it faster, cheaper, more automated with efficiency-focused tools. Then they discover the brutal reality of unions, fuel costs, customs, weather, and global dependencies. Moving physical goods reliably is an art form that blends technology, relationships, and resilience.
Agriculture: From afar, agriculture looks ready for data-driven transformation. But inside, it's a dance between biology, weather, regulation, and culture. You can't A/B test a growing season or iterate faster than nature allows. Agtech founders learn that the farmers they want to "help" often know more about risk management than any spreadsheet ever will.
Final Thought
The dream of disruption is intoxicating. Every generation of entrepreneurs believes they can remake old industries with better insurance & technology and better intentions. And sometimes they do through cloud-native insurance technology and artificial intelligence underwriting platforms.
But the real lesson from insurance—and from all these "impossible" sectors—is humility. Before you can change a system, you have to understand why it exists. You have to appreciate the constraints that keep it stable through insurance compliance, the incentives that shape behavior, and the quiet wisdom built up over decades of trial, error, and regulation.
The best founders don't start with "How do we fix this?". They start with, "What do we not yet understand?". And in industries like insurance, that's the question that never stops humbling you.

