Why We Wait Until the Third Meeting to Talk About Investments (and Why It Works)
Nov 19, 2025
Discover why the timing of investment discussions is crucial in building client trust. Learn how great advisors prioritize lifestyle and cash flow before jumping into portfolios. James shares a compelling Roth-conversion story that illustrates the conflict between tax savings and living well. Unpack the Sequoia process, which frames meetings around clients' values and visions for retirement. Understand how to create a client experience that emphasizes meaningful conversations over mere numbers.
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question_answer ANECDOTE
Tax Savings That Cost A Life
James tells a story about showing a client a Roth conversion that would save over $1M in taxes but require sacrificing their lifestyle.
The client rejected the plan because it would reduce the life she wanted to live, illustrating priorities matter more than tax math.
volunteer_activism ADVICE
Start With Life, Not Products
Do start planning by asking what life the client actually wants to live before recommending products.
Build the kickoff meeting around values, fears, goals, and the client's desired lifestyle to set strategy first.
volunteer_activism ADVICE
Resolve Cashflow Before Portfolios
Do run an income/cashflow meeting before investment discussions to model expenses and income sources.
Use that plan to answer whether clients can retire, must save more, or should adjust spending to meet their desired lifestyle.
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This episode of Root Ready digs into one of the most overlooked parts of the client process: the proper timing for investments to enter the conversation. It’s a masterclass in pacing, patience, and purpose. You will walk away from this video knowing how smart advisors earn trust and set the foundation before talking portfolios.
James unpacks why great planning starts with clarity around lifestyle, cash flow, and strategy — not product recommendations or asset allocation. You’ll learn how to reframe client expectations, keep the process focused on what truly matters, and lead conversations that put life before numbers.
Because great advisors know the goal isn’t to manage money. It’s to help clients live better with it.
Listen to this episode to learn how to structure your meetings with intention, elevate your value beyond investments, and create a client experience that builds confidence from the very first conversation.
Submit a question for James here: https://rootreadypodcast.com/
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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.
The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.
Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements
Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.
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