Evaluating PPLI, Investing in a Child’s Startup, and Cross-Border Tax Complexity

This week, we begin with a listener question about Private Placement Life Insurance. While the promise of tax-deferred growth and liquidity through policy loans can sound compelling, Stephan walks through the real tradeoffs: layered fees, insurance drag, liquidity constraints, and whether similar outcomes can be achieved more simply through traditional brokerage structures and securities-backed lending.

Next, we tackle a question many affluent families quietly face. A daughter launching a venture-backed tech startup has asked her parents to participate in a $250,000 seed round. Stephan explores how to separate parental support from investment discipline, why matching venture terms matters, how to avoid distorting the cap table, and how to protect family relationships if the business struggles.

In our From the Field segment, we are joined by Christine Concepción, an international tax attorney who advises globally mobile families and closely held businesses on cross-border structuring. The conversation covers tax residency rules, center of vital interest tests, entity restructuring when moving abroad, permanent establishment risks, PFIC traps, and why advance planning is critical before relocating or investing internationally. Christine also explains why it is often easier for foreign investors to structure investments in the U.S. than for U.S. citizens to invest abroad.

As families diversify not just portfolios but also residences, citizenships, and business interests, coordination across jurisdictions becomes essential. This episode offers a practical look at how to approach those decisions with clarity and discipline.

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Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principal. Past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor who can assess your individual financial situation, objectives, and risk tolerance. Thanks for listening!