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Tax-Efficient Investing: Tax-Sensitive Withdrawal Strategies (Part 4 of Tax-Efficient Investing Webinar Series)
 

Tax-Efficient Investing: Tax-Sensitive Withdrawal Strategies (Part 4 of Tax-Efficient Investing Webinar Series)

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This "Tax-Efficient Investing: Retirement Distribution Strategies" webinar is the last of a four-part series with Advisors4Advisors.com on tax-efficient Investing. ...

This "Tax-Efficient Investing: Retirement Distribution Strategies" webinar is the last of a four-part series with Advisors4Advisors.com on tax-efficient Investing.

You can view the on-demand webinar replay and receive CFP and IMCA CE credit at http://bit.ly/taxefficient4

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    Tax-Efficient Investing: Tax-Sensitive Withdrawal Strategies (Part 4 of Tax-Efficient Investing Webinar Series) Tax-Efficient Investing: Tax-Sensitive Withdrawal Strategies (Part 4 of Tax-Efficient Investing Webinar Series) Presentation Transcript

    • Tax Aware Investing -It’s the after Tax Return that Counts! Advisors4Advisors Part IV Presented by: Robert S. Keebler, CPA, MST, AEP (Distinguished) Stephen J. Bigge CPA, CSEP Peter J. Melcher JD, LL.M, MBA Keebler & Associates, LLP 420 S. Washington St. Green Bay, WI 54301 Phone: (920) 593-1701 Robert.Keebler@keeblerandassociates.comCircular 230 Disclosure: To ensure compliance with requirements imposed by the IRS, we inform you that any U.S. federal tax advice containedin this communication, including attachments, was not written to be used and cannot be used for the purpose of (i) avoiding tax-related penaltiesunder the Internal Revenue Code or (ii) promoting, marketing or recommending to another party any tax-related matters addressed herein. If youwould like a written opinion upon which you can rely for the purpose of avoiding penalties, please contact us.
    • Tax-Sensitive Withdrawal Strategies© 2011 Keebler & Associates, LLPAl Rights Reserved. 2 2
    • Tax-Sensitive Withdrawal Strategies • Managing capital gains and dividends – Short-term capital gains • Held 1 year or less – Long-term capital gains • Held more than 1 year – Taxpayers in the 10 & 15% tax bracket • 0% rate (2011-2012) • 5% rate (2013) – Taxpayers in a tax bracket greater than 15% • 15% rate (through 2012) – Qualifying dividends (through 2012) • 15% for tax payers in tax brackets greater than 15% • 5% for tax payers in the 10% or 15% tax bracket© 2011 Keebler & Associates, LLPAl Rights Reserved. 3
    • Tax-Sensitive Withdrawal Strategies • Manage taxation of Social Security benefits • Manage income tax brackets • Select high-basis securities to sell first • Aggressively harvest outside portfolio losses • Defer Roth IRA distributions • Implement Roth conversions • Tax efficient use of annuities • Manage charitable gifts • 3.8% Medicare “surtax”© 2011 Keebler & Associates, LLPAl Rights Reserved. 4
    • Assessing the Primary Issues • Which assets should a client spend first? • When should a client do a Roth conversion? • Understanding the advantages and disadvantages of taking stock from a qualified plan • When and how to draw non-qualified annuities • When and how to draw deferred compensation • When and how to draw low basis securities • When and how to exercise NSOs and ISOs© 2011 Keebler & Associates, LLPAl Rights Reserved. 5
    • Tax-Sensitive Withdrawal Strategies Interest Capital Gain Tax Exempt Pension Real Estate, Dividend and Oil & Gas Roth IRA and Income Income Interest Income IRA Income Insurance - Taxable -Preferential Rate - Tax Preferences - Tax Free -Deferral until - Tax Deferred Growth/ sale Benefits• Money • Equity • Equity • Bonds issued by • Pension plans Real Estate Roth IRA market securities Securities State and local • Profit sharing • Depreciation • Tax-free• Corporate Governmental plans tax shield growth during bonds Attributes Attributes entities • Annuities • 1031 lifetime• US Treasury • Qualified • Deferral exchanges • No 70½ RMD bonds dividends at until sale Attributes Attributes • Deferral on • Tax-free LTCG rate • Reduced • Federal tax • Growth during growth until distributionsAttributes • Return of capital gains exempt lifetime sale out to• Annual capital rate • State tax exempt • RMD for IRA beneficiaries income tax dividend • Step-up and qualified Oil & Gas life expectancy on interest • Capital gain basis at plans • Large up• Taxed at dividends death • No step-up front IDC Life Insurance highest deductions • Tax-deferred marginal • Depletion growth rates allowances • Tax-exempt payout at death © 2011 Keebler & Associates, LLP Al Rights Reserved. 6
    • Tax-Sensitive Withdrawal Strategies Top Planning Ideas 1.Fill-up the 10% or 15% bracket 2.Roth conversions by asset class and Roth conversions to manage tax brackets 3.Spend from the outside portfolio first once you have “filled up” the 15% bracket 4.Bonds should generally be positioned in one’s IRA because of the annual tax burden 5.Life insurance can be a very valuable supplement to existing pensions© 2011 Keebler & Associates, LLPAl Rights Reserved. 7
    • Tax-Sensitive Withdrawal Strategies Early Accumulation Years (Ages 25-45) Key Tax Concepts • Maximize qualified retirement savings • Maximize IRA accounts • Position some funding in Roth IRAs or Roth 401(k) • Review whole life or universal life insurance • Deferral via annuities • Low-risk Oil & Gas transactions • Low-risk Real Estate transactions • Focus on low turnover strategies© 2011 Keebler & Associates, LLPAl Rights Reserved. 8
    • Tax-Sensitive Withdrawal Strategies Core Accumulation Years (Ages 46 - Retirement) Key Concepts • Continue to apply key concepts form early years • Aggressively manage taxation of wage earnings – Retirement plans – Deferred compensation • Aggressively manage taxation of investments© 2011 Keebler & Associates, LLPAl Rights Reserved. 9
    • Tax-Sensitive Withdrawal Strategies At Retirement - Key Concepts • Evaluate rollover of pensions and profit sharing plan • Evaluate asset protection issues • Manage Net Unrealized Appreciation (NUA) opportunities • Monitor the 10% IRC §72(t) penalty • Manage basis in both IRAs and qualified plans • Manage qualified Roth Distributions© 2011 Keebler & Associates, LLPAl Rights Reserved. 10
    • Tax-Sensitive Withdrawal Strategies Early Retirement Years (Retirement to Age 70) Key Concepts • Manage the 10% and 15% tax brackets • Generally defer IRA distributions taxed at 25% or greater • Draw upon “outside” assets and deferred compensation first • Draw upon traditional IRA assets second • Draw upon Roth IRA assets last • Review Roth conversions to manage tax brackets© 2011 Keebler & Associates, LLPAl Rights Reserved. 11
    • Tax-Sensitive Withdrawal Strategies Later Retirement Years (After Age 70) Key Concepts • Manage the 10% and 15% tax brackets • Take all Required Minimum Distributions (RMDs) • Spend down high basis outside assets • Draw additional funds from IRA to manage tax brackets • Update estate planning© 2011 Keebler & Associates, LLPAl Rights Reserved. 12
    • Tax-Sensitive Withdrawal Strategies • Consider the tax structure of the account as you allocate assets – Income producing assets in traditional IRA – Capital gains assets (especially those you intend to hold for a long period) in a taxable account – Roth IRA Rapid Growth The illustration is NOT Bonds Stock intended to be a recommendation, but to IRA $250,000 $250,000 $500,000 provoke thought. As you know, asset allocation should be determined according to Taxable Account risk tolerance and time $250,000 $250,000 $500,000 horizon. Tax sensitivity would be considered secondarily.© 2011 Keebler & Associates, LLPAl Rights Reserved. 13
    • Tax-Sensitive Account• Allocation Orange = position the investor would be at under the original 50% stock / 50% bond investment mix• Blue = additional $63,890 of additional growth the investor would achieve by placing 100% bonds in IRA• Assumptions: Bonds and the stock both generate a 7% return on a pre-tax basis. The stock earnings are deferred until the time of sale, then taxed as long-term capital gains. The amount of any tax savings from a deductible IRA contribution is invested in a taxable investment account earning the same yield as the IRA. The values shown for the IRA include the value of the taxable investment account. The client is in the 25% ordinary income tax bracket (15%* for capital gains purposes) Integrating Account Tax Structure with Asset Allocation (100% Bonds in IRA vs. 50/50 Mix of Stock and Bonds in IRA) 2,800,000 Option A - 100% Bonds in IRA Option B - 50/50 Mix in IRA 2,550,000 $63,890 of additional assets (2.6% increase) 2,300,000 * The 15% long-term capital gain rate is only effective under current law through 2,050,000 2010. It is not certain that the Congress will extend the 15% rate. 1,800,000 10 11 12 13 14 15 © 2011 Keebler & Associates, LLP Al Rights Reserved. 14
    • • Effect of Capital Gains Incentives Example: – $100,000 beginning cash to invest and 28% tax bracket (15% long-term capital gains bracket) – Options: • Corporate bonds (6% annual interest) • Municipal bonds** (4.5% annual interest) • Stocks (1% annual non-qualified dividends, 5% growth [100% asset turnover])After-Tax Balance of a Taxable Account (Invested in Stock, Municipal Bonds and Corporate Bonds) $400,000 Stock (50% Turnover) Stock (100% Turnover) $65,732 of $300,000 additional assets Municipal Bonds Corporate Bonds (23% difference) $200,000 $100,000 $- 1 3 5 7 9 11 13 15 17 19 21 23 25 Year•The 15% long-term capital gain rate is only effective under current law through 2012. It is not certain that the Congress will extend the 15% rate.•**Municipal bounds may not be suitable for a person in this low of a tax bracket.© 2011 Keebler & Associates, LLPAl Rights Reserved. 15
    • Tax-Sensitive Distribution Strategies • Importance of a solid distribution strategy • Four key issues to consider when structuring a distribution portfolio: – Which retirement investment vehicles (tax-sensitive account allocation) to include in the distribution portfolio – The order in which plan assets should be withdrawn – Loss harvesting and the specific identification method – Tactical income tax planning with defined benefit plans, tax-deferred annuities, Net Unrealized Appreciation, and Roth conversions© 2011 Keebler & Associates, LLPAl Rights Reserved. 16
    • Tax-Sensitive Distribution Strategies • Timing is Everything – which tax-sensitive account should be used first • Best result comes from withdrawing funds in a manner that produces the most favorable overall income tax consequences. (Be sure to consider heirs’ income tax brackets) • Some general (simplistic) concepts to consider – remember every client is different – Utilize taxable accounts first – Sell high basis assets first – Utilize IRA to manage tax brackets – Defer Roth IRA distributions – Carefully implement Roth conversions© 2011 Keebler & Associates, LLPAl Rights Reserved. 17
    • Tax-Sensitive Distribution Strategies • Principle #1: Determining which tax-favored account to withdraw from first – Deals with the timing of withdrawals between tax- deferred assets (e.g. Traditional IRAs) and tax-free assets (e.g., Roth IRA) – Theory: If a retiree makes equal, after-tax withdrawals from tax-deferred and tax-exempt accounts, the order of the withdrawals between the two accounts will not affect the longevity of the withdrawal period of the two accounts – Assumptions: The assets in each account must both be growing tax-deferred at the same rate of return and the income tax rate must remain flat over the period of the analysis© 2011 Keebler & Associates, LLPAl Rights Reserved. 18
    • Tax-Sensitive Distribution Strategies• Principle #1 - Example 1: Traditional Roth IRA Assumes a 6% return IRA First First Initial balance - Traditional IRA $100,000 $100,000 Initial balance - Roth IRA $100,000 $100,000 Federal income tax rate - Traditional IRA 28.00% 28.00% Annual after-tax cash flow needed $15,000 $15,000 Annual pre-tax withdrawal $20,833 $15,000 Period until exhaustion - Initial asset 5.8 8.8 Period until exhaustion - Remaining asset 14.2 11.2 Maximum withdrawal period (years) 20 20• No matter which account tax structure is depleted first, the maximum withdrawal period for both account tax structures is the same• Assumes a 6% annual beginning of period return; a simple 28% tax rate; and distributions are sufficient to cover any RMDs.This is a hypothetical example for illustrative purposes only.© 2011 Keebler & Associates, LLPAl Rights Reserved. 19
    • Tax-Sensitive Distribution Strategies 100% Traditional IRA First 50/50 Mix Initial balance - Traditional IRA $100,000 $100,000 Initial balance - Roth IRA $100,000 $100,000 Annual after-tax cash flow needed $15,000 $15,000 Annual pre-tax withdrawal – Traditional IRA (15% tax rate) $8,824 $8,824 Annual pre-tax withdrawal – Traditional IRA (28% tax rate) $10,417 - Annual pre-tax withdrawal – Roth IRA - $7,500 Annual pre-tax withdrawal (First 6 years comparison) $19,241 $16,324 Period until exhaustion – initial asset 6.4 19.6 Period until exhaustion - Remaining asset 14.9 3.6 Maximum withdrawal period (years) 21.3 23.3 • By spreading out distributions over taxable & nontaxable accounts you may be able to keep your client in the marginal income bracket. • Assumes a 6% annual beginning of period return; a simplified hypothetical marginal tax rate of 15% on the first $8,824 of income and 28% thereafter to achieve the 50/50 after-tax distribution mix; no other taxable income; and distributions are sufficient to cover any RMDs. (This is a hypothetical example for illustrative purposes only.)© 2011 Keebler & Associates, LLPAl Rights Reserved. 20
    • Tax-Sensitive Distribution Strategies • Principle #2: Things to consider when determining whether to withdraw from tax-favored versus taxable accounts – May be advisable to spend down taxable investment assets first followed by tax-deferred investment assets. But, consider the issue of large step-up in basis potential for elderly clients. – If client expects to be in the same or lower tax bracket than beneficiaries, consider client bearing a portion of the tax at their lower rate.© 2011 Keebler & Associates, LLPAl Rights Reserved. 21
    • Tax-Sensitive Distribution Strategies • Principle #2 – Example: Client, age 60 and single, has a $500,000 taxable account and a $500,000 Traditional IRA – Needs $60,000 annually for living expenses – Receives $12,000 of Social Security beginning at age 62 • Assumptions: Annual return consists of 3% ordinary income (i.e. interest income) and 4% growth on the value in each account. The stock earnings are tax deferred until the time of sale, then taxed as long-term capital gains. Basis on the sale is determined as a percentage of the total account value. Required Minimum Distribution (RMD) begins at age 70½, regardless of the intended distribution ordering. If the RMD and the income from the taxable account exceed the living expenses for a year, the excess is reinvested in the taxable account. 25% ordinary income tax rate, 15% capital gains tax rate, 85% of Social Security benefits are subject to income tax Benefit of Withdrawing Funds from a Taxable Account First Balance at a Particular Year Withdraw From Taxable Investment Account First $1,633,578 Withdraw From Traditional IRA First $529,519 of $1,316,362 additional assets $1,084,493 $1,104,059 $984,410 $1,005,256 (48% difference) Age 65 75 85© 2011 Keebler & Associates, LLPAl Rights Reserved. 22
    • Tax-Sensitive Distribution Strategies In Theory • Other considerations: future tax rates • Some general (simplistic) distribution order to consider – Remember every client is different Tax Roth Deferred 401(k) – Taxable investments Accounts – Traditional IRAs and qualified retirement plans – Roth IRAs and Roth 401(k)s Investment Accounts Discuss with tax advisor prior to having elderly clients sell assets that could have received a step-up in basis© 2011 Keebler & Associates, LLPAl Rights Reserved. 23
    • Tax-Sensitive Withdrawal Strategies 2011 Tax Brackets Married Qualified Married Filing Head of Single Widow(er) Filing Jointly Separately Household 10% Tax Rate $8,500 $17,000 $17,000 Stock $8,500 IRA $12,150 15% Tax Rate $34,500 $69,000 $69,000 $34,500 $46,250 25% Tax Rate $83,600 $139,350 $139,350 $69,675 $119,400 28% Tax Rate $174,400 $212,300 $212,300 $106,150 $193,350 33% Tax Rate $379,150 $379,150 $379,150 $189,575 $379,150 35% Tax Rate > $379,150 > $379,150 > $379,150 > $189,575 > $379,150 Source: Internal Revenue Service© 2011 Keebler & Associates, LLPAl Rights Reserved. 24
    • Tax-Sensitive Distribution Decision Matrix • Spend-down strategy should be structured in a way so as to maximize economic returns while minimizing income taxes • Factors to consider – Investment returns within each account tax structure – Current and projected future income tax rates – Taxability of Social Security – Required Minimum Distributions – Long-term strategic goals • Decision matrix: Future income at the Future income taxed at same or lower tax rate higher tax rate 1) Taxable account 1) Tax-deferred account 2) Tax-deferred account 2) Taxable account 3) Tax-free account 3) Tax-free account© 2011 Keebler & Associates, LLPAl Rights Reserved. 25
    • Loss Harvesting and the Specific Identification Method • Loss harvesting, especially in volatile markets, will often have a meaningful impact on the effective capital gains tax rate • The truly sophisticated financial advisor will also integrate the benefits of the specific identification method when selecting which particular mutual funds (provided average cost has previously not been used on the account) or securities to sell© 2011 Keebler & Associates, LLPAl Rights Reserved. 26
    • Tactical Income Tax Planning • Defined Benefit Plans – Distributions from a defined benefit plan will almost always generate ordinary income in the year received – There is a greater need for tactical tax-sensitive asset allocation planning when defined benefit plans are part of the retirement distribution equation© 2011 Keebler & Associates, LLPAl Rights Reserved. 27
    • Tactical Income Tax Planning • Non-Qualified Tax-Deferred Annuities – Provides a client with the right to receive annual (or more frequent) payments over his life or for a guaranteed number of years – Unless a tax-deferred annuity is annuitized, the taxpayer is generally deemed to withdraw ordinary income first and then tax-free basis. This income tax consequence may be mitigated – One might purchase these investments in different tax years and then annuitize them over a period of years© 2011 Keebler & Associates, LLPAl Rights Reserved. 28
    • Tactical Income Tax Planning • Employer securities in a qualified plan (Net Unrealized Appreciation) – Difference between Fair Market Value at distribution and basis is Net Unrealized Appreciation (NUA) – NUA is currently taxed at long-term capital gain tax rates (currently 5% / 15%) – Example: • Fair Market Value of stock $ 750,000 • Employer basis $ 150,000 • Net Unrealized Appreciation (NUA) $ 600,000 • Amount taxable as ordinary income if stock is distributed and not sold $ 150,000 Distribution must qualify as a lump sum distribution employer stock be a “qualified employer security” 10% penalty may apply on the basis based on individual’s age© 2011 Keebler & Associates, LLPAl Rights Reserved. 29
    • Tactical Income Tax Planning • Qualified Plan Rollovers – When rolling funds from a qualified plan to an IRA one has a choice of rolling over or not rolling over after-tax funds (i.e., basis) – Strong consideration should be given to not rolling over after-tax funds and utilizing these proceeds to fund a Roth conversion or spend on a tax-free basis© 2011 Keebler & Associates, LLPAl Rights Reserved. 30
    • Other Planning Considerations© 2011 Keebler & Associates, LLPAl Rights Reserved. 31
    • Net Unrealized Appreciation (NUA) • Under the tax law, if an employee has employer securities in his/her qualified retirement plan, he/she may be able convert a portion of the total distribution from the plan from ordinary income into capital gain income • In order to achieve this favorable tax treatment, the distribution from the qualified retirement plan must be made pursuant to a “lump-sum distribution” • To qualify as a “lump-sum distribution” the distribution must be made pursuant to a “triggering event”© 2011 Keebler & Associates, LLPAl Rights Reserved. 32
    • Net Unrealized Appreciation (NUA) “Triggering Events” • On account of employee’s death • After the employee attains age 59½ • On account of employee’s “separation from service” • After the employee has become disabled (within the meaning of section 72(m)(7)) CAUTION: If prior year distributions have been made after one triggering event, the taxpayer must wait until another triggering event to qualify for lump sum distribution “within one taxable year” rule.© 2011 Keebler & Associates, LLPAl Rights Reserved. 33
    • Net Unrealized Appreciation (NUA) Taxation of Lump-Sum Distribution Fair Market Value (FMV) of stock $750,000 Employer basis $150,000 Net Unrealized Appreciation (NUA) $600,000 Amount taxed at rollout $150,000© 2011 Keebler & Associates, LLPAl Rights Reserved. 34
    • Net Unrealized Appreciation (NUA) Taxation of Lump-Sum Distribution • Ordinary income recognized on cost basis • If taxpayer is under age 55 at the time of distribution, the taxpayer must also pay the 10% early withdrawal tax on the cost basis • Difference between FMV at rollout and cost basis is Net Unrealized Appreciation (NUA) • NUA is not taxed at the time of distribution, but rather at a later time when the stock is sold • NUA is taxed at long-term capital gain tax rates (0%/15%) • Ten-year averaging and 20% capital gain • Only available to those individuals born before 1/2/1936 • 20% capital gain only applies to pre-1974 contributions© 2011 Keebler & Associates, LLPAl Rights Reserved. 35
    • Net Unrealized Appreciation (NUA) Taxation of Post-Distribution Gain • Holding period one year or less from time of distribution = short-term capital gain • Holding period greater than one year from time of distribution = long-term capital gain© 2011 Keebler & Associates, LLPAl Rights Reserved. 36
    • Net Unrealized Appreciation (NUA) Taxation of NUA at Death • NUA does not receive a step-up in basis • However, subsequent gain above NUA should receive a step-up in basis • If an estate or trust contains NUA stock, a fractional funding clause must be used • Otherwise, the NUA will be subject to immediate taxation© 2011 Keebler & Associates, LLPAl Rights Reserved. 37
    • Compensatory Stock Options: NQSOs and ISOs© 2011 Keebler & Associates, LLPAl Rights Reserved. 38
    • Compensatory Stock Options Two Types of Options • Non-Qualified Stock Options (NQSOs) • Incentive Stock Options (ISOs)© 2011 Keebler & Associates, LLPAl Rights Reserved. 39
    • Compensatory Stock Options Non-Qualified Stock Options (NQSOs) • Any stock option that does not qualify for special tax treatment under IRC 422 • May be transferable • No specific holding period requirements • Employer receives an income tax deduction for the difference between the strike price and the fair market value of the securities on the date of exercise© 2011 Keebler & Associates, LLPAl Rights Reserved. 40
    • Compensatory Stock Options Non-Qualified Stock Options (NQSOs) “Cashless Exercise” • The exchange of previously acquired stock (not subject to any holding period requirement) for the funding price of new shares is a tax-free exchange. • The basis and holding period of the old stock are carried over (i.e. “tacked”) to the same number of shares acquired in the exchange. • The basis in the excess shares is equal to the income recognized on the transaction (the fair market value), and the holding period begins with the date of exercise.© 2011 Keebler & Associates, LLPAl Rights Reserved. 41
    • Compensatory Stock Options Non-Qualified Stock Options (NQSOs) Tax Consequences• Ordinary income is recognized on the difference between the strike price and the fair market value of the stock on the exercise date.• FICA and Medicare are applicable to the ordinary income.• The subsequent appreciation will be subject to capital gain. The holding period will determine whether the gain will be long- term or short-term.• The holding period for purposes of determining the correct capital gain rate begins with the exercise date.• The basis of the stock is the exercise price plus the amount of income recognized upon the exercise of the option.© 2011 Keebler & Associates, LLPAl Rights Reserved. 42
    • Compensatory Stock Options Non-Qualified Stock Options (NQSOs) Tax Consequences $100 FMV at sale FMV at exercise Short or long- term capital gain Compensation income $0 Strike price© 2011 Keebler & Associates, LLPAl Rights Reserved. 43
    • Compensatory Stock Options Incentive Stock Options (ISOs) Requirements • The stock option plan is in writing • The plan specifies the number of shares that can be purchased under the plan, as well as the eligible employees • The FMV of the stock with respect to which the options are exercisable for the first time does not exceed $100,000 during any calendar year • The options must be exercised within ten years after they are granted • The options are exercisable only by the employee during his or her life • The options are transferable only upon the death of the employee© 2011 Keebler & Associates, LLPAl Rights Reserved. 44
    • Compensatory Stock Options Incentive Stock Options (ISOs) Requirements • The employee must be employed by the issuing corporation at all times from the option grant date until three months after the date of exercise • The stock acquired under the option must be held for at least two years after the time it is granted and one year after the time it is exercised • If an option is granted to a 10% or greater shareholder, the exercise price must be at least 110% of the FMV of the stock subject to the option • The employer’s shareholders must approve the plan within twelve months before or after the employer’s board of directors adopts the plan • The option is granted within ten years of the plan’s adoption by the board of directors or, if earlier, the date it is approved by the shareholders© 2011 Keebler & Associates, LLPAl Rights Reserved. 45
    • Compensatory Stock Options Incentive Stock Options (ISOs) “Cashless” Exercise • Stock acquired from a means other than a previous ISO or stock acquired from a previous ISO that is held for the required period of time can be used for a stock swap. • The exercise of an ISO with a stock swap will not trigger ordinary income (but could trigger AMT). • The basis and holding period for the shares surrendered tack to the same number of share acquired in the swap. However, the holding period of the old shares does not tack for purposes of the special holding requirements of the ISO stock.© 2011 Keebler & Associates, LLPAl Rights Reserved. 46
    • Compensatory Stock Options Incentive Stock Options (ISOs) “Disqualifying Disposition” If the stock acquired by the exercise of an ISO is disposed of before one year has lapsed from the exercise date or two years from the issue date, the sale will be subject to the following recapture rules: • Ordinary income is recognized on the difference between the exercise price and the fair market value at the time of exercise. • FICA and Medicare withholding will not apply • In addition there will be short or long term capital gain on the difference between the fair market value at the time of exercise and the selling price.© 2011 Keebler & Associates, LLPAl Rights Reserved. 47
    • Compensatory Stock Options Incentive Stock Options (ISOs) Tax Consequences $100 FMV at sale FMV at exercise AMT Regular capital gain capital gain (short or long-term) AMT adjustment $0 Strike price© 2011 Keebler & Associates, LLPAl Rights Reserved. 48
    • Compensatory Stock Options Exercise Considerations • Opinion of experts • Historical returns • Fundamental analysis--look at data about company, ratios, statistics, etc. • Security market line • Importance of expert investment counsel to your client • Important for setting inputs for option exercise model© 2011 Keebler & Associates, LLPAl Rights Reserved. 49
    • Compensatory Stock OptionsEarly Exercise Considerations • Forfeit time value of option • Differential tax consequences favor early exercises) • Dividends on underlying stock • Cash flow situation • Price change expectations for underlying stock Need for diversification--concentrated portfolio • Better investment is available--exercise, sell and reinvest • Possible future change in tax rates • Employer stock ownership requirements© 2011 Keebler & Associates, LLPAl Rights Reserved. 50
    • To be added to our newsletter, please email robert.keebler@keeblerandassociates.com©2011 Keebler & Associates, LLPAll Rights Reserved. 51
    • CIRCULAR 230 DISCLOSURE Pursuant to the rules of professional conduct set forth in Circular 230, as promulgated by the United States Department of the Treasury, nothing contained in this communication was intended or written to be used by any taxpayer for the purpose of avoiding penalties that may be imposed on the taxpayer by the Internal Revenue Service, and it cannot be used by any taxpayer for such purpose. No one, without our express prior written permission, may use or refer to any tax advice in this communication in promoting, marketing, or recommending a partnership or other entity, investment plan or arrangement to any other party. For discussion purposes only. This work is intended to provide general information about the tax and other laws applicable to retirement benefits. The author, his firm or anyone forwarding or reproducing this work shall have neither liability nor responsibility to any person or entity with respect to any loss or damage caused, or alleged to be caused, directly or indirectly by the information contained in this work. This work does not represent tax, accounting, or legal advice. The individual taxpayer is advised to and should rely on their own advisors.©2011 Keebler & Associates, LLPAll Rights Reserved. 52