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Circle of Advisors

Seeking counsel through a Circle of Advisors presents a strategic approach to financial decision-making, addressing both the analytical and emotional facets involved. This method integrates data-driven insights with personal values, leveraging a team of specialists to offer well-rounded advice. Such a circle encompasses diverse expertise, aiding in making informed choices that consider both numerical data and emotional well-being.

Engaging with a Circle of Advisors aligns with PlanAssist's principles of having a plan, diversification, and consulting professionals for significant financial decisions. It offers a safeguard during crises by providing unbiased input, thereby supporting both members of a couple in financial decision-making roles.




financial roadmap planassist

This advisory approach does not impose decisions but rather offers guidance for independent evaluation. It underscores the complexity of financial matters, acknowledging that no individual can master all areas, from tax and legal issues to investments and insurance. A Circle of Advisors thus acts as a support network, ensuring decisions are both informed and emotionally considerate, with PlanAssist offering foundational support for navigating your financial future.


Timothy Clifford Financial Advisor In Florida

From the day I started my career in the financial industry as a Runner, handling orders from the phone to the trading pits on the floor of the Chicago Mercantile Exchange in the 80s, I knew this was the industry where I wanted to build my career. Little did I anticipate the unexpected twists and turns defining my journey from a Runner to a Financial Advisor in Winter Garden, Florida.


My journey through the financial services industry has been remarkably diverse, spanning from Commodity Trading in the 80s to my role as a Stockbroker in the Discount Stock Business during the 90s. In the 2000s, I made a transition into the Tax and Advisory business, ultimately culminating in the establishment of my own Registered Investment Advisor (RIA) practice in the 2010s. While this trajectory might seem straightforward, it offers a glimpse into the rich and varied experiences that have shaped my career.

Throughout this journey, my unwavering passion has consistently revolved around working closely with clients. Regardless of their profession, managing income, expenses, investments, and more is a pivotal aspect of everyone's financial journey. It's this integral connection between financial decisions and all aspects of our lives that brings me satisfaction in guiding people on their financial odysseys.


While financial decisions are inherently unique to each individual, I've observed that many successful individuals adhere to a set of common principles. These principles include maintaining a long-term perspective, diversifying their investments, seeking professional advice, and crafting a well-structured plan.


This alignment with these principles empowers me to deliver value and support individuals on their journey from "Here" to "There." It's the reason why PlanAssist®, our financial planning subscription model, along with a team of professionals, has seamlessly integrated into our comprehensive offering.


At the heart of my career is a commitment to your financial well-being, and I look forward to continuing to assist you in achieving your financial goals.


1. Managing Partner & Financial Consultant

Core Wealth Consultants LLC · Full-time

Aug 2012 - Present · 10 yrs 11 month

Orlando, Florida, United States · Hybrid

Helping clients with retirement planning and investing.

Timothy Clifford position at block finance

3. Vice President

H&R Block Financial Advisors

Feb 1999 - Dec 2008 · 9 yrs 11 month

Indianapolis, Indiana Area

02/1999 to 04/2006 Field Leadership and Sales Management
05/2006 to 12/2008 VP Enterprise Scale & Tax Partnering02.

core wealth logo
Timothy Clifford as vice president at ameriprise financial services

2. Vice President

Ameriprise Financial Services, Inc.

Jan 2009 - Jul 2012 · 3 yrs 7 month

Indianapolis, Indiana Area

01/2009 to 01/2011 - RVP Field Leadership and Sales Management
02/2011 to 07/2012 - VP Service Delivery and Integration

Timothy Clifford as branch manager at charles schwab

4. Branch Manager

Charles Schwab

Apr 1990 - Jan 1999 · 8 yrs 10 mos

Indianapolis, Indiana Area

Sales management and worked directly with clients

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