Self-Employed? You don’t have to go it alone.
Get large group benefits, peer support, and financial tools — designed for freelancers, solopreneurs, and small business owners… Finally!
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 freelancers 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 financial stability. It’s what we always wish existed, so we built it for ourselves — and now for you!
Whether you’re a freelance illustrator in Portland, a mobile app developer in Bend, or a fitness instructor in Lincoln City, you deserve real support.
This is the safety net we’re building together, one Guild Member at a time.
The Waitlist is open for our first 100 founding members!
Join our FIRST cohort to access our exclusive benefits & skip the health insurance waiting period with a 7/1/25 start date!
Jenni is a travel blogger in SE Portland. She joined Guilds with Benefits to finally get affordable health insurance for her and her partner.
We’re a new type of support, built by and for independent workers — and we’re growing fast! You’ll be among the first to shape what comes next.
We can provide all of this by employing our Guild Members to do what they’re already doing. Guild Members are still responsible for finding their clients, working on their projects, and setting their own prices — freedom & flexibility included!
The difference? Now they have protections and financial stability, access to large group benefits, and their taxes are handled. In some cases, they even take home more money!
Are you still working hard and
Have no 401k or safety net?
Feeling isolated and overwhelmed?
Can only afford catastrophic health insurance plans — or going without entirely?
Avoiding your quarterly tax filings like the plague?
You’re in good company!
I started Guilds with Benefits after hearing of a self-employed mother of two small boys who suddenly and tragically lost her husband. Now, as the sole breadwinner in the home, she was forced to get back to work after only two unpaid weeks off. On top of her grief, she was forced to worry about how she might stay in her home, afford health insurance, and find child care.
This woman’s story broke my heart and inspired the idea for Guilds with Benefits.
As a freelancer myself, I’ve also worried about what I might do in a situation like this. I couldn’t stand the thought that self-employers (a whopping 1/3 of the workforce) have ZERO options for financial security, protections, and safety nets.
I built Guilds with Benefits to give people like me these options.
— Hollie Miller, Founder & CEO
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Our Mission
We bridge the gap between independence and stability, allowing our Guild Members to focus on their passions.
Our Vision
We envision a future where freelance workers can access quality benefits & safety nets typically reserved for traditional W-2 employees, reduce the time and stress of administrative tasks, find community, and share resources. By fostering a culture of collaboration and support, we strive to create a thriving community where everyone can achieve their full potential.
How It Works
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1. Join
You’ll be part of a supportive group that understands what it’s like to be in your industry. Tap into the Guilds anytime to share what’s working, get advice, or pass referrals.
Why it matters: You’re not alone anymore.
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2. Benefit
From actual time off to health insurance to 401(k) plans and more — get access to the essentials. We get large group rates on great plans for you!
Why it matters: You shouldn’t have to pay more or settle for less!
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3. Thrive
You’ll love having quick and easy templates for your client contracts and invoices almost as much as not needing to file your quarterly taxes anymore.
Why it matters: You shouldn’t be wasting time on the little things when you can be doing what you love.