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Helping You Pursue Your Best Life.

Life is about the pursuit of happiness, not worrying if happiness is achievable. This is why we work tirelessly to oversee and anticipate your financial needs, so you can focus on your career, your family and doing more of what you love.

Discover What We Offer

Experience Freedom By Design

At Water Street Financial, we believe in the power of goal-oriented financial planning
to turn your life’s possibilities into probabilities.

Our Team Takes Great Care To…


Dissolve Your Mental Stress

By monitoring your financial picture on an ongoing basis, we take the responsibility off your shoulders.


Clarify the Investment Process

And the industry as a whole. We’re dedicated to demystify investing, walking you through your options, and collaboratively carving out a path you’re comfortable with.


Be Your Go-To Resource

If you have a question or need to discuss a change, we’re here to offer coaching and decision-making guidance as your life evolves.


Build a Personalized Plan

As an independent, fee-based firm, we’re not beholden to certain products or strategies. Your vision guides us in crafting a comprehensive plan entirely tailored to you.

We put your story at the forefront of our work.

Understanding how you want your next chapters to unfold is a cornerstone of our practice. We then apply our combined 90+ years of experience to develop a strategy oriented towards your dreams. Through continual monitoring of your plan and investments, keeping you on track is our goal.

Whether you are...

Older Couple

Retired or Soon To Be

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Women in bakery

A Business Owner

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family in field


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Doctors in hallway

An Executive or Physician

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...we can help.

What's your risk profile?

Gain Control of Your Financial Destiny
With Us By Your Side

Meet Your Advocates

Ryan Oates, CFP® Photo

Ryan Oates, CFP®

Managing Partner
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Ryan Oates

Ryan Oates, CFP®, MBA, CPFA

Managing Partner

As a founding member of Water Street Financial, I focus on working closely with high net worth financial planning clients, the growth and expansion of our firm, and work with Tommy to oversee the firm’s retirement plan division.

Because of my passion for what I do, I’ve spent my entire career in the financial services industry. Before founding Water Street Financial, I spent over 5 years with First Bank Wealth Management along with my partner, Chris Cotterell. During our time at First Bank, Chris and I worked together to grow the private client segment of the division and expand the bank’s offering to its clients.

I earned my bachelor’s degree in finance from George Mason University in 2002 and my MBA from Shenandoah University in 2017. I obtained the CFP® designation in 2020 to enhance my focus on providing exceptional financial planning to my clients. I’m also a Certified Plan Fiduciary Advisor (CPFA) meaning that I am targeted towards providing fiduciary advice to retirement plan clients. I also hold FINRA series 7 and 66 licenses through LPL Financial along with life and health insurance licenses.

Outside of the office, you can usually find me at the golf course or enjoying outdoor activities with my wife Raychel and our son, Tyler. My passion is to travel and I especially love traveling to play golf around the world. I most recently went to Scotland and Ireland and am planning to go back again soon.

Chris Cotterell Photo

Chris Cotterell

Managing Partner
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Chris Cotterell

Chris Cotterell

Managing Partner

As a founding member of Water Street Financial, I’m responsible for investment strategies and portfolio construction, as well as working with individual clients and overseeing the individual client side of the firm.

I have gained over 25 years of experience in the financial services industry, and I started by spending over 8 years working at First Bank Wealth Management along with my partner, Ryan Oates. I worked with Ryan to expand both the private client segment of the division and the bank’s offering to its clients.

In 1989, I received my bachelor’s degree of science from Slippery Rock University. I hold the designation of Certified Funds Specialist along with the Series 7, 63, 66, 9 and 10 securities licenses through LPL Financial and life and health insurance licenses as well.

In my free time, I enjoy spending time with my wife Julie and our daughter, Peyton. I’m also on the Board of Directors for Our Health.

Angela Morrison Photo

Angela Morrison

V.P. of Operations
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Angela Morrison

Angela Morrison

V.P. of Operations

As the V.P. of Operations here at Water Street Financial I strive to make our process with clients as seamless as possible. Day to day, I work on managing operations, onboarding new employees and developing and maintaining procedures to ensure a positive client experience, combining best practices and available technology. I’m also responsible for implementing and sustaining compliance procedures and training and supervising administrative staff.

I have almost 20 years of experience in the financial services industry. Before joining the Water Street Financial team in 2016, I spent 8 years with First Bank Wealth Management, along with Chris Cotterell and Ryan Oates. I actually worked with Chris Cotterell at another local investment firm as well, prior to joining First Financial Advisors of First Bank.

In my free time, I enjoy being with my family, cooking, watching old movies and am also an avid fan of Lucille Ball.

Jeff Reid, CFP® Photo

Jeff Reid, CFP®

Director of Wealth Management & Financial Planning
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 Jeff Reid

Jeff Reid, CFP®

Director of Wealth Management & Financial Planning

Financial planning for you is at the core of what I do as the Director of Wealth Management. My position also focuses on the future growth and expansion of our firm while also overseeing the entire financial planning division.

I’ve spent the past 18 years in the financial services industry, with over 10 years of experience with Schwab and Scottrade prior to joining Water Street Financial. Most recently, I worked as a manager of financial planning with an advisory firm in Colorado.

In 2002, I earned my bachelor of arts degree in economics from Colorado College. I later obtained the CFP® designation in 2010. I hold FINRA series 7 and 66 licenses through LPL Financial as well as life and variable insurance licenses.

In my free time, you can find me taking part in family activities, camping, golfing, one-wheeling and doing my best to add more to the world than I take.

Thomas Stine, CFP® Photo

Thomas Stine, CFP®

Director of Retirement Plan Services
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Thomas Stine

Thomas Stine, CFP®

Director of Retirement Plan Services

I take pride in the work I do with our financial planning clients, as I help them to live their best possible life with their current means. I also work with retirement plan sponsors to navigate complex rules, regulations and laws of ERISA and the DOL in designing plans, including participant financial wellness.

My designations include the CERTIFIED FINANCIAL PLANNER™ professional (CFP®) designation, the Accredited Investment Fiduciary® (AIF®) professional designation and the Profession Plan Consultant™ (PPC™) designation, which signifies a commitment to education and service excellence in the qualified plan industry. I also graduated from the 401(k) Service Training Program™ which addresses the service standards in the retirement plan industry and imparts professionals not only with the knowledge, but the tools needed to meet and exceed those standards. Lastly, I achieved The Certified Plan Fiduciary Advisor (CPFA) credential from The National Association of Plan Advisors, an affiliate organization of the American Retirement Association. The CPFA was developed by some of the nation’s leading advisors and retirement plan experts and demonstrates knowledge, expertise and commitment to working with retirement plans.

My wife, Tina, and I are active and lifelong members in the Winchester Community. I volunteer my time with many causes and hold a position as a senior board member of the Judges Athletic Association. I’m also an avid supporter of my college alma mater, James Madison University.

Tommy Stine is solely an investment advisor representative of Water Street Financial, and not affiliated with LPL Financial. Any opinions or views expressed by Water Street Financial are his/her own and are not those of LPL Financial.

Corbin Sutton, CFP® Photo

Corbin Sutton, CFP®

Wealth Manager
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 Corbin Sutton

Corbin Sutton, CFP®, MBA

Wealth Manager

As a Wealth Manager, I spend my time creating and maintaining financial plans as well as developing ways to secure the future growth and expansion of the firm. However, my primary focus is working with individual clients.

I’ve spent the past four years in the financial services industry. Prior to joining Water Street Financial, I worked with Sterling Financial Partners, Inc. in Ashburn, VA for over two years, I focused primarily on financial planning and client service during my time there.

I received my MBA from Shenandoah University in 2018 and my bachelor of arts degree in psychology from DePauw University in 2001. During my time at DePauw, I played NCAA college soccer and served as a team captain during my senior year. I now hold FINRA series 7 and 66 licenses through LPL Financial as well as Virginia Life, Health, and Variable Insurance licenses.

I love to travel internationally and spend time outdoors, camping and hiking. I’m also a devoted Oklahoma Sooners football fan.

Caleb Fry Photo

Caleb Fry

Financial Planner
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Caleb Fry

Financial Planner

Caleb graduated from the University of Akron in 2021 with a Bachelor’s in Financial Planning. Over the course of his college career, he had the opportunity to intern with various financial organizations in the corporate and personal wealth planning fields. Following graduation, Caleb gained valuable planning experience with another firm before accepting an offer with Water Street Financial. He holds a FINRA Series 7 through LPL Financial and Series 66 license through Water Street Financial, as well as a Life and Health Insurance license.

In his free time, Caleb enjoys running, reading, and staying active with friends. Being relatively new to Virginia, Caleb and his wife are frequently exploring new activities in the area. He is very excited to join the team at Water Street Financial and adding value wherever he can. Planning for families and individuals is something that Caleb thoroughly enjoys and believes Water Street Financial provides a great opportunity to do just that.

Dru Dearing Photo

Dru Dearing

Client Relations Associate
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Dru Dearing

Dru Dearing

Client Relations Associate

As Client Relations Associate, I’m responsible for supporting clients through every stage at our firm. From account opening and maintenance to scheduling client meetings, I strive to make our clients feel as comfortable and informed as possible. Internally, I also maintain our contact relationship management software and assist with event planning and implementation.

I joined Water Street Financial in June of 2016. My experience with account opening and account maintenance allows me to prioritize an abundance of tasks at the office. Everyday, I’m able to gain knowledge in a variety of financial disciplines to add onto my skills in organization, prioritizing and multitasking.

In my free time, I enjoy spending time with family and friends, trying out new restaurants, and I vacation in Florida every chance I get. I graduated from John Handley High school in 2013 and am a lifelong resident of Winchester.

About Water Street Financial

The Beginnings of Our Firm

Water Street Financial was founded by Chris Cotterell and Ryan Oates on January 1, 2016. Prior to its formation, Chris and Ryan ran the investment division of First Bank also known as First Financial Advisors from 2008 until the formation of Water Street Financial.

During their time at First Bank, Chris and Ryan built the business segments of high-net-worth individuals, corporate retirement plans and institutional/endowment accounts. In October of 2015, they agreed to terms with First Bank to purchase the investment division and separate on amicable terms.

Chris and Ryan started Water Street Financial to create a unique client experience and help people throughout their life journey. They envisioned a client experience that would be truly impactful to not only their clients lives, but those connected to them.

Water Street has since grown and continues to blend a strategic, goal-focused approach with personalization to your particular needs.

Here Are a Few Things That Characterize Us:



Advice customized to you and in your best interest.



A legal commitment to your best interest at all times.



A personalized experience and direct access to us when you need it.



90+ years of combined experience to take care of your financial life.


Partnering with Us

Our process always starts by learning about our clients’ lives and/or professional and institutional goals. We then design a plan and investment strategy around those goals. As a firm, our main priority is bringing ease and comfort to your life. We believe in complete customization and incorporating a team approach to achieve this.   

Secure Your Financial Future With Us By Your Side

Explore How We Can Help

Thoughtfully Aligning Your Financial Strategy
with Your Life Vision

During retirement, you want to enjoy life without worrying if you have enough.

As your partner, our team takes the responsibility off your shoulders. We optimize your path forward by...

  • Creating a retirement plan and closely monitoring it over time
  • Identifying key ways to minimize your tax liability
  • Protecting your family legacy while maximizing it today
  • Partnering with your estate planning attorney

Make the Most of Your Retirement

We’ve all experienced the underlying stress that money can cause. In your golden years especially, we strongly believe you should be able to live your life fully—without nagging financial concern. Our goal is to relieve this burden by building and maintaining a financial landscape that protects you, your family and your legacy.

Start the Conversation

With us as your personal CFO, you can focus on running your business.

We’ll create and oversee your personal and business financial strategy, which includes...

  • Bridging your business’s success with your personal financial future
  • Establishing buy/sell agreements
  • Identifying insurance solutions
  • Creating and managing a 401(k) for you and your team
  • Taking care of your key employees

Let Us Turn Your Financial Complexity Into Opportunity

As a small business ourselves, we recognize the challenges you’re up against. Specializing in financial services for business owners means we do everything we can to help attain outcomes that reflect the work and time you’ve put into building your business.

Let’s Chat

As a successful professional, your future depends on making the most of what you earn now.

Whether you are a c-suite executive, a physician or you operate your own practice, your needs require more advanced techniques. By strategically saving, investing and planning during your high-earning years, we help you support your family now while preparing for the years ahead.

Creating the Roadmap Towards Your Life’s Goals By…

  • Minimizing your taxes
  • Developing an estate plan & collaborating with your attorney
  • Constructing and overseeing your investment portfolio
  • Navigating stock options and benefits
  • Protecting you, your family and your resources

Intentionally Manage the Rewards of Your Hard Work

We always begin our process by talking through your situation and the dreams you hope to bring to life. With a full understanding of your vision, we create a plan personalized to your family. Through ongoing partnership, we help ensure your finances remain robust, even if your life changes.

Schedule Time to Talk

Supporting your family means thinking ahead.

Our team will get to know your family’s short-term needs and long-term goals, helping you…

  • Create a financial plan that balances current and future ambitions
  • Build and overseeing your investments
  • Minimize your tax liability
  • Create a legacy and estate plan & partner up with your attorney
  • Identify solutions to protect you, your loved ones and your resources

Bringing Focused Purpose to Your Family's Finances

As a successful individual who has built significant wealth, you’re often left without the time to address the details of protecting and continuing to grow your wealth. We partner with you to create a plan that meets your family’s needs today while helping you take advantage of opportunities for greater future success.

Get Stated

Liberation Comes From Knowing You’re on the Right Path With a Steadfast Partner to Guide You

Getting Started With Water Street Financial

When you partner with us, you’ll be guided through a thoughtful process to define your vision. Our job is to purposefully allocate every single detail of your finances so you can pursue your ideal future.   


Introductory Call

In an initial call, you’ll let us know what financial concerns are on your mind, and we’ll explain more about how we work. This allows us to see if we’re a good fit to work together.  

Schedule Your Call  


Discovery Meeting

This meeting is entirely focused on getting to know all about your family situation, your thoughts about money, your goals, your dreams—and how you ideally envision your golden years.   


Establish a Relationship  

At this stage, we’ll define roles and expectations. In order for our partnership to flourish, we believe that making clear commitments on both of our ends is key.   


Plan Presentation

We’ll present various plans designed to lead to your desired outcomes. Together we’ll walk through all of your options and the implications of each. We always take a collaborative approach, so you’ll be able to choose the path that works best for you.   


Ongoing Monitoring

Throughout the years, our team will regularly monitor your progress. We’ll have regular meetings to discuss life changes, make sure you’re on track, and update your plan as necessary.  

Instilling Confidence in Your Financial Life Starts Here

Reach Out to Talk

One All-Inclusive Fee Covers ALL Of These Services: 

  • A dedicated financial advisor 
  • A dedicated member of our financial planning department
  • Portfolio construction and management
  • Performance reports
  • Custody and trading
  • Online access to portfolio data 

Advisory Fee Overview


AUM Percentage

First $500,000


Next 1.5 million


Next 3 million


Above 5 million


Have a Question About How Our Fees Work?

Let’s Chat

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From individuals in retirement to those still in their career stride, we’re dedicated to helping you live meaningfully. To connect with us, schedule a call or fill out the form below.

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