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.
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.
Market Memo (Navigating War Markets)
March 9, 2026
Market Memo: Navigating War Markets. Perissos Private Wealth analysis of how geopolitical conflict affects inflation, oil prices, and equity returns.
Principles for Navigating War
March 5, 2026
Principles for Navigating War: a Perissos Private Wealth framework for handling geopolitical conflict and its effect on inflation, oil, and equities.
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.
Finding Purpose in Retirement
November 26, 2025
Finding Purpose in Retirement: a Perissos Private Wealth perspective on identity, relationships, and a fulfilling next chapter beyond the financials.
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.
Why I Disagree With Schwab’s Article on the Amount Needed to Retire Rule-of-Thumb
November 13, 2025
Why I Disagree With Schwab's Rule-of-Thumb: a Perissos perspective on why generic retirement rules fall short — and how a personalized plan changes the math.
Tithing from an IRA…Tax-Free
November 8, 2025
Tithing from an IRA Tax-Free: charitable giving strategies from Perissos — QCDs, donor-advised funds, and turning RMDs into tax-free generosity.
You’re telling me I could potentially increase my income during retirement?
November 4, 2025
You're telling me I could potentially increase my income during retirement? Planning ideas from Perissos for after-tax retirement income.
Should I Establish a Living Trust or A Will?
October 30, 2025
Should I Establish a Living Trust or A Will? Estate planning fundamentals from Perissos Private Wealth — wills, trusts, beneficiaries, and legacy.
2Q 2024 Market Update
October 26, 2025
2Q 2024 Market Update from Perissos Private Wealth. Analysis of economic trends, asset class performance, and portfolio positioning for the quarter.
Market Memo (Government Deficits)
October 13, 2025
Large U.S. Deficits and Bond Yields: What’s the Deal? Ever since Trump won the election, there’s been a lot of buzz about government deficits and their impact…
5 Types of Wealth (Part I)
October 4, 2025
Part 1: Time Wealth – The Currency of Life. What if the truest measure of wealth isn’t your bank account, but how you choose to spend your hours?
5 Types of Wealth (Part II)
September 29, 2025
Part 2: Social Wealth – The Power of Connection. Money might buy a yacht, but it won’t fill it with people you love. Relationships compound too.
5 Types of Wealth (Part III)
September 25, 2025
Part 3: Mental Wealth – The Mindset of Fulfillment. You can’t pour from an empty cup—or a cluttered one. Mental clarity makes wealth meaningful.
5 Types of Wealth (Part IV)
September 21, 2025
Part 4: Physical Wealth – Health as the Ultimate Asset. A billion dollars means nothing if you’re too sick to enjoy it. Health compounds like money.
5 Types of Wealth (Part V)
September 16, 2025
Part 5: Financial Wealth – Freedom, Not a Finish Line. We’ve saved the big one for last: how money supports the life you actually want to live.
Introduction to Estate Planning and Revocable Trusts (Part I)
September 12, 2025
Why Estate Planning Matters—and What’s a Revocable Trust Anyway? It might sound like something only the ultra-wealthy need to worry about, but it’s for everyone.
Introduction to Estate Planning and Revocable Trusts (Part II)
September 7, 2025
The Nuts and Bolts of a Revocable Trust. So, you’ve heard about revocable trusts, but how do they actually function? Let’s break it down step-by-step.
Market Memo (Tariffs)
September 3, 2025
Tariffs Through History and Trump’s 2025 Plan. Tariffs might sound like something from a dusty textbook, but they’re tools with real market consequences.
Introduction to Estate Planning and Revocable Trusts (Part III)
August 29, 2025
Why Choose a Revocable Trust? Top Advantages Explained Revocable trusts are a go-to estate planning tool for good reason.
Introduction to Estate Planning and Revocable Trusts (Part IV)
August 25, 2025
The Flip Side: What to Watch Out for with Revocable Trusts. They offer big benefits, but they’re not perfect for every estate planning situation.
Should I Consider Doing a Roth Conversion
August 16, 2025
Have you ever thought about converting a portion of your Traditional IRA to a Roth IRA.
Market Memo
August 7, 2025
In my last memo, I discussed how inflation could be disastrous for an economy, especially creditors/savers when left to its own devices. In this memo, I will ex…
How Might President Biden’s Tax Plan Affect Me?
August 3, 2025
President Biden’s administration has outlined a tax policy built upon the agenda introduced during his campaign. Biden’s tax plan focuses on raising taxes on co…
Market Memo
July 29, 2025
The Pandemic-induced recession is rapidly becoming a distant memory as the economy continues to show remarkable signs of regaining its footing. Consumer spendin…
What Issues Should I Consider Regarding My Incentive Stock Options?
June 28, 2025
Incentive Stock Options (ISOs) are a form of equity compensation, offering employees a share in the potential appreciation of a company’s value, with preferenti…
What Issues Should I Consider If I Lose My Job
June 24, 2025
People sometimes find themselves in the position of losing their job. In today’s economic uncertainty, business closures and layoffs are increasingly common. Th…
Social Security & Medicare Survival Guide
June 20, 2025
Retirement Planning and Social Security Planning can seem overwhelming. That’s why we wrote this little ebook with many of the confusing Social Security and Med…
Financial Planning Software
June 6, 2025
Watch this short explainer video to learn about the financial planning software we use to simplify the complexity of financial/retirement planning.
Market Memo
May 20, 2025
The Long-Term Debt Cycle Explained Today we saw the highest inflation rate since 1982 (6.8%), which I am sure you will see on the news tonight.
Will the Distribution From My HSA Be Tax & Penalty-Free
May 15, 2025
An HSA account is one of the most tax-efficient savings accounts available to investors. While many of the distribution rules are straightforward, there are sev…
Three Medicare Mistakes to Avoid
May 6, 2025
Many retirees think that once they reach age 65 the nightmare of navigating the maze of insurance choices will be over. I hate to break it to you, but the maze …
Five Things to Know When Considering Early Retirement
February 16, 2025
Five Things to Know When Considering Early Retirement from Perissos — healthcare, withdrawal strategy, and bridging the income gap to Medicare.
Healthcare in Retirement
February 11, 2025
Healthcare in Retirement – Retiring Early and Bridging the Gap to Medicare. Retiring early can be one of the best decisions you make if you plan well.
Planning for Long-Term Care
February 7, 2025
Effective financial planning is about saving, investing — and managing risk. The saving and investing part is usually focused on growing assets.
Five Things to Know About Roth Conversions
February 2, 2025
Five Things to Know About Roth Conversions: how conversions can reduce lifetime taxes, control RMDs, and create tax-free legacy wealth — by Perissos.
Creating Flexible Income in Retirement
January 29, 2025
Creating Flexible Income in Retirement: Roth Conversions. If you saved for retirement in a tax-deferred account, conversions can unlock optionality.
The Roth IRA Conversion as a Planning Tool
January 25, 2025
The Roth IRA Conversion as a Planning Tool: The Roth IRA was designed to provide tax benefits, but conversions amplify those advantages strategically.