Dawn Wotapka’s Media Movers: Investopedia’s Caleb Silver

One of journalism’s golden rules is to write simply, which can be tricky when trying to boil down complicated financial terms. Numerous times over the years, I’ve relied on Investopedia to help me understand everything from short selling to credit default swaps.

Since its founding in the late 1990s, Investopedia has in fact helped millions worldwide grasp the ins and outs of how money works. Its users range from media pros to everyday people looking to buy a new car — and our own TBN editor and publisher, Lou Carlozo: “I lost count a long time ago of how many times Investopedia has saved me on deadline.”

At the helm of this vital service site is Caleb Silver, a longtime journalist whose impressive resume includes Bloomberg and CNN. His mission is to make sure that visitors get clean, comprehensive answers to their questions.

I chatted with Caleb about his background in documentaries, growing up in business news, commuting on his longboard and being an “explainer in chief” — a phrase I fell in love with.

Dawn Wotapka: Tell me about your role at Investopedia. Who are your readers?

Caleb Silver: I’ve been the editor-in-chief of Investopedia for seven years, but I’ve been a user of the site since it launched in 1999. We have more than 13 million monthly readers who come to us in search of answers about money writ large, but also investing, saving, trading, budgeting, running a small business, and taxes.

Dawn: That must make for a broad swath of users.

Caleb: Our readers come from all over the world with very specific questions. Our job as editors is to make sure we have the best and most comprehensive answers. We have more than 30,000 articles, terms, explainers and FAQs on our site, and our editorial team spends a lot of time updating those to make sure we have the most clear and current information available. As the editor-in-chief, I’m responsible for our voice, our range of coverage, and all the new things we’re doing at Investopedia to engage our audience. I host two podcasts, “The Investopedia Express” and “The Green Investor.” I work with our data and research team on reader surveys and economic indicators, and I appear across cable, streaming, radio and digital financial media as our “Explainer in Chief.” I am also helping lead our financial literacy efforts in communities that don’t have easy access to it, and public schools around the country.

Dawn: How do you define success in your current position?

Caleb:  We’re always asking ourselves if we have the best answer to our users’ questions about money and investing. We can gauge that by looking at traffic and ranking of our articles. But for us, it’s more about really answering the intent of the questions. Are we helping educate people well enough that they can then make smarter financial decisions? If so, all the metrics should point to success. But we’re also fortunate enough to get a lot of feedback from users who tell us that we’ve helped them, and also provide recommendations about what else they’d like to see from us. We listen very carefully to that, and it makes us better. That’s the definition of success—a continuous process of refinement that improves our readers’ relationship with money.

Dawn: How does Investopedia define itself? Is it journalism? Or something else?

Caleb:  Investopedia is a fascinating hybrid of journalism and education. We produce hundreds of news stories every month, but we also continually update our existing library of educational content with relevant news that helps bring context to financial concepts.

I grew up in business news at Bloomberg and CNN, where we pushed content out to our users, but Investopedia is a very different type of media platform. Since most of our readers come to us via search, we know they have questions about the topics they’re reading. It’s our job to provide the best answers that contextualize what they are searching for.

Dawn: You started your career producing documentaries. Do those skills benefit you today?

Caleb: I’m a storyteller at heart. That’s how I define myself today, and when I began my career producing documentaries. Money and finance are full of incredible stories and I try to incorporate some form of storytelling in my columns, podcasts, and media interviews. It’s a powerful tool for educational content and when you can explain how something works through storytelling, you give readers the context to truly understand how those topics affect them and the world around them.

Dawn: I noticed that you received several promotions at CNN. What do you think helped you advance in what I would imagine is such a competitive place?

Caleb: I always try to be solution-oriented while seeing the broader path in front of me. I also sought mentors and managers whom I admired and wanted to model my career trajectories after. I made sure my managers knew I could be a solution to a problem or an opportunity we were facing, and had a plan ready for the day I was given the opportunity. I also benefited from timing. When the financial crisis hit in 2007, I was running the assignment desk at CNN in New York, but given my experience at Bloomberg, I was in a unique position to help lead the network’s financial coverage. I was eventually promoted to be the Executive Producer of CNNMoney, and then the Director of Business News at CNN.

Dawn: Tell me about your mentors.

Caleb: Georgia Maryol was my first real boss when I was just 16, working in the kitchen at Tomasita’s restaurant, one of Santa Fe’s most popular dining establishments. She owned several restaurants and properties, but she was the first person to fix a drain or clean a spill in the kitchen — and then go greet guests in the dining room and make sure her customers were happy. I learned from Georgia that you have to be willing to roll up your sleeves as a leader, but also show grace and gratitude to those you serve. In business news, Myron Kandel is my mentor and hero. He helped bring business news to cable television when CNN launched in 1980 and has mentored hundreds of business journalists over his legendary career.

Dawn: I stumbled across a few videos of you skateboarding. How did you get into this and how often do you get out on a board?

Caleb: I’ve been riding sideways since I was 11 as a snowboarder and skateboarder in Santa Fe. I’m a little too old to get tricky these days, but I cruise on my longboard almost every day as part of my commute. I’m usually listening to music when I do, so I started making little posts on my skating journeys with the songs I am listening to so I can share the vibe. My teenage daughters like them on social media, so I’ll keep rolling until they don’t.

Dawn: I’m a former board member of SABEW (the Society for Advancing Business Editing and Writing), and I know that active with the organization. So few younger journalists are involved with professional organizations. Why is that?

Caleb: I had the honor of serving as President of SABEW last year and I’ve been a board member for the past seven. It’s been one of the most fulfilling experiences of my professional life. Organizations like ours need to do more to make the case for younger journalists to join, and that comes with stronger engagement, career advancement, mentoring opportunities and skills training. SABEW has done a lot in those areas but it’s the responsibility of the board to make sure potential members know about it and clearly see the benefits of membership.

Dawn: What would you say to a young person interested in getting into journalism?

Caleb: The pathways into journalism have multiplied and morphed so much over the past 20 years, and the definition of the profession has changed with it. YouTube hosts have larger audiences than cable television, Substackers reach more people than established news brands and TikTok’ers are driving the kind of engagement that broadcasters dream about. As audiences migrate to their preferences, traditional journalism organizations are struggling to find and keep them.  But at its core, journalism is about the truth and great storytelling — and audiences absolutely still want that. If you care about the truth, if facts matter to you, and you have a desire to help others better understand the world around them, then there is no better profession than journalism.

Dawn Wotapka is a former Wall Street Journal reporter who lives in Atlanta with her husband and two children. She is a slow runner and an avid Peloton user. To submit tips for her Media Movers column, you can contact her at dwotapka@gmail.com. Be sure to connect with Dawn on LinkedIn.