Case study 1 

Real-Life Example: How the O’Sullivan family saved €500,000 in tax by planning early

The O’Sullivan family had run a successful food distribution business in Munster for over 30 years. Michael, the founder, was 62 and starting to think about retirement. His daughter, Aoife, had been working in the business for 10 years and was ready to take over.

But there were a few challenges:

• The company was valued at €2 million.
• Michael also owned the trading premises personally.
• Aoife had two siblings who weren’t involved in the business.
• No succession plan had been put in place.

They came to us for guidance.

Here’s what we did:

1. Company Restructure
   We restructured ownership so the business and property were held in a tax-efficient way, allowing for future transition without triggering immediate tax liabilities.
2. Retirement Relief
   Michael qualified for Capital Gains Tax Retirement Relief, which meant he could transfer shares in the business tax-free to Aoife.
3. Business Relief
   Aoife qualified for 90% Business Relief on her inheritance for CAT purposes. That reduced the taxable value of the shares from €2 million to €200,000, saving around €594,000 in potential tax (33% of €1.8 million).
4. Equalisation Plan
   We helped structure a fair way to provide non-business assets (like investment property) to the other siblings, so the family remained on good terms.
5. Phased Handover
   Over 2 years, Michael stepped back gradually, passing over leadership responsibilities while staying involved as an advisor.

The Result:

• The transition was smooth and well-communicated.
• The family avoided major tax liabilities.
• Aoife felt confident stepping into leadership.
• Michael retired knowing his legacy was in good hands.

Case study 2 – 

🧾 Case Study: The Roy Family’s Irish Succession – How a Tax & Legal Strategy Saved the Business from Implosion

Business: Waystar Royco (Ireland)
Industry: Media & Entertainment
Ownership: 100% held by Logan Roy
Location: Dublin, with offices in Cork and Galway
Annual Revenue: €120 million
Valuation: Estimated at €500 million

🏛️ Background

Logan Roy, the formidable patriarch of Waystar Royco Ireland, built a media empire from scratch. At 78, his health was faltering, but like many entrepreneurs, he refused to slow down or seriously discuss retirement.

He had four adult children, Kendall, Roman, Siobhan (Shiv) and Connor, all with varying levels of interest and involvement in the company. Logan controlled 100% of the shares, and there was no shareholder agreement, no formal succession plan and no tax strategy in place.

Tensions were high. Everyone wanted a piece of the empire, but nobody knew how it would play out if Logan passed suddenly. Sound familiar?

🚩The Problems (a classic Roy mess)

• Logan’s will was outdated, leaving the business in limbo.
• The company constitution didn’t specify what happens to shares on death or incapacity.
• No one had seriously considered Capital Acquisitions Tax (CAT)—which would be substantial.
• Logan owned both the business and several related properties personally, exposing the estate to a huge Capital Gains Tax (CGT) bill.
• The Roy kids were preparing for battle. Not board meetings.

🛠️ Our Succession & Tax Strategy (AKA: How to Avoid a Roy-Style Meltdown)

Here’s how we untangled the Roy family business using Irish law and tax planning:

1. Update the Will & Establish a Family Constitution

We worked with Logan to update his will in line with the Succession Act 1965, ensuring control passed according to his wishes—not intestacy rules.

We also helped the family draft a “family constitution”—a non-binding document outlining values, succession principles, and conflict resolution guidelines. It wasn’t legally required, but it got the siblings talking instead of suing.

2. Put a Shareholder Agreement in Place

Logan signed a formal shareholder agreement that:

• Defined how shares could be transferred.
• Put protections in place if one sibling sold out.
• Outlined voting rights and control if he became incapacitated.

This alone prevented multiple potential lawsuits (mostly from Kendall).

3. Capital Acquisitions Tax – Enter Business Relief

Without planning, each child could’ve faced a CAT bill of 33% on their share of Logan’s estate—devastating for a company of this size.

Instead, we structured a phased transfer of shares using Business Relief, reducing the taxable value of the business by 90%.

For example: Shiv’s inheritance of shares worth €10 million was valued at only €1 million for CAT—cutting her tax bill from €3.3m to €330k.

4. Capital Gains Tax – Leveraging Retirement Relief

Though Logan was over 66, we still managed to use CGT Retirement Relief, carefully navigating the reduced thresholds (max €500,000 post-66). By phasing the transfer and timing disposals, we minimised CGT exposure across multiple years.

5. Enduring Power of Attorney

Given Logan’s health, we established an Enduring Power of Attorney (EPA), appointing a trusted advisor (not Tom) to manage his business affairs if he lost mental capacity. This ensured continuity and protected the business from internal chaos.

✅The Outcome

• A €40+ million tax disaster was averted.
• A phased succession plan was implemented—Kendall and Shiv were brought into leadership with a mentoring phase.
• Roman found his niche in marketing (weirdly enough).
• Connor was given a family trust (and a vineyard).
• Logan retained influence without chaos.
• Waystar Royco remained privately held—and family-run.

🔍Key Takeaways

• Even media empires need structure.
• Start succession planning early. Logan left it way too late—don’t be like Logan.
• Irish tax reliefs can be game-changers if applied correctly.
• Clear agreements prevent war—especially when billions (and egos) are involved.

👨‍⚖️Thinking About Your Own Legacy?

You don’t have to be Logan Roy to face tricky questions about the future of your business. Whether it’s a retail chain, a family farm, or a tech startup—succession planning in Ireland needs smart legal, tax, and family-focused advice.

Let’s make sure your story ends better than the Roys’.