Kevin Caldwell
Serving business owners, liveaboard cruisers, and other successful professionals
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Serving Clients Nationwide
Serving business owners, liveaboard cruisers, and other successful professionals
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 (www.islandseastfinancial.com), a Fractional CFO / business consulting firm, 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
- National Association of Personal Financial Advisors
Primary Location
1563 Postal Rd Ste 3B-C2, Chester, MD 21619
Meeting Options
- Video Conference
- In-Person
- Phone
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 complimentary 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) 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
Volunteer Experience
Tides of Grace American Red Cross
Hobbies and Interests
- Beach
- Boating
- Camping
- Cycling
- Family
- Fishing
- Football
- Golf
- Music
SEC Lookup
View DisclosureWho We Serve
- Baby Boomers
- Business Owners
- Corporate Executives
- Dual Income Family
- Entrepreneurs
- Gen X
- Intergenerational Families
- Living in Retirement
- Remote Workers
- Travel Lovers
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FAQs
FAQ Disclosures
Please reach us at contact@islandseast.com if you cannot find an answer to your question.
