Publication date: 04.04.2025
Basil Chochla is a Certified Public Accountant (CPA) and tax advisor based in the US. Founder of The Bee Dance CPAs. He specializes in tax planning, small business accounting, financial consulting, and international taxation for entrepreneurs and investors.
Tax Structuring and Planning for a $100M Family Conglomerate
Tax structuring and planning is one of the most critical services for high-net-worth families, multi-entity enterprises, and international corporate groups. Between 2018 and 2020, I had the privilege of working with a $100 million family conglomerate operating across 30+ legal entities and industries—ranging from healthcare and real estate to hospitality, assisted living, investment firms, and even a Cayman Islands-based captive entity.
This case illustrates the real-world implementation of comprehensive tax planning and structuring at the enterprise level, including IRS negotiations, penalty abatements, capital gains optimization, M&A tax due diligence, and re-investment strategies through Opportunity Zones. Our goal was to protect capital, increase tax efficiency, and support long-term business scalability.
Key Outcomes Achieved
- Resolved outstanding tax compliance across multiple entities
- Avoided millions in penalties through strategic abatement
- Structured and supported the sale of Agape Hospice in SC
- Optimized capital gains from a $150M real estate transaction
- Reinvested proceeds through Opportunity Zones for tax deferral
- Secured millions in COVID-related funding and tax credits
- Built internal financial literacy programs using Color Accounting™
Step-by-Step Implementation
- Entity Analysis and Corporate Mapping:
Mapped out 30+ interrelated entities across healthcare, real estate, management, and finance to uncover inefficiencies and compliance risks. - Tax Return Recovery and Penalty Abatement (2015–2017):
Worked with the CFO to file overdue returns and successfully negotiate with the IRS for penalty waivers due to mitigating circumstances. - M&A Structuring – Agape Hospice Sale:
Oversaw financial due diligence and tax structuring of one of South Carolina’s largest in-patient hospice equity transactions. - Capital Gains Planning – $150M Deal:
Managed optimization of capital gains from a major real estate divestiture involving 13 assisted living facilities. Designed reinvestment plan using Opportunity Zones. - COVID-Era Financing & Tax Credits:
Applied for and secured millions in COVID relief funding. Partnered with legal teams to claim state and federal rehabilitation and historic tax credits. - Financial Literacy for Executives:
Led internal training with Color Accounting™ to improve financial decision-making across operational teams and enhance reporting accuracy. - Corporate Development Participation:
Sat on the culture and org development committee to streamline job descriptions, improve role clarity, and align business units with growth goals.
Areas of Expertise Applied
Advanced Tax Structuring
Built compliant structures to reduce liability across multi-entity, multi-state, and international operations
M&A Due Diligence & Execution
Managed end-to-end tax and financial due diligence for high-value transactions in healthcare and real estate
International Entity Management
Provided legal tax coordination for the Cayman Islands-based entity, ensuring CFC compliance and tax minimization
Frequently Asked Questions
Question
How do Opportunity Zones help reduce taxes?
Answer
Opportunity Zones allow reinvestment of capital gains into designated development areas. In this case, the client reinvested a significant portion of their $150M proceeds, deferring and in some cases eliminating long-term capital gains taxes.
Question
Can large penalties be avoided for unfiled returns?
Answer
Yes. With strong supporting documentation and a proactive filing strategy, we successfully abated IRS penalties for three years of missing filings—saving the group millions in liabilities.
This case exemplifies how tax structuring and planning are not just about compliance—they’re about empowering growth, protecting capital, and creating financial leverage for high-value business groups. Our work resulted in:
Significant tax savings through legal structuring
Efficient handling of over 30 operational entities
Optimized exit strategies for high-value assets
Strengthened internal financial infrastructure
Future-proofing the conglomerate for expansion
For family offices, investment groups, and cross-border enterprises, working with a specialist in corporate tax planning means transforming challenges into growth strategies. This project stands as a model for effective collaboration between accounting, law, and strategy at scale.
