From reacting to tax bills every year
Stop Overpaying $15K–$30K/Year in Taxes
Most founders and business owners don’t realize how much money they lose through reactive planning, outdated entity structures, and missed tax strategies until it’s already too late.
We help entrepreneurs, real estate investors, and startups reduce unnecessary taxes through proactive strategy and implementation.
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250%+
Average Client ROI
15+
Years Experience
#1
Tax Strategist In The US
(2023)
The Problem
You’re building a successful business, but your tax strategy hasn’t caught up.
You’re generating revenue and creating wealth, yet your tax bill keeps growing — often because important decisions are made too late in the process.
Many entrepreneurs miss valuable tax-saving opportunities not because they lack revenue, but because the right strategies, structures, and planning weren’t implemented early enough.
By the time many founders realize the problem, the transaction has already happened, and the biggest opportunities are gone.
Instead of proactively structuring their finances, they’re reacting to tax bills that could have been reduced or avoided with the right planning.
What if instead, you could transform...
From realizing opportunities too late
From guessing whether your structure is
actually optimized
To...
To having a clear tax strategy that evolves
with your business
To making financial decisions with tax efficiency built in
To working with advisors who proactively plan years ahead
To finally feeling confident that your financial strategy is aligned with your long-term goals.
Hear from founders and investors who’ve transformed their financial strategy
“Working with Anomaly has honestly changed our lives. We went from constantly worrying and feeling overwhelmed to finally feeling organized, supported, and confident about our business.”
Ben Billups
“If you're an entrepreneur, business owner, or high earner with investments like real estate, working with Greg and the team is an absolute no-brainer. They’re forward-thinking leaders in the space, and they’ve personally saved me far more money than they’ve cost.”
Strategic Tax Planning Built Around Long-Term Growth
Strategic Tax Planning
Identify missed tax-saving opportunities before they become expensive mistakes.
Advanced Structuring
Optimize your entity structure and financial setup to reduce unnecessary taxes over time.
Proactive Planning
Plan ahead year-round so major financial decisions aren’t made too late.
Transaction Strategy
Structure the deal before taxes become unavoidable.
Ongoing Advisory
Continue refining your strategy to support long-term growth as your business and investments evolve.
How Our Process Works
1
Discover
We start by analyzing your business, investments, entity structure, and financial picture to uncover opportunities that may be costing you money.
2
Plan
Our team builds a tailored tax strategy designed around your business, goals, and long-term growth plans.
3
Implement
We don’t stop at recommendations. Through ongoing support and regular check-ins, we help execute and evolve your strategy over time.
TESTIMONIALS
What our clients say
about us
Brian Megill | Host Events Inc.
"Anomaly, has been INSTRUMENTAL to the success of our start-up business. Their knowledge, expertise, and due diligence in the accounting field gives us the confidence that our books will always be in good hands as we continue to focus on other pertinent business matters. I would recommend Anomaly to anyone looking for a fantastic service on a budget! Thank you for being awesome!"
C.Kay International
I discovered them through some research on Google, actually.
I had just moved to Massachusetts, and I needed a Massachusetts accountant, somebody to come and partner with me.
I’ve been using them for about two years now.
They are great partners.
They really support me in my business, and I highly recommend them.
I feel they can support any industry with all their accounting and tax needs.
Dan Bresciani
"I would recommend Anomaly to anyone. They have been an extremely valuable asset to our business and acts as an extension of our team. We began working with Anomaly almost 2 years ago and it was a great decision. They are extremely responsive and I would highly recommend their services to anyone."
Jay Carlington
"Anomaly provides a professional and tailored approach to achieve the desired outcome for clients and we couldn’t be happier with the quality of his services. They've helped us manage through the first year of our new company and taken the stress out of dealing with multiple vendors, agencies and tax authorities making year one seamless for our business. We look forward to another successful year and would highly recommend their services!"
John Guilfoil Public Relations
I would wholeheartedly recommend Greg O’Brien and his entire team to any small business or mid-sized business owner looking for help.
We don’t have the resources, and often don’t have the budgets, to bring on staff full-time.
Honestly, Greg and his team have been the next best thing.
Mark Perlberg
"Anomaly helped me out with starting my own business. I could tell right away that they were extremely knowledgeable and passionate about helping their clients navigate the complex world of taxes and creating effective strategies to reach their goals."
Nexus Family Chiropractic
The biggest difference that we noticed right away was that there were all these things that we could be taking advantage of.
We could be way more strategic with how we were filing, what strategies we had in place, and what things had been ruled on from a tax law perspective.
My favorite part about it is, at the highest level— because there are tiers that you can work with the team through— but at the highest level, you’re fully supported.
Your accounting is taken care of. All of your tax strategy is taken care of. Basically anything you would need on the back end, money-wise, you’re taken care of.
That even includes if an audit were to come up or something like that. You have support with all of that. Love it. So grateful.
Wade Critides | Lifestyle Entrepreneur
I’ve been a client since day one, and I’m just so proud of him, seeing him build this up.
Now he’s helping so many people— so many entrepreneurs, so many businesses, so many investors, so many individuals and companies. It’s been incredible.
I’ve been working with him and his team for, yeah, must be four years now. And I would say, if you’re an entrepreneur, you own businesses, or you’re a high earner and you have investments like real estate, working with Greg is an absolute no-brainer.
They’re forward-thinking.
They’re cutting-edge.
They’re leaders in the space.
I know personally, for me, they’ve saved me a lot of money, which has been able to add to my net worth.
I’ve saved way more than they’ve cost, or the investment in them.And it’s so worth it. So much so.I’ve recommended dozens of people to them.
Building Smarter Financial Strategy, Not Just Filing Returns
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Anomaly works with founders, real estate investors, and growing businesses that want to stop making tax decisions too late.
Our team helps clients reduce unnecessary taxes through proactive planning, entity structuring, transaction strategy, and long-term implementation support.
Instead of treating taxes as a once-a-year event, we help clients build strategies that evolve as their business, investments, and financial goals grow.
Solutions designed for growing businesses and investors
Strategic Tax Planning
Reduce unnecessary taxes through proactive year-round planning instead of reactive filing at tax season.
Business & Entity Structuring
Optimize how your business and investments are structured to improve long-term tax efficiency.
Advanced Planning
Navigate major financial decisions, liquidity events, and complex transactions before opportunities are missed.
FAQs
Common Questions About Strategic Tax Planning
Why shouldn’t I just work with a traditional CPA?
Most traditional CPAs focus on compliance — filing returns accurately after decisions have already been made.
Our focus is proactive tax strategy. We help founders structure businesses, investments, and major financial decisions before missed opportunities become expensive.
Do you only work with high-net-worth clients?
Not at all. We primarily work with founders, business owners, real estate investors, and growing companies that need more proactive tax planning as complexity increases.
Many clients come to us when revenue is growing, entities are expanding, or larger financial decisions start carrying bigger tax consequences.
How early should tax planning begin?
The earlier, the better.
Many of the most valuable tax strategies must be implemented before a major transaction happens — such as selling a business, liquidating stock, or restructuring ownership.
By tax season, many opportunities are already gone.
What types of strategies do you typically help with?
Our work often includes:
- Business and entity structuring
- Capital gains planning
- Real estate tax strategy
- Startup and investor planning
- Transaction structuring
- Proactive year-round tax planning
The goal is to reduce unnecessary taxes while supporting long-term business growth.
What if I already have a CPA?
That’s completely fine.
Many clients continue working with their existing CPA or accounting team while we focus on proactive planning, strategy, and larger financial decisions.
In many cases, we work alongside existing advisors to help implement more advanced tax strategies.