Yours in Finance: Frida Leibowitz

The same questions asked of the people shaping the future of banking and fintech.

Welcome to Yours in Finance, where we are tracking how banking is changing. Once again. 

Frida Leibowitz, co-founder and CEO of Debbie Rewards, responds to our questionnaire: "I never regret paying for experiences. Things? Maybe. Experiences? No."

About Frida

Frida Leibowitz is the Co-Founder and CEO of Debbie Rewards, the first rewards program for financial wellness, where users earn points for every dollar they save or put toward paying down debt. Debbie partners with financial institutions across the country to help acquire, retain, and engage younger members.

Before founding Debbie, she spent several years at Marcus by Goldman Sachs and before that at several fintech and healthtech startups. As an immigrant and first-generation college graduate from a single-parent low income home, she is deeply passionate about expanding access to financial security.

Q&A 

The interview is edited for brevity and clarity.

What's difficult about managing money? 

Oh, it’s just so many things. I have to think about what's at the top.

You know, as they say, more money, more problems. I think it’s on both sides. If you have too little. If you have too much. I think it's such a central part of everything you do. But that also means that it can be one of the biggest psychological drains. 

It can take up a lot of brain space and emotional space. I think probably one of the most difficult things is how much space it takes up in people's lives and in every area of life, really. 

If you have too much of it, you worry about what you're going to do with it, how you're going to protect it, how you don't lose it, how you have to think about all those things. And then also, in your relationships, that starts to become a big part of it. Maybe you're less trusting. You have a harder time having money conversations with people. Whereas on the other side of it, on the other extreme of it, if you don't have it, it's the same thing, right? You're always stressed about it. You're thinking about it. You don't have it. And that also causes a lot of changes in relationships with people. Probably somewhere in the middle is the least, but even then, I'm sure it always takes up space in people's minds. 

What do you like about digital banking?

Control, empowerment, ownership. It puts a lot of the power in my hands as opposed to having to rely on someone else. 

What financial habit or behavior are you unwilling to automate? 

I want to say I don't want to automate spending. The truth is I do it all the time. I have so many things that I just pay for. You know what? I'm not willing to automate budgeting. Because I don't like budgeting at all. I don't like to think that way. So, the way I do it is a little bit different. I try to change my mindset about how to spend my money and then do more of like reviews. I don't budget in advance, but I do reviews, and then I think about how I can make small improvements for the better going forward. I think it's about being money conscious, so it's like staying in touch with what's going on. 

I hate having an automated system that's tracking my moves. It feels very restrictive, all of these apps that track how you're spending in every category. And to me, it's more about being just financially conscious and not budgeting actually, and just thinking about how, in general, in everything that you do, you think smartly about money. And also that instead of thinking about how to not spend or not do certain things, you think about how to add money to your savings actively, or pay down specific debt, or when you think about the dos, as opposed to the don'ts. 

Instead of budgeting, I do reflections. I'll go once a quarter, and I'll reflect on what I've done, and I'll look back, and I'll see how I did. With that comes another thing. One of the first steps I took in my financial health journey was to just look at my balances more often. At that point, I was doing it every day. Now, I probably do it once a week. Like, just review all of your balances, and do it regularly. Because it reminds you, what do you have? How much do you owe? You're just aware of it. Just by being aware of it, you're going to change small habits every day.

It's also, maybe not surprisingly, the most difficult thing to do. Looking at the balances. Because when you're not doing well, you constantly are looking at what you don't have. And it's really scary, and it's really hard for people to do. But it's the first step, just to look at it, every day and be okay with it.

What's a financial decision you'd be happy to outsource to an AI agent? 

I always wanted to have a credit card optimization where I have something that automates which card I should use for which activity. I'm a points nerd. Me and my co-founder, Rachel, are both very into it. I would love a tool that automatically chooses for me what spend goes where. 

I think the other thing, I mean it's a little easier, is I am pretty open to it for investing purposes. Not fully. But I did invest in an EFT [using] Claude. I don’t even know how it's performing. For investing purposes, I do the opposite of the advice I gave when looking at how much money you have. I try to be long term and not be too emotionally attached to the short-term outcomes. 

What earns the right to be someone's primary financial relationship? 

There are a few things. So, it's a list, probably. I think number one is you have to have great products that serve the needs. If you don't have great products, then no amount of dressing it up will change that. I think the second part is really being on someone's side, really caring about their long-term goals and outcomes. And the final thing is just being there. 

For me, I choose my financial institutions where it's part science, part art or how I feel. And how I feel when I need to call them. Like, I will think about which credit card we use most based on knowing that if I have an issue with a charge, who's going to make it easiest for me to call up and talk about the issue, or with self-serve, even better if I can do it from the app. But I have certain cards that I can't dispute anything on the app. I have to go call someone and only during certain hours and then I'll think twice before I use that card for certain things. 

How do you define a bank? 

A bank is an entity that helps me save, borrow, and potentially invest. It’s an entity that helps me manage my money. That’s the simplest version of it. 

What's the last thing you bought that you're still thinking about? 

I never regret paying for experiences. Things? Maybe. Experiences? No. So, I bought myself a class pack for horseback riding lessons. And every time I go, it makes me really happy and I feel very good about that spend. 

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