Obie – Transforming Investment Property Insurance Through Embedded Technology and Real Estate Expertise

The Big Picture

Some areas of real estate insurance have struggled to keep pace with evolving needs and expectations. Independent landlords and small-scale investors-those owning single-family or up-to-four-unit properties - often encounter lengthy, manual processes and fragmented experiences when securing coverage. This is especially frustrating given that insurance is a required component of every property deal, yet it can slow down transactions, create uncertainty, and increase the risk of lost revenue. Moreover, as real estate transactions increasingly move online, the gap between these investors' digital expectations and the insurance buying experience currently available to them continues to widen.

The Solution

Obie is bridging this gap by embedding landlord insurance directly into the platforms where real estate transactions occur. Obie's tech-first platform makes it possible to quote and bind policies in minutes through lenders, property managers, marketplaces, independent agents, or direct-to-consumer channels. By eliminating friction and paperwork, Obie empowers real estate investors to move faster, close deals confidently, and protect their assets with tailored coverage. Their unique approach is built on real estate expertise, insurance fluency, and modern APIs. It has changed the game for small independent landlords and real estate investors, turning insurance into a competitive advantage rather than an obstacle.

A Tech-Driven Origin Story

Obie was founded by brothers Ryan and Aaron Letzeiser, whose diverse backgrounds in real estate investing, tech entrepreneurship, and architecture fueled their mission to modernize property insurance. Obie began as an asset management platform for landlords, which evolved after the duo and their team identified a gap in the investment property insurance space. Obie joined Y Combinator's Summer 2019 cohort and has since raised over $40 million in funding. Today, Obie is active in 50 states and D.C. and is on track to write $150 million in premiums by the end of 2025.

From Momentum to New Milestones

With several successful years under its belt, Obie is looking to expand its footprint and diversify its offerings. New programs like PolicyProof, a platform for property managers with tools to simplify landlord insurance verification, ensures property owners' policy compliance and offers Master General Liability coverage. As Obie continues to scale, the focus on real estate expertise, insurance expertise, and modern technology remains foundational.

"We're building something big, but more importantly, something meaningful," said Laura Olson, Obie's Chief Insurance Officer. "And we know the real estate investment insurance market wants us to keep innovating, iterating, and growing together."