Be Your Own Boss — with Benefits!
Bringing Community, Tools, and Wellbeing to Solo and Small Business Owners
We’ve been there.
The feast-or-famine paychecks. The late-night Googling for health plans. The guilt of taking time off — because if you’re not working, you’re not earning.
We’re solo and small business owners, too. And we realized something: independence shouldn’t mean going it alone.
That’s why we started Guilds with Benefits — a collective approach to care, community, and support. It’s what we always wish existed, so we are building it together- one Guild Member at a time!
Whether you’re a tattoo artist in Portland, a mobile app developer in Vancouver, or a fitness instructor in Bend, you deserve support.
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“I started Guilds with Benefits after a friend, hair stylist, and mother of two tragically lost her spouse. On top of her grief, she was forced to worry about how she might afford health insurance on her own since she was on her spouse’s plan- and that broke my heart!
As a freelancer myself, I’ve also worried about what I might do in a situation like this, so I built Guilds with Benefits to give people like me and my friend some options. I believe the ability to access your own health insurance when you need it is where true independence comes from- not being forced to rely on an employer or a spouse.
And we’re going way beyond just health insurance. We have retirement plans, EAP Benefits, a membership directory, and connection to each other both virtually and through quarterly in-person events, because- let’s be real- independent work can get lonely!”
— Hollie Miller, Founder & CEO
#independentbutnotalone
New Member Timeline
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RIGHT NOW
Get your business on our Member Directory
Access full EAP Benefits for you and your family
Connect with other Guild Members via our Guild Community Discord page
Set up your retirement plan
Complete our Health Insurance Census form for first access to our plans
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September 1, 2025
AI-Powered Tools designed exclusively for Guild Members go live
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December 2025
Health Insurance Rates and Plans will be available for review.
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January 2026
Open Enrollment for Medical, Dental, and Vision Plans
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February 2026
Annual Election of Guilds with Benefits AHP (Association Health Plan) Board Members
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March 1, 2026
Health Insurance Plans are slated to begin on March 1, 2026
How Joining GwB works
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1. Register
Enter your information in the form on the Join page.
When you submit the form, you will be taken to a new page to select your Guild Membership plan and register your online account. -
2. Activate
Once you’re in the member portal, you can:
Create your business Directory listing to get discovered by new clients/customers.
Access all EAP Benefits, including FREE licensed professional counseling for you and your immediate family.Set up your 401(k) or Solo(k).
Join the Guild Community Discord to connect with other Guild Members.
Get to know local Guild Members by attending quarterly, in-person, no pressure celebration events.
If you complete the health insurance section of the join form, you will have first access to our medical, dental, and vision plans. (By entering your information, you are under no obligation to join the insurance plans.)
Access new GwB exclusive tools and discounts.
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3. Share
Our community grows stronger with every new Guild Member. If you find value in our community, please share us with a friend.
Access to benefits like ours shouldn’t be kept secret!
Our Mission
To provide solo and small business owners with access to community, tools, and affordable benefits so they can thrive independently without going it alone.
Our Vision
To become the trusted home for solo and small business owners by offering curated tools, peer support, a business directory, and access to health & retirement benefits through a membership platform that enhances every aspect of running their business.