News and Updates

August 26, 2026

Private Credit as a Diversifier: What the Calm Doesn’t Tell You

Private credit and crypto are two of the most disliked asset classes in the market right now. That reputation alone is exactly why some investors assume opportunity is hiding there. […]

August 25, 2026

Is Chasing IPO Allocations Actually Worth It?

A listener wrote in with a great question. He’s a tech executive, mid-forties, around $18 million invested, and he’d just been through the SpaceX IPO. He put in a $50,000 […]

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 […]

August 19, 2026

Three Ways to Buy a $2.8 Million Second Home, and How to Choose Between Them

A couple has found a place in Boulder at $2.8 million. They can write a check for the whole thing, put 25% down and finance the rest, or borrow against […]

August 18, 2026

What Advisors Actually Mean by “Complex”

If you held $28 million in a single stock and every advisor you met opened by telling you how complicated your situation is, what would you conclude? Probably what this […]

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