We used to be you.

Each of us served a career in uniform before moving on to become financial planners. And we each sat in the mandatory transition course wondering how we'd trained for our entire careers to perform dangerous tasks and missions with skill and confidence, only to arrive at the end of our careers and be told we should be afraid of everything coming next. The financial aspects of military retirement, in particular, were delivered through a fire hose in a few hours...except for the parts that weren't covered at all. At that point, we each knew what our next mission was, and we each spent the next several years pursuing it separately until meeting in 2017. Not too long after that, we determined we'd be better at it--and our clients would be better served--if we worked together. So now we do.

Meet Our Team of Experts

Sean Gillespie

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.

Paul D. Allen

Financial Advisor

Some people like to do Sudoku. Others like to do crossword puzzles. I like to do taxes. For each tax situation there is one correct solution – the solution that is both legal and most advantageous to the taxpayer. I like to find that answer every time I sit down to prepare a tax return.

I personally believe the tax code should be simplified. Nearly everyone who seeks my services does so because they are struggling to prepare their own return. That’s good for my business, of course, but I don’t think it’s fair to the taxpayers. If paying taxes is required the average citizen ought to be able to figure out how much they owe. However, I do not expect the tax code to be greatly simplified in my lifetime. Honest reformers seem to be in short supply in Washington these days. But I digress…


I was born and raised in Ohio, making me a die hard Buckeye and a long-suffering Browns fan. I enlisted in the US Navy in 1987, was commissioned in 1995, and retired from active duty in 2010. Somewhere in there I managed to find and marry the perfect girl (Tade) and have 3 children (who all turned out quite good looking despite my contribution to the gene pool). During my Navy career I served at sea on submarines, an aircraft carrier, and a high-speed catamaran. Ashore I served tours stateside, in the middle-east, and east Africa. It was a blast, but it was time to move on. I wanted to become a financial planner.

As I was studying to become a financial planner I noticed that most of the instructors were telling us to avoid giving tax advice. That didn’t make any sense to me, because taxes touch every aspect of financial planning. At the same time I was becoming dissatisfied with the prices I was personally paying for tax preparation, so I signed up for a tax class.

Somewhat unexpectedly, I loved it! I wanted to know even more about taxes. I went to work for a nationally known tax preparation firm and continued to learn and study taxes. While I enjoyed the experience and the people I was working with, one thing I didn’t like was the inability to provide great value to ALL of the clients. Too many corporate rules.

veteran tax prep virginia beach

Despite being warned against giving tax advice, I decided to incorporate tax planning and preparation directly into my financial planning business. I always figured if you’re going to do something, you might as well do it right. So, I studied (and studied, and studied) and earned the Enrolled Agent certification from the IRS. It is the highest credential the IRS awards tax professionals. Not only can I prepare tax returns, but I am authorized by the IRS to prepare and deliver written tax planning advice and, if necessary, represent clients at every

level of the IRS, including appeals. (Represent means if the IRS wants to talk to you, you can tell the IRS to come talk to me instead, and I’ll set things right.)

I am aware some folks just want tax preparation, and not full-on financial planning. Therefore I decided to start PIM Tax Services as an independent business from the financial planning firm. It allows me the greatest flexibility to meet the needs of each individual client.