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Packy McCormick: A Tactical Masterclass in Online Writing
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Sign Up for "Writing Examples" and Learn From The Best Writing of All Time: https://www.writingexamples.com Packy McCormick is proof that writing online can attract real-world opportunities you never dreamed of. He went from 20 Substack subscribers to a $40 million venture fund — and he’s still growing. In this episode, we dive into the three main “how’s” of Packy’s growth. First, he has a distinct, unforgettable style. His business-meets-memes newsletter, Not Boring, has amassed 220,000+ subscribers because his “funny finance guy” flair gives him an edge. Not to mention, it all started when he took the first-ever cohort of Write of Passage. (I may be biased, but seriously, that’s when it started.) Next, Packy shares his domain expertise. He sees writing and investing as the perfect one-two punch. His goal? Share what he knows, and make a behind-the-scenes world accessible to the average audience. And finally, Packy adds value to his readers. Relentlessly. Not by telling them what to think, but by trying to change the way they think. In a world filled with Beta content — cheap entertainment that disappears in 24 hours — Packy creates Alpha content — quality work that has long-term relevance. Style. Expertise. Value. This is just a sneak-peek into our conversation. If you want to find your distinctiveness in a modern digital world, this episode is for you. SPEAKER LINKS: Website: https://www.packym.com/ Twitter: https://twitter.com/packyM Newsletter: https://www.notboring.co/ WRITE OF PASSAGE: Want to learn more about the next class for Write of Passage? Click here: https://writeofpassage.com/ PODCAST LINKS: Website: https://writeofpassage.school/how-i-write/ Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470 Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv TIMESTAMPS: 00:00:00 Introduction 00:01:25 Writing titles and hooks 00:04:00 Writing introductions 00:06:30 Writing short vs long form 00:12:30 Cultivating your voice 00:19:15 Writing process 00:23:30 Writing on the weekends 00:28:00 Elon Musk 00:29:50 Flow 00:40:00 Writing with AI 00:44:30 Business model of writing 00:48:30 Writing and investing 00:53:25 Attracting audiences 00:57:15 Writing long form 00:59:30 Editing 01:02:50 Writing "The Great Online Game" 01:14:15 Where to find inspiration ABOUT THE HOST: I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible.
Segments Timeline
Crafting the Perfect Title
Packy McCormick shares his insights on creating compelling titles, thumbnails, and first sentences. He emphasizes the importance of making content accessible and engaging, aiming to write the best piece about a company that helps readers understand complex topics. This segment highlights the significance of humor and clarity in online writing.
"What makes for a good title, thumbnail, first sentence? Born to Tell Dad jokes. I'd like a good pun. The goal is I want this to be the best piece that's ever been written about this company. I w..."
The Messy Writing Process
Packy discusses his writing process, which involves a chaotic yet effective approach to crafting titles and images. He explains how he often starts with a title that inspires him and how the writing evolves, culminating in a last-minute check for visuals. This segment reveals the behind-the-scenes of his creative workflow.
"All right, Packy, this is going to be a trip down memory lane. We go way back to the days when you literally hadn't written anything and I was teaching Write of Passage in my bedroom. But one of..."
The Art of the Introduction
In this segment, Packy elaborates on the importance of a strong introduction in writing. He likens it to skiing, where plotting your line is crucial for momentum. He discusses how a well-crafted introduction sets the stage for the entire piece, guiding both the writer and the reader through the narrative.
"What makes for a good title, thumbnail, first sentence? I think what makes for a good title is... I mean, I was born to be a dad, and I was born to tell dad jokes. I like a good pun. I think if i..."
Alpha vs. Beta Content
Packy contrasts 'alpha' content, which aims to change readers' perspectives, with 'beta' content that lacks depth. He emphasizes the need for originality and thought-provoking ideas in writing, aiming to inspire readers to think differently about familiar topics. This segment underscores the value of meaningful content in a saturated digital landscape.
"going to follow it. We'll see if it's what the implications of it are, right or wrong. So what you're saying is that a good introduction, I was sort of applying that it's a hook. What you're say..."
Barbell Writing Strategy
Packy introduces the concept of barbell writing, advocating for a mix of short, impactful pieces and long, in-depth analyses. He discusses how this approach caters to different reader preferences and allows for a diverse range of content, enhancing engagement and understanding. This segment highlights the strategic thinking behind content creation.
"more optimistic about something, and you think it's a little bit more likely that a thing like this might happen. And so I'm more going for that than like, "Oh, man, this is the hook that somebo..."
The Goal of Deep Dives
In this segment, Packy reflects on his goal when writing deep dives about companies: to create the best piece ever written about them. He shares how he aims to make complex topics understandable, often receiving feedback that his writing helps others explain their work to family. This highlights his commitment to clarity and accessibility in writing.
"I mean, every time I write a piece on a company, the first time I thought about it this way, I was writing about companies in the beginning that were either public, and so I just wanted a differ..."
Setting the Scene Like a Comedian
Packy discusses the importance of quickly setting the scene in writing, drawing parallels to comedians who establish context efficiently. He admires the ability to create engaging narratives with minimal words, emphasizing the need for clarity and humor in introductions. This segment showcases the influence of storytelling techniques on effective writing.
"One of the things that I've taken from comedians is, and this comes back to introductions, is how good they are at setting the scene quickly. So someone might say, "I was on a bus and all of a s..."
Using Hyperlinks for Context
Packy explains how hyperlinks enhance online writing by providing context without lengthy explanations. He emphasizes the importance of treating readers as intelligent and curious, allowing them to explore ideas further. This segment highlights the strategic use of hyperlinks to engage and inform readers effectively.
"advantage that we have as online writers is the hyperlink, because what the hyperlink does is it allows us to embed context in a little blue text with a little underline, and we can say, "Romulus ..."
Cultivating a Unique Voice
Packy reflects on his journey to develop a distinct writing voice, influenced by his experiences in Write of Passage. He discusses the importance of finding a personal monopoly by blending humor, pop culture, and business insights. This segment illustrates the evolution of his style and the impact of consistent writing practice.
"voice? One of the things that's happened is I think you use less pop culture references than you used to. But when you started, you didn't have nearly the voice that you have now. And what's int..."
Navigating Expectations and Authenticity
In this segment, Packy addresses the tension between his authentic self and the caricature that emerges from public perception. He discusses the challenges of maintaining originality while meeting audience expectations, emphasizing the importance of staying true to oneself as a writer. This segment explores the complexities of identity in online writing.
"a caution that I need to figure out how to remove. Oh, I feel you, man. I mean, the way that I was thinking about what you just said is that when you first start, there's you. And it's timid you, ..."
The Writing Process: From Excitement to Drafts
In this segment, Packy outlines his writing process, which begins with capturing excitement for a topic. He discusses the importance of drafting without self-editing and the iterative nature of his writing, where he refines ideas through multiple drafts and research, often under tight deadlines.
"Totally. Yeah. I see that all the time when I try to overthink something or over intellectualize it or sound smarter than I am, it comes across as flat. If I'm like, "All right, I'm excited abou..."
The Pressure of Deadlines
Packy reveals how deadlines influence his writing, often leading to intense last-minute revisions. He describes the adrenaline rush of finalizing essays in the early morning hours before publication, reflecting on whether this pressure enhances or detracts from the quality of his work.
"through that process over and over and over again. And what the process actually looks like is, and what I've been doing recently is I open up a Google Doc, do the title, title image, start writi..."
Balancing Family Life and Writing
Packy discusses the challenges of balancing his writing career with family responsibilities. He shares how he has adapted his writing schedule to reduce stress and prioritize family time, illustrating the impact of personal life on his creative process.
"will be, it's not just completely fresh, and this is not for if I'm writing a deep dive on a company where I've spoken to the company a bunch, I've done a lot of research, I know the angle, thos..."
The Role of Curiosity in Writing
In this segment, Packy reflects on the importance of curiosity in his writing. He compares his approach to that of other writers, emphasizing his obsession with understanding topics deeply and how this drives his content creation, especially under time constraints.
"weekends and just batch... I started sending on Tuesday instead of Monday, so I at least have that day to run through some more drafts. But I've really pushed all that stress into the last four ..."
Making Business Writing Engaging
Packy shares his mission to make business writing more engaging and relatable. He discusses the perception of business topics as dry and uninteresting, and his goal to convey the excitement and drama behind business strategies to captivate his audience.
"else. And so that time crunch makes me feel like I lose a little bit of that superpower, right? This is my Packy riff on who you are. So it's like a bunch of friends, you're sitting around the ta..."
Elon Musk: The Memer and Entrepreneur
Packy discusses Elon Musk's unique blend of entrepreneurship and humor, highlighting how Musk's personality makes complex business concepts more accessible. He reflects on the importance of humor in engaging audiences and the value of unconventional thinkers in the business world.
"that people like Elon Musk so much, that Elon is a grade A entrepreneur, say engineer, and then also he's a memer, and he's funny. And because you get the laughs, then when he talks about, "Hey,..."
Finding Flow in Writing
Packy describes the experience of achieving flow while writing, where ideas come together seamlessly. He shares how this state of mind allows for unexpected insights and creativity, contrasting it with the challenges of overthinking and self-editing.
"no, you need that Elon crazy. And net-net, what a positive thing for the world that exists. You're talking about flow. What does that practically look like for you? Flow is getting five pages into..."
Voice Transcription: A New Writing Method
In this segment, Packy discusses his discovery of voice transcription as a writing tool. He explains how this method enhances his ability to write freely and creatively, allowing him to focus on generating ideas rather than the physical act of typing.
"One thing that I've noticed is, so I really struggle to get into flow when I'm typing. I don't know what it is, I feel like I probably have some early onset arthritis or something. It's just lik..."
Epiphanies and Structure in Writing
Packy explains how epiphanies manifest for him during walks, often starting with a single sentence that evolves into a structured piece. He shares a specific idea inspired by a conversation with Michael Mauboussin about informationally efficient markets, illustrating how he develops thoughts into coherent writing through verbal exploration.
"What do you have going into your walk? Do you have an idea for something and you just riff? Do you have a structure already? Yeah, so the way that an epiphany manifests itself for me is a full bo..."
The Art of Talking to Yourself
In this light-hearted segment, Packy discusses his unconventional method of talking to himself while walking to develop ideas. He humorously describes how he avoids looking crazy by pretending to record voice memos, showcasing the importance of self-dialogue in the creative process.
"once I hit the third time, I'll usually have the structure, take that, airdrop on the computer, type it up, and the piece will be done. And do you feel like a crazy person walking around? Yes. Ye..."
Researching and Writing with Purpose
Packy shares his experience of conducting in-depth research on Tencent during the early days of COVID. He describes the satisfaction of uncovering valuable information and creating a comprehensive document, emphasizing the joy of discovery and the importance of thorough research in writing.
"so I'm just going to get into the internet and go to Chinese language sites and find all the, and cross-reference things with each other, and find as much of Tencent's investment portfolio as I ..."
Creating Unique Resources
In this segment, Packy discusses a project where he compiled a list of sci-fi ideas and their real-world counterparts. He highlights the process of using AI tools to format and analyze the data, showcasing how unique resources can emerge from creative research and collaboration with technology.
"used ChatGPT to format the spreadsheet and get it into a place that was consumable. And then I used two different Anthropic accounts, because I would rate limit the Anthropic accounts back and for..."
Uncovering Hidden Gems in Writing
Packy reflects on the thrill of discovering unique sources and insights that enhance his writing. He shares a story about finding a leaked memo from Boeing that explained critical issues within the company, illustrating how uncovering hidden gems can lead to compelling narratives.
"really cool resource." And people, I think I still see people sharing this sci-fi idea bank, but it was just a couple of days of like, I'm going to flow on this research as much as I can. So this..."
The Value of Early Interviews
Packy discusses the significance of early interviews with successful founders, highlighting how their unfiltered thoughts provide valuable insights. He mentions notable figures like Mark Zuckerberg and Jeff Bezos, emphasizing the importance of authenticity in understanding their journeys.
"for them for sure. So there's the two different things. There's, can I give people this source in my writing and let them see it for themselves, and they've definitely never seen this before and..."
Using AI as a Writing Assistant
In this segment, Packy explains how he utilizes AI tools like ChatGPT and Claude in his writing process. He discusses their roles in providing explanations, editing assistance, and even serving as a thesaurus, showcasing the evolving relationship between writers and AI technology.
"Yeah. You mentioned Anthropic. How do you use AI GPT in your writing process? I use it to explain things to me. So I'll say, "Here's a phrase, explain this." And then I can ask a bunch of questio..."
The Balance of AI Feedback
Packy shares his thoughts on the feedback he receives from AI tools during the writing process. He emphasizes the importance of maintaining a balance between AI suggestions and personal voice, highlighting the potential pitfalls of over-reliance on technology in creative writing.
"That was exactly what I'm going for." And so there is a little bit of, as I'm going through these drafts, I'm like, I'm halfway through the piece, I'm like, "Man, I'm stuck here." It's almost how ..."
Exploring AI-Generated Imagery
Packy discusses his initial enthusiasm for AI-generated images and how he has adjusted his approach over time. He reflects on the importance of developing a unique style and the challenges of creating distinct visuals using AI tools.
"I don't even put the word in, "Here's the sentence, fill in blank." And so it'll maybe give me that word. And it's sometimes right, sometimes not, but it'll get close enough. I don't then use it..."
Monetizing Writing: A Unique Business Model
In this segment, Packy outlines his business model for monetizing his writing. He discusses the balance between sponsorship and content quality, sharing insights into how he has successfully integrated sponsored posts while maintaining audience engagement and trust.
"How do you think about the business model of what you're doing? You have the sponsored post, you have the investing. Talk to me about that. Yeah, so I have a couple of pieces on the business. I h..."
Behind the Scenes of Sponsored Content
Packy elaborates on the process of creating sponsored content, emphasizing the importance of authenticity and storytelling. He shares how he collaborates with companies to produce engaging pieces that resonate with both the audience and the sponsors.
"financials and things that only their investors would see. Sometimes we are an investor in the company, and so we have this behind the scenes access. And I'm trying to figure out what is a thing..."
Writing and Investing: A Symbiotic Relationship
Packy elaborates on the synergy between writing and investing, explaining how his writing provides access to founders and their ideas. He discusses the value of understanding the thought processes behind fundraising and how this knowledge enhances his investment strategies.
"all the things that you need as someone who companies are relying on to move money. And it's a little insight like that. This is an interesting way to manage an engineering team at a fast-growing..."
The Internet's Dual Nature
Packy reflects on the contrasting aspects of the internet, where loud opinions can either mislead or enlighten. He emphasizes his mission to help articulate well-thought-out ideas and encourages others to share their expertise, fostering a culture of informed discourse.
"the investing side, it's access. If founders read the newsletter, that's super helpful. They know how I think about the world. It helps there. I think on the other side, a fundraising process is..."
Attracting the Right Voices
In this segment, Packy discusses the importance of attracting individuals with deep insights while repelling those who lack seriousness. He shares his vision for Write of Passage, focusing on creating a community of dedicated writers who are eager to refine and express their unique ideas.
"with this podcast, with Write of Passage, is there are so many people in the world who have this core idea, something that they've spent years thinking about. Sort of like we were saying with the ..."
The Shift from Finding to Attracting Talent
Packy contrasts the pre-internet world of finding talent with the post-internet reality of attracting it. He highlights the significance of creating an environment that draws in passionate individuals with transformative ideas, emphasizing the role of effective communication in this process.
"those deep, crazy, deeply understood ideas? I think that this is the fundamental pivot point that the pre-internet world has versus the post-internet world is you use the word find. How do you fi..."
Conviction Over Perfection in Writing
Packy shares insights on the essence of good writing, arguing that conviction and unique life experiences often outweigh technical skill. He encourages aspiring writers to embrace their perspectives and emphasizes the importance of guidance in the writing process.
"but with attracting and repelling people. Yeah. You can challenge the how do you get them to write something really excellent, and it's almost like how do you... Because I think ideas, people or ..."
The Journey to Long-Form Writing
Packy recounts his transition to long-form writing, sparked by his experience in Write of Passage. He reflects on the challenges and breakthroughs he faced while developing his writing style and the impact of working with skilled editors.
"know. Can we do one really good piece? Totally. Yeah. I was thinking this coming into this, I've listened to the podcast, obviously follow a lot of the people that you've interviewed and I'm like, ..."
The Role of Editing in Writing
In this segment, Packy discusses the critical role of editing in the writing process. He emphasizes the need for constructive feedback that fosters improvement while maintaining the writer's confidence, highlighting the importance of a supportive editing relationship.
"it's not that... It doesn't have to be that much. Yeah. Yeah. Remind me how you got to writing long form pieces. I think was the fellowship that we did, was that, when you wrote Conjuring Scenius, ..."
Finding Your Writing Rhythm
Packy reflects on his writing routine and the balance between crafting thoughtful pieces and producing content regularly. He shares his thoughts on the evolution of his writing process and the importance of consistency in developing a body of work.
"You know what you wrote? You said, "My goal is to get 20 newsletter subscribers." Yeah. I tweeted that I needed... And it wasn't even a goal, it was an assignment from you guys, like, you needed ..."
The Art of Editing
Packy McCormick shares insights on the importance of effective editing in writing. He emphasizes that good editing involves providing constructive feedback without discouraging the writer. The segment highlights the balance between critique and support, showcasing how a skilled editor can enhance a writer's work while fostering confidence.
"read versions of it. And it was the first time I'd worked with an editor and be like, "Whoa." Everybody who worked with Tom in that fellowship said, "This guy is so good at editing." He was amazin..."
The Freedom of Regular Writing
In this segment, Packy discusses the liberating effect of writing regularly, moving from infrequent long-form pieces to producing substantial essays weekly. He reflects on how this shift in approach allows for more creativity and information sharing, emphasizing the importance of consistency in the writing process.
"of those things, it is a delight. And sometimes you get this holier than thou editor who's like, "What the heck is wrong with you?" It's like Cruella de Vil just stepping on you and you're just ..."
Unexpected Success with 'The Great Online Game'
Packy recounts the surprising success of his piece 'The Great Online Game,' which he initially thought was a throwaway. He reflects on how the piece resonated with readers by articulating a shared experience, highlighting the unpredictability of writing and the importance of capturing timely ideas.
"not the piece that I'm working on and it's just like, all right, I'm doing this every week, and so I'm going to just put as much information in this as I need to. It's not going to be perfect. I ..."
Writing for the Individual vs. the Masses
This segment explores the paradox of writing: when attempting to appeal to a large audience, writers often miss the mark. Packy emphasizes the value of writing with intimacy and authenticity, suggesting that connecting with individuals can lead to broader resonance and impact.
"Saturday that I thought was not that good. And so I threw it out Sunday morning and I just wrote that piece in a day really fresh from my idea to publishing, which even now is rare that I'll hav..."
The Challenge of Originality in Writing
Packy discusses the difficulty of creating original ideas in a saturated content landscape. He reflects on the challenge of finding unique expressions and the pressure of competing voices, while maintaining a belief in the potential for new insights and discoveries in writing.
"you can go play and like, "Oh, there might be this amazing opportunity on the other side." If I'd known so many people were going to read it and refer to it, I actually probably might not have wr..."
The Timelessness of Great Writing
In this segment, Packy and David Perell contemplate the enduring nature of impactful writing. They discuss the possibility of future texts achieving the same significance as historical works, considering the rapid pace of content creation in the digital age and the challenge of standing out.
"I think you're speaking to something deeply paradoxical about writing is that when you try to write for the stadium, you don't hit the stadium. And when you try to write for the individual, you'..."
The Complexity of Modern Ideas
Packy reflects on the complexity of modern ideas and the difficulty of creating something truly novel. He discusses how the saturation of information can make it challenging to produce groundbreaking work, while also expressing a conviction that new insights are still possible.
"that maybe I'll do it later in life when I'm in my 80s or something, but I really work hard on them and I write one every day. They're like 200, 250 words, takes about an hour and a half, and it..."
The Role of Faith in Writing
This segment delves into the philosophical aspects of writing and belief. Packy and David discuss the intersection of faith and creativity, exploring how personal beliefs can influence the writing process and the perception of timeless texts.
"like that again? Or because we're not spoken word anymore, because the internet moves so quickly, because there's so many people producing content is impossible to get that spot ever? Yeah. Well,..."
The Challenge of Novelty in Expression
Packy and David discuss the challenge of expressing novel ideas in a world filled with recycled thoughts. They explore the difficulty of creating impactful content that resonates with audiences while navigating the vast landscape of existing ideas.
"and fully God. And then even the other letters, the Holy Spirit was working through the hand of Paul and John and different writers in the New Testament, but this is actually a God thing, so it'..."
The Infinite Possibilities of Writing
In this segment, Packy expresses his belief in the infinite possibilities of writing and creativity. He emphasizes the importance of exploration and the potential for new ideas to emerge, encouraging writers to embrace the journey of discovery.
"just because there's so many ideas. Any combination and permutation of things either has been tried or somebody will try and will tweet. I think that's another challenge to doing it. Even this w..."
Finding Inspiration in Everyday Life
Packy shares his approach to finding inspiration for writing, emphasizing the value of engaging with diverse sources and experiences. He discusses how seeking out different perspectives can refresh creativity and fuel the writing process.
"so all of that I agree with. I think I'm probably also being short-sighted on the other side of this argument where it's just like there is this weird set of conditions where, to your point, there..."
The Power of Unique Perspectives
In this segment, Packy reflects on the impact of unique perspectives in writing. He shares an example of how a fresh take on a familiar emotion can unlock new insights, illustrating the importance of originality and depth in creative expression.
"on... We'll put neural links in it. There'll be the first great neural link communicator who's able to speak directly into people's brains, or there will be some other opportunity for that. Right..."
The Influence of Great Essays
Packy discusses the influence of great essays on his writing process. He highlights the importance of reading and engaging with well-crafted pieces to inspire creativity and refine his own writing style.
"know existed. It's like seeing a new color. And I'm like, "What?" And I think that the possibility for that is nearly infinite. That's amazing. And I kind of know what you're talking about, the s..."
The Quest for Mastery in Writing
In this closing segment, Packy reflects on the quest for mastery in writing. He emphasizes the importance of continuous learning and exploration, encouraging writers to seek out new ideas and experiences to enhance their craft.
"What's one of those essays? I love the essay Becoming a Magician by Autotranslucence. Great piece. I love that piece. Yeah, it's almost like ethereal, but you also really kind of feel it and you'r..."
The Puzzle of Understanding Greatness
Packy McCormick reflects on the allure of successful individuals and the challenge of deciphering their unique approaches. He shares his experience of revisiting essays that resonate deeply, capturing feelings and thoughts he struggles to articulate. This segment explores the importance of consuming diverse information and the creative potential that arises from allowing ideas to collide in one's mind.
"doing that you fundamentally cannot comprehend. And your attraction to them is the puzzle to try to figure out, what is it that they're doing? Yes. That one I try to read every time. It's a list ..."
The Art of Reading and Imagination
In this segment, Packy discusses his reading habits, emphasizing the value of fiction and sci-fi in expanding one's imagination. He explains how inhabiting futuristic worlds can provide insights into present-day ideas and business models, allowing him to recognize emerging trends and opportunities. This highlights the connection between literature and innovative thinking.
"Do you read a lot of books? I read a lot of books. Yeah. Fiction non-fiction, sci-fi I was doing for a little while, a little bit less of now. But love just to, I think for what I'm writing about ..."
Self-Discovery Through Writing
Packy shares his journey of self-discovery through writing, acknowledging the challenges of maintaining authenticity in his work. He reflects on how writing helps him uncover his true interests and perspectives, even when they diverge from audience expectations. This segment emphasizes the therapeutic nature of writing and the necessity of passion in producing engaging content.
"As you look at your writing, what is the biggest thing that irks you about it? This is something maybe that more irks me about myself. I wish that I had just a little bit more technical depth on ..."
Curiosity as a Driving Force
In the closing moments of the conversation, Packy and David discuss the role of curiosity in their writing processes. Packy expresses the importance of pursuing topics that ignite his passion, suggesting that genuine interest is essential for sustained creativity. This segment encapsulates the idea that writing should be driven by fascination and a desire to explore new ideas.
"not great for audience eyes or great for a bunch of these things where it's like, oh, this week I'm interested in this wild biotech company, and the next week I'm talking about space. It's exact..."