Tag: Retirement Planning
How AI is Transforming TIAA Retirement Planning (Ep. 11)

How AI is Transforming TIAA Retirement Planning (Ep. 11)

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Technology is changing how we approach retirement planning, but are financial professionals embracing these changes or resisting them?

What if there were a tool that could map out your entire retirement strategy from age 30 to 65, including Roth conversions, tax optimization, and withdrawal strategies?

In this episode, Greg Shepard discusses his hands-on experience implementing artificial intelligence tools to help TIAA participants plan their retirement more effectively. He explains how AI can create personalized roadmaps for retirement contributions, tax diversification strategies, and withdrawal planning. Greg also addresses the concerns and opportunities AI presents for financial advisors, and why younger professionals should pay attention to this technology now.

Greg discusses:

  • The comparison between AI’s current stage and early internet technology like AOL dial-up
  • How AI tools can create comprehensive retirement roadmaps that offer a different level of detail than some traditional planning tools
  • The resistance and fear within the financial advisory industry regarding AI implementation
  • Teaching AI platforms to understand complex TIAA retirement plans and contract structures
  • Why generalist advisors should be concerned while specialized advisors can leverage AI to enhance their services
  • And more!

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You Don’t Know What You Don’t Know About TIAA Retirement Planning (Ep. 10)

You Don’t Know What You Don’t Know About TIAA Retirement Planning (Ep. 10)

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Most people believe they have their retirement plan under control until they get closer to the finish line and realize they are guessing. When it comes to TIAA accounts, guessing can create costly mistakes, stress, and irreversible decisions.

In this episode, Greg Shepard breaks down why DIY retirement planning often falls apart, especially for higher education professionals navigating TIAA’s complex rules. Through real client stories and candid conversations, Greg explains why confidence without clarity can lead to missed opportunities, tax inefficiencies, and unnecessary strain at home.

Key insights covered:

  • Why most pre-retirees underestimate TIAA complexity
  • The risks of relying on call centers, YouTube, or AI for retirement decisions
  • How irreversible paperwork mistakes can derail a retirement plan
    The emotional toll DIY planning can place on couples
  • Why humility and professional guidance can reduce stress and improve outcomes
  • And more!

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Roth IRA or Roth 403(b): Which Should I Do? (Ep. 9)

Roth IRA or Roth 403(b): Which Should I Do? (Ep. 9)

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Many higher education professionals are missing out on a powerful retirement tool hiding in plain sight within their employer plans.

Are you leaving tax-free money on the table? Do you know the difference between contribution limits and income restrictions across retirement accounts?

In this episode, Greg Shepard breaks down the critical differences between Roth 403(b) and Roth IRA accounts, revealing why so many employees remain unaware of valuable retirement options. Greg explains income limits, withdrawal rules, tax diversification strategies, and when high earners should reconsider their approach.

Key insights covered:

  • The widespread lack of awareness about Roth 403(b) options among higher education and medical professionals
  • No income limits on Roth 403(b) contributions versus strict Roth IRA income restrictions
  • Tax-free withdrawal benefits and the five-year holding requirement for Roth accounts
  • Custom tool development for calculating optimal pre-tax versus post-tax contribution strategies
  • Tax diversification strategies for retirement planning and why employers should mandate education sessions
  • And more!

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TIAA Traditional: Which Contracts do I Annuitize First? (Ep. 8)

TIAA Traditional: Which Contracts do I Annuitize First? (Ep. 8)

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If you’ve ever wondered whether you’re making the most of your TIAA Traditional account, this episode is a must-listen. Greg Shepard breaks down the five essential questions every TIAA participant should ask, whether you’re ten years from retirement or just starting your career.

In this episode, Greg explains how to think strategically about your TIAA Traditional contracts, plan ahead for lifetime income options, and avoid common mistakes that can limit flexibility later. He shares real-world insights on how early preparation can help you retire with confidence and clarity.

Greg discusses:

  • What key actions to take ten years before retirement
  • How to rebalance your portfolio as you approach retirement
  • The most common mistakes people make when planning
  • How to model future income and healthcare costs
  • What to know before choosing an annuitization strategy
  • And more!

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TIAA Traditional Lifetime Income Pros vs Cons (Ep. 7)

TIAA Traditional Lifetime Income Pros vs Cons (Ep. 7)

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Retirement income decisions can be overwhelming, especially when converting TIAA Traditional balances into lifetime income.

In this episode, Greg Shepard breaks down one of his most frequently asked questions: “Should I choose lifetime income, and how much?” Greg shares real client stories and explains the pros, cons, and emotional factors behind this important decision. He also explains how TIAA lifetime income works, when it makes sense, and how to avoid costly mistakes when selecting it.

Greg shares:

  • The key differences between lifetime income and maintaining liquidity
  • The ideal scenarios where lifetime income might make sense
  • The 40% guideline for transitioning to lifetime income
  • Emotional and behavioral factors that influence retirement decisions
  • The importance of asking the right questions before locking in your plan
  • And more!

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Why 10 Years Out Matters for Your TIAA Plan (Ep. 3)

Why 10 Years Out Matters for Your TIAA Plan (Ep. 3)

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Ten. It is a simple number, but when it comes to your TIAA retirement plan, it can make all the difference.

In this episode of TIAA Simplified, Greg Shepard shares why preparing at least ten years before retirement is critical for higher-ed professionals with TIAA accounts. Through real client stories and clear explanations, Greg breaks down the importance of understanding liquidity, portfolio allocation, and the unique rules around TIAA Traditional.

Greg discusses:

  • Why waiting until the last minute can limit your retirement choices
  • The role of TIAA Traditional in your income strategy
  • How to rebalance your portfolio as you approach retirement
  • Common mistakes people make with too much or too little in Traditional
  • And more!

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Understanding TIAA’s Hidden Nuances (Ep. 2)

Understanding TIAA’s Hidden Nuances (Ep. 2)

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Many higher education and medical professionals depend on TIAA for their retirement savings, yet most don’t fully understand the fine print.

From liquidity restrictions to overlooked contract details, the consequences of not asking the right questions can be costly.

This week, Greg Shepard breaks down the most common misunderstandings about TIAA Traditional and explains why a personalized approach is critical.

His mission is clear: simplify the complexities so you can make informed decisions well before retirement.

Greg discusses:

  • Why TIAA’s complexities often only become clear close to retirement
  • The importance of knowing whether your TIAA Traditional funds are liquid or illiquid
  • How over-concentration in TIAA Traditional can derail retirement plans
  • Why contract details are often missed and how to find them
  • The need for customized strategies rather than a one-size-fits-all approach
  • And more!

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Meet the Man Behind the Mic: Introduction to TIAA Simplified’s Greg Shepard (Ep. 1)

Meet the Man Behind the Mic: Introduction to TIAA Simplified’s Greg Shepard (Ep. 1)

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Most people believe their retirement plan is on autopilot. But what if the fine print in your TIAA Traditional account could derail everything at the finish line?

In the premiere episode of TIAA Simplified, Greg Shepard shares how helping higher ed professionals navigate their TIAA investments has completely reshaped his approach to advising. 

These aren’t just account balances and allocations. They’re emotional, high-stakes decisions often made without the right information. Greg dives into the real stories of confusion, frustration, and life-altering revelations that sparked his mission to bring clarity to this overlooked topic.

Greg discusses:

  • How years of traditional financial advising felt empty until he began helping TIAA participants with their most pressing questions
  • The overlooked restrictions inside TIAA Traditional and how they catch people off guard near retirement
  • Why even highly intelligent professionals struggle to understand the mechanics of their plan
  • What pushed Greg to start making videos and podcasts that became lifelines for people in need of answers
  • The urgency of asking the right questions well before retirement to avoid irreversible planning mistakes
  • And more!

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