About Obie
Obie is a Financial Services company based in Chicago (United States) founded in 2014 by Ryan Letzeiser and Aaron Letzeiser, and was acquired by The Baldwin Group in January 2026. Insurance solutions are offered to landlords and real estate investors. It operates on a InsurTech and Direct-to-Consumer (D2C) model. Obie has raised $39.65 million across 6 funding rounds from investors including FundersClub, DivcoWest and The Baldwin Group. Its chief executive, as recorded, is Ryan Letzeiser. Its website obieinsurance.com draws about 77 thousand monthly visits. Obie offers products and services including Landlord Insurance and Embedded Insurance. Its focus areas include Insurance and Property Insurance. Its legal entity is Obie Insurance Group, LLC.
Company details
Insurance coverage is offered by Obie for landlords and real estate investors, focusing on property protection. Services are tailored for single-family and multifamily homeowners, as well as property managers. Solutions are designed to minimize risks and support portfolio growth in the real estate sector. Technology-driven platforms are utilized to deliver instant quotes and seamless integration for clients and partners.
- Headquarters Chicago, United States
- Founders Ryan Letzeiser, Aaron Letzeiser
- Stage Acquired
- SectorsFinancial Services
- Website category Finance · Insurance
- Email••••••••
- Phone•••• ••••
- Website obieinsurance.com
- Social LinkedIn X
- Acquired by The Baldwin Group (Jan 2026)
- Legal Name Obie Insurance Group, Llc
- Total Equity Funding$39.65M (USD)
in 6 rounds
- Latest Funding Round$26M (USD), Series B
Mar 2023
- InvestorsFundersClub
& 14 more
- Acquired byThe Baldwin Group
(Jan 2026)
Products & Services of Obie
Obie offers a comprehensive portfolio of products and services, including Landlord Insurance and Embedded Insurance.
Tailored coverage is provided for real estate investments.
Integrated insurance solutions are offered for seamless protection.
Funding Insights of Obie
Obie has successfully raised a total of $39.65M across 6 strategic funding rounds. The most recent funding activity was a Series B round of $26 million completed in March 2023. This substantial capital infusion reflects strong investor confidence in the company's business model, growth potential, and market opportunities. The funding enables strategic expansion, product development, market penetration, and operational scaling to drive long-term value creation and competitive advantage.
- Total Funding $39.65M
- Total Rounds 6
- Last Round Series B — $26M
- Investors Count 14
All 6 funding rounds of Obie with amounts and investors; the two latest post-money valuations are shown, the rest are part of the premium plan.
| Date | Amount | Transaction Name | Valuation | Lead Investors | Investors |
|---|---|---|---|---|---|
| Mar 2023 | $26M | Series B | – | Battery Ventures | |
| May 2021 | $10.7M | Series A | – | Battery Ventures | |
| Feb 2020 | $2.8M | Seed | – | MetaProp NYC, FundersClub | |
| Aug 2019 | $150,000 | Seed | – | Y Combinator | – |
| Jan 2019 | Seed | – | – | ||
| Sep 2017 | Seed | – | – | – |
15 investors in total: 12 institutional and 3 angel.
Investors in Obie
Obie has secured backing from 15 investors, including venture fund, institutional, and angel investors. Prominent investors backing the company include FundersClub, DivcoWest and The Baldwin Group.
| Investor | Description | Founded Year | Domain | Location |
|---|---|---|---|---|
Investments in technology companies are conducted globally by Battery Ventures. | battery.com | |||
VC firm investing in the US | brickmortar.vc | San Francisco, United States | ||
Investments are directed toward fintech, cybersecurity, and martech sectors. | thomvest.com | San Francisco, United States | ||
SaaS-based companies are invested in by Second Century Ventures. | scv.vc | Chicago, United States | ||
Early-stage startups are accelerated via funding and educational programs. | ycombinator.com | Mountain View, United States | ||
Venture capital fund focused on seed-stage investment in multiple sectors | liquid2.vc | San Francisco, United States | ||
Early-stage investments are provided by Soma Capital to startups. | somacap.com | San Francisco, United States | ||
| foundationcapital.com | ||||
Real estate debt fund focused on core and core-plus strategies | 1993 | divcowest.com | San Francisco, United States | |
Fundraising platform connects startups with investors for capital and support. | 2012 | fundersclub.com | San Francisco, United States |
Investor details for Obie
The complete investor list, round-by-round participation and investor portfolios require an active premium plan.
- Complete investor list
- Round participation
- Investor portfolios
- Co-investor network
Verified entity values are shown only after access is granted.
People of Obie
2 people are tracked at Obie (2 in leadership).
| Name | Role | Group |
|---|---|---|
Ryan Letzeiser | Co-Founder & CEO | Leadership |
Aaron Letzeiser | Co-Founder | Leadership |
Complete people profiles for Obie
Full employee and board profiles, team structure, tenure and professional contact details require an active premium plan.
- Full employee list
- Team structure
- Board tenure
- Professional contacts
Verified entity values are shown only after access is granted.
Timeline of Obie
4 dated milestones of Obie across 12 years, from founding to its latest funding, stage changes and deals.
- Founded Obie is founded.
- Funding First funding round.
- Funding Latest funding round, Series B, of $26.0M.
- Exit Acquired by The Baldwin Group.
Web traffic of Obie
The website of Obie (obieinsurance.com) receives about 77K visits a month and ranks #369,417 among all websites worldwide, #1,909 in Insurance.
- Monthly visits77K
▲ 26.9% vs previous month
- Unique visitors29.7K
per month
- Global rank#369,417
among all websites
- Category rank#1,909
Finance · Insurance
- Bounce rate38%
- Pages per visit6.4
- Average visit3 min 48 sec
- DevicesDesktop 66% · Mobile 34%
Websites whose visitors overlap most with Obie. Affinity shows how closely the audiences match.
| Website | Domain | Audience affinity | Monthly visits | Global rank | Profile |
|---|---|---|---|---|---|
mycoverageinfo.com | mycoverageinfo.com | 100% | #86,613 | – | |
| acentria.com | 97% | #3,644,088 | View details | ||
supercheapinsurance.com | supercheapinsurance.com | 97% | #636,929 | – | |
foragentsonly.com | foragentsonly.com | 96% | #18,718 | – | |
| thehortongroup.com | 96% | 10.4K | #2,840,662 | View details | |
| •••••••••• | ••••••.com | ••% | •.•M | #••••• | – |
| •••••••••• | ••••••.com | ••% | •.•M | #••••• | – |
| •••••••••• | ••••••.com | ••% | •.•M | #••••• | – |
All 37 similar websites and full traffic analytics for Obie
The complete similar-websites list, audience overlap and engagement analytics require an active premium plan.
- 37 similar websites
- Audience overlap
- Engagement analytics
- Traffic by brand
Verified entity values are shown only after access is granted.
Top companies in Insurance Providers
3 companies that operate in the same segment as Obie (Insurance Providers) in United States, ranked by their profile score on The Company Check.
| Company | Description | Founded | Location | Total funding | Revenue | Employees |
|---|---|---|---|---|---|---|
Provider of a cloud-based platform for life and P&C insurance | 2015 | New York, New York, United States | USD 644 M | USD 615.2 M | 1,471 | |
Online small business insurance policies are provided. | 2016 | Palo Alto, California, United States | USD 1.12 B | 549 | ||
App-based comparison platform for financial products | 2009 | San Francisco, California, United States | USD 123.3 M | USD 836.6 M | 650 |
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Related news about Obie
Complete news archive for Obie
Full article history, source details, and older brand coverage require an active premium plan.
- Full article archive
- Source and publication date
- Older coverage
- Brand-specific news history
Verified entity values are shown only after access is granted.
Frequently Asked Questions about Obie
Obie was founded in 2014 and raised its 1st funding round 3 years after it was founded.
Obie is headquartered in Chicago, United States. It is registered at Chicago, Illinois, United States.
Ryan Letzeiser is the CEO of Obie, as recorded in our data. They have also founded this company.
Obie is a funded company, having raised a total of $39.65M across 6 funding rounds to date.
Insurance coverage is offered by Obie for landlords and real estate investors, focusing on property protection. Services are tailored for single-family and multifamily homeowners, as well as property managers. Solutions are designed to minimize risks and support portfolio growth in the real estate sector. Technology-driven platforms are utilized to deliver instant quotes and seamless integration for clients and partners.
Obie offers Landlord Insurance and Embedded Insurance.
Obie has 15 investors. Key investors include FundersClub, DivcoWest, The Baldwin Group, Battery Ventures, and Brick & Mortar Ventures.
Obie operates through Obie Insurance Group, Llc.
Yes. Obie was acquired by The Baldwin Group in January 2026.