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Our Mission

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Jim Flynn CFP®

Managing Partner & Founder 

I grew up in the small, coastal town of North Kingstown, RI and the son of two hard working and dedicated parents.  Being a middle-class kid in the late 70s, early 80s meant being a part of the community and being practical. My father was my first role model. He always worked multiple jobs and many days my brother and I stayed up past our bedtime just to see him for a few minutes after he got home from a long day of work. Even with that schedule he still found time to do all the yardwork and coach soccer and little league.  My Dad, being one of 8 kids, was never in a position to take a lot of risk within his profession but his subtle nudging and being a provider allowed me, later in life, to take some career risks he was never able to take.  While investing wasn’t common amongst the families I grew up with, I often wondered about how good my father would have been at it if he had the opportunity. His famous “pay now or pay later” speech still to this day resonates with me.

            My parents made a great team.   My mother exemplified that era growing up as going out to a restaurant was a rare treat and many weeks, she managed to spread out that Sunday meal into Tuesday! She was also by biggest cheerleader when I played sports and my biggest advocate during my schooling.  I’ll never forget the one year when she felt I was overlooked for an Honors Math class and she fought tooth and nail with the school to make sure I was back in that class and had that opportunity. She was also always there for me in my early adult life. She provided unconditional support as jobs took me to faraway places and many nights, I would call home a bit homesick.  That unconditional love and support laid the foundation for me to be a good father later in life.

            Money and investing weren’t often discussed in the home growing up. I’m sure my folks worried about these topics like most folks did back then, but as kids we never sensed we were lacking in any way. It was at Boston College when I first began my love affair with finance and investing money.  One day Peter Lynch, the famous BC alum and head honcho at Fidelity Investments spoke to us Finance majors and that speech changed my life. After that I tried to read every book  I could find on the stock market and personal finance.

            After college my passion for investments took me all around the country as I delivered investment seminars in Florida, Texas, Oklahoma and Washington DC.  It was only after sitting down with hundreds of people, did I begin to see just how important all areas of financial planning have become. So many people I came into contact with needed help with generational planning, college planning, estate planning, understanding the role of taxes just to name a few. This need to help families in all areas of finance inspired me to obtain the distinguished CERTIFIED FINANCIAL PLANNERtm certification in 2012.

            This was also around the time that my personal life began to fall into place.  Marrying my best friend, Jennifer in 2011 was the best decision I ever made.  Her support at that time when the hours were long and there were a lot of ups and downs gave me the confidence to keep building my practice and being excited about our future together. Further motivation arrived a year later, when in 2012, I became a Dad myself as my Conner arrived that August.  We became a family and around the time Conner was walking and talking, we were blessed to welcome his kid brother, Anthony to the world in 2014.

            Having two boys, and following in the footsteps of my father, I am very active with local youth sports. Currently I am the Tee Ball Director for the Pawcatuck Little League. I love coaching the great game of baseball to the kids in our town.  The joy of seeing a 5 year old make their first catch and get their first hit never gets old!  With a full schedule of little league, youth soccer and flag football, in addition to our kids now in school, Stonington, CT just felt like our permanent home.  It only made sense to open Mainsail Capital Management just down the road in scenic Mystic, CT.  Maybe one day, my boys will want to go into business with me, which would be the first family owned business along my ancestral tree!

            Last but not least, last year my small business in Mystic added a new partner, our half beagle half chihuahua Max! Jen was able to save this little guy from a rescue in South Carolina and he has been so much fun. The boys are crazy about him and many days he keeps me company at the office.


Mainsail East

12 Roosevelt Avenue, Mystic, CT 06355

Call: (860) 980-3666

Email: [email protected]

Fax: (860) 318-2099








Rance Hillier CPM®

Financial Advisor

I grew up in a rural town in upstate New York.  Early on, I was taught the lessons of hard work, honesty and accountability that I leverage in my personal and professional life today. 

Family has always been very important to me.  Following a long day at work, my dad always made time to throw the ball, shoot hoops, or volunteer as a coach on the athletic fields.  I owe my competitive drive, accountability, appreciation, and desire to volunteer my time on the fields of sport to his constant involvement in my childhood. 

I was blessed to have my mother home during my early childhood.  She fostered an atmosphere of compassion, patience, and independence that served me well as a child and now as a father to my own two children.   I am so appreciative to my parents who sacrificed in so many ways for the benefit of our family. 

My independence and sense of wonder led me to Connecticut, following my graduation from Siena College in 2000.  Siena provided me with a tremendous education and the opportunity to play Division 1 football.  Football instilled the values of team work, drive, determination and respect.  I am a firm believer in the life-lessons that sports provide. 

Shortly after settling into my first job, I was lucky enough to meet my wife of over 18 years.  Ashley was critical in the start of my career as a Financial Advisor and has been extremely supportive ever since. 

In March of 2007, Ashley and I were blessed with the birth of our son, Caden.  Caden is an athletic and competitive kid who loves football and baseball. 

More than 5 years later, Ashley and I were honored to adopt our daughter, Perry.  Perry is our little flower-child, filled with wonder, creativity, and love.  She enjoys soccer and gymnastics. 

In 2011, I earned the prestigious designation of Certified Portfolio Manager from Columbia University, which provides my clients with enhanced asset allocation, portfolio construction, and investment selections while working with a Fiduciary Portfolio Manager. 

After some tough negotiations from Caden and Perry, we welcomed Bo (goldendoodle) to our family in 2019. 

Outside the office, I donate my time to coaching and enjoy golf, scuba diving, travel, and yard work.  In 2020, Ashley and I founded The Mainsail Foundation to further our family’s charitable giving goals.

Mainsail West

149 Durham Road, Suite 30, Madison, CT 06443

Call: (203) 689-5468

Email: [email protected]

Fax: (203) 738-1181