In conversation with Jill Schlesinger

August 7, 2023

Estimated reading time: 5 minutes


Jill Schlesinger is the host of Jill on Money and an award-winning Business Analyst for CBS News. She takes everything complicated and intimidating about the economy and markets, and breaks it down for the average person. Before that, she ran an RIA for 15 years. She is the author of two books, The Great Money Reset and The Dumb Things Smart People Do with Their Money

Flourish: Would you share your career highlights and what led you to where you are today?
Jill Schlesinger: I zigged and zagged, nothing was planned. For anyone who's over 50, we didn't plan our careers. We just did things, took the next job, and said yes to whatever was offered.  Jill Schlesinger

My father was a trader on the floor of the American Stock Exchange and I was a clerk for my dad and his company over the summers. I went to Brown University and then worked on the floor of the Commodities Exchange after graduation. I had spent my whole life thinking I’d follow in my father's footsteps and, for a few years, I was a trader and made great money. But I realized I didn’t like it.

I ended up finding my way into an RIA in Providence, RI where there were three people. A year later, I bought into the partnership and we grew the RIA into a big regional firm. We were really into being fiduciaries, being certified financial planners, and doing the right thing by our clients.

Through a connection, my business partner and I ended up hosting a call-in radio show where we gave financial advice. This was in the '90s and it was a booming market, so we got business like crazy. Providence is small, so, if you're on the radio, then you're automatically on TV, and then you're writing a column in the paper. We grew the business, then sold it to a roll-up firm in 2005. But I was fried, and a friend introduced me to a producer at Fox News, where I was on the air a lot, which led to other cable opportunities. 

In the beginning of 2008, at the start of the financial crisis, I appeared on CNN. I went on the air and explained to people what was happening in the financial crisis. I think I scared everybody who watched me that day. A CBS News Producer asked, "Can you come on the air and talk to us? Are you exclusive?" I wasn’t exclusive and started appearing on CBS. Early in 2009, CBS approached me to help launch their new financial website CBS MoneyWatch. I signed a contract in April and I have been at CBS News ever since. There have been many iterations, but there was no forethought to that career journey. I just meandered around, seeing what I liked.


Flourish: At Flourish, we work exclusively with independent RIAs. We spend a lot of time trying to get into the minds of RIAs. Could you take us back to when you were on the RIA side and walk us through the experience?
Jill: The best part about being an advisor is that you’re helping people solve their problems. You’re bringing them through the emotional journey of their lives and helping them figure out how to use their money to get where they want to go. If you're good at what you do, your clients call you about everything. You're more of a life coach than a financial advisor. There is something incredibly satisfying about building that relationship and watching clients go through hard times and come out the other side. That's amazing.

The hardest part is that people are crazy, emotional beings. It's exhausting to be the person who has to absorb all of that. You give them advice, and then often there's nothing else you can do. I wasn't very good at letting go when people didn’t follow the advice.

In terms of the day-to-day, when I first got into the business, we were selling commission-based mutual funds because that's how you made a living. Unlike most other people, we were doing real financial planning along with it. The business evolved when we started realizing that we were unique because we were doing the planning, which differentiated us from the commission-based brokers.

We switched to fee-based advising in the late '90s, which was incredibly expensive for us. We had to go out and borrow money to do the conversion because you take a massive upfront hit to your numbers. My business partner and I pledged our homes against it and borrowed the money to make the switch. We put a billboard in the heart of Rhode Island right after the dot-com bust that said, "Is your broker making more than you?" I'd never gotten more responses to any direct messaging.  

Flourish: Tell me about your attempt to introduce a flat fee. 
Jill: We attempted to try a flat fee – not an investment management fee – and we came close to going broke. We were charging a minimum of $5,000 and a maximum of $10,000. If you had a portfolio of a million dollars, a 1% fee is $10,000. If you have a portfolio of $3 million, we said, "You should not pay any more." You know what happened? Anyone who was paying $10,000, $20,000, $30,000 in fees at other places came into our office and said, "If you're only charging $10,000, you must not be worth it.” We almost went broke and had to crawl our way back out of that one.

It was a brilliant idea, but we were early. We did focus groups and had money behind us. We thought we were the most brilliant people in the world, but I think that it was hard because there wasn't enough automation. We got a ton of business from a half a million to $1 million dollar portfolios, but had to hire so many people and were making less per client on each of those people. For a flat fee, they had a certain number of meetings and calls a year, but we could never stick to it because we actually wanted to help people. It was impossible to say, "Oh, I'm sorry, that’s your third call, you're done."

I think that it’s more possible today. There’s the habit of subscription services where people are just used to paying a set amount each month for something. 

Flourish: In your latest book, you say, "Cash is the answer to the great what ifs." Especially in the ‘90s, cash was not usually part of the portfolio. How did you incorporate cash into the financial planning process?
Jill: I made cash part of the portfolio. It was difficult because people didn't consider cash to be an asset class, but I have always thought of it as a buffer. It's opportunity; it's flexibility; it's everything. 


Flourish: We had one RIA say, "We're not in the making money business; we're in the not losing money business.”
Jill: Preservation, yes. I think that advisors are in a lifestyle business. You're in a business where someone says, "Here's the lifestyle I have. Here's what I want my lifestyle to be." Money is just the tool to get you where you want to go. And cash is part of that.

Flourish: Shifting gears, in a recent episode of The Compound and Friends podcast, you talk about coming out to, in your words, 3 million people on CBS News earlier this month. Can you speak to that and the overall role of identity and authenticity in your career?
Jill: I came out in 1992. Providence is tiny – there are a million people in the whole of Rhode Island. Everybody kind of knew that I was gay, but it wasn't something I advertised. Time went by, I came back to New York and got a job at CBS. I'd been out for so long and didn't really know how to be in a closet. I always assumed that people knew.

CBS did an online Pride segment that aired in June based on essays written by three people at the station who are gay or identify as LGBTQ+. It did occur to me that not every one of the three million people who watched knew beforehand that I was gay. It's not like you go on a show and say, "Let's talk about the debt ceiling. Did I tell you about my girlfriend?"

After the segment aired, people that I have known for years would send me emails, like, "I had no idea that you were gay. That was the coolest segment." It was really incredible to be able to participate. 


Flourish: We work with RIAs of different sizes. Our cash product fits a set of clients, but there's something in the RIA mentality where they’re always thinking about their biggest clients. We tell them it's perfect for clients with $1-5 million net worth. And they say, "But I got this guy with $20 million." What is it in the psyche of RIAs that makes them concentrate on the one big client and not think about the other 99 clients? 
Jill: Advisors make the most money on those top 20 clients, and they want to figure out a way to treat them special. But what if they could treat all of their clients like the $20 million client and you make it easy and seamless for both the $5 million client and the $20 million client.

And, by the way, the $5 million client could know the $20 million client. Your best source of business is existing clients. Advisors are a bit enthralled by their big clients. My biggest client was my most humble client. It was a couple who had hit the lottery, and they were unbelievable.

Flourish: Literally won the lottery? 
Jill: Yes, $80 million – $23 million after tax and lump sum payment. It was a teacher and a translator. They were married with five kids. They came in to interview me, filled out the intake form, and we went through everything. At the end, I asked if there was anything else they wanted to tell me? And they said, "Well, we've come into some money." I thought someone died and it would be like $50,000. The husband said, "My wife won the lottery and we have $23 million sitting at Washington Trust in Westerly, Rhode Island." I literally said, "Get out of here. You hit the lottery?"

I asked why they mentioned it at the end of the meeting. And they said, "Well, we just want to see how you treat everybody." I thought that was brilliant. You never know where your $23 million client's coming from. 

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 the Firm. The inclusion of any external party in this interview does not constitute an endorsement or recommendation by the Firm. The information provided is not intended as financial, investment, or legal advice and should not be relied upon as such.


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