The Backstory
From Jerusalem to Substack
The image of Jeremy Caplan at Princeton is a specific one: a young man who is simultaneously the concertmaster of an international symphony orchestra in Jerusalem and a public policy student in New Jersey. At some point, you have to choose a lane. He chose journalism.
That choice led him to Columbia's J-School as a Knight-Bagehot Fellow, then to Columbia Business School as a Wiegers Fellow, then to The Paris Review, Yahoo! Internet Life, Newsweek, and eventually Time Magazine - where he spent years reporting on the companies that were reshaping how people worked, played, and understood themselves.
The Time years were formative in a particular way. Caplan wrote about Google and Apple and Yahoo when they were still ascendant, still genuinely exciting, still capable of surprise. He also covered what he calls cultural micro-trends: carrotmobs, where consumers would reward environmentally responsible businesses with mass patronage; cereal cafes, which were exactly what they sound like; life-hacking, before that term became exhausted. He had a talent for finding the small, strange thing that revealed something true about the larger moment.
The Pandemic Pivot
In April 2020, with the world suddenly forced into remote work and everyone scrambling to figure out which apps could replace which physical offices, Caplan did something that looked modest at the time: he launched a newsletter.
Wonder Tools was not a pivot. It was an extension of everything he had already been doing - testing digital tools, teaching journalists to build independent businesses, thinking seriously about what technology actually helps people versus what merely exists. The pandemic just clarified the audience: suddenly millions of people needed guidance on tools they had never heard of, and they needed it from someone who would be honest about what worked.
Five years later, that newsletter has 85,000+ subscribers in 201 countries. It is syndicated through Fast Company. It has spawned a podcast with 75+ episodes and a YouTube channel with hands-on tutorials. And it is still, after all of it, written by one person who personally tests everything he covers and personally reads the emails he receives.
The CUNY Mission
The newsletter is the public face, but Caplan's day job is substantive in its own right. As Director of Teaching and Learning at CUNY's Craig Newmark Graduate School of Journalism, he runs the Entrepreneurial Journalism Creators Program - a 100-day curriculum designed for independent journalists worldwide who are building newsletters, podcasts, and niche news operations.
He helped direct the first global M.A. and certificate programs in Entrepreneurial Journalism, programs that have supported hundreds of journalists over more than a decade. The work is unglamorous in the best sense - practical, concrete, focused on helping working journalists build things that sustain themselves financially without compromising editorially.
There is an obvious connection between the newsletter and the teaching. Wonder Tools is itself a proof of concept for the kind of independent journalism Caplan spends his days teaching others to build. He has done it. He knows what it costs in time and attention and money. He also knows it works.
The Philosophy
On AI, Caplan is careful in the way that a person who has thought seriously about it tends to be careful. He describes AI tools as "probabilistic tools" - things that are useful but prone to errors requiring human validation. He argues that "there should always be a human in the loop." He uses Claude, NotebookLM, ChatGPT, and Perplexity regularly, and has been explicit about testing all of them in real workflows before recommending any.
He is also clear-eyed about AI's effect on writing quality. "Everything can summarize everything these days," he has observed, "but they do at different levels of quality." That distinction - between tools that merely produce output and tools that produce genuinely useful output - is what Wonder Tools is built to surface.
The newsletter's growth strategy reflects the same practical orientation. Social media is not a primary driver; he considers Twitter/X less effective than it once was. Most new readers come from recommendations by other Substack creators - those 277 newsletters that point their audiences toward Wonder Tools. That kind of growth is slow. It is also durable.
At the heart of it is a conviction that most people do not have enough time, and that the right tools, honestly evaluated, can give some of it back. That is not a revolutionary idea. But executed with the consistency and rigor that Caplan brings to it, week after week, for five-plus years, it turns out to be rare enough to build something significant around.
