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Stephan ShipeStephan Shipe
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Supporting Your Child’s Startup: Navigating Terms, Risk, and Family Dynamics

Mar 5, 2026

For families who find themselves in the exciting but fraught position of being asked to back a child’s venture-backed startup,...

Private Placement Life Insurance: Evaluating the Benefits and Drawbacks

Mar 5, 2026

What Private Placement Life Insurance Promises Private placement life insurance (PPLI) is marketed as a type of permanent life insurance...

Short-Term Rentals and Bonus Depreciation: What Actually Qualifies

Feb 26, 2026

Start With the Investment Itself Before we talk about bonus depreciation or any tax strategy tied to short-term rentals, I...

When One Child Opts Out: Keeping Family Gifting Fair

Feb 25, 2026

A family recently came to me with an situation that felt awkward on the surface but points to something much...

Australian Super Funds and US Taxes: What Expats Need to Know

Feb 20, 2026

If you’re a dual US-Australian citizen living permanently in the United States with money in Australian super funds, you need...

How to Evaluate a $750k Oil Well Investment Opportunity

Feb 18, 2026

I recently received a question from a listener who sold a portion of their business and now has about $12...

Family Office Strategy: Outsourcing vs. Hiring for Long-Term Growth

Feb 12, 2026

When you’re in the early stages of building out a family office, it’s tempting to move quickly. But one of...

A Neurosurgeon Navigating Rising Wealth and Rising Risk

Feb 6, 2026

I recently heard from a neurosurgeon with roughly nine to ten million dollars spread across investments, retirement accounts, and ownership...

Inheriting Multiple Properties: When to Hold, Sell, or Restructure

Feb 6, 2026

When you inherit real estate after a parent passes, it can feel like a weight drops onto your shoulders overnight....

Wash Sales in Complex Portfolios: What Investors Miss

Feb 5, 2026

When portfolios get large and spread across multiple accounts, custodians, and reinvestment systems, tax loss harvesting becomes more complicated than...

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