Prefer to read (or listen to) this newsletter in your browser? Click here.

💡 The Big Idea: How Sahil Bloom Created a New York Times Bestseller Using a Pocket Notebook

The author of an instant New York Times bestseller. A newsletter with more than 800,000 subscribers. A back-cover endorsement from the CEO of Apple.

These are pretty impressive accomplishments for any creator. And Sahil Bloom proves you can achieve these kinds of results without a complicated system.

He doesn’t have a vault of linked notes, a tagged read-later queue, or a meticulously processed daily review. His entire workflow fits in his back pocket: a single notebook, a single rule about what’s allowed to stay in it, and a small set of frameworks for what to do with whatever happens to earn its way out.

Every issue of his Curiosity Chronicle newsletter (and every framework he shares in his best-selling book The 5 Types of Wealth) started life on a page that could easily be lost in a coat pocket.

The interesting question isn’t whether his approach would scale to everyone (it wouldn’t). It’s what he’s doing differently underneath his intentional tool minimalism, and what overwhelmed PKM collectors might be able to learn from someone whose system is deliberately designed to prevent accumulation and clutter.

The Path From Private Equity to Best-Selling Author

Sahil spent seven years in private equity, eventually rising the ranks to become Vice President at a $3.5 billion fund. Before that, he was a Stanford baseball pitcher who double-majored in economics and sociology and stayed for a master’s in public policy. The plan, as he’s told the story on the Masters in Business podcast and elsewhere, was the standard finance track — Goldman or McKinsey, then business school, then find a fund. He was able to shortcut it by joining a PE spinout straight out of school as one of its first analysts.

So from the outside, everything was clicking. But on the inside, Sahil admits he was miserable. By his late twenties, his priority was set, and he was chasing a single goal: to make more money as the supposed gateway to a fulfilling life.

The pandemic (or as I like to call it, “The Big Reset”) gave him the margin he needed to begin writing on the side. He started posting long threads on Twitter that simplified finance (about Wall Street bets, options, bonds, etc.), and they started popping off. In the early days, he says he was spending four to eight hours on each thread, treating them as serious essays rather than throwaway content. As a result, his online audience grew quickly, and a newsletter followed.

Then, in May 2021, a conversation with an old friend reframed the whole thing. Sahil writes about it in a newsletter titled “It’s Later Than You Think”, and it has since become the pivotal opening story in the beginning of his book as well.

As they were sitting down for a drink, Sahil mentioned that living in California, so far from his aging parents in Boston, had been wearing on him. His friend asked how often he saw them and how old they were. Sahil said he saw them about once a year, and they were in their mid-sixties. The friend’s reply was simple math: you’re only going to see them fifteen more times in your life.

Forty-five days later, the house in California was listed. He left private equity the same year, and the side project became his main work. The 5 Types of Wealth later debuted as an instant New York Times, USA Today, and Sunday Times bestseller in 2025, and his newsletter now has over 800,000 readers.

That’s a pretty impressive pivot. But what he didn’t do to make any of that happen is the part that might surprise most PKM-practicing knowledge workers.

So in the rest of this post, I want to give you a brief breakdown of Sahil Bloom’s Creativity Flywheel.

Capture: One Notebook, One Rule

Sahil’s capture system is a dot grid Moleskine pocket notebook, paired with a Fisher Space Pen. He’s written on LinkedIn that he tried “every fancy note-taking strategy in the world” before settling on this. The pocket size is the point: it forces him to capture only high-impact ideas, because there isn’t room for the kind of arbitrary note-taking that dominated his school years.

The constraint that turns the notebook into a system, though, isn’t the size. It’s the rule he applies to what he captures there: anything he writes down has to create movement within 24 hours. Movement can mean teaching the idea to someone, reading more about it, executing the todo, or simply crossing it off as uninteresting. Whatever the action, the entry can’t sit there untouched.

This sounds almost trivially simple. But notice what it eliminates: the inbox. The most common failure mode in any PKM system is that captures arrive faster than they get processed, and the unprocessed pile becomes its own source of guilt and shame. Sahil’s rule has no inbox to fall behind on. The notebook clears continuously.

There is an obvious cost to this strategy. He does lose ideas that might have mattered later. But the benefit is that nothing accumulates dead weight. For someone whose primary output is short-form prose with a fast production cycle, that’s a calculated tradeoff.

What survives the 24-hour test, though, has to go somewhere. That’s where his second framework kicks in.

Curate: Sahil’s Five-Step Retention Framework

In a 2022 newsletter titled “How to Retain What You Learn,” Sahil laid out the framework he uses for material he actually wants to keep, not just react to. There are five steps:

1. Inspired Consumption — only consume what genuinely pulls you, and quit when the inspiration fades.
2. Unstructured Note-Taking — capture novel insights, key ideas, and anything that caused a reaction.
3. Consolidation — zoom out and group the unstructured notes around themes.
4. Analogize — place the new information into existing mental maps.
5. Idea Exercise — use spaced repetition so the learning doesn’t atrophy.

In Sahil’s system, the notes aren’t the destination. They’re simply a stage in a process whose endpoint is “this is now part of how I think.”

Most people stop at the note-taking stage and call themselves note-takers. But Sahil has a process that incorporates them into new mental models.

What’s striking for us nerds is that there’s no software in any of this. The “consolidation” step is described as re-consumption — going back through the unstructured notes to find themes — not as building a network of linked atomic notes inside Obsidian or some other personal knowledge management (PKM) app. The structure is flatter than what most knowledge workers would intentionally build, but that’s actually the brilliance of it.

It’s also more honest about what most of us actually do when we’re being careful: capture, review, group by theme, look for connections, and practice retrieval. The framework isn’t a rejection of digital PKM so much as a description of the cognitive moves underneath it, just with the fancy tooling stripped out.

The step where this framework really pays off, though, is step four: analogizing.

Connect: The Move That Turns Research Into Writing

Analogizing is doing far more work than its single-word label suggests. Sahil walks through it in the same “How to Retain What You Learn” essay using a real example from his own writing.

He had been researching Morris Chang and Taiwan Semiconductor Manufacturing Company for a piece. As he was consolidating his notes, he hit a moment where the new information needed somewhere to anchor in his existing mental map. Then the inspiration came: TSMC’s pure-play chip manufacturing model — building the foundry infrastructure that let independent chip designers start their own companies — was structurally identical to what Shopify had done for independent online sellers. They both built the platform, then let independent players build on top of it.

Once he had that analogy, the new information had a place to live. TSMC wasn’t just a Taiwanese foundry he had read about; it was the Shopify of semiconductors. That kind of compressed, surprising frame is what his threads and newsletters tend to be built around, and it’s where his writing finds its shape.

This is the move that allows him to turn all that research into a publishable piece. Most people stop one step earlier — they have themes, they have notes, but they haven’t put the new material in relation to what they already know. Without that, the writing just paraphrases the source. It’s bland. It’s boring. Anyone could have written it. But with this particular mental map, the writing becomes something only Sahil could have produced. By doing this, he’s made something that is distinctly his.

For PKM practitioners who rely on backlinks and graph views to surface connections, it’s worth noting that Sahil is doing the exact same thinking work (finding non-obvious links between ideas) without any of the infrastructure. The connections happen in his consolidation pass, in his head, against the mental map he’s been building for decades.

And once an idea has been analogized into a frame, it’s ready to grow.

Cultivate: Public Iteration as Development

The system question this raises is the obvious one: how does someone working from a pocket notebook produce a book that spent multiple weeks on the New York Times bestseller list?

The answer is that the book wasn’t written from the notebook. It was written after years of public iteration on top of it.

Sahil’s cultivation of his ideas happens out in the open. An idea earns its place in his keepable notes. The next test is social media, where he treats Twitter/X threads as serious essays rather than throwaway content. The thread is the first real-world test: does this framing land for someone who isn’t already in his head?

The threads that resonate become seeds for newsletter deep dives, but in a 2022 conversation with Nathan Barry, Sahil also described his weekend thread as the distilled version of a longer-form newsletter piece. The directionality runs both ways: a tested thread can become a newsletter, and a newsletter deep dive can be compressed back into a weekend thread. It’s part of a content flywheel that he uses to create consistently.

There’s a principle Sahil borrows from James Clear that frames this whole stage of his flywheel: everything you create is downstream from something you consume. He uses it explicitly in a 2023 Curiosity Chronicle issue on the four types of professional time, and I heard him share this idea live from the stage of Craft + Commerce in 2023. What I call cultivation in his content development model is the slow accumulation of inputs, framings, and feedback that an idea has to pass through before it can graduate to a published piece of work.

And consistently publishing those pieces of work is what gave him the foundation he needed to write his book.

Many of the frameworks in The 5 Types of Wealth (i.e., the Two Lists exercise, the Energy Calendar, the Life Razor, the 1-1-1 Method) appeared in the newsletter years before they became book chapters. The book wasn’t a leap from notebook to manuscript. It was the consolidation of three years of public research, thousands of interviews, and a much longer trail of ideas tested in front of a real audience.

There’s a small detail he dropped in his year-end 2025 newsletter that’s worth noticing: a few years before The 5 Types of Wealth came out, his book concept was actually rejected by an agent, causing him to pause the project. But he didn’t allow the rejection to kill the idea. It just moved it back into the cultivation phase via the newsletter for a while. The result is that the book that eventually got published was a more mature version of what would have come out earlier, because it had been through even more iterations in public before actually being printed.

For PKM creators, the lesson we can learn is that cultivation doesn’t have to happen privately. Test your ideas in public, and let the ideas that survive contact with the real world earn their way into the next stage.

Create: Constraints as a Writing Discipline

In a 2021 piece titled “The Power Business Writing Guide,” Sahil laid out four principles he applies to everything he publishes:

1. Draft Fast, Edit Slow — get the messy first version out without judgment, then edit in a separate cognitive mode.
2. KISS — keep it simple; most writing fails because the writer is hiding behind complexity.
3. Clear Target Reaction — define the “so what” before drafting. What should the reader feel, do, or take away?
4. Storytelling — lead with narrative. Humans are wired for it; lean into the wiring.

None of these are novel. What’s notable is how strictly Sahil applies these principles to his creative process. Tim Denning has observed that Sahil writes in short, punchy sentences, uses simple words even when fancier ones are available, leans heavily on bullet points, and looks at every line on a phone screen. And that’s because that’s where his readers will actually encounter it.

He’s clear, not clever. He writes to be useful to his readers, not to sound smart. And he does it consistently.

The regular output on top of this creative discipline is the part that should make us think. The Curiosity Chronicle now has over 800,000 subscribers. The 5 Types of Wealth hit the New York Times, USA Today, and Sunday Times bestseller lists at launch and was endorsed by Tim Cook, among many others.

And the “system” underneath all of it is: a pocket notebook, a 24-hour movement rule, a five-step retention framework, and four simple writing principles.

No vault. No graph view. No tag taxonomy. No daily review template.

That’s the part worth sitting with.

What I Take From Sahil’s Work

A lot of what we call PKM is a hedge against the future. We capture broadly because we don’t trust ourselves to know what will matter. We build elaborate systems because we don’t trust the simple ones to scale. We tag, link, and make atomic notes because we’re afraid we’ll lose what we once found.

Sahil’s workflow is the alternative theory. He trusts his own filter. He sets the threshold at “act within 24 hours or cross it out,” and he lives with whatever falls through. The ideas that survive his filter get analogized against a mental map he’s been building for decades. The ones that survive get written into the world.

I’m not going to suggest you throw out your vault. The Capture → Curate → Connect → Cultivate → Create flow he’s running is the same Creativity Flywheel I teach; he just runs it on paper and in his head, with a fierce constraint at the front end. For someone whose output is short-form and whose writing voice depends on synthesis and speed, his model is beautifully simple. And it proves a very important point:

The system should support the creator, not the other way around.

For the overwhelmed collectors out there — the people who’ve built vaults faster than they’ve built their ideas — the lesson isn’t to abandon the system. It’s to ask whether the system is actually metabolizing anything. Sahil’s pocket notebook isn’t impressive because it’s small. It’s impressive because nothing stays in it that doesn’t earn its way out. He’s eliminated the friction so that he can create consistently and effortlessly.

A vault that does the same thing is a useful vault. A vault that doesn’t is just a much heavier pocket notebook.

— Mike