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Retirement isn’t just about having enough money—it’s about making the most of it. That’s why we’re launching a new retirement community designed to go beyond financial planning. Sure, we’ll cover investing, tax strategies, and estate planning, but we’re also creating a space to talk about the things that make retirement fulfilling—connection, travel, health, and purpose.

Inside, you’ll be able to engage with like-minded peers, get expert insights, and explore ideas to shape the next chapter of your life. We’ll have guest speakers, live events, and interactive discussions to help you feel confident in your planning and inspired about what’s ahead.

Root clients get free access, and for everyone else, it’s $50 per month—early adopters can join for just $20. If you’re looking for more than just financial advice, we’d love for you to be part of it.

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - A new retirement community
2:56 - Sharing experiences, creating initiatives
4:22 - Goal: best possible retirement
5:36 - Who is this for?
7:07 - Why join?
10:17 - Pricing
12:13 - The power of community

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

To maximize your Social Security benefits in retirement, it’s essential to understand five key limits and thresholds:

✅ Earnings Limit: If you start Social Security before full retirement age, benefits may be reduced if your wages exceed the annual or monthly earnings limit. Only income earned after starting benefits counts.

✅ Social Security Wage Base: This is the maximum amount of earnings subject to Social Security taxes each year. It impacts both how much you pay into the system and the benefits you may receive.

✅ Maximum Benefit: Your benefit amount is based on factors like your lifetime earnings and the age at which you begin collecting benefits. Delaying benefits increases your monthly payments, while starting early reduces them.

✅ Provisional Income: This determines how much of your Social Security benefit is taxable. Higher income levels can result in up to 85% of your benefit being taxed at the federal level.

✅ Bend Points: These thresholds influence how your lifetime earnings are converted into benefits. Lower earnings are replaced at a higher percentage, meaning early contributions can have a significant impact.

Understanding these limits helps you make strategic decisions and optimize your retirement income.

Questions answered:
1. How can I maximize my Social Security benefits and avoid unnecessary reductions?

2. What factors determine how much Social Security I will receive in retirement?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - David's question
1:47 - SS earnings limit
4:51 - Monthly numbers matter
6:04 - SS wage base
9:11 - Max SS earning amount
11:26 - Provisional income
13:32 - SS bend points

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

Root Financial is redefining what it means to serve clients by putting team culture front and center. In this episode, James and Ari dive into the firm’s bold move to hire a Head of Culture—an uncommon role in financial advising—dedicated to supporting the growth and well-being of their advisors. Why? Because when advisors thrive, clients get the personalized attention they deserve.

At Root, we’re intentional about avoiding the usual industry traps, like overloading advisors with massive client lists or sales quotas that can compromise service. Instead, we focus on sustainable growth, aligning our goals with yours and using tools like OKRs (Objectives and Key Results) to stay on track.

With a Net Promoter Score of 91—well above the industry average—we’re proving that building a strong internal culture leads to happier clients and better outcomes.

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - Company culture affects clients
4:08 - Ari's quick story
5:59 - Hiring a Head of Culture
10:54 - Advisors have how many clients?
14:24 - NPS and retention rate
17:28 - OKRs
20:57 - What makes Root different

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

The Social Security Fairness Act, signed into law on January 5 by former President Joe Biden, repeals the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO), which previously reduced Social Security benefits for individuals with non-covered pensions, such as teachers, firefighters, and postal workers. This change significantly increases benefits for affected individuals, in some cases by over $1,000 per month, and applies retroactively to the end of 2023.

While the law addresses long-standing concerns about fairness, it also accelerates the depletion of Social Security funds, already projected to face insolvency by the 2030s. This $190 billion expense over the next decade may force future changes, such as tax increases, higher retirement ages, or adjustments to the system. For those impacted by WEP or GPO, the law offers immediate financial relief but highlights the need for broader, sustainable reform to preserve Social Security for all beneficiaries.

Questions answered:
How does the Social Security Fairness Act impact individuals with non-covered pensions like teachers, firefighters, and postal workers?

What are the potential long-term consequences of the Social Security Fairness Act on the Social Security fund's sustainability?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - SS Fairness Act -- ex. Maria
2:46 - Bend points
4:49 - Back to Maria's situation
5:54 - Pros and cons
7:38 - Bill magnifies SS problems

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

In this behind-the-scenes episode, James and Ari explore what sets Root apart in the financial advising industry. Moving beyond traditional roles like stock pickers and planners, they emphasize Root’s mission as “protectors” of clients’ most cherished goals, helping them achieve a life of purpose and fulfillment. They discuss how Root’s culture prioritizes personalized care and intentional growth, from hiring advisors who embody Root's ethos to reinvesting in services like tax planning and estate planning to enhance client experiences.

James and Ari also address how Root balances expansion with maintaining high service quality, ensuring each client feels uniquely supported. They share insights into Root’s “master plan,” which includes innovative frameworks for advisor development and creating scalable yet deeply personalized services. Root’s philosophy of holistic, forward-looking financial planning integrates life coaching elements, focusing on helping clients live richer, more meaningful lives. This episode offers a fresh perspective on financial advising, showcasing Root’s commitment to redefining the industry.

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - Root in one word -- protector
3:54 - Life advisors
7:31 - Beating the waiter
9:31 - Integrating tax planning
12:45 - Services to add in the future
16:47 - Gauging fit; growth philosophy
20:23 - Client satisfaction and advisor development
24:07 - Wrap-up

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

Direct indexing, an advanced investment strategy, allows investors to own individual stocks within an index instead of a mutual fund or ETF, offering greater control and flexibility. This approach is particularly valuable for tax-loss harvesting, where selling underperforming stocks and reinvesting can offset gains and reduce taxes without losing market exposure.

Ideal for high tax brackets, concentrated stock positions, or charitable giving, direct indexing can boost returns by 0.5%-1.85% annually over decades, a benefit known as “tax alpha.” Once reserved for ultra-wealthy investors, advances in technology now make it accessible to portfolios starting at $500K. However, success requires sophisticated tools and tax expertise, making it a powerful strategy for the right investors.

Questions answered:
1. How can direct indexing and tax-loss harvesting improve investment returns without increasing risk?

2. Who benefits most from using a direct indexing strategy?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - The strategy - direct indexing
3:57 - Tax loss harvesting
7:22 - More than locking in losses
9:36 - The research
11:38 - An involved process
13:05 - Criteria 1, 2, and 3
17:04 - Criteria 4 and 5
19:52 - More accessible due to technology

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

James and Ari provide a behind-the-scenes look at Root Financial, shifting from typical financial strategies to how their team operates. They discuss Root’s intentional approach to maintaining consistency in financial advising through rigorous hiring practices and its structured training program, "Root University." James emphasizes the importance of aligning advisors with the firm's ethos to ensure clients receive a consistent and personalized experience. The hiring process focuses on cultural fit, technical skills, and a shared philosophy of integrating financial planning with life goals.

Ari highlights the collaborative and values-driven workplace culture, sharing anecdotes about the thorough training process and the effort to foster long-term relationships with both clients and staff. They also hint at future episodes that will cover Root’s unique approach and plans for growth, aiming to deliver impactful services while creating a workplace where advisors thrive.

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - A peek behind the scenes
2:04 - The Root process
5:08 - The hiring process
9:08 - Associates vs lead advisors
12:31 - Book vs real-world smarts
15:11 - Who's Louis?
16:56 - Root advisors love their jobs
20:22 - Advisors choose their clients
21:37 - Future episodes

Create Your Custom Strategy ⬇️

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Join the new Root Collective HERE!

Many individuals are hesitant to retire, even when financially prepared, due to uncertainty and a lack of clear planning. This episode provides a practical guide to making retirement a reality, focusing on three key steps:

1. Assess Your Current Financial Health
2. Envision Your Ideal Retirement
3. Connect Financial Readiness to Goals

By addressing these steps, you can retire confidently, balancing future preparation with enjoying today.

Questions answered?
1. How can I determine if I am financially ready to retire?

2. What steps should I take to plan for a fulfilling and sustainable retirement?

Submit your request to join James:
On the Ready For Retirement podcast: Apply Here
On a Retirement Makeover episode: Apply Here

Timestamps:
0:00 - Assess current financial position
2:21 - Know monthly income and expenses
4:30 - Review debts
6:46 - Envision ideal retirement
9:29 - Connect the dots
13:26 - Retire with confidence

Create Your Custom Strategy ⬇️

Get Started Here.

Join the new Root Collective HERE!