Planning by Topic
Planning by Topic
Explore retirement, tax, estate, Medicare, Social Security, business succession, gifting, and investing resources — commentary, videos, and reports organized by topic.
Healthcare in Early Retirement: Bridging to Medicare
September 18, 2026
Retiring before age 65 means replacing employer health coverage while managing income, taxes, and Medicare timing. This post explains how COBRA, Marketplace plans, premium tax credits, and Medicare enrollment can inte
Social Security at 62, 67, or 70? A HNW Decision Framework
September 17, 2026
For high-net-worth households, Social Security claiming is less about need and more about tradeoffs. This framework compares ages 62, 67, and 70 across benefit levels, survivor protection, taxes, earnings limits, and
How Social Security Is Taxed (and How to Minimize It)
September 16, 2026
Social Security benefits can become partially taxable when combined income crosses federal thresholds. Coordinating IRA withdrawals, Roth conversions, deductions, Medicare timing, and Oklahoma tax rules may help manag
Pension Lump Sum vs. Monthly Annuity: How to Decide
September 14, 2026
Compare a pension lump sum and monthly annuity by weighing income security, survivor protection, taxes, PBGC limits, and rollover rules rather than relying on simple payout percentages alone. This overview covers pens
What HNW Retirees Get Wrong About Required Minimum Distributions
September 12, 2026
High-net-worth retirees often misread required minimum distributions as a spending rule instead of an income-planning decision. This post explains first-year timing at age 73, the risk of doubling distributions in one
Reverse Mortgages: A Tool, Not a Last Resort
September 11, 2026
Reverse Mortgages: A reverse mortgage can transform home equity into usable cash without requiring monthly payments, but it is not free money. The decision depends on how it impacts your total household plan, financin
How to Pay for Long-Term Care Without Buying LTC Insurance
September 10, 2026
Planning to pay for long-term care without insurance requires a deliberate strategy. This guide covers quantifying care reserves, protecting the surviving spouse, and identifying specific assets like HSAs and home equ
Hybrid LTC Insurance: Pros, Cons, and Who Should Consider It
September 9, 2026
Hybrid LTC insurance: Hybrid long-term care insurance combines care benefits with life insurance or an annuity, ensuring that if care is never needed, the policy may still provide a death benefit or surrender value. T
Medicare 101: A Complete Guide for Oklahomans Turning 65
September 8, 2026
Medicare 101: Turning 65 involves critical decisions regarding doctors, prescriptions, and health savings accounts. This 2026 guide covers federal enrollment windows and Oklahoma-specific resources available for new r
Medicare IRMAA: How to Avoid the 'Tax' on High-Income Retirees
September 7, 2026
Medicare IRMAA is an income-related premium adjustment for Part B and Part D based on a two-year lookback. High-income retirees can manage these surcharges through proactive tax planning.
Variable Withdrawal Strategies: Guyton-Klinger Explained
September 5, 2026
Variable withdrawal strategies offer a middle path between fixed spending and floating market-based withdrawals, using documented guardrails to define when spending should rise, stay flat, or be reduced to preserve po
Yen Intervention and the Treasury Buyer of Last Resort
September 4, 2026
Yen intervention and the Treasury buyer of last resort: A coordinated U.S.-Japan currency intervention reveals how tools like the FIMA repo facility act as a backstop for the Treasury market by preventing forced liqui
When Should Retirees Hold Annuities (and When They Shouldn't)
September 4, 2026
When should retirees hold annuities: Few retirement products create stronger reactions than annuities. For Oklahoma retirees, the decision depends on whether the income floor is met and if the household values risk tr
SPIAs, DIAs, and QLACs: A Retiree's Guide to Income Annuities
September 3, 2026
Retirees often view income annuities as a single category, but SPIAs, DIAs, and QLACs serve distinct timing and tax roles. Understanding these differences helps align guaranteed income with longevity risks and RMD man
Sequence-of-Returns Risk: Real Examples From 2000, 2008, and 2022
September 2, 2026
A retirement portfolio can survive a bad year, but it may not survive a bad year at the wrong time.
Building a Retirement Paycheck: How HNW Retirees Get Paid Monthly
September 1, 2026
Turning a portfolio into a reliable retirement paycheck requires more than just yield.
Why Bond Ladders Belong in a $2M+ Retirement Plan
August 31, 2026
bond ladders in a $2M+ retirement plan: A bond ladder provides a structured cash-flow solution for high-net-worth retirees. By staggering maturities, investors can fund near-term spending needs without the pressure of...
Treasury Bills vs. Money Market Funds for Cash Reserves
August 29, 2026
Treasury Bills vs. Money Market Funds: High-net-worth families must choose cash tools based on timing, taxes, and liquidity. Explore the strategic trade-offs between individual Treasury bills and money market funds.
The 4% Rule Is Dead: What Replaces It in 2026
August 28, 2026
The 4% rule is dead: Why a static withdrawal rule is giving way to monitored guardrails, flexible spending, and better conversations about regret. Discover the shift from 1994 formulas to dynamic income planning.
Bucket Strategy vs. Total Return Approach to Retirement Income
August 27, 2026
Moving from accumulation to distribution is a major transition. Compare the psychological visibility of the bucket strategy against the efficiency of the total return
How Oklahoma Property Tax Compares to Texas and Surrounding States
August 26, 2026
Oklahoma property tax: A comparison of Oklahoma's 0.79% effective property tax rate against Texas, Kansas, and other neighboring states, highlighting how valuation caps and assessment ratios impact total costs.
Kiddie Tax Rules: Funding Your Kids' Investment Accounts
August 25, 2026
Kiddie Tax Rules: Understanding the 2026 unearned income thresholds and account types—UTMAs, 529s, and Roth IRAs—is essential to funding a child's investment account without creating a tax surprise.
Form 1041 Trust Tax Returns: What to Expect
August 24, 2026
Form 1041 Trust Tax Returns: Form 1041 is the federal income tax return for estates and trusts. Understanding how distributions affect tax liability and compressed brackets is essential for trustees.
Step-Up in Basis: The Most Important Estate Tax Concept You've Never Heard Of
August 22, 2026
Learn how the step-up in basis rule can create significant income-tax savings for heirs by resetting the value of inherited property, regardless of estate tax status.
Generation-Skipping Transfer Tax: Planning Around the Exemption
August 15, 2026
2026 GST exemption: The GST tax often remains invisible until a distribution to a grandchild occurs. With the 2026 exemption set at $15 million, proper allocation on Form 709 is essential for success.
Charitable Lead Trusts (CLTs): When the Math Works
August 14, 2026
Charitable Lead Trusts: A charitable lead trust (CLT) is a split-interest trust that supports charity for a fixed term before transferring the remainder to heirs. Success depends on the §7520 rate, net returns, and lo...
Spousal Lifetime Access Trusts (SLATs) Before the 2026 Sunset
August 12, 2026
The 2025 tax law replaced the scheduled sunset with a $15 million basic exclusion amount for 2026. Learn how Spousal Lifetime Access Trusts (SLATs) remain relevant for estate freezing and legacy planning for high-net-...
Grantor Retained Annuity Trusts (GRATs) Explained for Founders
August 11, 2026
Grantor Retained Annuity Trusts (GRATs): A founder’s estate plan often fails to account for the rapid growth of private company equity. A Grantor Retained Annuity Trust (GRAT) solves this by separating current apprais...
Family Limited Partnerships (FLPs) for Wealth Transfer
August 7, 2026
Family Limited Partnerships for Wealth Transfer: Family Limited Partnerships (FLPs) allow families to transfer economic ownership while preserving a disciplined framework for centralized management and control of unde...
Augusta Rule: Renting Your Home to Your Business
August 7, 2026
Augusta Rule: Renting Your Home to Your Business: The Augusta Rule allows a homeowner to exclude rent received from a dwelling used as a residence when the home is rented for fewer than 15 days during the year. Pair t...
S-Corp Reasonable Salary: How to Stay Off the IRS Radar
August 6, 2026
S-Corp Reasonable Salary: Avoiding IRS scrutiny as an S-Corp shareholder requires balancing wages and distributions based on actual work performed. Learn how to document reasonable compensation to protect your business.
Cash Balance Plans: $200k+ Contributions for Business Owners
August 5, 2026
Cash Balance Plans: $200k+ Contributions: For high-income business owners, cash balance plans provide a path to tax-deferred contributions far exceeding standard 401(k) limits through a hybrid pension structure.
Solo 401k vs. SEP IRA for Self-Employed Oklahomans
August 1, 2026
Solo 401k vs. SEP IRA: A Solo 401(k) and a SEP IRA can reach the same headline contribution ceiling, but they do not take the same road to get there. The Solo 401(k) lets an owner contribute as both employee and emplo...
How to Use a Defined Benefit Plan as a Late-Career Tax Shield
July 31, 2026
defined benefit plan as a late-career tax shield: A defined benefit plan can offer high-income business owners a substantial tax deferral by focusing on promised benefits rather than individual contribution limits.
Real Estate Professional Status: A Tax Planning Goldmine
July 30, 2026
Real Estate Professional Status: Section 469 guidelines allow real estate professionals to reclassify passive rental losses into active deductions. Learn the two-gate test involving the 750-hour rule and material part...
Opportunity Zones: A Realistic Look at the 2026 Window
July 29, 2026
Opportunity Zone 2026 window: The year 2026 represents a critical transition for Opportunity Zone investors. As the original program's fixed inclusion date arrives, new permanent rules scheduled for 2027 introduce a r...
1031 Exchanges: Are They Still Worth It in 2026?
July 28, 2026
1031 Exchanges: Are They Still Worth It in 2026?: The tax deferral remains powerful --- but only when the next property is a good investment before the tax benefit is counted. July 28, 2026 Real-...
Section 1202 (QSBS): The HNW Founder's Best Tax Break
July 27, 2026
Section 1202 QSBS: Discretionary planning for Section 1202 Qualified Small Business Stock (QSBS) can allow founders to exclude millions in federal capital gains. Understanding the four gates of qualification is essent...
How Concentrated Stock Positions Get Unwound Tax-Efficiently
July 25, 2026
concentrated stock positions: A professional framework for managing concentrated equity positions, balancing the friction of capital gains taxes against the inherent risks of single-stock volatility and industry expos...
Backdoor Roth IRA: Avoiding the Pro-Rata Trap
July 24, 2026
pro-rata trap: A successful Backdoor Roth IRA depends on a clean IRA balance sheet. Learn how the IRS aggregation rule and Form 8606 determine the taxability of your conversion when pre-tax funds are present.
Section 199A QBI Deduction for Business Owners: 2026 Update
July 23, 2026
The Section 199A QBI deduction is now permanent under Public Law 119-21. Explore the updated 2026 income thresholds, expanded phase-in bands, and new minimum deduction rules for pass-through business owners.
Bunching Charitable Deductions With a Donor-Advised Fund
July 22, 2026
Bunching Charitable Deductions With a Donor-Advised Fund: Learn how donor-advised funds (DAFs) and deduction bunching strategies can help high-net-worth households navigate the standard deduction threshold and federal...
Tax-Efficient Withdrawal Sequencing for Retirees With $3M+ Portfolios
July 21, 2026
tax-efficient withdrawal sequencing: For high-net-worth retirees, the order of account distributions determines long-term portfolio longevity. Moving beyond basic rules of thumb helps manage RMDs and Medicare costs.
Capital Gains Harvesting in the 0% Bracket Years
July 20, 2026
capital gains harvesting: A low-income year can create a narrow opportunity to reset basis, diversify, and reduce future tax. Understanding the 0% long-term capital gains bracket is essential for effective retirement...
Roth Conversion Ladders: When They Help and When They Hurt
July 18, 2026
Roth Conversion Ladders: When They Help and When They Hurt: A Roth conversion ladder can create early-retirement liquidity and reduce future tax pressure. It can also turn a modest conversion into a much larger bill
Qualified Charitable Distributions (QCDs): A Powerful RMD Strategy
July 17, 2026
Qualified Charitable Distributions: A Qualified Charitable Distribution (QCD) allows IRA owners aged 70 1/2 or older to transfer funds directly to eligible charities, satisfying RMD requirements while excluding the di...
Net Investment Income Tax (NIIT): What Triggers It and How to Plan
July 16, 2026
Often overlooked in headline capital-gains rates, the 3.8% Net Investment Income Tax (NIIT) depends on both your modified adjusted gross income and your net investment income. Learn how the two-part test impacts house...
Charitable Bequests vs. Lifetime Giving: Tax Implications
June 30, 2026
Charitable Bequests vs. Lifetime Giving: Tax Implications: How to decide whether charitable intent belongs in the estate plan, the annual giving plan, or both June 26, 2026 Charitable planning usually beg...
Family Limited Partnerships for Real Estate Owners
June 29, 2026
Family limited partnerships for real estate owners: Discover how a family limited partnership (FLP) serves as a governance and wealth transfer tool for families with closely held real estate portfolios, focusing on co...
Asset Protection Trusts: What Oklahoma Allows
June 27, 2026
Oklahoma asset protection trusts: Oklahoma law provides specific tools like the Family Wealth Preservation Trust Act to protect growth and corpus from creditors, provided planning occurs before claims arise.
Crummey Powers in Trust Planning
June 26, 2026
Crummey powers in trust planning: Crummey powers transform trust contributions into present-interest gifts, allowing donors to leverage the annual gift-tax exclusion while maintaining long-term trust structures.
Power of Attorney: Financial vs Healthcare Documents
June 25, 2026
Financial vs Healthcare Power of Attorney: Most estate planning focus on what happens after death, but incapacity planning is equally vital. Discover the key differences between financial and healthcare powers of atto...
Funding Your Trust: The Step Most People Forget
June 22, 2026
Funding Your Trust: Creating a trust is only the first step; funding it is what makes it functional. Discover the practical Oklahoma process for retitling assets and using quitclaim deeds to ensure your estate plan pr...
Avoiding Probate in Oklahoma: A Step-by-Step Guide
June 21, 2026
Avoiding probate in Oklahoma: A professional look at how Oklahoma families coordinate trusts, deeds, and account titling to ensure assets transfer efficiently without unnecessary court administration.
Why Your Will Alone Is Not Enough at $2M+
June 20, 2026
Oklahoma estate planning: A will is a vital backstop, but for Oklahoma estates exceeding $2 million, it is rarely a complete operating system. Learn how probate commissions, asset titles, and settlement timelines impa...
Estate Planning Documents Every Oklahoma Family Needs
June 19, 2026
Estate planning documents every Oklahoma family needs: Estate planning is more than just tax strategy; it is a family operating manual. Learn which core documents are essential under Oklahoma law to ensure your wishes...
The Tide of Shares
June 19, 2026
supply of shares: While most analysis focuses on earnings and the Fed, the quiet force of shrinking stock supply through buybacks has shaped the long bull market over the last fifteen years.
529 Plans for Grandchildren: Superfunding Explained
June 18, 2026
Grandparent 529 plan superfunding: Explore how Oklahoma grandparents can use 529 plan superfunding to front-load $95,000 per grandchild using the five-year gift-tax election while managing estate planning trade-offs.
Irrevocable Life Insurance Trusts (ILITs): How They Work
June 17, 2026
How Irrevocable Life Insurance Trusts work: An Irrevocable Life Insurance Trust (ILIT) is a specialized estate planning tool designed to exclude life insurance proceeds from the insured's taxable estate through indepe...
Dynasty Trusts: Building Wealth That Lasts Generations
June 16, 2026
Discover how the 2026 tax landscape affects dynasty trusts and multi-generational wealth transfer. Learn how these structures manage GST exemptions and long-term asset protection.
Annual Exclusion Gifts: Stacking 529s and UTMAs
June 15, 2026
annual exclusion gifts: A guide to coordinating education savings and custodial gifts while navigating the 2026 annual exclusion limits to avoid unintended gift tax consequences.
Lifetime Gifting Strategies for Families With $10M+
June 14, 2026
lifetime gifting strategies: With the federal estate tax exemption rising to $15 million per person in 2026, high-net-worth families must evaluate lifetime gifting vs. step-up in basis at death to optimize wealth tran...
The Hidden Costs of "Buy and Hold" for Retirees Drawing Income
June 13, 2026
sequence-of-returns risk: While buy and hold works for savers, retirement changes the math. Discover why the order of investment returns can impact your portfolio's longevity once you begin taking distributions.
Healthcare in Early Retirement: Bridging to Medicare
June 13, 2026
Bridge to Medicare: Healthcare remains a critical variable for early retirees. With the return of the 400% income cliff in 2026, bridging the gap to Medicare at age 65 requires careful management of MAGI through strat...
Mega Backdoor Roth: Is It Right for High Earners in 2026?
June 12, 2026
Mega Backdoor Roth: A high-limit Roth strategy can be powerful in 2026, but only when employer plan design, cash flow, and tax pictures align for high-earning individuals.
How to Calculate Your Social Security Breakeven
June 8, 2026
Social Security breakeven: Understanding the arithmetic of Social Security claiming ages helps identify when a later, larger benefit surpasses earlier, smaller payments in total value.
The Better Way to Give From an IRA
June 3, 2026
The Better Way to Give From an IRA: Why a Qualified Charitable Distribution can beat writing the same check from a taxable account June 3, 2026 Charitable giving is usually framed a...
The Tax on Your Social Security Check
May 23, 2026
tax on your social security check: For many Oklahoma retirees, Social Security benefits are not tax-free. Learn how the federal government calculates the taxable portion of your check and how 2026 tax law changes affe...
Inflation, Hormuz, and the Ghost of 1973
May 22, 2026
1970s inflation parallel: With headline CPI reaccelerating and global energy chokepoints disrupted, we examine the similarities between today's economy and the 1970s inflation era.
Tax-Loss Harvesting: When Paying the Tax Is the Better Trade
May 20, 2026
Tax-Loss Harvesting: When Paying the Tax Is the Better Trade: Why a strategy that looks free on paper sometimes costs more than the tax it was supposed to save May 20, 2026 Tax-loss harvesting is one of the...
The Bond Buyer of Last Resort
May 15, 2026
bond buyer of last resort: Understanding the hierarchy of sovereign borrowers is essential for global bond market analysis. From reserve currency issuers to foreign-currency borrowers, here is how debt monetization im...
Reducing Capital Gains on a Highly Appreciated Portfolio
May 15, 2026
reducing capital gains: Managing a highly appreciated portfolio requires navigating the 23.8% federal tax cliff. Explore how to use Section 1014 step-up in basis and tax-loss harvesting to preserve purchasing power.
Charitable Remainder Trusts and the ILIT Wealth Replacement Strategy
May 15, 2026
Charitable Remainder Trusts and the ILIT Wealth Replacement Strategy: How a tool designed for charity can also leave heirs with more than they would have received outright. May 15, 2026 A charitable remainder t...
Debt, Income, and the Arithmetic That Cannot Be Ignored
May 8, 2026
Debt, Income, and the Arithmetic That Cannot Be Ignored Why the question is not just how much America and the world owe, but whether income is growing f...
Deferred Sales Trust Risks
May 6, 2026
Deferred Sales Trust risks: A Deferred Sales Trust (DST) is a marketing term for a complex installment sale structure. While appealing, it faces high IRS scrutiny regarding economic substance and constructive receipt...
Imputed Interest and the AFR
May 6, 2026
imputed interest and the AFR: When structuring installment sales, neglecting the Applicable Federal Rate (AFR) can lead to a 'quiet rewrite' by the IRS. Discover how sections 1274 and 483 govern interest rates to prot...
Why Delaying Social Security Isn't Always the Best Decision
May 2, 2026
Delaying Social Security: Conventional wisdom says to wait until age 70 to claim Social Security, but for many households, claiming at full retirement age or earlier can lead to better lifetime outcomes depending on h...
How the §453 Installment Method Actually Calculates Gain --- A Worked Example
April 29, 2026
§453 installment method: A step-by-step walkthrough of the §453 gross profit ratio, showing how the IRS prorates capital gains and basis recovery across multi-year installment payments.
Section 453, the Installment Sale, and the "453 Trust"
April 26, 2026
A deep dive into Internal Revenue Code Section 453, exploring the tax mechanics of business installment sales and the regulatory distinctions between legitimate deferral and marketed 453 trust structures.
Why this oil shock looks unlike anything since 1973
April 24, 2026
While the current Strait of Hormuz blockade represents the largest oil supply shock in history, the U.S. economic position today is fundamentally different than during the 1973 crisis due to record domestic production.
War, Oil, and the Path Forward
April 2, 2026
Assessing the Iran Conflict’s impact on markets, inflation, and portfolios — one month after U.S. and Israeli military action against Iran.
Avoiding Common Pitfalls in Net Unrealized Appreciation Planning
February 9, 2026
Understanding the Concept of Net Unrealized Appreciation (NUA) Net Unrealized Appreciation (NUA) is a tax strategy that allows investors to minimize their tax…
Social Security Planning
February 5, 2026
Social Security Planning: Understanding Social Security rules is essential for retirement. Navigate complex claiming options, delayed filing advantages, and family dynamics to manage your lifetime wealth.
How Interest Rate Levels Affect Lump Sum Values in Pension Plans
January 31, 2026
For many individuals planning for retirement, pension plans offer a crucial financial safety net. However, these plans’ stability and the lump sum values they…
Tax Strategies for Cattle Ranchers and Farmers
January 27, 2026
Tax planning is a critical component of managing a farm or ranch, providing opportunities to reduce liabilities and optimize financial outcomes.
Retiring Early? Here are 5 Things You Must Consider
January 22, 2026
Understanding the Concept of Early Retirement: Is It Right for You? Early retirement is a concept that has gained popularity in recent years, with movements…
Reinventing Yourself: How to Find Purpose and Fulfillment in Retirement
January 18, 2026
Understanding the Concept of Reinvention in Retirement: a time to relax and enjoy the fruits of years of work — but also to discover new purpose.
Leveraging RMD for Qualified Charitable Distribution: A Tax-Saving Strategy
January 14, 2026
Understanding the Basics of Required Minimum Distributions (RMDs) — mandatory withdrawals individuals must take from retirement accounts at certain ages.
Retirement & Taxes
January 9, 2026
Retirement and Taxes: a Perissos Private Wealth resource covering tax-smart withdrawal strategies, Social Security timing, and durable retirement income.
Navigating Retirement and Taxes: A Guide
January 5, 2026
Retirement planning is crucial for financial stability as we approach our golden years. One key component often overlooked is tax planning. In this blog post, w…
Social Security Basics
December 31, 2025
Social Security Basics: a Perissos Private Wealth resource covering tax-smart withdrawal strategies, Social Security timing, and building durable retirement income.
The Top Five Mistakes to Avoid for a Successful Backdoor Roth Conversion
December 27, 2025
Understanding the Concept of a Backdoor Roth Conversion: a strategy that allows individuals with high incomes to enjoy the benefits of a Roth IRA.
Navigating Social Security: The Top Five Filing Mistakes You Must Avoid
December 22, 2025
Understanding the Basics of Social Security: a federal program that provides financial support to retirees, disabled individuals, and their families.
5 mistakes to avoid when filing for medicare
December 18, 2025
Medicare, a federal health insurance program, is a crucial resource for individuals aged 65 and older — but filing mistakes can be costly to avoid.
How using a 1031 Exchange into a Private Real Estate Fund when selling Rental Property can save you taxes.
December 14, 2025
A 1031 Exchange into a Private Real Estate Fund is a strategic method used by property investors to defer capital gains taxes from rental property sales.
The benefits of Qualified Charitable Distributions from IRA
December 9, 2025
Qualified Charitable Distributions (QCDs) from an IRA offer significant benefits, particularly for those in their RMD years who give to charity.
The Pros and Cons of naming a CRUT or CRAT as the beneficiary of your IRA upon both spouses death
December 5, 2025
Naming a Charitable Remainder Unitrust (CRUT) or Annuity Trust (CRAT) as the beneficiary of your IRA — the pros, cons, and tax implications.
Maximizing Retirement Savings: 5 Reasons Small Business Owners Should Consider a Simple IRA or SEP IRA
November 30, 2025
The Importance of Maximizing Retirement Savings: a crucial aspect of financial management, especially for small business owners with variable income.
Four Phases of Retirement that aren’t related to finances
November 21, 2025
Four Phases of Retirement that aren't related to finances: a Perissos perspective on purpose, identity, relationships, and a fulfilling next chapter.
Secure Act 2.0 – 5 Changes to be Aware of When Planning For Retirement
November 17, 2025
Secure Act 2.0 — 5 Changes to Know When Planning for Retirement: contribution limits, RMD ages, and planning opportunities from Perissos Private Wealth.