If you’re a Streeterville business owner staring at an IRS notice, struggling with disorganized books, or unsure whether you’re overpaying on taxes, you need more than a seasonal tax preparer – you need a CPA firm that understands the specific accounting and tax services demands of operating in one of Chicago’s most dynamic neighborhoods. Massey and Company CPA provides year-round tax, bookkeeping, and IRS resolution support built for small businesses, real estate investors, nonprofits, and individuals across the Streeterville area.
Call (773) 828-0551 for a free consultation or visit masseyandcompanyCPA.com to get started. Your can also email us at info@masseyandcompanyCPA.com.
Over 30 years of tax expertise – The firm management brings decades of hands-on experience to every client engagement.
CPA + Enrolled Agent credentials – The firm combines Certified Public Accountant leadership with Enrolled Agents, who are licensed by the IRS to represent taxpayers in audits, collections, and disputes.
Certified QuickBooks ProAdvisors – The team is certified by Intuit to implement, optimize, and troubleshoot QuickBooks Online, ensuring your accounting software works for your business rather than against it.
Proven IRS resolution track record – Multiple client reviews confirm Massey and Company CPA has resolved IRS issues with positive outcomes, including tax debt negotiations and penalty relief cases.
Cloud-first, secure systems – Real-time access to your financial data through cloud accounting services means you can review numbers from your home, office, or anywhere in the Chicago area.
Streeterville businesses operate in one of Chicago’s highest-cost commercial corridors, where mixed-use properties, complex city and state tax obligations, and fast-moving revenue cycles create accounting challenges that generic firms often miss. Massey and Company CPA’s team helps guide clients through these Streeterville-specific accounting and tax issues because they work with businesses navigating them every day – from LLC owners managing rental properties along the Magnificent Mile to nonprofits filing complex federal and Illinois returns.
Year-round partnership, not seasonal contact – Massey and Company CPA provides ongoing strategy calls, monthly reports, and proactive tax planning so you’re never caught off guard by a filing deadline or regulatory change.
Cloud-first technology with personal relationships – You get the efficiency of modern cloud accounting services paired with a dedicated team that’s available even on weekends, and you can meet virtually or in person when needed, as clients have noted in published reviews.
Transparent pricing with no surprises – Fixed monthly fees for bookkeeping and clear quotes for tax preparation mean you know exactly what you’ll pay before work begins.
Deep Illinois compliance knowledge – From Illinois Department of Revenue rules to Chicago business licensing requirements, the firm stays current to ensure compliance with state and city requirements that directly affect your bottom line.
Massey and Company CPA offers a full suite of accounting, tax, and consulting solutions for clients across multiple industries who live and work in Streeterville – professionals with complex personal finances, small businesses managing cash flow in a competitive market, real estate investors tracking depreciation and leasing expenses, and nonprofits navigating strict compliance requirements, providing support tailored to their needs and long-term success.
The firm prepares individual and business tax returns for federal, Illinois state, and multi-state filers, including returns you may need to file such as Form 1120S and Schedule C. Entity types include LLCs, S Corps, C Corps, partnerships, trusts, estates, and nonprofits. But tax services at Massey and Company CPA go well beyond filing – proactive tax planning runs throughout the year with strategies covering entity structuring, retirement contributions, charitable giving, Roth conversions, and deductions specific to Illinois.
For Streeterville residents and business owners, this means identifying every legitimate deduction and credit before tax season arrives, including common deductions tied to home ownership and student loans, not scrambling to find them after. The focus is on reducing your total tax liability legally and strategically, whether you’re a high-income individual or a growing company.
Disorganized books cost you money – missed deductions, inaccurate cash flow projections, and audit exposure all stem from financial records that haven’t been maintained properly. Massey and Company CPA provides monthly bookkeeping, reconciliations, financial reporting, and bookkeeping and payroll processing services that keep your numbers current and actionable, especially if your business has over $250,000 in revenue.
As certified QuickBooks ProAdvisors, the team handles QuickBooks Online setup mapped to your business model or industry needs – whether retail, real estate, or nonprofit. They also provide cleanup of messy books, staff training, and workflow optimization. Clients who have gone through this process report improved visibility into their finances, better preparation for tax filing and business decisions, and stronger systems backed by better tools and resources.
Receiving an IRS letter or dealing with the Illinois Department of Revenue can feel overwhelming. Massey and Company CPA represents clients before the IRS and state agencies to resolve audits, unpaid taxes, liens, levies, and wage garnishments. The firm negotiates Offers in Compromise, installment agreements, penalty abatements, and can help qualifying taxpayers achieve “currently not collectible” status.
For individuals and businesses with unfiled returns, the firm restores compliance and works to minimize penalties, including for businesses that sell across state lines and need help resolving multi-state filing obligations. This service is critical for anyone who has fallen behind – whether it’s one missed year or several – and needs a clear path back to good standing with tax authorities.
For Streeterville businesses seeking strategic financial leadership without the full-time cost, Massey and Company CPA offers fractional CFO and controller services. This flexible option provides expert guidance on budgeting, cash flow management, financial forecasting, and performance analysis tailored to your unique business needs.
Our Chicago team understands that many small to mid-sized businesses require high-level financial insights to make informed decisions and drive growth but may not yet need or afford a full-time CFO. By partnering with Massey and Company CPA, you gain access to experienced financial professionals who act as your trusted partner, delivering customized reports and actionable advice that align with your goals.
Whether you need help establishing internal controls, preparing for investor presentations, or optimizing your financial operations, our team understands the complexities of the Streeterville market and Illinois regulations. Learn how a fractional CFO can elevate your business strategy and provide peace of mind with expert oversight.
Click to contact Massey and Company CPA today to explore how these services can fit your business model and budget.
Contact Massey and Company CPA to schedule a free initial consultation. During this conversation, you’ll discuss your financial situation, goals, and any pressing issues – whether that’s an IRS notice, disorganized bookkeeping, or a need for better tax planning. The team assesses your current accounting systems and identifies exactly what services will benefit your situation.
After the consultation, you receive a customized service plan with transparent pricing and a clear timeline. The firm sets up your cloud-based systems, establishes a regular communication schedule, and begins work – whether that means cleaning up prior-year books, preparing returns, or responding to IRS correspondence on your behalf.
Massey and Company CPA doesn’t disappear after tax season. You receive regular reports – month by month or quarterly – along with strategy calls and proactive updates on tax law changes affecting Streeterville businesses and individuals. This ongoing partnership ensures you’re always positioned to minimize taxes, maintain compliance, and make informed financial decisions throughout the year.
Real client experiences illustrate what working with Massey and Company CPA looks like in practice:
“Massey and Company helped us with an IRS issue and it was resolved with a positive result.”
The team was “prompt and attentive… even over the weekends” and helped with “detangling both personal and business expenses.”
These outcomes reflect the firm’s commitment to responsive service and real problem resolution – not just filing paperwork but actively guiding clients through complex tax and accounting challenges to reach peace of mind.
Massey and Company CPA serves clients throughout the Chicago metro area, with a strong focus on Streeterville and surrounding neighborhoods:
Streeterville
River North
Gold Coast
The Loop
West Loop Gate
Humboldt Park
Brighton Park
East Garfield Park
The firm’s cloud-based service model means clients across Chicago, IL and beyond can access full accounting, tax, and consulting support virtually. With CPA licensing and multi-state filing capabilities, the firm also serves individuals and businesses with tax obligations outside Illinois.
Massey and Company CPA uses fixed monthly fees for bookkeeping services, so there are no surprises on your bill. Tax preparation and consulting fees depend on complexity – factors include entity type, number of transactions, prior record condition, and whether multi-state filing is required. You’ll receive clear pricing during your initial consultation before any work begins.
The firm operates as a cloud-first company, with virtual meetings and secure online collaboration as the primary method for most engagements. This gives you real-time access to your financial data from any location. In-person meetings are available for complex situations or clients who prefer face-to-face interaction.
Massey and Company CPA focuses on small businesses, entrepreneurs, nonprofits, real estate investors, and individuals with moderate to complex tax situations – not large corporations. You work with a consistent team that knows your financial history, maintains year-round contact, and in addition to core CPA support, proactively advises you on changes in tax law. The firm has operated since 2013, bringing over 30 years of founder expertise and a suite of modern cloud accounting tools to every engagement.
Yes. Catch-up bookkeeping and financial record cleanup is one of Massey and Company CPA’s core services. The team will organize intertwined personal and business expenses, reconcile accounts, and set up systems to prevent future disorganization. Timeline depends on severity – multiple years of unfiled returns or missing bank statements require more reconstruction time – but the firm provides a realistic schedule during your consultation so you know what to expect.
Streeterville business owners and individuals who are ready to stop worrying about taxes, organize their books, and build a financial foundation for growth can take the first step today. Get in touch with Massey and Company CPA to schedule your free consultation, get clear answers, transparent pricing, and know your next steps.
Massey and Company CPA · (773) 828-0551 · masseyandcompanyCPA.com · Or reach out to us by email at info@masseyandcompanyCPA.com. Serving Steeterville, Chicago and surrounding areas.
