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On July 4, President Donald Trump signed a budget reconciliation bill entitled the “One Big, Beautiful Bill Act” (the Act). The Act extends the tax cuts that were enacted as part of the Tax Cuts and Jobs Act of 2017, adds a...more
At the beginning of this series, I mentioned briefly that taxpayers can use tax-loss harvesting approaches in tandem with a number of investment strategies, which we will go into in more detail in Part III. Many of these...more
What is tax-loss harvesting? “Tax-loss harvesting,” in its simplest form, is the sale of a capital asset at a loss to “mop up” tax that would otherwise be due on capital gain from the sale of another capital asset. Capital...more
The recently signed One Big Beautiful Bill Act (OBBBA) implements significant changes under Section 1202 of the Internal Revenue Code of 1986 (Code), applicable to qualified small business stock (QSBS) issued on or after July...more
As investors increasingly leverage Section 1031 exchanges to defer capital gains taxes, nuanced scenarios involving interest income on exchange proceeds require careful analysis. A critical but often overlooked aspect arises...more
The intersection of real estate transactions and tax strategy has long been a focal point for investors seeking to optimize returns while minimizing liabilities. Two powerful tools in this arena – the Membership Interest...more
The “qualified small business stock” (QSBS) tax exemption under Section 1202 allows non-corporate founders and investors in certain emerging growth companies to potentially exclude up to 100 percent of the U.S. federal...more
Internal Revenue Code (IRC) Section 1202 offers a significant tax incentive for investors in qualified small business stock (QSBS). This provision allows eligible shareholders to exclude up to 100% of capital gains realized...more
Founders, entrepreneurs, venture capitalists and other investors (all of which are collectively referred to herein as “investors”) should be familiar with Internal Revenue Code Section 1202, a valuable provision that...more
The secondary market for limited partner interests in venture capital funds has witnessed robust growth in recent years as an increasing number of existing venture fund investors seek an early exit from their positions for...more
Which transactions qualify as section 988 transactions? In section 988 transactions, the taxpayer makes payments or receipts denominated in or determined by reference to one or more nonfunctional currency. ...more
This is The End- I have dreaded the year end for as long as I can remember. As a teenager and then as a young adult I associated the final quarter of the year, and especially the period beginning on Thanksgiving and...more
In the event of an M&A transaction, many stockholders plan to take advantage of the exclusion from federal taxable income of gain realized from the sale or exchange of “qualified small business stock” (QSB stock). Section...more
At war with Russia in eastern Europe, a nascent competing world order, mass shootings and bank failures at home, questionable audit practices by the Big 4 . . . everywhere, debt ceilings and the risk of default, inflation,...more
When it comes to the taxation of stock options, the Internal Revenue Code (Code) does not define capital assets. Rather, it identifies those assets that are not capital assets. ...more
Since coming into effect in January 2018, Subchapter Z of the US Tax Code—also known as the opportunity zone provisions—has enabled investors to pour billions of dollars into a broad array of businesses, from real estate...more
In this second blog post on the House Ways and Means Tax proposals, we address the proposed changes that will affect the taxation of trusts, estates, and retirement plans. As we discussed, on September 13, 2021, the...more
With the prospect of an increase in capital gain income tax rates looming on the horizon, what could be more welcome than an exclusion of 100% of gain from income? That is exactly what Section 1202 of the Internal Revenue...more
The IRS has several tools in its arsenal to encourage compliance and audit and enforce those it believes are failing to comply. One of the most powerful tools is the John Doe summons. A regular IRS summons seeks information...more
The IRS issued Notice 2020-39 on June 5, 2020 in response to the COVID-19 pandemic, which extended several deadlines applicable to Opportunity Zone investments. •First, investors get more time to invest eligible gains into a...more
The IRS recently issued additional Opportunity Zone-related guidance, Notice 2020-39, that grants extension relief with respect to five specific time-sensitive actions. Among other things, Notice 2020-39 (i) allows certain...more
On April 10, 2020, the Internal Revenue Service (the “IRS”) issued Revenue Procedure 2020-22 (the “Revenue Procedure”), which (1) permits an “electing real property trade or business” that elected not to be subject to the...more
Opportunity Zone (or “OZ”) investment was hailed in 2018 and 2019 as the hottest and most innovative way of attracting significant private capital to distressed communities in the United States and its territories by offering...more
As we enjoy the Silicon Slopes Tech Summit 2020, it has been great to catch up with executives, investors, and entrepreneurs working to build the next technology ideas into successful companies. It is interesting to think...more