Investor Series Part 2: Insurance
- blairsheppard1
- Sep 22, 2025
- 2 min read
When Value Becomes Uninsurable: Why Reinvention in Financial Services Is Urgent
It’s worth asking: why is reinvention in financial services so critical right now?
Because if we’re slow to respond to the convergence of global threats—climate instability, technological disruption, demographic shifts, and a fracturing world—the loss in global value could be catastrophic. Not just in terms of assets and investments, but in the very money we save for rainy days. Entire portfolios—physical and digital—could be virtually erased.
That may sound alarmist. It did to me, until I had a call with the research team of one of the world’s largest reinsurance companies.
Reinsurers are the insurers of insurance companies—the final backstop against major losses. Their job is to understand risk better than anyone else on the planet. Their research teams are composed of brilliant minds who study trends with precision and urgency. If anyone can quantify the future, it’s them.
We began with a focused discussion: the existential threats to the insurance industry itself. What happens to auto insurance when vehicles are autonomous and personal liability disappears? What happens to real estate insurance when coastal properties—some of the most valuable in the world—become uninsurable? What happens to life insurance when actuaries can no longer predict how long we’ll live? What happens to corporate insurance when companies that fail to reinvent simply cease to exist? And what happens to health insurance when aging populations overwhelm systems that can’t adapt?
But it was only later, reflecting on the conversation, that I grasped the deeper implication.
If reinsurers—whose entire business is built on quantifying worst-case scenarios across every dimension of life, work, and community—are beginning to question their ability to measure risk, then something more profound is happening. The very notion of value is being destabilized. If risk becomes unquantifiable, then value itself becomes uncertain. And when the value of value is in question, the foundation of our financial systems begins to crack.
Yet amid this uncertainty, a new frontier is emerging. A multitude of alternative insurance models are gaining traction—especially those that focus on insuring the future of those who adapt first. These models reward resilience, innovation, and proactive transformation. They shift the paradigm from protecting against loss to enabling reinvention. In doing so, they offer a glimpse of what financial services could become: not just reactive, but regenerative.
This is why reinvention isn’t optional. It’s imperative. Not just for insurers, but for all of us who depend on the systems they underpin. The future of financial services—and the future of value itself—depends on our ability to adapt before the ground beneath us shifts too far.




Blair, your framing resonates deeply. When reinsurers start questioning measurability, they are indeed questioning value itself.
And industry observers are rightly pointing to four critical gaps:
Protection: too much risk still slips through the net.
Resilience: our systems can’t keep pace with cascading shocks.
Talent: the skills we have don’t match the complexity we face.
Funding: capital flows aren’t yet aligned with emerging risks.
When I look at this through the lens of what I call the Killer Waves, i.e. 🌍 the Sustainability Wave (ecological thresholds + societal demands) and 🤖 the Intelligence Wave (AI + synthetic cognition), I see an even bigger opportunity. These gaps aren’t just operational challenges; they are signals to redefine value itself on systemic terms.
If reinvention is anchored…