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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.




planassist financial roadmap planner in winter garden florida usa

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

My career began not in an office but on the floor of the Chicago Mercantile Exchange in the 1980s, where I started as a runner before becoming a trader, immersing myself in the world of commodities. This foundational experience laid the groundwork for my understanding of financial markets.

The 1990s brought a pivotal shift when I joined Charles Schwab & Co., an opportunity that allowed me to interact with a broad spectrum of financially successful clients across various industries. It was during this period that I began to notice and pay attention to how financially successful people made financial decisions, and I realized there was a difference between those who earn a lot of money and those who have accumulated significant wealth.

These insights were crucial in shaping my approach to financial management, steering me away from the excitement of trading to a more structured focus on wealth building. As I advanced into leadership roles in the 2000s, my resolve to help others build and maintain their wealth only strengthened. By 2012, I had earned my Certified Financial Planner® designation and was ready to leverage my extensive experience and insights by founding Core Wealth Consultants LLC, marking the beginning of my journey as a financial advisor in Central Florida.

The development of PlanAssist® marked a significant milestone in my career, driven by a desire to simplify wealth-building principles for those who, for the most part, understand finances and know what they need to do but may need a nudge or assistance with the next steps—essentially, help with prioritization and organization.

Inspired by the philosophies of renowned investor Charlie Munger—particularly the principle that "we can only help those who almost know"—and tailored to my unique insights, adding my own which is “financial success is not event but the accumulation of all our decision over decades”, PlanAssist® embodies the culmination of my experiences and the principles that, in my opinion based on experience, individuals need to implement to some degree to grow and maintain wealth.


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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