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MONEY SMART WEEK PRESENTATION 
HOW TO MAXIMIZE AFTER TAX WEALTH 
THROUGH ASSET LOCATION, DEDICATION 
AND DIVERSIFICATION 
Donald D. Duncan MBA CPA CFA CFP 
President and Owner of D3 Financial Counselors 
April 10, 2014
5 TIPS TO MAXIMIZE AFTER TAX WEALTH 
• Three topic areas below all focus on increasing probability of achieving financial 
planning Goals by applying smart tax planning 
• Asset Location 
- Tax Qualified (non tax efficient assets) After Tax (tax efficient) 
• Asset Dedication 
- Education (529), Legacy (Roth IRAs), Charity (Donor Advised Funds) 
• Asset Diversification 
- Retirement Income Tax and Cash Flow (SO, RSU, ESPP) 
- Family Income Tax (SNT) 
- Best Retirement Plan (Cash Flow Sources) 
CFA Society Chicago 
2
ASSET LOCATION 
• Self directed IRAs for maximizing tax qualified investment flexibility 
• Brokerage accounts for after tax money 
• Life insurance cash value or annuities for deferring current investment income 
• Roth IRAs for legacy intentions and tax diversification 
• Donor Advised Funds 
• Gifting to a low tax bracket 
CFA Society Chicago 
3
ASSET DEDICATION 
• Specific financial planning goals have limited time lines, volatility constraints and 
tax implications 
• Dedicate specific assets with similar time lines 
• Dedicate specific assets with similar time horizon volatilities 
• Take advantage of specific account tax opportunities (529 Accounts, Donor 
Advised Funds) 
CFA Society Chicago 
4
ASSET DIVERSIFICATION 
• Modern portfolio theory based on “rational investors, independent and linear 
relationships and normally distributed price functions (unfortunately it does not explain 
the frequency of fat tail events i.e. black swans) 
• Modern portfolio theory, mathematically shows that diversification with non-correlated 
assets reduces portfolio risk and increases return 
• Diversification works in the financial markets, just not all the time 
• Post modern portfolio theory: the new normal is normal distributions cannot explain 
price functions if market participants are not always rational and move in the same 
direction 
• Asset Diversification is used to generate target cash flows 
- Focus on streams of cash flow that are non-correlated 
- Cash flow diversification buys time during fat tail events 
• Cash flow diversification is just as important as portfolio diversification from a financial 
planning success perspective (i.e. not running out of money or bailing out) 
CFA Society Chicago 
5
COMPLEXITY OF THE CURRENT TAX CODE 
CFA Society Chicago 
6
TAX BRACKET HARVESTING 
CFA Society Chicago 
7
EXAMPLES OF NON-CORRELATED, TAX 
DIFFERENTIATED CASH FLOWS 
• Bond Investment Interest Payments 
• Stock Investment Dividend Payments 
• Social Security 
• Pensions 
• Annuities 
• Rental Income 
• Equipment Leases 
• Royalties 
• Part time earnings 
• Life Settlements 
• Business Income 
CFA Society Chicago 
8
EXAMPLES TO MAXIMIZE AFTER TAX WEALTH 
• Asset Diversification 
- Retirement Income and Cash Flow Tax Bracket Harvesting (Stock Options, 
Restricted Stock Units, Employee Stock Purchase Plan) 
- Family Income Tax Bracket Arbitrage (Special Needs Trust) 
- Best Retirement Plan (Diversified, Non- Correlated Cash Flow Sources) 
CFA Society Chicago 
9
CONCLUSION 
• Situation: understand the unique aspects of the asset 
• Dedication: determine the specific purpose 
• Integration: use a consolidated/holistic viewpoint 
• Allocation: calculate the expected return 
• Diversification: understand asset correlations 
• Location: take advantage of tax opportunities 
• Liquidation: forecast tax brackets, longevity and liquidity 
CFA Society Chicago 
10
TAX BRACKET ARBITRAGE 
CFA Society Chicago 
11

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2014 CFA Chicago Money Smart Week - Don Duncan and David Blanchett

  • 1. MONEY SMART WEEK PRESENTATION HOW TO MAXIMIZE AFTER TAX WEALTH THROUGH ASSET LOCATION, DEDICATION AND DIVERSIFICATION Donald D. Duncan MBA CPA CFA CFP President and Owner of D3 Financial Counselors April 10, 2014
  • 2. 5 TIPS TO MAXIMIZE AFTER TAX WEALTH • Three topic areas below all focus on increasing probability of achieving financial planning Goals by applying smart tax planning • Asset Location - Tax Qualified (non tax efficient assets) After Tax (tax efficient) • Asset Dedication - Education (529), Legacy (Roth IRAs), Charity (Donor Advised Funds) • Asset Diversification - Retirement Income Tax and Cash Flow (SO, RSU, ESPP) - Family Income Tax (SNT) - Best Retirement Plan (Cash Flow Sources) CFA Society Chicago 2
  • 3. ASSET LOCATION • Self directed IRAs for maximizing tax qualified investment flexibility • Brokerage accounts for after tax money • Life insurance cash value or annuities for deferring current investment income • Roth IRAs for legacy intentions and tax diversification • Donor Advised Funds • Gifting to a low tax bracket CFA Society Chicago 3
  • 4. ASSET DEDICATION • Specific financial planning goals have limited time lines, volatility constraints and tax implications • Dedicate specific assets with similar time lines • Dedicate specific assets with similar time horizon volatilities • Take advantage of specific account tax opportunities (529 Accounts, Donor Advised Funds) CFA Society Chicago 4
  • 5. ASSET DIVERSIFICATION • Modern portfolio theory based on “rational investors, independent and linear relationships and normally distributed price functions (unfortunately it does not explain the frequency of fat tail events i.e. black swans) • Modern portfolio theory, mathematically shows that diversification with non-correlated assets reduces portfolio risk and increases return • Diversification works in the financial markets, just not all the time • Post modern portfolio theory: the new normal is normal distributions cannot explain price functions if market participants are not always rational and move in the same direction • Asset Diversification is used to generate target cash flows - Focus on streams of cash flow that are non-correlated - Cash flow diversification buys time during fat tail events • Cash flow diversification is just as important as portfolio diversification from a financial planning success perspective (i.e. not running out of money or bailing out) CFA Society Chicago 5
  • 6. COMPLEXITY OF THE CURRENT TAX CODE CFA Society Chicago 6
  • 7. TAX BRACKET HARVESTING CFA Society Chicago 7
  • 8. EXAMPLES OF NON-CORRELATED, TAX DIFFERENTIATED CASH FLOWS • Bond Investment Interest Payments • Stock Investment Dividend Payments • Social Security • Pensions • Annuities • Rental Income • Equipment Leases • Royalties • Part time earnings • Life Settlements • Business Income CFA Society Chicago 8
  • 9. EXAMPLES TO MAXIMIZE AFTER TAX WEALTH • Asset Diversification - Retirement Income and Cash Flow Tax Bracket Harvesting (Stock Options, Restricted Stock Units, Employee Stock Purchase Plan) - Family Income Tax Bracket Arbitrage (Special Needs Trust) - Best Retirement Plan (Diversified, Non- Correlated Cash Flow Sources) CFA Society Chicago 9
  • 10. CONCLUSION • Situation: understand the unique aspects of the asset • Dedication: determine the specific purpose • Integration: use a consolidated/holistic viewpoint • Allocation: calculate the expected return • Diversification: understand asset correlations • Location: take advantage of tax opportunities • Liquidation: forecast tax brackets, longevity and liquidity CFA Society Chicago 10
  • 11. TAX BRACKET ARBITRAGE CFA Society Chicago 11