News and Updates

September 21, 2026

Selling Your Business Beyond the Earnout, Family Loans and the IRS, Counterfeit Wine

Transcript Intro Stephan Shipe: Welcome back to the Scholar Wealth Podcast. This week we begin with a listener considering selling his business who heard our earnout question a few weeks […]

September 14, 2026

Cash Balance Plans for High-Earning Physicians, Building a System for Lumpy Income, and Trust Provisions for Adult Kids

Transcript Intro Stephan Shipe: Welcome back to the Scholar Wealth Podcast. This week we begin with an anesthesiologist doing locums through an S-corp who already maxes a solo 401(k) and […]

September 7, 2026

The Executor Trap, the Machine Age Fund, and Handbags as an Asset Class

Transcript Intro Stephan Shipe: Welcome back to the Scholar Wealth Podcast. This week we start with a listener who was asked to serve as executor of a close friend’s estate […]

August 31, 2026

The Uninterested Heir, Earnout Reality Check, and Hiring a Nanny

Transcript Intro Stephan Shipe: Welcome back to the Scholar Wealth Podcast. Today we have a question from a self-managed investor asking whether to steer his adult son toward a wealth […]

August 24, 2026

Custom Suits, Bulletproof Jackets, and the $45,000 Vicuña with Anthony Bolognese, Capitol Hill Clothiers

Transcript Intro Stephan Shipe: This week, we’re dedicating the full episode to a conversation I had with Anthony Bolognese, founder of Capitol Hill Clothiers. Anthony is a custom clothier based […]

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