Can a Bond Help You Transfer Millions Tax-Free? In this episode of Sterling Insights, Roger sits down with Edward Condon, founder of Regatta Advisors and creator of Structured GRAT. Together, they explore how structured investments can be used within Grantor Retained Annuity Trusts (GRATs) to efficiently transfer wealth while minimizing gift taxes. Ed draws from his decades of experience in physics, finance, and structured product development to break down the mechanics and strategy behind this high-level planning tool. This episode is a must-listen for estate attorneys, financial advisors, and family offices looking to unlock the full potential of GRATs using custom-built structured note portfolios.
🎯 Key Takeaways:
💼 What Structured Notes Really Are: Structured notes are customized debt instruments that link returns to market indices, giving investors targeted exposure while offering downside protection.
🏛️ Why GRATs Work for the Ultra-Wealthy: GRATs enable the tax-free transfer of asset growth beyond a set hurdle rate—ideal for portfolios exceeding $25M.
🔄 How Custom Notes Enable Liquidity & Scalability: By tailoring notes to match annual GRAT payments, Ed’s team helps diversify credit risk and optimize for capital gains tax treatment.
🧠 Analytics Make or Break GRAT Success: Ed’s proprietary backtesting platform shows how different configurations can produce GRAT success rates above 95%.
🔍 Common Misconceptions Around Structured Products: Structured notes aren’t opaque hedge fund bets—they’re designed, collateralized, and executed for stability and transparency when done correctly.
💬 Quotes from Ed Condon:
"Structured notes let you customize the payoff profile to match the specific goals of the GRAT—it's not a one-size-fits-all approach."
"I realized you could unlock GRATs for liquid portfolios by designing illiquid-qualifying assets from scratch."
"The combination of customization, discountability, and predictable performance makes structured notes uniquely suited for wealth transfer."
🔗 Conclusion: If you work with ultra-high-net-worth families or are one, this episode shows how advanced analytics and tailored financial engineering can maximize legacy planning.
Connect with Ed:
Website: structuredgrat.com
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