Finding Your North Star with Caleb Silver

Finding your financial north star is critical and requires thought. Caleb Silver talks about knowing what’s valuable and what truly matters!

Mar 28, 2024 | Blogs, Podcast

About the Episode

We focused on finding your financial north star, deciding for yourself what’s true about money and wealth, how to gain control over your finances, why it’s so hard to take a step backwards, and what money’s purpose in our lives is, with Caleb Silver, Editor-in-Chief of Investopedia.       

Listen to hear a difference-making tip on developing the super skill of listening and being emotionally intelligent!

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George Grombacher

George Grombacher


Caleb Silver

Caleb Silver


Episode Transcript

george grombacher 0:02
Hey, I’d love to get us started. Give me two truths and a lie, please.

Caleb Silver 0:07
The truth is that I make some of the best guacamole on the planet of Earth. I am a black belt in guacamole. I honed my skills in the restaurants of northern New Mexico. And I don’t know if I’ve ever had it better. That’s the truth. Another truth is that I like riding sideways. I’m a long border snowboarder, you know, the longer the board, the steeper the terrain, the steeper the hill, the happier I am. That’s an absolute truth. And a lie is that I figured out money completely. I know all the answers. And if you ever have any questions about what to do with it, how to make it where to keep it. I have all those answers. That’s an absolute lie.

george grombacher 0:58
I love it. You’re getting close, though.

Caleb Silver 0:59
I’m getting close. It’s a never ending journey. Learning about money is a lifelong, lifelong journey. And I’m still on the road and I probably will be until I’m no longer on the road. Well,

george grombacher 1:10
I mean, what’s gonna happen is once you figure it out, then they’ll invent something new. They didn’t even realize, like cryptocurrency.

Caleb Silver 1:19
Yep, the crypto crypto of the next century. I can’t wait for it. Or

george grombacher 1:22
something like that. I like it. Well, one of these days, I will get to try that guacamole in the in the Cassina de Silva. Or what was that? Did you have a name for the kitchen last time?

Caleb Silver 1:37
I don’t know if I did. But I’ve worked in many kitchens, but I almost started a burrito truck called Bobby’s burritos for breakfast burritos. Not long before I came to, to Investopedia. But I think the world is a better place that I am not running a food truck. And I’m in a happier place that I get to be the editor in chief of Investopedia. But it could have been very different. I could have been doing financial advice, while wrapping up a breakfast burrito on Sixth Avenue in Midtown Manhattan, battling it out for space among the many good food trucks there. But I think I wound up in the right spot. Yeah, it’s probably

george grombacher 2:08
true. My love it. Well, it’s always good to talk to you. What is what is top of mind for you right now?

Caleb Silver 2:15
I’ve been thinking about the things that I think about when I think about money. What does that mean? I think about money all the time. And it’s not just am I going to have enough? Or am I putting it in the right place? Or how do I make more, I think about my relationship with money a lot. And I talk about money all the time. I’m the editor in chief of Investopedia. It’s a super job. And I talked about it on TV, I talked about it on podcasts, I speak about it on conferences, I interviewed people about it. But when I think about the what I think about when I think about money, I think about my relationship with it, and how that has developed over my lifetime I, you know, I grew up with with means and with parents that had wealth, and then they didn’t all of a sudden. And then it was a constant sort of struggle to try to get it back to get back to what that was. But having it then not having it and realizing how fleeting that could be and the mistakes that people make with it, when they have it. And then trying to get back to that way of living. That did a number on me, I think psychologically, and I think it’s a lot of the reason that I do what I do today. So I think I’ve been thinking I’m in my 50s now I think about things that were going on in my teens. I started working when I was 1213 years old, because I always wanted to control my own income, I wanted to be in charge of it. I didn’t want things to happen to me, I want it to happen to things. So I’ve been thinking a lot about that lately, especially the more times I’m asked to give advice, the more often I have to reflect on where I’m coming from when I talk about money.

george grombacher 3:52
Amen to that. How old were you when your folks went through that?

Caleb Silver 3:56
I was a teenager and it started, you know, pretty much when I was 12 1314 years old. When you thought the things that were absolute in your life. You know, we’re always going to take a vacation, we’re going to live in a nice place. what’s ours is ours. When you when those realities disappear, and they start fading away and you have to reconcile with the fact that it was not what you thought it was or what people purported it to be to you as you’re growing up. It’s a big reckoning you’d have to do not just in the loss of a way of life, but in a way of sort of looking at the people who raised you who I love, but it was a reckoning and we’re still going through it.

george grombacher 4:41
It’s really It’s hard when when I’m presenting to a group of people I’m talking about if you’re not where you want to be financially, how do you make changes can you earn more money? Do you have to live on less money? If I have to live on less? Do I need to cut back Icahn lifestyle, can I take a step back pay off debt, so I could take a bunch of steps forward. But that’s, that’s conscious, that’s I am going to make those choices versus it sounds like that was the opposite for your parents,

Caleb Silver 5:12
right that they didn’t want to make choices wanted to be at a certain standard where there used to be, but the game had changed. And that hadn’t changed with it necessarily and accepted certain realities. And I’m not here saying I was suffering, we were boiling catch up. But going from anything you want to, you’re we’re not sure we can do, we can even, you know, put together that Thanksgiving meal this year. That’s a that’s a, that was a pretty cool reality at that young of an age show, not a surprise that I started working at a young age. And now that I think about the fact that I’m the editor in chief of a financial education website, right, this is truly a position of honor. And I don’t take it lightly. And I’m grateful for it. It kind of makes sense to me. But I was an art major, I was a soccer player. You know, I was a filmmaker, a documentary maker, I never thought I’d be here. But now that I am here with the time and the wisdom to think about what got me here. I know that was because of what happened to me when I was a teenager, and the lessons that I had to learn about money.

george grombacher 6:18
What do you think that? If this is you could tell me if I’m, if I’m asking too personal a question, what did they do? Well, in handling it, what did they struggle with?

Caleb Silver 6:30
The transparency and communication was not good. And I think some of that is shame. I think some of that is not wanting to accept reality, I think something that some of that is not wanting to accept a loss. And I think they could have done that a lot better, and then adjusting to the reality of what our, what our financial life needed to be like, in order for us to get through. They didn’t want to make a lot of those adjustments. So I was making those myself by saying I don’t want to rely on them for these, for a lot of the things that I traditionally relied on them for I’m gonna go out and make my own money and do it that way. They kept a roof over our heads, right? They paid for my education, right, they made sure the essentials of for me to develop and start a career were in place. So again, it’s not as if I was bereft, I had just gone through a financial trauma with them. And we never really process together, I process it together as a family. And now that my parents are, you know, older, and I’m older, and we’re dealing with their financial futures, and that of my own family, a lot of it’s coming back up again. So I’ve been thinking about the way I think about money a lot. And I think it’s totally colored my career. And I think it’s in a good way, because I’m not trying to help people avoid these types of things. But I have conversations, George, with people all the time I do office hours with, with employees here at our company, or when I go visit schools, or when I talk to teachers, who are have real questions about like, not being able to make ends meet, and getting themselves into the quicksand of debt. And how to get out of that and making radical choices to have to solve those problems. It’s so hard for people to, to be able to embrace the fact that what was what once was is no longer and they have to really adjust their lives, if they want to get back on track.

george grombacher 8:23
What is the hardest part of that? It’s there’s tactical stuff, I need to maybe start paying closer attention to my budget. And then there’s the ego that says, What is everybody else going to say and think?

Caleb Silver 8:35
I think there’s the ego is a big part of it. I think people are exhausted when they have to think about, you know, the hard work that goes into turning your life around financially. And you know, you could be somebody, you know, no fault of your own a medical emergency, a loss of a loved one, a loss of a job for one reason or another divorce, you find yourself in a position that you’d never imagine you’d be in. And you have to make very radical choices and being having to accept that, I think is emotionally exhausting for people. And then there’s the ego part of everybody knew me is this and now I’m this. I used to drive this and now I ride a bike, I take the bus that’s hard for people to do, right, that shift to frugality, if that’s what it takes, or I used to, you know, join my friends every Saturday for brunch, but I can’t do it anymore. I can’t afford it anymore. And are they still going to want to be my friend, you know, that people go through a lot of things and I it’s as the person trying to help them and give them advice. It’s also strange because I, you know, don’t look like a person who, who had to go through those things, but I had to have my own financial reckoning to get to this place myself. So and I’m, you know, I’m the editor of Investopedia. So people are willing to listen to me. But I also know like I talked to some people, you know, single moms, you know who went through a divorce and they’re facing a financial emergency, I’m never going to be a single mom facing a financial emergency. But having being able to help them practically, but not be able to walk in their shoes, that’s hard. You know, that’s hard for me to get over, but I have to get over it because I’m here to help.

george grombacher 10:15
I imagine when you share a little bit about your story, in those experiences, it makes you more relatable, and probably more effective.

Caleb Silver 10:24
I think it is. And it’s a vulnerability, and I’m willing to talk about it. Now, for a long time, I didn’t want to either, I wanted to hide the fact that this had happened in my family, or I wanted to be the guy that had everything under control, you know, looks like you know, what you’re doing, you know, and I can look like I know what I’m doing. I go on TV all the time looking like I know what I’m doing. I don’t know what I’m talking about. And, you know, for me, it’s, I put a lot of work into that because I want to be giving, you know, the right advice, I want to be sending the right message about building wealth about avoiding debt about living your life, in a financially responsible way. But most importantly, and you’ll appreciate this, given your career, it’s helping people figure out what it costs to be them and what it costs to be the them they want to be and how do we get from this, who I am today to that, which mean I want to be or my family wants to be in the future. That’s planning, but it’s also education. And so I’m sitting right in the middle of a lot of that.

george grombacher 11:23
Yeah, I appreciate that. I wrote down morning, and the stages and the processes of mourning, because just going back to if I was in a position where I was financially successful and affluent, then all of a sudden I’m not. I imagine it’s a similar process, as losing a loved one.

Caleb Silver 11:45
It is and but you also realize, I think going through that if you’re, you have some self awareness, like what is actually important and what isn’t, you know, I get asked all the time, I do a lot of work in public schools and high schools and talk to students throughout New York City and across the country. And I always ask them, you know, to ask me any questions that you want. And inevitably, somebody says, Are you a millionaire? How much money do you have? Are you really rich? And then my answer always is, it’s really not about how much you have, it’s about how much you keep. It’s not about how much you make, it’s about what you keep, and how you can grow that money over time. But if you ask me what my most important, most valuable assets are, it’s my friends and my family, I’ve had friends for 45 years, who are still some of my tightest people. And that, you know, you can’t put a price tag on that. So, you know, went from flying first class and maybe getting picked up in a stretch limo to, you know, you know, 36 B by the restroom and the back of the plane, you know, for both flights, and, and figuring it out. Now, again, first class problems, I understand that are people dealing with a lot worse. But, you know, being able to actually understand what’s valuable in your life, that takes a long time for people to come around to. And luckily for me, I had the financial trauma at a younger age, where I learned those lessons pretty quickly. But I also learned the value of hard work and what it means to, you know, to earn your keep, and then have your keep start working for you.

george grombacher 13:21
Think that that’s that’s, that’s really powerful. And just how you started a conversation, thinking about what you’re thinking about, and contemplating what’s valuable. What What matters to me. Is that an obvious thing for people that is that obvious that we should be asking ourselves that question, I just feel like, like I certainly didn’t, until I started asking myself that question.

Caleb Silver 13:45
Yeah, it is. But it takes people a long time to come around to look I went to, I went to a private college, in upstate New York, had a great education, I was a soccer recruit, I didn’t have the grades to be there. But I had the skills to be there at least to get in. And I was around a lot of wealthy people with the houses and you know, you know, Montauk or Cape Cod or the ski houses and Telluride and Aspen. And, you know, we came, I came from family that looked like it was going on that was on that path and wasn’t not at all. So being around, you know, keeping up with the Joneses, so to speak, isn’t easy, or in my case, keeping up with the Chad’s, the brands and the theaters, the thirds, that wasn’t so easy, because you’re around wealth and you know, around, you know, generational wealth where they had played the game, whatever that game was that right way and had built wealth and weren’t experiencing, you know, financial trauma or the authorities coming to your house to seize assets like it was different and wanting to, you know, what was it like to be in that family where you didn’t have to think about those things. That’s tough for a lot of people and as a teenage, as a teenager in America, you know, in the late 80s. It was really intense. And I’m sure it’s no easier now, especially with social media, everybody’s flaunting their drip, and they’re playing and living their best life. And you’re literally just trying to get by and afford groceries and afford your own apartment, you know, for the first time if you’re a young person trying to make it in this country, so it’s hard, it’s never been easy for people to come to that reckoning. And hopefully, a lot of people don’t have to go through the trauma to get there. But it’s not like anybody ever taught us any of this. In high school, George, like we were learning trigonometry, when we should have been learning, you know, good credit versus bad credit.

george grombacher 15:33
Yeah, yeah. That’s, that’s, that’s exactly right. So to motivate people, to inspire people, to encourage people to start having those kinds of inner dialogue, like what really does matter, what is a value to me, is, is a really nice car of value to me, really? Or is this? How do you How would you coach up those kids that you talk to, to start thinking about that?

Caleb Silver 16:02
Well, when you ask kids, and my kids are no different, you know, what is the purpose of money? Why do you want to be rich? What is the what is the meaning of wealth? I was just sitting with a friend of mine over lunch. And I said, What is the thing that you do that makes you feel wealthy, even though you might not be as wealthy as you thought you might want to be at one point in your life? What is the thing you do that makes you feel that way? And he said, and this is a good way to think about it. I do not skimp on my health. I do not skimp on taking care of myself. There is one me? Right? I feel

and eating healthy working out like that’s well. So what is the meaning of wealth? What does it mean to be wealthy? And I think when you ask most people, that question may have a number in their head. But the number is just a number. It’s the you you want to be that they haven’t done the thinking about right. And I think people need to think about that. What does that mean? Do you want money so that you can go anywhere you want to vacation? Live in a suite apartment? Drive three or four different cars? Or do you want money that so you can give money to other people? Is it a charity thing? Is it all of these things, when you think about what the purpose of money is in your life, then you can actually dial it, build backwards and get to the number. But most people say 25 million liquid and I’m good. You know, I know I’ll live off the interest. And I can go anywhere I want. I can fly private and all those things. It’s like, okay, but what we really haven’t talked about is, what’s the Northstar in that, right? Money is just a tool for you to live the life the way you want to live to buy your time, effectively, the smartest financial planners and advisors I know, and we’re friends with a lot of the same people. They say that to you, they say, money is just a tool that affords you the ability to bide your time to do with what you want. So what is it that you want? That’s the question, people need to ask themselves, the people who are trying to build wealth. And there are plenty of people that we know. And plenty of people you don’t know, that are not just trying to build wealth, they’re trying to get out of debt. So get out of debt so that you can have a little bit more financial freedom. So you’re not stressing out every month that you’ve missed a credit card bill or there’s a note on the door about the utility bill, right? These things work both ways. What’s the Northstar? In those conversations, and I don’t think people examine that as much as they think about, I want to be like him or her, I want to have this number, I want to have that vehicle, I want to be able to buy that watch. Versus I want to be that person that has the ability to make those decisions without it being stressful to me. And that is a different conversation than I wanted this. Right or that it’s i i want to be this person. And then let me find the number that that adds up to that person.

george grombacher 18:49
Rested peace Daniel Kahneman talks about Thinking Fast and Slow. And sometimes I think $25 million in a Ferrari. That’s the fast part of my brain. The slow part is what you’ve been talking about what is really my Northstar? It’s cool that I want that stuff. And it’s okay. But what is it really mean to me?

Caleb Silver 19:07
Right? What is the what is the purpose of money in your life? Yeah, I have a family you have three kids now to, you know, being able to give them the, you know, a life where it’s comfortable, but they’re also well fed. They’re aware they can go to good schools, you can take him to see the world. They learned about other people like there’s you have priorities, you know, as a family, I’m sure that you think about and you know, all these things cost money and you got three kids that might want to go to college one day, I’m in the process of about to send my second off to college thinking about that financial exchange, you know, what’s worth it these days? How do we determine what’s worth it anymore? It’s very it becomes very interesting. That’s why it’s lifelong, right? We go through these different life stages and their financial questions and the and the the The puzzles we need to solve about the role of money in our life just become more complicated and morph into new things.

george grombacher 20:05
I love it. Well, Caleb, I always appreciate your time and your attention. We are ready for your difference making tip today, what do you have for us?

Caleb Silver 20:16
I think the thing that I keep coming back to is the ability to listen, right? I was just interviewing Charles Duhigg, he wrote a book called Super communicators. He’s a Pulitzer Prize winning author, a very respected journalist and business journalist and his book, super communicators was one of the smarter books I’ve read in a long time. And it’s about those people that we all know, that have that ability to communicate at a higher level that blackbelts in communication, and they’re not the best speakers in the room, necessarily. They’re not the leaders or the captain of the team, or the CEO, so to speak. But they have found a way to find harmonic conversion in conversation, because of their ability to listen, and to empathize. And to ask the right questions, know when to talk and know when to listen. So if you’re developing a super skill, I don’t care what line of work you are in, the ability to listen well, and be present. And be empathetic, is invaluable that will get you more than the ability to work in AI or Python program or know how to drill for oil or gold. The ability to listen well is a super skill, and it will be invaluable to you and your life and career. Well,

george grombacher 21:39
I think that that is great stuff that definitely gets come up. I like to think about that if it’s superpowers that we have as human beings and I think that you could definitely classify that as a human superpower or certainly a super skill, as you said, love it. Well, Caleb, thank you so much for coming back on the show. Actually coming on the show for the first time. Where can people learn more about you? How can they connect? Yeah,

Caleb Silver 22:02
I am at Caleb silver, just the way it sounds ca le BSIV er on all the socials, and I am the editor in chief of Investopedia so at Investopedia we are a website that’s going to be 25 years old this summer. GEORGE That’s 250 Real years 25 years on the internet is 250 So we are we are a dinosaur but we’re still roaming. And we’re still here giving out free financial education and literacy. We will be here hopefully for another 25 but we’re at Investopedia I’m at Caleb silver come one come all and it is always a pleasure to speak to you I’ve read a few

george grombacher 22:36
jobs as much as I did. So Caleb your appreciation shared today share with a friend who also appreciates good ideas find Caleb all over the internet social media at Caleb silver ca le BSI LV er, and for all of your financial questions, needs education, go to follow them on social media as well. Obviously been singing their praises, not for 25 years but for certainly a long time. So thanks again. Caleb. Thank you. Finally, a friendly reminder there’s never going to be anybody more interested in your financial success than you are. So act accordingly.



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