Tax Planning & Representation


There are a variety of opportunities to efficiently structure business and investments, but we haven’t found one that is right for everyone. Bespoke tailoring for your tax and estate planning.


COVD-19 Tax Relief and Business Stimulus

There’s a lot to dive into where small business stimulus relief is concerned. You can rest a little easier knowing that you can rely on one of our our certified tax pros to help make sense of it all.

Bitcoin and Cryptocurrency Reporting

If you have been contacted by the IRS about Cryptocurrency reporting, get professional advice before you respond.

Corporate Formations & Tax Structuring

This is complex. If you don’t believe us, run a Google search for “Whats the best business type for me” and see how much conflicting and inaccurate feedback is returned. Our guidance is a function of deep technical knowledge of IRS regulation and state law and practical, real world experience.

IRS and Mass. Dept. of Revenue Audits

We represent clients under power of attorney to obtain tax transcript details, formally document taxpayer assets, liabilities and average monthly income and expenses enabling best-possible resolution in an efficient manner.

Return Preparation & E-File

Everything we do in this Income tax and private wealth service line boils down to a tax return and filing deadlines. It’s the least glamorous, but where all the planning comes to a point. Psst… we actually enjoy preparing tax returns and we’re as good as it gets.

Federal & State Compliance

The IRS is just one kid on the block – certainly the biggest and baddest on the block – but still just one. Each state has a Dept. of Revenue with obscure nuances and these are critical for payroll, unemployment and income tax compliance.



A financial advisory firm that works at the intersection of finance and technology. Most finance professionals aren’t technologists and most technologists don’t understand the day to day objectives of today’s finance departments – that’s where we come in.

Woman in business meeting


Chad is an A player who works smart and hard to produce the best results of himself and everyone around him. He’s a pleasure to work with and see excellent things for Cloud9’s future!! A++

Mark Eliot

I've worked with the folks at Cloud9 Advisory for over 3 years now and I've always been very impressed by the suite of services they offer my business. They're always available, very friendly and most importantly they know their stuff. Very satisfied.

William DeVitoFounder & CEO CRMD, Inc.

I called Cloud9 Advisory to reconcile my books for the year and to set them up so they are streamlined moving forward. They did everything I asked and more. They added their own thoughts/advice/practices which were things I wasn’t even thinking about and were extremely knowledgeable in regard to taxes in many different areas of business. Easy to work with and A+ advice and guidance. Highly recommend.

Jon LawlessOwner, Vault Properties

Cloud9 has been a trusted advisor for my small business since 2016. Most recently, C9 helped evaluate the impact of recent tax reform (Tax Cuts and Jobs Act) on my company’s projected operations, including the corporate tax rate reduction and pass-through reforms. C9 provided me with insight and analysis tailored to my operating plans, and allowed me to make an educated decision on tax elections and other operating strategies going-forward. C9’s advisory has been instrumental in our planning for key business decisions in 2020 and beyond.

Working with C9 is a refreshing experience. I would recommend them to any business owner looking to strategically navigate any complex business decisions.

Brian HarrahyPresident, FHA Preservation Group