R11 Flashcards

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1
Q

Investment objectives

A

Reduce risk
Liquidity
Tax efficiency

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2
Q

Investment objective obstacles

A

Insider trading laws
Company restrictions
Wants to retain control
Asset has other uses

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3
Q

Considerations affecting all concentrated positions

A

Sale triggers tax bills
Asset illiquid
Transaction costs
Alternatives like hedging or borrowing

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4
Q

Constraints on dealing with concentration: Institutional and Capital market constraints

A

Margin lending rules
Regulations
Employer restrictions
Market limitations: needs liquidity, ability to borrow shares, brokers want observable trading history, instruments must exist

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5
Q

Psychological considerations: Emotional biases

A
  • Overconfidence/familiarity
  • Status quo
  • Naïve extrapolation of past results
  • Endowment effect
  • Loyalty effects
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6
Q

Psychological considerations: Cognitive biases

A
  • Conservatism
  • Confirmation
  • Illusion of control
  • Anchoring and adjustment
  • Availability heuristic
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7
Q

Goal-based planning: Personal risk bucket - goal and types of investments?

A

Goal: prevent big declines
Types: safe haven investments like home, money market, treasury bills

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8
Q

Goal-based planning: Market risk bucket - goal and types of investments?

A

Goal: Maintain current standard of living
Types: normal stocks/bonds

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9
Q

Goal-based planning: Aspirational risk bucket - goal and types of investments?

A

Goal: Grow wealth strongly
Types: high risk investments, concentrated positions

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10
Q

Primary capital: Definition + Source buckets

A

Def: provides lifetime spending needs
Buckets: Market/personal risk buckets

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11
Q

Surplus Capital: Definition + Source buckets

A

Def: excess capital above primary
Buckets: aspirational bucket

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12
Q

Monetize concentrated position: 5 questions that need to be answered

A
  1. Lifetime spending needs/desires after sale
  2. Primary/surplus capital requirements?
  3. Current value of concentrated position?
  4. Value of assets other than concentrated positions?
  5. Is value of concentrated position sufficient to meet primary/surplus capital need?
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13
Q

Wealth Transfer Strategies: 3 strategies

A
  • Gift to charity
  • Estate tax freeze
  • Combine limited partnership, gifting, valuation discount
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14
Q

Wealth Transfer Strategies: Gift to charity

A

-tax deduction for full value

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15
Q

Wealth Transfer Strategies: Estate tax freeze definition + example

A

Def: transfer future appreciation that does not get taxed
Ex: transfer junior equity to kids. current market value taxed, but not future appreciation.

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16
Q

Family Limited Partnership: Why does using this to transfer assets reduce taxes?

A

Value of limited partnership is less than sum of assets. Discount applied because of LP non-controlling stake and lack of marketability due to difficulty of selling

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17
Q

Equity monetization:

What are 4 basic types?

A
  1. Short sale against the box
  2. Total return equity swap
  3. Forward conversion with options
  4. Forward sale or single stock futures
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18
Q

Equity monetization:

explain a “short sale against the box”

A

short a security you already hold

19
Q

Equity monetization:

explain a “forward sale”

A

sell for delayed delivery

20
Q

Equity monetization:

explain a “forward conversion with options”

A

synthetic short forward position. Buy put, sell call at same strike. Riskless.

21
Q

Equity monetization:

explain a “Total return equity swap”

A

contract to pay return of stock (capital gains and dividends) in exchange for return on index, LIBOR, or other

22
Q

Two major hedging approaches

A
  1. Purchase a put

2. Cashless (zero premium) collar

23
Q

Cashless (zero-premium) collar

A

Buy a put slightly below market price, sell a call above market price to finance put premium

24
Q

Prepaid Variable Forward

A

Combines economics of a collar and a borrowing against underlying stock into a single instrument.

Get paid upfront and deliver shares (or cash) in the future based on terms of underlying collar.

25
Q

Choosing best hedging strategy: main considerations

A
  • minimal initial cost
  • max upside potential
  • max downside protection
  • minimum tax
  • other
26
Q

Tax Issue: mismatch in character

A

instrument hedged and tool used to do the hedge produce income and loss of different character.

E.g.: Stock options gains are “ordinary income”; hedging produces losses taxed at capital gains rate, but not deductible against ordinary income

27
Q

Tax optimization equity strategies: Index tracking with active tax management

A

make portfolio that tracks the market closely, not perfectly, and use opportunistic tax loss harvesting and other strategies to outperform on an after-tax basis

28
Q

Tax optimization equity strategies: completeness portfolio

A

Invest funds other than the concentrated stock position such that the combined portfolio is as diversified as possible. Whittle down concentrated piece over time.

29
Q

Tax considerations: what is a perfect hedge?

A

perfect hedge (hedge item and vehicle perfectly correlated; no systematic/non-systematic risk), if too perfect, could be equivalent to a sale, triggering tax due immediately

30
Q

Tax considerations: what is a cross hedge and what is a downside of using it?

A

If instruments to hedge asset directly do not exist, hedge a substitute asset with high correlation with primary asset.

Downside: don’t eliminate company-specific (non-systematic) risk

31
Q

Tax considerations: what is an exchange fund? How long must partner remain in fund?

A

An investment fund where partners each contribute their concentrated positions and gain pro-rata share of total fund.

How long: must remain in fund 7 years

32
Q

Managing risk of privately held business: what are three considerations?

A
  • owner psychologically attached
  • Owner has financial reasons to maintain control
  • Complexity in determining exit strategy and value
33
Q

Business monetization: Strategic buyer

A

Pay more than financial buyers, because long term view.

Usually very active.

34
Q

Business monetization: Financial buyer

A

typically invest in mature/stable businesses.

Don’t pay as much as strategic buyer

35
Q

Business monetization: Recapitalization

A

Company issues debt to finance purchase of owner’s shares

36
Q

Business monetization: Management Buy Out

A

group of employees buy the business.

Most of the time owners acts as creditor for small cash component and large promissory note, because employees cannot raise enough cash.

37
Q

Business monetization: Divestiture

A

sell some assets

38
Q

Business monetization: Sale or gift to family member

A

self explanatory

39
Q

Business monetization: Line of credit secured by company shares

A

personal loan secured by shares.

40
Q

Business monetization: Employee stock ownership plan

A

An ESOP. Tax advantaged for Subchapter C companies.

41
Q

Real-estate monetization: Mortgage financing

A

Get a mortgage where payments equal to rent (if income generating property)

Non-recourse loan means could only go after property in case of default

42
Q

Real-estate monetization: Sale-leaseback

A

sell property for cash and lease back to retain use

43
Q

Real-estate monetization: Donor-advised fund or charitable trust

A

give asset to charity or fund set up for charitable gift. Full tax deduction on gift.