If you have ever tried to insure a rental property, you know the pain. You call a local broker, fill out a 10-page PDF, wait three days for them to "shop the market," and finally receive a quote that is 20% higher than you budgeted.
In an era where you can buy a house on your phone, why is it still stuck in 1990?
Enter Obie.
Obie has emerged as the dominant insurtech solution for real estate investors. By replacing manual underwriting with proprietary, user-friendly technology, they have cut the insurance process from weeks to minutes. But is faster actually better? And is it safe?
This full guide breaks down exactly what Obie is, how their technology works, and whether they are the right choice for your portfolio.
Company Overview: Who is Obie?
Founded in 2017 by brothers Ryan and Aaron Letzeiser, Obie was born out of personal frustration. As real estate investors themselves, the founders realized that the legacy insurance market didn't understand the speed required for modern strategies like BRRRR (Buy, Rehab, Rent, Refinance, Repeat) or fix-and-flipping, and was often too rigid for the everyday landlord.
- Headquarters: Chicago, IL.
- Backing: Obie is a venture-backed "unicorn in the making," having raised over $39 million in Series B funding led by Battery Ventures (investors in Coinbase and Wayfair) and Y Combinator.
- Mission: To remove friction from real estate transactions by embedding insurance directly into the closing process.
The Core Products: What Do They Actually Cover?
Obie is not a generic "home insurance" provider. They specialize strictly in commercial real estate risk.
1. Landlord Insurance (The DP-3 Standard)
This is Obie’s bread and butter. It covers the Dwelling (structure), Other Structures (fences/garages), and most importantly, Loss of Rent.
- Why it matters: If a fire forces your tenants out for 6 months, Obie pays you the rental income you would have received, ensuring you can still pay the mortgage.
2. Short-Term Rental (STR) Insurance
Standard homeowner policies specifically exclude "business activity." If an Airbnb guest slips in your shower, State Farm may deny the claim.
- Obie’s STR policy is built for high turnover. It includes commercial liability limits (often $1M+) and covers guest-specific risks, such as theft or amenity-related injuries.
The "Instant Quote" Technology: How It Works
Obie’s "secret sauce" is its data engine. When you type in an address, Obie doesn't just ask you questions; it instantly queries over 1,000 data points from public records, satellite imagery, and municipal permit databases.
- The Result: You don't need to know the exact year the roof was replaced or the square footage of the detached garage. Obie already knows.
- The Speed: This allows them to deliver a bindable quote in under 5 minutes.
Who Is Obie For? (And Who Is It NOT For?)
Obie is the perfect fit if:
- You are a BRRRR Investor: You need to switch quickly from a "Vacant/Renovation" policy to a "Landlord" policy the moment a tenant signs a lease. Obie handles this transition seamlessly.
- You are a Short-Term Rental (STR) Host: You need specialized coverage for high-turnover guests that traditional "long-term" policies often exclude. Obie provides Airbnb- and VRBO-friendly policies that protect against the specific liability and property damage risks inherent to the hospitality model.
- You are a Fix-and-Flipper: You need to secure "Builders Risk" or "Vacant Property" insurance instantly to satisfy a hard-money lender and start renovations. Obie’s instant-quote technology allows you to go from quote to covered in minutes, ensuring insurance never delays your closing.
- You are an Out-of-State Investor: You are buying properties across multiple markets and don’t want to manage a different "local agent" for every zip code. Obie’s national digital footprint allows you to manage a diverse portfolio across all 50 states from a single, centralized dashboard.
- You are a Multi-Family Investor: You are scaling from single-family homes to 5+ unit buildings and need a broker who can handle commercial-grade complexity without the slow turnaround. Obie bridges the gap by offering the speed of a tech platform with the underwriting depth required for larger apartment complexes.
- You own a Portfolio: You are tired of tracking 12 different insurance renewal dates. Obie’s Master Policy consolidates everything into one bill.
- You are a PropTech User: Obie is "embedded" in platforms like Baselane, Awning, and Visio Lending. You can often get a quote directly inside your banking or lending dashboard.
Obie might NOT be for you if:
- You want to bundle: Obie does not sell auto or life insurance. You cannot bundle your personal car with your rental property for a discount.
Is Obie Legit? (Safety & Solvency)
This is the most common question for any fintech company. Is my money safe?
- The Structure: Obie is an Insurance Provider, not an insurance carrier. They draft policies for massive, global carriers.
- The Carriers: Obie partners with A-rated industry giants like Markel and MSI.
- The Verdict: Your policy is backed by the balance sheets of multi-billion-dollar insurance firms. Even if Obie were to close its doors tomorrow, your policy would remain valid and active with the underlying carrier.
Obie vs. Traditional Brokers
Ready to Experience Obie Difference?
Obie has done for landlord insurance what Rocket Mortgage did for home loans: they digitized a painful, analog process. For the modern real estate investor who values speed, data, and efficiency, Obie is the new standard.
Get a bindable quote for your rental property in minutes with Obie.
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