In conversation with
Callie Cox, Ritholtz Wealth Management

In our series “In Conversation With” we share conversations with industry leaders. Callie Cox is the Chief Market Strategist at Ritholtz Wealth Management and the author of OptimistiCallie, a newsletter with Wall Street quality market and investing insights. She's passionate about teaching everyday investors about the power of investing for their wallets and their lives. We spoke with her about her background, the importance of translating market insights for “the rest of us,” and why now is the time for advisors to embrace their next generation of clients. 

Flourish: Tell us about your background beyond the bio. Where does your love of markets stem from and what led you to the position that you're in now?

Callie Cox: I don’t have a traditional finance background, I really came in through the back door. I went to UNC Chapel Hill for journalism and, when I was in college, I had no idea that bond yields moved in a different direction than prices. I didn't know what a put or call was. I barely knew how the stock market worked. All I knew was that I loved writing, especially about numbers.

I took a business journalism class where we wrote stories about fake moves in the market or fake releases from Apple. We interviewed people in the community about their businesses, but the financial aspect of it. I really liked it and thrived in an area where I could quantify the story.

After I graduated, I was fortunate enough to get an internship at Bloomberg. I like to consider myself one of those rebellious skeptics who came into finance without a finance background, and I was like, "What is everybody doing here? Why are you jamming all these words into a sentence that makes no sense?" Thankfully, there were analysts who recognized that I was a beginner and would explain really complicated topics to me, like, "Callie, the market's like a beach ball right now. Push the beach ball under the water and you can only hold it down there for so long before it pops back up." I was hired out of that program as a reporter and made the rotation around the newsroom. When I got on the stocks desk, my world opened up. I was able to talk with strategists about what markets are doing, where they could go next, and different trends that could affect markets. They would break things down for me, masterfully bringing in storytelling in a way that inspired me.

At that point, I realized that I could do this. I was a reporter writing about numbers and thriving. Then I had a source who took a shot on me and I moved from New York City back to North Carolina to work for TABB Group. The rest is history. I got into research and I never looked back. I really enjoyed writing about markets and was lucky enough to get into equity research. I worked for LPL, I worked for Ally Invest, and now I'm at Ritholtz and absolutely loving what I do. But there's the thread of telling a story about markets and money that has been woven through my whole career.

Flourish: How is your work at Ritholtz supporting advisors and their work with clients?
Callie: Strategists talk publicly about markets, but there's a lot of behind-the-scenes work that goes into what you see on TV. My job at Ritholtz is to be a translator for the different parts of the business. I'm a translator for prospective clients through media when I appear on CNBC to talk about markets, getting our brand and our voice out there. But more importantly, I work with advisors to teach them more about what's going on in markets and how it relates to our portfolios. We're a $5 billion RIA, we manage over 1,000 households, and those clients have questions about the markets that they hear about day in and day out, going up and down. It's their money, and money is highly emotional.

Flourish: Tell us more about your newsletter. Who is the audience and what are you aiming to do with it?
Callie: I write my newsletter OptimistiCallie, which is kind of a summary of what I'm talking about to advisors, dialed down a few tones. I try to come up with an insight and think of ways to express it that help the business and help the advisors be more of the superheroes they already are. I publish the newsletter every Monday about topics in markets and investing that I think the average American would care about. Usually when you read Wall Street research, it is really hard to understand and it's typically about something that means nothing to most of us.

I worked at LPL, Ally, and eToro. Then, when I moved over to Ritholtz, I decided to rip the bandaid off and write without boundaries. I aim to write the way I would talk to a friend during happy hour.

The newsletter is young right now – my first post was at the end of June – but it's really a continuation of what I've written in my past three roles. I want to prove to the rest of the finance industry that this can be done, that there is a value in educating all of us about how markets and money work. Retail investors, the average American investor, has become a bigger and bigger part of financial markets. Of course we should pay attention to them. Of course we should be writing research for all of us. But nobody is really doing it yet.

Flourish: What is the most valuable thing, in your opinion, that clients get from working with an advisor, for those who are maybe skeptical or may not appreciate them?
Callie: I have been in that boat for most of my career. There are good reasons to be skeptical of some advisors. There are still a lot of shops out there that are commission based. There is a lot of product pushing out there.

You have to have a lot of trust with your advisor. After all, they're managing all of your money and giving you recommendations on how to retire, how to buy a beach house, and all the big life events that you inevitably have to tangle with. 

The first thing they ask you is, "Tell me about you. Tell me about your hopes, dreams, goals, your first experiences with money, where you want to go, why you called me up." They really dig in to learn about the client first, and then they start running through a plan. They actually don't get to that financial plan point for a while – and that's on purpose. Our advisors are always very intentional about learning about clients and how they tick.

People might ask why I use an advisor, when I do this for a living. I think that there is real value to having an objective eye on your finances, because money is never objective. You could say that you're going to stick to the spreadsheets as much as you want, but from personal experience, that is really hard to do when you have major decisions on the line. I like having a third voice to help guide me through major life events. 

Flourish: Ritholtz clients hold an average of $142,000 with Flourish Cash^† and have earned more than a combined $1.2 million in interest since Ritholtz started working with Flourish in 2019.^|| What is the role of cash in the financial lives of investors and why does Ritholtz think it's important to include cash in the financial planning process?
Callie: Cash is the first investment that any of us learn about. Our parents ask us to rake the leaves and they'll give us a crisp $5 bill in return. A lot of people, including myself, have had that experience. So, cash is one of the investments that we're all familiar with and it's the one that we lean back on when it feels like things are shaky.

Cash is the most basic form of capital that you can have in your portfolio. It sits there as a place to save up for a short-term purchase. It sits there as an emergency fund in case you lose your job or have an unexpected medical emergency. It also sits there so you can participate in riskier assets when it's a good time to do so, like when the stock market is selling off. You hold cash for comfort and for opportunity. At Ritholtz, we try to focus on both the role that cash can play in your life, but also the amount of risk that you need to take to get to those goals that we're advising you on.

Flourish: You talked about intuition and empathy. How can these traits be beneficial to advisors and within the world of finance and investing?
Callie: The best advisors have an incredible amount of empathy because they are walking with you through some of the most important decisions of your life. I think the industry is just now coming around to the human connection aspect and how important it is. I wasn't working for an RIA in March of 2020, so I can't tell you how advisors react to extreme crises, but it has amazed me how well our advisors have trained their clients to expect these ups and downs in markets.

In August, when we had the yen carry trade implosion and the S&P ended up falling 8%, I was asking the advisors, "What do you need? Let me write everything for you. I want you to be over-prepared, not under-prepared."

But, while many of them said that they got questions, clients weren’t panicking, asking why they were invested in the stock market when the stock market was falling. Instead clients were asking what the yen carry trade was, asking how it affects our firm investment strategy, which, spoiler alert, it didn't. Just asking really smart, logical questions. There was less emotion and more curiosity. I really think that's an attestation of how incredible our advisors are and how well they've been trained to lead clients through volatility that should be expected.

Flourish: What do you think financial advisors should be talking about with their clients now? What's the topic that they should not avoid?
Callie: You probably hear a lot of advisors talk about the younger generation of investors and how it's really hard to connect with them. And yeah, okay, that's true. I’m a millennial and can say that we’re different. Gen Z Americans are even more different. But we’re building our wealth quickly. Millennials are at the point in their lives where they have enough wealth to look for an advisor. This is the industry's time to step up. That time that you've been talking about for so long, it's finally here. You have to embrace it and you have to understand how to appeal to a younger generation who doesn't think about money the same way as their parents did.

For a lot of us, we have some financial wounds from the global financial crisis. Some of us came out of college and weren't able to find a job. Some of us were in high school and had parents who lost jobs. We have a pretty unique experience with money and it's going to cause us to invest differently. It's going to cause us to spend differently. It's going to cause us to make different emotional decisions with our money. And we're going through this in a world that's becoming increasingly unaffordable. There's an opportunity to talk to us, but there are challenges too.

I want to see advisors talk to clients more about their money story and their money experiences, digging to the root of how their clients feel about money. For younger generations, understand how millennials and Gen Zs view money and how that could differ from your classic, middle-aged client. Try to understand us better, try to understand a service model that fits our needs and wants better. Just be prepared for change. I think the industry is a bit of a dinosaur, and one thing that Ritholtz has been really good at is embracing change and how the world is changing. Understand how different generations view money and how they tick. 

This interview has been edited and condensed for clarity. This material is provided for informational purposes only. The views and opinions expressed in this interview are those of the individual being interviewed and do not necessarily reflect the views or opinions of Flourish. The inclusion of any external party in this interview does not constitute an endorsement or recommendation by Flourish. The information provided is not intended as financial, investment, or legal advice and should not be relied upon as such. 

Investing involves the risk of loss. This article is for informational purposes only and should not be regarded as personalized investment advice or relied upon for investment decisions. Callie Cox is an employee of Ritholtz Wealth Management. All opinions expressed by them are solely their own opinion and do not reflect the opinion of Ritholtz Wealth Management. Employees and clients of Ritholtz Wealth Management may maintain assets at Flourish. Ritholtz Wealth Management does not receive compensation from clients for using Flourish.