Brian Sheahen
House Ways and Means Proposed Tax Reform

On Monday September 13, the House Ways and Means introduced proposed tax changes for debate this week in an initial bill. The tax changes would be significant for many taxpayers and is intended to finance a broader $3.5 Trillion domestic investment plan. The changes proposed in the House bill will almost certainly evolve and deviate to a degree from how they are originally drafted, if it even ever becomes law. At the moment, these are purely provisions as part of the House Ways and Means initial bill proposal and should not be relied on as specific tax law or guidance.

House Ways and Means Proposed Tax Reform
Financial Planning, Executive Compensation, Equity Compensation Plans, Investments, Personal Finance, Trust & Estate, Wealth Transfer
Brian Sheahen
What Should I Do With My Concentrated Stock ...

Many of our clients first come to us with concentrated stock positions that they have obtained either through their employment, equity compensation, sale of a business, a well-timed trade, from family, or through some other means. They all share a common theme of idiosyncratic (non-systematic) risk which is inherent in owning a concentrated position. The specific risks however, and potential rewards, can be unique to each situation. They also all have unique wealth and tax considerations that need to be independently addressed. The facts of each unique situation, along with the stock owner’s financial goals and profile will guide the appropriate course of action in response to the common question of “What next?”.

What Should I Do With My Concentrated Stock Position?
Trust & Estate, Wealth Transfer
Brian Sheahen
GRATitude

The Grantor Retained Annuity Trust (GRAT) is a classic wealth transfer planning tool, but in order to properly implement this technique the grantor must feel compelled to make the transfer.  In families with means that may look to implement this technique it can be helpful to begin having conversations about the family wealth well in advance of actually implementing such a strategy.  Appropriately involving family can help create a sense of awareness, responsibility and eventually gratitude for the wealth that could be coming their way. 

GRATitude
Tax, Investments
Brian Sheahen
Amid Market Volatility - Beware of Wash Sales

Volatility is the price investors must pay in the search for higher future returns in capital markets. To many savvy investors with taxable investment accounts, the declines we saw in February and March (and quite possibly going forward still for some time) may have actually presented opportunities. One such opportunity has been to capture valuable tax losses from their investments. However, these same investors need to be especially careful to navigate the wash sale rules of the Internal Revenue Code (IRC) Section 1091, or their tax loss strategy may have all been for nothing.

Amid Market Volatility - Beware of Wash Sales
Behavioral Finance, Investments, Risk Management
Brian Sheahen
Diversification - Winning While Losing

COVID-19 and the resulting global pandemic has tested our global community, economy and markets. Investors with a diversified portfolio may have faced the following emotions of “I lost money” as the market first fell, followed by “I didn’t make as much” as the market has recently recovered (but for how long?). Yet, over a 20-year period, a diversified portfolio has still provided a higher total return, while assuming much less risk than the S&P 500. In the end, diversification wins, even when it feels like losing.

Diversification - Winning While Losing

Personal Finance

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What Should I Do With My Concentrated Stock Position?

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What Should I Do With My Concentrated Stock Position?

Many of our clients first come to us with concentrated stock positions that they have obtained either through their employment, equity compensation, sale of a business, a well-timed trade, from family, or through some other means. They all share a common theme of idiosyncratic (non-systematic) risk which is inherent in owning a concentrated position. The specific risks however, and potential rewards, can be unique to each situation. They also all have unique wealth and tax considerations that need to be independently addressed. The facts of each unique situation, along with the stock owner’s financial goals and profile will guide the appropriate course of action in response to the common question of “What next?”.

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When Does an Intra-Family Loan Make Sense?

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When Does an Intra-Family Loan Make Sense?

A low-yield and interest rate environment can be a difficult time for investors searching for total return from their investments. At the same time, any savvy investor should be looking for opportunities from a total wealth-planning perspective. As a result, with very low-interest rates, there are many family wealth transfers and planning opportunities that may be appealing. Intra-family loans in particular are appealing now while rates are at the lowest they have ever been.

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10 Planning Strategies for Year-End

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10 Planning Strategies for Year-End

As we approach the end of 2019, individuals and businesses may have unique opportunities to creatively boost savings, make investments, transfer wealth, implement certain tax strategies, and more.  Proper planning and implementation now, with over two months remaining in 2019, can save a lot of headaches and rushed decision-making during the final days of December.

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Two-Step Roth IRA Conversions & Considerations

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Two-Step Roth IRA Conversions & Considerations

High-income taxpayers face restrictions on their ability to contribute to a Roth IRA.  Through proper planning, however, Traditional IRA assets may be efficiently converted into Roth IRA assets at no tax-cost. If managed appropriately, a taxpayer can effectively circumvent the income limitations by engaging in a two-step contribution and conversion process (Two-Step Roth IRA), also commonly referred to as a “Backdoor” Roth contribution. Methodically engaging in this strategy may generate significant tax savings over time.