Blog

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StretchDollar Raises $6 Million to Fix Health Benefits for Small Businesses

We're excited to keep ramping up to help the small business community we love so much.

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Small Business Health Insurance: What to Expect in 2025

The news for small business health insurance in 2025 isn’t rosy, but there is a bright light — a pre-tax, fixed benefit called ICHRA.

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Health Stipends for Small Business Employees: the Good, the Bad, (and the Better Option)

Are you giving employees extra cash for health insurance? It might not have the value you think it does.

New to Health Benefits? A Beginners Guide to Small Business Health Insurance

Searching for health insurance options for your small business team? This guide's got you covered.

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The Best Health Insurance for Ohio Nonprofits

And why a new health insurance benefit option called ICHRA is getting so much interest.

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Health Insurance Tax Deductions Small Business Owners Need to Know About

Is your small business an S-Corp, C-Corp, or Sole Proprietorship? Your business structure determines how you handle this write-off.

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Why You Should NOT Pick StretchDollar for Your Small Business Health Benefits

There are a few situations where your small business SHOULD keep its current health benefits situation.

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The Best Health Insurance for Ohio Small Businesses

Having a tough time finding budget-friendly health insurance for your small business team? Check out this guide.

The Best Health Insurance for Small Nonprofits in Texas

An easy-to-read guide on employee health insurance coverage for smaller-sized nonprofits.

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The Best Health Insurance for Florida Small Businesses

Health benefits can be tricky to navigate, especially for SMB owners. We're here to help!

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StretchDollar is Now Free

Pre-tax health benefits (AKA ICHRAs) are the future. Run yours on our platform for free.

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The Best Health Insurance for New Jersey Small Businesses

Finding health insurance for your team is tough. We simplify it in our latest guide for companies in the Garden State.

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Health Insurance History: How Employers Got in the Middle (Part 2)

How businesses got into the (weird) business of health insurance and an option that’s changing it.

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Health Insurance History: How this Messy System Began (Part 1)

The roots of U.S. health insurance began a century ago in Dallas, Texas. Let's take a look.

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The Best Health Insurance for California Small Businesses

Navigating employee health insurance choices is hard. We simplify it here.

Do Health Insurance Companies Accept Credit Cards for Premium Payment?

Love racking up reward points? These health insurance carriers let you pay by credit card.

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Meet Dolly the Wiener Dog, StretchDollar's beloved mascot!

Dolly is poised to capture hearts with her adorable and stretchy charm.

How to Shop for a Health Care Plan While Pregnant (or Planning to Be)

A few unique tips to factor in when thinking about your care (and health insurance) during this special time.

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The Best Health Insurance for Pennsylvania Small Businesses

Finding reasonable health benefits for your team is a very real challenge. This guide aims to help.

Medical Debt is a Big Problem. Here’s What We're Doing About It.

StretchDollar’s new partnership gives all members access to professional bill negotiation services.

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The Best Health Insurance for Texas Small Businesses

Having a tough time finding budget-friendly health insurance for your team? We’ve crafted this guide just for you!

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The Best Health Insurance Options for Small Businesses with Under 20 Employees

We outline the pluses and minuses of current options, including a new one. (There is something for any budget.)

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Guide to Health Benefits for Franchises (Including a Newer, More Affordable Option)

We simplify employee health benefit choices

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Employer Health Insurance Costs Jump in 2023

We explain the rise in prices and what small business owners can do.

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The Best Health Insurance for North Carolina Small Businesses

You didn't start your small business to be a health insurance expert. We outline the basics here.

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Top 3 Health Benefit Options for Startups in Texas

Finding health benefits can be complicated (as if you have time!) Here are the best options for you and your team.

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The Best Health Insurance for Illinois Small Businesses

Struggling to find affordable health insurance for your team in Illinois? This guide will help.

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StretchDollar Launches

We’re in 7 states today and expect to be in all fifty states by the end of 2024.

21 Health Insurance Acronyms Explained

Understanding healthcare language is hard enough without all those acronyms. We explain the alphabet soup here.

3 Marketplace Secrets that Small Business Owners Need to Know

And how it's helping make a pre-tax fixed health benefit become popular among small employers.

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The Hidden Cost of Group Health Insurance — Discontinuity of Care

How the traditional way businesses have approached health benefits short changes their employees’ health.

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Getting Started

How to Choose a Health Insurance Plan for YOU

Some key questions to ask yourself before jumping into health plan shopping.

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ICHRA History Lesson: How the Pre-Tax Health Benefit Came to Be

Let's go back in time and find out how and why ICHRAs were formed.

How to Appeal a Medical Bill

Appealing a medical bill can seem daunting, particularly if you're unsure where to begin. We unravel the steps here.

How to Choose a Health Insurance Plan for Your Family: A Step-By-Step-Guide

Ace your health insurance hunt for the family with our informative shopping guide.

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Pre-Tax Versus Post-Tax? Maximize Your Health Benefits with this Easy Step

Let’s get stretchy with those health benefit dollars.

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HRA vs. HSA: Which Is Better for Your Small Business?

Confused by the acronyms and what they mean? Get straightforward answers here.

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2023 Small Business Health Insurance Report: Trends and Expectations

A lot of not-so-good news is expected next year. But there is a glimmer of hope

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The Death Spiral of Group Health Insurance

Why group health benefits are facing a big shift, and how a newish option can save the day.

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ICHRAs vs. Small Group Health Insurance

How the hot new group coverage type is changing the health benefits game (written by a benefit nerd for non-nerds.)

A Not-So-Boring, One-Page Guide to ICHRA

Everything you want to know about this lesser-known health benefit option for small businesses in less than 3 minutes.

Why We Started StretchDollar

And why small businesses need our help now.

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