How-to

How to Find a Health Plan That Covers GLP-1 Medications Like Wegovy & Ozempic

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Guide
HSAs or HRAs, what is the difference?
HRAs and more

HSA or HRA? Why Small Businesses Are Choosing ICHRA Instead

You've probably heard of HSA and HRA, but do you know how they developed over the years into the small business champion that is ICHRA?

Article
Customer Spotlight featuring StretchDollar customers Pawsitively Perfect
Small Business

Helping Employees Achieve Pawsitively Perfect Help with StretchDollar

Learn how Pawsitively Perfect offers affordable health benefits to employees with StretchDollar, creating a healthier, happier team.

Guide
A stork carrying a baby blank in his mouth
Health Insurance

How to Shop for Health Insurance as New Parents (For You and Your Child)

Becoming a new parents is exciting! Take these steps to make sure your new bundle is covered.

Guide
Hand holding prescription medicine bottle
Health Insurance

How Prescription Coverage Works and How to Save Money: A Guide for Small Businesses

Confused by formularies, copays, or deductibles? Our guide explains prescription coverage and shares tips to help you save on medications.

Article
Person with a megaphone announcing exciting news
Company

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.

Guide
The number 2025 with hands typing on a computer and graph lines representing trends
Health Insurance

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.

Article
3/4 of a pizza eaten with the eaten part representing the amount of taxes required to be paid for health stipend
Small Business

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.

Guide
A sign says Beginniner's guide and a person is giving two thumbs up
Small Business

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.

Guide
An outline of the state of ohio with a sign that reads nonprofits
Health Insurance

The Best Health Insurance for Ohio Nonprofits

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

Article
A document that says health insurance tax deduction with a post that reads Need Help
Small Business

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.

Article
Post it note with a thumbtack that reads "why not"
Small Business

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.

Guide
Outline of the state of Ohio with a highway sign in the middle
Small Business

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.

Guide
Sign that read affordable health insurance next to another sign that reads nonprofits.
Health Insurance

The Best Health Insurance for Small Nonprofits in Texas

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

Guide
An outline image of the state of Florida with a Florida highway sign
Health Insurance

The Best Health Insurance for Florida Small Businesses

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

Article
Four stacks of coins holding the letters F, E, E, and S with an anti symbol on top to represent that StretchDollar's platform is now free.
Company

StretchDollar is Now Free

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

Guide
Outline of New Jersey with a highway sign that says Welcome to New Jersey
Small Business

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.

Report
Two people in business outfit pulling a rope like a tug of war with the word business owner pointing to the middle. 
Health Insurance

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.

Report
Vintage healthcare-related poster for a health insurance history article. Poster reads Danger don't spread disease by finger licking.
Health Insurance

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.

Guide
An outline of California with a Welcome to California sign.
Health Insurance

The Best Health Insurance for California Small Businesses

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

Article
A hand holding up a credit card.
Health Insurance

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.

Article
Illustration of Dolly, StretchDollar's wiener dog mascot facing forward and smiling
Company

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

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

How-to
A pregnant woman smiling. 
Health Insurance

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.

Guide
Outline of the state of Pennsylvania with a highway sign that reads Welcome to Pennsylvania.
Health Insurance

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.

Article
A pencil erasing the word debt. 
Company

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.

Guide
An outline map of Texas with a Texas highway road sign.
Health Insurance

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!

Guide
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Small Business

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.)

Guide
Four employees in aprons with the word franchise written on a chalkboard above them.
Health Insurance

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

We simplify employee health benefit choices 

Article
A finger drawing a line moving upward with the word "costs" next to it to represent rising healthcare costs.
Health Insurance

Employer Health Insurance Costs Jump in 2023

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

Guide
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Health Insurance

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.

Article
Outline of the state of Texas with a road sight that says "texas" and a rocket ship in the corner to represent startups.
Health Insurance

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.

Guide
An outline image of the state of Illinois with a signpost that reads Illinois.
Small Business

The Best Health Insurance for Illinois Small Businesses

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

Article
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Company

StretchDollar Launches

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

Article
A pile of block letters all jumbled up.
Health Insurance

21 Health Insurance Acronyms Explained

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

Article
A balance with the word "myth" on one side and "fact" on the other and in the middle, a cross representing the health insurance marketplace. 
Health Insurance

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.

Article
A red heart is broken in half with a bandaid keeping the two pieces together.
Health Insurance

The Hidden Cost of Group Health Insurance — Discontinuity of Care

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

How-to
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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.

Article
A stack of antique looking books with the title: How ICHRA came to be
HRAs and more

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
An ink stamp that just stamped "approved" over the word "claim" referencing a health insurance bill.
Health Insurance

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
An empty shopping cart with a StretchDollar logo on the front sign of the cart,
Health Insurance

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. 

Article
A one-dollar bill is split almost in half to show what is left after taxes.
HRAs and more

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

Let’s get stretchy with those health benefit dollars.

Guide
The back of a woman's head with her right hand on the back of her head as she looks at two arrows going in different directions for HSA or HRA.
Health Insurance

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

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

Report
A hand holding a yellow report with the title The State of Health Insurance.
Health Insurance

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

Article
A white paper airplane falling downwards with a dotted spiral behind it.
Health Insurance

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.

Article
Someone with two different apples in their hands trying to make a decision like you would for an ICHRA or small group health plan
Health Insurance

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.)

Guide
Someone giving two thumbs up after reading StretchDollar's simple guide about ICHRA
HRAs and more

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. 

Article
StretchDollar logo
Company

Why We Started StretchDollar

And why small businesses need our help now.

Article
A hand holding up four fingers on a green StretchDollar background
HRAs and more

4 Reasons Small Businesses are Turning to HRAs for Health Benefits

More companies are stretching their benefits budget with a fixed, pre-tax option.