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Cloud computing tax threatens Chicago’s Silicon Valley ambitions

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Chicago’s bid to become the Silicon Valley of the Midwest has registered some major wins in recent years: Google bought a huge downtown building, PsiQuantum Corp. announced a $1 billion investment in the city, and local startups raised a record $19 billion in 2022.

Now a move to increase an unusual tax on cloud computing risks adding to a broader technology industry downturn to derail progress in the third-largest U.S. city.

Faced with a nearly $1 billion deficit for next year, Mayor Brandon Johnson has proposed an additional $128 million in revenue by increasing the levy, first implemented in 2016. The plan, expected to be voted on by the City Council’s finance committee on Tuesday, is spurring criticism from business leaders already fighting the progressive politician over everything from crime to the future of the city’s schools.

“This isn’t good,” said Chris Deutsch, founder of Chicago-based Lofty Ventures, which invests in startups. “They’re just going to keep ratcheting up these taxes and it’s going to really hurt business and the entire tech community here. Maybe not immediately but over time, this is a terrible trend and will absolutely hurt us.”

Johnson, a former union organizer who surprised pundits when he beat incumbent Lori Lightfoot, had already alienated many of the city’s economic leaders by proposing a series of taxes on the rich. All at a time when the Chicago area is contending with the loss of firms including Citadel, Boeing Co., Caterpillar Inc. and the local offices of Tyson Foods Inc.

The mayor’s plan to raise taxes on sales of million-dollar homes failed in a referendum and Illinois Governor JB Pritzker said he would block Johnson’s ambitions to establish a financial transaction tax. Raising the levy on cloud computing could be a solution after City Council members rebuked Johnson’s plan for a $300 million property tax increase in a historic 50-0 vote.

“That one is the least egregious of a lot of things that are out there,” said Alderman Brian Hopkins, who said Johnson is getting closer to securing the votes he needs to pass the budget before the Dec. 31 deadline. 

A spokesperson for the city’s finance and budget departments said the tax is based on usage, minimizing the impact on small businesses. For example, a small business using the starter suite of Salesforce Inc. for one user would see the levy increase by just 50 cents a month, according to a statement to Bloomberg.

“This approach balances the need for additional revenue with the city’s commitment to supporting economic growth and remaining an attractive environment for businesses of all sizes,” the spokesperson said.

Competitive disadvantage

Chicago is one of few cities in the country that taxes cloud computing and software — others include Denver and Washington, D.C. The tax, known as the Personal Property Lease Transaction, would be increased to 11% from the current rate of 9%.

Lucy Dadayan, a principal research associate at the Urban Institute warned that the levy may have “unintended consequences” by putting Chicago at a a competitive disadvantage.

“I don’t know the details of how this will come out, but the concern would be that you’re just driving people away from doing business in Chicago,” said Keith Todd, chief executive officer of Trading Technologies, a Chicago-based platform that offers clients access to derivatives trading. “All it will mean is that consumers will be disadvantaged.” 

Chicago’s tech community experienced a surge in growth after the pandemic, when work-from-home became the norm, allowing people to move to places with a lower cost of living like Chicago. Startups in the city raised $19.2 billion in 2022, an increase of 85% from a year earlier. Funds became much more scarce last year due to high interest rates and a broader downturn that saw tech companies lay off workers across the country.

The city also gained a boost when Alphabet Inc.’s Google announced in 2022 that it was buying the James R. Thompson Center, an underused government-owned building that occupies a full city block downtown. A year earlier, the company made a $1 billion equity investment in Chicago-based CME Group Inc. to accelerate the U.S.’s largest derivatives exchange’s move to the cloud.

In July, PsiQuantum said it would invest more than $1 billion to become the anchor tenant at a new quantum and microelectronics park planned by Pritzker in the South Side of Chicago.

The Illinois governor, who founded tech startup incubator 1871, has been key in trying to turn the state into a hub for new technologies from quantum to electric vehicles and data centers. His sister Penny Pritzker, former Secretary of Commerce, has also given the city a boost with her nonprofit P33, which aims to turn Chicago into a center of innovation by 2033.

Chicago startups

Cloud computing is essential to many up-and-coming tech companies, which often use the cloud as their main form of software distribution, according to Betsy Ziegler, CEO of 1871.  

“I’m less worried about Google and Amazon Web Services, I’m way more worried about the growth company that is trying to scale that has very constrained funds,” she said. “Does this create a constraint that reduces Chicago’s competitive environment to attract those companies to build here?” 

While Chicago’s tech community has grown, the city only ranked 23 among top markets, according to an analysis by commercial real estate firm CBRE which used metrics including talent concentration, labor costs and attractiveness to companies. The city has also lost 9.5% of its tech workforce between 2018 and 2023, with the most of the decline taking place last year.

Cloud computing is now almost as commonplace as email in most workplaces, becoming an attractive source of revenue for governments. When Chicago started taxing the service in 2016, the rate was just 5.25%. Lightfoot boosted it to 9% during the pandemic. If Johnson’s proposal goes ahead, the 11% rate will bring a total of $818 million in revenue for the city, said Budget Director Annette Guzman. 

The tax isn’t just a challenge for tech firms. About 5,000 companies are registered for the Personal Property Lease Transaction Tax, according to data from the city. These include CME, Citadel, Salesforce, Kraft Heinz Food Company, as well sports teams such the Cubs, the Blackhawks and the White Sox. 

“We are strongly opposed,” said Jack Lavin, chief executive officer for the Chicagoland Chamber of Commerce. “This goes to the heart of what we are trying to do, which is to grow the economy.”

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Tax Fraud Blotter: Reaping and sowing

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Share and share alike; fleecing the flock; United they fall; and other highlights of recent tax cases.

Shreveport, Louisiana: Tax preparer Sharhonda Law, 39, of Haughton, Louisiana, has been sentenced to 20 months in prison, to be followed by a year of supervised release, for tax fraud.

She owned and operated Law’s Tax Service, where she was the sole preparer. Law prepared and filed a client’s 2019 federal return that included a fraudulent Schedule F that claimed the client had farming income and had incurred farming expenses and was due a refund. In fact, the client owed taxes for that year. Investigation also showed that Law’s client did not have a farm, nor did they tell Law they owned or operated a farm and had never provided Law with any of the farming-related income or expenses on the Schedule F.

Law pleaded guilty in November to one count of aiding and assisting in making and subscribing a false return.

She made similar misrepresentations on six other returns for clients and falsified her own income on two of her personal returns; she also failed to file returns for other years. The total criminal tax loss was $123,455, which Law was ordered to pay in restitution.

Evansville, Indiana: Marcie Jean Doty, operations manager for a property management business, has been sentenced to five years in prison, to be followed by three years of supervised release, after pleading guilty to wire fraud, failure to file returns and filing false returns.

Between May 2017 and June 2022, Doty stole some $1,803,466.38 from her employer via unauthorized checks and ACH transfers. She executed 99 unauthorized transfers, totaling $503,151.59, and wrote 279 unauthorized checks to herself, totaling $1,300,314.79. The funds were transferred from her employer’s bank accounts to her personal ones. Doty entered false information in the business accounting software, representing that the checks were written to her employer instead of herself. 

In January 2017, Doty agreed to purchase a 25% equity share in her employer’s business. Doty used some of the money she stole via the scheme to make payments towards her purchase of the share.

For tax years 2018 through 2020, Doty didn’t report the income derived from her scheme, failing to report some $786,280.70. She also didn’t file returns for tax years 2021 and 2022, failing to report some $1,006,983.84 in income.

She has been ordered to pay $2,517,343.05 in restitution.

Crofton, Kentucky: Marvin Upton has been sentenced to two years and three months in prison, to be followed by three years of supervised release, for fraud and tax offenses.

Upton, until recently the pastor at local Crofton Pentecostal Church, was sentenced for three counts of bank fraud and three counts of filing false returns. From 2013 to 2016, Upton defrauded one of his elderly parishioners, who suffered from dementia. During that same time, Upton submitted multiple false returns that omitted income from the fraud.

Jacksonville, Florida: Exec Daniel Tharp has pleaded guilty to failure to pay taxes. 

Tharp was managing director for Hangar X Holdings LLC, where he had the responsibility to collect and account for the company’s trust fund taxes from employees’ pay. From October 2014 through December 2019, the company paid wages to employees and withheld these, but Tharp didn’t pay the money to the IRS. In total, he caused the company to fail to pay over $1.2 million in such taxes.

He faces a maximum of five years in prison.

Hands-in-jail-Blotter

Detroit: A federal court in Michigan has issued an injunction against tax preparers Alicia Bishop and Tenisha Green, barring them from preparing federal returns for others.

The court previously barred Alicia Qualls, Michael Turner and Constance Stewart from preparing federal returns for others and previously barred the business for which all of the preparers worked, United Tax Team Inc., and United Tax Team’s incorporator, Glen Hurst, from preparing federal returns for others.

Hurst, United Tax Team, Qualls, Turner and Stewart consented to the judgments.

According to the complaint, Hurst incorporated United Tax Team in 2016, and was its sole shareholder and corporate officer. Hurst hired the return preparers — including Qualls, Bishop, Green, Turner and Stewart — who worked at United locations in the Detroit area and prepared returns for clients that included false information not provided by clients.

The complaint alleges that Qualls, Bishop, Green, Turner and Stewart each repeatedly placed false or incorrect items, deductions, exemptions or statuses on returns without clients’ knowledge, including, in various cases, fabricated Schedule C businesses; fabricated education expenses; improperly claimed pandemic relief tax credits; improperly claimed head of household status; and fictitious child and dependent care expenses.

Akron, Ohio: Tax preparer Mustafa Ayoub Diab, 41, of Ravenna, Ohio, has been convicted of orchestrating a financial conspiracy that defrauded the U.S. government of pandemic benefits.

Diab was found guilty on 12 counts of theft of government funds, 12 counts of bank fraud, 11 of wire fraud, six of aggravated ID theft and one count each of conspiracy to commit wire and bank fraud and to launder monetary instruments.

Diab owned and operated a tax prep business where he and his co-conspirator, Elizabeth Lorraine Robinson, 33, also of Ravenna, developed a scheme to take advantage of the Pandemic Unemployment Assistance Program and the Paycheck Protection Program. From around June 2020 to August 2021, Diab submitted fraudulent applications for pandemic unemployment benefits and small-business assistance for many of his tax prep business clients.

Without their knowledge, he lied about their employment or about their being small-business owners. Investigators also discovered that Diab opened bank accounts in his clients’ names to receive the benefit funds via direct deposit, which the clients did not have access to, along with accounts in the names of Robinson and Diab’s sister. When the relief money was deposited into these accounts, he withdrew the funds in cash for his personal use, buying real estate and cars and taking international trips.

Diab submitted fraudulent applications in the names of nearly 80 victims, causing the federal government to pay out more than $1.2 million in pandemic benefits that were deposited into the various bank accounts that Diab controlled.

Sentencing is July 28. He faces up to 30 years in prison.

Robinson previously pleaded guilty to conspiracy, wire fraud, bank fraud and theft of government funds; she awaits sentencing and also faces up to 30 years in prison.

Columbus, Ohio: A federal court has permanently enjoined tax preparer Michael Craig from preparing returns for others and from owning or operating any prep business.

Craig, both individually and d.b.a. Craig’s Tax Service, consented to entry of the injunction. 

According to the complaint, many tax returns that Craig prepared made false and fraudulent claims, including losses for fictitious Schedule C businesses; claiming costs of goods sold for types of businesses that cannot claim these costs and without supporting documentation; inventing or inflating expenses for otherwise legitimate Schedule C businesses; and taking deductions for both cash and non-cash charitable deductions that are either exaggerated or fabricated.

According to the complaint, the IRS estimated a tax loss of more than $3.1 million in 2022 alone.

Craig must send notice of the injunction to each person for whom he prepared federal returns or refund claims after Jan. 1, 2022.

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IRS proposes to end penalties on basis-shifting transactions

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The Treasury Department and the Internal Revenue Service are planning to withdraw regulations that labeled basis-shifting transactions among partnerships and related parties as “transactions of interest” akin to tax shelters and stop imposing penalties on them.

In Notice 2025-23, the Treasury and the IRS said Thursday they intend to publish a notice of proposed rulemaking proposing to remove the basis-shifting TOI regulations from the Income Tax Regulations.  

The notice provides immediate relief from penalties under Section 6707A(a) to participants in transactions identified as transactions of interest in the Basis Shifting TOI Regulations that are required to file disclosure statements under Section 6011, and (ii) penalties under Sections 6707(a) and 6708 for material advisors to transactions identified as transactions of interest in the basis-shifting regulations that are required to file disclosure statements under § 6111 and maintain lists under Section 6112.  

The notice also withdraws Notice 2024-54, 2024-28 I.R.B. 24 (Basis Shifting Notice), which describes certain proposed regulations that the Treasury Department and the IRS intended to issue addressing partnership related-party basis-shifting transactions.

The Treasury and the IRS issued the final regulations in January after receiving comments that the original proposed regulations could impose burdens on small, family-run businesses and impact too many partnerships. However, the American Institute of CPAs has urged the Treasury and the IRS to suspend and remove the rules, arguing they were “overly broad, troublesome and costly” after requesting changes in the proposed regulations last year.

The IRS and the Treasury acknowledged in Thursday’s notice that it had heard similar objections. “Taxpayers and their material advisors have criticized the Basis Shifting TOI Regulations as imposing complex, burdensome, and retroactive disclosure obligations on many ordinary-course and tax-compliant business activities, creating costly compliance obligations and uncertainty for businesses,” said the notice.

It cited an executive order in February from President Trump on implementing a Department of Government Efficiency deregulatory initiative, which directs agencies to initiate a review process for the identification and removal of certain regulations and other guidance that meet any of the criteria listed in the executive order. The Treasury and the IRS identified the Basis Shifting TOI Regulations for removal and the Basis Shifting Notice for withdrawal.

Last June, former IRS Commissioner Danny Werfel announced a crackdown on related-party basis-shifting transactions that enable partnerships to avoid paying taxes and issued guidance after the IRS uncovered tens of billions of dollars of questionable deductions claimed in a group of transactions under audit.  

“Our announcement signals the IRS is accelerating our work in the partnership arena, an arena that has been overlooked for more than a decade with our declining resources,” said Werfel during a press conference last year. “We’re concerned tax abuse is growing in this space, and it’s time to address that. So we are building teams and adding expertise inside the agency so we can reverse these long-term compliance declines.” 

Using complex maneuvers, high-income taxpayers and  corporations would strip the basis from the assets they owned where the basis was not generating tax benefits and then move the basis to assets they owned where it would generate tax benefits without causing any meaningful change to the economics of their businesses. The basis-shifting transactions would enable closely related parties to avoid paying taxes. The Treasury estimated last year that the transactions could potentially cost taxpayers more than $50 billion over a 10-year period.

“For example, a partnership might shift tax basis from a property that does not generate tax deductions, such as stocks or land, to property where it does, like equipment,” said former Deputy Secretary of the Treasury Wally Adeyemo during the same press conference. “Businesses have also used these techniques to depreciate the same asset over and over again.”

Congress has since removed much of the extra funding from the Inflation Reduction Act that was being used to scrutinize such transactions, and the IRS has been downsizing its staff in recent months, reducing its enforcement and audit teams, with plans for further cutbacks in the weeks and months ahead. 

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Tax-busting ETF-share class filing updates keep piling up

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Optimism is building that a game-changing fund design that will help asset managers shrink clients’ tax bills and grow their ETF businesses will soon be approved by the U.S. securities regulator.

This week, at least seven firms including JPMorgan and Pacific Investment Management Co. filed amendments to their applications to create funds that have both ETF and mutual fund share classes. The filings update initial applications — some of which sat idle for months — with more details about the fund structure, and suggest the U.S. Securities and Exchange Commission has engaged in constructive discussions with a growing number of applicants, according to industry lawyers.

“The SEC signaling is clear. These amendments really constitute the SEC prioritizing ETF share class relief,” said Aisha Hunt, a principal at Kelley Hunt law firm, which is working with F/m Investments on its application. 

The latest round of filings, which also include Charles Schwab and T. Rowe Price, are serving as yet another sign that the SEC is fast-tracking its decision process on multi-share class funds, after F/m Investments and Dimensional Fund Advisors filed amendments earlier in April. DFA’s amendment included more details around fund board reporting and the board’s responsibilities to monitor the fairness of the new structure for each shareholder.

Brian Murphy, a partner at Stradley Ronon, the firm handling DFA’s filing, said other fund managers are receiving feedback and amending applications.

“We understand that the SEC staff is telling other asset managers to follow the DFA model as well,” said Murphy, who is also a former Vanguard lawyer and SEC counsel.

At stake is a novel fund model where one share class of a mutual fund would be exchange-traded. It was patented by Vanguard over two decades ago, and helped the money manager save its clients billions on taxes. The blueprint ports the tax advantages of the ETF onto the mutual fund, and is a tantalizing prospect for asset managers that are seeing outflows and looking to break into the growing ETF industry. 

After Vanguard’s patent on the design expired in 2023, over 50 other asset managers asked the SEC for so-called “exemptive relief” to use the fund design. But it wasn’t until earlier this year, when SEC acting chair Mark Uyeda said the regulator should prioritize the applications, that it was clear the SEC would be interested in allowing other fund firms to use the model.

According to Hunt, the regulator has signaled that it will first approve a small subset of the applicants. 

‘Work to be done’

To be sure, an approval doesn’t mean that an issuer will be able to immediately begin using the fund blueprint. Because ETFs trade during market hours, they require different infrastructure than mutual funds, so firms that currently only have the latter structure will need to hire staff and form relationships with ETF market makers before they implement the dual-share class model. 

“Dimensional has sort of set the template for what that language looks like in the context of these filings. And by extension cleared the way for approval, which feels imminent now,” said Morningstar Inc.’s Ben Johnson. “But then once we arrive at approval, there’s still going to be work to be done.”

Mutual fund firms will need to prepare for shareholders who want to convert, tax-free, into the ETF share class, which would require some “plumbing” and structural changes, said Johnson.

Another point to consider is that mutual funds that have significant outflows may not be ripe for ETF share classes, as that could result in a tax hit, according to research from Bloomberg Intelligence. In 2009, a Vanguard multishare class fund was hit with a 14% capital-gains distribution after a massive shareholder redeemed its shares in the fund. Fund outflows can bring about a tax event when a mutual fund has to sell underlying holdings to meet redemptions. 

Mutual funds have largely bled assets in recent years as ETFs have grown in popularity. As a result, legacy asset managers have found themselves battling for a slice of the increasingly saturated ETF market, which now boasts over 4,000 U.S.-listed ETFs. SEC approval of the dual-share design could open the floodgates to thousands more funds. 

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