Everything looked over, nothing overlooked.

Our Independent Firm Structure means we are 100% committed to servicing our clients, not shareholders.

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Our commitment to act in your best interest and always PUT YOU FIRST.


Our FEE ONLY STRUCTURE means that we don’t grow unless you do.  No commissions, referral fees, or other hidden costs.


Unparalleled service with complete guidance through every step of your journey.

The Oak Square Difference

Oak Square Advisors Team PictureWith over 25 years of combined experience, we founded Oak Square Advisors with the belief that there is only one acceptable standard of accountability for Financial Advisors: FIDUCIARY. We chose to put our clients interest above everything else and offer best in class, unbiased, non-conflicted financial planning and advice.

We took it one step further and voluntarily filed as a Registered Investment Advisory Firm so that we are held accountable to this Fiduciary Standard under Federal Law. While most of the financial services industry operates as Registered Representatives, Brokers, or “Salespeople” under an obscure suitability standard, we believed that all clients deserved a better option.

So here’s how we’re different:

We are Fiduciaries 100% of the time and are always working in your best interest.

We are a fee only firm because we believe that an advisor is most loyal to who pays them. If you’ve never paid your advisor, then they don’t work for you. They’ve been selling you financial products for whoever is writing their commission check. They have not provided the unbiased, non-conflicted, financial solutions or advice you deserve. At Oak Square, we work directly for our clients. As a client, you pay as you go, but only after we have performed our services. We have complete fee transparency and if at anytime you don’t see value in our work, you can terminate our relationship.

Our fee schedule is based on a percentage of the assets we manage for you. The transparency and simplicity of an asset based fee further aligns our firm with the interest of our clients and allows us focus on managing your assets and financial planning needs.

We receive zero commissions for “sale” of securities. No hidden fees or costs. Again, we work for you. No one else.

Almost all our clients come to us with an existing Advisor relationship. Many from some of the country’s largest Wealth Management Firms. Meet with our team to find out why our clients made the switch.


CALL US TODAY AT (407) 599-2300 to start a conversation.  Or, If you prefer, click on any of the “Book Now” buttons below to easily schedule your complimentary 90-minute initial consultation to sit down with our Founder, Danny Gay, AIF®, or Co-Founder, Josh Rose, AIF®.  We have offices in Winter Park, Sarasota, and Jacksonville (or we are happy to speak with you by phone or video conference).

Winter Park Office


271 N Pennsylvania Ave
Suite 3
Winter Park, FL 32789

Sarasota Office


1819 Main Street
Suite 404
Sarasota, FL 34236

Jacksonville Office


5011 Gate Pkwy, Building 100
Suite 100
Jacksonville, FL 32256