What Changed and What Didn’t On December 18, 2025, President Trump signed an executive order directing the Attorney General to expedite completion of the federal rulemaking process to move cannabis from Schedule I to Schedule III. The order follows a 2023 recommendation from the Department of Health and Human Services (HHS), which found over 30,000 […]
The Permanent Challenge of 280E Section 280E can create effective tax rates exceeding 70% for cannabis businesses, fundamentally altering the economics of an otherwise profitable industry. Originally enacted in 1982 after Edmondson v. Commissioner allowed a cocaine trafficker to deduct business expenses, the statute now applies to every state-legal cannabis operation. IRS audit data has […]
Equity compensation represents one of the most overlooked value levers in company building. For growth-stage companies with multi-state teams and approaching liquidity events, the difference between strategic design and template documentation can mean millions in preserved net operating losses (NOLs) at exit, 30% more value delivered to key employees, and months saved during diligence. Quick […]
Life sciences companies navigate a unique gauntlet. Programs pivot, trials fail, and financing windows slam shut without warning. Yet tax decisions made in the scramble of formation echo through every funding round until they crystallize at exit, for better or worse. The One Big Beautiful Bill Act didn’t just adjust rates. It rewired fundamental incentives […]
QSBS in the Post-OBBBA Environment: Understanding the Enhanced Benefits Most startup exits fall squarely in QSBS territory, yet founders routinely forfeit millions in tax savings through early missteps. The difference between proper QSBS planning and hoping for the best? Often $3-5 million on a typical exit. The Qualified Small Business Stock exclusion can now shield […]
For growing companies operating across state lines, multistate tax compliance has always been complex. But 2025 marks a fundamental shift in how states approach enforcement—one that many CFOs and tax directors are discovering too late. While most focus on obvious triggers like economic nexus thresholds and sales tax registration, the often-overlooked coordination between income and […]
For multinational businesses navigating global expansion, the OBBBA introduces changes that go beyond typical rate adjustments. It rewrites fundamental assumptions about where to locate operations, how to structure intellectual property, and when to recognize cross-border income. The Act even renames key international provisions to reflect their evolved nature: Global Intangible Low-Taxed Income (GILTI) becomes “Net […]
P.L. 86-272: A Shrinking Shield In 1959, Congress enacted Public Law 86-272 in response to state efforts to tax out-of-state businesses based on minimal connections. The law established a critical safe harbor: states cannot impose net income taxes on businesses whose only in-state activities involve soliciting orders for tangible personal property, provided those orders are approved […]
Under the Tax Cuts and Jobs Act (TCJA), deductions for investment-related expenses under Section 212 were severely limited, effectively eliminating deductibility for family offices that operate as passive investment vehicles. This change has persisted, and the OBBBA permanently extends the suspension of miscellaneous itemized deductions under Section 67(g), making the Section 212 ban permanent. That […]
Private equity funds operate in an increasingly complex tax environment where structural missteps can invalidate allocation models or trigger unexpected tax and reporting obligations. As investor profiles and investment strategies diversify, the intersection of partnership tax rules, international compliance regimes, and economic modeling presents challenges that even experienced sponsors can overlook. These errors, particularly in […]
After months of committee rewrites and inter‑chamber brinkmanship, late-stage conference trimming, and vigorous floor debate, the One Big Beautiful Bill Act (OBBB) crossed the finish line on Independence Day 2025 with the President’s signature. The measure delivers the most consequential business‑tax reset since the Tax Cuts and Jobs Act of 2017. It restores immediate deductions, […]
The rise of decentralized technologies has outpaced tax authorities’ ability to define, regulate, or even classify the activities that drive the Web3 economy. What began as a debate over whether cryptocurrency is property or currency has evolved into a far broader challenge: how to apply legacy tax rules to entirely new modes of economic activity. […]
Clearing federal hurdles doesn’t stop state tax auditors; foreign groups learn this only after a surprise assessment. When multinational businesses enter the U.S. market, they often begin by evaluating federal tax rules: whether the foreign entity is engaged in a U.S. trade-or-business, whether treaty protections apply, and how income is characterized for U.S. purposes. These […]
Treaty planning is one of several influential factors that can shape the economics of cross-border M&A transactions. When built into the deal strategy from the outset, it can reduce withholding taxes on future cash flows, or even eliminate them entirely. When overlooked or treated as a post-closing task, it can lead to suboptimal structures and […]
In U.S. tax compliance, international reporting failures occupy a unique, and often underestimated, category of risk. While domestic errors can carry modest penalties and clear resolution pathways, international information reporting missteps can often result in penalties starting at $10,000 or more per form, per year. Those penalties can ratchet up to $50,000 to $100,000, a […]
For technology companies, global expansion presents unique challenges. While digital businesses can scale across borders with ease, doing so inevitably triggers complex tax obligations. The intersection of entity structure, revenue characterization, and intellectual property (IP) ownership shapes decisions that drive global effective tax rates and compliance burdens. The inherently borderless nature of digital technology can […]
The House-passed version of H.R. 1, dubbed the “One Big Beautiful Bill Act” (OBBBA), includes important revisions to business tax policy, from more permissive R&D expensing to aggressive new international measures. But as the bill moves to the Senate, its fate remains far from settled. With an aspirational goal of passage by July 4, 2025, […]
State tax residency determination represents a significant planning area for high-net-worth individuals, particularly those with substantial income events or those who spend time in several jurisdictions. As states face increasing budget pressures, tax authorities across the nation continue to develop increasingly sophisticated approaches to capturing revenue from residents and former residents alike. States including California […]
Restructuring your supply chain isn’t just about operations—it’s about aligning trade, tax, and pricing strategies to reduce tariffs and unlock long-term financial efficiency.
State tax issues often surface late in the M&A process—and can lead to complex renegotiations. One of the most common culprits? An overlooked multistate tax obligation.
As a founder, you’ve poured years of your life into building your company. The sleepless nights, the pivots, the hiring decisions, the product launches—all leading to this moment…
