Live from the 2026 MoneyShow Las Vegas, we sat down with Oliver Renick (Chicago: Future of Finance) and Cullen Roche (Discipline Funds) to talk about how investing is changing and how your portfolio should change with it.
We cover Cullen’s new book Your Perfect Portfolio, why there’s no single “perfect” strategy, and how to think about diversification in a market full of rotation, volatility, and big valuation gaps between the U.S. and global stocks.
Meanwhile, Oliver breaks down the rise of the “pro-tail” investor, how options and convexity are reshaping portfolio construction, and why AI is changing correlations across stocks, gold, and Bitcoin.
We also get into crypto’s role in portfolios, hedging with options and buffer funds, and why semiconductors may be the real signal to watch in 2026.
If you’re trying to build a smarter, more resilient portfolio for what’s coming next, this episode is for you.
CHAPTERS:
00:00 — Live from MoneyShow Las Vegas & guest introductions
01:00 — Your Perfect Portfolio and modern portfolio strategies
02:10 — The “pro-tail” investor, options, and convexity
03:45 — 2026 market volatility, rotation, and diversification
04:50 — Bitcoin, crypto, and alternative assets in portfolios
05:55 — AI as a productivity shock and changing correlations
08:55 — Hedging risk: geopolitics, tail risk, and buffer funds
11:25 — 2026 outlook: global markets, semiconductors, and expectations
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