Welcome back to The Entrepreneur’s Journey. In this episode, Jason Gabrieli sits down with John Cavanaugh, CPA and tax attorney at Firenze Advisors, to discuss the foundational role that legal entity structure plays throughout the life of a business—from launch to scale to exit. They explore common pitfalls, how to adjust structures as businesses grow, and key planning considerations for exits, succession, and estate transitions. If you’re a business owner thinking about growth or preparing for a future sale, this episode is packed with practical knowledge.

Tune into this episode to also learn:

• Why your legal entity structure isn’t just paperwork—but the core of your business.
• How and when to shift from LLC to S-Corp or C-Corp status.
• The role of installment sales, trust planning, and QSBS in reducing tax liability.
• What business owners often overlook when preparing for a sale or succession.

What we discussed

• [00:01:36] Why entity structure is foundational—and what most owners overlook.
• [00:03:16] How and why business structures should evolve over time.
• [00:05:06] The niche John fills: strategic planning across legal and tax.
• [00:06:54] Real estate and multi-entity structures: liability and tax traps to avoid.
• [00:09:01] Debt, partners, and why cross-collateralization needs careful planning.
• [00:10:40] Transitioning a business: selling to outsiders vs. keeping it in the family.
• [00:13:03] What surprises owners during due diligence and how to be prepared.
• [00:16:45] Why planning ahead matters: using trusts and state residency smartly.
• [00:18:11] Charitable trust and life insurance planning to reduce estate tax.
• [00:20:31] Holding company structures: when and why to consider one.
• [00:24:31] What clients usually miss: books, documentation, and cleanup.
• [00:26:24] Installment sale example that saved significant taxes.
• [00:30:07] Managing wealth post-sale and preserving it for future generations.
• [00:32:06] The power of looking at your structure every 2–3 years.

3 Things To Remember

1. Your legal and tax entity structure should evolve as your business grows.
2. Planning for sale or succession starts years in advance—don’t wait.
3. Holding companies, trusts, and installment strategies can drastically reduce taxes and protect assets.

Memorable moments:

(00:01:36) “Your legal entity structure isn’t just paperwork. It’s the foundation of your business.”

(00:14:10) “No one really tracks their basis, they just think, ‘I started this from scratch.'”

(00:26:24) “Instead of taking that 50% tax hit on day one, you can spread it out with an installment sale.”

Useful Links

Connect with Jason Gabrieli: jgabrieli@HFMadvisors.com | LinkedIn

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