Per My Last E-mail #34

Not Boring People, Data Cult, Flow, Audience --> Community, Appalachia, Spotify, and Gratitude

Hi Friends 👋,

Happy Monday! If you read only two sections today, read the first two.

Introducing: not boring

The What: We are launching an online club for Not Boring people who want to try new and exciting things together IRL, starting in New York City. Not Boring is a diverse community of people who are the best at what they do from 9-5, and want to develop the rest of their life beyond the office and build a more varied network.

Not Boring will start simple with a chat group where members can:

  • Get exclusive access to Not Boring events

  • Start a club around a passion or something you've been wanting to get into

  • Rally a group to go to an art opening, lecture, or meetup

  • Find people to take classes, write, record podcasts, and create with

  • Organize dinners to meet new people over good food and conversation

  • Join an online-offline book club (hopefully more successful than Slack Book Club)

We'll help eliminate two of the biggest impediments people have to being not boring:

  1. Discovery: Each week, we'll surface relevant, high-quality events.

  2. Logistics: In addition to hosting and coordinating Not Boring events, we'll help plan and organize the events, clubs, and dinners that members want to host so that logistics aren't a limiting factor to growth.

Not Boring will grow over time based on the interests of the members. We expect that members will start interest-based clubs, support circles, workout groups, and travel together, but that's probably just scratching the surface. Not Boring will show up in force for each other, time and again.

I'm launching Not Boring with Sam Liebskind. Sam works for a startup called Geneva, which is launching the beta of its group messaging app built for communities today. Geneva is rolling out some exciting functionality with communities like this one in mind, so we opted to plant one of the first of what will be thousands of flags there instead of going with a Slack group.

The Why

Last year, when I was reviewing 2018 and planning 2019, I realized that I was boring and one-dimensional. I spent most of my time working, and when I wasn't working, I was thinking about work. So I made it a goal to become not boring in 2019. I took a writing class, started writing this newsletter, launched Debate Club, joined the OnDeck Fellowship, joined a book club, traveled more often, and generally started saying "yes" more often.

It took a lot of effort, but trying new things with new people made 2019 one of the best years of my life. I've made genuine friendships, learned valuable skills, and had novel experiences. Paradoxically, focusing less on work has opened up more exciting work opportunities, and organically building a diverse network of great people from a variety of industries has been priceless as I've turned my attention to starting a company. Overall, I'm less boring.

So over the past few months, I've talked to hundreds of people about how they learn, build relationships, and explore and maintain hobbies. I've had countless coffees, sent surveys, and held focus groups. I've had as much fun over the past three months as I've ever had because I've been learning by meeting curious, interesting, and generous people and saying yes to new experiences. Specifically, I've learned that:

  • Adult life doesn't have a good answer for college extra-curriculars.

    The real world is more like college than we think. Classes are like jobs, sports are like rec leagues, dorms are like apartment buildings or co-living, social clubs are like fraternities and sororities, bars are like... bars. But extra-curriculars and clubs, which many people cite as their favorite part of the college experience, don't have a real-world equivalent. Our options today are often single-player (reading, writing), one-off (Meetups, trip to the art museum), or those hobbies that everyone has and is embarrassed to give as their answer (travel, hanging out with friends).

    Extra-curriculars allow for a structured, yet low-pressure pursuit of hobbies and interest, with a committed group of people. The skills I learned and friends I made in extra-curriculars have stuck with me more than anything I learned in class. The real world needs something that makes it just as seamless to pursue hobbies and interests.

  • Making connections is easy, building relationships is hard.

    Almost anyone in the world is reachable by e-mail, DM, networking event, or warm intro, and people are surprisingly willing to chat if you have a compelling reason.

    But I've heard over and over again that taking the next step - having that second coffee, keeping the conversation going - is really hard and awkward. The spark almost never strikes in that first conversation; it's cultivated over time as trust builds.

  • The most curious people want to build networks outside of their day job field.

    So many communities that exist today are built around a shared professional or demographic identity. There are Slack groups for DTC people, idea dinners for hedge fund managers, Signal chats for fintech entrepreneurs, and a whole host of even more narrowly defined groups. Those communities are valuable for growth because they create safe spaces with a shared language, and enable growth and opportunities within a specific field.

    But the most curious people I've spoken to value the intersections. They realize that the most interesting new opportunities and ideas are mashups of the best ideas from multiple disciplines. And they want an easier way to generate the serendipity that generates those mashups. They want similarity in intellect, passion, and curiosity, and diversity in everything else.

  • Repeated interaction around growth experiences builds relationships.

    Over and over again, people cited classes and other small group learning activities as the best way they’ve found to build relationships. Genuine relationships are built when you go through a challenge with someone, day after day or week after week, and come out better on the other side.

  • The question, "What do you do outside of work?"makes people cringe.

    I remember sitting in the lobby of Hotel Giraffe three years ago with my mom and her business partner, Liz, when Liz asked, "So, what do you like to do outside of work?" I was knee-deep in growing a startup, and I didn't have an answer. I liked... working.

    As I've talked to people and asked them that same question, the reaction is a visceral embarrassment. "What do you do outside of work?" is a referendum on what we've demonstrated we care about, and most people aren't happy with the answer. It's not surprising. We work so hard on one particular thing that we fail to develop the skills, passions, and interests that open up the universe of potentially much more interesting things.

We're creating Not Boring to make it seamless, fun, and rewarding to explore interests and hobbies outside of work with a curious, adventurous, passionate group of people. We want to build a community that supports each other, makes each other better, and provides each other with opportunities that we couldn't have accessed before. We want the answer to the question, "What do you do outside of work?" to be a point of pride and an important part of our identity.

The How

Finding that magical mix of people is a tiny bit of science and a lot of art. We're going to keep the community small and well-curated to start, and grow as we learn what works.

We are forming a diverse group of people who share some important characteristics: intellectually curious, adventurous, growth-minded, open to experience, generous, and multifaceted. Whether you want to throw events or attend with enthusiasm, contribute your creativity or provide feedback and amplification to others, a strong community needs all types. Other than assholes. Even the smartest, most curious asshole can't join our club.

Not Boring is free to join for now, and if we do start charging a membership fee, people who join before we do will be grandfathered in to free lifetime digital access. For us, this is about learning, meeting great people, and trying new things.

Why join?


  • Access to a digital community of likeminded not boring people

  • Curated and coordinated events and activities

  • Discounted access to events, classes, and experiences


  • Learn and grow through hobbies, interests, and experiences

  • Build a diverse, talented, and interesting network

  • A great answer to "What do you do outside of work?"

If you fit the description, we want you to join, and we want you to bring in your friends who do too. Apply below; admissions will be rolling, and we'll start welcoming people into the club in two weeks. Join us!

Apply Now


Speaking of nerdy fun, I’m excited to partner with Gabi and Leah from DataCult to host the first DataDay Workshop. Gabi and Leah first teamed up at WeWork, where they led and grew the Data Visualization and Data Teams, respectively.

Their key insight is that when every person at a company becomes a data person, you build a “community of employees who feel empowered to use data to solve the most pressing challenges in the business.”

They’ve led week-long workshops within organizations with great results, and now for the first time, they’re hosting a one-day bootcamp with people from a variety of industries and companies.

Getting comfortable with data as non-data-person - being able to speak the language, ask the right questions, and find some of the answers without having to ping the Data team for every little thing - was a great learning from my time at Breather, and I’m excited to go deeper at the DataDay Workshop. Join us!

Sign Up Here

Bonus(es): Per My Last E-mail readers get 25% off with the code DATAFRIENDS and if your company gives you a learning & development budget, you should be able to get this workshop approved and paid for. Check with your HR or People Team!

Links & Listens

The saga of density vs. usefulness continues! After last week’s e-mail, I got replies from a few people who said that they liked the article summaries more than the shorter version with quotes. The summaries helped them decide what to click and read. It’s a good point.

Length ≠ Density. Making something shorter while delivering less value is easy. Just write less. Making something complex shorter and easier to understand while delivering the same or more value is hard. I’ll keep working on it.

💿Flow State Newsletter by Marcus Moretti

Putting this one up top so that you can listen to one of last week’s recommendations while you read the rest of the newsletter.

Too often, the difference between a productive day and a distracted one comes down to what I’m listening to. Too many words, I get distracted. Too calm, I’m too mellow. Too intense, I get short bursts of energy that I can’t sustain all day. Spotify has some good focus playlists, but I can only listen to Deep Focus so many times. And I’ve played out Anja’s recommendation, Heliosphan by Aphex Twin to the point that it showed up at the top of my 2019 Spotify Wrapped.

Luckily, Marcus Moretti sends out “two hours of music that’s perfect for working” every weekday. I subscribed last week and it’s already become a part of my routine. The paid subscription, which I haven’t gone for yet, has extra goodies, but the free version gets you your daily playlist.

🎳 From Audiences to Communities | Web Smith in 2PM

Web is speaking my language in this one, comparing the ecosystem of newsletters and communities to Enlightenment-era coffeehouses. Information exchange and synthesis were rampant in Enlightenment-era coffee houses, the physical scenes in which scenius bloomed:

It wasn’t solely the conversations on matters of sociology, economics, and law that drove the age forward. Sometimes, patrons would overhear concepts that would fill gaps in their own thinking. Other conversations would solidify pivotal ideas, directly or indirectly.

Fascinatingly, innovation declined in the US during prohibition, as people stopped spending informal time in taverns exchanging ideas over a drink. Unstructured space for cross-field idea exchange is crucial to generating new breakthroughs. It will be interesting to see whether newsletters and online communities can evolve to meet that need.

🎸In Appalachia, Crafting a Road to Recovery with Dulcimer Strings | Patricia Leigh Brown in NYT

Yet another great find from Anja. The title tells the story here, but it’s worth reading the full thing. A group of woodworkers in Kentucky are aiding addiction recovery and reducing recidivism by teaching participants how to make instruments, in addition to yoga, adult education, and prayer groups. The story speaks to the power of learning and creating to provide meaning, which will only become more important as more jobs get automated away.

🎧 Eric Weinstein on Impact Theory with Tom Bilyeu

I don’t even know where to begin on this one. Over the course of two hours, Weinstein, a mathematical physicist and Managing Director of Thiel Capital, discusses how The Matrix is actually a disguised documentary, portals we can jump through to learn and achieve new things, the mathematical beauty of music, and how to learn to play songs on a guitar using the handle of a coffee mug in a few minutes.

Weinstein launched his own podcast, The Portal, in 2019. I’ll be listening from the beginning this week.

📡 Spotify and Podcasting by Sidhartha Jha

While we’re on podcasts, Sidhartha Jha wrote a great piece providing an overview of the podcasting landscape and Spotify’s strategy within it.

Jha argues that by combining its existing 250 million listeners (distribution) with its purchases of Gimlet Media (exclusive content) and Anchor (long-tail content) and its recently announced podcast ad network (monetization), Spotify is building the centralizing force for podcasts that Google built for the internet.

What I’m Reading

Gratitude by Oliver Sacks

Gratitude is a series of essays written by neurologist and author Oliver Sacks as he wrestled with terminal cancer and the approaching end of his life. At 63 pages, it’s also a case study on how to convey wisdom, emotion, and synthesized insights clearly and concisely.

It’s a quick and rich read, and you should read the whole thing. Here’s a little preview:

“There will be no one like us when we are gone, but then there is no one like anyone else, ever. When people die, they cannot be replaced. They leave holes that cannot be filled, for it is the fate—the genetic and neural fate—of every human being to be a unique individual, to find his own path, to live his own life, to die his own death.

I cannot pretend I am without fear. But my predominant feeling is one of gratitude. I have loved and been loved; I have been given much and I have given something in return; I have read and traveled and thought and written. I have had an intercourse with the world, the special intercourse of writers and readers.

Above all, I have been a sentient being, a thinking animal, on this beautiful planet, and that in itself has been an enormous privilege and adventure.”

Currently reading:

Black Leopard, Red Wolf by Marlon James

I’m less than 20% in to Black Leopard, Red Wolf, and I still have no idea what’s going on, so I’ll tell you the two reasons I bought it:

  1. It was described as an “African Game of Thrones

  2. James’ first book, A Brief History of Seven Killings, a novel exploring the attempted assassination of Bob Marley that won the Man Booker Prize in 2015, was the best audiobook I’ve ever listened to.

The Great Good Place: Cafes, Coffee Shops, Bookstores, Bars, Hair Salons, and Other Hangouts at the Heart of a Community by Ray Oldenburg

I’m less than 5% in on this one, but it’s come highly recommended by a couple of people I trust. More to come.

What’s Next?

This week will be very not boring. I’m starting a yoga course with Puja and my brother (currently can’t touch my toes), hosting a small Whiskey & Convo on consciousness (while doing Dry January; let me know if you want to get deep with us), kicking off the Write of Passage Fellowship (two days left to figure out my topic), scheduling Debate #3 (great turnout!), and launching the not boring application.

If you know anyone who would like receiving this e-mail or who would make a perfect not boring community member, I’d really appreciate you forwarding this e-mail their way!

Thanks for reading,