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Obie

AcquiredYC S19

Chicago, US · Founded 2018 · 120 employees · 19 known investors

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Obie provides landlord and investment property insurance for real estate investors and professionals. The platform streamlines quote comparison, binding, and policy management for residential and commercial investment properties.

InsurTechPropTechReal EstateInsuranceUnited States of AmericaAmerica / CanadaPartly Remote

Founders & leadership· Y Combinator alumni (S19)

Obie was founded in 2018 by Aaron Letzeiser and Ryan Letzeiser.

ALAaron Letzeiser
Aaron LetzeiserFounder
RLRyan Letzeiser
Ryan LetzeiserFounderRyan Letzeiser is Co-Founder and CEO of Obie, an insurance distribution platform acquired by the Baldwin Group in January 2026. He has over 15 years of experience in technology, insurance, and real estate, including prior roles at Hudson Capital Investments and Ram Real Estate, and holds a Master's degree in Architecture from Clemson University and a Bachelor's degree in Science from Michigan State University.

Investors · 19

Brick Mortar Ventureslisted by Brick Mortar VenturesSan Francisco

How we know: Brick Mortar Ventures's portfolio page · the VCSheet dataset · Not right? Tell us

Foundation Capitallisted by Foundation CapitalPalo Alto · $250K – $15M

How we know: Y Combinator's founder network · foundationcapital.com · Not right? Tell us

FundersClublisted by FundersClubSan Francisco · $290K

How we know: FundersClub's portfolio page · Not right? Tell us

Harmony Partnerslisted by Harmony PartnersNew York

How we know: the VCSheet dataset · Not right? Tell us

MetaProplisted by MetaPropNew York · $100K – $1M

How we know: the VCSheet dataset · Not right? Tell us

MetaProp Ventureslisted by MetaProp VenturesNew York
Soma Capitallisted by Soma CapitalSacramento · $100K – $300K

How we know: Y Combinator's founder network · somacap.com · open dataset · 5k.vc investor directory · Not right? Tell us

Y Combinatorlisted by Y CombinatorSan Francisco · $500K

How we know: the Y Combinator directory · open dataset · 5k.vc investor directory · Not right? Tell us

Amplify PartnersreportedMenlo Park · $500K – $5M

How we know: Y Combinator's founder network · Not right? Tell us

FrialereportedNashville · $100K – $600K

How we know: Y Combinator's founder network · Not right? Tell us

James Beshara FundreportedVenice

How we know: Y Combinator's founder network · Not right? Tell us

Kleiner PerkinsreportedMenlo Park · $500K – $15M

How we know: Y Combinator's founder network · Not right? Tell us

Liquid VenturesreportedSan Francisco · $250K – $5M

How we know: Y Combinator's founder network · Not right? Tell us

Pearson VenturesreportedLondon

How we know: Y Combinator's founder network · Not right? Tell us

PioneerreportedToronto, Ontario

How we know: Y Combinator's founder network · Not right? Tell us

Sequoia CapitalreportedMenlo Park · $100K – $50M

How we know: Y Combinator's founder network · Not right? Tell us

Thomvest VenturesreportedSan Francisco · $2M – $5M

How we know: Y Combinator's founder network · Not right? Tell us

Valley Oak Investmentsreported

How we know: Y Combinator's founder network · Not right? Tell us

Funding

SEC filings, press & company announcements

$50M disclosed across 2 of 3 rounds · 2023

Source: company announcements and press reports — follow each round's link for the claim.

Related companies · 10

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Companies working in the same space as Obie.

In the news

Obie Raises $25M in Series B Fundingfinsmes.com · May 2023

Frequently asked questions

What does Obie do?
Obie provides landlord and investment property insurance for real estate investors and professionals. The platform streamlines quote comparison, binding, and policy management for residential and commercial investment properties.
Who founded Obie?
Obie was founded by Aaron Letzeiser, Ryan Letzeiser in 2018.
Who are Obie's investors?
Obie's investors include Battery Ventures, Brick Mortar Ventures, Foundation Capital, FundersClub, Harmony Partners, MetaProp, MetaProp Ventures, Soma Capital and 11 more.
How much funding has Obie raised?
Obie has disclosed $50M raised across 2 of its 3 known rounds.
Where is Obie headquartered?
Obie is headquartered in Chicago, US.