Contents
1 The Foundation of Wealth
Human Capital: Skills, Education, Earnings Potential
Educating for an AI-Native Labor Market
The Shift from Human to Financial Capital in Retirement Planning
Social Capital
Executive Functions: The Engine Under Human Capital
Raising the Earner: Responsibility, Cultural Capital, and Scholastic Dispositions
Human Capital: Mind the Opportunity Cost
Human Capital Needs Protection
Financial Capital: Assets, Liabilities, Net Worth
The Golden Rule of Personal Finance: Spend Less Than You Earn
Goal Setting: Short-, Medium-, and Long-Term Financial Objectives
Spending Plan
Antifragility: The Spending Plan as a Survival Floor
Choosing a Spending-Plan Framework
The 50/30/20 plan
A Debt-Forward Alternative: The 1/3 Rule
Calculate Real Earnings and Spending
Savings Rate Basics
Secure Your Financial Future: Avoid Financial Pitfalls
Streamline Your Cash Flow
Establish an Emergency Fund
Layered Liquidity for Households
Invest Beyond Inflation
Asset Allocation Basics
Planning for Your Financial Future
Insurance is Important
Estate Planning Basics
Action Checklist
2 The Mathematics of Money
Inflation and Its Impact: Time Value of Money
Time Value of Money
Inflation over Several Years
Measuring Inflation
Causes Of Inflation
Interest Rates and the Fed
Compound Interest
Rule of 72
Compound Annual Growth Rate (CAGR)
Present vs. Future Value
Lifestyle Inflation: The Hedonic Treadmill That Keeps You Running in Place
The Psychology Behind Lifestyle Inflation
The Financial Consequences of Lifestyle Inflation
Escaping the Hedonic Treadmill: Strategies to Combat Lifestyle Inflation
Loan Amortization (Annuities)
Perpetuity
Discounted Cash Flow and Net Present Value
Internal Rate of Return (IRR)
Estimating Retirement Needs
Sequence of Returns Risk
Safe Withdrawal Rate — Why 4%?
Calculating Savings Rate
Savings Rate For Retirement
Financial Flexibility
Current Ratio
Debt-to-Total-Assets Ratio (D/TA)
Net Worth to Total Assets
Days not Working
Opportunity Cost: The Hidden Price Tag of Every Decision
Financial Leverage
Benefits of Financial Leverage
Risks Associated with Leverage
3 Financial Institutions and Services
Protect Your Assets: Strategic Protocols for Robust Banking Security
Multi-Factor Authentication (MFA)
Security of PIN Codes
Identity Theft
Defensive Protocols to Prevent Identity Theft
Warning Signs of Identity Theft
Incident Response Protocol
Categories of Ownership
Joint Tenancy with Right of Survivorship (JTWROS)
Tenancy in Common (TIC)
Payable on Death (POD) and Transfer on Death (TOD) Designations
Custodial Accounts (UGMA/UTMA)
Financial Services Industry
Depository Institutions: Liquidity and Capital Preservation
Brokerage Firms: Gateways to Capital Markets
Custodial and Trust Banks: Fiduciary Asset Holding
Checking Accounts and Transactional Capital Management
Overdraft Risk and Liquidity Mismatches
FDIC Insurance Optimization
Savings Accounts and Cash-Equivalent Alternatives
Debit Cards: Structural Risk and Liability Exposure
Revolving Credit Optimization and Transaction Arbitrage
Credit Utilization and Underwriting Architectures
Credit Scores and Underwriting Optimization
The FICO Scoring Model
Credit Profile Monitoring
Credit File Dispute Protocols
Brokerage Accounts: Gateways to Capital Allocation
SIPC Protection and Custodial Insurance
Securities Custody: Street Name vs. Direct Registration
Shareholder Governance: Activism and Proxy Voting
4 Income
Wage and Salary Income
Pre-Tax and Above-the-Line Adjustments
Importing Losses Against Wage Income
Low- and Moderate-Income Credits: EITC and CTC
Household Employment
As the Payer: The Nanny Tax
As the Receiver: Being a Household Employee
Equity Compensation
Restricted Stock: RSUs, RSAs, and the 83(b) Election
Stock Options: Mechanics, Valuation, and Dilution
Liquidity Events: IPOs and Acquisitions
What-If Scenarios and Financing
Taxation: ISOs, NSOs, and the AMT
Stock Appreciation Rights (SARs)
Employee Stock Purchase Plans (ESPPs)
Employee Stock Ownership Plans (ESOPs)
A Field Guide for Early Startup Employees
Farming and Fishing Income
Rental Income
Generational Wealth: Income for Children
The “Incorporate Your Kids” Myth
Active Income and Custodial Roth IRAs
The Kiddie Tax and Custodial Accounts
Taxation of Child’s Earned Income
Scholarships, Fellowships, and Dependency
Bankruptcy
5 Emergency Fund
Sizing the Fund
The Asymmetric Tier Framework
Assets That Pay for Emergencies
Constructing the Fund
Consider Taxation
Liquidity and Rolling Investing
Sinking Funds for Known Lumps
Quarterly Estimated Taxes
The RSU and Bonus Tax Gap
Uncalled Capital Commitments
Annual Renewals and Deductibles
Combining Sleeves and Refilling Discipline
Funding the Fund
Operating Cash: A Miller-Orr Frame for the Variable Part
The Three Cash-Flow Regimes
Miller-Orr on the Stochastic Residual
6 Tax Planning and Management
The Three Tax Systems
Three Types of Income
Bucket Rule
Tax Penalties
Safe Harbor
Filing status
The Senior Bonus Deduction (2025–2028)
Alternative Minimum Tax: Understanding and Navigating Its Impact
Tax Reporting Forms
Types of Form 1099
Forms You Need to File
Active (ordinary) income
Employment Income
Tax Withholdings
Supplemental withholding rate
Planning Tax Withholdings: Balancing Regular and Supplemental Income
Income Earned Abroad
Taxation of Fringe Benefits
Taxation of Flexible Spending Accounts (FSAs)
Investment Income
Net Investment Income Tax (NIIT)
Capital Gains/Losses
Tax-loss harvesting
Wash Sales
Trader Tax Status and the §475(f) Mark-to-Market Election
Opportunity Zone Deferral
Dividends
Interest
Taxation of Income from Bonds
Tax Planning for Selling Shares
Tax Reporting of Sales
Taxation of Series EE and Series I Bonds
Taxation of income from Master Limited Partnerships (MLP)
Section 754 Election and Partnership Inside-Basis Step-Up
Taxation of Options Trading
Collectible Tax Rates
Taxation of Hedging Contracts
Taxation of Forecast and Event Contracts (Kalshi-Style)
Taxation of Incentive Stock Options (ISO)
Taxation of Nonstatutory Stock Options
The Section 83(b) Election
Year-End Planning With Stock Compensation
Cryptocurrency and Digital Assets
Property, Not Currency
The Wash-Sale Gap
Staking, Mining, and Airdrops: The Tax Drag
Form 1099-DA and the End of Plausible Deniability
Where to Hold Yield: The SDIRA Wrapper
Retirement Income
Tax Reporting of Backdoor Roth IRA
Tax Reporting of Mega-backdoor Roth IRA
Tax Deductions of The Mortgage Interest
Mortgage Insurance Premiums
Home Mortgage Interest
Eligible Principal
Simple estimation of the deductible interest
Calculating the interest for partial year loans
Multiple Deductible Loans
Deductions
Business Income Deductions
Rental Income Deductions
The Oil and Gas Working-Interest Carve-Out
Rent and depreciation on equipment and machinery (Section 179)
Startup and Organizational Costs
Maximize Your Wealth: Smart Tax Strategies for Financial Growth
The Importance of Accuracy in Tax Returns
When You Hit a Wall With the IRS: The Taxpayer Advocate Service
Changing Tax Law
7 The Business Owner’s Tax Architecture
Hobby or Business?
Choosing a Business Entity
The Sole Proprietorship and the Single-Member LLC
Multi-Member LLC and Partnership
Professional Entities
The S-Corporation Election
Reasonable Compensation and the Break-Even Point
The C-Corporation
Conversion and Election Timing
Multi-Entity Structures: HoldCo, OpCo, and Series LLC
Entities With a Special Tax Regime
The Common Case: One or Two Founders
Business Tax Returns and Deadlines
Standing Up the Business
The Qualified Business Income Deduction
Qualified Small Business Stock
The Pass-Through Entity Tax
Operational Deductions and Family Employment
Paying for Work: Payroll and Information Reporting
Retirement Plans for the Self-Employed
Selling or Passing On the Business
Employee-Ownership Exits
Putting It Together
8 Tax Advantaged Accounts
Overview of Tax-Advantaged Accounts
Retirement accounts
Pre-tax 401(k)/403(b)/457(b)
After-tax 401(k) Plan
Roth 401(k)
457 Plans
Individual Retirement Arrangements (IRAs)
Keogh Plan
Practical Setup Guides for Self-Employed Plans
Maximize Contributions to Retirement Accounts
Trading Options in IRAs and Roth IRAs
Self-Directed IRA
Unrelated Business Taxable Income (UBTI)
Trump Child Savings Accounts
Early Withdrawal Penalty Minimization
Federal Employees Retirement System (FERS)
Choosing Between Pre-Tax and Post-Tax Retirement Accounts
Regulations Governing Contribution Limits to Qualified Retirement Plans
Tax Efficiency of Investments
Accounts For Medical Expenses
Health Savings Account (HSA)
Medical FSA
Limited-Purpose Flexible Spending Accounts (LPFSA)
Education And Dependent Care Accounts
Dependent Care Flexible Spending Account (DCFSA)
Coverdell Educational Saving Account (ESA)
529 Plans
529 Plan vs. Alternatives
College Funding Above the Aid Cutoff
Education Tax Credits and Anti-Double-Dipping Rules
The CSS Profile, in Detail
Front-Loading of Tax-Advantaged Accounts
Front-Loading for Early Termination
9 Investment Vehicles
Regulations
Stocks
Multiple Share Classes and Super-Voting Shares
Dividends, Value, and Growth
Bonds
Mutual Funds
Exchange-Traded Funds (ETFs)
Exchange-Traded Notes (ETNs)
Real Estate Investment Trusts (REITs)
Master Limited Partnerships (MLPs)
Private Equity
Initial Public Offering (IPO)
IPO Regulations
Securities Identification (CUSIP)
Derivatives
10 Measuring Risk and Performance
Financial Indicators
Key Financial Indicators to Monitor
Variance, Covariance, Correlation
Variance
Covariance
Correlation
Volatility
Emergence of Volatility
Measuring Volatility
Realized or Historical Volatility
Unrealized or Implied Volatility
“Beta” measure
Volatility Drag
Sharpe ratio
Sortino ratio
Omega Ratio
11 Asset Allocation
Constructing a Portfolio
Maximal vs. Optimal Portfolio Returns
Diversified Portfolio
Diversification Across Asset Classes
Asymmetry In Asset Correlation
Negative Correlation Between U.S. Treasury Bonds And Stocks
Diversification Across Sectors And Industries
Diversification Against Political Risks
Time Diversification
Diversification Summary
Tax Diversification
Tax Efficiency of Assets
Assigning Assets into Tax Buckets
Tax-Advantaged Accounts: Choosing Between Pre-Tax and Post-Tax Options
Taxable Accounts
Human Capital as an Asset
Human Capital and Its Relationship with Asset Classes
Human Capital and Asset Allocation Across the Life Cycle
Human Capital Models
Calculating Human Capital
Mortality Risk and Bequest Motives
Your House as an Asset
Basic Factors of Home Equity Value
Implications for Asset Allocation
Real estate market vs. Stocks and Bonds
Allocation by Age and Work Experience
Asset Allocation Models
Modern Portfolio Theory
MPT Under Deep Uncertainty
Portfolio Construction with Asymmetric Correlations
Post-modern Portfolio Theory (PMPT)
Black Litterman (BL) model
Stochastic Portfolio Theory (SPT)
Lazy Portfolios
Target Date Funds (TDFs)
Age-based Bond / Stock Ratio
Flight Path Model
Financial Samurai’s Allocation of Stocks and Bonds
The “All Weather Portfolio”
The “Optimal Portfolio” by Nick Maggiulli
Lazy Stocks-only Portfolio
Boglehead’s Lazy Portfolios
Lazy Portfolio for 401k
Lazy Portfolio for HSA
Tax-Efficient Retirement-Bucket Portfolios
Capital Deployment: Lump-Sum vs. Dollar-Cost Averaging
Dollar-Cost Averaging
Lump-Sum Investing
Rebalancing
Why Rebalancing Works
Rebalancing Methods
Tactical Overlays and the Limits of Timing
12 Investment Tools
Risk Tolerance of Investors
Conservative Profile
Moderate Profile
Aggressive Profile
Beyond the Questionnaire: Kelly Sizing and the Barbell
The Merton Share: Sizing the Equity Sleeve
Trading Horizon
Risks and Factors Affecting Investor Returns
Trading Securities: Stock Order Types
Primary Order Types
Time-in-Force Parameters
Conditional and Bracket Orders
Intraday Trading and Bid-Ask Spreads
Market Microstructure and Execution for Larger Orders
Margin Buying and Selling Short
Margin Buying: Leveraged Long Positions
Selling Short: Betting Against the Market
Fully Paid Securities Lending
Investing in Individual Stocks
Dividends and Tax Drag
Company Financial Indicators
Unlocking Corporate Insights: Forms 10-K, 10-Q, and 8-K
Valuing a Stock
Expected Return Frameworks
Intrinsic Valuation Models
Relative Valuation Models
Strip the Tailwinds Out of the Earnings Number
Don’t Mistake the Index for Diversification
Picking Stocks
A Taxonomy of Equity Profiles
Filing Deadlines and Market Capitalization
Fundamental vs. Technical Analysis
Active Stock Selection and Behavioral Traps
The Quality Framework
What Really Matters
The CANSLIM Growth Framework
Characteristics of Wealth-Creating Companies
The Corporate Life Cycle and Investing Implications
International Equities: ADRs, Funds, and the Foreign Tax Credit
Three Ways In — One of Them Wrong
Foreign Withholding Tax and the Credit That Reclaims It
Concentrated Stock Positions
Exchange Funds (Swap Funds)
Hedging and Monetization Alternatives
Preferred Stock
Bonds
The Fixed-Income Sleeve and the Inflation Regime
Pricing Mechanics, Yields, and Duration
Taxonomy of Fixed-Income Securities
Zero-Coupon Bonds and STRIPS
Five Fallacies of Fixed-Income Markets
Cash Equivalents and Liquidity Management
Money Market Accounts vs. Money Market Mutual Funds
Certificates of Deposit (CDs)
Laddering and Rolling Strategies
Mutual Funds
Pricing Mechanics and Alternative Fund Structures
The Frictions of Fees and Share Classes
Tax Inefficiency and the December Distribution Trap
The Structural Obsolescence of Mutual Funds in Taxable Accounts
Foreign Mutual Funds and the PFIC Tax Minefield
Exchange-Traded Funds (ETFs)
Comparison with Mutual Funds
Expense Ratio
Types of ETFs
ETF of ETFs
Exchange-Traded Notes (ETNs)
Taxation of ETNs
Selecting and Executing ETNs
Structured Products and Market-Linked Notes
Exchange-Traded Commodities (ETCs)
Futures Roll Yield: Contango and Backwardation
Taxation and K-1 Hazards of ETCs
REITs
Categorization of REITs
Investment Channels
Fundamental Analysis Metrics
REIT Taxation and the Asset-Location Arbitrage
Master Limited Partnerships (MLPs)
Distributions and the Return of Capital Mechanism
Estate Planning: The Basis-Step-Up Arbitrage
Tax Hazards: K-1s, Passive Loss Limits, and the UBTI Trap
MLP Funds and ETNs: Simplification Wrappers
13 Derivatives
Options
Understanding Option Writing
Understanding the Option Chain
Decoding Option Naming Conventions
Building Blocks of Options Strategies: Spread, Straddle, Collar, Strangle
Selling Options vs. Exercising Options
Writing Options for Premium
Speculative Investors and Options Trading
Breakeven Price for Options
Options: “In-the-Money”, “At-the-Money” and “Out-of-the-Money”
Option Greeks: Impact of Volatility on Options
0DTE Options and Dealer Gamma
Taxation of Options
Covered Call Strategy
Married (Covered, Protective) Puts
Bull Call Spread
Bear Put Spread
Protective Collar
Asymmetric Tail Hedging for Concentrated Equity
Long Straddle
Long Strangle
Long Call Butterfly Spread
Option LEAPS: Deep In-the-Money, Long-Term Bullish Strategy
Iron Condor
Iron Butterfly Strategy
Calendar Spread
Reverse Calendar Spread
Box Spread
Options Wheel Strategy
Futures
Futures Markets: Addressing Economic Need
Zero-Sum Game
Futures Pricing
Contracts
Margin Requirements
Mark-to-market of Positions
Futures Roll
Hedging Techniques
Speculating with Futures
Futures Options
14 Real Estate Investing
Key Terms in Real Estate Investments
Real Estate Property Classes Explained
Choosing Property for Real Estate Investments
Investment Strategy: A, B, or C Neighborhoods?
Defining A, B, or C Renovations
Remodeling and Renovations: Boosting Property Value
Getting a Mortgage for a Rental Property
Key Differences in Rental Property Mortgages
Paying Property Loans Using Rental Income via DSCR
Section 8 Rents: How to Rent Out to the State
Capitalization Rate (CAP rate)
Cash-on-Cash Return
Should You Invest in Real Estate?
Buying Foreclosure Homes
Steps to Buying a Foreclosed Home
Pros and Cons of Buying Foreclosure Homes
Types of Real Estate Investing to Avoid
Real Estate Properties to Avoid
Types of Real Estate Investing to Focus On
Investing Passively: Syndications and Private Real Estate Funds
Focus on One Market First
Tips for Real Estate Investments
Real Estate Rules to Live By
How to Raise Rent
Depreciation of Real Estate Property
Depreciation Systems
Calculating Annual Depreciation
The Magic of Cost Segregation
Bonus Depreciation
Partial Asset Disposition (PAD) Election
Qualified Improvement Property (QIP)
Short-Term Rentals
Return on Amenities
Regulatory Risk Is the Real Risk
The Short-Term Rental Loophole
Accounting for House Maintenance
Researching the HOA Before Buying a House
Real Estate Income Taxation
Real Estate Professional Status
Selling Houses
Deferred Sales Trusts
Delaware Statutory Trusts (DSTs)
Delaware Statutory Trusts Risks
Seller Financing
Beware of Squatting and Non-paying Tenants
Timeshares: Why They Aren’t Investments
Timeshares: Depreciation, Liquidity Problems, and Rising Costs
Avoiding Timeshare Scams
Buying Real Estate with an LLC
Potential Tax Benefits
Anonymity and Privacy
Mortgage and Financing
Risks and Downsides
Buying Real Estate from Foreign Persons: FIRPTA Withholding and Exceptions
FIRPTA Withholding Overview
Determining Foreign Status of the Seller
What Constitutes a U.S. Real Property Interest (USRPI)?
Withholding Rates and Special Rules
Exceptions to FIRPTA Withholding
Compliance Steps for Buyers of Real Estate from Foreign Persons
State-Specific Considerations
Investments in Qualified Opportunity Zones
Self-rental Strategies
Why Use Self-Rental?
Passive Activity Loss Rules
Grouping Election Workaround for Self-Rental Rules
Practical Considerations
Renting House to Yourself through an LLC
Personal Use of Rental Property
Multiple Residences
Personal Use Days
Special Rule for Short-Term Rentals
Dividing Expenses Between Rental and Personal Use
Deductible Rental Expenses
Investments in Foreign Real Estate
Start with the Local Tax Regime
Taxation on Foreign Real Estate Investments: U.S. Perspective
Ownership Structures and Reporting Requirements
Double Taxation Minimization
U.S. Tax Traps the Brochure Won’t Mention
Should You Use a U.S. LLC or Foreign Equivalent to Own Property?
Tax Forms and Regulations for U.S. Residents
15 Alternative Investments
Private Equity Investments
What Is Private Equity?
Private Equity Deal Types
How Private Equity Creates Value
Venture Capital
Angel Investing: The Art, Science, and Risk of Betting on the Future
Angel Investing and SAFE Notes
Underwrite the Numbers, Not the Pitch
The Qualitative Half: Team, Market, Co-Investors
Venture Capital Investments: How to Invest Through a VC
16 Loans
Asset Backed Loans (ABL)
Special Considerations for Asset-Backed Loans
Applying for an Asset-Backed Loan
Brokerage Firms and Rates
Lending Structures Above the Mass-Affluent Tier
Cash Value Life Insurance Loans
Insurance Premium Financing
Private Credit and Bespoke Single-Asset Lending
Cross-Border and Multi-Currency Lending
Borrowing from Your 401(k)
Lending to Friends and Family: Navigating the Financial and Emotional Minefield
Family Loans: The Gift Mindset Approach
Lending’s Memorandum of Understanding(MOU)
Structuring Intrafamily Mortgages for Deductibility
Interest Only (IO) Loans
Short Term Loans
Interest Payments on Short Term Loans
Decision to Pay-off
Car Loans
Student Loans
Federal Versus Private
Federal Loan Types in 2026
Income-Driven Repayment, Post-OBBBA
Public Service Loan Forgiveness
The Strategic Questions When You Can Afford to Pay
Home Loans/Mortgages
Mortgage Basics
Down Payment
Fannie Mae and Freddie Mac: Stabilizing the Mortgage Market
Conforming vs. Jumbo Mortgages
Assumable Mortgage Loans
Homeowner Assistance Fund (HAF)
Home Equity Loans
Home Equity Line of Credit
Cash-out Refinance
Home Equity Agreement
Reverse Mortgage
Interest Tracing: How Loan Use Determines Deductibility
Operating Rules: How to Trace Cleanly
The Tax-Deductible Debt Swap
17 Buying a House
Rent vs Buy decision
Consumption or Investment? Get the Definition Right
Dual Role of Houses: Durable Goods and Financial Investments
The Unrecoverable-Cost Framework
The NPV Framework: A Rigorous Buy-vs-Rent Comparison
Transaction Friction and the Break-Even Horizon
The House as a Single Point of Failure
The Mortgage as a Negative Bond
True Affordability in the Housing Market
Debt-to-Income Ratio (DTI)
Housing Ratio (HR1)
Broad Housing Ratio (HR2)
The Gross-DTI Trap for High Earners in High-Tax States
The 30/30/3 Home-Buying Rule
The Investment Showdown: Property Growth vs. Stock Market Gains
Leverage: The Secret Ingredient to Skyrocketing Your Investment ROI
Choosing Your Path: Debt-Free Peace vs. Leveraged Wealth Growth
Choosing the Right Mortgage: A Tale of Two Strategies
Surviving Job Loss: How Strategic Financial Planning Can Save Your Home
Private Mortgage Insurance
Jumbo Loan Microstructure
Do You Really Have to Buy a Home?
Calculating Financial Impact Of Buying A House
Home Location
Home Buying Process, Offer, Contingencies, and Mortgage
The Home Buying Process Overview
Home Loans
Home Loan Types
Impound Account vs. Non-Impound Account
Homeownership Taxes
Low-Down-Payment Conforming Programs (Conventional 97, FHA, VA)
Local Homebuying Programs
Understanding Contingencies
“Cash Offer” — No Loan Contingency
Obtaining Mortgages
Signing a Contract to Buy a House
Selling Primary House
18 Insurance: Shielding Your Assets and Family
Life Insurance
First-to-die Policy
Second-to-die Policy
Accidental Death and Dismemberment (AD&D) Insurance
Credit Life Insurance
Final Expense Insurance
Term Life Insurance
Perm or Cash-Value Life Insurance
Indexed Universal Life (IUL) Insurance
Private Placement Life Insurance (PPLI)
Life Insurance Cash-Outs
Estimating Life Insurance Needs
When to Buy Life Insurance
Policy Terms and Provisions Unique to Life Insurance
Settlement Options: Decision How to Receive Death Benefit
Taxation of Life Insurance
Annuities
Health Coverage Insurance
Use Health Insurance Efficiently
Medical Insurance
High Deductible Health Plan (HDHP)
Medicare
Dental Insurance
Vision Insurance
Long Term Care Insurance
Critical Illness and Accident Insurance
Disability Insurances: Covering Your Lost Income
The Contract Terms That Actually Matter at High Incomes
Job Protection for Family and Medical Leave
SSDI
Californians VPDI & SDI
VPDI vs. STD
VPDI vs. LTD
Long-term Disability (LTD) Insurance
Calculating Disability Insurance Coverage
Property and Liability Insurance
Homeowner’s and Renter’s Insurance
Auto Insurance
Umbrella Insurance
Professional Liability and Board Service Coverage
Asset Protection
The Pyramid
Federal Shields
State Shields
Umbrella and Excess Liability as the First Line
Entity Structures
The Trust Layer
The Fraudulent-Transfer Line You Must Not Cross
The Stack, Assembled
Diversify the Jurisdiction, Not Just the Portfolio
19 Charity
Charity
Planning Donations
Automate Donations
Double the Donation Through Employer
Charity And Taxes
Limits on Contributions
Reporting Requirements for Deductible Donations
Donate Appreciated Securities
Reducing Future Taxes or Balancing Portfolio
Use Donor Advised Funds (DAF)
Donate Every Other Year (Sometimes)
Creating Charity
Note on “Disqualified Persons”
Registering Your Charity
Promoting Your Charity
Using Your Charity for Tax Optimization
20 Retirement
Social Security
Calculating Social Security Benefits
Receiving Benefits While Working
SS Benefits for Families
Early or Late Retirement
Cost-Of-Living Adjustments
Impact on Replacement Rate
Claiming Strategy for Social Security
Pension From a Job not Covered by Social Security
Social Security as an Asset
Retirement Portfolio
Tools for Retirement Planning
Managing the Retirement Red Zone
The Pre-RMD Tax Window
Required Minimum Distributions: Navigating the Maze
The Math of Forced Liquidations
Strategies to De-risk the RMD Bomb
Annuities
Registered Index-Linked Annuities (RILAs)
Preparing for Retirement
Withdrawal Strategies in Retirement
Static Strategies
The Buckets Strategy
Financial Samurai’s Method
Dynamic Spending and Actuarial Models
Variable Percentage Withdrawal
TIPS Ladder as a Withdrawal Strategy
Pre-Retirement Checklist for a Larger Balance Sheet
21 Tax-Efficient Decumulation
What You Are Actually Optimizing
The Three Buckets and Their Tax Surface
The Default Sequence Is Wrong
The Conversion Window
The Social Security Tax Torpedo
Harvesting the 0% LTCG Bracket
The RMD Wall and How to Deflate It
Cliff Choreography
Buy, Borrow, Die in Retirement
What to Spend, What to Leave
Domicile and the Conversion Year
Late-Life Vulnerability: The Plan for Diminished Judgment
Putting the Pieces Together
22 The Economics of Marriage
The Merger
Prenuptial and Postnuptial Agreements
Separate Property, Community Property, and Commingling
The Marriage Penalty and the Marriage Bonus
Titling and Beneficiary Designations
The Divestiture: Divorce
Splitting Retirement Accounts
Alimony After the TCJA
Splitting the House
Social Security and the Ten-Year Rule
Administrative Triage
23 Estate planning
Key Concepts
The Documents You Actually Need
Matching Structures to Net Worth
Navigating Family Dynamics in Estate Planning
Wills
Preparing a Will
Considerations for Parents with Minor Children
On Naming Minor Children as Direct Beneficiaries
Managing Assets and Legal Rights for Unmarried Partners
What to Do if You Are Married
Family Communication
When to Revise Your Will
Incapacity Planning
What is Probate And How to Avoid it
Uniform Probate Code (UPC)
Estate Administration: How to Pass Assets on to Heirs
Payable Upon Death accounts (POD)
Revocable Living Trust
Trusts
Specific Regulations Covering Trusts
Primary Uses of Trusts
Creating a Trust: Step-by-Step
Selecting a Trustee: A Delicate Balance of Trust and Competence
Choosing a Corporate Trustee: Pros and Cons
Classification of Trusts
Revocable (Living) Trust
Keeping Your House Out of Probate
Irrevocable Trust
Testamentary Trust
Intentionally Defective Grantor Trusts (IDGTs)
Charitable Remainder Trusts
Testamentary Charitable Remainder Unitrust (T-CRUT)
Charitable Lead Trusts (CLTs)
Incentive Trusts
Special Needs Trusts
Grantor Retained Annuity Trusts (GRATs)
Qualified Personal Residence Trust (QPRT)
Marital Trusts: The QTIP and the A/B/C Structure
Bypass Trusts
Generation-Skipping Trusts (GSTs)
Dynasty Trusts
Spousal Lifetime Access Trusts (SLATs)
Blind Trusts
Domestic Asset Protection Trusts (DAPTs)
Directed Trusts
Top U.S. States for Trusts: Tax Benefits and Flexibility
Trust Accounting and Fiduciary Taxation
Offshore Trusts
LLCs for Estate Planning
Structure and Mechanics of the Family LLC
Valuation Discounts and IRS Scrutiny
Corporate Transparency Act, Costs, and Fiduciary Pitfalls
Taxation of Estate
Post-Mortem Planning: The Levers You Pull After Death
Capital Gains Resets With Inheritance
Optimizing for Basis in the High-Exemption Era
The Widow’s Penalty
Paying the Tax on an Illiquid Estate
Life Insurance Workaround
Gift Taxes
Digital Estate and Incapacity Planning
Two Kinds of Digital Asset
Why the Will Fails Here
RUFADAA: The Access Framework
The Incapacity Gap
Custody Architecture for Crypto
Elder Financial Abuse
Who the Abuser Is
Architecting the Defense
The Legal Backstop
What to Do in the Event of Death
Immediate Actions (First 72 Hours)
Managing Financial and Legal Affairs
The Fiduciary’s Administration Duties
Securing Accounts and Preventing Fraud
Tax Filing Requirements
Tax Planning for Inherited IRA
The Ten-Year Rule and Eligible Designated Beneficiaries
Annual RMD Requirements: The July 2024 Regulations
Distribution Optimization Strategies
Naming a Trust as Your Retirement-Account Beneficiary
How Do Family Fortunes Disappear?
A Finance Links
Personal Finance Links
Books on Personal Finances
Acronyms
Bibliography
References
Index
Alphabetical Index