A Massachusetts CPA You Can Actually Talk To
Michael Connelly, CPA
TITLE
Principal
HOMETOWN
Boston, MA
YEARS OF EXPERIENCE
10
EDUCATION
It’s not so much what we have in this life that matters. It’s what we do with what we have.
— Fred Rogers
People generally understand that Rhode Island is the smallest state in the union. Many folks, however, would have a bit of difficulty pinpointing it on a map. Similarly, a Dark Horse doesn’t stand out from its surroundings immediately either. A closer look, however, might reveal clues that beneath the surface, a Dark Horse has what it takes to win. As you may have guessed, the Dark Horse in question is Michael Connelly from Rhode Island and the fire beneath the surface to disrupt public accounting and provide unparalleled value to his clients burns bright.
Mike earned his bachelor’s degree in accounting and MBA from Providence College, where he also met his bride-to-be their senior year. Shortly into his career, he earned his CPA license from the state of Rhode Island. He comes to Dark Horse with a decade of experience in public accounting, working with small businesses (and their owners) spanning just about any industry you can think of. He’s passionate about helping these small businesses understand their tax and financial situations and use that understanding to make strategic moves that increase profitability and decrease taxes.
On the personal side of life, Mike enjoys spending time with family and friends, especially at the beach or on a trip to Disney World. He lives in a small coastal town in Massachusetts, in between Boston and Plymouth. He loves his Boston sports teams, skiing and training Brazilian Jiu Jitsu (although we’d suspect that training doesn’t include family and friends, but who knows…). And, as any self-respecting Dark Horse CPA, Mike is well versed in The Office and Parks & Rec.
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
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.
MICHAEL CONNELLY, 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.”
80%
Net Promoter Score
The average NPS for accounting firms is 38%. At Dark Horse, 80% of our clients would recommend us to a friend.
Net Promoter Score
Companies use this metric to gauge how happy their customers are with their services. It's calculated by taking the percentage of "promoters" minus the % of "detractors. "The average NPS score for the accounting industry is 39%, less than the DMV! We believe it's important to share that we have successfully fulfilled our promise to WOW clients and consistently monitor this metric to ensure we continue to deliver on the highest level.
550+
5-Star Reviews
Our Google and Yelp reviews speak for themselves. Our goal is to provide 5-star service to every client, every time.
5-Star Reviews
When someone shares their experience with us online, we find it extremely valuable to know where we've exceeded expectations and where we can improve. Many of our clients decide to engage with us as a result of reading about other Dark Horse clients’ experiences. Even when things do not go as planned, we do everything we can to make it right.
90%
Retention Rate
We're all about creating long-lasting, value-added relationships.
Retention Rate
This is the frequency of repeat business from our clients that work with us. This means that 9 out of 10 clients use us for subsequent years. That shows us that people enjoy working with our CPAs, are pleased with the work, and want to continue with Dark Horse over the long term.
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 CONNELY, 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, 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.”
Porscha D.
Working with Mike Connelly has been great! We had some complicated things to get through but it was not a problem for him. Other accountants I’ve worked with seem overwhelmed and it reflects in their work. Mike specifically mentioned Dark Horse being very supported as a contrast to other places he worked. My experience with Dark Horse and especially Mike has been very positive and we recommend him to other business.
T.K.
Mike Connelly is an absolute superstar! My wife and I both own small businesses and work full time jobs. Our taxes can get pretty overwhelming fast. Mike helps us navigate the complexities we don't quite understand with ease and does so with a patient, friendly demeanor. We've been using him for almost a decade and would highly recommend his services, you won't be disappointed!
Troy D.
I've enjoyed working with Mike this past year and look forward to many great years ahead!
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