How AI and Tools Are Transforming Journalism and Education | Jeremy Caplan | Glasp Talk #26
This is the twenty-sixth session of Glasp Talk!
Glasp Talk delves deep into intimate interviews with luminaries from various fields, unraveling their genuine emotions, experiences, and the stories behind them.
Today's guest is Jeremy Caplan, Director of Teaching and Learning at the Craig Newmark Graduate School of Journalism at CUNY and author of the "Wonder Tools" newsletter, where he shares practical tools for enhancing daily life and productivity. With a rich background in journalism, including work with Time Magazine, Yahoo! Internet Life Magazine, and Newsweek, Jeremy has vast experience at the intersection of journalism, technology, and education.
In this interview, Jeremy discusses how digital tools are transforming journalism and education. He delves into the concept of entrepreneurial journalism, where students learn to create micro-ventures like podcasts and newsletters. He also explores the rising role of AI in journalism, offering insights on how journalists can harness AI for creative and ethical purposes. Join us as Jeremy shares his thoughts on personal productivity tools, AI's impact on journalism, and his approach to inspiring the next generation of entrepreneurial journalists.
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Transcripts
Glasp: Hi everyone, welcome back to another episode of Glasp Talk. Today we are excited to have Jeremy Caplan with us. Jeremy is the Director of Teaching and Learning at CUNY’s Craig Newmark Graduate School of Journalism, where he plays a pivotal role in shaping the next generation of creative and entrepreneurial journalists. He’s also the author of Wonder Tools, a newsletter where he shares practical tools that help streamline daily life and maximize productivity. With a rich background in journalism, including writing for Time Magazine, Yahoo! Internet Life, and Newsweek, Jeremy is an expert in the intersection of journalism, technology, and education. So today, we dive into how tools are transforming journalism and education and explore some of Jeremy’s insights on teaching and learning in the modern era. So thank you for joining us today, Jeremy.
Jeremy: It’s a pleasure to be with you, thank you.
Glasp: So first of all, could you tell us, you know, what do you teach at your class, you know, for aspiring journalists at grad school?
Jeremy: The primary class I’m teaching at the moment is called Startup Sprint. It’s an entrepreneurial journalism class where we help people think through how to create something new that is a microventure in journalism—so a newsletter, a podcast, a niche site. And we help them think through what the product is, what the content is, what form and format it takes, what style and approach it takes, what purpose it serves, and what impact it can have.
From a product point of view, we help them think through how to build a community around that, or how to engage an existing community, how to grow an audience for that. And then the third part of it is the sustainability piece: how do you actually generate some revenue and manage costs and make it sustainable from a business or financial perspective so that it’s an entrepreneurial venture that’s sustainable and viable, and also impactful and meaningful. So that’s a class that gives people exposure to the world of journalism as it is today, as opposed to as it was a generation ago or sometime in the past.
And the idea is both to train people with entrepreneurial skills but also to help them develop a kind of open mindset, a creative and curious mindset, to encourage them to feel empowered to create their own new things. We don’t just have to work for other people in the journalism realm; we can also create our own new niche journalism ventures, which historically we could never really do as individual journalists. We didn’t have the power of the press in our pockets, we didn’t have access to the capital we needed to reach the masses, we didn’t have broadcast studios to produce expensive multimedia to distribute around the world through existing radio networks or TV platforms. But now we can reach people around the world with the devices in our pockets or with our laptops at very little, if any, cost. So we have tremendous power and potential, and we have to figure out how to harness that and make effective use of it for the benefit of the communities that we’re serving.
And so, that’s the class that focuses on that. I’m also developing a new class on AI for journalism, and how journalists can capitalize on AI, how journalists can make use of AI effectively, creatively, and ethically, and how AI is impacting the world of journalism as well. So those are a couple of classes. And then I teach occasional workshops on other related topics around digital journalism and how journalists can work effectively.
Glasp: Yeah, that’s really exciting, and also AI in journalism is a really interesting topic. But before diving into it, I’m curious, do students usually join your class with an idea or without having an idea?
Jeremy: Both. There are students who come in without any idea but sort of a curiosity or question. There are people that already have a community that they’ve been serving, but they want to serve the community in a different way, or they want to restart, or they want to improve what they’re doing. So there are people in both of those buckets.
Glasp: I see, I see. And then what is the first thing that you teach to students? Is that a mindset, or a big picture about what’s happening now? Or is it like a micro view?
Jeremy: First comes inspiration. So before you can do something new, you have to have the inspiration and the motivation to do that. You have to see that other people have done it and can do it, to know that you can do it yourself. So we first start with inspiration—showing people examples of creative entrepreneurial journalists from around the world, including some of our former students and participants in our program, who are people just like the people sitting in the seats of those students. So they know it’s not just someone very different in some other context but someone just like them, so they can do it as well.
Also, helping inspire them from their own capabilities and their own potential. So a lot of times, we think about entrepreneurship as coming from an external focus, meaning we look at a problem, we look at the needs of a community, we look at something in the world that’s broken and needs to be fixed—and that’s certainly a valuable lens through which to see entrepreneurship. However, it’s not the only lens. Another lens is to look inward at our capabilities.
There’s a model called effectual entrepreneurship where the idea is to look inward and think about what are the capabilities that you have that put you in a unique position to create something impactful. And specifically, I think of it as a SKIN framework—S-K-I-N—meaning your Skills, Knowledge, Interests, and Network. And that helps students look at these questions: what are your skills, what is the knowledge you have, what are your passions, and what is your network?
Jeremy: So invariably, people have more skills, more knowledge, and more interests and passions than they realize on the surface. We need to dive deeper into our own capabilities to source that inspiration and motivation that will lead to momentum. And so, in the SKIN framework, the last part is "N" for Network. So in addition to your own skills, your own knowledge, and your own passions or interests, you also have a network of people that you're connected to from your life experience.
However old you are, you've been part of different clubs, organizations, schools, jobs, and personal networks—social networks, family networks, religious networks—all kinds of networks of people that we've interacted with. Certainly, online networks of various kinds. So we all have bigger networks in many cases than we realize as well, with different levels of contacts. Some are very superficial contacts, some are deeper. But assessing that network that we all have provides another valuable insight into some of the capabilities that we're going to be able to benefit from by virtue of being connected to people who can help us in various ways.
As entrepreneurs, we can't do everything ourselves. In fact, there's a limited amount we can do with just our, you know, 168 hours in the week. And so, we need teammates, we need partners, but we also need supporters in our network who can help introduce us to someone or mention our podcast or our newsletter or our website in their newsletter or podcast or invite us to appear on their show, or attend their event, or give us guidance or insight. So when we look at these four things inward, we see we have skills, we have knowledge, we have interests, and we have a network that can empower us to then address a question serve a community, or address a moment that provides a catalyst for this particular venture. So that's what we start with, that's how we start the process.
Glasp: Yeah, that's amazing! And in terms of "N" for Network, do you have an alumni network? You know, because some students come to your class and graduate, and start their own things, but in terms of network, do you have an alumni network so that people can support each other? Also, I’m interested in the career paths of students who graduate from your class—what happens after they graduate?
Jeremy: We do have an alumni network. We have hundreds of people who have been through one or another version of our entrepreneurial program. We started the entrepreneurial journalism program in 2010 here at CUNY, at the City University of New York, the Graduate School of Journalism. We had a number of cohorts in person who came for six months—essentially one semester. And then, since 2020, we’ve been running online cohorts, and those are 100-day entrepreneurial boot camps, you might call them, where people develop their venture.
And there are a lot of people now who have been through one or another iteration of those programs, and they do serve as a network for one another. In fact, many of them stay in touch collaborate, and find ways of supporting one another. They’re on WhatsApp groups together, each cohort, and they’re also in touch with each other to support each other as accountability buddies, collaborators, and cheerleaders for one another. And I hope that continues to be the case because people working in entrepreneurship, as you all know, and anyone who works in an entrepreneurial capacity knows, oftentimes you're doing isolated work at your own kitchen table or in front of your computer by yourself. So it’s helpful to know there’s a network of people who you have something in common with, some shared experience or background.
In terms of what people do after, there’s a variety of different paths. Some work for traditional news organizations and try to work in a kind of entrepreneurial capacity. For example, we’ve had people work at the Yomiuri Shimbun and the Asahi Shimbun, for example, and NHK in Japan, and they work in innovative or entrepreneurship roles in those organizations. In other cases, people work for new kinds of journalism organizations, like the new ones that have taken shape in recent years. These are places like BuzzFeed, Axios, The 19th, Punchbowl, Capital B, and any number of organizations that are doing new kinds of journalism or doing journalism in new ways.
Then, a third group runs their own ventures, and these are people who have founded projects like Skillcrush, Narratively, How India Lives, DataLEADS, and many others around the world that are creating new kinds of journalism, serving new kinds of audiences, and filling in gaps in the news and information ecosystem. Then there are people in the fourth category who are doing all kinds of different things—maybe working for a nonprofit, taking care of family, or doing something else.
Glasp: Thank you, yeah. After hearing the introduction of the class, I’m glad I’m thinking, like, now I want to take your class! I hope it’s online sometime in the future.
So before teaching at the university, you started your career as a writer, right? You worked as a reporter at Newsweek. What made you think, “I want to become a writer or journalist” at that point?
Jeremy: Well, the first thing I would say is that I’ve always been a curious person. I always have a lot of questions. If I go on a tour, I’m always the person who has more questions left at the end and wants to keep the guide afterward to ask them more questions. I’ve always liked reading about things and learning about things, and I think journalism attracted me because it’s a field where you get to ask a lot of questions. You have to ask a lot of questions, and you have to learn a lot of things. You keep asking questions and try to understand things so you can explain them to other people, and help other people understand them.
I’ve also always been someone who had some skepticism about doctrines that didn’t seem to have a basis in thoughtful rationale. In other words, rules for rules' sake or things that were done because they’ve always been done that way. I’ve always wanted to challenge things that seem to harm people or leave people out, or didn’t optimize the experience people had in various contexts—whether that’s in an educational context, a hospital context, a legal context, or whatever.
I think that’s also a characteristic of people who are interested in journalism—many journalists want to understand why things are, and maybe challenge things that are abuses of power. They want to hold people with power accountable, or at least question the practices of power. That could be political power, corporate power, technological power, or any kind of authority or bureaucracy. So I’ve had a natural skepticism and curiosity about these things.
The third reason is that I like to write. I’ve never been particularly artistic from a drawing point of view, but I’ve always been interested in creative expression in other ways. In fact, before I was a journalist, I was a violinist, and I’ve always loved the violin. I’ve played since I was young, and I was inspired by the Suzuki method, the Japanese Suzuki method of violin training. In fact, as a child, I had a chance to meet Mr. Suzuki himself.
But I’ve always thought there’s something about journalism that allows for creative expression. We shape a story, an article, a piece of video, an audio, or whatever. There’s an art to it, a craft. It’s not pure information—it’s information shaped, curated, sensitively managed, and communicated. There’s an art and craft to that, and it involves words, which I love. I love reading, so all of those things combined—curiosity, skepticism, creative expression, and interest in words—are what shaped my interest in journalism.
Lastly, I’ve been indecisive at times, and I get bored easily. So I didn’t want to commit to one thing. Journalism allows you to do something new every week or month—you get to meet amazing people in different fields, and the technology keeps changing. So for all those reasons, journalism was very appealing to me and has remained so ever since. I’m proud to teach others about it now.
Glasp: That’s amazing. You’ve also written for Time Magazine and Newsweek, and you started your own newsletter, Wonder Tools. I’m curious, what motivated you to start writing a newsletter on Substack?
Jeremy: In April of 2020, we had just seen the beginning of the pandemic. I was sick, lonely, and anxious about the world and the pandemic. I wanted to be putting some positive energy out into the world because I saw many others who were lonely, sick, and anxious too. I felt like I couldn’t help on the medical or scientific front, but I could help in a tiny way by sharing tools that I found useful.
At that time, many of my colleagues were thrust into remote teaching and online work, and I had experience with online tools. So, I started sharing what had worked for me in the hope that it would help others.
Jeremy: There’s another piece of motivation, which was that I had been teaching entrepreneurial journalism for quite some time, and I always had this little itch at the back of my mind that said, "Why don’t you have your own entrepreneurial venture?" The truth was I’d helped a lot of students and worked with them, and I saw their ventures as my own in a way, even if I didn’t have a direct role. I felt proud that they were creating things and saw myself as having an indirect role.
But that left me with the itch: "Why haven’t I created my own thing?" Because I do believe you learn best by doing—not just by listening, thinking, or helping others do it, but by doing it yourself. So, I felt like I needed to do that so I would really learn. Also, the era had changed—the Creator Era was emerging. I needed to understand how this worked, not just from a theoretical point of view but from a practical point of view. If you're creating a newsletter, what are the practical, daily, weekly, and monthly things you need to do to make it succeed? I needed to have that lived experience.
So, those were the major reasons why I started it. And I also saw this moment of explosive creativity in the tech world. We were on the cusp of the AI era, the social era was moving into a new chapter, and new hardware was coming out. There was a lot going on in tech that I felt was under-covered. There was room for new guidance from an independent voice who could explain, simplify, and provide practical service journalism. That was the opportunity I saw, and that’s why I dived into it.
Glasp: I see, that’s amazing. I’ve been following and subscribed to your newsletter, Wonder Tools, and I appreciate you sharing those insightful tools and productivity tips.
I always wonder, you cover a lot of tools and share the pros, cons, pricing, etc. How do you keep your bias low? People have preferences, right? For instance, someone might love one tool, but you might prefer its competitor. Do you have a method for handling that, or do you embrace some level of bias?
Jeremy: Yeah, it’s a great question. I think we all definitely have bias in a lot of different ways. I use a Mac every day; I don’t use a Windows machine every day, so that affects my perspective on Mac versus Windows. When I can, I try to use multiple tools in a category, like with transcription tools—I use a whole range of them to stay open to different options and avoid assuming that one is always the best.
But I can’t do that for every category or hardware type. So I pick certain things, like the Mac platform, but I try to educate myself beyond Apple, iOS, and Mac. The reality is that my content often leans more toward Apple, iOS, and web platforms.
People who read closely might notice I don’t cover Android as much as iOS. That’s just a path I’ve chosen because of my limited bandwidth as a solopreneur doing everything—product, growth, sustainability, and operations. In terms of other biases, I try to work with students and people at different levels as a coach and observer. I see how my parents use tech, how my daughters use it, how my friends use it. So I try to keep multiple perspectives in mind—different levels, interests, and goals.
When I write, I aim to be as objective as possible, backing it up with examples so people can decide for themselves. I show what I use a tool for, why I think it’s useful, its limitations, and alternatives. Hopefully, people can decide whether they want to try it or explore something else.
Glasp: Thank you for sharing. With all your knowledge of productivity tools, have you ever thought of making your own productivity tool? And are there any hot topics or trends in the productivity tool space that you’re particularly interested in right now? Maybe AI or something else?
Jeremy: If I could live 50 lives, one of them would definitely involve creating a lot of products. I love thinking about product interfaces. I have a lot of conversations with product creators and entrepreneurs about what’s working, what’s not, and how products can be better. I think of product design as an art and a craft—balancing new features, simplicity, and utility is a fascinating challenge.
But my training is not in the technical skills of product creation. So given the limited number of hours we have in a week, I’ve chosen to focus on other priorities like journalism, writing, teaching, and spending time with my family. That’s where my energy goes right now.
In terms of trends, one area I’m particularly excited about is the next generation of note-taking tools. Personal knowledge management (PKM) is so central to productivity. It’s not a new concept for people in the space, but there’s been a lot of progress recently, especially with the help of AI.
There’s still no perfect tool that works for everyone, but we’re getting closer to tools that address the challenges of traditional note-taking systems. These new tools, like Obsidian, Capacities, Tana, Anytype, and others, are starting to show what it might look like if we didn’t have to organize everything manually—if the system could do it for us, allowing us to focus on creativity and reflection.
The idea of a universal personal knowledge hub, rather than having 20 different repositories for bits and pieces of our work, is really powerful. I think we’ll see a lot of progress in this space over the next few years, especially with the integration of AI.
Glasp: Is it the same for journalism? How do you think AI will impact journalism? How people write or consume media?
Jeremy: Journalists, like people in many fields, rely on research, gathering information, sifting through it, identifying what’s important, organizing it, and then transforming it into stories. AI can help tremendously in this process—organizing notes, sifting through information, and identifying important insights.
Journalists will need tools to sort through the massive volume of information being produced. By 2025, estimates suggest the majority of content online will be AI-generated, so there’ll be a lot of noise and low-quality content. Journalists will need tools to make sense of all that, to curate and synthesize it, and to act on it.
In terms of multimedia, AI is already helping with menial tasks like cleaning up audio, removing background noise, filtering out filler words, adjusting color balance, etc. These are small but time-consuming tasks that AI can handle, freeing up journalists to focus on storytelling. For instance, tools like Descript are great for editing audio and video with AI.
Glasp: Totally agree! Sorry, time is running out. We have two more questions. What advice would you give to aspiring writers, journalists, and entrepreneurs?
Jeremy: Establish rituals and habits. What we do daily or consistently is what makes us who we are and defines the quality and impact of our work. It’s much better to aim low and start small, doing something consistently—like writing for five minutes a day—than to aim high and do something sporadically. Progress happens through small, consistent steps.
It’s also important to seek inspiration in the world around you. Find sources of joy and creative stimulation wherever you can—in nature, museums, conversations with people. There’s so much around us that can inspire us, and if we approach the world with a mindset of possibility, we’re more likely to discover new ideas.
Glasp: That’s really inspiring advice. Thank you for sharing! And lastly, since Glasp is a platform where people share what they’re reading and learning as their digital legacy, we want to ask you: What legacy or impact do you want to leave behind?
Jeremy: I think the legacy we leave behind is the impact we have on the people we’ve encountered throughout our lives. We share a little bit of ourselves with the people we meet, and hopefully, in some small way, I’ve left a positive impact on some of the people I’ve encountered. Whether it’s helping someone feel more confident, learn something new, or do something they couldn’t do before, I hope I’ve made a small difference.
Through writing, teaching, and the connections we make, we pass on what we’ve learned from others. That’s what I hope to leave behind—a legacy of sharing knowledge and helping others grow.
Glasp: That’s beautiful. Thank you so much, Jeremy, for taking the time today. We really enjoyed the conversation and learned so much from your experience.
Jeremy: Thank you. I appreciate the opportunity to chat and reflect on these things. Thanks for the thoughtful questions and for sharing this time with me.
