Career timeline · select any milestone
From military service to real estate leadership
Foundation
Raised in a real estate family
I grew up in the Worcester, Massachusetts area in a family built around housing. My father was a homebuilder, my mother was a real estate broker and my uncle was a mortgage lender. I learned early how construction, sales and financing depend on each other, and that understanding still shapes how I lead.
April 2004 to August 2005 · United States Air Force
Airman First Class, Firefighter
I began my military career as an Air Force firefighter with the 439th Civil Engineer Squadron, part of the 439th Airlift Wing under Air Mobility Command at Westover Air Reserve Base in Chicopee, Massachusetts. After Basic Military Training, I completed the 13-week Fire Protection Apprentice Course and earned Department of Defense certifications as Firefighter I and II, Airport Firefighter and HazMat Awareness and Operations, along with Texas Commission on Fire Protection Firefighter Basic and ARFF Basic.
August 2005 to August 2009 · United States Army
Blue to Green: 21E Heavy Construction Equipment Operator
Wanting a larger role, I moved from the Air Force to the Army through the Blue to Green program in August 2005. I qualified as a 21E Heavy Construction Equipment Operator, trained to run bulldozers, graders, scrapers, scoop loaders and excavators for grading, excavation, backfill and site preparation. I served on active duty with the 331st Transportation Company (Causeway) at Fort Eustis, Virginia. I retired honorably from the United States Army on August 27, 2009.
2009
Founded Winslow Homes
I founded Winslow Homes, earned my Massachusetts real estate license and became a Notary Public. The company was built on four principles that still guide it: Honesty, Integrity, Trust and Service.
Growth years
Distressed assets and luxury sales
I built one of the leading foreclosure and distressed property listing operations in New England and represented luxury properties valued above $10 million. At peak, the organizations I led included more than 600 agents and staff. Winslow Homes was voted Best of Central MA for many consecutive years.
2014 to 2018
Bachelor of Business Administration
I earned my Bachelor of Business Administration from Southern New Hampshire University, graduating with military honors while continuing to run the business full time.
2017
Massachusetts Broker and Home Improvement Contractor
I became a licensed Massachusetts Real Estate Broker and a registered Home Improvement Contractor, formally adding construction services to the Winslow Homes platform.
2021
Construction Supervisor and Hoisting Engineer
I earned my Massachusetts Construction Supervisor license and Hoisting Engineer license (1A, 2C), expanding into land development, site work, permitting and full project management.
2022
Four-state expansion and Florida CGC
I became a Florida Certified General Contractor and a licensed broker in Florida, Connecticut and Rhode Island, and relocated our operations to New Smyrna Beach, Florida.
2023
Winslow Homes Publishing
I founded Winslow Homes Publishing and released Only Sharks: How to Thrive in Real Estate. The catalog has since grown to 192 live titles covering real estate, mortgage, licensing and consumer education.
2024
Mortgage Loan Originator
I became an NMLS licensed Mortgage Loan Originator (2426605), adding financing to our services so buyers and builders could work with one team from contract to closing.
Resilience
Rebuilding after a hurricane
A hurricane destroyed our Florida home. Megan and I kept our family steady, continued serving our clients and kept building our business. In construction, a setback means you clear the site and build again. We did exactly that.
Today
Leading Winslow Homes across four states
Today I lead Winslow Homes as Founder, Managing Partner and Managing Broker, directing active real estate brokerage, construction and land development operations across Florida, Massachusetts, Rhode Island and Connecticut. Megan and I co-list our properties and originate mortgages together through The Federal Savings Bank, so our clients get sales, construction and financing from one team. I also run Winslow Homes Publishing, coach agents and industry professionals, and pursue my Master of Business Administration while raising our three children, Jaikob, Jaelynn and Julianna. I am ready to bring this full operating experience to an executive team.
RYAN + MEGAN
