Some retirees have more money than they ever imagined… and still feel guilty buying the $5 M&Ms.

This episode is for the lifelong savers who nailed the retirement planning side—maxed out accounts, invested consistently, hit their “number”—but feel stuck when it’s time to actually spend. James and Ari share real client stories of multimillionaires who still walk past convenience to save a few dollars, not because they need to… but because the “always save” habit is so deeply wired in.

In this episode, you’ll hear:

• Why it’s so hard to shift from accumulator to spender
• How a scarcity mindset can follow you into a very comfortable retirement
• The “M&M moment” that exposed just how powerful old money habits can be
• Simple ways to practice guilt-free, intentional spending that aligns with your values

If you’ve ever asked yourself, “Is it really okay to spend this in retirement?” this conversation will help you see your money as a tool for memories, not just a balance sheet number.

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Retiring by 55 sounds incredible, but it takes more than hitting a savings target. You need to understand how to bridge the gap between your last paycheck and the life you want to live.

In this episode, Ari Taublieb, CFP®, shares the five things every early retiree should know before calling it quits. From the overlooked “Rule of 55” to navigating healthcare costs and tax traps, this guide helps you move forward with confidence in your plan instead of crossing your fingers.

Here’s what we cover:
The Rule of 55 — how it lets you access 401(k) funds early (and the key mistake that disqualifies you).
Healthcare before Medicare — how to budget smartly, use tax strategies, and avoid sticker shock.
Taxes & Withdrawal Strategy — why a $2M 401(k) isn’t really $2M, and how to create real after-tax income.
Legacy Goals — whether you want to leave a million or spend it all, your intentions should drive your plan.
Lifestyle & Purpose — how to avoid the “I’m bored already” phase and build fulfillment into your retirement.

Retiring early isn’t about escaping work, it’s about creating a life you don’t want to escape from.

If you’re serious about retiring at 55 (or sooner), this episode helps you think beyond the math so you can design your freedom with purpose.

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Retirement doesn’t come down to a magic number, it comes down to your number. This episode gives you a simple, personalized framework to decide when you can truly retire based on the life you want, not generic benchmarks.

First, get clear on monthly spending (baseline needs + lifestyle wants). Then reverse-engineer your target by layering in taxes, a sensible withdrawal strategy, guaranteed income (Social Security, pensions), and the one-time costs people forget—like cars, remodels, weddings, or big trips.

Beyond the math, we tackle the emotional side: purpose, identity, and designing days that feel meaningful, so the plan funds a life you actually want to live.

What you’ll learn

• A simple framework to find your number, not “the” number
• How to translate monthly spending into a retirement target
• Coordinating Social Security, pensions, and portfolio withdrawals
• Planning for taxes, RMDs, and estate basics without overwhelm
• Budgeting for big one-time expenses (and avoiding nasty surprises)
• Stress-testing returns and inflation—without getting lost in complexity
• Building purpose and rhythm in the first 1–2 years of retirement

If this brought clarity to your timeline, follow the show, share it with a friend, and leave a quick review—so more people can retire on purpose.

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

What if the “smart” money choice isn’t the choice that builds your best life?
This Root Talks episode starts with a bucket-list moment for James—throwing the first pitch at a Padres game—and turns into a bigger lesson: money is a tool to create meaning, not a score to keep. It’s a look at the Five Types of Wealth (financial, time, social, mental, and physical) and why the spreadsheet answer isn’t always the human answer.

Ari and James share real examples: paying for time to be with family and friends, choosing health over “perfect” returns, even saying yes to a once-in-a-lifetime trip when it matters most. It’s practical retirement planning and financial planning through a different lens—purpose-driven wealth, money mindset, peace of mind.

If the goal is a life well lived, optimization means aligning dollars with values: relationships, adventure, and the stories you’ll keep telling. That’s true retirement lifestyle design... building a life you don’t want to retire from.

Watch to rethink “financially optimal,” and learn how to use your money to buy back time, reduce stress, and live on purpose.

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Most headlines shout that you need millions to retire comfortably. The truth? It depends on you. 

Ari breaks down what “enough” really means, and how to design a plan that fits your lifestyle, health, and peace of mind, not someone else’s spreadsheet.

In this episode, you’ll hear real-life stories that prove one size doesn’t fit all. 

• A saver with $3 million who can’t enjoy travel because of sciatica. 
• A Chevron retiree with $487K, a paid-off home, and a $2,800 monthly budget living his version of freedom. 

Same markets, totally different outcomes—and both work.

Listen as Ari shares a simple framework to turn your lifestyle into a retirement number: calculate your after-tax monthly spend, annualize it, and match it to a conservative withdrawal rate. You’ll see why $35K a month might require $8M, but $3K can work beautifully with smart investing and tax strategy.

You’ll also learn how to avoid the silent killers of a good plan: sequence risk, poorly timed withdrawals, and outdated estate documents. Plus, how to time Roth conversions, structure income for flexibility, and protect your health and wealth over decades.

If you’ve ever asked, “Should I retire now with less or wait for more?” this episode gives you the clarity to choose confidence over comparison.

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Feeling like “flat” retirement spending plans don’t match real life? You’re not imagining it. Spending typically follows a retirement smile: higher in the early “go-go” years, lower in the “slow-go” years, then rising again later with healthcare needs. In this episode, Ari Taublieb, CFP®, shows how acknowledging that curve can unlock more life early on—without losing long-term security.

Using illustrative scenarios (not recommendations), see how a $2,000,000 portfolio might support higher spending in active years (e.g., ~$110k), step down mid-retirement (e.g., ~$85k), and adjust later (e.g., ~$95k–$105k). A $1,000,000 portfolio might follow a similar pattern (e.g., ~$50k → ~$35k → ~$45k–$50k). The point isn’t precision, it’s aligning your plan with how people actually live.

You’ll learn how to frame spending guardrails, set review checkpoints, and coordinate income sources so your plan adapts as health, markets, and goals change. Ready to stress-test your numbers against reality and retire with more confidence?

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

What if the next 10 years bring just 3% returns from the S&P 500?
In this episode, we turn that forecast into a real-world retirement plan—not panic. You’ll learn how to stress test your portfolio, build flexibility into your spending, and design a withdrawal strategy that can survive tough markets.

Listen as Ari and James break down:
Sequence-of-returns risk — why bad early years hurt more than bad averages.
The modern 4% rule — how to use it as a guardrail, not a guarantee.
Diversification that actually works — adding small caps, value, international, and bonds to reduce risk from overexposed tech-heavy portfolios.
Tax-smart moves — Roth conversions, cash buffers, and dynamic withdrawal rules that adapt to changing markets.

Whether you’re planning to retire early or just want peace of mind through an uncertain decade, this guide gives you a clear, flexible framework—so your lifestyle isn’t dictated by Wall Street’s forecasts.

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Feeling like healthcare makes early retirement impossible? It’s a common belief, but often fixable with thoughtful income planning. Premium tax credits under the ACA aren’t vanishing; the enhanced credits are scheduled to sunset after 2025, and the pre-2021 rules (including the ~400% FPL income cap) are slated to return in 2026 unless Congress acts. The takeaway: managing MAGI matters.

In this episode, Ari Taublieb, CFP®, walks through a practical, illustrative case: a 60-year-old couple with ~$1.55M spread across taxable, pre-tax, and Roth accounts. You’ll see how the source of withdrawals (e.g., harvesting from taxable accounts vs. large pre-tax distributions) can change MAGI—and therefore subsidy eligibility—potentially lowering Marketplace premiums materially. You’ll also learn key HSA rules after age 65 (non-medical withdrawals are taxed as income but no 20% penalty) and what’s changing for HSAs in 2026: Bronze and Catastrophic ACA plans are slated to be HSA-eligible, expanding access to tax-advantaged saving.

You’ll leave with a playbook: align cash-flow needs with tax brackets, plan around the 400% FPL threshold, coordinate Roth/pre-tax/taxable withdrawals, and revisit the plan annually as laws and income shift. 

Ready to pressure-test your numbers and retire with more confidence? Subscribe to the Early Retirement Podcast.

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Feeling anxious about taking money from your retirement accounts? You’re not alone. That first withdrawal feels odd after decades of saving, but a clear process and tax plan turns uncertainty into confidence.

In this episode, Ari Taublieb, CFP®, breaks down how withdrawals actually move from investment accounts to your checking—and what the tax bite may look like.

Using a simple $100,000-per-year example for a married couple filing jointly, you’ll see illustrative ballpark math: in a no-income-tax state (e.g., Florida) the effective rate can land around ~8% (~$8,044), while a high-tax state (e.g., California) might be ~9.7% (~$9,683). That ~$2,000 gap often isn’t big enough to justify uprooting your life.

You’ll also learn a smarter way to “hold cash” for spending: keep withdrawal dollars intelligently invested while you spend. A $100,000 portfolio earning a modest 5% generates ~$5,000, which is roughly equivalent to one month of expenses at that rate, before fees, taxes, and market volatility. It’s not a guarantee, just math.

We’ll cover practical setups, like creating a dedicated travel fund while keeping core assets growing, and choosing a payout cadence (monthly, quarterly, or biweekly) that fits your comfort level. Whether you retire at 50, 60, or 70, the principles stay the same.

Ready to retire with more confidence? 

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.

Are you overthinking your Roth conversion strategy? While Roth conversions can be powerful, not every retiree needs them. In this video, you’ll learn when a Roth conversion truly makes sense—and when it may just add unnecessary complexity.

Using the “cauliflower analogy,” we break down how Required Minimum Distributions (RMDs) can push retirees into higher tax brackets, and why paying taxes now can sometimes help avoid bigger bills later. But there’s an even more important question: could you be better off retiring earlier or spending more instead of over-optimizing your tax plan?

We’ll also highlight the sweet spot for conversions (between retirement and when Social Security and RMDs begin) when tax savings can be most effective. Ultimately, a great financial plan isn’t defined by your Roth conversion strategy, but by building a life well lived. 

 Whether you're considering your first conversion or refining your existing approach, this episode provides the foundation for making decisions aligned with what truly matters in your financial journey. 

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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.

Create Your Custom Early Retirement Strategy Here

Get access to the same software I use for my clients and join the Early Retirement Academy here

Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.