Transcript: Brian Portnoy – From Complex to Simple · Brian: 2:27 My start in the business is odd. I had a career, of sorts, in academia. I did a doctorate in political science,

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Transcript: Brian Portnoy – From Complex to Simple Published Date: June 18, 2018 Length: 1 hr, 1 min Web page: capitalallocatorspodcast.com/portnoy Brian Portnoy is the Director of Investment Education at $100 billion investment solutions provider Virtus Investment Partners, where he strives to simplify the complex world of money in an effort to help investors make better decisions and lead a joyful life. Brian is the author of The Investor’s Paradox, a book about manager selection rooted in choice theory. His second book, The Geometry of Wealth hits electronic and physical bookstores this week. Our conversation covers Brian’s experience in manager research and lessons learned, choice theory and managing expectations, differences between institutional investment and private wealth management, distinction between seeking wealth and trying to get rich, his terrific new book, and why volatility is risk. Brian’s insightful take on investing and his journey from the complex to the simple is full of investment nuggets of gold. Topics: The purpose of money, wealthy vs. rich, institutional vs. private wealth, volatility

and risk Edited by: Michael Nave

mailto:[email protected]

http://capitalallocatorspodcast.com/2018/06/17/portnoy/

Capital Allocators Podcast EP.57 Brian Portnoy

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Show Notes

2:24 – Brian’s start in the business 5:18 – The useful skills he developed during his tenure at Morningstar 6:37 – The hard questions he would ask 7:15 – Why he left Morningstar 8:53 – What he learned at Mesirow that made him so detail oriented 10:57 – Leaving Mesirow 12:08 – What led Brian to writing The Investor’s Paradox: The Power of Simplicity in a World of

Overwhelming Choice 14:51 – The Art of Choosing 16:58 – What is the investors paradox 17:04 – The Paradox of Choice: Why More Is Less 19:29 – Reaction to the book 24:10 – Difference between his views on the asset management side vs the wealth management side 27:11 – The concept behind The Geometry of Wealth: How To Shape A Life Of Money And Meaning 30:58 – The shapes used to take people from confusion to comfort with money and investments,

starting with the circle 36:00 – Moving on to the triangle in this formula 41:03 – The second triangle, focused on behavior 43:36 – The big blue square 49:29 – Hopes for the book 52:46 – Closing questions


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Ted Seides: 0:05 Hello, I'm Ted Seides and this is Capital Allocators. This show is an open exploration of the people and process behind capital allocation. Through conversations with leaders in the money game, we learn how these holders of the keys to the kingdom allocate their time and their capital. You can keep up to date by visiting www.capitalallocatorspodcast.com.

My guest on today's show is Brian Portnoy, the Director of Investment Education at $100 billion-dollar investment solutions provider Virtus Investment Partners, where Brian strives to simplify the complex world of money in an effort to help investors make better decisions and lead a joyful life. For the past two decades, he has held senior investment research and strategy roles in the hedge fund and mutual fund industries. At Chicago Equity Partners, Mesirow Financial and Morningstar.

Brian is the author of The Investor’s Paradox, a book about manager selection rooted in choice theory. His second book, The Geometry of Wealth, hits electronic and physical bookstores this week.

Our conversation covers Brian's experience in manager research and lessons learned, choice theory and managing expectations, differences between institutional investment and private wealth management, distinction between seeking wealth and trying to get rich, his terrific new book, and why volatility is risk. Brian's insightful take on investing and his journey from the complex to the simple is full of investment nuggets of gold.

Before we get going, I'd like to invite you to join the Capital Allocators Think Tank, a premium content subscription service where you can discuss each episode with me and the guests alongside allocators of sizable pools of capital. You'll also gain access to the library of transcripts of past episodes. Visit www.capitalallocatorspodcast.com, and click the “Premium Content” button to sign up. Thanks for your support.

Please enjoy my conversation with Brian Portnoy.

Ted: 2:20 Brian, it's great to see you.

Brian Portnoy: 2:21 Good to see you, Ted.

Ted: 2:23 Thanks for stopping by. Let's get started with your start in the business.

http://www.capitalallocatorspodcast.com/



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Brian: 2:27 My start in the business is odd. I had a career, of sorts, in academia. I did a doctorate in political science, of all things, at the University of Chicago. And I could summarize that experience by saying that, by 1999, I was both miserable and broke. And I was really thinking to myself, and thinking out loud to my fiancé at the time, like, “what do I really want to do?” And I did have some success on the academic job market, but I simply wasn't happy. So, I just wanted to do something else. As I began to talk to people around Chicago, where we wanted to stay, I met a friend who was at Morningstar, a guy named Josh Charleston, who's still there today, still a good friend. And he said, “you know what? Most of what we do is hire quirky people who are fascinated by the markets, have some writing ability, and we teach them the details that they need to know.” And, so, I went for it.

And it was just an amazing culture, because it is sort of a quasi-academic culture. There are a lot of MAs and PhDs outside of finance. Don Phillips, who really invented the field of manager research – you know, I think he has a Master's Degree in Literature from the University of Texas – but the culture that he built, right next to Joe Mansueto, who remains a mentor to this day, was just summarized what by what was on the door then, as it is now, which is “investors come first.” People are completely overwhelmed by the amount of information that was available to them. And this was… when Joe built this, this was in the early ‘80s when you would go into a library and look at these mutual fund guides. And, so, what he built was an amazing culture that aimed to democratize investing.

And I was just a cub analyst on the desk. A lot of the friends who I made at the time – I mean, everybody sat in a cubicle. Don Phillips was three cubicles away. Joe Mansueto was eight cubicles away. It was a very flat culture. But Christine Benz, and Jeff Petac, and Kunal Kapoor, and Bill Harding, and a lot of folks that are still friends to this day that have gone onto great things, were sitting right next to me. And I fell in love with it. I first got on the phone with a portfolio manager and asked really the only question I asked for about 15 years, which is, “what do you do?”

Ted: 4:47 Good place to start.

Brian: 4:49 Yeah. And just let them of dig their own hole by trying to describe a coherent investment process that produced anything


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of merit. And it was fun. It was a lot of fun. I was there for about four years, and the culture that I was able to observe and be part of, the people I was able to meet, and some of the skills that I was able to develop over that time… it was fantastic. And it made the departure from academia absolutely painless.

Ted: 5:17 What were some of those skills back then?

Brian 5:19 Part of the skill was being able to just get on the phone with somebody you don't know who manages $10 or $15 billion dollars of other peoples’ money and ask tough questions. I had the benefit and the curse of, you know, having survived about a decade of seminars at the University of Chicago where, if you recall the old cartoons where the sheep dog is chasing the fox and they just beat the crap out of each other through the whole cartoon, but at the end the whistle blows, and they sort of walk off into the sunset together… that was the Hyde Park culture, where I had some of the smartest people I've ever met in my life tell me what an idiot I was right before they bought me beers and told me I was doing good work.

So, getting on the phone with a mutual fund manager and asking hard questions about what's their process, what do they own, how do they think about risk, how do they distinguish skill from luck – all of those things that I really didn't fully understand at first and maybe don't fully understand today – I was trained really well. So, you know, just having the confidence to ask hard questions of people who, in most cases, act like they have all of the answers, was something that took a little bit of getting used to. But I have to admit, rankling the occasional hottie PM, uh, was quite fun for me.

Ted: 6:37 You mentioned hard questions a few times. And those, you know, examples of the processes, those seem like the common questions. So, what is a hard question?

Brian: 6:47 Here's a hard question, and I asked it in my very first interview, which is, that, “if you have such a fantastic process, why have you trailed the market over every trailing period for the last 10 years?”

Ted: 6:57 That's a harder question. Different way a phrasing it.

Brian: 7:01 Yeah. I recall that Christine gave – who was my editor at the time, starting in mid-2000 when I joined – she said this was the


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harshest first analysis that anybody had done in the history of Morningstar.

Ted: 7:15 So, why did you decide to leave?

Brian: 7:16 So, I got hired away by a firm called Mesirow, which you know well. Really good Chicago institution. And they had a very quickly growing fund of hedge funds. And, you know, they were just bringing in a large amount of assets in the early 2000s. The big institutional wave into hedge funds began after the 2000 to 2002 drawdown because so many funds – as we've talked about for a long time – were prescient enough or smart enough to be long value and short growth, and they survived ‘99 and they put up absolutely monster numbers. And, so, all of the factors that seem to drive really good performance in absolute return strategies – not just long/short equity, but in convert arb, merger arb, global macro and so forth – it was just a perfect storm, in the good sense.

So, unbeknownst to me, until I got a call out of the blue from a friend of a friend who was running research at Mesirow at the time, Chicago was a global hub for the fund-of-funds industry. You mean, at the time, you had Glenwood, Harris Associates, Grosvenor, Mesirow, and so forth. And it was just really intriguing. It sounded fast-paced. And a part of the story is that after four plus years of interviewing long-only managers at Morningstar, it got a little bit boring, and I wanted to stretch my legs a little bit. And it was sort of like in Willy Wonka when they're in that really tiny room, and then he opens that small door that brings you into this room with the chocolate river in lollipop trees. It was like, “holy moly, this is… this is much bigger and more colorful.”

Ted: 8:53 Mesirow, in the industry, had a reputation for being, sort of, due diligence proctologists. Very deep dive.

Brian: 9:02 Nice to meet you.

Ted: 9:03 Very detailed research. Now, what was it about either what you learned at Morningstar, or Mesirow, or both, that translated to this very deep dive to cover all your t's and dot all your i's?

Brian: 9:19 I can speak, sort of, a personal level and at an institutional level. At a personal level, and something I've thought about as I've


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tried to grow over the years, is that I am naturally curious about a lot of things. And when I want to know something I really want to know. And, so, I was able to express that in one way, you know, doing a doctorate at the University of Chicago, a different way at Morningstar, and then a different way again at Mesirow. But the underlying passion for asking questions and trying to come up with good answers, it drove me then and it absolutely drives me now.

From an institutional point of view, I guess, I could say that at both of those firms there was an institutional integrity that was unflappable. Different organizations – and I've already spoken about Morningstar – Mesirow had a same, a similar attitude. A vast majority of the assets were pension, endowment, foundation. And I think a lot of people, especially during the heady days… I mean, in ’03, ’04, ’05, ’06, ’07, I think we were bringing in somewhere between $1 and $250 million dollars a month that we needed to allocate. So, it was fast and furious. And I think there was an appreciation that, at that pace of growth, if you're not dotting your i's and crossing your t's, you can get into a lot of harm.

It ends up that we, you know, lost some money in 2008, but not nearly as much as some of our bigger competitors. And I think some of that diligence that was in the culture at the time had something to do with that. Because institutionalizing skepticism is something, I think, is very valuable but not easy to do.

Ted: 10:58 And what year did you end up leaving Mesirow?

Brian: 11:00 I left Mesirow in 2010. We had lived in London for a while because I ran Global Research from there. And I'll say… I'll make a very long story short by saying that 2008 changed the business. The hedge fund industry changed, the fund-of-funds industry changed, my role in London and then back in Chicago changed, and it just didn't work out. I mean, I'd been doing it for a long time, and it just felt like it was time to do something else. That's about the time that, call it, sort of a low-key midlife crisis – wasn't anything dramatic – but I really began to think, “okay, what in the hell am I doing with my life?”

I vividly remember I was sitting somewhere… It might've been right down the street here in New York, where I was having a drink before meeting somebody, and I wrote on a cocktail


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napkin “who grows up wanting to do manager research.” So, you know, I left academia with all this vim and vigor and had a great run, but I really began to question what I was doing. And that's when the writing bug bit me really hard. Because it was an opportunity professionally to express myself, and, personally sort of just take stock of where I was on my journey.

Ted: 12:08 And, so, you take this experience where you're deeply ensconced in active management, doing manager research, long-only and then hedge funds, and you write your first book, The Investor’s Paradox. Why don't you paraphrase what that book was about?

Brian 12:24 The argument of The Investor’s Paradox is that expectations matter. I went on to a couple other gigs after Mesirow, and so, all in, over the course of 14 years, I did something north of 4,000 manager interviews. And I don't think there's a strategy on the planet that I didn't do some form of due diligence on. So, I was really blessed to be able to see the entire landscape of really smart, often very well compensated people making just a wide massive variety of decisions about how to best navigate a global capital markets. In my own exploration of, “what I really want to do now, what do I want to do next? Where am I going to find my flow?”, the introspection that I put into, sort of, what I was doing led me to think about, “okay, well what's really driving success?”

To your earlier question and, sort of, implicit notion that I'm a little bit anal and a little bit aggressive at times, I actually kept a spreadsheet of sorts over those 14 years of almost every interview that I did. And I tried to keep track of type 1 and type 2 errors. It was another disaster. I mean, you read Mauboussin, and you read Annie Duke, and you read Kahneman, and you read everybody on decision-making. And, you know, I actually tried at the time to think about, “okay, am I making good decisions? Am I making good non-decisions?” It's impossible to say, because you pass on 99 funds for every 1 that you really dive into. Well, you can't really say whether you're skilled or not if, unless you think about the 99 that you passed on and whether they worked out on an absolute basis and relative to the one decision that you did make. What I concluded after putting a lot of thought and time into it over a couple of years was that true success in investing, broadly defined, is when expectations map up with outcomes. And I began to realize –


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not in its fullest fruition. In the second book, I explored this, I think, a fair bit more deeply – but I began to grapple with the fact that success really wasn't so much quantitatively and precisely about your ability to beat benchmarks, or to achieve a ranking in a certain peer group. It's whether you had met client expectations.

When I dove into that world of expectations formation, I was immediately introduced to the world of behavioral finance. How choices are made, not only Kahneman, but heavily influenced by a book by Sheena Iyengar called The Art of Choosing. It's probably the book that's changed my life professionally and personally more than any other because she writes about choice, not just in a sterile sense, but she writes about choice and expectations formation as being kind of definitive or even constitutive of the human spirit. So, you just don't enjoy the steak dinner. You just don't enjoy the nice vacation. You also, in some cases, more so enjoy the ability to choose the good dinner or the good vacation. Choice is actually a proxy for control from an evolutionary sense. And when we lack control, we are scared. And when we have control, we feel pretty good.

What I realized after 4,000 interviews and 14 years of stumbling around and recognizing that I had made so many awful decisions – and a handful of good ones – is that the conversation between buyers and sellers of complex investment products often lack the ability, the vocabulary, the skill set to structure a conversation so that both people get what they want from that.

So… it's funny. You reinterpret what you've written, you know, looking back, and so, you know, maybe at the time the book was, sort of, “okay, how do you pick a good mutual fund or hedge fund?” And now I realize… I think the better version of what the first book, The Investor’s Paradox, is all about is how do you structure a conversation between buyers and sellers of anything that's complicated so that you can have a win-win scenario. And what I kind of do is set out a set of parameters, almost a script, that could be the framework for what that conversation should go by. So, I concluded that the whole conversation in a fund, a researcher and a due diligence context, is that, you know, you're talking about trust, talking about skill, you're talking about risk, and you're talking about fit. Those are four pretty distinct areas where you really want to


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understand, as either a buyer or seller, what you're getting yourself into.

Ted: 16:57 What is the investor’s paradox?

Brian: 16:59 Yeah. So, the investor’s paradox operates on a couple levels. The first is, there's a book called The Paradox of Choice by Barry Schwartz, who's a psychologist at Swarthmore. I actually sent him a note as I came up with a title. I think the original title of the book was something like Picking Winners, and my agent said, “that's just awful.” I'm like, “yeah, I know. I know.” So, I read Barry Schwartz's book and at some point I emailed him to say, “hey, I think I'm going to use the spirit of your book as the title of my book.” And, by virtue of him not writing back, I took it as negative consent that he was okay with that. But The Paradox of Choice profoundly states that humans are wired to want more choice and more opportunity, but the more choice they get, the more miserable they become. And this is very endemic to Western societies – wealthier societies – where we have more of everything, whether it be in investments, or in commerce, or in education, or in leisure, or in technology, and across every single domain.

And, so, we have something in life called “choice overload,” or “decision fatigue,” where you have 24,000 share classes on Morningstar.com. You tell me how many hedge funds there are these days. 11, 12 thousand? I don't know. There's now 4 or 5 thousand ETFs. There were only 50 in 1999. And, so, we want more and more choice, and we want more and more complicated choices in order to solve what appear to be complex problems. But the more we get, the more overwhelmed we become, and the more difficult it is.

The second level of the investors paradox is that… the idea is, well, when expectations are met, we're in a pretty good place. And when expectations are not met, were pretty upset. This is where I got into hedge fund due diligence and alternative investing generally in the book, was that, because we feel that complex problems of figuring out the global bond market, or where equities are going to go, or anything else like that, you want complex strategies. And we saw – both of us, in our professional lives, you know, last decade – literally more than a trillion dollars flow into these complex strategies. We engage in complex strategies to meet complex problems, but the more


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complex a strategy, the more moving pieces it has, the harder it is to set expectations. So, precisely the funds that we think are positioned to do the best for us during complex times are probably the ones best-positioned to disappoint us.

Ted: 19:23 Yeah. Oh, we've seen that over the last couple of years for sure. So, you go through the process of writing a book, you write the book, you publish it. What happens?

Brian: 19:33 Crickets. Uh, no. Number one, the first thing that happens is that I had a, sort of, an unmitigated sense of joy. I was actually quite proud of myself. I wrote the book that I wanted to write. The first thing I was able to do – not only with myself, but with my wife, and my kids, and close friends, and community – was take stock of, “hey, this is a pretty cool accomplishment.” Like, I did it. So, there was that part of it.

It did go out into the world, and people read it. It sold pretty well. I got a lot of great feedback. I made some new friends along the way. And probably the most relevant or interesting stop or moment along this journey is that there's a guy, at the time, who I didn't know. A guy named Barry Mandinach, who lives here in New York, and he's a veteran of the investment business. He's been in the business for decades now. He picked up the book at the Barnes & Noble in Midtown. I don't even know if it's still there. So few bookstores left. And the title sort of intrigued him – the subtitle, The Power of Simplicity in a World of Overwhelming Choice – and he liked it so much that he cold-called me. You know, he said, “you know, we have some in common, and reference them. And, man, not only do I love the way you write, but it really seems like we think about solving big important problems in the same way. I'd love to just have coffee with you at some point.”

A couple months later I was in New York, and he and I sat down for a 30-minute coffee. And, after four hours, he asked me to quit my job at the time. I was working for a relatively small asset manager in Chicago at the time helping them build out a hedge fund platform. And, you know, that was having mixed success. It was kind of fun, but it wasn't great. And Barry said, “this is what I'm trying to build at Virtus Investment Partners, who I work with now. It's a $100 billion investment solutions platform, and we work with advisors and institutions across a pretty wide array of investment strategies.” He had just gotten there at the


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time in 2014 and he said, “hey, maybe come aboard and help me figure this out. I think there's really an opportunity to do right for a lot of people.” And Barry's mantra has been and continues to be. “how can I help you?” versus “what can I sell you?” And I've learned a lot from him. He's a ment – generally – he's a mentor. At the end of the four hours, I said, “what's the job?” He's like, “I don't know.” And if we somehow got Barry on the line right now and we asked him “what's my job description?” He would probably say, “I don't know.”

But the real blessing is that the firm has really embraced that “how can I help you?” message, and given me a blank piece of paper to write, blog, podcast, tweet, speak on really any topic that we think is going to be helpful. Number one, for the end client, the mom and pop client of Merrill, or Ameriprise, or UBS, or Raymond James, and so forth, for them to really achieve their financial objectives. And secondly, to help our immediate clients, primarily financial advisors, grow and sustain a great practice.

The wealth management industry is going through a ton of really interesting changes now, and, so, you know, nearly 4 years in the not-surprising part of the role is that I'm writing a lot, and I'm creating a ton of content internally at Virtus, which is being shared with thousands of our clients and that's quite rewarding. The unexpected part of it is that, as the wealth management business has increasingly embraced content and, honestly, as so much product has become commoditized and it's less of an edge, the ability to bundle content with very compelling product is sort of the recipe. And, so, we think about “how do you generate mindshare before generating market share?” And, so, now I'm on the road most weeks speaking to a variety of different groups. Sometimes advisors, sometimes end clients. Last year in 2017, for example, I think I did 90 client presentations of one kind or another, and I met about 6,000 people.

And it's great. You get immediate feedback, and you listen. You try to listen. Even though I'm the speaker, I'm trying to read body language, listen to comments and questions. And a lot of the new book is sort of a reflection on me just listening to what people are truly worried about. If the first book was based on thousands of conversations with portfolio managers and trying to assess what they're really doing, this is a book based on


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thousands of conversations with wealth advisors and their clients – just regular folks like you and me, or our parents, or our friends – and trying to write something meaningful for them.

Ted: 24:10 So, before we dive into The Geometry of Wealth, which we will do momentarily, you started your career really, kind of, called on the institutional asset management side, the institutional allocator, looking at funds and a certain vigorous way. And then the last chunk of time at Virtus, you spent more around wealth advisors. Different types of constituent, different types of investment approach. What did you find different in those two ways of thinking about the world?

Brian: 24:40 It's a really good question. You have different problems to solve. I would say on the institutional side, allocators are very good at creating confusion and problems that don't exist.

Ted: 24:53 Such as?

Brian: 24:54 Well, the need to do analysis out to the fourth decimal place to what's the Sortino ratio here, or the Sharpe ratio there, or when this guy says he's got a multi-strat arb fund, you know, how much it's going to be allocated to convert arb, versus merger arb, versus event driven trades? Or whatever. And that conversation that I tried to speak to in The Investor’s Paradox, it can get out of control. Not just because the PM and the sales people are trying to sell something. It's also because complexity is a good thing for people's careers in our industry. I would argue that there's not a complexity premium for investors, so generally, the simpler the better.

How to get from complex to simple, kind of, I've realized in retrospect, is sort of, maybe, the driving theme of the last 20 years of my career. But trying to figure out what an institutional investor wants, in terms of the wide array of due diligence documents that they want, is a very different process. I actually find the wealth management side of the business, which… it's funny. Like, of course I thought I knew who Merrill Lynch or Raymond James was, but I had no idea. My first day on the job I said to Barry, “what's a wholesaler?” I didn't know the process. But now I've been into, you know, hundreds of branch offices and conferences and stuff like that. The questions that get asked are not as deep. You know, you could say from one


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perspective they're not as rigorous. They're probably wider and not as deep, but they're really quite practically oriented.

Basically, I think there's maybe a little bit more of a BS meter on the wealth management side, where someone is really busy building a portfolio and managing the portfolio, but also spending a ton of time managing clients and their emotions and their expectations. And if you can't really explain what you're doing in quick, simple terms, then you've got a problem on your hands. So – I don't even know if I should say this – but, you know, my unofficial job description is that I write for people who don't read. So, I've tried to figure out lots of ways through the way I write, through the pictures that we draw, through some other measures, to try to communicate to people who are justifiably busy and impatient with needless complexity.

Ted: 27:11 So, let's talk about The Geometry of Wealth, your new book hitting the bookshelves momentarily, if not already out. What's the concept?

Brian: 27:19 The concept is that there's a difference between being wealthy and being rich. I'll say, by way of context, that this book is a prequel. Not only because I'm a total Star Wars nerd. Meaning that I got to the end of The Investor’s Paradox and I was, I know at the time and certainly in retrospect, kind of struggling with “what does this all really add up to?” I remember vividly reading some of Herbert Simon's work from decades ago, and this concept of “satisficing,” which is, kind of, a really awkward word for “don't let the perfect be the enemy of the good.” And I think that's just a powerful insight.

And, so, number one, from a personal point of view, as my kids are growing older and I wonder about the decisions they’re going to make, and the situation, and career, and lives that they are going to lead, that that weighs on my mind as they grow older. And, at the same time, as I'm now in more of a wealth management context than a “in the weeds to the fourth decimal place institutional asset management” context, financial advisors and their clients – and their clients could have $50 thousand or $50 million dollars – they're all sort of asking the question, “am I going to be okay? Is this going to work out for me?” And yes, it matters which investments you choose, but that's actually the end of the story, not the beginning.


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And, so, my thought was I actually wrote the wrong book first. So, The Geometry of Wealth ends where The Investor’s Paradox begins. The Investor’s Paradox is about investment decision making. The Geometry of Wealth, you know… to this distinction between rich versus wealthy, I've come to believe that being truly wealthy is the ability to underwrite a meaningful life.

Ted: 29:01 Yeah. You described it in the book as “funded contentment.”

Brian: 29:04 Funded contentment. Yeah. That popped into my mind one day. The thing about money is that you can't escape it. It's a really kind of bizarre topic. Not the practice, but the psychology of money. It infuses almost everything we do, the relationships that we have. And, so, coming to terms with what the psychology of money is really… it was more difficult than I thought it was going to be, because the more I dug, the more I realized that there was a lot going on there.

So, I had focused most of my career on investing, but I talk in the book a lot about what I call “money life.” And by money life I mean not just investing, but earning, saving, spending, and then investing. And the four of those together encompass a lot of different activities, a lot of different decisions, and certainly a ton of different emotions. So, how can I write something that can help people to lead to a good answer to the question, “am I going to be okay?”

Wealthy is funded contentment, rich is the quest for more. And I could cite you 1,001 articles from social psychology and other disciplines that show that the quest for more is nothing better than a treadmill. And no matter how fast you run, you really don't get much further. And we sort of know that to be true. Nonetheless, in wealthy societies and American society in particular, which is relatively materialistic, we are all chasing that. We're chasing more money. And, so, I wanted to really articulate a fork in the road that you can choose to be wealthy and it takes some work, and I set out the path to get there. Or, you can sprint on this treadmill and just be exhausted and not particularly satisfied.

Ted: 30:46 You don't lay it out like it's a difficult choice. So…

Brian: 30:51 Yeah, if you choose one of those, I'm not going to be of much use to you.


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Ted: 30:56 And then you take this path of using shapes: circles, triangles, squares, to walk someone through how you get from, let's call it confusion about money to some clarity and, potentially, funded contentment, including investment decisions. So why don't we start with the circle, and we'll go from there. It's the left most shaped in the book. It's also red – I don't know if that matters or not. But why don't you go ahead and talk about the circle.

Brian: 31:26 Well, you know, I made the comment earlier that I write for people who don't read, or at least don't read much. So, I think it's really important that, on a serious note, to be respectful of your audience is to take them as they are, not as you want them to be. And, so, this was much more clear in the wealth management industry than it was in institutional asset management, where everyone's with their CFA and their puffed chest and their calculator trying to figure out a lot of complex things.

Number one, simple is better than complex. Less is better than more. And, at a slightly different level, pictures are better than words. So, I mentioned I do a ton of presentations all over the country. My PowerPoints have almost no words in them. Every page is a picture, or a cartoon, or a photograph that makes reference to a study. And the feedback is pretty positive because, if I go back a couple decades to my academic days, I thought that being right was the game, and in a very precise way. But now I realize it's something slightly different, which is that you want to engage and empower people as best that you can.

So, you know, I began to think about shapes and the contour and the direction of a path toward contented and fulfilled life. The path that I draw goes from defining your purpose, to setting your priorities, to making specific decisions. So, what I did with The Investor’s Paradox is that I started way at the wrong end. And, actually, The Investor’s Paradox is a book about getting rich. I think it's a subtle book, I think there's some interesting points in it, but it's “let's make great decisions to make more.” This book is not that.

And the circle represents that were going around and around. We set goals, they sound sort of linear, you know, “I want to save for my kid's college, I want to retire at a certain period of


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time.” But what's actually happening in our minds is that we're adapting through a process of choice and circumstance. New things are happening, a lot of things out of our control, and we want to take stock as best as possible as to what really matters to us. And, so, I have a chapter in the book called What Matters, and I walked through, sort of, 2,000 years of the history of the concept of happiness, starting with Aristotle and ending with Marty Seligman and positive psychology, and focusing on things that really drive a more meaningful life. I make a big distinction between, sort of, pleasure and contentment. Aristotle made original distinctions with this and they're still very relevant today. Our day to day life has just wrapped up with mood and pleasure versus pain. And we're just wired that way. It's not a good or a bad thing, it's just who we are.

But in that step back, like, “hey, is this the life that I want to lead? Am I leading a good life?” You know, I think there's sort of four things that, that I sort of talk about that are dealer's choice. Like, okay, I set it out, and on your own, Ted, or anybody else, like, here's an opportunity for you to think about what really matters to you. And it's not going to be the same recipe as mine. But I think these are the main ingredients. And those ingredients are what I call the “Four Cs” – Connection, Control, Competence, and Context. So, we're social animals, so we want to be connected to others, and that's a deep, deep source of meaning. We want control over our lives. We want a sense of autonomy, not just in the cartoonish Ayn Rand-ian sense that you can do whatever the hell you want to others, but in a more subtle sense that you want to be able to write your own story in the way that you want. And, so, when you read people like Solzhenitsyn and Viktor Frankl, you get this inspired sense of even under duress, you can tell your own story.

The Third C is “Competence,” the idea that you're really good at something that's meaningful to you. Whatever that is, your job, your vocation, your hobby, your passion. And then “Context,” which is just that sense of connection to something outside yourself. Traditionally, over thousands of years, that was religion or spirituality. That's still obviously very, very important. But there's your nation, your tribe, your cause, or whatever. And, so, I wanted people in the context of this adaptive circle to say, “okay, these are the things that sort of matter to me, and they're probably going to.” Different things will matter over time, and part what we'll want to do – and, to me, it's fun. I


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think for some people it's stressful – is think about, “okay, here's who I am now. Who do I want to be in the future?” And the path from here to there isn't a straight line. I think it's more of like a spiral, where you kind of… you know, we all deal with a lot of noise and a lot of stress and pain, and navigating that is not only important, it can be super empowering.

Ted: 36:00 So, we figure out how we define that mission or purpose in the circle, and we move on to the triangle. You can tell I'm loving this [laughter].

Brian: 36:10 Well, I like the fact that you're adding, like, this dramatic… I don't know if you, like, bring sound effects in post-production.

Ted: 36:17 Dun-dun-dun… the triangle.

Brian: 36:20 The triangle. I mean, it has a certain Sesame Street quality to it. Old school hip-hop. De La Soul, you know? Three's the magic number.

And the big turn in the book is… okay. It's one thing to think big picture by yourself, or with your partner, or friends walking through the woods. “Hey, what the hell am I doing with my life?” I think where – and I hope the book can fill this gap a little bit – well, how do you then actually connect that to navigating money life? Earning, saving, spending, investing. That's what I'm really trying to accomplish here. And the triangle, as a step, indicates that there's, sort of, three priorities. So, we go from setting purpose, defining purpose, to setting main priorities in our lives.

I'm trying to keep the entire narrative at a simple level. You know, Einstein said, “as simple as possible, but no simpler.” I don't get into the weeds on a lot of things because I've learned, especially from my hedge fund days, the deeper you go into those weeds, the more you're lost and the less likely it is you're going to find some treasure that you think is buried down there. And, so, I refer to the three priorities as Protect, Match, and Reach.

Ted: 37:29 In that order?

Brian: 37:30 In that order. So, the first thing we want to do is develop a mindset and put things in place that protect us from catastrophe. The obvious example is insurance. Now the book


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isn't in any way about whole life versus whatever. I don't… my wife handles that part of our family enterprise. I don't know anything about insurance. But the general attitude that managing risk is in many ways more important than trying to achieve more and more – a higher rate of return. And, so, Howard Marks has been incredibly influential in the way that I think about this, that relationship between risk and return. Putting risk first. But Seth Klarman and many of the great investors you and I have met over time, they engage in something that I've now labeled… They want to be “less wrong.” I think as ambitious people, we want to be more right. We want to be faster, smarter, better, et cetera. That's great. But in the money life that we're trying to manage well, you can easily get over your skis if you tried to be more right. To be less wrong means to think about, “okay, into the future, where might this get off the track?” And I'm not just talking about your portfolio and choosing one fund versus another. I'm talking about lifestyle decisions in terms of what you save, what you spend, decision to have kids, the decision on where you want to live, the vocation that you want to employ. I think a little bit of thinking about risk and what's the potential range of outcomes here, can go a really, really long way to putting people in a good spot. I read the line the other day that the best way to manage risk is just not to be there. So, I think that's really important.

Once you, kind of, have that “less wrong” or that “Protect” mindset, I think you can then get into the day to day of financial planning. I call it “Match.” We know from the institutional side of the money management business, there's something called asset liability matching, but it basically means, you know, mapping up what you're spending and what you're saving, and how is that going to go over time. I think a little bit of thinking from a budgetary perspective can go a long way.

And then, finally, is “Reach,” meaning that we're always going to be ambitious. We always want to aspire. But if you put some good thought and planning into protecting yourself from unwanted outcomes, to really thinking about matching what you own versus what you owe, you sort of won the money game at that point and you can really reach for more. And I don't mean just going and buying a fancy car. I mean you could be more charitable. You can help out your family, you can help the community. You can do good things for yourself. You can basically spend more on the Four C's that we talked about.


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So, it's hard to move from big picture thinking about what really motivates us in life into financial planning. But I think it's really important. And the big trend – I should point out – in the wealth management business is this notion of “goals-based wealth management.” It wasn't that long ago that the advice business was really a brokerage business. It was selling stocks and bonds and funds for a nice fee. It's only over the last 5, 10, 15 years that the bulk of the wealth management industry has bought into this idea that people need a financial plan. So, I think some of the things, when I say them out loud, they seem so obvious. But the fact is that so many of the clients of wealth management firms, actually, still don't have financial plans today. Just to have a plan in place, the chance that you're going to have better life outcomes is considerably more than if you don't.

Ted: 41:02 And if you translate that over onto the investment side, you had another framework of a triangle. And it wouldn't be hard to say, “oh, you know, it's about asset allocation, manager selection, security selection, whatever.” But you started the base of the triangle with “Behavior.”

Brian: 41:17 So yeah, I added a second triangle. I personally find it a little bit confusing, but I couldn't get away from it because I am obsessed with behavioral finance. And, so, once we've defined our purpose, once we've set our major priorities, then we have to start making decisions. And what I wanted to do was define folks, based not just on my observations but on a lot of research, as to what really drives great outcomes, great financial outcomes. And the answer is three-fold.

I think, first and foremost, it's behavior. It's the decisions we make. It's the most emotionally fraught element of the process because we have to look in the mirror and say, “Geez, you know what? I've been hardwired to make some pretty bad decisions and I need to think through what I'm doing.” That's why I think, generally, people who work with financial advisors tend to have much better outcomes. Not because the advisor is a market guru, but because the advisor can be a coach. Somebody on the outside saying, “hey, you know what? Let's keep you from being the worst version of yourself at the worst possible time.” That's incredibly valuable and it's not something that advisors are even to this day are very good at articulating to their clients. And it's something that I do on the road a lot, where I coach advisors on


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that element of behavioral coaching. And, so, behavior, to me, is the main driver. And then within that you can begin to get into the weeds. You know, there's classic studies that you know – and I bet a lot of the listeners know – that show that asset allocation is a much bigger driver of financial outcomes, investment outcomes.

Then security selection. I find the argument both theoretically compelling and empirically convincing. One thing many clients, including advisors, don't realize is that we're making this game much harder than it needs to be. So, if you appreciate behavior and then you set up a diversified portfolio across major asset classes, you're probably going to be in pretty good shape for a long period of time. The issue is that people start where I started my writing career, which is the wrong place. Which is, “hey, let's pick the good investments.” That does matter. It is important. There are some managers who are highly-skilled and much better than others, and it's worthwhile to track them down, but only within the context of a smart portfolio and the recognition that it's your own behavior and transcending your emotional and cognitive biases that are going to get you to a good spot.

Ted: 43:36 Okay, so now we got a big blue square to talk about.

Brian: 43:39 This, to me, is the least necessary part of the book. I think the book goes from most important / most abstract, to most specific / of least impact. So, if someone wanted to read just the circle? Great. Or the circle and the triangle? Good. I hope they read the whole thing. There's a good reveal at the very end, so they should probably make it through the square part.

In the spirit of trying to move from complex to simple, I wanted to think holistically. I wanted to basically rethink The Investor’s Paradox. I wanted to come up with something that was as simple as it needed to be, but no simpler, that can really give end investors as well as their financial advisors a really comfortable conversation space to talk about how investment decisions are being made. Because I see, on the ground, every week meeting with advisors and clients that so much of the conversation around financial planning actually is a conversation about portfolio and mutual fund selection. And I think I've established that that's backwards. That should be the end of the conversation, not the beginning, let alone the only


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part of the conversation. And one of my favorite lines of all time, which is supposedly attributed to Mark Twain – but I think I've been disabused through Twitter and other places that almost nothing that Mark Twain was supposed to have said, he actually said – but, you know, there's this line out there that “if I had more time, I'd write you a shorter letter.” I really work hard explicitly every day at Virtus and in my writing career to write shorter letters.

And, so, the square I think captures what I think are just the four dimensions of any investment decision. Whether you're buying a mutual fund, or private equity exposure, or some of the complex stuff that you and I diligenced on the hedge fund side back in the day. And I put them, I think, in layman's terms. We want, what I call, Growth, Pain, Flexibility, and Fit. And what I do in the book is walk through how each of those are dimensions that we should think about. What I provide in the book or specific questions a client could ask of an advisor, or an advisor could ask of a fund company, to create a win-win situation. A lot of what I've tried to do over both books is create good conversations with people who maybe haven't thought about it exactly the same way I have, and here's a different set of frameworks or different vocabulary.

So, we want to grow our capital – that’s sort of obvious – but how do you set expectations for that? I present some data that shows that, while you can kind of tell whatever story you want depending on which data and over what timeframe, it's an easy question to ask, “okay, what do stock to do over time?” But coming up with an answer that's both accurate and helpful is really quite difficult. So that's the “Growth” piece.

I talk about “Pain,” which is my word for volatility. So, volatility is some abstract number. I think of volatility in terms of the ability to stay in your seat. The more volatile an investment, the more likely it is you're going to get spooked and bolt.

Okay. So, actually, this will be at the part of the conversation where I say Warren Buffet and Howard Marks have it wrong. Okay? I'm not making a bet though. I’m just gonna state—

Ted: 46:46 Alright, alright, alright. Keep going, keep going.


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Brian: 46:49 I'm just going to state that the smartest of the smart guys say that volatility is not risk. And I strongly, strongly disagree. Because what you're really trying to do is achieve your goals in life, and the more volatile an investment is makes it more likely that you're going to drop that investment probably at the worst possible time. It means you're very unlikely to meet your goals. So, I think volatility is risk in a very profound sense. And it's our ability – you know, back to that point about behavior being the main driver – that thinking about that pain ahead of time is really important.

There's two other dimensions I'll touch on quickly – the other two corners of the square. One is “Fit,” and, you know, which I think walks, which is called correlation. But thinking about that is easier said than done, in no small part because correlations are unstable. So, if you look at sort of the classic dyad between stocks versus bonds, and them being supposedly lowly, or un-, and sometimes negatively correlated assets? Well, the real answer is “it depends.” Okay. Sometimes it's positive, sometimes it's negative, and we need to be prepared for those outcomes. We need to think in probabilistic terms about that.

And then the last piece is a technical issue of liquidity, which is a very, very deep and fascinating and complex topic. I refer to liquidity as “Flexibility,” and I put it in terms of “can you change your mind?” Okay, so we're just regular folks. We can’t obsess about this, we can't work on this 25 hours a day. If I'm going to get involved in a particular structure – whether it be a mutual fund, or a hedge fund, or private equity vehicle, or an MLP, or whatever the case may be – am I going to be able to move on if I want to? And one shouldn't assume that more flexibility is better. In some cases, the ability to buy and sell something on every tick can lead to really bad outcomes. And, so, we need to think about, sort of, the ability to change your mind is a double-edged sword. We know that people who are in target date funds and who are in, sort of, the institutional or defined contribution share classes of big funds, tend to have better behavioral outcomes than those who are in the daily discretionary versions of the exact same funds. And why is that? It's because they can't really change their mind easily. They can change their mind, but put two click boxes and a signature box on a screen and they're probably not going to do it.


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Ted: 49:14 Yeah, I think the institutional parallel to that is private equity, right? There's a lot of benefits to private equity. There's a lot of risks in the asset class, but, at the end of the day, you've taken layers and layers of human emotion out of that potential decision process for a long time.

Brian: 49:27 And it's one of the main advantages of that asset class.

Ted: 49:29 Alright, so the book is about to come out, and what do you hope happens?

Brian: 49:33 I hope it makes a difference in people's lives. I really am privileged to travel the country and meet thousands of investors and, kind of, hear the stories about, you know, what matters to them. And it takes me back to my Morningstar days. It takes me back to that, you know, that sign above the door that Joe put up there: “Investors Come First.”

And I think a lot of people are intimidated by money. It's sort of the starting premise of the book. It's the most emotionally fraught thing. It's a lightning rod for all of the other things in life that drive us a little bit crazy. It can make good situations bad, and make bad situations worse. And, so, I hope people can read this and see, through three basic shapes, that you can actually underwrite contentment. That you can afford a meaningful life with just a little bit of preparation and a little bit of work along the way. I tried pretty hard at various points through a principle that I call “adaptive simplicity” to say, “okay, there might be 15 things to consider here, but I'm not going to talk about 13 of them. We're only going to talk about 2.” And it goes back to that notion of “satisficing.” We're not going to let the perfect be the enemy of the good. So, I hope people can read this, and, number one, say, “geez, I'm not alone. This stuff's hard and it's stressful, and I don't want to talk about it.” No one likes talking about this, and maybe [this] gives them some tools to end up in a better place.

Ted: 50:59 Yeah, it's funny. It's easy to sit back and say, “oh, you know, in the institutional investment world, we know all this stuff.” But, and we've talked about this, the number of professional money managers whose own personal balance sheet is not quite in the shape it should be is kind of astounding, right?

Brian: 51:19 Oh yeah. We know a lot of these guys. It's a dog's bowl.


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Ted: 51:23 Yeah. I mean these are lessons I wish I had as early in my career as I was learning what a hedge fund was. Same as you, like, early on you want to learn the right fundamentals for your own life first.

Brian: 51:34 And we have kids. Very similar ages. Maybe this should have been the first answer. It's certainly something I've thought about for years now, but I worry about them. I mean they're 15, 13, 11, and they’re… my wife and I are super lucky to have them. They're just, they're wonderful and I think they're pretty lucky in the situation that they've been born into. And, you know, sort of, the five of us… we’re up for a good fight. You know, Tracy and I really want them to have happy and meaningful lives. I did write this book in a way where, at various points, each of my three kids will be able to read it and hopefully make sense of whatever it is they're going through.

The book has dozens of Easter eggs in it for various people. I think there's one there for you, Ted. And, so, the book has Easter eggs for my three kids at various points, which they'll find probably in a decade or so. And if we accept that 15 to 20 years ago, Google wasn't a thing and we fold forward 15 to 20 years, and, you know, the conversations you have with certain entrepreneurs… the world is so fascinating, but it's also so unpredictable. I think I tried to create a little bit of a timeless framework for my kids to think about how to afford a meaningful life, long after Tracy and I are gone.

Ted: 52:45 Fantastic. Alright Brian, you know it's coming now, so we're going to turn to some closing questions. What was your favorite sports moment?

Brian: 52:54 I've been waiting to answer this question for so long because I remember – I've listened to all your podcasts – and the first time you asked it, what popped into my mind was Santonio Holmes on his tip toes with about 30 seconds remaining in Super Bowl 43. I probably re-watched that video and the video of James Harrison returning the interception for 101 yards – I don't know – 10, 12, 15 times a year? It is my happiest sports moment. I grew up in Pittsburgh.

Ted: 53:20 Right so… I was going to say, for people who are not Pittsburgh fans, why don't you go ahead and explain who these guys are?


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Brian: 53:28 Oh, I'm sorry. Geez, I buried the lead. I bleed black and gold. I grew up in Pittsburgh, and anybody who grew up there or as part of Steeler's nation kind of gets it. We've got black and gold Terrible Towels every Sunday. Yeah, I… if you want me to, I could revert into my old Pittsburgh accent, but I'm trying to sound more sophisticated [laughter].

Ted: 53:46 What's your biggest investment pet peeve?

Brian: 53:50 You know, I think back to the very first conversation I had at Morningstar. So, I did a thousand and two interviews at Morningstar over four years, and I think to the very first one. And here was a guy who simply could not and would not consider the relationship between skill and luck. Now I wasn't calling the guy an idiot, and he wasn't an idiot. He was a totally capable fund manager. But what I found – and it does drive me nuts, and it drove me more nuts during the hedge fund days – when I was talking to these masters of the universe guys who were just so smart, but then you break down the numbers and you show that there are various forms of skill, and that luck is a big part of it, it drives me crazy that, I would say, a vast majority of money managers I've met over the years – and it's a big number – simply will not accept that luck is part of the equation.

Ted: 54:42 Yeah, I agree with you.

Brian: 54:43 You agree?

Ted: 54:44 Yeah. What information do you read that you get a lot out of that others might not know about?

Brian: 54:49 So, I read a lot of stuff that our friends are familiar with: economic history, behavioral finance, and I'm kind of obsessed with all of that stuff. I read a lot of political history. In Chicago I lead a reading group for a big group of folks, where we just sort of tackle some of the big issues that are alive in society. But I wouldn't say that there's, sort of, some, sort of, micro topic that I've dove into that I have found to be my own little treasure trove.

I will say that something I do a lot of that few people know anything about – or at least that I do – is I play board games. I play a lot of board games. I love board games. And we're not talking Candy Land or even Monopoly. We are in a Golden Age


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of gaming. There's a gaming store in Chicago down the street from me that has hundreds and hundreds of boxes lining the shelves. And whether it be Dominion, Settlers of Catan, Magic the Gathering – which is a huge multi-hundred-million-dollar industry. It’s a game owned by Mattel – Quarto… I mean, we have dozens and dozens of games at home. And my favorite kind, there’s sort of a trend toward so called “cooperative games.” So, we play Monopoly and I'm trying to bankrupt you. A lot of games now are designed where we're all on the same team, but we have different skills, you know? We're sort of like the A-Team… You'd be George Peppard. You'd be the leader.

Ted: 56:23 Yeah, the big cigar hanging out of my mouth. So, are you Mr. T, then?

Brian: 56:27 Yeah. I pity the fool. Right? No.

So, you're on the same team and you find ways, through collaboration, to beat the game. So, there's one, for example, that's called Forbidden Island, and the island that… the playing board disappears. So, it's hexagons that intersect and, on every turn, chunks of the board go away because the island is disappearing into the sea.

Ted: 56:53 Oh, that's so cool.

Brian: 56:54 And, so, I play this with my kids and it's a really cool world. And you think about all the different ways that we can have fun competing against each other or collaborating. I do have a bit of a dream that I'd like to create my own board game one day.

Ted: 57:11 I love it when a plan comes together.

Brian: 57:13 Yeah, oh geez, okay, George.

Ted: 57:15 Last one. What life lesson have you learned that you wish you knew a lot earlier in your life?

Brian: 57:21 I want to flag two, because they're both really important to me. The first is – and I didn't learn either of these until not that long ago – the first one is that we're always selling. Everybody is always selling something. So, you know, I spent many years on the south side of Chicago in the ivory-est of ivory towers arguing about some of the most esoteric and irrelevant things you could imagine. And the name of the game was being right, you know?


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And you dug in and you spent months and months researching just one point so that you can weigh, you know, over somebody who's researching the same thing. That didn't set me up, in multiple ways, to be successful in the business world. I think I had some success for other reasons, but this notion that you want to come up with the right answer, it is one thing. But the bigger picture of, you know, that's not really how people get ahead. What they get ahead with is selling, in the good sense, you know, ideas, or services, or products, or whatever, that are helping others. And, so, the ability to engage, the ability to be kind and care, and to bring people along. I always sort of knew it, but then I looked around at people who weren't salesmen per se, but they were quite successful. And I realized what they were all doing was creating compelling visions that others bought into. I wish someone had told me that.

The second one, quickly, is the principle of optionality, which is something I've thought about a lot in the last few years, and I think about it with my kids a fair bit. The idea that much of success is not about pointing to the fences and hitting that one home run and walking off the field. It's more about having lots and lots of iterations across multiple games in your life where you're trying to source as many cheap options as possible. Life's pretty random and arbitrary things happen for reasons that we can't and won't understand. And, so, I think one of the main ways to be successful is to have relationships, to have skills – and these are all options, in a very generic sense – because you just don't know what's going to connect. And that is not something anyone taught me until, maybe, five or seven years ago. And once a couple of folks, kind of, turned me on to that way of thinking, I've tried to learn more and more about that.

Ted: 59:53 Brian, thanks for coming by. Thanks for sharing your work and everyone go out and buy The Geometry of Wealth.

Brian: 1:00:00 Thank you, my friend.

Ted: 1:00:02 Hey, before you take off, I've started sending out a monthly email that shares a small selection of what caught my eye over the month. I get a lot of emails like this and I'm sure you do too, so I'm only going to send no more than a handful of the very best things that caught my eye. If you'd like to receive that email, hop on my website at www.capitalallocatorspodcast.com and join the mailing list.


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Transcript: Brian Portnoy – From Complex to Simple · Brian: 2:27 My start in the business is odd. I had a career, of sorts, in academia. I did a doctorate in political science,