Caleb Silver: College memories, finding love in South America and defining the financial universe as the Editor in Chief of Investopedia

Press Profiles: What's their story?

Caleb Silver began his journalism career hunting down stories in his home state of New Mexico with a Beta-cam and a lot of hustle. His determination to cover stories and see the world eventually took him to South America (where he would not only find work, but his future wife too), Bloomberg, CNN (where he helped create “The Situation Room” with Wolf Blitzer) and now Investopedia, where he oversees content at the unofficial encyclopedia of finance. Russell and Caleb talk about the vast reach of Investopedia, how the platform has evolved, the secret to making great guacamole, and longboarding in Manhattan. They also reminisce about life in college where they first met a few short years ago. All that, and a whole lot more, on this edition of Press Profiles.?

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?Russell Sherman

Hello again, everybody and welcome to Press Profiles. This is the podcast where we flip the script on some of the top members of the business and finance media. They’re used to conducting the interviews, here we're going to turn the tables and they're on the other side. Talk about their backgrounds, how they got into the business, their favorite memories, career challenges, all sorts of other good stuff. Today's guest is a fun one for me. I met this guy in a college dorm some 30 plus years ago at the one and only Colgate University and since that time, we've crossed paths a number of times in the media business, and now he sits at a top Investopedia, the site that serves as the encyclopedia for all things business and investing. I'm talking about Caleb silver, editor in chief of Investopedia. We're going to talk about his career where Investopedia has been, where it's going, his interesting array of hobbies, some memorable personal stories. We'll cover all that and a whole lot more, here now is Caleb Silver on Press Profiles.

Caleb Silver

Good to be with you, Russ. Wow, this is an honor and a treat, just to be able to chat with you for as many minutes as we have – that's just the win overall. Great to see you. Great to be with you. Go Gate. Let's do this. Bring it on.

Russell Sherman

We go back. It's good, right? Long time since Stillman Hall...

Caleb Silver?

Yeah, deep into the 80s.

Russell Sherman??

We will wait to bore people with all the Colgate talk until the end of the podcast, so we'll actually start with some other topics before we get to that, but don't worry, we'll get to that. You're in South America now, in Argentina. Didn't you begin your career down there? And, tell people what brings you back there.

Caleb Silver

It was an interesting pivot in my career that happened when I came down here when I was about 25 years old, but it didn't just change my career, it changed my life. I met my wife down here, acquired a family down here that's vast and wonderful, and just became a huge fan of the river plate, so I'm in Buenos Aires right now, my wife's from Montevideo, Uruguay, we're heading there soon, right across the river here. This place has just been so special for me, and I have so many special memories, and they're all good. I got married down her, I had a huge wedding, bought a bunch of friends. This place is really close to my heart. I've also fallen in love with Buenos Aires, I’m a Montevideo guy because that's where I met my wife. Got a lot of good friends here, and I just love the city too. So, I am in the city of Buenos Aires.

Russell Sherman

How many times a year do you get down there?

Caleb Silver?

I haven't been down here in several years for various reasons. I couldn't travel down here, obviously over the last couple of years – my wife did come down a few times – but I’ve probably been down here 12 times, maybe 10 to 12 times, and I spent a good amount of time here after I first met girl who was my girlfriend who became my wife, doing some work down here, and we can get into that later, but my journey brought me through here.

Russell Sherman

Yeah, well, I'm curious, what first brought you down there?

Caleb Silver

When I was about 24 years old living in Santa Fe, New Mexico where I grew up, I was running a restaurant, but I had started a video production company, I really wanted to get into documentary producing, and I was doing that. I was doing nature documentaries, environmental educational documentaries, I was doing some stringing for the news. I bought myself a beta cam SP – Russ, you know what that is…

Russell Sherman?

Nice. Yes.

Caleb Silver?

…old school TV camera, real heavy with the big Anton Bauer bricks and a tripod, and I taught myself to shoot. I knew that if I knew how to use the tools of our trade – journalism, video journalism – I could find my way into the business somehow, and plus, I wanted to be a storyteller, I was a huge documentary fan, I was a huge movie fan in general. So, I did that, I started that on my own while I was running a restaurant and trying to make ends meet on the side. When I was about 24-25 I had one of those vision quest moments where I said I gotta get on the road, I gotta get out of this restaurant A, and B, I want to hit the road and see the world, so literally planned a trip. This is kind of pre-internet for folks out there that are… wanna date this with faxes and phone calls and set up a journey from Mexico City to southern Chile working with environmental organizations, where I would come to wherever they were had a campaign going on, and I would shoot footage for their campaigns and try to help them build their own documentary. So, I was trying to help them create content and all I wanted was room board and the experience. So literally set up business with places like Conservation International in Costa Rica, Amnesty, Peace Corps, Greenpeace down in Brazil, ancient forests international in Chile…set up correspondence and then went to these places: hitchhike, rode buses, road boats, however, I could get down to one campaign to the other – that's how I came down through here. But if you really want to know and I don't want to take too much time on this, but it's super important to what happened to me. When I was coming down here through the river plate through Argentina and Uruguay, my father said to me, “Hey, if you're going through Uruguay, you got to hit up our friend Izzy Porzecanski, Ignacio Porzecanski. Ignacio Porzecanski, Russell lived with my father's family in 1961 in Knoxville, Tennessee as a foreign exchange student. So, they remained friends and I always knew about him. He was legendary in our family, I met him when I was really young, and he was from Montevideo, Uruguay. So, they became really good friends and in ’61-’62, their parents stayed in touch, our grandparents, and develop this friendship over the years. So, my dad said, if you go through the River Plate, you got to call Izzy stay with him for a couple of days. Sure enough, I called him or faxed him or whatever we did back in the day, come through, come through Montevideo, stay in our apartment if you want, stay as long as you want, because he had stayed with my father's family for a year, so this is reciprocity coming around. So I did, I took the, I remember very clearly, probably about, I don't know, 25-26 years ago, taking the bus from Buenos Aires all the way over to Montevideo, that's a long bus ride, and then arriving at the bus station, and I thought he and his wife, Martha would pick me up, but I remember my father saying Izzy’s wife is one of the most beautiful women in the world, so I get off the bus, I got a huge Afro, I stink. I've been camping in volcanoes and in Chile, and IN Verloche (?). And there's this beautiful woman sitting down there looking at me, and I’m looing at her, but there's no way that's his wife. Sure enough, it's his daughter, Ana Luz,, who he had sent to pick me up, and that is now my wife. So, we met down here because I was doing that journey through Central and South America shooting documentary footage, met the daughter of a foreign exchange student that lived with my father's family, fell in love, married, and here are 21 years later, we're still married and have a couple of beautiful kids.

Russell Sherman

I love those connections. That story in itself probably gives everyone who's listening a pretty good understanding of who you are, in terms of being adventurous, showing initiative. I mean, that's a big deal, by the way, for you to purchase that, no one else will even think that this is important, but you and I do, purchase that setup that you purchased to start doing news broadcast quality, filming, at an early age shows a ton of initiative, and quite frankly, a little bit of hutzpah that you could go out there and do that and really create something from nothing and then be willing to go out there. Wow. And then that connection, that it was your dad's, foreign exchange student of your dad, and you ended up marrying the daughter. How thrilled was your father?

Caleb Silver

Thrilled. But my mother, when I called her from down here, you know, I fell in love with this woman only took a couple of days or a couple of weeks, I should say, but when I called home, they could hear it in my voice. They're like, how's it going? I was like, oh pretty good. And they're like, what's going on? And I told them on the phone, and my mom said, don't eff this up, this is a 35 year old friendship, we go deep with these people, do not mess this up shatever you do, she knew me pretty well at the time. And I was like, don't worry, don't worry. Anyway, so it worked out, and the families, we jive together, and it's just been great bringing the families back together and then growing this big family, this extended family that I have here and my family up in the States, of course. So, we love those types of connections, and that's the kind of woman she is, and I'll tell you what, you're right, buying that camera was a big deal, took a lot of tips from waiting tables Russ, and I wasn't afraid to do it but I knew I needed to do something, and I needed to put myself in a position where I had some sort of something to offer the industry and up in New Mexico – again, this is pre internet days – there wasn't a bureau for the news in Santa Fe, they had taken all the bureaus out there and all in Albuquerque, which is the bigger city, so I was very much a hustler myself, reading the paper, trying to read the wire, see what was going on. Then I would call the news stations and say, Hey, there's something going on up in Espanola or up in northern New Mexico – Do you want me to go cover it? I can go shoot that footage and drive it back down to you in Albuquerque and you could have it for the six o'clock news. So, I was cutting those types of deals and I became the stringer in Santa Fe which taught me A, how to be a TV journalist and B how to hustle your way into the industry, and you have to – you've been in it, you know, you got to keep going.

Russell Sherman

So resourceful, and such initiative. In 98 you land at Bloomberg, your first sort of, I think, real media job. How did you break into it at the time?

Caleb Silver

I went to NYU School of Journalism, now the Carter Institute of Journalism, shout out to NYU, to the violets. But, this was after my journey through Central and South America shooting footage. I ended up doing some work for Spielberg's Shoah Foundation, shooting Holocaust survivor interviews down here in South America and the River Plate, we'll get to that later if you want. I knew that I wanted to become a better storyteller. I knew I was good with the camera. I knew how to shoot, I knew how to edit, that was useful, I could go get a job if I wanted to. But I was really into the storytelling where I wanted to become a journalist, real journalist, and you know, you're a journalist – once a journalist always a journalist – it's more a craft than anything. It's like being a chef – you don't need to go to journalism school, but the more you practice and the more you get those hours in, the better off you're going to be so I wanted to go to J school. So, I at the time applied to NYU, my wife applied to Columbia, we wanted to move, she was here in South America and Uruguay. We wanted to live together in the city and go to grad school. She got into Columbia, I got in NYU, and then I traded that equipment that I bought Russell, for tuition for one semester, two semesters, and I got the other one because I worked there. So I traded that, and NYU, the School of Journalism had a very tight connection with Bloomberg Television, which was just in its early days. Bloomberg News had been launched a few years prior, but it was more a print product, really more of a terminal product, but they were starting their TV operation. And I had already strung for them, worked as a cameraman as a freelance cameraman, so I had a couple of connections there, but they also had this funnel from NYU to Bloomberg for internships. And Russell, at the time, they were paying 20 bucks an hour, back in the 90s, and that was a pretty big deal, and we were interning like 30 hours a week. So, I had an NYU job, so I worked there and I was developing what would become Bloomberg TV, which was only on the terminals at that point, and they were trying to get some cable carriage. After NYU, I went and did some more documentary work, but then they eventually called me, Bloomberg, about a year, year and a half later, because they had a producer opening to cover the internet at the time and I remember creating a show called Web watch, watching these internet companies, AOL, Netscape and Pets, and whoever else was around in the 90s, Lycos, Yahoo, all of them. And so, I launched a couple of TV shows there as a producer, and that became my producing career, and then I had a really good career there. You go to work at Bloomberg, and you get a deep dive in not only business journalism, but business in general. They have this thing called Bloomberg University, where they just put you in the deep end, to learn everything you need to know and how to operate as a journalist with the right, not only the right what to look for, but how to cover things accurately, and how to do journalism for business, which is very special, and that was a huge, huge part of my career.

Russell Sherman

Man, I listen to you talk about that journey, and how you broke into the business, and I realized how fortunate I was. ran into an internship at New York 1 pretty much right out of college and was able to learn on the fly, and I think about the resourcefulness and the initiative that you showed becoming a stringer in New Mexico, then making your way to New York, taking a class in journalism, doing all these internships, breaking into it, and my guess is, by the time that you got settled in that seat, you had seen a lot and actually been really well positioned to succeed and the way that you did, because of what you had gone through, basically, literally, lifting yourself up from the bootstraps to make this work and actually break into the business.

Caleb Silver

I appreciate that, and I don't disagree at all. But if you think about the way that I kind of approach things, I was in the restaurant business for 12 years in Santa Fe, I started as a busboy when I was very young, then I became a waiter, then I became a manager, but by the time I became a manager, I knew and I was a cook, too, by the way in the kitchen, so I knew pretty much every job, so I could relate to people and what they were doing. So, when I was managing a restaurant, I knew what it took to do those other jobs successfully and the attitude. So, having been in those trenches that helped me there. And then when I went on to journalism and into Bloomberg, I started as a cameraman, then I became a producer, then I became a senior producer, and that's been the progression with you know, if you get in the trenches, and you understand what people go through and what it takes to do those jobs successfully, I think it makes you a better manager overall, but you got to start somewhere, and I was willing to do it, and I have zero regrets. Those are some of the funnest days of my life.

Russell Sherman

In 2005, you moved to CNN, and we have a mutual acquaintance who reported to you, her name is Janine Brady, she works for Schmidt futures, overseeing communications for Eric Schmidt's firm. And you talk about being a manager, she called you one of the best bosses she ever had. And in talking about you, obviously, it's her first job, she's so nervous coming into CNN, at the time working on the assignment desk, and she says you have this gift, you're so good at seeing what people are good at putting them in the right places to succeed. Does that come from just the many experiences that you've had, and as you said, struggling your way up to get to the place that you wanted to eventually be?

Caleb Silver

Well, Janine, I'm kvelling, as we say, that's such a sweet thing to say, and she was a rock star right out of the bat but you know, what tremendous attitude wanted to learn, wanted to do whatever it took to get into the mix. When you see that as a manager, you're like, let's go, let's find the thing that you want to do that we need. Let's find where those paths converge, and I think that speaks to, like I said, the experience of having done those jobs, all those jobs that get you on that staircase, on that ladder to where you want to go, ultimately, and knowing what people are going through and then appreciating that. So, the I've had a lot of success in my career, I'm really grateful for that but the most success I've had, the thing that I'm most proud of,I should say is people like Janine, and about 200 other people that I've worked with or for, or who have worked with me, mostly those that have worked for me or that I've had the privilege of supervising have gone on to do incredible things. So, when I hear things like that, I just feel so wealthy, but I think it is because I knew what those jobs took and I knew you had to be scrappy, and you had to want it, and the people that want it you can't teach that you can't teach the fire. You can teach the skills, not the fire – so people that have that fire, you just want to reward them. You have people like that on your team.

Russell Sherman

Yeah, I certainly do, absolutely, so fortunate. She says you taught her how to write as well and told her that she should pay attention to the Financial Times because the best lead sentences are in the Financial Times, which I wanted to hear your thoughts on that. I thought that was interesting.

Caleb Silver

I mean, absolutely. Not only that – the FT has some of the best obits as well. They're really good writers. Remember, back in the day, they didn't have bylines, so you didn't know who was actually writing them, but the lead sentences were so juicy, that you just knew the story. You could read the first two graphs and be like, I got this from here. And you know, Bloomberg, there are some good writers there too, but there was a way to write at Bloomberg that was very specific that they wanted, especially at that time, to repeat over and over again, and it kind of took the soul out of the story a little bit sometimes. And the FT didn't, the FT, even though they didn't have the byline, they were colorful, that great British wit about them, that twist of phrase as well, that just makes them so cool. They’re subscription only right now, so sometimes all you can read is the first two sentences or three sentences…

Russell Sherman

You get the lead regardless.

Caleb Silver?

Yeah, they're a victim of their own success.

Russell Sherman

Yeah, you also got to work at CNN with Wolf Blitzer. You were a producer on the Situation Room, that had to be a fascinating experience.

Caleb Silver

Oh, it was completely fascinating, and that was, talk about one of those lucky gifts you get by being in the right place at the right time. This was the launch of the Situation Room, probably 2007-8, whenever Katrina was, that we were launching around then. And the idea was, let's bring our viewers the news as we are getting it. In other words, we wanted the Situation Room to look and feel like a feed room where all the satellite feeds were coming in, and that's exactly what we did. We set up a huge wall behind Wolf of all the different feeds we're looking at. So, you'd see an empty podium, or you'd see a car chase, or you'd see a press conference or whatever was going on in the news you'd see across multiple screens. And we kind of tore up the rundown everyday, we had a very loose rundown. And I was fortunate enough to be a senior producer really working with Ali Velshi, one of the great journalists of our time, one of the great business journalists of our time now at MSNBC, covering everything. And we were sort of the business and economics team on that. But the idea was go into the show, know when you're supposed to hit in the rundown, and have an idea of what you were going to talk about, but let's not make the plan at nine o'clock in the morning for a four o'clock show. Let's look at what's going on, and then go for it, and have to react very quickly to the news. Well, unfortunately, but fortunately for the situation, rooms launch, Katrina was happening at that time, so the feeds were coming in from all over the place, and you were looking at this devastation and it was happening in real time. And we were looking at all this stuff going on, we were looking at oil tankers, or infrastructure being, you know, washed away and floated down the rivers or into the towns and we had to find out what that was, who owned that, make phone calls bring Ali in live, and that was the way the show was. Totally fascinating, super talented group of people, Wolf Blitzer is one of the legendary journalists of our time, broadcast journalists of our time, He's in my hall of fame, as nice a person as he seems, and great to work with. But that entire team was just a fast and agile and fun team to work with and we had a blast on that show for a few years.

Russell Sherman

I would think it was a real test of news judgment, learning what should go on, what's worth putting in and breaking into the rundown, as you said, what's not? What should we include? What shouldn't we include? Your skills around news judgment, I'm sure got honed pretty well, in that role.

Caleb Silver

Yeah, and especially in a devastating situation like Katrina, where like, people's lives are at stake, or people are losing their lives losing their homes – let's not jump to a conclusion. Let's figure out what's going on, and we often said, we're just watching this with you, Wolf, in real time, we're gonna get back to you when we know more details. And that was the way the show was, and that was the way it was supposed to be, and I think that's why it's still on the air to this day.

Russell Sherman

So about nine years at CNN. In 2016, you joined Investopedia – what attracted you to that platform?

Caleb Silver

Great question. Well, I'm a business journalist, so like a lot of business journalists or people in business, or in our world, and anywhere around the galaxy that you and I and our teams operate in, a lot of people use Investopedia. It's been around since 1999. You call it the Encyclopedia of finance and investing, and it is, it's got a massive encyclopedia, we have over 15-20,000 financial terms on the website, but it started in 1999. Four really smart guys in Edmonton, in Alberta, had this idea that they would put the dictionary for finance and investing on the internet, because there was all these .com companies popping and going public and this big rush of retail investors into the market. I'll get to why I joined in a second, but I want to give you a little background on it because it's fascinating. So, they started this thing and they also put test prep on there for the series exams – 63, 7 – so you could not only learn what the terms meant, but you could study for your exams, or your CFA exam, it was a very smart idea. And then they said, you know, there's this company in Mountain View, California called Google, and they're going to index the internet, or they're trying to index the internet. If we put all the definitions online and get other people to point to them, maybe they'll point to us and refer to us. Well, that was a pretty good idea too, because you wonder why we're often one of the top results on the term? We've been doing this for a very long time, we got a lot of backlinks, we have a history and people know the brand, especially in our world. So I knew it, because I used it in my various jobs, even at Bloomberg, even though I should never admit that, we all do – everybody uses it, and I've used it throughout my business journalism career. So, I was aware of this job that was opening up at IAC, at ?Investopedia, and I was like, well, I'm fascinated with Investopedia, I've used it for years, I'm as fascinated with IAC, which owns Investopedia, what's going on here? So, I reached out to some people I knew, and they said, No, this is real – IAC is into Investopedia and they're looking for a head of content or an editor in chief at the time. And I said, I definitely want to have a conversation with them, so I did. I had a couple of conversations with them and almost love at first sight, but I was like, Am I really going to… it's not exactly journalism, the way that I grew up with it, but this is a way of doing journalism, or educating people through this incredible platform, and the more I got to learn about it, and the more I learned about how they operate, how we operate now, and how IAC operates, the more I really wanted to be a part of it. So, that was six and a half, seven years ago, and it's been a great journey since then

Russell Sherman

It's known best, as you said, as a dictionary of financial terms that we, I think all sorts of people will go on, and look up the various words. There are certainly some obscure terms on there. Are you involved in the decision of when to add a new financial term to the lexicon? I’m kind of curious how you guys build that dictionary and think about it, and over time, refine it.

Caleb Silver

Yeah, so the dictionary is what we were built on – that is our foundation. That is why most people or how most people experienced this at first. But we've been adding a lot of things over the years: there's our whole retirement section, there's a whole section for financial advisors, there's a huge personal finance section, there's taxes, there's small business, so it's become a lot more than that, and news. We do a fair amount of news as well, but yeah, I'm highly involved in that. We've been around since 1999. A lot of these terms were written originally in 2001, 3, 4, 5, 8 10 – Investopedia, has gone through a lot of hands, and a lot of editors, and a lot of people have added to it. So, trying to, what I think I'm most involved with is the consistency and the updating of what we do, but especially in a, with the emergence of crypto and other asset classes, we've had to add a ton of terms every single day. I just added to term, requested a ter, the other day that we didn't have, based on Elon Musk abandoning his Twitter bid, the specific performance clause, we didn't have that. So I said, please, we need that term, this is going to become important in this lawsuit. So, I'm involved with that, but everybody's involved with that. Or we're also involved with somebody saying, hey, I read your term on alpha, and it's missing some key points, you should do this, and we will review it, we will run it passed our experts and we’lll add it. And that's what we do a lot of Russ, is updating terms because there are so many and occasionally new ones pop up, but it's the maintenance of those 15 or 20,000 or so that's so important because our world changes a lot and you want to make sure you have the most relevant information. Even though the definition of PE ratio remains the same, a case study can always be used, something more current to allow people to attach what's happening today to what that term means. I think you learn more, when you have that type of experience.

Russell Sherman?

Was it a specific termination clause? What was the…

Caleb Silver??

I think it was a specific performance clause. It's a legal term, but it applies to finance in this case, too, and the performance was really about his ability to raise the money and raise the debt to make the purchase.

Russell Sherman

Well, you point out that, and rightfully so, most people know it is a dictionary of terms, but it has become so much more. It's really, it’s basically a media site now — there's news, there's specific content to help people in different ways. You've played a large role in the six or so years that you've been there in really broadening the product set, the offering at Investopedia. What's your mindset in terms of really trying to make it all can be?

Caleb Silver

I've been a part of it, there's been a lot of people who have been a part of it too. Our GM Dylan Zurawell has been with us for 11 or 12 years, he has really helped craft this site as well. So, but for us, we know that the foundation will always be good and will always be strong and useful to people. I just used it in my podcast yesterday, I had to look something up, and I always refer to it, I let our listeners pick the term of the week. But, I think also that the nature of investing in the nature of finance and the nature of business and the nature of money is changing. It's always evolving, but it's really accelerated in the last few years. So it's not just crypto, it's defi it's what the future of NFT's are going to be, what the blockchain is going to do to investing, but also all these new asset classes that you have to think about as an investor. So what we try to do is always wear the hat of the educated investor, and how should the educated investor, especially in the 21st century, and 2022, 2023, think about things. Not what to buy, what to sell, when to buy, when to sell, but how to think about what's changing and what's happening in our world, and then be able to present content In a way that the modern investor and learner wants to learn it. People are always gonna want to read a definition, or watch one of our videos about our definitions – they're super useful – but there are other ways and they're more interactive. So our stock simulators a big way people learn, we explain what swing trade or options, how to buy options, so it's how to...

Russell Sherman

Stock market simulator, you have a space on the site where people can go in and basically make trades and do other actions that will simulate exactly what it is without any of the risk, obviously.

Caleb Silver

Yeah, and you wouldn't be surprised – it's one of our most popular parts of our site. People play games, there – free, no real money, but you play with fake money, but you learn how to do things so that when you are ready to actually trade or become an investor, you've got that foundation of learning, you haven't really burned yourself out of the game, if you lose money, you learn how it works, so I think that interactivity is super important. Obviously reaching our audiences where they are today is really important too. People Google us, we come up, and look up the definition or whatever they're looking up, or what's the difference between a Roth IRA and a Roth 401K, they're always looking for, because they have intention. So because our readers have intention, nobody's coming in browsing Investopedia for fun, including me, and I'm the editor in chief, they have an intention, what is it that they want? We want to have the best answers to their questions, but we also want to answer those questions in the ways they want to learn today. So that's interactivity, that's reading text if they want that's watching a video if they want it, and adding more tools to the site, so people can learn by doing. That's kind of where we are, and that's where we want to be in the next five to 10 years.

Russell Sherman

Mia Rossi, who produces this podcast, just hit me in the chat and said, she's all into the stock market simulator. So Caleb, if she leaves me and goes into a trading job somewhere, I'm going to hold you responsible.

Caleb Silver

It's all my fault, but then she has to take us all out to dinner.

Russell Sherman

That's right. Good point. I know you did a number of other things, that cross country bus tour at one point in terms of getting the name out there and doing other types of things, so you've really broaden the content in different ways in trying to figure out how to reach people almost as any way you can.

Caleb Silver

Yeah, we… I'm as promiscuous as you can get in our business, because I like to have fun. You know, if you're not having fun and mixing it up and getting people to pay attention and think about you in different ways, and you're kind of running in place and we don't want to do that. So yeah, we did a great tour. It was a financial fitness tour we did with American Century, few years back, where we went to four stops in the Midwest, we went to the Red Bull airplane show in Indianapolis, we went to the Quarter Horse Show in Columbus, Ohio, – we were all over the place – we went to a big football game at Indiana University versus Michigan. Wherever we could amass a lot of people we went with American Century around on a tour bus, I think that used to be used by Justin Bieber, at least that's what I was told and want to believe, and we went and did financial checkups with people and went and talked to people and had, did a quiz on their financial education, their knowledge, what they knew about their own financial situation, and then American century was able to bring their advisors and talk to people in person out on the streets and we filmed the whole thing, made a whole campaign, and it was cool, it was just so much fun to hit the road. You feel like sometimes, when especially you work in New York, or you're working in LA or San Francisco or London, and you're, you're not in touch necessarily with the real feel of the economy and how folks feel, even though we have visitors from all over the place, but it's so cool to get out there on the road and just talk to people and make a video dance about the whole thing.

Russell Sherman

You talked about American Century. How should companies and executives think about interacting with Investopedia in order to reach the audiences they care about? Because if you're a communications professional, you're a marketing professional, and you're looking at the Wall Street Journal or the FT, those are pretty well understood about how you can reach their audiences. You bring a little something different to the table.

Caleb Silver

Well, it’s that reader intent; they're not here by accident. They're not flipping through the Wall Street Journal or reading it on their tablet because that's part of their routine. They are at our site because they have a question, and we have an answer to that question, and we hope it's the best answer to that question, so having that intent is huge. And I liken it to this Russ: when I was at Bloomberg or when I was at CNN or you are New York 1, that was push. Extra, extra read all about it. Hey, check us out! Over here! We have the latest breaking news! Come and look! Investopedia, because people come to us through search and because we're intent based, is pull. We're not pushing it out at you. We're pulling you because you have a question. You have a query. And that's why our advertisers like to partner with us because it's not an accident that somebody is on our on our article “How do I start investing with $10,000?” They didn't wind up there by accident, I guarantee you that. And a lot of people come to that article every single month, in fact tens of thousands are coming to that because they have that question. Well, what does that tell you? That as a new investor looking to begin their journey, now which online broker or money management company wants to be in front of that? I can name about fifteen just sitting here right now. So, that’s the whole deal. We know what people want. We're not tracking them with cookies, and you can't do that anymore, we just know what they want and where they're coming from, because they're coming to us with the question. And that's why partnering with Investopedia works, and I'm not selling it, I've seen it in action, and it happens every single day, every single minute.

Russell Sherman

You mentioned paid…what about the opportunity for earned? The opportunity for companies, executives to present thoughts – whether it's thought leadership or market commentary – is that also something that you end up doing quite a bit of?

Caleb Silver

We do that in custom campaigns. The thing about that, my inbox every day, is about 50% people asking me to put their clients content on our site, or so and so wrote a great article or has this great quote on… would you add this to your so and so term? I understand that, I understand why they would want to do that, but I will tell you that for us to just take somebody's thought leadership and put it out on our site, it doesn't work. We are different. People come to us because they're looking for something not because your expert, or your chief economist is a genius and wrote something brilliant, and if you put it on Investopedia it's just like adding water, and it's gonna grow like wildfire. So, you have to think about it strategically. Now, the good news on that is we do partner with financial firms on thought leadership, and we do it together, because we happen to know what the audience wants, we happen to know where to put things and how to package things, and we'd like good thought leadership, and I use it on my podcast, we use it in articles, we'll do custom series on some pretty high level things – crypto in taxes – where we do want that thought leadership from an expert, and we're delighted to share brand space with them…and we'll get traffic for that as well, because people have questions about that. So when we think creatively about what's going to work, and what's the, it's not that you wrote great thought leadership, or your firm has it, and you put her with us and you're good. That's not strategic, strategic is: what are people looking for? Where's the pulse of the individual investor? What do they want right now? Let's create something together that we know they're gonna like, and they're, I think our readers are pretty smart, too, they don't care if there's somebody else's brand on it with us, I think that adds credibility. So, not just give it to us, but work with us on creating something.

Russell Sherman

Jointly, jointly curated content is really what's going to stand out and actually be more effective.

Caleb Silver

It's more interesting, too, by the way.

Russell Sherman

Any stats, you can throw me in terms of how many visitors you guys are getting, or?

Caleb Silver

Yeah, I think that's all publicly available, too, but we're, we get upwards of 14 million unique US visitors a month, we do about 20 to 22, 3 million depending on the season or so a year, got a pretty big global audience, mostly English speaking. So that's a lot, a lot of people coming to the site every single month, again, with intent. It fluctuates, it fluctuates with the market, like all of our businesses do. It fluctuates with the seasons, you know, when kids are going back into grad school or college and they're taking econ or they're taking a finance class, we'll see some spikes there and that's the cool thing about Investopedia is that we have so much content around everything about money that we can see the seasonality spikes, we know what's coming, we can anticipate it. We know the traffic pattern, we know where the surges are, we know where the lulls are and we know how to sort of like a farmer work the different parts of the field and the soil based on the season. And that's kind of a fun thing to do too, where that's not something you do in news as much yeah, you do, you have holidays, or things you can set the calendar by in news, especially in business news, but knowing seasonality based upon visitor intent and interest over 20 odd years? That’s pretty cool.

Russell Sherman

Where do you want to take it? Where do you see the platform in five years? More of the same…meaning building on what you've already created?

Caleb Silver

Yeah, I've been there six and a half, almost seven years and we've tried a bunch of different things, believe me, and like any firm knows, we still feel like even though we're a dinosaur on the internet, 23 years old, which is like 230 real years on the internet, we know what people love us for. So, we know we have to keep the foundation strong, but in terms of where we want to grow it, I think it's all about interactivity, it's all about tools. So, the stock simulator is a great tool, it's been around for like 11 years, but I'm thinking about personal finance, money, how to get your money right tools. Like, I want to simulate everything in my financial life. Me, as a consumer, as an individual who cares about money and is using it in different ways.

Russell Sherman?

Sure…has a budget and everything else.

Caleb Silver??

I want to do that. So, I, it's nice to have a mortgage tool, it's nice to have a retirement tool, it’s nice, but I want to put the whole thing together and you’ve seen, and you work with financial advisors and platforms like E money that do this, you can do it that way but I think bringing that to our audience, that's the future, I think for us. So, being really strong in education because we are not alone. Thebalance.com, which is also part of the dot-dash Meredith family, which we're a part of as well, they're great at this too, but there's not a lot of sites like us that are about education in finance and investing and that is what we do, that is our core. That keeps growing because our world in finance keeps growing. We want to grow with it, but I think that goes through down the interactivity stream in the future, for sure.

Russell Sherman

Congratulations on everything you've built there and excited to see what you guys continue to do. Should we finish off with some quick hits here? Some quick questions that we can ask you...

Caleb Silver?

Let's do it.

Russell Sherman?

This will be the Colgate University edition.

Caleb Silver

Yeah, this should be its own podcast, by the way, Russell.

Russell Sherman

This will mean something to like 5% of our listeners, but we love our 5% so. Alright, which bar is your favorite: the jug or the hourglass? There's only two really to choose from.

Caleb Silver

It was really The Bacon.

Russell Sherman?

Ah…

Caleb Silver?

Back Bacon.

Russell Sherman?

Haha, there you go.

Caleb Silver

I'm gonna go back bacon on your… bloodies at the back bake and maybe some darts. That was my spot. We loved hanging out there, but I would probably take the glass over the jug but you got to give the jug the love that it deserves. Had some unforgettable times there and I hope never to return.

Russell Sherman

Back Bacon, R.I.P. Pizza Pub or New York pizzeria – which one are you hitting?

Caleb Silver

New York pizzeria if you really want to get down with 100 wings delivered in a pizza box and taters that could kill a small family of alligators. Those things were heavy duty, definitely the pub, but you paid for it.

Russell Sherman

Alright. Did you have a favorite professor there?

Caleb Silver

I had so many good professors, but my advisor was Professor John Knecht in the art department, he was, I was an art an art history major.

Russell Sherman

Didn't you do film?

Caleb Silver

Yeah, I did video art actually.

Russell Sherman?

Yeah.

Caleb Silver?

With our friend Jim Sperber and Rob Bracci, and our good buddies back in the day, and I loved that department. I loved working with Knecht, he had a house orhe probably still does down the road, and he turned his chicken coop into a studio into a TV production video production studio. I always thought that was the coolest thing in the world.

Russell Sherman

Very cool. What was your special talent when you applied to school? Most people had a special talent to sort of help them stand out. Was there one that you think back to your application? Maybe just being from Santa Fe, New Mexico?

Caleb Silver

Yeah, well, I think that was the case, and I was a soccer recruit, believe it or not, so I didn't even know what Colgate was. I had maybe heard about in the back of my mind, but I had no idea of the prestige and legacy that it had. So, I think I hit it on the common app, but at the time, again, pre-internet Russ, so I maybe, I don't even know if I made a video of me playing goalkeeper in New Mexico where I was pretty good. I thought it was very good until I got to the northeast, but I think I sent clips to the coach, ?and he, I don't know how, maybe reached out to my coach, he recruited me and basically he said you don't have the boards or the grades, but if you agree to come here and play goalie, you got it. So commit to us, and we'd love to have you. Then I went and visited and for folks that have never been up there I was there and like on an October early October day pre snow, leaves were popping, kids were walking up and down the hill, gorgeous northeast, Central New York day, the Shenango Valley and I said this is the place. What do I have to do to be here? Coach said commit and you're in and I did and that's what brought me there. But I think if you want to know what I was remembered for, ask any of our friends, I brought some style to the place. I used to wear cowboy boots, and bright shirts and all my buddies were Fairfield or Jersey wearing hats on backwards and Oxford's untucked, And they thought I was nuts, and I thought they were nuts, so I think that's what I'm remembered for.

Russell Sherman

We needed some of your style. That was good. All right, favorite sport or sports team?

Caleb Silver

Well, I love golf. I love playing golf, it's probably my favorite sport. But I'm, you know, I was a soccer player and I was a lacrosse player too. My favorite team, unfortunately, sadly, is the Knicks. I'm just a belabored Knicks fan for so many years, but that's who I'll pull for, and that's who I'll ride for no matter what. Unfortunately, it is the New York Knickerbockers.

Russell Sherman

I know you like to golf, but longboarding is also something.

Caleb Silver

I like to roll, and I like to go sideways. I’ve been snowboarding since I was 14 in the early days when it was literally just the plank and two tire flaps. You put your Sorels under. I was an early snowboarder. I was an early skateboarder. I'm not a trick boarder, but I'm a longboarder. I like to carve and to take those long slopes, put a little Sublime on and just go and I do that. Luckily, I can do that a lot to work these days and on the way back, so I've been longboarding for a while and I love it. That's how I like to spend my free time. I spend a lot of time with my family, my wife, do a lot of good eating and cooking, and those are the things that bring me joy.

Russell Sherman

Are you doing the longboarding in the city?

Caleb Silver?

Oh, yeah.

Russell Sherman?

So you live in the city, right?

Caleb Silver

I live in Harlem and our offices are down in Battery Park City now. So, usually get out about 23rd Street off the or 34th Street on the A-train and get over to the West Side Highway and just bring it all the way downtown and that is a great way to start the day, I can tell you that.

Russell Sherman

How about favorite musician? Now I'm told, again from our mutual friend, that at 6AM hen you'd be on the assignment desk at CNN, you'd be blasting Jay-Z everywhere and waking everyone up with it, but give us your favorite musician.

Caleb Silver

Well, in the hip hop genre, Jay Z is the king for me. There is no one like him. He is one of one, but I'd say Bob Marley, that's my guy. I spent a lot of time in Jamaica as a teenager in the summers, got to know reggae music at a very young age and my favorite song, my favorite artists, the person I would love to spend some time with, if I could pick anybody in history, is Bob.

Russell Sherman

You love to cook. What's your go to? I'm told you're a black belt and guacamole.

Caleb Silver

I am like a triple black belt, I would say by now…Shaolin master. And that's because I worked in New Mexican restaurants growing up in Santa Fe. So I was making guac tableside, or I was prepping 12 buckets of guacamole for the day at Tomasita’s restaurant in Santa Fe, shout-out Tomasita’s. So, my guac will bring it to your knees, but I'm a really good New Mexican cook. That's a very special type of cuisine with red and green chili, but I do Italian, my breakfast will make you want to stay over, so I'm really good at all of that, and I love cooking and I love cooking for my kids. I got two teenage girls and watching them enjoy my food is probably my favorite thing in the world.

Russell Sherman

What's the secret ingredient in the guacamole?

Caleb Silver

It's a lot of lime, but people mess around with things like peppers and onions, and I don't want any part of that, or your mango, your pineapple, you take that and you can get out the back door. I keep it real simple: good jalapeno, good garlic, it's the avocado that's everything. But, plenty of lime, salt, but don't get too fancy, don't blend it into smithereens until it's a paste….little chunky. You know, it's the touch.

Russell Sherman

Favorite movie?

Caleb Silver??

Godfather. And it's going to be probably two over one, but the two of them together is an opera to me and one of the greatest pieces of art ever made.

Russell Sherman

Hard to argue with that. Although when I tell people it's Rocky, they ask me for the order of Rocky, so I understand why you're two over one.

Caleb Silver

You got gaps, I got gaps together, we fill gaps.

Russell Sherman

Right? You got to start with one obviously just out of a fairness, but it's probably what 1,3,4,2. Is there a dream job for you out there?

Caleb Silver

I kind of feel like I'm living the dream right now and I'm not just saying that to shine, but to be able to be myself and work for a company that I'm proud of what we do, reach the amount of people we reach, with really smart people where I'm, you know, I have a voice and a platform, that's pretty cool. And especially at 51 years of age Russ, I know, not everybody can say that, and I feel really lucky to be able to do that, but I love making documentaries and I love making movies, and I'm continuing to do that. So made a short film last summer in New Mexico. going to make another one this summer, did a lot of documentaries in my day. So, I'm trying to find this blend of kind of what I do using my platform, but also continue to make art through docs and through films and if I can blend that together and do some good cooking on the side, then that is the dream job for. It's not like I want to go do something else. I kind of found this path through all of these different streams, and I'm happy with where I've ended up. I see what I could do in the next five to ten years, like I just put it out there and I try to just build these little bridges to get to that. I think that's the dream.

Russell Sherman

We always ask people as a final question, to sum it up for us. What's the headline sort of on your career thus far? We all like writing and thinking of headlines, I'm kind of curious, what would be the headline on your career?

Caleb Silver

If you had to look backwards, and not to obit myself, Or to put it in the present tense. Caleb goes, he just goes, that's one thing that I do, I just keep going, good, bad, ugly. I just keep it going, and I try to keep my eyes on the prize. So maybe you could say he kept his eyes on the prize, and he kept going, he just never stopped, and that's kind of the way I want to approach things. My parents are that way too. They just keep going, and I want to be like that. And I think that brings good things because as I said, you stay in motion or you keep doing the same thing, you spin out after a while and I don't like that. I want to just keep dreaming and chasing things, and I still have that hunger and I hope I have it in 10, 20, 30, 40 years.

Russell Sherman

Keep going – that’s a good monitor for all of us. Don't stop, keep going. Perfect.

Caleb Silver

Can't stop won't stop.

Russell Sherman?

Can't stop won't stop. Caleb, thank you for letting us turn the tables here on Press Profiles. I knew it would be a fun conversation and it certainly was.

Caleb Silver

Thanks for having me. I'm honored to be with you.

Russell Sherman

That is Investopedia’s editor in chief Caleb silver; another fun conversation, and Caleb you actually I think are going to have the distinction of wrapping up season number one. You’re episode number 17, I think we're gonna give the staff of Press Profiles, the 200 person staff of Press Profiles, get the month of August off and then we'll kick it back into gear in September where we have lots of really additional good guests planned, so thank you for taking us out in style.

Caleb Silver

Thanks for letting me wrap up the season. I hope this means I get a Prosek vest or something, or a hat.

Russell Sherman

We are working on the merch, we got to come up with some good Press Profiles merch. Stay tuned. Keep an eye on your mail.

Caleb Silver

I will.

Russell Sherman

Remember, you can enjoy this and all the episodes of Press Profiles on pressprofilespodcast.com, or just head to Apple, Spotify, Google or any other podcast platform. Thanks for listening, and we will see you soon.