Episode 405: Reducing Lifetime Tax Drag for Business Owners with Omar Morillo

About this episode

Omar Morillo discusses strategies for reducing lifetime tax drag for business owners in preparation for liquidity events.

When Omar Morillo talks about wealth management for entrepreneurs, he focuses on one core idea: reducing lifetime tax drag across income, investments, business operations, and eventual liquidity events. The earlier owners start planning, the more options they have. In this episode of the DealQuest Podcast, Corey Kupfer sits down with Omar Morillo, founder of Imperio Wealth Advisors, to discuss what sophisticated pre-exit planning actually looks like for business owners preparing for major liquidity events. Omar breaks down the three levels of tax-aware investing, from simple ETF investing to direct indexing and long-short strategies designed to generate capital loss carryforwards for future gains. He explains why many of the best planning opportunities disappear once an LOI is on the table and why advanced preparation matters. The conversation also explores estate planning, donor advised funds, PPLI structures, and the risks of “flavor-of-the-month” tax strategies that are often oversold to entrepreneurs. Corey and Omar also discuss the emotional side of exits, including why many founders struggle with identity and anxiety after selling the business that defined their lives for…

People in this episode

Host: Corey Kupfer

Guest: Omar Morillo

Topics covered

• wealth management
• tax planning
• business operations
• liquidity events
• estate planning
• investing strategies

Keywords

• tax drag
• wealth management
• entrepreneurs
• pre-exit planning
• capital loss carryforwards
• estate planning
• donor advised funds

Mentioned in this episode

Organizations: Imperio Wealth Advisors

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