Clients think that because they are retired, the way to get income is through dividends and interest. Such thinking arises from what my partner Deena calls the “paycheck syndrome,” and it is nonsense. ...
... if clients depend on income largely from their bond portfolios, then when interest rates go up, they feel rich. But what is actually happening to the value of their portfolio? It is going down. When interest rates go down, they feel poor, but the portfolio value is going up. The strategy runs counter to financial reality. ...
People need real income. They need real cash flow, not nominal cash flow, and they do not get that real cash flow from an income portfolio.

[T]here is nothing new about it. ... I think it has been misused and overused. ...
I see several problems ... First, the increased number of guesses that Monte Carlo allows does not mean more accuracy. Second, Monte Carlo devalues the goal-setting process. Third, Monte Carlo probabilities are all or nothing. If Monte Carlo says I have a 70 percent chance of success, what does the remaining 30 percent mean? Starvation? Finally, Monte Carlo offers no insight into the unexpected, such as a Katrina event or the subprime crisis.

The first bucket strategy was developed by financial planning pioneer Harold Evensky in 1985. This was a two-bucket approach with a cash bucket holding five years of retirement spending, and a longer-term investment bucket consisting mostly of stocks. When the stock market performed poorly, withdrawals were taken from the cash account to avoid selling stocks in a down market, and when the stock market did well withdrawals were taken from the investment bucket, and investments from this bucket were also sold to replenish cash.

E&K Cash Flow Strategy. Sometime in the early 1980s, at Evensky and Katz we developed the E&K cash flow strategy that we continue to use today. It allows us to break the paycheck syndrome -The traditional withdrawal strategy for retirement is the income portfolio. It is a deeply flawed strategy, and any financial adviser who recommends income portfolios should cease and desist. Clients think that because they are retired, the way to get income is through dividends and interest. Such thinking arises from what my partner Deena calls the “paycheck syndrome,” by providing clients with a regular cash flow that they can depend on. Typically, it also includes an inflation adjustment because pay typically goes up with inflation.
To implement the cash flow strategy, we bifurcate the portfolio into two components—the cash flow reserve and the investment portfolio. The cash flow reserve portfolio is made up of two parts: two years’ worth of cash flow and any amounts needed for lump-sum expenses—a wedding, a new car, for instance—over the next five years. We base this amount on our five-year planning model. We do not believe in investing in stocks or bonds unless we have a five-year window in which to decide when to sell. We thereby mitigate the timing risk because we have control over the timing.

Thiel’s unusual stock purchase risked running afoul of rules designed to prevent IRAs from becoming illegal tax shelters. Investors aren’t allowed to buy assets for less than their true value through an IRA. The practice is sometimes known as “stuffing” because it gets around the strict limits imposed by Congress on how much money can be put in a Roth.
PayPal later disclosed ... in an SEC filing ... that Thiel’s founders’ shares were among those the company sold to employees at “below fair value.”
Victor Fleischer, a tax law professor at the University of California [asserted that] buying startup shares at a discounted $0.001 price with a Roth ... would be indefensible.

The problem is no one in Congress thought about putting an upper limit on Roth IRA withdrawals when they wrote the law

When someone inherits property and investments, the IRS resets the market value of these assets to their value on the date of the original owner’s death. Then, when the heir sells these assets, capital gains taxes are applied based on this reset value. The result is a situation – often considered a tax loophole – that allows investors to pass assets to their heirs virtually tax-free.

If President Biden gets his way, many wealthy Americans will no longer be able to pass stocks, real estate, and other capital assets to their heirs when they die without paying capital gains tax. He wants to do this by changing the tax rules that allow a "step up" in basis on inherited property. This proposal, along with others designed to increase taxes on the wealthy, is included in Biden's recently released American Families Plan – a $1.8 trillion package that includes spending on childcare and education, guaranteed paid family and medical leave, tax breaks for lower- and middle-income Americans, and more.

Was looking for a HY bond fund that had held up decently ("defensive?") in 1Q 2020. Found EIXIX with a 5.5% SEC Yield. $2,500 min at VGD (TF). May be my newest addition.

Normally investing at least 80% of the fund’s assets in securities included in the Fidelity Clean Energy Index℠ and in depositary receipts representing securities included in the index. The Fidelity Clean Energy Index℠ is designed to reflect the performance of a global universe of companies across the market capitalization spectrum that distribute, produce or provide technology or equipment to support the production of energy from solar, wind, hydrogen and other renewable sources.

SEC filings ... show that he bought his first slice of the company in January 1999. Thiel paid $0.001 per share — yes, just a tenth of a penny — for 1.7 million shares. At that price, he was able to buy a large stake for just $1,700.

Mr. Thiel purchased his founders’ shares in PayPal through his Roth IRA during PayPal’s formation.