A Massachusetts CPA You Can Actually Talk To

Michael Connelly, CPA
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Michael Connelly, CPA , Principal

Title Principal
Hometown Boston, MA
Years of Experience 10+
Education
Providence
It’s not so much what we have in this life that matters. It’s what we do with what we have.

— Fred Rogers

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Certifications
  • Certified Public Accountant
  • Masters of Business Administration
  • QuickBooks Pro Advisor
  • Blue Belt in Brazilian Jiu-Jitsu
Specialties
  • Small Business Tax Strategy
  • Business Advisory
  • Personal Finance
  • Entity Structure Analysis
  • Strategic Tax Planning
Industries
  • Health & Fitness
  • Medical Practices
  • Professional Services
  • Trade Businesses
  • Sole Proprietors
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Your Massachusetts CPA for Tax & Accounting Advisory

Boston’s economy—powered by life sciences, healthcare, higher education, finance, tech, and professional services—demands a CPA who pairs strategy with execution. Your dedicated Boston CPA, Michael Connelly, CPA , provides tax strategy, tax compliance, bookkeeping & outsourced accounting, to minimize liabilities, improve financial clarity, and position individuals and businesses for long‑term success across Greater Boston.

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Michael Connelly, CPA

Michael Connelly, CPA, Principal

As a CPA, my priority is building strong personal relationships with clients while delivering proactive advisory that ensures there are no surprises come tax time. I take pride in removing the stress of tax and accounting, providing clear guidance and education on one of the most important financial areas of their lives.

Tax Strategy & Accounting Solutions for Boston Businesses

The Problem: Many Boston companies lack timely, accurate financials—or the strategic tax guidance needed to grow. Massachusetts layers on corporate excise tax, sales & use tax (economic nexus), payroll and withholding, PFML contributions, and market‑based sourcing for services. Missed quarterly estimates, apportionment errors, or ignoring the elective PTE tax (SALT workaround) can be costly.

The Solution: We combine bookkeeping, tax compliance, and proactive tax strategy for Boston businesses. We manage corporate excise and sales/use filings, payroll/PFML, quarterly estimates, apportionment & market‑based sourcing, and elective PTE planning—while delivering cash‑flow forecasting, KPI reporting, budgeting, and growth strategies. With our Advisory‑First approach, you get tax‑smart, data‑driven decisions all year.

Michael Connelly, CPA

Michael Connelly, CPA, Principal

Having a CPA manage your accounting, tax planning, and filings is a game-changer. Connecting these functions maximizes savings, ensures accurate financials, and drives proactive strategies for growth and success.

Tax Strategy & Compliance for Boston Locals

The Problem: Many Boston residents don’t discover tax issues until filing—unexpected balances, missed deductions, or overlooked planning opportunities. With Massachusetts state income tax, the 4% surtax on income over $1M, short‑term capital gains at higher rates, property taxes, equity compensation, and complex federal rules, proactive planning is essential.

The Solution: At Dark Horse CPAs, we believe in No Surprises. We work year‑round to reduce liability and keep you compliant—optimizing retirement and tax‑deferral strategies, charitable planning, equity comp (ISOs/NSOs/RSUs), multi‑state considerations, and real estate/investment tax. Every engagement includes a personalized, forward‑looking tax plan so you can move ahead with clarity and confidence.

Michael Connelly, CPA

Michael Connelly, CPA, Principal

Too many CPAs skip regular check-ins, but proactive reviews are essential for uncovering opportunities and driving effective tax planning. Every engagement should include at least an annual review—maximizing your CPA relationship, creating tax savings, and providing insights that optimize financial outcomes year after year.

Insights & Updates from Your Trusted Dark Horse CPA

The Dark Horse Blog, where we share expert insights on tax strategy, compliance updates, outsourced accounting , fractional CFO services, and more. Our content is tailored to small and medium-sized businesses as well as high-net-worth individuals.

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