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Our Services

CPA Services for Real Estate Investors and Business Owners

The Tax Boss provides CPA services for real estate investors and business owners earning $400K or more: year round tax planning, tax preparation, and bookkeeping. Ana Klein, CPA, and her team work 100% virtually, so you get the same dedicated advisor wherever you live.

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  • 4.7Google rating across 35 reviews
  • 118KInvestors and owners follow Ana on Instagram
  • 100%Virtual, with clients across the United States

How They Fit Together

Clean Books Lead to a Better Plan and a Better Return

Each service feeds the next one. Accurate books give your advisor real numbers to plan with, and the plan shapes the return we file.

  1. Bookkeeping

    Your income and expenses are tracked and categorized throughout the year, for your business and your rentals.

  2. Tax Planning

    Your advisor uses those numbers to choose strategies before the year ends, while they can still change your tax bill.

  3. Tax Preparation

    We file a return that reflects the plan, then walk you through it on video so you know what changed and why.

Choose Your Service

Three Services, One Dedicated Advisor

Use one service or combine them. Your free discovery call is where we work out the right mix for you.

Our core service

Tax Planning

Best suited for high earners making $400K or more a year

Year round, proactive tax strategy that legally lowers what you owe, built around your properties, your businesses, and your goals.

  • A personal strategy from your dedicated tax advisor
  • Real estate portfolio structuring that keeps your DTI bankable
  • Cost segregation study coordination
  • Short term rental tax strategy
  • Entity structure review
  • Year end tax projection
  • Live group strategy calls with Ana

Starting at$8,497

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Filing season and beyond

Tax Preparation

Best suited for business owners

Personal and business returns prepared and filed by our team, including multi entity and rental property filings.

  • Personal and business returns
  • Multi entity filings for LLCs, S corps, and partnerships
  • Rental property returns
  • Asset sale tax analysis
  • Amended returns and prior year corrections
  • A personal video walkthrough of your completed return

Starting at$3,000

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The foundation

Bookkeeping

Best suited for business owners

We set up your accounting and keep it current, so your records are ready when it is time to plan and file.

  • Accounting setup for your business and rentals
  • Ongoing expense tracking and categorization
  • Organized financials across your properties and entities
  • Records ready for tax planning and preparation

Starting at$550/month

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What Working With Us Looks Like

A Tax Strategist on Your Side All Year

One advisor, no handoffs

You work with the same dedicated tax advisor from your first call onward. They know your properties, your entities, and your goals.

Planning all year, not just in April

We review your situation through the year, so strategies are in place before December 31 instead of discovered after it.

100% virtual, anywhere in the US

Calls, documents, and strategy sessions all run on one secure platform, so where you live never limits who you can work with.

You see the reasoning

Every completed return comes with a personal video that explains your numbers, so you understand your taxes instead of just signing them.

Where We Go Deep

Real Estate Tax Strategies We Specialize In

  • Cost segregation studies
  • Bonus depreciation
  • Short term rentals on Airbnb and VRBO
  • Real Estate Professional Status
  • Rental portfolio structuring
  • LLC and S corp entity structure
  • Multi entity filings
  • Asset sale planning
  • Amended and prior year returns

Is This a Fit?

Built for Investors and Owners Ready to Plan Ahead

We are a strong fit if you

  • Earn $400K or more in annual income or business revenue
  • Own rentals, short term rentals, or a growing real estate portfolio
  • Run one or more businesses, LLCs, or S corps
  • Want a year round tax strategy instead of a once a year filing

Not there yet?

Start learning the rules now. Ana teaches them for free, and the strategies are waiting for you when your income grows.

Join the free tax community on Skool Get the free REPS guide

Questions

Services FAQ

Anything else, bring it to your free discovery call.

What is the difference between tax planning and tax preparation?

Tax preparation reports what already happened in a tax year and files your return. Tax planning happens before the year ends and decides which strategies to put in place, such as cost segregation, entity changes, or short term rental rules, so your tax bill is lower when the return is prepared.

Do I need bookkeeping before tax planning?

Tax planning depends on accurate numbers. If your books are current and reliable, we can plan from them. If they are behind or messy, we start with bookkeeping so your strategy is built on real figures.

How much do your services cost?

Tax planning starts at $8,497, tax preparation starts at $3,000, and bookkeeping starts at $550 per month. Your exact quote depends on how many entities and properties you have, and we confirm it after your free discovery call.

Do you work with clients outside Wisconsin?

Yes. The Tax Boss is a 100% virtual CPA firm, and we serve clients across the United States.

Who is a good fit for The Tax Boss?

Real estate investors and business owners earning $400K or more who want a proactive, year round tax strategy. If you are not at that level yet, our free tax community on Skool is the best place to start.

Find Out What You Could Keep

On a free discovery call, we review your income, your properties, and your current approach, then tell you which service fits and what it would cost.

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