Small business is our specialty
Small businesses and property owners are our whole focus, not a side line.
Insurance made more human
Protect what you're building.
Clear, thoughtful insurance guidance for small businesses and commercial real estate — plus personal home and auto when you need it.
No obligation. No insurance-speak. Just a real conversation.
Small business is our specialty
Serving all 50 states
Chamber & small business partners
Access to top-rated carriers
Small business coverage
Built around the business you run.
No two businesses work quite the same way. Choose your profession and we'll tailor the questions to your work.
Food & beverageRestaurants · Bars & taverns · Food trucks · Coffee shops
Beauty & personal careSalons · Barbers · Nail technicians · Estheticians
Retail & makersBoutiques · Gift shops · Craft booths & fairs · Online sellers
Trades & contractorsGeneral contractors · Electricians · Plumbers · HVAC contractors
Cleaning servicesHouse cleaning · Janitorial · Carpet cleaning · Pressure washing
Fitness & wellnessGyms & studios · Personal trainers · Yoga instructors · Dance studios
Events & entertainmentEvent planners · Wedding planners · Photographers · Videographers
Professional servicesConsultants · Bookkeepers · Real estate agents · Notaries
Auto & transportationAuto repair shops · Detailing · Car washes · Tire shops
Daycare & careDaycares · In-home childcare · Senior care · Pet grooming
Commercial real estate
One property or a growing portfolio.
We help owners make sense of coverage across different asset types, ownership structures, and stages of growth.
Explore protection for rentals, multi-housing, retail centers, mixed-use properties, and portfolios of every size.
Specialized coverage
The risks other agents pass on.
Houseboats, CDL trucking, storage facilities, boutique hotels and Air BnBs, and plenty more. If it feels unusual, it is probably something we have placed before.
Houseboats & marineHull, liability, personal effects on board, and marina requirements for liveaboard and seasonal boats.Start your quote
CDL & transportationOwner-operators, small fleets, hazmat, refrigerated, and flatbed hauling with filings and cargo coverage.Start your quote
Storage units & facilitiesSelf-storage, climate-controlled, and RV or boat storage — including tenant property and lost rental income.Start your quote
Boutique hotels & lodgingSmall hotels, inns, and B&Bs — guest property, food service, events, and seasonal swings all covered.Start your quoteSomething else entirely?
Concessions, nonprofits, farms, vacant buildings, special events — tell us what you have and we will find the market for it.
Tell us about itBacked by the strength of the Smart Choice® network.
Local, personal service with the market access of one of the country’s largest independent agent networks.
- 100+
- Carrier partners we can shop
- 3,000+
- Products available through our network
- $2.5B+
- Premium placed by the network
- 50
- States we can write business in
Carriers we can shop
Top-rated markets, one agency.
Through our Smart Choice Smart Start Commercial access, we can quote your business with well-known national carriers and compare the options side by side.
Carrier availability varies by state, class of business, and underwriting eligibility.
How we help
Insurance advice that feels reassuring.
You do not need to know insurance. We ask the right questions and find coverage that fits your work.
Coverage built for your trade
We tailor the policy to the work you actually do.
Many carriers, one conversation
We compare top-rated carriers so you do not have to settle for one option.
Quick, no-pressure answers
Straight answers from a real person, usually the same business day.
Real people. Local perspective. Independent options.
You shouldn't have to wonder who is behind your insurance.
We're not a call center or a quote machine. We're local insurance professionals who know your name, understand your business, and pick up the phone.
Ysha Bass & Jarrod Prince
“I redirected my career to insurance because I wanted to make something that can feel complicated a little easier for business owners.”— Ysha Bass, PartnerMeet the people behind Oakstone
Reviews
What owners say about working with us.
“Oakstone made insurance feel approachable for the first time. They asked about our salon, our team, and our actual risks instead of just checking boxes.”
Maria R.
Salon owner
“We needed coverage for our food truck fast for a festival. The team explained everything in plain English and had us protected in time.”
James T.
Food truck operator
“As our rental portfolio grew, Oakstone helped us consolidate policies and spot gaps we didn't know we had. Reliable, responsive, and no jargon.”
Elena V.
Commercial real estate investor
Let's talk
Tell us what you're building.
Share a little about your business, property, or household. A real person will follow up for a relaxed, no-pressure conversation.
888-754-8868Not sure what you need?
That is completely fine. Starting with a question is enough.