Greg O'Brien, CPA

Greg O'Brien, CPA

Co-CEO, Anomaly

Greg co-founded Anomaly CPA with John Malone, JD to specialize in working with entrepreneurial clients who own startups, high growth small businesses, and real estate investors growing into more complex tax and financial issues. His experience includes advanced tax planning and business advisory for a wide array of individuals, start ups and real estate investors. In 2020, Greg was named a Top 5 National Finalist for the Tax Planner of the Year by the AICTC, from a pool of over 850 qualified Tax Planners from across the US and Greg was named the #1 Tax Strategist in the United States by the AICTC in 2023. Greg was a 2023 and 2022 40 Under 40 and has helped lead Anomaly to the #1186 ranking on Inc. 5000 list.

Education

Bentley University, BS Accounting and Master of Science, Taxation

Expertise

Taxation; Startup Financing; Startup Accounting

Highlight

2023 & 2022 40U40 & 2023 Certified Tax Strategist of the Year

If you’d like to explore more ways to grow your businesses financial operations and tax strategies, connect with us at anomalycpa.com/connect.

Articles by Greg O'Brien, CPA

7 common small business accounting mistakes to avoid
7 common small business accounting mistakes to avoid
Discover 7 common accounting mistakes startups and small businesses should avoid to reduce risk, stay compliant, and improve financial decision-making.
ADA tax credit: A little-known tax credit for small businesses
ADA tax credit: A little-known tax credit for small businesses
Learn how to claim ADA tax credits for digital accessibility improvements, stay compliant with the Americans with Disabilities Act, and reduce costs.
Leveraging the work opportunity tax credit in your business
Leveraging the work opportunity tax credit in your business
Learn how the Work Opportunity Tax Credit (WOTC) benefits businesses. Get step-by-step guidance on eligibility, certification, and claiming your tax credit.
IRC 45s: Employer tax credit for paid family and medical leave
IRC 45s: Employer tax credit for paid family and medical leave
IRC 45S provides a tax credit to employers who offer paid family and medical leave to their employees. Learn more about how to use it.
How R&D tax credits can fund your business in 2025
How R&D tax credits can fund your business in 2025
In this article, we delve into the lucrative R&D tax credit and how it can fund your business.
An overlooked tax credit for startups: empowerment zone tax credits
An overlooked tax credit for startups: empowerment zone tax credits
Unlock the benefits of the Empowerment Zone Tax Credit to enhance your business's financial health while contributing to community revitalization. Learn about its legislative history, eligibility criteria, and step-by-step guidance on claiming and quantifying the credit. Explore do's and don'ts, and get answers to frequently asked questions to maximize your tax savings effectively.