Over 100 Years of Insurance Experience

I started my career as a corporate lawyer at a large international law firm in London. I was not a good fit for being a small cog in a big machine.

So I left, moved to the US, and co-founded Tough Mudder. We scaled that business from zero to $100 million in revenue in four years. It taught me what I wanted to do with my career: build things from scratch, move fast, and solve problems that established systems were not designed to solve.

I moved back to Europe to start a family and did an Executive MBA. When I returned to the US during Covid, I took a consulting engagement with a P&C insurance wholesaler, building a general liability program. That project pulled me across the entire insurance value chain: retail brokers, wholesale brokers, actuaries, reinsurance brokers, reinsurers, fronting companies, technology vendors. It was an education in how insurance actually gets distributed, and where the system breaks down.

I left because I wanted to be a founder again. This time in insurance.

I first saw the opportunity in PE-backed physician groups where some doctors were working as independent contractors and no longer had access to the employer-sponsored benefits they had relied on. The products existed. The infrastructure to enroll, collect payments from, and administer benefits for a distributed 1099 population did not.

So we built it.

Once the enrollment and administration platform worked for distributed 1099 populations, we started to see that the same distribution model could apply to voluntary long-term care insurance, and that market was far bigger. LTC was not limited to one industry. Very few people had coverage relative to the scale of the risk. And the existing distribution model was not built for it: voluntary benefits like LTC require education, individual decision-making, prolonged enrollment journeys, and payment infrastructure that traditional benefits administration was never designed to handle.

I did not come into insurance because of a lifelong calling. I saw a structural problem and a business opportunity. But the deeper I got into disability income protection and long-term care, the clearer it became that these products matter. DI protects a person's income. LTC protects a person's assets. Both can be critical parts of a financial plan, yet many working Americans lack adequate protection against either risk.

The products already existed. What was missing was infrastructure designed for how these populations actually enroll, pay, and stay covered. Hollowtree exists to build that infrastructure.