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Kevin Caldwell

Serving business owners, liveaboard cruisers, and other successful professionals

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Contact Me
Islands East Advisors Kevin Caldwell
Chester, MD

Serving Clients Nationwide

Serving business owners, liveaboard cruisers, and other successful professionals

(833) 303-3278

Website

Areas of Focus

  • Employee Benefits
  • Estate Planning
  • Financial Life Planning
  • Investment Management
  • Owning a Business
  • Retirement Planning
  • Taxes

About Kevin Caldwell

Hi, I'm Kevin Caldwell. I was born and raised in southern Pennsylvania, near Gettysburg, and graduated from Penn State University with a Bachelor of Science degree in Accounting.

After graduation I moved to the Baltimore area and began working for large, public companies with increasing responsibility from Cost Accountant to Senior Accountant to Finance Manager and Financial Analyst, and eventually Demand Planner. These industries included Spirits Manufacturing, Nuclear Power, and Specialty Chemicals. While working in these fields full-time, I increased my experience and education in investing while refining my own strategies.

In 2012, when my fiancé moved to Maryland with her children, we relocated to Kent Island. With the kids grown and leaving us as empty nesters, you can find us cruising on our boat, traveling in our RV, kayaking, biking, paddle boarding, attending live music events, and spending time with friends and family when we are not working. I also enjoy fishing and golfing.

My Journey Into Financial Services

I founded Islands East Advisors (IEA) in 2023, stemming from the increasing requests for financial advice from friends and family. The initial step involved managing a retired relative’s investments to prevent the depletion of their funds, contrary to their tax preparer’s warnings. Recognizing a broader need, I formalized my services into a company.

Initially a means to assist friends and relatives in achieving their financial objectives, IEA has expanded to support small business owners and other professionals in all stages of life with both personal and business financial planning.

Subsequently, Islands East Financial Solutions emerged from my experiences with small business owners who faced similar challenges, including limited financial knowledge, inadequate support beyond their tax preparers, and the absence of employee benefits or retirement plans. Many were unaware of their cash flow projections and couldn’t assess their success until year-end tax filings, which often left them in a precarious position. Recognizing the distinct needs and regulatory requirements that were not being met, I decided to establish a separate entity dedicated to these businesses. Thus, Islands East Financial Solutions was created to provide tailored financial strategies and support for small business owners navigating their financial journeys.

Professional Designations

  • Candidate for CFP® certification

Affiliations

  • Fee Only Network
  • National Association of Personal Financial Advisors
  • XY Planning Network

Primary Location

1563 Postal Rd Ste 3B-C2, Chester, MD 21619

Meeting Options

  • Video Conference
  • In-Person
  • Phone
Book Intro Call

Compensation Methods

  • Fee Only
  • Flat Fee
  • Hourly Rate
  • Percentage of Assets Managed

What to expect in the first meeting

Click the 'Book Intro Call' button above to schedule a free introductory conversation. We'll get to know each other and I'll listen to understand your unique circumstances so we can determine the best way to proceed. I look forward to speaking with you.

Offers Investment Management

Yes

About Islands East Advisors

Islands East Advisors helps you live your dream with stress-free financial planning and investment management.

Whether you’re a full-time cruiser, Great Looper, small business owner, or other successful professional, we create strategies that fit your lifestyle.

From retirement income planning to wealth management, we take care of the details so you can focus on what matters most. For business owners, our partnership with Islands East Financial Solutions means complete support for both personal and business finances — combining strategic CFO services with personalized planning. Enjoy your adventures, grow your business, and secure your future with Islands East Advisors.

WHO WE SERVE

Small Business Owners

Small business owners have distinct financial needs compared to traditional W2 employees. Various business structures offer limited liability protection, provided that there is a clear separation between business and personal finances and corporate formalities are observed. These structures often include benefits such as the Simplified Employee Pension Plan (SEP), SIMPLE IRA, or 401(k) which necessitate correct setup and investment management.

A comprehensive financial plan for these owners should assess the business to optimize all available benefits, like Health Savings Accounts (HSAs), health insurance, and other merited employee benefits. For Strategic Business Financial services, please visit our sister company - Islands East Financial Solutions.

Liveaboard Cruisers (Boaters)

Islands East Advisors (IEA) understands the unique needs of people cruising long distances on their boats, whether full-time or part-time. Our boating clients include those living aboard year-round as well as seasonal cruisers, with many preparing for or actively navigating the Great Loop, the Caribbean or the ICW.

We understand the complexities of the mobile lifestyle - from managing assets remotely to planning for long-term cruising - and provide strategies that align with both personal and nautical goals.

Successful Professionals

Islands East Advisors (IEA) and primarily caters to the unique needs of small business owners and liveaboard boaters. However, the firm extends its services beyond this group, with a significant number of clients coming from various professional backgrounds.

IEA is inclusive and offers detailed financial and investment guidance to all professional households seeking such expertise.

Education

Penn State University, Bachelor of Science - BS, Accounting

Hobbies and Interests

  • Boating
  • Cycling
  • Family
  • Fishing
  • Golf
  • Music

SEC Lookup

View Disclosure

Who We Serve

  • Baby Boomers
  • Business Owners
  • Corporate Executives
  • Dual Income Family
  • Entrepreneurs
  • Gen X
  • Intergenerational Families
  • Living in Retirement
  • Travel Lovers

To make Wealthtender free for readers, we earn a nominal monthly fee from financial advisors and firms in exchange for marketing services (including being featured on this profile page), subject to terms of use. This compensation creates a natural conflict of interest when we favor their promotion over others. Wealthtender is not a client of these advisors or firms. Testimonials may not be representative of other clients’ experiences and do not guarantee future performance or success.

Get answers to frequently asked questions regarding the services offered by Kevin Caldwell View Disclosures

FAQs

Why should I work with Islands East Advisors (IEA)?
At IEA, we offer Cooperation, Transparency, and Clearly Communicated Opportunity Costs to develop the optimal plan for you. We understand that a financial plan should encompass more than just finances. For instance, if you're considering early retirement, have you thought about your activities when most of your friends are still employed full-time? We guide you through envisioning retirement, addressing not only the financial aspects but also the quality of life, sense of purpose, and how you'll spend your newfound freedom.
Can you help turn my dream of becoming a liveaboard in retirement into a reality?
Yes. As a lifelong boater who has owned many boats from a 16 ft. bass boat to a 35 ft. Aft Cabin Carver, I have researched the liveaboard cruising lifestyle for years. We help you structure your finances to support full-time cruising - including budgeting, asset management, and contingency planning. How We Serve Boaters
How are you uniquely qualified to support my needs as a business owner?
Not many financial advisors can offer full fractional CFO or business consulting services to help businesses grow. And most Fractional CFO’s cannot offer advisor services. This makes me uniquely qualified to help business owners with all facets of their financials, business and personal. Learn About IEFS

FAQ Disclosures

Please reach us at contact@islandseast.com if you cannot find an answer to your question.