Jared Dillian on ‘The Awesome Portfolio’

Jared Dillian on ‘The Awesome Portfolio’

Author: Paul Ollinger September 30, 2026 Duration: 45:04

My guest today is Jared Dillian, a former Wall Street trader, DJ, and the best-selling author of Street Freak, No Worries, and his new book, The Awesome Portfolio.

Let me ask you a question: Can you let your investments ride without losing sleep or checking your portfolio every eleven minutes? I have trouble with this. Even though I feel really good about what I own, I still peek at my balances a couple of times a day—just to make sure the world isn’t exploding.

In The Awesome Portfolio, Jared explains why owning one fund with 500 different stocks doesn’t necessarily make you diversified or safe from violent market fluctuations. He argues that a portfolio balanced across five different asset classes—equities, bonds, commodities (like gold), real estate, and cash—will produce very good returns and drastically reduce volatility.

While nothing I say in this discussion should be considered professional financial advice, I think his idea is interesting and worth your consideration. We also talk about trouble in the bond market, political risk, financial advisor incentives, and investor psychology, including how our emotions can wreck even the smartest investment plan.

Please check out my new article in The Hill: Nikole Hannah Jones Just Ran Head-first Into the Great Dumbing Down

To get invites to live streams with great guests like Jared, Dave Barry, and many more, subscribe to my Substack HERE.

Follow Jared HERE and get the book HERE.



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Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 50

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