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Greg O'Brien, CPA

Anomaly CPA | 2x 40 Under 40 | 2024 Forbes Top 200 CPA

Greg O'Brien is the Co-CEO and co-founder of Anomaly CPA, a virtual accounting firm specializing in complex tax planning and advisory services for entrepreneurs, startups, and small businesses.12 He founded the company in 2018 with a vision to scale a fully remote firm working with innovative and high-growth businesses.3

Professional Background

Greg holds a Bachelor of Science in Accounting and a Master's Degree in Taxation from Bentley University.1 He is a licensed Certified Public Accountant (CPA) in Massachusetts and a Certified Tax Strategist (CTS).13

Expertise and Recognition

Greg specializes in:

  • Advanced tax planning
  • Business advisory services
  • Short-term rental taxation

His expertise has earned him several accolades:

  • Named #1 Tax Strategist in the United States by the AICTC in 202312
  • Top 5 National Finalist for Tax Planner of the Year by the AICTC in 20201
  • "40 Under 40" honoree in the accounting profession3

Company Growth

Under Greg's leadership, Anomaly CPA has experienced significant growth:

  • Ranked #1186 on the Inc5000 list2
  • Surpassed 30 team members as of July 20244

Personal Interests

Outside of work, Greg is described as an avid Boston sports fan, CrossFit enthusiast, and podcast enthusiast.1 He values entrepreneurship and enjoys studying successful entrepreneurs across various industries.

Highlights

Sep 3 · linkedin

The IRS cannot change the law and taxpayers with resources continue to challenge them when they overstep...

The IRS once again lost a case where they went directly against Congress. Although there was a flaw or "loophole" in the law, IRS cannot unilaterally change the law, without Congressional action.

Varian Medical Systems was audited over a foreign tax issue but challenged the IRS over their interpretation. The court rules 12-0 in favor of Varian and the "Tax Court held that it would not defer to a Treasury Regulation to the contrary because it exceeded Treasury's delegated rulemaking authority."

This is just one of many recent examples where the courts have sent a clear message that the IRS cannot exceed their power and changes in law belong with Congress, not a government agency.

Aug 30 · linkedin

No surprise here...the wealthiest donors are pushing VP Harris to drop the proposal to tax unrealized gains...

The controversial proposal, to start, would only affect the ultra wealthy. It would also be challenged very quickly and end up in the Supreme Court.

My opinion is this is unlikely to ever pass in Congress but wealthy corporate donors have been shaken by this and according to the New York Times, they have begun to quietly ask Harris to drop the proposal...

Taking a step back, it is a highly problematic proposal to practically implement.

Yesterday's news that Treasury can't figure out how to actually implement the "$400k and under" audit promise should be a hint...

Related Questions

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Greg O'Brien, CPA
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Location

Boston, Massachusetts, United States