Health insurance has become one of the most distrusted corners of the American economy, and for good reason. Books like Elisabeth Rosenthal's An American Sickness document how insurers, drug manufacturers, and hospitals each drive up costs, and multiple news outlets constantly report on denials, surprise bills, or premiums climbing faster than wages. In almost every other category, smarter consumers force companies to compete on experience. Health insurance is the exception: most Americans are locked into whatever their employer chooses, and the self-employed or contractors are left with a thin menu on the ACA marketplace. With no real choice, there is no real incentive to improve. It shows up in the numbers, where the average insurance NPS sits around 35 and health insurers routinely score below their peers. Molli Health caught our attention because it is rebuilding health insurance from the ground up, and layering on an AI-powered member experience built specifically for the people the system forgot: the 1099 workforce. We are investing because we believe Molli Health can transform how health insurance should operate, with the end customer in mind.
More than 70 million Americans now work independently, a number projected to approach 86 million by 2027, which would be roughly half the U.S. workforce. Yet the health insurance system was never designed for them. When you leave a W-2 job, you lose your coverage, and the individual market that is supposed to catch you is shrinking and unstable, with subsidies expiring and major carriers exiting the individual market entirely. The fastest-growing segment of the American economy is being asked to navigate its highest-stakes purchase alone, with worse options and less help than a salaried employee at a large company. Molli Health is building to solve this gap. Beyond the 1099 workforce, Molli Health is aiming to reshape the health insurance experience from the ground up, with a member-aligned experience that truly prioritizes overall health to lower costs.
Molli's approach is to unbundle the insurance supply chain and rebundle it with best-in-class partners, then pass the savings back to members. The result is better coverage for less than comparable ACA plans, a stronger network, lower deductibles, and smarter plan designs, all at a lower monthly cost. However, beyond cost savings is the member experience and the focus on the member as a customer rather than taking them for granted as being locked in. Rather than leaving people to decode their own benefits and search through hundreds of dense, hard to understand plan documents, Molli's AI navigation answers real questions about coverage, networks, and drug pricing, and can steer members to low cost high quality options: when a member needs a procedure, the app surfaces tiered cost options in real time, so a $2,500 MRI can become a $400 one. Molli also has a bigger goal, as over time they want to use wearable and longitudinal health data to shift the relationship from reactive claims processing to proactive, preventive care. This is the kind of long-term, member-aligned model the incumbents have no incentive to build.
Our conviction in founder and CEO Wyatt Stokesberry grew with every conversation. We were introduced to Wyatt and the Molli Health founding team from one of our top Fund I healthcare founders. What stood out from the beginning was Wyatt’s First Builder experience, being in the employer based healthcare market and deep understanding of the misaligned incentives between health insurance and their members. As we got to know him and the team, we saw their execution in action, iterating in a way that only a First Builder with a clear understanding of the problem can. Deciding to re-build health insurance from scratch is no easy task, and seeing the team do just that with the end member experience in mind has been inspiring. We are honored to partner with Wyatt and the Molli team from Fund II.
At The Council, we believe healthcare is an essential industry sitting squarely within Software's Third Act, with enormous room to build. It is also nuanced, regulated, and genuinely hard, which is precisely why progress here is so durable when it comes. Health insurance touches nearly every American, and rebuilding it around the member rather than the system is the kind of change that compounds for decades. We are excited to back First Builder founders like Wyatt and companies like Molli Health that are taking it on.
Molli Health is live now and enrolling for July 1, 2026. Learn more about the plan options and enroll here: https://www.mollihealth.com/
