Health & Wellness Coverage Built for Independent Professionals
As a 1099 contractor, we know the freedom of building your own path. Finding reliable, comprehensive health coverage shouldn't be a source of stress. We understand the unique challenges independent professionals face, and we're here to offer a trustworthy, straightforward solution.
- Simplified Issue — answer a few health questions to qualify
- No annual open enrollment — apply year-round
- Health, Dental, Vision & Telehealth available
- Coverage for you and your family
Coverage Designed for Your Lifestyle
We provide access to top-tier nationwide group health plans through the Blue Cross Blue Shield (BCBS), PPO, and HSA-PPO options — so you get great coverage at rates without the resale.
Major Medical
In-Network coverage including doctor visits, hospital care, and major medical events.
Virtual Care & Telehealth
Access primary care and behavioral health providers from anywhere, 24/7.
Dental Coverage
Access to a network of dentists for preventive and advanced dental care.
Vision Coverage
Coverage for eye exams, glasses, and contact lenses.
Prescription Drug Benefits
Generic and 90-day home delivery options for your medications.
100% Preventive Care
Full coverage for the preventive screenings and immunizations you need.
Getting Covered is Simple
Schedule a Consultation
Book a free call with our team. We'll walk you through your options and answer any questions.
Answer a Few Health Questions
Our Simplified Issue process means no traditional underwriting — just a handful of questions to match you with the right coverage.
Get Covered
Choose your plan, enroll, and start using your coverage. No need to wait for open enrollment — apply year-round.
Flexible Plans for Every Budget
Whether you need comprehensive, low-deductible coverage or a tax-advantaged HSA plan, we offer multiple tiers so you can find the right fit. Coverage is available for Member Only, Member + Spouse, Member + Children, and Full Family plans.
Traditional Co-Pay Plans
Predictable co-pays for doctor visits, specialists, and prescriptions. Great for those who want simplicity.
Low-Deductible PPO Plans
Lower out-of-pocket costs with access to the broadest provider networks for both familiar and frequent care.
HSA-Qualified Plans
Tax-deductible plans paired with a Health Savings Account. A strong, low-cost way to manage your wellness and finances.
The Hollowtree Health Team
Guy Livingstone
Managing Partner
Guy is an experienced and licensed insurance agent and the founder of Hollowtree. He has an MBA from the Foster Business School at Columbia Business School. In his free time, Guy and his two children live in Darien, CT.
gl@hollowtree.us
Alexander Palase
Managing Partner
Alex is a Managing Partner at Hollowtree. He is a licensed insurance broker and former corporate finance lawyer. He earned his undergraduate degree at Cornell University. Outside of work, he and his wife and their children live in Darien, CT.
ap@hollowtree.usOur health plans are offered through a group plan structure via Population Science Management (PSM). As part of enrollment, you become a working member of PSM and use the Group Plan Application of Initial Member to manage your coverage and complete associated services. This structure is what allows us to offer group-rate pricing for independent contractors.
Health & Wellness Plan
Frequently Asked Questions
Have a question? We have answers. If you have a question that isn't answered here, use the link above to book your consultation.