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Scaramucci struggles to spin a Trump tax break into profit for clients

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Anthony Scaramucci is struggling to spin one of President Donald Trump’s big tax breaks into a profit for his wealthy clients. Yet “the Mooch,” as he’s known on Wall Street, keeps getting paid his fees.

The hedge fund manager known for his 10-day stint as White House communications director in 2017 promised wealthy investors that he could help them take advantage of Trump’s signature program for spurring projects in low-income communities, dubbed opportunity zones. 

His list of ideas included a luxury hotel in Oakland, California, a warehouse in Savannah, Georgia, and middle-income housing. 

But key targets that Scaramucci laid out in 2018 interviews haven’t been realized. Instead of raising $3 billion for his SkyBridge Opportunity Zone Real Estate Investment Trust, he amassed less than $50 million and made a single investment: a Virgin Hotels property in the Warehouse District of New Orleans. 

The vehicle has yet to distribute payouts to REIT shareholders — let alone generate the 8% to 10% annualized returns before tax benefits that he suggested would be possible over the fund’s lifetime.

SkyBridge Capital, meanwhile, continues getting paid 1.75% of the fund’s net asset value, which was $43.2 million at the end of 2024.

Executives for the hedge fund firm declined to comment.

Trump’s One Big Beautiful Bill Act recently made opportunity zones permanent, setting up another wave of investment funds that could start taking shape in January 2027. The SkyBridge experience may serve as a cautionary tale to investors: Tax benefits only matter if you make money.

Trump championed these zones in his first term as a way to drive private capital to long-neglected parts of the U.S. Investments in the zones topped more than $80 billion, according to a report from the Joint Committee on Taxation based on returns filed for 2019 through 2022.

Boosters say the zone investments have helped build affordable housing and created jobs and new businesses. 

Yet these dollars have not been evenly spread, with much of the money flowing to urban and suburban areas and wealthier states such as Florida and New York, the Joint Committee found. Louisiana, home to the SkyBridge fund’s hotel, received less than $500 million, or $106 per person, one of the lowest amounts across the U.S., even though it’s among the poorest states.

Most academic studies of the program show that, at least in its first few years, the opportunity zones had little or no economic impact, according to the Joint Committee’s report. 

Investors, though, potentially win big. If they take profits from stocks, bonds or other investments and put them into an opportunity zone fund, they’ll reduce their capital gains on the initial sale and defer its payment until 2026. If they keep the fund for at least a decade, they’ll pay no capital gains on its returns.

So far, it looks like SkyBridge clients could miss out on that tax-free benefit. From the firm’s initial money raise in December 2018 through the end of last year, it has lost 1.4%, according to investors. Those who got into the fund the following year are down 5.6%, the investors said. 

The New Orleans hotel is a sleek building with a rooftop pool, nestled in a neighborhood full of galleries, restaurants and shops. It gets 4.7 stars out of 5 on TripAdvisor. Even so, some investors say they doubt the value of the hotel will rise sharply in coming years. It makes money, but its net operating income has been fairly stable — between $4.7 million and $5 million — in its first three full years of operation, according to investors. 

The lack of growth is in line with other hotels in New Orleans, where revenue per available room was 11% lower in July than it was three years earlier, according to data from STR.

While data on opportunity zone investment returns more broadly is scant, the pandemic hit the real estate market hard, meaning that some funds have had difficulty making money. A pool that backed downtown office buildings, for example, is probably underwater, while one that focused on multi-family units in the Sun Belt would more likely be profitable.

“The program has been disappointing,” SkyBridge President Brett Messing said in a March 2020 interview with Yahoo Finance, pointing to the 10-year holding period and inherent risks of real estate development. “We’ve been modestly successful, but it’s been tougher to execute than we expected.”

No-win situation

Because of strict loan covenants, the hotel’s lender sweeps some profits into an escrow account, meaning investors in the REIT haven’t received any cash distributions. The REIT itself has run out of money, so in July it sold new shares to existing holders. With the proceeds, it can continue to pay fees to SkyBridge.

The fund offered more than $6 million of shares to existing holders at an 80% discount, amounting to 15% of shareholder equity, according to investors and a regulatory filing.  

That move put clients in what some saw as a no-win situation. If they chose not to participate, they’d dilute their holdings. If they chose to buy, they’d get an immediate return on paper — but could risk having to pay taxes on that gain unless the fund owns the hotel for 10 more years. SkyBridge told some investors it expects to get out before then.    

SkyBridge also charges investors a collective $150,000 a year for proxy fees and an annual meeting on video conference. 

During last year’s shareholder call, Messing told clients he couldn’t answer their questions about the fund because he was sitting in his car in Los Angeles. Anyone wanting more information could set up a call in the coming weeks, he said.

When investors groused about the lack of immediate responsiveness, he said he was adjourning the meeting, which caused even more complaints. Messing retorted with a threat: Keep up the insults, and we won’t talk to you at all. 

On this year’s call held in May, SkyBridge put its clients on mute.  

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Accounting

AI-Driven Automation and Continuous Accounting Frameworks

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The accounting profession is undergoing a fundamental structural transition as enterprise finance departments shift from periodic month-end closes toward automated continuous accounting models. By integrating specialized machine learning algorithms directly into enterprise resource planning (ERP) platforms, chief accounting officers are transforming financial reporting from a retrospective exercise into a real-time operational asset.

The Shift from Periodic Close to Continuous Financial Reporting
Traditional accounting workflows heavily relied on manual data reconciliation, spreadsheet calculations, and multi-week closing cycles at the end of each fiscal period. In contrast, continuous accounting frameworks utilize automated software agents to process, validate, and post transactional data in real time as business activities occur.

Automated bank reconciliation tools cross-reference incoming bank feeds, invoice records, and purchase orders automatically. By resolving transactional variances instantly throughout the month, corporate accounting teams eliminate the traditional workload spikes associated with quarterly and annual closes.

Machine Learning in Audit Trails and Anomaly Detection
Advanced natural language processing (NLP) and machine learning tools are redefining internal audit and financial control environments. Automated systems analyze 100% of general ledger entries, identifying anomalous transactions, duplicate payments, and unauthorized journal entries in real time.

Rather than relying on random statistical sampling, corporate internal auditors can focus their attention on high-risk flags automatically surfaced by algorithmic monitoring platforms. This continuous risk assessment strengthens internal controls over financial reporting (ICFR) and significantly reduces fraud risk.

Evolving Roles for Accounting Professionals
As routine data entry and manual reconciliation tasks become fully automated, the skill set required for accounting professionals is shifting toward data analysis, system design, and strategic business advisory.
– Systems Governance: Accountants are increasingly responsible for monitoring algorithmic accuracy and managing data integration pipelines.
– Business Partnership: Finance professionals leverage real-time financial dashboards to advise operational leaders on margin management and working capital allocation.
– Regulatory Compliance Management: Accounting teams utilize automated platforms to ensure compliance with dynamic tax codes and international accounting standards.

Core Implementation Recommendations
1. Deploy Automated Reconciliation Tools: Integrate continuous transaction processing modules into existing enterprise ERP architectures.
2. Establish Algorithmic Governance Controls: Implement strict internal testing protocols to ensure automated accounting rules comply with GAAP/IFRS standards.
3. Reskill Accounting Teams: Invest in training finance staff on data analytics, workflow automation, and predictive financial modeling.

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Accounting

Global ESG Reporting Standards and Double Materiality Compliance

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Corporate accounting departments face expanding reporting expectations as international sustainability disclosure standards achieve regulatory enforcement across major global jurisdictions. Chief Accounting Officers (CAOs) and corporate controllers are establishing rigorous internal accounting controls to treat Environmental, Social, and Governance (ESG) metrics with the same data precision, auditability, and governance as traditional financial statements.

Regulatory Harmonization Under Global Sustainability Frameworks
The implementation of standardized sustainability reporting frameworks—notably rules established by international sustainability accounting boards—has created unified expectations for public and large private enterprises. Corporations must report standardized metrics covering greenhouse gas emissions (Scope 1, 2, and material Scope 3), energy utilization, workforce demographics, and supply chain governance.

In Europe and other participating international jurisdictions, double materiality principles are mandatory. Under double materiality, organizations must report both how external sustainability risks impact corporate financial performance, and how internal corporate operations affect surrounding environmental and social structures.

Integrating Sustainability Metrics into Core ERP Systems
To provide auditable non-financial data, enterprise organizations are integrating specialized carbon accounting and ESG management platforms directly into core ERP systems. Automated data collectors capture energy utility invoices, logistics fuel consumption metrics, and vendor compliance records in real time.

Establishing automated, traceable data pipelines ensures that non-financial reporting is supported by clear audit trails. This structured approach allows external financial auditors to provide reasonable assurance on sustainability disclosures during annual corporate reporting cycles.

Financial Impacts and Capital Market Disclosure
Accurate ESG reporting directly influences corporate cost of capital and institutional credit ratings. Commercial lenders and institutional asset managers systematically incorporate sustainability metrics into risk pricing models. Companies that demonstrate transparent, verifiable progress in operational energy efficiency and climate risk mitigation benefit from expanded access to green bond markets and lower debt pricing.

Action Steps for Accounting Leadership
1. Implement Double Materiality Frameworks: Conduct comprehensive assessments to identify material financial and operational sustainability metrics.
2. Build Auditable Non-Financial Data Pipelines: Automate ESG data collection within core accounting software to ensure data integrity.
3. Align Sustainability with Annual Financial Filings: Prepare non-financial disclosures concurrently with financial statements to satisfy regulatory audit expectations.

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Accounting

Modernizing Internal Controls: Machine Learning and Continuous Monitoring in Auditing

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Internal audit departments and corporate risk managers are modernizing internal control frameworks by shifting from periodic sampling techniques to continuous monitoring and machine learning analytics. As operational data volumes increase across enterprise organizations, automated control testing ensures financial integrity, prevents corporate fraud, and streamlines annual audit engagements.

The Limitation of Periodic Audit Sampling
Historically, internal and external auditors evaluated internal controls by reviewing random samples of financial transactions—often analyzing less than five percent of total ledger entries. In complex enterprise environments, periodic sampling methods carry inherent risks of overlooking localized financial misstatements, unauthorized disbursements, or operational control breakdowns.

In 2026, progressive internal audit functions are utilizing automated continuous monitoring platforms that evaluate one hundred percent of financial transactions in real time. Continuous control auditing systems continuously monitor general ledger entries, procurement approvals, and expense reimbursements across all operating subsidiaries.

AI-Powered Fraud Detection and Anomaly Identification
Machine learning models trained on historical corporate financial data excel at identifying subtle transactional anomalies that indicate potential fraud or operational error. Automated systems instantly flag duplicate invoice payments, unapproved vendor creation, unusual journal entry timing, and unauthorized override of authority thresholds.

When an anomaly is detected, the automated auditing platform generates an instant risk alert, allowing internal audit teams to investigate root causes immediately. Early detection prevents minor operational errors from escalating into material weaknesses in financial reporting.

Streamlining External Audit Preparation
Continuous internal control monitoring delivers significant benefits during annual external financial audits. External audit firms can review continuous audit logs and automated control testing documentation, reducing the time required for manual field testing.

This integrated approach lowers overall audit compliance fees, reduces administrative burdens on corporate accounting staff, and provides senior management and audit committees with real-time visibility into the organization’s overall risk profile.

Core Implementation Guidelines
1. Transition to 100% Data Testing: Replace legacy sampling methods with automated continuous audit monitoring systems.
2. Deploy Anomaly Detection Algorithms: Implement machine learning models to identify unauthorized transactions and operational control overrides.
3. Align Internal and External Audit Workflows: Coordinate continuous control testing protocols with external auditors to optimize annual compliance cycles.

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