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Obie, an insurtech platform for landlords, raises $10.7M


Fulton East, an office building at 215 N. Peoria St.
Fulton East, an office building at 215 N. Peoria St.
Parkside Realty

A Chicago startup building real estate insurance for landlords just raised a new round of funding to help it build out its platform.

Obie, founded in 2017, announced Wednesday that it raised $10.7 million in a Series A round led by Michael Brown and Battery Ventures. Other investors Thomvest Ventures, Funders Club and Metaprop also participated.

To date, Obie has raised more than $13 million. It raised a $2.8 million seed round last year from investors like Y Combinator, a prestigious Silicon Valley startup accelerator that Obie participated in shortly after launching.

Obie has built a cloud-based insurance and portfolio management platform for small- and medium-size apartment landlords. Within the last two years, Obie says it provided insurance to cover over $3.5 billion in rental property and is available in all 50 states.

Obie says it offers cheaper insurance options than competitors, and on average, saves its clients 25% on insurance costs.

To continue expanding its footprint, Obie also acquired competitor Skylight Insurance last year.

Obie is led by CEO Ryan Letzeiser, who founded the company with his brother, Aaron Letzeiser, after nearly a decade working in real estate private equity. 

“We saw chronic problems throughout the real estate insurance market so we’re reinventing the process from the bottom up,” Ryan Letzeiser wrote in a blog post announcing the funding. “We are starting at the intersection of insurance and technology which allows us to address the insurance needs of independent investors and landlords that have largely been ignored by insurance carriers.”


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