Per My Last E-mail #21

Writing, Debate, Sleep, Passion Economy, Friends, and Books

Hi Friends 👋,

Happy Monday! I hope many of you are enjoying the third day of a three day weekend, and for those of you reading this from an office, only a few hours left!


Last week, 2PM’s Web Smith wrote The Relevance of the Letter about the rise of Operator-First Publishers, people who have built companies and products and share their unique perspective through their writing. Smith points out that the new wave of newsletters provides a platform to people who might not otherwise have one because they don’t fit the pattern of the people we’re used to getting our knowledge from. He also highlights examples of people who have been able to build brands and businesses off the backs of their own content and distribution, focusing on media brands like Thing Testing, Lean Luxe, and 2PM itself.

I’ve been writing for about six months, since I took the Write of Passage course in April. Since then, I’ve written 21 newsletters, 22 blog posts, and about 50,000 words. I wouldn’t call myself a writer, but I’ve been writing. Similarly, I wouldn’t call myself an entrepreneur yet, but I’m starting the journey of starting something.

In that process, I’ve noticed, like Smith did, how helpful writing has been to me, in a few key ways:

  1. Overcoming Fear of Rejection

    I still get a little jolt of fear every time I hit send on one of these newsletters. I have an image in my mind of a group chat happening somewhere in which everyone I know talks shit on what I’ve written, and on the fact that I’m presumptuous enough to write in the first place. (Which would be totally fair, and if that group chat exists somewhere, no hard feelings.) But facing that fear is part of the reason I started writing and have stuck with it.

    Now that I’m working on starting something, it’s been really helpful to have faced the fear of people thinking that my ideas are stupid, incomplete, or not worth sharing in a small way, every week. The early phase of starting something is essentially a long series of conversations in which I tell someone smarter or more experienced than me the latest version of my idea, they give feedback, and then I go back to the drawing board. By definition, the idea isn’t fully formed yet and has a ton of holes, so each time I share it with someone, I’m a little bit embarrassed. And there’s just something scary about putting your idea, the thing that you’re saying is the best you got given all of the experiences and learnings that you’ve accumulated over your life, out there for people to judge. I suspect this feeling will never fully go away.

    But the hardest conversations, the ones in which people have poked the most holes or been most underwhelmed, have actually been the most fruitful. They’ve forced me to examine whether the idea is worth pursuing, and what would actually make it valuable to people. They’ve challenged me to keep improving before spending any money going down the wrong path.

    Without facing the weekly micro-fear, I would have likely avoided conversations that have been extremely valuable.

  2. Shaping and Strengthening Ideas

    There’s a popular idea in the startup world that ideas are cheap and that execution is what matters. Like any meme, it oversimplifies and misses some important nuance.

    If you define an idea as “I think it would be cool to do Uber but for haircuts,” then yes, the idea is worthless. This is a little-i idea.

    But if you define an idea as all of the research, writing, editing, discussion, market-sizing, and strategizing that you do before deciding to hit go and build something, ideas can be really valuable. This is a big-I Idea.

    Moving into execution without getting the Idea right is like driving somewhere you’ve never been without looking at a map; you’re going to waste a lot of time and fuel and end up miles away from where you meant to go. There’s a reason that companies like Amazon and Stripe prioritize good, clear writing.

    Building the writing muscle has been really helpful in the earliest stages of shaping the Idea. A little i-idea is like a tweet - you think about it for a second and let it fly. A big-I Idea is like an essay - you start with a kernel, add to it, search for supporting or negating evidence, keep adding, figure out what you’re trying to say, and to whom, form a narrative, edit, share it with a small, trusted group for feedback, refine your argument, keep editing, keep adding, keep editing, and then at some point, get it to a place where you feel kind of comfortable putting it out into the world. You can edit on the page before having to edit a real physical product in the real world.

    Getting a little bit better at writing has helped me to get a little bit better at strategy, and I’m a huge believer in the importance of strategy to direct all of the blood, sweat, and tears that you’ll have to put into execution.

  3. Attracting Like-Minded People

    One of the coolest parts of writing has been getting to meet and talk to really smart, helpful people who have a point-of-view on many of the things that I’m thinking about. Writing has allowed me to state publicly what I’m interested in, and has acted as a magnet to attract people who have spent a good portion of their personal or professional lives thinking about those same things. David Perell calls this aspect of writing the “Serendipity Engine.”

    By putting stuff out there in a place where it can live independently from me, I’m able to find more interesting people than I’d be able to if I just approached a bunch of random people on the street or in coffee shops (and do it in a much less creepy, annoying way than that). Looking at my calendar from the past couple of weeks, over 50% of meetings that I’ve had have been a direct result of my writing, including conversations with long-time friends who share interests that I didn’t realize we shared. (As I’m writing this, someone just reached out after seeing the IRL series featured in Lean Luxe.)

    One friend who recently started a company told me that the 0 - 0.1 phase of company creation is essentially just having conversations with a lot of people until you’re ready to launch. Writing has been hugely helpful in making those conversations happen.

I don’t want to overstate the quality or reach of my writing. I have a long way to go. But writing has been a really useful tool as I’m beginning this new adventure, so I wanted to defend thinking before doing against the people who would suggest that you should just get out there and do.

Debate Club Part Deux

Debate Club #1 was a blast, and #2 will be even better. For our second debate, which will take place in late October / early November, we’re going to revamp the rules a bit to make it more interactive, and open it up to more people. For those who sign up for Debate #2, I’ll reach out with more details, including a forum for evolving the format and rules together.

Speaking of which: sign up here!

In the spirit of debate and understanding both sides, check out this New York Times Opinion piece that Skyler sent me over the weekend: Are School Debate Competitions Bad for Our Political Discourse?

Links & Listens

😴 ‘It’s the dirty little secret that everybody knows about.’ by Baxter Holmes for ESPN

Ever since reading Why We Sleep by Matthew Walker, I have been obsessed with getting my eight hours. Not always successful, but obsessed. Puja makes fun of me for it - she can just put her head down and crash for ten hours, whereas I overthink it, wake up five times in the middle of the night, and give up after 7 hours. When I went to the office every day and had a calendar full of meetings, I could get by on less sleep without noticing it. But now that I’m fully relying on my brain working to make progress, I’ve noticed how hugely sleep impacts my performance.

Sleep is even more crucial when you need both your brain and your body working at 100% to succeed. This ESPN piece looks at the impact of NBA travel, schedules, and adrenaline on players’ sleep, and the impact that bad sleep has on players’ performance and likelihood of injury. Because of bad sleep, NBA players can go from testosterone levels in the top quartile of the general population to the bottom quartile in less than a full season, and they’re more likely to break down because of it. There’s no easy answer - one league source calls it “our biggest issue without a solution.”

💚 The Passion Economy and the Future of Work by Li Jin for a16z

Li Jin, a consumer investor at a16z, highlights the shift from the Gig Economy to the Passion Economy, in which “users can now build audiences at scale and turn their passions into livelihoods.” She gives examples such as online course creation, newsletter writing, and podcast recording - fields where individuality and passion are features, not bugs. Li focuses on digital platforms, but I think that the passion economy can and will extend into IRL communities.

👫 Average American Hasn’t Made a New Friend In 5 Years by Ben Renner in Study Finds

When I wrote about loneliness and unhappiness in Why Now, I missed one of the biggest factors: we’re not making new friends. 45% of respondents to an Evite survey admitted that they find it hard to make new friends, and the average adult hasn’t made a new friend in five years, despite the fact that 45% of respondents said that “they would go out of their way to make new friends if they knew how or had more opportunities to do so.” Despite missing this in my writing, we got to the same conclusion: “For the 45 percent who are looking to make new friends, the best and most underrated way to do that these days is still in-person.”

Thanks to Dror for sharing this article!

🎧 Cameron Porter: Invention On-Demand on The North Star Podcast with David Perell

Cameron Porter is a former-MLS-player-turned-investor at Alley Corp, where he helps found and fund companies in NYC. Learning about how Alley Corp thinks about creating companies is fascinating and worth sharing in its own right, but what really got me was that Porter and I share similar views on the importance of IRL community. “We no longer have institutions guiding us into this group formation… What would it be like to create one of those?”

Bonus points for his obsession with Loonshots.

What I’m Reading

The Righteous Mind by Jonathan Haidt

Mike Madonna is one of my most thoughtful and well-read friends. When he told me that he’s read The Righteous Mind three times and that it’s meaningfully changed the way he views the world, I downloaded it and started reading immediately. I’m only 12% in right now, but I’m already digging Haidt’s approach to deep questions around our morality and why we make the choices and judgments we make. The book has some definite Tim Urban The Story of Us vibes; I’m reading both together, and the combination is giving me a better framework for understanding human motivation, politics, and group dynamics.

Building the Intentional University by Stephen M. Kosselyn & Ben Nelson

Many of you have probably heard about Lambda School, the coding bootcamp that has caught fire by offering its students coding training and not making them pay a dime unless they make at least $50k per year after the program (I wrote about Lambda here). But an even more groundbreaking project is underway in the education space. Minerva is building the university of the future from the ground up - re-imagining the classroom, the campus, the curriculum, and even the goals of a modern education.

Building the Intentional University explores in detail the philosophy and execution behind building a college that “develops intellect across multiple disciplines, as well as critical life skills, professional capabilities, and key aspects of personal character.” One of the most fascinating aspects to me is that they harness what the internet does best while also enabling students to connect IRL. Each semester, Minerva students live together in a different major world city, and take courses online. Professors can teach from San Francisco while students immerse themselves in the daily life of cities like Hyderabad and Berlin.

It’s an incredibly ambitious undertaking, building a truly Natively Integrated Education, with a world-class team behind it, and I’m watching what they do closely.

Book Bonanza

Polina Marinova writes two of my favorite newsletters: Term Sheet and The Profile. In last week’s installment of The Profile, she announced a contest inspired by Bill Gates’ Think Week: she would send one lucky winner a tote bag full of books. I am that one lucky winner. I’ll share the full list here next week, it’s bound (pun intended) to be chock full of great reads.

Know anyone who is interested in IRL community-building, education, debate, or anything else that I’m writing about? I always appreciate you sharing Per My Last E-mail with friends. They can subscribe here, or reach out to me @packym on twitter or at

Thanks for reading!