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How financial advisors can wind down stock concentrations

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Concentrated stock holdings carry higher risks of volatility and — once sold in order to diversify investment portfolios — steep tax hits for clients. 

Behavioral biases often linked to one stock due to a client’s long-term association with a company through their employment, early investment or another factor are common, according to experts. They represent “a tricky conversation for advisors, but probably one they’re pretty commonly having,” said Jeremy Milleson, a director of investment strategy with Morgan Stanley- and Eaton Vance-owned asset manager Parametric Portfolio Associates

The discussion can begin with an acknowledgement that the large holding is “a good problem to have,” and also begs the question of “how do we more tax-efficiently potentially reduce that concentration” without receiving the influx of taxable capital gains, Milleson said in an interview.

“For some clients, maybe the majority of their wealth might be in an individual stock,” he said. “For a lot of clients, there is that emotional tie.”

READ MORE: Excluding capital gains of $10M — or more — from taxes with QSBS

They probably aren’t holding onto notorious examples of companies that experienced steep declines in value such as Enron, Bear Stearns or Sears, but any stock will sustain some losses over time. In five-year rolling periods spanning from 2000 to 2021, the value of every single stock in the S&P 500 dropped by at least 20%; and 63% of them tumbled by 40% or more, according to a blog post by Milleson last month

Over a longer period between 1987 and 2023, tracking a wider swath of stocks as a benchmark for the market in the Russell 3000, just 34% of the individual companies outperformed the index, 27% underperformed but still reaped positive returns and 39% lost value, data from BlackRock showed.

“While investors may be tempted to hold a concentrated stock position in the hope of greater profit, they may fail to understand that they are not being compensated for taking this risk,” according to a study by the research arm of Baird Private Wealth Management. “In theory, stocks are riskier investments that should provide higher returns than less risky investments like Treasury securities. However, the risk/reward premium turns against the investor when too few stocks are owned, and especially when the investor holds a single or large, dominant position. Returns become too reliant on the fortunes of one company (exposing the investor to significant company-specific fundamental risks) and to a single industry (exposing the investor to sector-specific risks). As a result, it is clear that investors should choose to diversify a concentrated stock position whenever possible.”

Clients’ refusal to do so may stem from more than a half dozen forms of behavioral biases, according to an analysis earlier this year in Financial Advisor magazine by Larry Swedroe, the head of financial and economic research for St. Louis-based registered investment advisory firm Buckingham Wealth Partners. For example, heavy concentrations in one stock can trigger commitment and confirmation bias, in which investors believe they would be disloyal to sell and tune out evidence that holding on to the same position isn’t their best course, he noted. Taxes can play into their reasons for staying the course as well.

“A major issue that often leads investors to fail to diversify their concentrated position is the desire to avoid paying large capital gains taxes,” Swedroe wrote. “Before addressing strategies to avoid or at least minimize that problem, I remind investors that there is only one thing worse than having to pay taxes — not having to pay taxes (as happened to those with concentrated positions in Enron, among many others).”

READ MORE: Convincing clients to let go of huge holdings

As an antidote for the possible tax hit, Swedroe mentioned an alternative investment in the form of a leveraged strategy known as variable prepaid forwards, as well as charitable donations or moving the shares into a diversified basket of securities called an exchange fund. However, the latter choice defers the tax hit rather than eliminating it outright, Milleson noted in the blog post. A custom diversification strategy over time through direct indexing could produce losses for offsetting capital gains as well, he wrote.

“Building a customized, staged diversification plan can help spread the cost of diversification over a number of years or make sure the cost stays within a certain gain budget — allowing for greater control of the tax bill and the degree of diversification,” Milleson wrote. “This plan can be modified at any time depending on changes in the market or client needs. Using leverage can help increase the losses generated in a direct indexing account and accelerate the diversification.”

If the client must hold onto the shares for any reason, an options-based covered call strategy could cut down on their concentration and boost their earnings over time, he added.

With “a lot of different solutions” for concentrated stock holdings and the accompanying tax questions, advisors should take an educational approach in guiding clients through the process, Milleson said. They don’t need to wind down all of their holdings in the stock at once, either. 

As advisors inform the customers of the risks of not diversifying, they can “highlight that while being sensitive to the client who probably takes great pride in having built their wealth from this position,” he said. “It’s worth having those conversations, understanding that maybe it’s one of those solutions or a combination of those solutions that’s the best fit for the client.”

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Accounting

Continuous Auditing Transforms Corporate ERPs

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continuous auditing transforms corporate erps

As corporate accounting departments cross the threshold into late July 2026, the adoption of continuous, automated auditing systems has reached a definitive turning point. Driven by advances in artificial intelligence and deep integration with modern Enterprise Resource Planning (ERP) platforms, leading finance organizations are moving away from traditional, periodic post-hoc audits in favor of real-time, 100% transactional verification. This technological transition is redefining internal control environments, reducing compliance costs, and eliminating the structural delays inherent in legacy quarterly closing processes.

Unlike traditional auditing frameworks that rely on statistical sampling—a process that inevitably leaves operational blind spots—continuous auditing software monitors operational data feeds continuously. Every purchase order, electronic invoice, payroll disbursement, and cross-border wire transfer is automatically cross-referenced against established corporate governance parameters, regulatory tax schedules, and anti-fraud algorithms in real time. Anomalies or unauthorized ledger entries are flagged instantly, allowing internal audit teams to investigate and remediate compliance gaps immediately rather than months after the close of a financial period.

The implications for executive financial management are far-reaching. By embedding continuous verification directly into daily transaction workflows, chief financial officers gain uninterrupted visibility into the organization’s true financial standing. Real-time balance sheet auditing eliminates the severe operational bottlenecks associated with month-end and quarter-end financial reconciliations, freeing accounting professionals to focus on strategic financial modeling, tax planning, and capital allocation rather than manual data entry and spreadsheet consolidation.

However, implementing continuous auditing requires accounting leadership to invest heavily in data governance and technical upskilling. Internal audit teams must evolve from manual ledger reviewers into system architects capable of auditing complex algorithms and validating automated data pipelines. Accounting firms and corporate controllers that master continuous auditing will establish a resilient compliance framework capable of meeting stringent international regulatory standards with total transparency.

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Accounting

U.S. Imposes New 50% Tariffs on Canadian Imports Under Rare Legal Provision

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U.S. Imposes New 50% Tariffs on Canadian Imports Under Rare Legal Provision

WASHINGTON — In a major escalation of cross-border trade friction, U.S. President Donald Trump has signed executive orders imposing new 50% tariffs on a wide selection of Canadian exports, citing discriminatory practices by Ottawa targeting American auto, dairy, and beverage industries.

The new duties, announced Monday, will take effect in 30 days. They target a broad spectrum of consumer and industrial goods—ranging from wine, liquor, and milk products to commercial cement, furniture, clothing, and hockey equipment.

Untested Legal Mechanism

To enact the sweeping measures, the administration invoked Section 338 of the Tariff Act of 1930—a rarely used legal provision allowing the executive branch to levy additional tariffs of up to 50% on foreign nations deemed to discriminate against U.S. commerce.

White House officials noted that Section 338 addresses trade discrimination rather than national security or economic emergencies. The move comes months after prior global emergency tariffs faced legal challenges in domestic courts, signaling Washington’s pivot toward alternate statutory authorities to maintain import duties.

Senior administration officials briefed reporters that the measure directly responds to Canadian provincial bans on U.S. alcohol, restrictions on American vehicle exports, and import quota disparities affecting U.S. dairy and cheese producers relative to third-party trading partners.

“While the administration continues to secure reciprocal trade agreements globally, Canada retaliated against efforts to protect domestic industry,” U.S. Trade Representative Jamieson Greer stated.

USMCA Impact and Carve-Outs

Significantly, the newly ordered 50% duties will apply to designated items even if they otherwise comply with the United States-Mexico-Canada Agreement (USMCA).

However, the administration confirmed key targeted exemptions:

  • Energy products (including oil and natural gas)
  • Potash and critical minerals
  • Fish and seafood
  • Goods already governed by sector-specific duties (such as existing steel and aluminum tariffs)

Administration representatives emphasized that the tariffs do not stem from recent disputes concerning drifting Canadian wildfire smoke, noting that policy options regarding environmental spillover remain under separate review.

Canadian Response and Market Reaction

Following the White House announcement, the Canadian dollar experienced a sharp decline against the U.S. dollar, falling approximately 0.4% during evening trading.

Canadian Prime Minister Mark Carney issued a statement emphasizing that Canada’s earlier counter-duties had merely matched previous U.S. trade actions. “Canada stands ready to engage intensively to address outstanding issues with the U.S. to the mutual benefit of our citizens,” Carney stated, pointing to detailed proposals Ottawa submitted to modernize the USMCA framework.

Ontario Premier Doug Ford took a firmer stance, urging a “dollar-for-dollar” reciprocal response if the measures go into effect on August 19.

With a 30-day implementation window before the duties officially lock in, industry associations and trade groups on both sides of the border are calling for urgent bilateral negotiations to avert further supply chain disruption across North America.

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Accounting

Automated Continuous Auditing: Transforming Compliance and Real-Time Financial Oversight

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Transforming Compliance and Real-Time Financial Oversight

The traditional accounting paradigm—defined by periodic monthly closures and post-hoc annual audits—is rapidly giving way to continuous, automated financial oversight. As of July 2026, forward-thinking accounting practices and multinational corporate finance departments are leveraging continuous auditing systems powered by advanced machine learning models. These systems monitor operational transactions in real time, shifting audit methodologies from sample-based post-analysis to absolute, 100% transaction-level verification.

The operational advantages of continuous auditing are transformative. Standard auditing procedures historically relied on statistical sampling, which, despite rigorous methodology, inherently left gaps where anomalies or fraudulent transactions could go undetected for months. Modern continuous auditing platforms integrate directly with enterprise resource planning (ERP) databases, instantly cross-referencing purchase orders, invoices, bank feeds, and tax records. Any deviation from established control parameters or unusual transaction behavior triggers immediate flags for internal audit teams, dramatically reducing detection lag from quarters to seconds.

Beyond fraud prevention, continuous auditing fundamentally alters internal reporting and decision-making. Executive leadership no longer has to wait weeks after the close of a quarter to evaluate precise financial standing; real-time verified ledger data provides an uninterrupted view of operating margins, tax liabilities, and cash flow dynamics. This real-time visibility enables corporate controllers to adjust capital allocation strategies dynamically, mitigating liquidity constraints and capitalizing on emerging commercial opportunities far more efficiently than competitors bound to legacy reporting cycles.

However, implementing continuous auditing requires accounting professionals to acquire new analytical capabilities. The role of the auditor is evolving from manual data reconciliation toward system validation, algorithmic model governance, and strategic risk interpretation. Accounting firms and corporate finance departments must invest in continuous technical education, ensuring that audit staff possess the data engineering skills necessary to design, maintain, and evaluate complex automated compliance systems.

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