// TAX PLANNING
Plan ahead.
Keep more of what you earn.
Taxes shouldn’t be something you think about once a year.
For business owners, the decisions that affect your tax position happen throughout the year — how the business is structured, when income and expenses are recognized, how owners are compensated, where capital is invested, and how major transactions are structured.
H2 Advisors combines proactive tax planning with comprehensive tax preparation and compliance to help business owners understand their tax position, identify planning opportunities, and make better-informed decisions before the year is over.
Because the best time to think about taxes is before the decisions are made.
// TAX PLANNING FOR BUSINESS OWNERS
Stop reacting to taxes. Start planning for them.
Tax preparation looks backward.
Tax planning looks forward.
By the time a tax return is being prepared, many of the decisions that could have affected the outcome have already been made.
That’s why H2 approaches tax as a year-round process.
We work with business owners throughout the year to understand expected income, evaluate changes in the business, model potential tax outcomes, and identify planning opportunities before important deadlines pass.
That might include evaluating the timing of income or expenses, considering equipment or capital investments, reviewing owner compensation, analyzing retirement plan contributions, assessing entity structure, or planning around a significant transaction.
The objective isn’t simply to prepare a return.
It’s to make tax strategy part of the financial decision-making process.
// YEAR-ROUND TAX STRATEGY
Tax planning shouldn’t start in December.
A lot can change over the course of a year.
Revenue grows. Margins change. New employees are hired. Equipment is purchased. Owners take distributions. New entities are formed. Acquisitions happen. Opportunities arise that weren’t part of the plan six months earlier.
Your tax strategy should evolve with the business.
Depending on the complexity of the engagement, our year-round tax planning may include:
- Quarterly tax planning meetings
- Income and tax projections
- Estimated tax planning
- Federal and state tax considerations
- Owner compensation analysis
- Retirement and benefit planning considerations
- Timing of income and deductible expenditures
- Capital expenditure and depreciation planning
- Multi-entity tax considerations
- Planning around significant business events
Rather than waiting until the return is prepared to see the result, proactive planning gives you an opportunity to understand potential tax consequences while there is still time to make informed decisions.
Fewer surprises. Better planning.
// TAX PREPARATION & COMPLIANCE
Preparation connected to the strategy.
Tax preparation still matters.
But we believe the return should reflect a tax strategy that has been considered throughout the year — not be the first time anyone seriously looks at your tax position.
H2 provides tax preparation and compliance services for privately held businesses, business owners, individuals, trusts, estates, nonprofit organizations, and other entities.
For business owners in particular, these filings rarely exist in isolation. The business return affects the individual return. Ownership structure can affect both. Estate and gift planning may intersect with business ownership.
Sales tax obligations can change as the company expands. A transaction can create tax consequences across multiple entities and taxpayers.
Our goal is to understand how the pieces fit together — not simply prepare each return in a vacuum.
BUSINESS TAX RETURNS
Tax preparation and compliance for privately held businesses and their owners, including:
- S Corporation Returns — Form 1120-S
- Partnership Returns — Form 1065
- C Corporation Returns — Form 1120
- Limited liability companies
- Sole proprietorships — Schedule C
- Federal and applicable state income tax returns
- Multi-state business income tax filings
- Estimated tax calculations and planning
INDIVIDUAL TAX RETURNS
Individual tax preparation with particular experience serving business owners and individuals with more complex tax situations, including:
- Individual Income Tax Returns — Form 1040
- Business owners and entrepreneurs
- Pass-through business income
- Investment activity
- Rental real estate
- Multi-state individual income tax filings
- Estimated tax calculations and planning
ESTATE, GIFT & TRUST RETURNS
Tax preparation and compliance for trusts, estates, and gift tax matters, including:
- Estate Tax Returns — Form 706
- Gift Tax Returns — Form 709
- Trust and Estate Income Tax Returns — Form 1041
- Fiduciary income tax filings
- Related estate, gift, and trust tax planning
When these matters involve broader estate or legal planning, H2 can work alongside the client’s estate planning attorney, financial advisor, and other professionals.
NONPROFIT & TAX-EXEMPT RETURNS
Tax preparation and compliance for nonprofit and tax-exempt organizations, including:
- Form 990 — Return of Organization Exempt From Income Tax
- Form 990-EZ
- Form 990-PF — Return of Private Foundation
- Form 990-T — Exempt Organization Business Income Tax Return, when applicable
- Applicable state tax and informational filings
SALES & USE TAX
As businesses expand into new states, sell through new channels, or cross economic nexus thresholds, sales and use tax obligations can become increasingly complex.
H2 helps businesses evaluate potential filing obligations, understand taxability considerations, and manage ongoing sales and use tax compliance.
Our services can include:
- Sales and use tax return preparation and filing
- State and local sales tax compliance
- Sales tax registrations
- Economic and physical nexus analysis
- Multi-state sales tax considerations
- Product and service taxability analysis
- Exemption and resale certificate considerations
- Use tax considerations
- Sales tax exposure analysis
- Support with sales tax notices and correspondence
OTHER TAX FILINGS
Depending on the needs of the client, H2 can also assist with:
- Florida Tangible Personal Property Tax Returns
- Business property tax filings
- Foreign account and information reporting, when applicable
- Other federal, state, and local tax filings within the scope of our tax practice
For clients who also use H2’s Accounting or Fractional CFO services, tax preparation can connect directly to the financial information and planning already taking place throughout the year.
// ENTITY STRUCTURING
Your business structure should evolve with your business.
The way a business is structured can have meaningful tax consequences.
But the structure that made sense when you started the company may not be the structure that makes sense today.
As revenue, profitability, ownership, and complexity change, we help business owners evaluate whether their current entity and tax elections continue to support their objectives.
That may include analyzing:
- LLC taxation
- S Corporation elections
- C Corporation considerations
- Partnership structures
- Owner compensation
- Multi-entity structures
- Holding companies
- Intercompany relationships
- New acquisitions or business lines
- Ownership changes
We can model different tax scenarios and help you understand the potential implications to both the business and its owners.
When legal restructuring is appropriate, we can coordinate with your attorney and other advisors while H2 focuses on the tax and financial considerations.
The goal isn’t complexity for the sake of complexity. It’s a structure that makes sense for the business you’ve built — and the one you’re building toward.
// TRANSACTION TAX PLANNING
The headline price isn’t the only number that matters.
Buying or selling a business creates tax questions that can materially affect the economics of a transaction.
- Asset sale or equity sale?
- How will the purchase price be allocated?
- How will different components of the consideration be taxed?
- What are the implications of seller financing or contingent consideration?
- How could the transaction affect the owner’s overall tax position?
These questions are best evaluated before the transaction documents are finalized — not after the deal closes.
H2’s tax team works alongside owners and transaction advisors to help evaluate the tax consequences of potential deal structures and identify issues that should be considered during negotiations.
Our transaction tax planning can include:
- Asset versus equity transaction analysis
- Purchase price allocation considerations
- Installment sale considerations
- Tax modeling of transaction proceeds
- Entity restructuring considerations
- Acquisition tax planning
- Owner-level tax considerations
- Pre-transaction tax planning
- Coordination with legal and M&A advisors
And because H2 also provides Business Valuation and M&A Advisory services, our tax professionals understand the broader transaction process and can coordinate with the professionals working on the other pieces of the deal.
What you sell for matters. What you ultimately keep matters too.
// WHY H2 ADVISORS
Tax advice connected
to the bigger picture.
Plan before the year is over.
Tax decisions are more useful when there is still time to act. Our planning process is designed to identify issues and opportunities throughout the year rather than only during filing season.
Business and owner decisions are connected.
For privately held businesses, the company’s tax position and the owner’s financial decisions are often closely linked. We consider both when evaluating planning opportunities.
Accounting + Tax + Fractional CFO
Tax planning is stronger when it starts with a clear understanding of what is actually happening in the business.
H2’s Accounting, Tax, and Fractional CFO teams can work from the same financial information, creating better coordination across reporting, planning, and strategy.
Tax is one factor in a bigger decision.
The lowest-tax option isn’t automatically the best business decision.
We consider tax alongside cash flow, capital needs, growth plans, owner objectives, and the longer-term direction of the business.
Planning beyond the annual return.
Our Business Valuation and M&A experience gives our tax team a broader perspective when owners are considering acquisitions, recapitalizations, ownership changes, or a future sale.
Advice that reflects how owners actually make decisions.
For business owners, company strategy, personal cash flow, taxes, wealth creation, and eventual exit planning are often interconnected. Our approach recognizes that.
// ONE FIRM. EVERY STAGE OF THE BUSINESS.
Tax strategy shouldn’t exist in isolation.
Most advisors see one piece of your business.
H2 brings Accounting, Tax, Fractional CFO, Business Valuation, and M&A Advisory together — connecting the financial and tax decisions you make today with where you want the business to go tomorrow.
Tax sits at the foundation of that process, influencing everything from current cash flow and entity structure to capital allocation and the economics of a future transaction.
Accounting + Tax
Build the financial foundation.
Fractional CFO
Turn information into action.
Business Valuation
Understand and build value.
M&A Advisory
Realize what you’ve built.
One firm. Every stage of the business.
// FREQUENTLY ASKED
Answers to the questions
we hear most.
// LET'S TALK
Make tax planning
part of the strategy.
Move beyond once-a-year tax preparation with proactive planning built around your business, your goals, and what comes next.