The Grant Williams Podcast Ep. 132 - Jared Dillian
The Grant Williams Podcast
September 5, 2026
In this episode of The Grant Williams Podcast, I welcome back Jared Dillian for a fascinating conversation about his terrific new book, The Awesome Portfolio, and a deceptively simple question: what should an investment portfolio actually be designed to achieve?
Speakers Grant Williams, Jared Dillian
Grant Williams (0:10)
Before we get going, here's the bit where I remind you that nothing we discussed should be considered as investment advice. This conversation is for informational and hopefully entertainment purposes only. So, while we hope you find it both informative and entertaining, please do your own research or speak to a financial advisor before putting a dime of your money into these crazy markets.
You're about to listen to a special preview edition of The Grant Williams Podcast, featuring my friend, author and investor, Jared Dillian of The Daily Dirtnup and the just about to be published book, The Awesome Portfolio, which is what we're going to discuss today. The book is a tremendous effort on Jared's part to help people understand some of their vagaries of investing and he explains why he's in the happy business, not in the money business. I think many of you who read this book will find it incredibly thought provoking and it will help you manage what can be a very tricky process by giving you a much simplified way of doing it. Every episode of The Grant Williams Podcast, including The End Game, The Super Terrific Happy Hour, The Narrative Game, This Week In Doom, Shifts Happen, Kaos Theory and The Hundred Year Pivot, is available to Copper and Silver tier subscribers at my website, grantwilliams.com. Copper tier subscribers get access to all those podcasts, while members of the Silver Tier get both the podcasts and my monthly newsletter, Things That Make You Go Hmmm. So, if you enjoy what you hear on the show, if you'd like more high quality content like it, then please make your way over to grantwilliams.com and join our exciting community today. And now, on with the show.
Jared, my friend, great to see you. Welcome back to the podcast with another book that we can talk about. This is unbelievable.
Jared Dillian (2:02)
Yes, actually, I have another one next year. So, we'll be talking again next year.
Of course you do. It's another year.
Grant Williams (2:09)
Why wouldn't there be another book? You're like the Jeffrey Archer of finance books. It's unreal.
It's absolutely unreal. Well, listen, this one, I've loved all your books. And the thing that always amazes me is how different they are. The different styles of writing you do. But I have to say this one, I say congratulations. The Awesome Portfolio is absolutely terrific. And I think it's going to help a lot of people because it gives some really smart advice. It simplifies a lot of things. And for me, it rang so true to me because it's very much the way I think about things. I try to do exactly what you've tried to get people to do in my own life and it's worked really well to me. So whenever I read stuff, if I'm reading it physically, I have a highlighter pen. If I'm reading it on my iPad, I highlight stuff. And there's an awful lot of yellow highlights in this book on my iPad. And they're all basically me going, yes, remember that. That's right, but just remember it. So congratulations. But let's start talking about what it was that made you write this book. Because it's different to some of your recent books. What was it that made you think, you know what? There's a book in that.
Jared Dillian (3:12)
I've been thinking about this for the last 10 years. I've always had an aversion to the index fund promoters, right? And we know who we're talking about, the people who say you should call your money in the S&P 500 and dollar cost average it. And back in like 2015, 2016, I thought that was stupid, but I couldn't really articulate why.
And then I want to say 2018 or 19, I had this subscriber who's a financial advisor in Idaho. And I don't know what he's doing in Idaho because he's one of the smartest people I've ever met. But he and I were basically running some back tests on different portfolios. So he's like, well, this is what the 60-40 looks like, and this is what it looks like if you add gold, and this is what it looks like if you add real estate. We were getting in this email conversation, and finally we got to this combination. We got to The Awesome Portfolio. I'm like, this is it. The Sharpe ratio is off the charts. The drawdowns are almost non-existent. I'm like, and the returns are incredible. And it is a little bit of a variation on Harry Brown's permanent portfolio, right? But it's better. As I demonstrate in the book, it's better. It's a significant improvement on that. It's got better returns, higher Sharpe, lower drawdowns. The addition of real estate to the portfolio really makes a big difference. So when I found that seven or eight years ago, I knew I had something special. And at the time, I had a radio show. I don't know if you remember this, but I had this small radio show that I was doing. It was nationally syndicated and the radio show eventually failed. But on the radio show, I would talk about this thing called the 2020-2020-2020 portfolio.
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