Obie (YC S19) — Moving investment property insurance forward
Since 2017, Obie has simplified real estate investment insurance for landlords, property managers, agents, and investors across the U.S. With expert-backed coverage, intuitive tools, and embedded technology, Obie delivers fast, reliable insurance solutions designed to fit how real estate professionals work today.
Obie is a Y Combinator company in the Summer 2019 batch. Its directory entry describes it as: Moving Investment Property Insurance Forward. The founders listed are Aaron Letzeiser (Founder), Ryan Letzeiser (Founder) (Y Combinator directory entry, April 25, 2019).
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Since 2017, Obie has simplified real estate investment insurance for landlords, property managers, agents, and investors across the U.S. With expert-backed coverage, intuitive tools, and embedded technology, Obie delivers fast, reliable insurance solutions designed to fit how real estate professionals work today. With $60 billion in coverage secured and $39 million in funding, Obie is redefining what insurance can do—for the people building the future of real estate
Aaron Letzeiser
Founder
Ryan Letzeiser
Founder
Founders, titles and bios as the company published them. Photographs are our own copies of the ones on that record, so they do not break when the original link expires.
One of 86 companies held here in Real Estate and Construction › Housing and Real Estate.
No investor is drawn from a Form D — the form states how many invested and never who. The one investor on this graph is named because a batch has exactly one.
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Example from a real report (our sample on Target): “In March 2026, Target announced a planned incremental $1 billion operating investment” Source: Target Corporation (press release)
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What the Full Report on Obie covers
The Short Answer
Which Company This Is
What They Do, And How The Money Works
Who Runs It, And How To Reach Them
The Money: Funding, Valuation, Runway
Who Pays Them, And Who They Are Up Against
Warning Bells
Sources
1 cited source found
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