Work Overview
LATEST PROJECTS
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No Charge 30 Min Consultation |407-393-5985| info@planassist.com
Your Circle of Advisors
Significant financial decisions are rarely simple. They require balancing hard data with your personal values and emotional well-being. Because the complexities of true wealth span tax, legal, investment, and insurance matters, no single individual can master them all. That is why I advocate for building your own "Circle of Advisors"—a network of independent specialists whose combined expertise ensures your financial plan is structurally sound.
A Team of Independent Experts
True wealth management requires specialized knowledge. While I focus on your financial and investment roadmap, I strongly encourage clients to engage external, independent professionals—such as CPAs and estate attorneys—to ensure every specific legal and tax angle is covered by an expert in that field.
The Financial Quarterback
You shouldn't have to translate between your different advisors. While you hire and work directly with your legal and tax experts, PlanAssist® can help coordinate those conversations. We act as a sounding board, ensuring that all your independent professionals are working from the same playbook.
Collaborative Insight
Financial planning shouldn't happen in a silo. When your financial advisor, tax professional, and legal counsel bring their specific insights to the table, it ensures all angles of your situation are considered. This teamwork helps you navigate complex markets and life events with greater clarity.
FOUNDER
From the Trading Floor to Your Financial Future
My career didn’t begin in a quiet office—it started in the 1980s on the high-energy floor of the Chicago Mercantile Exchange. Moving from a runner to a commodities trader immersed me in the realities of the financial markets and gave me a foundational understanding of how they truly operate.
The pivotal shift in my career happened in the 1990s when I joined Charles Schwab & Co. Working closely with highly successful individuals across various industries, I noticed a crucial pattern: there is a profound difference between earning a high income and accumulating significant wealth.
That realization changed my approach. I stepped away from the short-term excitement of trading and dedicated myself to the structured focus of long-term wealth building. By 2012, I had earned my Certified Financial Planner® designation and founded Core Wealth Consultants LLC in Central Florida to help clients manage this exact process.
The Origin of PlanAssist
Through my years of advising, I realized that many people actually have a solid grasp of their finances. They know what they need to do, but they often need a nudge, a structured framework, and help organizing their next steps.
Inspired by Charlie Munger’s philosophy that "we can only help those who almost know," I developed PlanAssist®. It is the culmination of my decades of experience, designed to give you the clear, prioritized roadmap you need to build and maintain your wealth.
"Financial success is not an event, but the accumulation of all our decisions over decades."
Timothy Clifford
MY EXPERIENCE
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.
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.
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
4. Branch Manager
Charles Schwab
Apr 1990 - Jan 1999 · 8 yrs 10 mos
Indianapolis, Indiana Area
Sales management and worked directly with clients

