At a glance
- Organization
- Obie
- Type
- Insurtech / digital insurance platform
- Founded
- 2017
- Base / focus
- Chicago, Illinois
- Specialty
- Landlord and real estate investor insurance (digital distribution)
- Official site
- Visit Obie
Who is Obie?
Obie is an insurance technology and distribution company founded in 2017 that specializes in landlord and real estate investor insurance. It is not a traditional underwriting carrier; it places landlord, short-term rental, vacant/renovation, and portfolio coverage through partner carriers and digital platforms for property investors nationwide.
Obie was built for landlords and real estate investors who need coverage designed around rental income, tenant occupancy, and investment strategies — not a standard owner-occupied homeowners form. The platform emphasizes fast quoting and embedded insurance workflows for investors, lenders, and partner platforms.
Important distinction: Obie markets itself as an insurance technology / distribution business. Policies are placed with partner carriers rather than issued as “Obie Insurance Company” paper in the traditional carrier sense.
Key facts
- Founded in 2017 by brothers Ryan and Aaron Letzeiser
- Headquartered in Chicago, Illinois
- Focuses on landlord and real estate investor insurance — not owner-occupied homeowners
- Operates as a digital distribution / insurtech platform that places coverage with partner carriers
- Products commonly include landlord (DP-3), short-term rental, master/portfolio policies, and vacant/renovation coverage
- Acquired by The Baldwin Group (completed January 2026 per Obie’s announcement)
History
Obie was founded in 2017 by Ryan and Aaron Letzeiser after their own experience as real estate investors highlighted how slow and rigid traditional landlord insurance processes could be for strategies like flipping or BRRRR.
The company raised venture funding (including a Series B that brought total equity raised to roughly $39M per Obie’s announcement) to expand embedded insurance technology for the investor ecosystem.
In January 2026, The Baldwin Group announced it completed the acquisition of Creisoft, Inc. and its subsidiaries (collectively Obie), positioning Obie within a larger brokerage and MGA distribution platform while keeping its landlord-investor focus.
Products Obie offers
Obie’s public marketing focuses on investment-property insurance categories. Exact forms and partner carriers vary by property and state.
- Landlord insurance (often DP-3 style dwelling coverage for long-term rentals)
- Short-term rental insurance (Airbnb / Vrbo-style occupancy)
- Master / portfolio policies for multi-property investors
- Vacant and renovation / fix-and-flip coverage
- Related landlord liability and loss-of-rent features as offered on specific programs
Who Obie serves
Obie serves landlords, real estate investors, and partners such as lenders, agents, and property platforms that need investor-oriented insurance workflows.
Owner-occupants shopping a primary residence typically need a different product. Investors with 1–8 unit residential properties are the core audience described in Obie’s materials.
Coverage focus with Epic and Easy
Obie is commonly considered for:
- Landlord / rental dwelling insurance
- Investment and vacant-to-rental transitions when eligible
- Property portfolios that need landlord-focused underwriting
- Related property risks Obie offers through appointed agencies
Who it’s for in Virginia
Obie is aimed at landlords and investors in markets like Roanoke who need coverage designed for tenant-occupied or investment properties — not a standard owner-occupied HO-3 assumption.
If you mix personal homeowners and rentals, we help separate which market and form fits each address.
How Epic and Easy helps
We review occupancy, renovations, tenant status, and desired limits, then check Obie and other property markets we represent.
You get a clear recommendation on structure — and we explain exclusions that matter for landlords, such as vacancy conditions or liability expectations.
Obie FAQs
Is Obie an insurance company?
Obie is best described as an insurtech and insurance distribution platform for landlords and investors. It places policies with partner carriers rather than operating solely as a traditional underwriting carrier brand.
Is Obie the same as homeowners insurance?
No. Obie is oriented toward landlord and investment property needs. Owner-occupied homes usually need a different product. We’ll point you to the right form for each property.
When was Obie founded?
Obie was founded in 2017 by Ryan and Aaron Letzeiser and is based in Chicago.
Can I insure a Roanoke rental with Obie through Epic and Easy?
We can check Obie when we are appointed and the property qualifies. Availability depends on ZIP, occupancy, and underwriting.
What details do you need for a landlord quote?
Property address, occupancy status, reconstruction or dwelling limit goals, liability preferences, and any renovation or vacancy notes help us quote accurately.
Who acquired Obie?
According to Obie’s January 2026 announcement, The Baldwin Group completed the acquisition of Obie (Creisoft, Inc. and subsidiaries).
Sources & methodology
This profile summarizes publicly available information from the organization’s official website and related authoritative pages. Product lists describe what the organization markets broadly and do not guarantee availability through Epic and Easy in every ZIP or risk class.
Coverage, eligibility, pricing, and underwriting rules vary by state, product, and applicant. We do not invent AM Best scores, claim counts, or proprietary premiums on this page.
Advertiser Disclosure: Epic and Easy may be compensated when you request a quote or purchase coverage through our agency relationships. Compensation may influence which products we can offer. Carrier availability varies by product, ZIP, and underwriting. Product lists on this page describe what Obie markets broadly and do not guarantee that every product is available through Epic and Easy in every location. This page does not invent ratings, claim counts, or proprietary premiums.