Why Oakstone

Meet the people behind Oakstone.

We're not a call center or a quote machine. We're local insurance professionals who work with businesses to find coverage that actually fits how they operate.

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Real people. Local perspective. Independent options.

Ysha and Jarrod, the advisors behind Oakstone Insurance Group

You shouldn't have to wonder who is behind your insurance.

Oakstone was built around a simple idea: business owners deserve an insurance advisor who knows their name, understands their business, and is willing to pick up the phone.

We're independent, which means we're not tied to one insurance company. We can shop the market and help you make an informed decision about what makes sense for your business.

Independent — we shop multiple carriers
Bilingual — English & Spanish
Veteran-owned
Women-owned
Small business focused

The advisors

Insurance is personal. Your advisor should be too.

Ysha Bass

Partner / Insurance Advisor

Commercial Insurance • Small Business • Risk Strategy • Real Estate • Marine

“I redirected my career to insurance because I wanted to make something that can feel complicated a little easier for business owners.”

My background

Ysha wanted Oakstone to give small business owners a different kind of insurance experience — one built on plain language, honest advice, and making each person feel that they aren't just another policy. She works directly with owners from their first quote through every renewal. From owning her own real estate portfolios thru the years, becoming a restaurant proprietor of several local establishments and serving on local boards in the community, she brings real life experience and advice to her clients.

I specialize in

Restaurants
Contractors
Real Estate
Nonprofits
Retail
Professional Services

Something you should know about me

A small-business owner at heart, Ysha knows what it means to sign the front of the checks — not just the back.

Connect with Ysha

Jarrod Prince

Partner / Insurance Advisor

Commercial Insurance • Personal Home & Auto • Client Service • Food Trucks & Events

“When something goes wrong, you should know exactly who to call — and trust that they'll help you.”

My background

A veteran and longtime service professional, Jarrod brings a service-first mindset to every client relationship. He focuses on making sure businesses are protected before they ever need to file a claim. His background consists of over 15 years of experience in the food industry including running his own regional food truck fleet to large music festivals, to BBQ Pitmaster competitions and opening up restaurants. He has served in local and regional event organizations, and also currently runs national Hazmat, CDL, and trucking industry carriers across the US.

I specialize in

Commercial Insurance
Food Trucks
Transportation
Hazmat & CDL
Events
Portfolios

Something you should know about me

Jarrod's military background shapes how he works: show up prepared, do what you say, and look out for the people counting on you.

Connect with Jarrod

Local businesses. Insurance that gets how you work.

We work with the businesses that keep communities going — and we understand them because we're part of the same community.

Food Trucks
Contractors
Restaurants
Retail
Professional Services
Commercial Auto
Commercial Property

Proudly serving businesses with real dreams and goals behind them.

Short answers, straight from us.

Soon you'll find quick videos here from Ysha and Jarrod answering real questions business owners ask — like “Do I really need business interruption insurance?” No scripts, no jargon. Just straight answers.

Let's talk about your business.

Answer a few questions and a real person — not a call center — will help you find coverage that fits.

Start your quote Call 888-754-8868