How to get better at money, with Carrie Joy Grimes

0:00Hey, folks, Jeff Berman here. Exciting news. Applications are now open for the Masters of Scale Summit. It's happening October 20th through October 22nd in San Francisco, and it is a really special event. Please join our curated community of founders, innovators, and leaders shaping the future. Expect ideas that challenge your assumptions and connections that move your business and maybe even your life forward. It's an experience that can change literally everything. Apply now at mastersofscale.com slash apply26. That's mastersofscale.com slash apply26. Here's something all founders know. Every dollar should be working for you.

0:49So why is your biggest monthly expense, your housing payment, just sitting there? Built is the membership for where you live. Whether you're renting or paying a mortgage, every payment earns you points you can redeem toward flights with United, Lyft rides, Amazon.com purchases, or even a down payment on a home. Built members also get access to a neighborhood concierge. It can book restaurants, fitness classes, and find new local hangouts, all while being rewarded at more than 45 ,000 merchant partners. It's like a personal assistant built into where you live. Join the membership for where you live at joinbuilt.com slash scale.

1:25That's J-O-I-N-B-I-L-T dot com slash scale. Humans will never be more intelligent than AI. There's going to be two types of companies. Those are great at AI and those that went out of business because they weren't. How do we build a future that is human-centered? I'm Rana Elkawiyubi, and on my podcast, Pioneers of AI, we answer that question and so many more. As an AI scientist, entrepreneur, and investor, I know what it takes to build AI that works for everyone. Every week, I sit down with the pioneers shaping our future, and we take you behind the scenes of the AI that's transforming our lives.

2:10Find Pioneers of AI wherever you tune in.

2:18Money is math and feelings. But having had thousands of conversations with individual people and having had the experience at work money of being in conversation over text, email and phones with 9 million people all the time, one of the things that became very clear is that the thing that holds the most people back is the feelings part. This is Masters of Scale. I'm Jeff Berman, your host. This week on the show, C.J. Grimes. C.J. Grimes is the founder of Work Money, which helps 9 million and more growing number Americans deal with personal financial issues, has a fascinating history and is also a dear friend with a big new book coming out.

3:08C.J. Grimes, welcome to Masters of Scale. Thank you so much, Jeff, for having me here.

3:16So why don't we just start with like what is work money and how did you get started doing this? Work money is the thing I wish existed when I was trying to figure out money. It is a nonprofit. We've got 9 million members and we help people figure out how to earn more and save more and spend less. And we do that through programs and services and coupons and discounts, kind of like the AARP. The other thing that Work Money does is we figure out how to use the power of 9 million people to bargain for cheaper stuff, to make sure that people understand how the economy works and what they can do to navigate it.

3:52And it started in COVID. You know, it was 2020 and everyone's money kind of got turned upside down. People were trying to figure out what are these stimulus checks? What's a PPP loan? What is unemployment? And I put up a website to answer all the questions that I was getting from people. And it just took off. And then after COVID, it became pretty clear that there wasn't one place everyday Americans could go to figure out what to do with their money. Like not one trusted website brand person who you could really lean into who would give you the straight information. And that's why we are not done after COVID.

4:26That's why we're now 9 million people and we're growing pretty rapidly. What in your background led you to not just identify this need, but say, oh, I'm actually someone who could really help with this? I was a union organizer for just about 20 years, and I had this incredible gift of talking to working people at their homes, at their churches, in bars, in union halls, and just asking people about their money and their lives and figuring out how to help folks negotiate for higher pay and better benefits. So I got to see what happens when regular people kind of get together and they put their shoulder to the wheel of doing better.

5:00And there was a very obvious set of problems that emerged after thousands of conversations. Thing one was that most people didn't really have the money basics down. Like nobody sat me down and taught me how to do money. And then the other was most people felt like they were kind of in on all of it by themselves. Like they were just alone having to navigate it. And so when I put the website up, I had a really strong sense of what I needed, which was help with the basics of money. But then also the idea that we really can change the circumstances that we're all trying to earn more and save more in.

5:38I very much want to get to the scaling of work money. Zero to nine million in five years, basically, is a pretty impressive number. And these are people you have a text relationship, an SMS relationship with not just people like 9 million visitors to a website or, you know, an Instagram or something. But before we get there, what led you to the union organizing work to begin with? You know, I'm a pretty cantankerous person. I don't like it when people have a bad deal and they can't fix it. And, you know, I was in college. I was a history major and I went to Northern Illinois University. Go Huskies.

6:12And I got really into how we improved America over time. Like, how did it get better? And it wasn't magic. It wasn't nature. People got up and decided to shift things over and over again. And I was lucky enough that somebody who I went to college with was like, you know, you might make a good union organizer. And I was like, unions? Those old things that, like, people need when they work in a factory? But I was like, okay, you know, let's check it out. And so I moved out to Ohio where this local union was organizing workers. And I said, okay, I'll try. And I hated it for the first 90 days. What did you hate about it?

6:53It was really hard. Like really good organizing is listening. And I really liked to talk. And so I had to learn to listen first. One of the things that struck me reading the book, It was 20 years working with working families, paycheck to paycheck voters, etc. Gives you incredible grounding for the work you're doing at WorkMoney today. And also, you have some pretty extraordinary personal stories that help you relate to the 9 million and growing number of Americans you're serving through WorkMoney. You reference moving to Ohio for the first union job. There's a story in the book about the boss you were working for effectively at that time.

7:34Would you mind sharing that story with us? No, I wouldn't. When I moved out to Ohio, I had negative money. I mean, I really had no money. I had shoes with holes in them, and I had my rust bucket of a car, which is literally what I call it in the book. She barely got there. She had a name. Her name was Mo. I called her Mo. She barely got there, and it was like, please don't die on the road. I mean, we've all lived those years, or not all of us, but many of us have lived those years. If you know, you know. And I show up for my very first day at work, and we're at this Union Hall office, and we're doing a bunch of stuff.

8:08And then the organizing lead says, well, let's go out to dinner, and we'll sort of finish up the night. And I didn't have any money. I was, like, going to go back to my Red Roof Hotel and get some, you know, ramen noodles and watch Law & Order, which is the only thing on the television in hotels at that time of night. And the organizing lead was like, no, no, you got to come to dinner. And I was like, that's OK. And he like knew. He knew. He saw those holes in your shoes. I was so threadbare and I was so obviously like strapped for cash. He's like, I got you. And oh, my God, I hated that. He was like, no, no, no, you got to come.

8:46And he couldn't say no. He was like, I really wanted to impress him. So we have dinner and he pays for my dinner. And then he gives me$100. And he says, here, buy some new shoes. And like give yourself some cushion, basically, until the next paycheck. Yeah. And let's be clear, like$100 also 20 years ago when you have your next paycheck isn't coming for two weeks. Right. Right. You've got absolutely nothing. Like that is God send money. But also, how the heck do you pay that back? I mean, this is the question. This is part of why this book even exists is because, look, I tried budgeting here and there.

9:20You know, we all had. I kind of like I'd had a bit of an emergency fund and then I'd kind of spent it all on an emergency. and see, and then hadn't figured out how to fill it back up. And this was the first time I was so aggravated that I owed this man money. It just ate at me. So I sat down in my red roof hotel room, and I took out a pen, and I wrote down all of the money I had to pay for things, how much I was going to make, and I was determined to pay him back. That sounds suspiciously like a budget. And it was my first real budget to this day. The way that I figured that out has become like my method for budgeting.

9:55It's not rocket surgery. It's like, here's what you got to spend and here's where the extra money can go. And so I paid him back and I just had this feeling of accomplishment. And this is the thing that I realized I had been telling myself. I was terrible at money because I was poor and I was working poor. And I was like, I couldn't keep it in my bank account. I was living paycheck to paycheck. I'd had these moments, which some of us have had, where you go to the store and you give them your card and you're like, I hope it goes through. And I just assumed that all of that was evidence that said I'm bad at money.

10:27And the reality was when I thought I was bad at money, then I behaved like somebody who was bad at money. And I kept behaving like somebody who was bad at money. And that moment where I paid this guy back and I felt like I'd really done something with my money. And I decided in that moment to change the way I thought about how I did money. And I thought, wow, I can be good at money. I really can. And then I was like, well, if it worked for that guy, I should pay down the credit card debt that I've got. I should save up an emergency fund and so on. And I did. And every time I found myself thinking I couldn't do it, I'd be like, of course you can be good at money.

11:07So, I mean, I go back to my first job out of law school where I went to be a public defender rather than going to a big law firm and making an insane amount of money. And I made$29.5 that first year out of law school. And the local Safeway would triple coupons on Sunday nights after 9 or 10 p.m., whatever it was. And I would literally wait for the clock to strike so that I could walk up to the register and get that triple coupon value and buy my huge thing of chicken thighs, which I'd have to stretch out to make the week. Like the idea of setting money aside at that time was like insane for me.

11:42How did you do it? Let me be really clear. Most people, the problem they have is that they don't have enough money. I just want to say that plainly. It's a math exercise. It's a math problem. Yep. And in this economy and in our society, you play the hand of cards you're dealt no matter what they are. And I think holding both of those realities together is hard. And so I say this without judgment. I chose to, for myself, say, I choose to do this. It is important to me to pay this guy back. So it took me longer than I would have liked to save up$100, but I did it. And the choose to, not have to thing was really helpful for me.

12:17But I also worry that I don't want people to weaponize it. There are several personal stories from the book that were quite powerful to read and felt formative. There's a story about when your mom is passing, which feels really foundational. And so I was wondering if you could share that as well. Yeah. My mom, bless her heart. She died in 2022. I'm going to say some things that are a little hard about my mom. And just to pay for that a little bit, I'm going to say she was so smart. She was a card strike. She was a very Christian woman who believed it was her God-given right to cheat at cards and beat you any way she could.

12:52She was a huge Cubs fan and a Bears fan. And she lived long enough to see the Cubs win the World Series. And my mom died in really shocking conditions. By the time she passed away, she had been living on Diet Coke and cheese and crackers because she wasn't sure how much money she had. So she had been spending nothing on like the barest of like sustenance living. And her house was filthy and everything she owned was set out at counter level because her health had deteriorated from her lack of nutrition and mobility. So she couldn't really bend up or down. And so she fell and then we moved her into rehab and then an independent living facility where she passed away pretty quickly after we moved her.

13:35And what I realized is that my mom had been living this like kind of pauper's existence and she'd been afraid to go to the doctor. She hadn't been taking her medicine because she was afraid she couldn't afford more. And so the end of her life, she just, her world got so small and she was so afraid that she wouldn't have enough, that she did nothing. And I, to this day, I know that if, like, if my mom had called me 20 years ago or even 10 years ago, I could have sat down with her, looked at her money, figured out maybe some in-home help for her. We could have budgeted differently. We could have, I could have helped her think through what the end of her life could look like.

14:13It was hard in the moment. And then the reflections afterward were really, like, it was very, like, oof, I don't want my kid to go through that or my husband and also me. Like, I don't want to go through that. But I wanted to make sure that other people's moms and other people kind of maybe didn't get to the cheese and Diet Coke and crackers stage. Yeah. And it's such a moving and powerful part of the book. One of the more mundane, but for me, really striking elements was even people who are not in the financial circumstances that your mom was in can have a lot of issues around money. Oh, my gosh.

14:50Yeah. A lot of fear can be avoidant. I'm an avoider. I mean, the book really helped unstick me on a couple of things. I've just been like, I don't want to deal with it, so I'm not going to do it. And it's like, f***. I have to do this. Yeah. Right? And so why do so many of us have so many issues around just facing the facts and dealing with the matters, the basics of our personal finance? Money is math and feelings. It's math and feelings. Math plus feelings equals money. Math plus feelings equals money. Got it. But having had thousands of conversations with individual people and having had the experience at work money of being in conversation over text, email, and phones with 9 million people all the time, one of the things that became very clear is that the thing that holds the most people back is the feelings part.

15:38You know, that's the part where you go to Target and you go in for like, I don't know, pick a prescription and you walk out with like peanut butter pretzels and a throw pillow and that really cute little solar lantern that you're like, this is going to look perfect on my back porch, but it wasn't really in the budget. But you really wanted it and I'm just going to do it anyway. That's there's nothing morally wrong with doing that. But I got really curious, like, well, why did I do that? Like, why did I? I knew I know I have a budget. It's not in there. Why did I? Why? And for me, it would usually be I had a hard week.

16:07I felt like there's no joy in life. I just needed some bit of pleasure in my daily week, which is a note that I need to figure out some pleasure in my week. Or for me, avoidance was also, I cannot stand evidence that I might not be good at this. So I would just not want to open the envelope or look at my bank account. It's like, I just don't need one more person telling me that I'm doing a bad job at something. Because there's a story in my head that runs pretty hard telling me you're doing a bad job, you're doing a bad job. This is obviously in the past. And so the feelings part is part of why, when I, in the book, the very first chapter is figuring out what your money story is and what you want it to be.

16:46Because that's the thing more than anything else I've seen make it hard for people to implement all the math.

16:54Still ahead, how CJ Grimes is scaling work money into a movement.

17:08Whether you rent or own, your housing payment is probably your biggest bill of the month. So here's something worth noting. Built is the membership that actually rewards you for it. Every housing payment earns you points that you can redeem toward travel with partners like United, along with stays at Hyatt Hotels, Lyft Rides, Amazon.com purchases, and more. And the Neighborhood Concierge feature can make restaurant reservations, book fitness classes, and finds you local spots, all while racking up rewards at 45 ,000-plus merchant partners. So whether you're paying rent or paying a mortgage, Bilt works for both.

17:43Join the membership for where you live at joinbilt.com slash scale. That's J-O-I-N-B-I-L-T dot com slash scale. The very best founders I know are brilliant at building systems. They connect teams, they remove bottlenecks, and they eliminate single points of failure. And yet, when it comes to their own wealth, most are running a disconnected stack. A tax accountant here and a state attorney there, a wealth manager who doesn't talk to either one of them. Creative planning was built to fix exactly that. One integrated team of tax professionals, state planners, investment specialists, all coordinated by a dedicated wealth manager who sees your full financial picture and keeps every piece working together.

18:33Proactive tax efficiency, estate strategy, investments all under one roof. Creative planning where wealth works together. Learn more at creativeplanning.com slash mastersofscale. Hey listeners, Bob here. If you listen to Rapid Response on Masters of Scale, you may be missing half the show because every Friday we release a second Rapid Response exclusively in the Rapid Response feed. The guests and topics are just as compelling and timely from Ford's CEO to NASA's administrator to the lessons from the Devil Wears Prada. It takes about 10 seconds to find. Just search Rapid Response wherever you listen to podcasts and hit follow to make sure you never miss an episode.

19:21I hope to see you there. Welcome back to Masters of Scale. You can find this conversation and much more on our YouTube channel. And be sure to check out the show notes for a link to our newsletter. Let's talk about WorkMoney. What happens that this goes from being sort of a project or a side hustle or something that might have potential to something that starts actually scaling? I thought when the pandemic was over or subsiding, that we would see interest subside, that our signups would drop. This was meant to be like a, let's get us all through something hard and then let's see what happens. And it became, I mean, to be blunt, I'm also a person who believes in organization.

20:02And so, of course. 20 years of union organizing will do that for you. I wanted to build something that would be sustainable, but I was aware that this was launching to solve an immediate problem. And I had been thinking about sort of the concept up till this point. Like I've been thinking about the concept of work money, but work money was really meant to patch a hole in the moment. And then the test for me was, well, for all of us was, okay, once the pandemic is over, do we see traffic drop? Do we see sign-ups drop? And it turns out, no, because the economy hasn't really gotten dramatically better for most of us.

20:34Yeah, no. I mean, there was a chart that you and I were looking at this weekend that showed like basically the delta between where the stock market is and where Americans, how they feel about the economy has literally never been larger since they've been measuring this. That's right. That's right. Look, there's always going to be those of us who get dealt a hand and have a really hard time getting into financial security in the American economy. Like I'm I'm I'm very aware that that is that's that has been a story for some people perennially in the American economy. But the number of us who feel squeezed in today's economy, who make very good living, who are watching health care costs, education costs, housing costs, child care costs go up so much faster than our wages.

21:14Yeah. It's staggering. And when the pandemic ended and our signups went just as fast, if not faster, and right now we're seeing a lot of signups because middle class families are stretched. It was a real clarion call after the pandemic. It's like, okay, this really is about, for me, this is about how do we build a permanent civic institution in America? A place that anybody can go to get the individual information about money, how to save, how to invest, how to learn about buying a house or not. And then also, how do we use our collective strength to bargain for better in the market, to make sure that decision makers who are politicians know what everybody wants?

21:58This isn't about political parties. It's about right and wrong. And how do we think about using all of our resources to build the businesses that we want? And I feel even more passionately now than I did during the pandemic that the problem isn't just a one-time crisis. You know, I mean, that was a particularly gnarly one. But there's a need to shift how the economy works right now and to make more success more possible for more people. On the road from zero to nine million, were there inflection points you can point to and go, oh, that really changed? We hit a scaling moment there. We started in the pandemic, so we're fully remote.

22:35We're still fully remote. And that moment when you go from one Zoom screen to like two, do you know what I mean, where you have to like hit the little arrow, that was a big deal. Because it meant that we had gone from like passionate generalists to passionate generalists and experts in some things. It meant that also a lot of things I was doing were leaving my hands. And I'll just confess, like as a founder's founder, I really love solving hard problems all by myself. and I am very lucky to have an incredibly talented team that can do a lot of work, but also can give me some grace as I learned to let go.

23:14So me, I don't want to make this about me, but me learning how to like let the team take things was great, was a moment. And then I'll say figuring out how to deliver dollars in people's pockets in a material way and realizing that one, solving, this is kind of antithetical to how some startups work, defining the problem in a very specific way where it's like one kind of problem. So for example, we could have decided, you know what, the problem we're gonna tackle is car insurance costs are too high. We're gonna focus on that. We're gonna be really narrow. We're gonna be like, okay, we're gonna talk about car insurers and how they can do better.