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Obie

“Can a vertical insurtech own investment-property insurance by embedding at the point of loan closing?”

Founded2017
HQChicago, Illinois, United States
FoundersAaron Letzeiser, Ryan Letzeiser
Total raised$39M+
Latest roundSeries B, 2023
IndustryFintech / Insurtech

The story

Obie is an insurtech focused exclusively on investment-property insurance for landlords and real estate investors — single-family rentals through larger apartment buildings. Founded 2017 and incubated at Y Combinator, the company evolved from a direct-to-landlord quote tool into an embedded insurance platform distributed through real estate platforms, lenders, and technology partners via APIs that return bindable quotes at the point of loan origination.

Last 12 months

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Product timeline

2017

Founded in Chicago by brothers Aaron and Ryan Letzeiser to serve small-to-medium landlords with insurance· pivot

2021

Raised $10.7M Series A led by Battery Ventures after going through Y Combinator· banking

2023

Raised $25.5M Series B; grew from $3B to $20B of property insured· banking

The stack

1 layer disclosed in Obie’s embedded-finance stack

Insurance

Obie Insurance (self-operated)

Accounting gap: none

Obie — frequently asked

Which insurance provider does Obie partner with?

Obie's embedded insurance is provided by Obie Insurance (self-operated).

Who founded Obie?

Obie was founded by Aaron Letzeiser and Ryan Letzeiser and is founded in 2017, headquartered in Chicago, Illinois, United States.

How much funding has Obie raised?

Obie has raised $39M+ in total (latest round: Series B, 2023).

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