Obie
AcquiredYC S19Chicago, US · Founded 2018 · 120 employees · 7 known investors
Find your way into Obie
10 people in our graph share verified history with the Obie team — schools, employers, funds. One of them is your warm intro.
Zach Nooraniunlockedknows Ryan Letzeiser · together at Obie (overlapped)
×9knows the team · via Clemson University
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.
Founders & leadership· Y Combinator alumni (S19)
Obie was founded in 2018 by Aaron Letzeiser and Ryan Letzeiser.
RL
Ryan LetzeiserinFounderRyan 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 · 7
Funding
SEC filings, press & company announcements$50M disclosed across 2 of 3 rounds · 2023
- Undisclosed amountfunding roundMay 2023
Battery Ventures (lead)
Source ↗ - $25MSeries B Funding RoundMay 2023 · 4 sources
Battery Ventures (lead)
Source ↗ - $25MraisedMay 2023 · 2 sourcesSource ↗
Source: company announcements and press reports — follow each round's link for the claim.
Competitors · 10
by search overlap
Steadily1492 shared keywordsSteadily provides landlord insurance policies that protect rental property owners against property damage, liability claims, and lost rental income. It covers various property types including short-term rentals such as Airbnb and VRBO listings, serving residential landlords in the United States.
Avail1343 shared keywordsA messaging platform feature for property managers and rental companies that links conversations to tenant lifecycle stages and provides filtering and alert capabilities.
Azibo1325 shared keywordsAzibo is a property management platform that enables landlords to collect rent, screen tenants, manage leases, track maintenance, and handle accounting and tax preparation. The platform serves residential and commercial property owners of all portfolio sizes.
Landlordstudio1307 shared keywordsLandlord Studio is a cloud-based accounting and property management platform designed for rental property owners to track income and expenses, generate tax reports including Schedule E filings, and manage tenant communications. The software serves individual landlords and property managers who need to organize their rental portfolios and simplify tax compliance with IRS-aligned financial reporting.
Zillow1287 shared keywordsZillow operates an online real estate marketplace where consumers can search homes for sale and rentals across US and Canadian cities, view mortgage rate information, and access home financing through Zillow Home Loans. It covers residential property listings, apartments and houses for rent, and mortgage services nationwide.
Turbo Tenant1279 shared keywordsTurboTenant provides tenant screening reports and rental application services for independent landlords managing rental property investments. The platform uses identity verification and background checks to help landlords evaluate prospective tenants.
Biggerpockets1214 shared keywordsBiggerPockets provides real estate investing tools, including property analysis calculators and property management software, along with a network of investor-friendly agents and vetted service professionals. It also offers educational content through articles, podcasts, videos, and guides, plus a community forum and tiered membership plans for real estate investors.
Baselane1200 shared keywordsBaselane provides accounting and financial management software for real estate investors and landlords, helping them track cash flow, manage property finances, and optimize tax deductions.
SmartAsset1183 shared keywordsFisher Investments is a global money management and financial advisory firm that provides portfolio management, financial planning, and retirement planning services primarily to high-net-worth individuals and institutional clients. The firm manages investments across equities, fixed income, and blended accounts using an active, forward-looking investment approach.
Doorloop1156 shared keywordsDoorLoop is a cloud-based property management platform that combines rent collection, tenant screening, e-leases, maintenance, and accounting in one system, with AI automation across leasing, maintenance, and communications. It serves landlords, property managers, and real estate investors managing portfolios of any size.
Companies competing with Obie for the same Google search keywords, organic and paid, via search-intersection analysis.
In the news
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, FundersClub, Harmony Partners, MetaProp, MetaProp Ventures, Y Combinator.
- 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.