Per My Last E-mail #24

Mexico, Three Book Recs, Lunchclub, The Wing, and Scenius

Hi Friends 👋,

Happy Tuesday from Mexico City!

Puja and I are going to our friends’ wedding here on Saturday, so we came down a few days early to experience Dia de los Muertos, explore more of the city, and set a Guinness World Record for number of tacos eaten in a 10-day period. I’m proud to report that two days in, we’re ahead of pace and showing no signs of slowing. Because those tacos don’t eat themselves, I’m going to keep this week’s e-mail (just a little bit) shorter.

What I’m Reading

What I’m Reading gets the place of honor right up front this week because the concepts in these books are helpful in understanding some of this week’s Links & Listens.

Vacation means more reading time, so since my last e-mail, I’ve been able to finish three excellent books: The Righteous Mind by Jonathan Haidt, What You Do Is Who You Are by Ben Horowitz, and Get Together by Bailey Richardson, Kevin Huynh, and Kai Elmer Sotto. These feel like books that I’m going to keep coming back to, and I’d recommend them to any of you who are interested in how humans feel, think, and behave, individually and when we form groups.

Since you’re going to read each of these books, I won’t spoil them. I’ll just give one takeaway from each, and will revisit some others in the Links & Listens section below.

The Righteous Mind by Jonathan Haidt

One-Sentence Summary: A scientific exploration of how human morality and decision-making work, and what that tells us about politics, religion, and culture.

Takeaway: We make decisions based on emotions, and use our reason to justify all of the gut decisions we make. Haidt likens our emotions to an Elephant and our reason to a Rider. The Rider seems to be in control, but the Elephant is so large that the Rider is often just responding as quickly as it can to the decisions the Elephant makes. Haidt uses the Rider/Elephant analogy to help explain why we can’t settle disagreements with reason, why we need to motivate the Elephant with emotional appeals, and why we often make decisions that confuse even ourselves.

What You Do Is Who You Are by Ben Horowitz

One-Sentence Summary: A former CEO-turned-VC shares historical lessons and practical advice on building culture.

Takeaway: In order to clarify your culture, you need to create shocking rules. Rules that make everyone who has to follow them ask, “Why?” and an answer that solidifies a key aspect of the culture. Touissant Louverture, the Haitian slave who led the only successful slave revolt, created a rule against infidelity among his troops, even though infidelity was a common part of, and even a reward for, war at the time. Why? Because he needed a culture of trust, and if soldiers’ families couldn’t trust them to honor their commitments, how could they trust each other?

Get Together by Bailey Richardson, Kevin Huynh, and Kai Elmer Sotto

One-Sentence Summary: A guide to creating, growing, and sustaining communities from three of the best in the community-building game.

Takeaway: This is going to serve as a go-to resource as I work on building a community; I highlighted at least three things on each page. But the thing that struck me most about Get Together was how well it was written for the purpose it’s trying to serve. It’s short, doesn’t unnecessarily repeat itself, provides the right amount of illuminating case studies, and re-iterates the most important pieces in checklist form at the end of each chapter. Wayyy more business books should be written this way.

Links & Listens

🦸‍♀️ The Wing: How an exclusive women’s club sparked a thousand arguments by Linda Kinstler in The Guardian

The Wing, a “network of work and community spaces designed with [women] in mind,” is as controversial as it is beloved. It has ardent supporters, and detractors who pick apart its every move - it’s been criticized for being unwelcoming to people of color, for being too elitist, and has even been sued by men who believe they should have the right to join the women-only club.

Some of the people who are upset with The Wing are those who can’t join - because they’re male, because they don’t feel they belong, because they can’t afford it. But many of The Wing’s detractors are its own members; the same people who defend it against external criticism are the ones who attack it themselves. So what’s going on? I think we can find some of the answers in Get Together and The Righteous Mind.

  1. Get Together introduces Robert Putnam’s idea that there are two types of communities - those based on bridging social capital and those based on bonding social capital. Bridging communities bring together people of different demographics based on shared interests, whereas bonding communities bring together and strengthen bonds among people with similar backgrounds. The Wing is a bonding community, and as such, it naturally upsets people outside of its group. In many cases, the fact that outsiders attack it makes those on the inside feel an even stronger connection to each other.

  2. More interesting is the fact that even people inside The Wing community are often vocally opposed to its policies, even while remaining actively involved and supporting it against outsiders. In The Righteous Mind, Haidt writes about the fact that we are 90% primates and 10% bees, meaning that we operate on two levels: 90% of the time, we compete against each other as individuals within our group, but 10% of the time, we operate as part of one whole. At certain points, a “hive switch” goes off, and we move from thinking of ourselves as individuals to thinking of ourselves as part of a larger whole. Think back to the 9/11 attacks. Americans who opposed each other on every issue on 9/10 came together as Americans on 9/12. We stopped hating each other, and started hating our enemy together. Haidt cites an old Bedouin proverb: “Me against my brothers; my brothers and me against my cousins; my cousins, my brothers, and me against strangers.” The Wing members fight against each other internally but then have the group’s back when threatened externally.

It’s pretty crazy to realize how much of human behavior is so predictable.

(Relatedly, Ethel’s Club opened its doors in Brooklyn yesterday, and Union Social Club shut its doors in Durham over the weekend. Point: bonding communities. I was a fan of Union Social Club’s mission of creating a more accessible space and bringing together people from diverse backgrounds. Bridging definitely ups the degree of difficulty in attracting and retaining early members and building a sustainable business model, though.)

🤓🤓🤓 Scenius, or Communal Genius by Kevin Kelly

This is an oldy but a greaty. In 2008, Kelly wrote about a term coined by the musician Brian Eno, scenius: “the intelligence and the intuition of a whole cultural scene. It is the communal form of the concept of the genius.” Examples of scenius include Ben Franklin’s Junto, Vienna Circle, the Bloomsbury Group, The Other Club, MIT’s Building 20, and Burning Man.

Kelly argues that scenius can’t be intentionally created, that it emerges out of the presence of the right early pioneers, the right time, the right generic, flexible space. I agree with Kelly that scenius is difficult to create within the context of a startup or a city - each has its own goals, timelines, and performance standards apart from creating scenius, and enabling the requisite weirdness and freedom to thrive in either context without the certainty of a positive outcome is more of a risk than companies or cities are able to bear.

But half of the battle is just getting the right people in the right place at the right time and giving them the room to do their thing, and I do think you can create that. I wonder what happens if you create a system that thrives independently of any particular outcome, in which the organization wins just by making a place and a community that attracts the type of people who create scenius.

South Park Commons, which not surprisingly says that it draws inspiration from sceniuses Junto and the Bloomsbury Group, feels like it’s on to something. In just over two years, more than 20 companies have been launched out of SPC, including Lunch Club (see below). By providing the right space and putting smart, creative people together, they’re showing early signs of success in creating scenius. I’m taking notes.

🇲🇽 Bonus Watch: Coco

The next best thing to celebrating Dia de los Muertos is watching Coco, and then getting excited enough to come down here for it next year’s festivities.


This week’s Product of the Week is

Image result for lunchclub

Last Friday, I had coffee with someone I’ve never met before. He wasn’t introduced to me by a friend, an acquaintance, or even a human being. Instead, an algorithm thought that we would be able to help each other, and it turns out that it was right.

Lunchclub is a startup that was born in South Park Commons, which I wrote about in The Rise of IRL Member Communities. It uses machine learning to discover mutually beneficial connections and helps find a time for the mutually beneficial pairs to meet up IRL. Each week, on Monday, Lunchclub checks in to see when you’re available that week and where, and then follows up with an introduction to a new person it thinks you should meet.

I kept hearing that people were surprised with how spot-on the connections were, so I decided to give it a whirl. Once I got off the waitlist, Lunchclub made its first introduction within a couple of days. From the intro e-mail they sent to both of us, I was blown away by the accuracy of the match.

In-person, it became even more apparent that they had nailed it. The person I met with had worked in finance, like me, and was working on starting an IRL Member Community, like me. Because neither of us had reached out to the other, we came into the conversation on equal footing, and because of the similarities in our backgrounds and interests, we were able to dive right in and start providing feedback and helpful tips to each other. Since we met on Friday, we’ve been e-mailing back and forth, and it feels like this relationship is going to continue to be valuable.

I’m definitely going to let Lunchclub work its magic again. If you’re in New York, SF, London, LA, Toronto, Boston, Seattle or Austin, I’d highly recommend seeing who it can connect you to. You can sign up at my link here.

What’s Next

This Wednesday, we’re locking in a date and location and selecting teams for Debate Club Part Deux. Last call for signups here.

In the meantime, of course, more tacos.

Thanks for reading!


Per My Last E-mail #23

Know Thine Loop, Otis, Humans, Time, Myers-Briggs, and IRL

Hi Friends 👋,

Happy Monday! It’s going to be a spooktacular week. 👻

Not sure what to give trick-or-treaters? 10 out of 10 dentists agree that Per My Last E-mail Subscriptions cause fewer cavities than Skittles or Reese’s Peanut Butter Cups.

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Know Thine Loop

Know Thine Loop

Kevin Kwok is on the shortlist of people who write infrequently enough and with so much quality information density that I’ll share everything they write. His latest, Notes on Superhuman’s Acquisition Loops, sounds dry and technical, but it’s packed with wisdom nuggets.

To understand why, we need to start by defining Superhuman’s strategy as simply and succinctly as possible: Prime people to want to use Superhuman, then delight fervent users so that they refer more users.

According to Kwok, everything that Superhuman does is in service of this strategy. Its actions are linked. When the loop works, it works really well, in a way that can't be easily copied by mimicking one or two tactics.

This is what I love about Kwok's writing: whereas most people have tried to cherry-pick lessons from Superhuman (examples here and in the thousands of results here), he examines their discrete actions in the context of a larger loop.

He points out that, “All companies want to delight the users who would be most disappointed to lose the product, but this often comes at tradeoffs with other priorities.” Cherry-picking tactics without making the necessary tradeoffs is useless and potentially harmful. Take, for example, Superhuman’s onboarding.

Superhuman pays a human being to spend at least 30 minutes onboarding every single person who signs up for the product, which creates additional cost for Superhuman and additional friction for the customer trying to sign up. Because the onboarding fits into Superhuman's loop - it creates delight, which causes people to talk about Superhuman, and teaches people to use the product, which creates fervent users, about Superhuman - it makes sense for them to do. Because Superhuman has shown early success, people think that they can also be successful if they provide white glove onboarding.

But trying to duplicate Superhuman's success by implementing a similar onboarding process without replicating its $0 CAC or reliance on evangelists would be like trying to become Walmart by underpricing all of your competitors without having built Walmart's scale and supply chain. Both will both wreck your unit economics and could kill your business.

Copying part of a strategy is dumb and lazy. I think this is why Web Smith wrote, in The DTC Playbook is a Trap:

There is no playbook. DNVB growth must be a malleable and agile operation. Brands must find opportunities where there were none. They must seek to do what hasn’t yet been done.

I’m going to write more about the importance of differentiation - doing things and building loops that only you or your company can do - over the coming weeks and months. For now, my takeaway from Kwok’s note is:

Don't steal tactics blindly; know thine loop.


Introducing a new segment: Product of the Week. May just be this week, may be ongoing.

This week’s P.O.T.W. is Otis, which allows its members to buy fractional shares of cultural assets like art, sneakers, and comic books for as little as $25.

Last week, it dropped its first asset: Saint Jerome Hearing the Trumpet of the Last Judgment by Kehinde Wiley. If that name sounds familiar, that’s because Wiley painted President Obama’s official portrait.

Since the assets that Otis sells are owned by a group of retail investors, not one particular person, Otis acts as their custodian. Which means that they’re able to display them for the public to see, which they did in the East Village yesterday. I went to check it out.

I’m not an art person or a collectibles person. But seeing the pieces IRL while knowing that I could own a piece of them gave it a different vibe than going to an art museum. I could see myself owning a little piece of a KAWS painting, Jeff Staple’s SB Dunks Collection, Nike Air Mags like the ones in Back to the Future, or the Takahashi Murakami x Virgil Abloh collaboration.

Otis is part of a growing number of companies taking advantage of Reg A+ from the JOBS Act, which enables private growth-stage companies to raise money from all Americans, not just accredited investors. Others include Rally Rd., which lets you own a fractional share of classic cars, and StockX, recently valued over $1 billion, which has created a stock exchange for sneakers.

What I love most about all three companies is that they lean into the nature of the products they list by creating IRL experiences (Soho is the epicenter) that match their brand and their target customer. They’re building an online-offline loop.

Kwok wrote that “Social capital–not personal utility–is what drives Superhuman’s acquisition loop. Users don’t share Superhuman because they need others to use it for it to work; they share it because they want to.”

Otis, Rally Rd., and StockX are creating a new asset class, and they need to lean into the social capital generated by the early adopters showing off the cool thing they just bought in order to make investing in art, sneakers, and exotic cars more mainstream. Expensive investments like retail space in Soho fit into that loop because they reward early adopters with a place to show off the cool thing they bought, and build trust with potential new investors in a way that only IRL can.

Links & Listens

🤖 Eliminating the Human by David Byrne in the MIT Technology Review

When I wrote about the role that technology is playing in making us lonelier and less happy, I assumed that making us interact with each other less was an unintended consequence of progress. Byrne isn’t so forgiving. He argues “that much recent tech development and innovation over the last decade or so has an unspoken overarching agenda. It has been about creating the possibility of a world with less human interaction.” It’s a bold claim, which he explains by pointing out that technology is built by male engineers, who are, as a group, loners who would seek to minimize human interaction.

We evolved as social creatures, and our ability to interact is one of the main reasons for our success. “If less human interaction enables us to forget how to cooperate,” Byrne suggests, “then we lose our advantage.”

The silver lining? We’ve eliminated things like going to the grocery store and standing in bank lines, freeing up time for more fulfilling human interaction if we let it.

⌚️ The 2010s Broke Our Sense of Time by Katherine Miller in BuzzFeed News

This piece opens in one of my favorite places in the world: that great melting pot of a cobblestone street where tourists from all over the world to take a picture with the second best bridge within a mile, the Manhattan Bridge. Like this 👇🏻👇🏻👇🏻.

“That’s a fine shot!” one bridesmaid lovingly called to a bride — who stood without the bridge in the background. “That’s a fine shot!”

We’ve spent the past decade - the decade that brought us Instagram, WhatsApp, binge watching Netflix, constant news alerts, and President Trump - in a new, disorienting relationship with time. Miller compares it to a Black Mirror episode. Yet another reason to pull our heads out of our phones and reconnect IRL.

👨🏻‍🔬The Comforting Pseudoscience of the MBTI by Anne-Laure Le Cunff of Ness Labs

Last week, we debunked the Stanford Prison Experiment. It’s a famous experiment and you’ve probably heard of it, but you’ve almost certainly never applied it to learn more about yourself. So this week, let’s get personal: The Myers-Briggs Type Indicator.

If you’ve worked, you’ve probably taken the MBTI at some point. I’ve taken it double-digit times. (I just took it again here and got INFP, but I’ve gotten ENTJ, ENTP, and INFJ before, so who knows!) But guess what? Turns out the MBTI is bullshit, too.

Le Cunff breaks down the MBTI’s history and why the test doesn’t hold wanter. She also introduces a phenomenon that helps to understand why we all believe our MBTI results (and horoscopes, and palm readings), despite their unreliability: The Barnum Effect.

“The Barnum Effect is the phenomenon that occurs when individuals believe that personality descriptions apply specifically to them, despite the fact that the description is actually filled with information that applies to everyone.”

As an alternative, I recommend the Enneagram Test, which I recently took and applied with my coach. It was eerily accurate, and not just in a Barnum Effect kind of way.

Whats Next

Last week was jam-packed with IRL Member Community exploration. I visited Union Social Club in Durham (pic below), met with a founder who’s getting ready to launch an IRL Member Community with an important twist in SF, went to the first OnDeck Fellowship dinner in NYC, and got off the Lunchclub waitlist (you can sign up here).

This week, I’m continuing to explore spaces and meet people. If there’s a place you think I should check out or a person I should meet, let me know!

Finally, we’re circling in on a date for Debate Club Part Deux in mid-November. New people, new rules, same nerdy fun - sign up here to join us.

Thanks for reading!


Per My Last E-mail #22

Baader-Meinhof, Stanford Prison, China, Tyler Perry, and Memos

Hi Friends 👋,

Happy Monday! It’s start-of-NBA-Season-week! And this season is a special one - Brett Brown’s optimism will pay off and the Sixers will win their first NBA Championship since 1983. On to the non-sports…

Baader-Meinhof’ed: Happiness, Education, and Friendship

Image result for baader-meinhof phenomenon

The fall of 1977 in Germany was known as “German Autumn.” That fall, the Baader-Meinhof Group, a West-German far-left militant organization, went on a spree of bombings, assassinations, kidnappings, bank robberies, and police shootouts that led to 34 deaths and earned the gang classification as a terrorist organization.

Until recently, I’d never heard of the Baader-Meinhof Group. And until one random day in 1994, neither had a man living outside of St. Paul, Minnesota. Then, one day, he heard about them for the first time. And within less than 24 hours, in a totally different context, he heard about them for a second time.

He took to the comment section of the St. Paul Pioneer Press to coin the term “Baader-Meinhof Phenomenon” for that thing that happens when you learn about something and then start seeing that thing everywhere. It’s what Stanford linguistics professor Arnold Zwicky calls the “frequency illusion”. And it’s what’s probably actually happening when you think that Instagram listened to you before creepily serving you an ad for something you were just talking about!

The phenomenon is caused by two psychological processes. Selective attention causes you to subconsciously start looking for something once you know about it, and confirmation bias reinforces your belief that each new sighting of that thing is proof that it’s everywhere.

I tell you all of this because a) I think it’s fascinating, and b) I’m being Baader-Meinhof’ed by happiness, education, and friendship. Since I started pulling the thread on these topics a couple of months ago, my selective attention has found happiness, friendship, and education everywhere I look.

To wit, in Part 1 of the Finding Our Place Series, I spent 1,316 words explaining that our smartphone addiction is making us unhappy. Then this week, I stumbled on this 2016 music video for “Are You Lost in the World Like Me?” by philosopher-DJ, Moby, and the illustrator-animator, Steve Cutts. Without having gone deep on technology’s impact on our happiness, I would have likely thought, “Weird song, creepy animation,” and moved on. Instead, because of Baader-Meinhof, I thought, “Woah. YES!”

(This video led me down a rabbit hole of Steve Cutts’ animations. They’re really creepy and really good. You can check them out here.)

I also just discovered The Happiness Lab podcast for the first time, although it’s been around since July. Dr. Laurie Santos’ episodes on Caring What You’re Sharing and Mistakenly Seeking Solitude were full of nuggets that triggered my confirmation bias.

The Baader-Meinhof Phenomenon is also hitting me hard on the future of education. I see it everywhere.

On Tuesday, the Wall Street Journal reported that business school applications are down 9.1% over the past year. According to the Journal, “a hot domestic job market has cooled the interest of many Americans in the traditional two-year M.B.A. path. Millennials, many of whom are saddled with debt loads from their undergraduate degrees, have proved more reluctant than previous generations to pursue the pricey degree.”

Just because business school applications are down doesn’t mean that people no longer want to learn and build their networks outside of the workplace. Companies like Jolt in London and even Harvard, through its Harvard Business School Online program, are offering new, more flexible, lower cost options.

Later in the week, I stumbled upon a piece that Byrne Hobart wrote about another relatively new education alternative. He argues that the college education is a bundle that has gotten too bloated, and that Ivy League schools are essentially focused on appraisal (of students when they’re 18) and signaling (to future employers). So what would the Ivy League look like if it were stripped down and rebuilt as a signaling-focused product? Y Combinator.

Its 12-week startup program provides appraisal, networking, job-specific projects, financing, and introductions to even more financing. Importantly, although it focuses on tech companies, the interactions happen IRL. [Nodding head vigorously in agreement.]

In addition to noticing things myself, I’ve noticed something else happening that puts selective attention and confirmation bias on steroids. It’s a social Baader-Meinhoff. Let’s call it the Group Baader-Meinhoff Phenomenon. Once you see something, and then start seeing it everywhere, and then talk about it or write about it, people who you talk to or who read what you write start to see that thing everywhere, and then they send you things they see, which means that you see that thing in even more places. That WSJ article on business school? My friend Kirk sent it to me after reading The World in Equilibrium. And the Happiness Labs podcast was shared by another loyal reader (hi mom!).

This has been happening a lot with regards to friendship. Before last week’s e-mail, Dror sent me the study that found that the average American hasn’t made a new friend in five years after we spoke about IRL Community in-person. It was the most clicked link in last week’s e-mail. Then last week, my dad sent me this Atlantic article: Why You Don’t See Your Friends Anymore. (I’m nervous to see what ads I get targeted with after reading all these articles about not having friends.) The takeaway from this one?

Staggered and marathon work hours arguably make the nation materially richer—economists debate the point—but they certainly deprive us of what the late Supreme Court Justice Felix Frankfurter described as a “cultural asset of importance”: an “atmosphere of entire community repose.”

Here’s where the confirmation bias comes in. When I see the Moby video, or read quotes like the one above, or when people send me things that they’ve found that relate to the things I’m interested, I think, “Wow, I’m really on to something here.” Even though I know about the Baader-Meinhof Phenomenon, it feels good to think that I’m right about something.

I haven’t figured this one out yet, how to balance the knowledge of the phenomenon with the idea that you may just be right. Sometimes, something is actually part of the zeitgeist and it’s not just your brain playing tricks on you. I do think that this is one of the reasons that so many companies launch with an idea that they think is brilliant, only to find that customers don’t care or are not willing to pay for what they’ve built. Part of the answer lies in actively trying to debunk your own ideas, and in asking people to call out your blind spots.

So an ask: if you think that I’m off-base on the things that I’m writing about, call me out! And of course, keep on sharing.

Links & Listens

🎧 Debunking the Stanford Prison Experiment on the Rationally Speaking Podcast with Julia Galef and Thibault le Texier

🙅🏻‍♂️ Debunking the Stanford Prison Experiment by Thibault le Texier

Image result for stanford prison experiment author

Speaking of wanting your ideas to be right so badly that you’re willing to completely fudge the design and results of your study…

In Per My Last E-mail #13, I linked to the le Texier paper above, but didn’t provide any commentary. Then I came across the Rationally Speaking podcast episode on which Galef interviewed le Texier about his findings, and was blown away. Essentially, this famous study from the 70’s, in which Stanford students were supposedly randomly assigned the role of prisoner or prison guard and supposedly responded by behaving like animals, was bullshit.

According to le Texier, the study’s author, Dr. Philip Zimbardo, made a bunch of experimental no-no’s. He was involved in the study himself, told the participants the outcome he wanted to get, and enforced rules that would help him get that result. He did this because he wanted to encourage prison reform more than he wanted to discover some truth about human behavior.

Interestingly, even though le Texier has shown that the results are at least questionable, psychology professors continue to teach the Stanford Prison Experiment. They, too, have their own goals: they want to show students that psychology is interesting and important, and this study is jarring enough to make that point. They might even be able to rationalize away the evidence against the study because they want it to be true.

Confirmation bias is a powerful thing.

🇨🇳 China Thread by Cyan Banister (click tweet below to see full thread)

At the risk of offending LeBron James, let’s talk about China. Banister’s thread highlights that China is playing the long game, and playing it with a different set of rules than we play by in the US. As an example, Banister points out that you can get autonomous vehicles on the road much more quickly if you’re OK trading off a few casualties short-term for millions of lives saved long-term. China is OK with this trade-off; the US is not.

This is nothing new. China has been playing the long game for years. But this conversation has gained a new level of prominence in the past few weeks because they messed with things less esoteric than tariffs or cybersecurity. They messed with our sports and with our video games. The Daryl Morey Incident and the Blizzard’s banning players for pro-Hong Kong speech have opened the country’s eyes to the Chinese threat in a way that even a trade war couldn’t.

For a nuanced look at what we’re facing, Ben Thompson’s The China Clashis required reading on the subject.

🍿 How Tyler Perry Built a Customer-Centric Empire by Dan Runcie in Trapital

Tyler Perry is a director/producer/actor best-known for the Madea franchise. He’s worth an estimated $600 million. But his success didn’t come easily.

He started out writing and acting in Madea plays in the south. On his first attempt, which he financed with his entire $12,000 life savings, he expected 1,200 people to show up. 30 did.

But Perry kept working and found success when he focused on getting the word out through the southern black church circuit and writing plays that would speak to them. As more people turned up, he collected their e-mail addresses, building a direct relationship and distribution channel. Even while his popularity grew and he started producing movies, critics panned his work. He didn’t care. He knew who he was creating for, and kept his focus on his audience.

After reading this Trapital article, I think that Perry should be up there with Southwest, Netflix, and the rest in the pantheon of strategy case studies. Throughout his career, he has been willing to make the trade-offs required in every aspect of his work and business to build a successful and sustaining empire. Highly recommend this read.

📝 Memos by Sriram Krishnan

Any list that includes Sam Hinkie’s resignation letter is a good list in my book, and this one put together by Twitter PM Sriram Krishnan, is a really good list. It includes classic internal memos like Sequoia’s YouTube investment memo, Nokia’s Burning Platforms, and Neil McElroy’s memo on creating dedicated brand teams at P&G, among some others that I’d never heard of.

Debate Club

The second Debate looks like it’s going to be bigger and better than the first! We have some new faces and returning, newly-experienced ones, doubling the number of participants and number of rounds. It’s starting to look like a real tournament 👀

If you’ve signed up - thank you! I’ll e-mail you separately with details in the next couple of days. If you haven’t, it’s not too late! Sign up here.

What’s Next

On Wednesday, I get to go back to my favorite city in the south, Durham, NC, to check out Union Social Club in person and eat at the best Indian restaurant in the USA.

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!


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!


Image result for writing

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 Ji Lin for a16z

Ji Lin, 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. Lin 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!


Per My Last E-mail #20

The Next Chapter, The World in Equilibrium, 3 Great Links

Hi Friends 👋,

Happy Monday! This is a big Monday for me: it's the start of my first week without a job in almost six years.

Six years ago, in August, I decided to turn down business school just to interview with Breather. There was no guarantee of a job (the role I was going for didn't even exist at the time), I had already quit my job at Bank of America Merrill Lynch, and Breather was the only place I was interviewing. It was risky, and probably dumb, but my goal from before I left college was to start a company, and I thought Breather would offer me the best opportunity to learn how to do that.

Thankfully, after four months, over Thanksgiving weekend, I got the NYC General Manager job as Breather's first US employee.

Working at Breather was the best professional decision I've ever made. Over the past six years, I've gotten to learn by doing with some of the smartest, most passionate, and best people I've ever known. I've learned what it takes to get a business off the ground, how much blood, sweat, and tears go into making it work, how to build and lead a team, how to manage people who are smarter and more talented than me, how to craft a strategy and act on it, how to run an extremely complex operation while increasing quality, and so much more. I feel incredibly fortunate for the experiences that I've had and the friends that I've made in my time at Breather, and incredibly proud of what we built together.

Now, it's time for the next adventure... which brings us to Part 4 of Finding Our Place.

(If you haven’t read the other essays in this series, start here, or just jump to the end 👇🏻)

The World in Equilibrium

We become what we behold. We shape our tools, and thereafter, our tools shape us. — Marshall McLuhan

We shaped the internet - an always-on network in the palm of our hands - and the internet has undeniably shaped us. The results aren't good.

Let's quickly recap what we discussed in Parts 1-3.

We're not happy. We thought that we could use the internet to build community, but it's harming us more than it's helping. But while it isn't a good replacement for face-to-face interaction, the internet does make it incredibly easy to get things done quickly and with minimal effort, freeing up time to spend together.

An early response to this issue is a rise of IRL Member Communities. These clubs, mainly organized around identity and interest, offer members a sense of belonging, creativity, community, and transformation. And they are just the beginning.

Macro trends - The Death of Retail, The Experience Economy, and Work's New Job - have set the conditions for an explosion in IRL Member Communities. Newly vacant retail space is looking for a new purpose, consumers are exhibiting a willingness to pay for experiences and community, and we're starting to separate work from the rest of our lives.

Now it's time for the fun part: imagining what the world will look like when we find a balance between the things we do online and the things we do offline.

The Online-Offline Equilibrium

By enabling one-click shopping, lightning-fast information retrieval, and work from home, the internet frees up time and resources that we can spend to make ourselves happier. The question is: what do we do with all of that extra time and capacity?

There are two bad options. Let's not do these:

  1. Parkinson’s Law states that work expands to fill the time available for its completion. According to Parkinson's Law, all that time we get back, we will reinvest into overcomplication and procrastination. We will do less in the same amount of time and be no better off for it.

  2. Or, as Wall-E predicts, we will spend our extra time growing fat and lazy while we live in a virtual reality and have our every whim attended to by the machines.

People need meaning. We need to feel that others rely on us, that we are making a positive impact, and that we're here for a reason.

So the option that I'm hopeful for is a third option, the online-offline equilibrium:

By combining what the internet does best with what we do best IRL, we will build comprehensive solutions to opportunities that have only been half-solved to date.

We will do more and more basic work online - buying goods, finding information - and then we'll sign off and head to offline spaces where we can spend time with each other, strengthening our communal bonds, improving ourselves, and just having fun.

Combined with the trends discussed in Part 3, this will translate into a massive rise in IRL Member Communities in which we pursue our passions, grow, slow down, make new friends, and re-connect with old ones.

When every town doesn't need retail space that sells every thing, we can repurpose that vacant space into clubhouses, community centers, spiritual hubs, wellness centers, classrooms, human-centered retail concepts, and fitness experiences that make us feel connected to a larger whole.

The implications of this shift will impact how we shop, how we gather, how we work, how we workout, how we live, how we learn, and how we meet each other.

I joined to a Book Club recently, and in our last meeting, we discussed the importance of serendipity in Amor Towles' Rules of Civility. Chance encounters, and how you act upon them, can shape your entire future. But the book was set in the late 1930's, and so the conversation turned to whether or not the same things happen today.

Is it serendipity if you find your future husband on Tinder? Or if you see that your mentor is connected to your dream future employer on LinkedIn and ask for an introduction? While it's easier than ever to connect with people, it doesn't feel better than ever.

But this current moment offers us a full digital and physical toolkit the likes of which we've never had access to.

Before, we had bars. Then, we had Tinder. What happens if you combine the best of both of those? What if you could find a group of 100 people in a city who are the best matches for each other, put them in the same space IRL, and allow for serendipity and face-to-face interaction to do the rest? Like church speed dating with a group of high-likelihood matches. I'm admittedly an outsider here (I missed Tinder by about six months), but that kind of solution feels like it would bring some of the magic back while also increasing the chances that you find the right match.

You can play out the same thought experiments for almost anything that we do online - from Neighborhood Goods reimagining how we shop our favorite DTC products, IRL, to Book Clubs making a comeback fueled by internet recommendations and in-person meetups.

To me, the most fascinating opportunity is in fixing the way we learn.

Unbreaking Education

If you remember going to the library and needing to use the Dewey Decimal System to figure out where the book you want to find might be, here's a crazy thing to contemplate: someone who is reasonably good at at using the internet who has a healthy motivation and work ethic can teach him or herself anything.

From counting to quantum physics, ABCs to DFW, there's a slew of articles, podcasts, YouTube videos, and even full courses, online, for free on the subject. The graphic below shows just some of the largest companies that provide educational content at no or little charge.

But MOOCs and other forms of online learning haven't led to the seismic shifts in education that some predicted. In fact, in The MOOC Pivot, MIT researchers Justin Reich and José Ruipérez-Valiente found that only 3.13% of people who enrolled in an EdX course actually completed the course. And the Brookings Institute found that students who would have gotten a B- in an in-person course get a C if they take the same course online. (For a more in-depth look into the shortcomings of online education, check out a recent piece that I wrote, Why There Isn't a Dominant Aggregator in Online Education.)

I think that online education suffers from the same challenges we have seen throughout this series. Namely, for most of us, learning requires the engagement, accountability, and connection that comes from IRL interaction.

People predicted that online education could fully replace in-person education, but it turns out that thus far, online education has been a useful supplement instead of a new paradigm. Sound familiar? It's the Gartner Hype Cycle again.

Disillusioned by MOOCs, students are sticking to what they know: college. And as a result, Americans have a combined $1.5 trillion in student loans outstanding, up from under $500 billion in 2006. The crisis has gotten so severe that Presidential candidates like Bernie Sanders and Elizabeth Warren are making the cancelation of all student loan debt key planks in their platforms in a grownup version of the old "free ice cream for everyone" promise made by countless Student Body Presidential Hopefuls.

Debt forgiveness won’t solve the underlying issues. The challenge is that we have been taking an either/or approach to education: either we can learn online, or we need to go to college. Granted, schools have experimented with using technology, but success has been limited by trying to squeeze technology into existing ways of doing things.

I think that the solution lies in reimagining learning from the ground up and combining the best of both worlds, letting online do what it does best and doing offline what IRL does best.

To be sure, online education will continue to improve. Improvement is why technologies come out of the Trough of Disillusionment and into the Slope of Enlightenment; true believers keep working on fixing the problem through the Trough and come out the other side with an improved product. I'm particularly fascinated by what Andy Matuschak and Michael Nielsen are working on, especially their plan to create mnemonic videos. And that improvement is a great thing for the hybrid solution!

Meanwhile, there is a huge opportunity to leverage the unprecedented wealth of content available at our fingertips and the tried-and-true benefits of learning together, in-person.

  • What if you could listen to a Knowable course on Launching a Startup on your own time, and then meet regularly with a group of people in your city to do group work, apply what you've learned, provide feedback, and build a support network of other people looking to start a company?

  • What if you could connect with a group of other people interested in learning about Philosophy, and be guided through a curated journey of the best content available - the foundational works downloaded to your Kindle, an MIT Intro to Philosophy Course on EdX, and a series of podcasts that highlight the latest thinking in the field - by a knowledgeable expert who leads weekly IRL discussions via the Socratic method?

  • What if you could bring together people learning about artificial intelligence from different perspectives, technical and philosophical, to debate whether AI should have rights, cementing the knowledge you're consuming by having to actively and competitively apply it?

If you play this out, eventually people will need to ask themselves: Why spend four years and $200k on a college education when you can get the world's best content delivered online, and go to a local place-based community to get guidance on your learning path and make new connections with people who are going through the same journey, all within your day-to-day life?

By taking the best that online and offline have to offer, you can unbundle existing educational options and re-bundle your own with the best pieces: the best content available anywhere, instead of what's available where you happen to be studying; a network of other curious, motivated people in your city; accountability at a fraction of the cost.

It’s time to remix education.

An IRL Members Community of Lifelong Learners has the potential to address some of the issues we've discussed throughout this series. It can build community around a shared passion for learning. It can help us grow, evolve, and improve ourselves, with each other. It can equip people with the tools they need to succeed in a changing job market. And it can provide fulfillment separate from a job.

Learning can provide meaning in itself, and teaching gives people that unbeatable feeling of making a contribution being relied upon by others.

Most importantly, education is spark that can ignite more creation. By equipping people with knowledge and a space to learn, they can acquire the tools and skills necessary to create and build things that empower more people, who in turn can create and build, and so on, in a positive loop.

To me, it's the single biggest opportunity out there, and one that is deeply aligned with my interests and passions. If I were a billionaire (and if billionaires don’t get canceled), I would spend my free time learning with smart, curious people.

That's why I'm going to be working towards making this future a reality. This series and my posts on Online Education have been part of my early exploration of the space, my attempt to learn in public, and I've been really encouraged by what I've discovered. It’s still early days of forming a solution, but I’m all-in on working to solve this problem.

If you're passionate about making this happen with me, or know someone who would, I would love to talk to you!

Links & Listens

I was planning on leaving this week's newsletter at that - the announcement and essay are enough to digest on their own. But then four of my favorite writers wrote three outstanding essays on topics that fascinate me: disruption theory, tools for thought, and Big Things shaping the world. I would be remiss if I didn't share these and strongly encourage you to read them.

Disruption Theory is Real, but Wrong by Alex Danco

Disruption theory is widely accepted, but doesn't hold water in many real world examples. The problem? We've been looking at the wrong level.

🌍 The Big Things: The Most Important Forces Shaping the World by Morgan Housel

There are only a handful of Big Things that you can trace most other events back to. Housel discusses four: World War II, Demographics, Inequality, and Access to Information.

🧠 How Can We Develop Transformative Tools for Thought? by Andy Matuschak & Michael Nielsen

This is a long one, but it's really cool. Matuschak and Nielsen write about the potential for new tools of thought - game-changing tools in the tradition of writing, Hindu-Arabic numerals, and printing - which have the power to radically transform how we think. These are the same guys who brought us the mnemonic medium in Quantum Country, which I've written about here before. (Bonus points for thoughtful commentary on MOOCs)

If you have friends, acquaintances, or even enemies who are talented and passionate about community, education, or building digital tools that enhance offline experiences, please forward this e-mail to them. Having learned first-hand how important it is to work with amazing people at Breather, I'm excited to find a top-notch crew to join me on the next journey.

Thanks for reading!


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