We used to be you.

Paul and Sean retired from the US Navy in 2010 and 2012 respectively. After trying a few things they each started their own independent financial advising firms. That put them on the path to connect in 2017. By the next year, they had realized they were trying to individually build the same type of firm, but with different skill sets. It was the perfect storm. They merged their individual firms to form Redeployment Wealth Strategies in 2018. The growth since then has been inspiring, humbling, and challenging. Fortunately, we were able to find people with the right mix of talent, diligence, and dedication to serve our existing clients while giving us the capacity to propel the firm forward. Each RWS team member has a direct connection with the military. That is not just a lucky coincidence. That's an essential quality to be on this team. Job skills can be learned, but empathy for and knowledge of military culture must be lived. We all talk the talk because we've walked the walk. We look forward to working together to help you achieve your life goals.

Meet Our Team

Click on those smiling mugs to learn more about the team of planners and advisors at Redeployment Wealth Strategies

Sean Gillespie, MQFP®

Financial Advisor

I graduated from the U.S. Naval Academy in 1992 and served in the Navy for twenty years as a surface warfare officer. My education in financial planning began in the spring of 1994 when a Naval Academy classmate who cared enough about my wife and me to not take no for an answer told us, “We’re going to dinner Wednesday night.” Tom routinely chose great restaurants, so we showed up at the appointed place and time without discussion or complaint.

Dinner was unremarkable. Fixed menu rubber chicken fare. Perfectly adequate, just not the over-the-top good stuff we were used to Tom picking out. But the seminar given during dessert changed our lives. In less than sixty minutes, we were shown the simple outline of a financial plan to get us moving in a sustainable fashion toward a comfortable retirement. And afterward, Tom introduced us to the man who would be our agent for twenty years. Dave helped put us on our path to financial independence in 1994 and helped us make the adjustments along the way to keep us on it. And when I retired after twenty years of Navy service, he mentored me into the financial services business.

Among dozens of things Dave taught me over twenty years, two of them were critically important. One of them was the sort of product knowledge that got me credentialed and sufficiently competent to help others identify their own goals for financial independence. Far more important was the spirit of service he exemplified every day. Lots of people talk the “client always comes first” talk. Dave walked it, being just as candid with us when we were on track as when he thought we were getting ready to make a mistake. And we always felt his recommendations were in our best interests. It wasn’t just that his interests were secondary. They didn’t enter into the conversation at all. It was in that spirit that I got licensed in 2013 to help families plan for their own sustainable financial futures.

My wife Jennifer and I have been married since 1992. When I retired, we decided to put down roots in Chesapeake Virginia, in the community where we have owned a home since 2001 and, when not stationed overseas, raised our three daughters.

Izzy Carnes, AFC®, MQFP®

Director of Operations

Before joining the RWS team in 2020, I spent 14 years serving as a financial counselor for a military non-profit organization. Along the way, I earned credentials as an Accredited Financial Counselor® and a Military Qualified Financial Planner®, thanks to the military spouse fellowship opportunity and the tremendous mentorship and support within the military financial professional community. 

When I first joined the RWS team, I was on the path to becoming a CFP ®. My career took a major turn when I discovered my superpower—thriving on the tedious, behind-the-scenes tasks that keep everything running efficiently. My experience as a Lead Planner brings a strong understanding of both how account operations are executed and the strategic rationale behind established processes. I love supporting our planners and making sure every client experience is seamless and positive. 

I’m a first-generation immigrant from Okinawa, Japan, and now call coastal North Carolina home with my retired Marine husband and our two very spoiled miniature schnauzers. I’m an avid reader and food enthusiast, and I love learning new languages – still working on my Spanish and ASL. In my spare time, I am actively engaged in the veterans’ caregivers community, and I’m also passionate about serving our veterans by providing pro bono financial counseling and helping them navigate their financial journeys.

Carol Pittner

Lead Planner

I am a Navy veteran (Surface Warfare Officer), the daughter of Navy veterans, the wife of an active-duty Naval Officer, and the mom of a busy elementary schooler. I earned a B.S. in Civil Engineering from Rice University and grew up in the Financial Independence community. I co-authored the book Raising Your Money-Savvy Family for Next Generation Financial Independence with my father, author and blogger Doug Nordman. My family and I live in Hawaii. 

Cyndi McCaleb

Office Manager

Born in Louisiana and raised in Mississippi, I met my Sailor at Keesler Air Force Base and quickly moved to Virginia Beach. One of our two children is part of the EFMP (Exceptional Family Member Program), so we will be staying here until retirement. I am also a professional photographer, specializing in portraits for families with special needs. I originally joined the PIM Tax Services team as an Administrative Assistant in February 2022. After tax season, I was promoted to Office Manager for RWS.

Angela Cloe, ChFC®

Lead Planner

I’m Angela Cloe, a financial planner with a deep commitment to serving the military community. After retiring from the U.S. Navy in 2024 as a Chief Petty Officer following 20 years of service, I transitioned into my second career with purpose and passion. 

My journey into financial services began in 2014 when I took on the collateral duty of Command Financial Specialist (CFS). Over the next decade, I educated and assisted service members from all branches in personal finance, which sparked my passion for helping others build financial confidence and security. 

Following my SkillBridge internship, I joined the RWS team as the first SkillBridge hire and now work as a full-time planner out of our Virginia Beach home office. I am a registered Chartered Financial Consultant (ChFC®) with American College of Financial Services, I hold a B.A. in Organizational Leadership from Brandman University and am currently pursuing the Certified Financial Planner™ (CFP®) certification. 

I live in Virginia Beach with my teenage daughter, and I’m proud to continue serving those who serve—past and present—by helping them navigate their financial futures with clarity and confidence. 

 

Leo Somera

Associate Planner

I joined the RWS team in late 2025 after retiring from a 20‑year career in the U.S. Air Force. I’m currently working toward becoming a Certified Financial Planner™ professional by 2027 and expect to earn my Investment Advisor Representative license in early 2026. 

My passion for financial education started during my Air Force career. I taught informal financial planning and investment classes for military personnel and even published weekly finance newsletters for my unit during my deployments to the Middle East. Later, while teaching biology at the Air Force Academy, I incorporated financial lessons into my courses to help future officers build healthy financial habits as they entered the Air and Space Forces. 

I began my transition into the financial planning career while still on active duty, taking night classes for two years before completing a DoD SkillBridge internship with RWS. I retired on May 1, 2025, took a short “mini‑retirement” to travel, passed the CFP® Board Exam in July, and officially joined RWS in August. 

These days, I’m embracing life as a digital nomad—traveling the U.S. in my adventure van, visiting family and friends, and continuing my journey toward full licensure and certification. 

Drago Somera

Morale Officer

Hi, I’m Drago — Leo’s four‑legged sidekick and the real brains of this operation. I’m a Lab‑mix rescue with a lot of energy and an even bigger love for road trips. Adventure is kind of my thing. Beaches, grassy fields, wide‑open spaces… if I can run in it, roll in it, or sniff it, I’m happy. 

When Leo’s in town, I like to hang out at the RWS office. I take my duties very seriously: morale officer, security specialist, and professional tail‑wagger. I make sure everyone gets a smile break, and I keep an eye on things — you never know when a suspicious squirrel might appear. 

I’m also a big supporter of financial planning. A good plan means more treats, more toys, and plenty of cozy places for pets like me to nap after a long day of keeping our humans’ homes (and adventure vans) warm and welcoming. So really, I’m just looking out for the whole team. 

Sean and Paul were interviewed for XYPN Radio - the podcast for the XY Planning Network. If you want to know their history, their paths to financial planning, and why & how they want to serve the military community, it's an hour well-spent.

Financial Planning for Military & Veteran Families